AU2015203721B2 - Natural high-potency sweetener compositions with improved temporal profile and/or flavor profile, methods for their formulation, and uses - Google Patents

Natural high-potency sweetener compositions with improved temporal profile and/or flavor profile, methods for their formulation, and uses Download PDF

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AU2015203721B2
AU2015203721B2 AU2015203721A AU2015203721A AU2015203721B2 AU 2015203721 B2 AU2015203721 B2 AU 2015203721B2 AU 2015203721 A AU2015203721 A AU 2015203721A AU 2015203721 A AU2015203721 A AU 2015203721A AU 2015203721 B2 AU2015203721 B2 AU 2015203721B2
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sweet taste
taste improving
acid
polyol
carbohydrate
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Grant E. Dubois
Prashanthi Jella
George A. King
Indra Prakash
Rafael I. San Miguel
Kelly H. Sepcic
Deepthi K. Weerasinghe
Newton R. White
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Coca Cola Co
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Coca Cola Co
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Abstract

The present invention relates generally to improving the taste of natural high-potency non-caloric or low-calorie sweeteners and compositions sweetened therewith. In particular, 5 the present invention relates to compositions that can improve the tastes of natural high potency non-caloric or low-caloric sweteners by inparting a more sugar-like taste or characteristic. In particular, the compositions and methods provide a mere sugar-like temporal profile, including swetness onset and sweetness linger, and/or a more sugar-like flavor profile, including osmotic taste.

Description

ι 2015203721 02 Jul2015
NATURAL HIGH-POTENCY SWEETENER COMPOSITIONS WITH IMPROVED TEMPORAL PROFILE AND/OR FLAVOR PROFILE, METHODS FOR THEIR
FORMULATION, AND USES
The present application is a divisional application of Australian patent 5 application number 2013200558 filed on 31 January 2013, which is in turn a divisional application from Australian patent application number 2006318781, the entire disclosures of which are incorporated herein by reference.
FIELD OF THE INVENTION
The present invention relates generally to improving the taste of natural high-10 potency non-caloric or low-caloric sweeteners and compositions sweetened therewith. In particular, the present invention relates to compositions that can improve the tastes of natural high-potency non-caloric or low-caloric sweeteners by imparting a more sugar-like taste or characteristic. In particular, the compositions and methods provide a more sugar-like temporal profile, including sweetness onset and sweetness linger, and/or a more sugar-like flavor 15 profile, including osmotic taste.
BACKGROUND OF THE INVENTION
Natural caloric sugars, such as sucrose, fructose, and glucose are utilized heavily in beverage, food, pharmaceutical, and oral hygienic/cosmetic industries due to their pleasant taste. In particular, sucrose imparts a desirable taste for consumers. Although sucrose 20 provides superior sweetness characteristics, it is caloric. While calories are necessary for proper bodily functions, there is a need in the market to provide alternative non-caloric or low-caloric sweeteners with sugar-like taste for consumers with sedentary lifestyles or those who are calorie conscious. However, in general, non-caloric or low caloric sweeteners have associated undesirable tastes to consumers such as delayed sweetness onset; lingering sweet 25 aftertaste; bitter taste; metallic taste; astringent taste; cooling taste; licorice-like taste; and/or the like.
Natural high-potency sweeteners, such as rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, dulcoside B, rubusoside, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, 30 siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukuroziosude, phlomisoside I, periandrin I, abrusoside A, and cyclocarioside I generally 2 2015203721 02 Jul2015 cyclocarioside I generally exhibit a sweet taste that has a different temporal profile, maximal response, flavor profile, mouthfeel, and/or adaptation behavior than that of sugar. For example, the sweet tastes of natural high-potency sweeteners are slower in onset and longer in duration than the sweet taste produced by sugar and thus change the taste balance of a food 5 composition. Because of these differences, use of a natural high-potency sweetener to replace a bulk sweetener, such as sugar, in a food or beverage, causes an unbalanced temporal profile and/or flavor profile. In addition to the difference in temporal profile, high-potency sweeteners generally exhibit (i) lower maximal response than sugar, (ii) off tastes including bitter, metallic, cooling, astringent, licorice-like taste, etc., and/or (iii) sweetness which diminishes 10 on iterative tasting. It has previously been described in the art of food/beverage formulation that changing the sweetener in a composition requires re-balancing of the flavor and other taste components, (e.g., acidulants). If the taste profile of natural high-potency sweeteners could be modified to impart specific desired taste characteristics to be more sugar-like, the type and variety of compositions that may be prepared with that sweetener would be 15 significantly expanded. Accordingly, it would be desirable to selectively modify the taste characteristics of natural high-potency sweeteners. As a result, several processes and/or compositions have been described for modifying the taste profile of beverage, food, pharmaceutical, nutraceutical, tobacco, and oral hygienic/cosmetic products sweetened with non-caloric or low-caloric sugar alternative sweeteners. 20 However, improvement in sweetness and sugar-like characters of non-caloric or low-caloric natural sweeteners to provide consumer satisfaction more like that of sucrose, fructose, or glucose still is desired.
The discussion of documents, acts, materials, devices, articles and the like is included in this specification solely for the purpose of providing a context for the present 25 invention. It is not suggested or represented that any or all of these matters formed part of the prior art base or were common general knowledge in the field relevant to the present invention as it existed before the priority date of each claim of this application.
Where the terms "comprise", "comprises", "comprised" or "comprising" are used in this specification (including the claims) they are to be interpreted as specifying the 30 presence of the stated features, integers, steps or components, but not precluding the presence of one or more other features, integers, steps or components, or group thereof. 2015203721 24 Feb 2017 2a
SUMMARY OF THE INVENTION
Generally, this invention addresses the above described need by providing a natural high-potency sweetener (NHPS) composition with improved temporal profile or flavor 5 profile or both, a method for improving the temporal profile and/or flavor profile of a NHPS, NHPS sweetened compositions with improved temporal profile and/or flavor profile, and a method for improving the temporal profile and/or flavor profile of NHPS sweetened compositions. In particular, this invention improves the temporal profile and/or flavor profile by imparting a more sugar-like temporal profile and/or flavor profile. 10 In one aspect, the present invention provides a sweetener composition comprising rebaudioside A and psicose, wherein the rebaudioside A has a purity greater than about 80% by weight on a dry basis and the psicose is in the D-configuration. PCT/US2006/044574 WO 2007/061795 3 2015203721 02 Jul2015
More particularly, this invention encompasses a NHPS composition with a more sugar-like temporal profile and/or flavor profile comprising at least one NHPS and/or at least one modified NHPS and at least one sweet taste improving composition selected from the group consisting of carbohydrates, polyols, amino acids, other sweet .5 taste improving additives, and combinations thereof.
According to another aspect, this invention encompasses a method for imparting a more sugar-like temporal profile and/or flavor profile to a NHPS by combining with at least one NHPS and/or at least one modified NHPS, at least one sweet taste improving composition selected from the group consisting of carbohydrates, polyols, 10 amino acids, other sweet taste improving additives, and combinations thereof.
According to still another aspect, this invention encompasses a NHPS sweetened composition with a more sugar-like temporal profile and/or flavor profile comprising a sweetenable composition, at least one NHPS and/or at least one modified NHPS, and at least one sweet taste improving composition selected from the group 15 consisting of carbohydrates, polyols, amino acids, other sweet taste improving additives, and combinations thereof. According to particular embodiments of this invention, the NHPS sweetened composition is selected from the group consisting of beverage, food, pharmaceutical, nutraceutical, tobacco, oral hygienic/cosmetic products, and the like.
According to still another aspect, this invention encompasses a method for 20 imparting a more sugar-like temporal profile and/or flavor profile to a NHPS sweetened composition by combining with a sweetenable composition, at least one NHPS and/or at least one modified NHPS, and at least one sweet taste improving composition selected from the group consisting of carbohydrates, polyols, amino acids, other sweet taste improving additives, and combinations thereof. Again, according to particular 25 embodiments of this invention, the NHPS sweetened composition is selected from the group consisting of beverage, food, pharmaceutical, tobacco, oral hygienic/cosmetic product, nutraceutical, and the like.
Objects and advantages of the invention will be set forth in part in the following description, or may be obvious from the description, or may be learned through 30 practice of the invention. Unless otherwise defined, all technical and scientific terms and abbreviations used herein have the same meaning as commonly understood by one of PCT/US2006/044574 WO 2007/061795 4 2015203721 02 Μ 2015 ordinary skill in the art to which this invention pertains. Although methods and compositions similar or equivalent to those described herein can be used in the practice of the present invention, suitable methods and compositions are described without intending that any such methods and compositions limit the invention herein.
5 BRIEF DESCRIPTION OF THE DRAWINGS
Fig. 1 is a powder x-ray diffraction scan of rebaudioside A polymorph Form 1 on a plot of the scattering intensity versus the scattering angle 2Θ in accordance with an embodiment of this invention.
Fig. 2 is a powder x-ray diffraction scan of rebaudioside A polymorph Form 10 2 on a plot of the scattering intensity versus the scattering angle 2Θ in accordance with an embodiment of this invention.
Fig. 3 is a powder x-ray diffraction scan of rebaudioside A polymorph Form 3A on a plot of the scattering intensity versus the scattering angle 2Θ in accordance with an embodiment of this invention. 15 Fig. 4 is a powder x-ray diffraction scan of rebaudioside A polymorph Form 3B ori a plot of the scattering intensity versus the scattering angle 2Θ in accordance with an embodiment of this invention.
Fig. 5 is a powder x-ray diffraction scan of rebaudioside A polymorph Form 4 on a plot of the scattering intensity versus the scattering angle 2Θ in accordance with an 20 embodiment of this invention. DETAILED DESCRIPTION OF THE EMBODIMENTS I. Introduction
Reference now will be made in detail to the presently proffered embodiments of the invention. Each example is provided by way of explanation of 25 embodiments of the invention, not limitation of the invention. In fact, it will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the invention. For instance, features illustrated or described as part of one embodiment, can be used on another embodiment to yield a still further embodiment. Thus, it is intended that the present PCT/US2006/044574 WO 2007/061795 5 2015203721 02 Μ 2015 invention cover such modifications and variations within the scope of the appended claims and their equivalents.
As summarized above, this invention encompasses a natural high-potency sweetener (NHPS) composition with improved temporal profile and/or flavor profile, a 5 method for improving the temporal profile and/or flavor profile of a NHPS, NHPS sweetened compositions with improved temporal profile and/or flavor profile, and a method for improving the temporal profile and/or flavor profile of NHPS sweetened compositions. In particular, this invention improves the temporal profile and/or flavor profile of a NHPS by imparting a more sugar-like temporal profile and/or flavor profile to 10 compositions comprising a NHPS. II. Sweet Taste A. Sugar-Like Taste
As used herein, the phrases “sugar-like characteristic,” “sugar-like taste,” “sugar-like sweet,” “sugary,” and “sugar-like” are synonymous. Sugar-like characteristics 15 include any characteristic similar to that of sucrose and include, but are not limited to, maximal response, flavor profile, temporal profile, adaptation behavior, mouthfeel, concentration/response function, tastant/and flavor/sweet taste interactions, spatial pattern selectivity, and temperature effects. These characterisitics are dimensions in which the taste of sucrose is different from the tastes of NHPSs. Of these, however, the flavor 20 profile and temporal profile are particularly important. In a single tasting of a sweet food or beverage, differences (1) in the attributes that constitute a sweetener’s flavor profile and (2) in the rates of sweetness onset and dissipation, which constitute a sweetener’s temporal profile, between those observed for sucrose and for a NHPS can be noted. Desirable embodiments of this invention exhibit a more sugar-like temporal profile, sugar-like flavor 25 profile, or both, titan compositions comprising a NHPS, but without a sweet taste improving composition. Whether or not a characteristic is more sugar-like is determined by an expert sensory panel who taste compositions comprising sugar and compositions comprising a NHPS, both with and without a sweet taste improving composition, and provide their impression as to the similarities of the characteristics of compositions 30 comprising a NHPS, both with and without a sweet taste improving composition, with those comprising sugar. A suitable procedure for determining whether a composition has a more sugar-like taste is described in embodiments described hereinbelow. PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 6
In a particular embodiment, a panel of assessors is used to measure the reduction of sweetness linger. Briefly described, a panel of assessors (generally 8 to 12 individuals) is trained to evaluate sweetness perception and measure sweetness at several time points from when the sample is initially taken into the mouth until 3 minutes after it 5 has been expectorated. Using statistical analysis, the results are compared between samples containing additives and samples that do not contain additives. A decrease in score for a time point measured after the sample has cleared the mouth indicates there has been a reduction in sweetness perception.
The panel of assessors may be trained using procedures well known to those 10 of ordinary skill in the art. In a particular embodiment, the panel of assessors may be trained using the Spectrum™ Descriptive Analysis Method (Meilgaard et al, Sensory Evaluation Techniques. 3rd edition, Chapter 11). Desirably, the focus of training should be the recognition of and the measure of the basic tastes; specifically, sweet. In order to ensure accuracy and reproducibility of results, each assessor should repeat the measure of 15 the reduction of sweetness linger about three to about five times per sample, taking at least a five minute break between each repetition and/or sample and rinsing well with water to clear the mouth.
Generally, the method of measuring sweetness comprises taking a 10 mL sample into the mouth, holding the sample in the mouth for 5 seconds and gently swirling 20 the sample in the mouth, rating the sweetness intensity perceived at 5 seconds, expectorating the sample (without swallowing following expectorating the sample), rinsing with one mouthful of water (e.g., vigorously moving water in mouth as if with mouth wash) and expectorating the rinse water, rating the sweetness intensity perceived immediately upon expectorating the rinse water, waiting 45 seconds and, while waiting 25 those 45 seconds, identifying the time of maximum perceived sweetness intensity and rating the sweetness intensity at that time (moving the mouth normally and swallowing as needed), rating the sweetness intensity after another 10 seconds, rating the sweetness intensity after another 60 seconds (cumulative 120 seconds after rinse), and rating the sweetness intensity after still another 60 seconds (cumulative 180 seconds after rinse). 30 Between samples take a 5 minute break, rinsing well with water to clear the mouth.
In order to clarify the nature of preferred embodiments of this invention, some further explanation of the differences in flavor and temporal profiles between that of PCT/US2006/044574 WO 2007/061795 7 sugar and NHPSs may be helpful. While not wishing to be bound by theory, this further explanation is as follows. B. Flavor Profile
The flavor profile of a sweetener is a quantitative profile of the relative intensities of all of the taste attributes exhibited. Such profiles often are plotted as histograms or radar plots. Sucrose, heretofore, has been accepted as exhibiting only sweetness and generally is employed as a standard for pure sweet taste quality. Most high-potency sweeteners exhibit other qualities of taste in addition to sweetness. Thus, as an example, saccharin, which is a synthetic sweetener, has been found to exhibit both bitter and metallic off tastes. As another example, cyclamate exhibits bitter and salty off tastes. For another example, stevioside and hemandulcin, both NHPSs also have a bitter off taste. Other taste attributes commonly observed for high-potency sweeteners include cooling and licorice-like, and an occasional astringent taste.
It has been discovered, however, that sucrose exhibits a taste attribute, or perhaps even attributes, beyond sweetness. The attributes bitter, sour, salty and umami do not describe it. Nonetheless, its taste is easily discerned from that of high-potency sweeteners exhibiting only sweetness (e.g., aspartame) within the first few seconds of tasting. Thus the taste of sucrose is unique among sweeteners, even among those which do not exhibit any of the “off’ tastes noted above.
In the literature, this unique taste character of sucrose has been referred to in various ways. Terms such as “mouthfeel” and “body” often are used, both terms suggestive of viscosity or other tactile sensations. “Mouthfeel” also can refer to die texture, body, physical, and overall feel a human consumer detects in his or her mouth when tasting the composition. Thus, for example, a sugar-like mouthfeel refers to texture, body, physical, and overall feel similar to that of sugar. However, it is believed now that the unique taste of sucrose relative to that of high-potency sweeteners is not a tactile sensation. A plausible explanation for the unique taste of sucrose as well as other carbohydrate sweeteners is that hyperosmotic solutions induce rapid and sustained decreases in taste bud cell volumes. Specific effects accompany the taste bud cell shrinkage, including enhanced signaling from salt-sensitive taste bud cells in response to NaCl and signaling from sour-sensitive taste bud cells even in the absence of acid. 2015203721 02 Jul2015 8
Although effects on sweet-sensitive taste bud cells were not evaluated, this suggests that sucrose, and carbohydrate sweeteners in general, must elicit taste responses by a pathway in addition to that mediated by the sweetener receptor T1R2/T1R3. This additional pathway likely is mediated by the taste bud cell shrinkage induced by the hyperosmotic character of sugar 5 solutions. Thus, the unique taste of sucrose likely derives from a superimposition of these two pathways of signaling. Sucrose is not perceived as sour or salty nor, for that matter, bitter or umami either. However, it seems that the unique taste of sucrose is derived from signaling to the brain by taste bud cells which normally signal distinct modalities (e.g., strong signaling from sweet-sensitive cells, weak signaling from sour-sensitive cells, weak signaling from salt-10 sensitive cells, etc.). It is believed that this pattern of activity is in significant part responsible for the unique taste of sucrose. In summary, it appears that sucrose is not only a pure sweet stimulus, but also exhibits a second taste attribute, and the superimposition of these two attributes constitutes “sucrose taste.” Given that this second taste attribute of sucrose is due to its osmotic character, it is referred to herein as “osmotic, taste ” 15 Consistent with the line of reasoning developed above, the osmotic taste of sucrose can be observed in the absence of sucrose sweetness. Lactisole is a previously described sweetness inhibitor, and if sucrose is tasted at 10% (w/v) in the presence of lactisole at 0.2% (w/v), the osmotic taste character of sucrose can be observed uncomplicated by the presence of intense sweetness. The taste of this sucrose/lactisole formulation exhibits faint 20 sweetness, faint sourness, as well as “thickness” or “body.” NHFSs do not exhibit osmotic taste and accordingly will not reproduce the flavor profde of sucrose unless additives which reproduce the osmolarity of the sucrose solution targeted without off taste are included.
In principle, any level of osmolarity higher than that of normal saliva exhibits at least some osmotic taste in the mouth. Average concentrations of inorganic ions present in 25 saliva, which are responsible for nearly all of the osmolarity of saliva, are as illustrated in Table 1 below. From the data shown, it is clear that saliva typically has an osmolarity of 70mOsM. Sucrose at 10%, however, is 292 mOsM, more than 4-fold higher, and therefore will cause significant shrinkage of taste bud cell volume and signaling to the central nervous system (CNS). 30 9 2015203721 02 Jul2015
Table 1 Inorganic Ions Saliva Concentration (mM) Na+ 10 K+ 10-25 Ca2* 1.7-3 Mg* 0.5-1 Cl 15-29 h2po4 4-5 hco3 5-7
In the foregoing, it is suggested that the unique taste of sucrose is an outcome of two pathways of taste bud cell signaling, the first pathway proceeding only by activation of 5 sweet-sensitive taste bud cells by direct action at the sweetener receptor T1R2/T1R3, and the second pathway proceeding by activation of several taste bud cell subtypes (e.g., sweet-, sour-and salt-sensitive taste bud cells) by a mechanism mediatedby cell shrinkage due to the increased osmolarity of the sucrose stimulus. While this is believed to be the case, it could be that the complete explanation for the unique taste of sucrose is still somewhat more 10 complicated. It is disclosed that the sweetener receptor T1R2/T1R3 is a heterodimeric receptor constituted of two proteins associated with each other where each of them contains an extracellular domain generally referred to as the Venus Flytrap Domain (VFD). Evidence has been provided that sucrose binds in both VFDs to activate the receptor. At the same time, it has been described that high-potency sweeteners bind differently. Thus, aspartame and 15 neotame bind only to the VFD of T1R2 while, at the same time, cyclamate does not bind in either VFD domain, but rather binds in the transmembrane domain of T1R3. The activated T1R2/T1R3 receptor which follows from sucrose stimulation though binding in both VFDs will be somewhat different in shape from that of activated receptors which derive from the quite different binding of high-potency sweeteners. Thus, complete reproduction of sucrose taste 20 with non-caloric sweeteners also may require simultaneous binding of sweeteners in both VFDs ofTiR2/TiR3. 10 2015203721 02 Μ 2015 C. Temporal Profile 1. Sweetness Onset and Linger
Sucrose exhibits a sweet taste in which the maximal response is perceived quickly and where perceived sweetness disappears relatively quickly on swallowing a food or 5 beverage. In contrast, the sweet tastes of essentially all high-potency sweeteners reach their maximal responses somewhat more slowly and they then decline in intensity more slowly than is the case for sucrose. This decline in sweetness is often referred to as “Sweetness Linger” and is a major limitation for high-potency sweeteners including NHPSs. Slow onset of sweetness also can be an issue. In general, however, sweetness linger is a more significant 10 issue. And so, preferred embodiments of this invention exhibit significant reductions in sweetness linger. As used herein, “temporal profile” of a composition means the intensity of sweetness perceived over time in tasting of the composition by a human. As explained above, the sweet taste of sugar, as well as other carbohydrate and polyol sweeteners, has a quick onset followed by a rapid decrease in sweetness, whereas a NHPS typically has a slower sweet taste 15 onset than sugar followed by a sweetness linger that is longer than sugar.
It is believed that most, if not all, NHPSs bind nonspecifically throughout the oral cavity. Thus, they may stick to the periphery of cells, diffuse into the membranes of cells and even diffuse into cells, the majority of which are not even taste bud cells. This can explain a delay in sweetness onset since attainment of maximal receptor occupancy will occur only 20 subsequent to diffusion of the non-caloric sweetener past an enormous concentration of nonspecific binding sites and the delay in onset of maximal sweetness will be proportional to the propensity for the sweetener to engage in non-specific binding. At the same time, sweetener molecules that are released from the receptor have a very high likelihood of non-specific binding nearby the receptor only to diffuse back to the receptor and stimulate it again and 25 again. Such a process also would delay the time required for clearance of sweetener from the sweetener receptor (i.e., the time for disappearance of sweetness perception). Thus, two approaches for modulating the atypical temporal profiles of a NHPS comprise (i) inhibition of the nonspecific binding of a NHPS by taste bud and epithelial cells and (ii) inhibition of the rate of egress of a NHPS from taste bud and epithelial cells and their membranes. 30 Thus, in particularly desirable embodiments of this invention, the combination of a NHPS with certain sweet taste improving additives reduces the non-specific binding of non-caloric sweeteners to membranes of cells in the oral cavity. Particularly, certain of the 11 2015203721 02 Jul2015 sweet taste improving additives are hyperosmotic stimuli and cause shrinkage of epithelial and taste bud cell membranes, thus retarding the ability of the membranes to engage in nonspecific absorption of NHPSs. Particularly desirable sweet taste improving additives increase osmolarity without introducing excessive off taste. 5 In addition, particularly desirable sweet taste improving additives reduce sweetness linger by retarding the rate of egress of non-specifically absorbed high-potency sweeteners from cell membranes. For example, polymers that bind to the surfaces of cells so as to reduce the fluidities of cell membranes are effective in this manner.
According to still other embodiments of this invention, sweetness linger of a 10 NHPS is masked by the presence of other ingredients which exhibit lingering taste characteristics. For example, NHPSs can be combined with food acids (e.g., acidulants such as citric acid, malic acid, tartaric acid; fumaric acid, and adipic acid) which exhibit sourness that lingers relative to that of mineral acids (e.g., H3PO4), astringent compounds, and other compounds which introduce lingering sensory notes. These embodiments overlay the 15 objectionable sweetness linger with sourness linger and other lingering characteristics such that the overall taste remains in balance over time. 2._Inhibiting The Nonspecific Binding Of NHPS By Taste Bud And
Epithelial Cells
Again, without being bound by theory, high osmolarity solutions improve the 20 temporal profile of NHPSs to be more sugar-like. NHPSs normally exhibit slow sweetness onset and lingering sweetness. The high osmolarity nature of sucrose and other carbohydrate or polyol sweetener solutions contributes to the sweet taste sensation. It has previously been described that (i) high osmolarity solutions cause marked shrinkage of taste bud cells and (ii) taste bud cells absorb and/or adsorb high-potency sweeteners of a variety of chemical 25 structures. Thus, it is hypothesized that high osmolarity solutions cause tightened packing of membrane lipid molecules in taste bud cells as well as in other epithelial cells in the oral cavity and thereby diminish the abilities of such cells to absorb NHPSs. Therefore, any compounds which impart osmolarities sufficient to affect the taste bud and epithelial cell membranes should diminish non-specific binding and thereby 30 PCT/US2006/044574 WO 2007/061795 12 2015203721 02 Jul2015 would cause NHPSs to exhibit sweetness with more sugar-like temporal profiles. In one embodiment, any sweet taste improving composition that imparts increased osmolarity will be effective by this mechanism. 3. Inhibit The Rate Of Egress Of NHPS From Taste Bud And 5 Epithelial Cells And Their Membranes
Another pathway whereby temporal profiles of NHPSs may be improved is to slow the rates of egress of absorbed sweeteners from the taste bud and epithelial cells and their membranes. Thus, in one embodiment, sweet taste improving compositions which reduce the fluidity of the cell membranes improve the temporal profile of NHPS to 10 be more sugar-like. Non-limiting examples of compositions which slow the rates of egress of absorbed sweeteners from the taste bud and epithelial cells and their membranes include sweet taste improving surfactant additives, sweet taste improving cationic polymer additives, sweet taste improving hydrocolloid additives, and other sweet taste improving polymer additives. In yet another embodiment, suitable compositions which slow the rates 15 of egress of absorbed sweeteners from the taste bud and epithelial cells and their membranes include, but are not limited to, cationic polymeric agents such as poly-L-lysines (e.g., poly-L-a-lysine and poly-L-s-lysine), poly-L-orthinine (e.g., poly-L-a-omithine and poly-L-s-omithine), polyethylenimine, and chitosan, as well as surface active compositions including sucrose esters, sorbic acid esters, sorbitan, sorbitan esters, 20 anionic detergents, polysorbates, polyethylene sorbitan esters, propylene glycol esters, glycerol esters, polyglycerol esters, polyethylene esters, complex esters, (e.g., lactate, tartrate, and the like), cationic detergents, gum acacia Senegal, gum acacia seyal, anionic polymers (e.g., polyaspartic acid), polyethylene glycol, lecithins, and saponins. The polymeric agents are hypothesized to bind to cell surfaces and engage in multiple points of 25 binding contact and reduce the fluidity of the cell membranes. II. NHPS Sweetener And Sweetened Compositions
It has been discovered that at least one NHPS and/or modified NHPS in combination with at least one sweet taste improving composition imparts a more sugarlike taste. In a desired embodiment, a composition and method with an improved 30 temporal profile and/or flavor profile are provided. In another embodiment, NHPS-sweetened compositions With a more sugar-like temporal profile and/or flavor profile PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 13 comprising a sweetenable composition, at least one NHPS and/or at least one modified NHPS, and at least one sweet taste improving composition are provided. A. Orally Ingestible Sweetenable Compositions A suitable sweetenable composition can be any material suitable for 5 sweetening with a sweetener and desirably is an orally ingestible composition. By the term "orally ingestible composition", as used herein, is meant substances which are contacted with the mouth of man or animal, including substances which are taken into and subsequently ejected from the mouth and substances which are drunk, eaten, swallowed or otherwise ingested, and are safe for human or animal consumption when used in a 10 generally acceptable range.
There are no restrictions on the type of orally ingestible compositions encompassed by embodiments of this invention as long as they are safe for human consumption when used in a generally acceptable range. These compositions include food, beverage, pharmaceutical, tobacco, nutraceutical, oral hygienic/cosmetic products, 15 and the like. Non-limiting examples of these products include non-carbonated and carbonated beverages such as colas, ginger ales, root beers, ciders, fruit-flavored soft drinks (e.g., citrus-flavored soft drinks such as lemon-lime or orange), powdered soft drinks (e.g., cola, juice, tea, water, coffee), and the like; fruit juices originating in fruits or vegetables, fruit juices including squeezed juices or the like, fruit juices containing fruit 20 particles, fruit beverages, fruit juice beverages, beverages containing fruit juices, beverages with fruit flavorings, vegetable juices, juices containing vegetables, and mixed juices containing fruits and vegetables; sport drinks, energy drinks, near water and the like drinks (e.g., water with natural or artificial flavorants); tea type or favorite type beverages such as coffee, cocoa, black tea, green tea, oolong tea and the like; beverages containing 25 milk components such as milk beverages, coffee containing milk components, cafe au lait, milk tea, fruit milk beverages, drinkable yogurt, lactic acid bacteria beverages or the like; dairy products; bakery products; desserts such as yogurt, jellies, drinkable jellies, puddings, Bavarian cream, blancmange, cakes, brownies, mousse and the like, sweetened food products eaten at tea time or following meals; frozen foods; cold confections, e.g. 30 types of ice cream such as ice cream, ice milk, lacto-ice and the like (food products in which sweeteners and various other types of raw materials are added to milk products, and the resulting mixture is agitated and frozen), and ice confections such as sherbets, dessert PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 14 ices and the like (food products in which various other types of raw materials are added to a sugary liquid, and the resulting mixture is agitated and frozen); ice cream; general confections, e. g., baked confections or steamed confections such as cakes, crackers, biscuits, buns with bean-jam filling and the like; rice cakes and snacks; table top products; 5 general sugar confections such as chewing gum (e.g. including compositions which comprise a substantially water-insoluble, chewable gum base, such as chicle or substitutes thereof, including jetulong, guttakay rubber or certain comestible natural synthetic resins or waxes), hard candy, soft candy, mints, nougat candy, jelly beans and the like; sauces including fruit flavored sauces, chocolate sauces and the like; edible gels; cremes 10 including butter cremes, flour pastes, whipped cream and the like; jams including strawberry jam, marmalade and the like; breads including sweet breads and the like or other starch products; spice; general condiments including seasoned soy sauce used on roasted meats, roast fowl, barbecued meat and the like, as well as tomato catsup, sauces, noodle broth and the like; processed agricultural products, livestock products or seafood; 15 processed meat products such as sausage and the like; retort food products, pickles, preserves boiled in soy sauce, delicacies, side dishes; snacks such as potato chips, cookies, or the like; cereal products; drugs or quasi-drugs that are administered orally or used in the oral cavity (e.g., vitamins, cough syrups, cough drops, chewable medicine tablets, amino acids, bitter-tasting agents, acidulants or the like), wherein the drug may be in solid, liquid, 20 gel, or gas form such as a pill, tablet, spray, capsule, syrup, drop, troche agent, powder, and the like; personal care products such as other oral compositions used in the oral cavity such as mouth freshening agents, gargling agents, mouth rinsing agents, toothpaste, tooth polish, dentrifices, mouth sprays, teeth-whitening agent and the like; dietary supplements; tobacco products including smoke and smokeless tobacco products such as snuff, 25 cigarette, pipe and cigar tobacco, and all forms of tobacco such as shredded filler, leaf, stem, stalk, homogenized leaf cured, reconstituted binders and reconstituted tobacco from tobacco dust, fines or ether sources in sheet, pellet or other forms, tobacco substitutes formulated from non-tobacco materials, dip or chewing tobacco; animal feed; nutraceutical products, which includes any food or part of a food that may provide 30 medicinal or health benefits, including the prevention and treatment of disease (e.g., cardiovascular disease and high cholesterol, diabetes, osteoporosis, inflammation, or autoimmune disorders), non-limiting examples of nutraceuticals include naturally nutrient- PCT/US2006/044574 WO 2007/061795 15 2015203721 02 Μ 2015 rich or medicinally active food, such as garlic, soybeans, antioxidants, phytosterols and phytostanols and their esters, fibers, glucosamine, chondroitin sulfate, ginseng, ginko, Echinacea, or the like; other nutrients that provide health benefits, such as amino acids, vitamins, minerals, carotenoids, dietary fiber, fatty acids such as omega-3 or omega-6 fatty 5 acids, DHA, EPA, or ALA which can be derived from plant or animal sources (e.g., salmon and other cold-water fish or algae), flavonoids, phenols, polyphenols (e.g., catechins, proanthocyanidins, procyanidins, anthocyanins, quercetin, resveratrol, isoflavones, curcumin, punicalagin, ellagitannin, citrus flavonoids such as hesperidin and naringin, and chlorogenic acid), polyols, prebiotics/probiotics, phytoestrogens, 10 sulfides/thiols, policosanol, saponin, mbisco peptide, appetite suppressants, hydration agents, autoimmune agents, C-reactive protein reducing agents, or anti-inflammatory agents; or any other functional ingredient that is beneficial to the treatment of specific diseases or conditions, such as diabetes, osteoporosis, inflammation, or high cholesterol levels in the blood. In accordance with desirable embodiments of this invention, NHPS 15 sweetened compositions such as those described hereinabove comprise a sweetenable orally ingestible composition, at least one NHPS and/or at least one modified NHPS, and at least one sweet taste improving composition selected from the group consisting of carbohydrates, polyols, amino acids, other sweet taste improving additives, and combinations thereof. For example, according to a particular embodiment of this 20 invention, a NHPS sweetened beverage comprises an orally ingestible beverage composition, such as an aqueous beverage composition or the like, and a NHPS composition with a more sugar-like temporal profile and/or flavor profile, as disclosed herein. In addition, according to a particular embodiment of this invention, a NHPS sweetened food comprises an orally ingestible food composition and a NHPS composition 25 with a more sugar-like temporal profile and/or flavor profile, as disclosed herein. In addition, according to a particular embodiment of this invention, a NHPS sweetened pharmaceutical comprises a pharmaceutically active composition and/or pharmaceutically acceptable salts thereof, and a NHPS composition with a more sugar-like temporal profile and/or flavor profile, as disclosed herein. Alternatively, in addition, according to a 30 particular embodiment of this invention, a NHPS sweetened pharmaceutical comprises a pharmaceutically active composition and/or pharmaceutically acceptable salts thereof and a coating comprising an orally ingestible composition and a NHPS composition with a WO 2007/061795 PCT/US2006/044574 16 2015203721 02 Jul2015 more sugar-like temporal profile and/or flavor profile, as disclosed herein. In addition, according to a particular embodiment of this invention, a NHPS sweetened tobacco product comprises a tobacco and a NHPS composition with a more sugar-like temporal profile and/or flavor profile, as disclosed herein. In addition, according to a particular 5 embodiment of this invention, a NHPS sweetened nutraceutical product comprises an orally ingestible nutraceutical composition and a NHPS composition with a more sugarlike temporal profile and/or flavor profile, as disclosed herein. In addition, according to a particular embodiment of this invention, a NHPS sweetened oral hygenic product comprises an orally ingestible oral hygenic composition and a NHPS composition with a 10 more sugar-like temporal profile and/or flavor profile, as disclosed herein. In addition, according to a particular embodiment of this invention, a NHPS sweetened cosmetic product comprises an orally ingestible cosmetic composition and a NHPS composition with a more sugar-like temporal profile and/or flavor profile, as disclosed herein. B. Natural High-Potency Sweeteners 15 As used herein, the phrase “natural high-potency sweetener” or “NHPS” means any sweetener found in nature which may be in raw, extracted, purified, or any other form, singularly or in combination thereof and characteristically have a sweetness potency greater than sucrose, fructose, or glucose, yet have less calories. Non-limiting examples of NHPSs suitable for embodiments of this invention includes natural high-20 potency sweeteners, such as rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, dulcoside B, rubusoside, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hemandulcin, phyllodulcin, glycyphyllin, phloridzin, 25 trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, and cyclocarioside I. Alternatively, the raw, extracted, or purified NHPS may be modified. Modified NHPSs includes NHPSs which have been altered naturally or synthetically. For example, a modified NHPS includes, but is not limited to, NHPSs which have been fermented, 30 contacted with enzyme, or derivatized, or the product of any process wherein at least one atom has been added to, removed from, or substituted on the NHPS. In one embodiment, at least one modified NHPS may be used in combination with at least one NHPS. In PCT/US2006/044574 WO 2007/061795 17 2015203721 02 Μ 2015 another embodiment, at least one modified NHPS may be used without a NHPS, Thus, a modified NHPS may be substituted for a NHPS or be used in combination with a NHPS for any of the embodiments described herein. For the sake of brevity, however, in the description of embodiments of this invention, a modified NHPS is not described expressly 5 as an alternative to an unmodified NHPS, but it should be understood that a modified NHPS can be substituted for a NHPS in any embodiment disclosed herein.
In one embodiment, extracts of NHPSs may be used in any purity percentage. In another embodiment, when a NHPS is used as a non-extract, the purity of the NHPS may range, for example, from about 25% to about 100%. In another example, 10 the purity of the NHPS may range from about 50% to about 100%; from about 70% to about 100%; from about 80% to about 100%; from about 90% to about 100%; from about 95% to about 100%; from about 95% to about 99.5%; from about 97% to about 100%; from about 98% to about 100%; and from about 99% to about 100%.
Purity, as used here, represents the weight percentage of a respective NHPS 15 compound present in a NHPS extract, in raw or purified form. In one embodiment, a steviolglycoside extract comprises a particular steviolglycoside in a particular purity, with the remainder of the stevioglycoside extract comprising a mixture of other steviolglycosides.
To obtain a particularly pure extract of a NHPS, such as rebaudioside A, it 20 may be necessary to purify the cmde extract to a substantially pure form. Such methods generally are known to those of ordinary skill in the art.
An exemplary method for purifying a NHPS, such as rebaudioside A, is described in the co-pending patent application no. 60/805,216, entitled “Rebaudioside A Composition and Method for Purifying Rebaudioside A,” filed on June 19, 2006, by 25 inventors DuBois, et al., the disclosure of which is incorporated herein by reference in its entirety.
Briefly described, substantially pure rebaudioside A is crystallized in a single step from an aqueous organic solution comprising at least one organic solvent and water in an amount from about 10 % to about 25 % by weight, more particularly from 30 about 15 % to about 20 % by weight. Organic solvents desirably comprise alcohols, acetone, and acetonitile. Non-limiting examples of alcohols include ethanol, methanol, PCT/US2006/044574 WO 2007/061795 18 2015203721 02 Jul2015 isopranol, 1-propanol, 1-butanol, 2-butanol, tert-butanol, and isobutanol. Desirably, the at least one organic solvent comprises a mixture of ethanol and methanol present in the aqueous organic solution in a weight ratio ranging from about 20 parts to about 1 part ethanol to 1 part methanol, more desirably from about 3 parts to about 1 part ethanol to 1 5 part methanol.
Desirably, the weight ratio of the aqueous organic solvent and crude rebaudioside A ranges from about 10 to about 4 parts aqueous organic solvent to 1 part crude rebaudioside A, more particularly from about 5 to about 3 parts aqueous organic solvent to 1 part crude rebaudioside A. 10 In an exemplary embodiment, the method of purifying rebaudioside A is carried out at approximately room temperature. In another embodiment, the method of purifying rebaudioside A further comprises the step of heating the rebaudioside A solution to a temperature in a range from about 20°C to about 40°C, or in another embodiment to a reflux temperature, for about 0.25 hours to about 8 hours. In another exemplary 15 embodiment, wherein the method for purifying rebaudioside A comprises the step of heating the rebaudioside A solution, the method further comprises the step of cooling the rebaudioside A solution to a temperature in the range from about 4°C to about 25°C for about 0.5 hours to about 24 hours.
According to particular embodiments, the purity of rebaudioside A may 20 range from about 50% to about 100%; from about 70% to about 100%; from about 80% to about 100%; from about 90% to about 100%; from about 95% to about 100%; from about 95% to about 99.5%; from about 96% to about 100%; from about 97% to about 100%; from about 98% to about 100%; and from about 99% to about 100%. According to particularly desirable embodiments, upon crystallization of crude rebaudioside A, the 25 substantially pure rebaudioside A composition comprises rebaudioside A in a purity greater than about 95 % by weight up to about 100% by weight on a dry basis. In other exemplary embodiments, substantially pure rebaudioside A comprises purity levels of rebaudioside A greater than about 97 % up to about 100% rebaudioside A by weight on a dry basis, greater than about 98 % up to about 100% by weight on a dry basis, or greater 30 than about 99 % up to about 100% by weight on a dry basis. The rebaudioside A solution during the single crystallization step may be stirred or unstirred. PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 19
In an exemplary embodiment, the method of purifying rebaudioside A further comprises the step of seeding (optional step) the rebaudioside A solution at an appropriate temperature with high-purity crystals of rebaudioside A sufficient to promote crystallization of the rebaudioside A to form pure rebaudioside A. An amount of 5 rebaudioside A sufficient to promote crystallization of substantially pure rebaudioside A comprises an amount of rebaudioside A from about 0.0001 % to about 1 % by weight of the rebaudioside A present in the solution, more particularly from about 0.01 % to about 1 % by weight. An appropriate temperature for the step of seeding comprises a temperature in a range from about 18°C to about 35°C.
10 In another exemplary embodiment, the method of purifying rebaudioside A further comprises the steps of separating and washing the substantially pure rebaudioside A composition. The substantially pure rebaudioside A composition may be separated from the aqueous organic solution by a variety of solid-liquid separation techniques that utilize centrifugal force, that include, without limitation, vertical and horizontal perforated 15 basket centrifuge, solid bowl centrifuge, decanter centrifuge, peeler type centrifuge, pusher type centrifuge, Heinkel type centrifuge, disc stack centrifuge and cyclone separation. Additionally, separation may be enhanced by any of pressure, vacuum, and gravity filtration methods, that include, without limitation, the use of belt, drum, nutsche type, leaf, plate, Rosenmund type, sparkler type, and bag filters and filter press. Operation 20 of the rebaudioside A solid-liquid separation device may be continuous, semi-continuous or in batch mode. The substantially pure rebaudioside A composition also may be washed on the separation device using various aqueous organic solvents and mixtures thereof. The substantially pure rebaudioside A composition can be dried partially or totally on the separation device using any number of gases, including, without limitation, nitrogen and 25 argon, to evaporate residual liquid solvent. The substantially pure rebaudioside A composition may be removed automatically or manually from the separation device using liquids, gases or mechanical means by either dissolving the solid or maintaining the solid form.
In still another exemplary embodiment, the method of purifying 30 rebaudioside A further comprises the step of drying the substantially pure rebaudioside A composition using techniques well known to those skilled in the art, non-limiting examples of which include the use of a rotary vacuum dryer, fluid bed dryer, rotary tunnel PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 20 dryer, plate dryer, tray dryer, Nauta type dryer, spray dryer, flash dryer, micron dryer, pan dryer, high and low speed paddle dryer and microwave dryer. In an exemplary embodiment, the step of drying comprises drying the substantially pure rebaudioside A composition using a nitrogen or argon purge to remove the residual solvent at a 5 temperature in a range from about 40°C to about 60°C for about 5 hours to about 100 hours.
In yet another exemplary embodiment, wherein the crude rebaudioside A mixture comprises substantially no rebaudioside D impurity, the method of purifying rebaudioside A further comprises the step of slurrying the composition of substantially 10 pure rebaudioside A with an aqueous organic solvent prior to the step of drying die substantially pure rebaudioside A composition. The slurry is a mixture comprising a solid and an aqueous organic or organic solvent, wherein the solid comprises the substantially pure rebaudioside A composition and is soluble only sparingly in the aqueous organic or organic solvent. In an embodiment, the substantially pure rebaudioside A composition 15 and aqueous organic solvent are present in the slurry in a weight ratio ranging from about 15 parts to 1 part aqueous organic solvent to 1 part substantially pure rebaudioside A composition. In one embodiment, the slurry is maintained at room temperature. In another embodiment, the step of slurrying comprises heating the slurry to a temperature in a range from about 20 to about 40°C. The substantially pure rebaudioside A composition 20 is slurried for about 0.5 hours to about 24 hours.
In still yet another exemplary embodiment, the method of purifying rebaudioside A further comprises the steps of separating the substantially pure rebaudioside A composition from the aqueous organic or organic solvent of the slurry and washing the substantially pure rebaudioside A composition followed by the step of drying 25 the substantially pure rebaudioside A composition.
If further purification is desired, the method of purifying rebaudioside A described herein may be repeated or the substantially pure rebaudioside A composition may be purified further using an alternative purification method, such as the column chromatography. 30 It also is contemplated that other NHPSs may be purified using the purification method described herein, requiring only minor experimentation that would be PCT/US2006/044574 WO 2007/061795 21 2015203721 02 Μ 2015 obvious to those of ordinary skill in the art.
The purification of rebaudioside A by crystallization as described above results in the formation of at least four different polymorphs: Form 1: a rebaudioside A hydrate; Form 2: an anhydrous rebaudioside A; Form 3: a rebaudioside A solvate; and 5 Form 4: an amorphous rebaudioside A. The aqueous organic solution and temperature of the purification process influence the resulting polymorphs in the substantially pure rebaudioside A composition. Figures 1-5 are exemplary powder x-ray diffraction (XRPD) scans of polymorphs Form 1 (hydrate), Form 2 (anhydrate), Form 3A (methanol solvate), Form 3B (ethanol solvate), and Form 4 (amorphous), respectively. 10 The material properties of the four rebaudioside A polymorphs are summarized in the following table:
Table 2: Rebaudioside A Polymorphs
Form 1 Form 2 Form 3 Form 4 Polymorph Polymorph Polymorph Polymorph Rate of dissolution in H20 at 25°C Very low (<0.2 %/6 0 minutes) Intermediate (<30 %/5 minutes) High (> 30 % 15 minutes) High (> 35 % 15 minutes) Alcohol content < 0.5 % <1 % 1-3% Moisture content >5% <1 % <3% 6.74 %
The type of polymorph formed is dependent on the composition of the 15 aqueous organic solution, the temperature of the crystallization step, and the temperature during the drying step. Form 1 and Form 3 are formed during the single crystallization step while Form 2 is formed during the drying step after conversion from Form 1 or Form 3.
Low temperatures during the crystallization step, in the range of about 20°C 20 to about 50°C, and a low ratio of water to the organic solvent in the aqueous organic solvent results in the formation of Form 3. High temperatures during the crystallization step, in the range of about 50°C to about 80°C, and a high ratio of water to the organic solvent in the aqueous organic solvent results in the formation of the Form 1. Form 1 can be converted to Form 3 by slurrying in an anhydrous solvent at room temperature (2-16 25 hours) or at reflux for approximately (0.5-3 hours). Form 3 can be converted to Form 1 by slurrying the polymorph in water at room temperature for approximately 16 hours or at reflux for approximately 2-3 hours. Form 3 can be converted to the Form 2 during the PCT/US2006/044574 WO 2007/061795 22 2015203721 02 Μ 2015 drying process; however, increasing either the drying temperature above 70°C or the drying time of a substantially pure rebaudioside A composition can result in decomposition of the rebaudioside A and increase the remaining rebaudioside B impurity in the substantially pure rebaudioside A composition. Form 2 can be converted to Form 1 5 with the addition of water.
Form 4 may be formed from Form 1, 2, 3, or combinations thereof, using methods well known to those of ordinary skill in the art. Non-limiting examples of such methods include melt-processing, ball milling, crystallization, lypophilization, cryogrinding, and spray drying. In a particular embodiment, Form 4 can be prepared from 10 a substantially pure rebaudioside A composition obtained by the purification methods described hereinabove by spray-drying a solution of the substantially pure rebaudioside A composition.
The NHPSs may be used individually or in combination with other NHPSs, as long as the combined effect does not adversely affect the taste of the sweetener 15 composition or orally sweetened composition. For example, particular embodiments comprise combinations of NHPS, such as steviolglycosides. Non-limiting examples of suitable stevioglycosides which may be combined include rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, dulcoside B, rubusoside, stevioside, and steviolbioside. According to particularly desirable 20 embodiments of the present invention, the combination of high-potency sweeteners comprises rebaudioside A in combination with rebaudioside B, rebaudioside C, rebaudioside E, rebaudioside F, stevioside, steviolbioside, dulcoside A, or combinations thereof.
Generally, according to a particular embodiment, rebaudioside A is present 25 in the combination of steviolglycosides in an amount in the range of about 50 to about 99.5 weight percent of the combination of high-potency sweeteners, more desirably in the range of about 70 to about 90 weight percent, and still more desirably in the range of about 75 to about 85 weight percent.
In another particular embodiment, rebaudioside B is present in the 30 combination of high-potency sweeteners in an amount in the range of about 1 to about 8 weight percent of the combination of high-potency sweeteners, more desirably in the range WO 2007/061795 PCT/US2006/044574 23 2015203721 02 Μ 2015 of about 2 to about 5 weight percent, and still more desirably in the range of about 2 to about 3 weight percent. hi another particular embodiment, rebaudioside C is present in the combination of high-potency sweeteners in an amount in the range of about 1 to about 10 5 weight percent of the combination of high-potency sweeteners, more desirably in the range of about 3. to about 8 weight percent, and still more desirably in the range of about 4 to about 6 weight percent.
In still another particular embodiment, rebaudioside E is present in the combination of high-potency sweeteners in an amount in the range of about 0.1 to about 4 10 weight percent of the combination of high-potency sweeteners, more desirably in the range of about 0.1 to about 2 weight percent, and still more desirably in the range of about 0.5 to about 1 weight percent.
In still another particular embodiment, rebaudioside F is present in the combination of high-potency sweeteners in an amount in the range of about 0.1 to about 4 15 weight percent of the combination of high-potency sweeteners, more desirably in the range of about 0.1 to about 2 weight percent, and still more desirably in the range of about 0.5 to about 1 weight percent.
In still yet another particular embodiment, dulcoside A is present in the combination of high-potency sweeteners in an amount in the range of about 0.1 to about 4 20 weight percent of the combination of high-potency sweeteners, more desirably in the range of about 0.1 to about 2 weight percent, and still more desirably in the range of about 0.5 to about 1 weight percent.
In yet another particular embodiment, dulcoside B is present in the combination of high-potency sweeteners in an amount in the range of about 0.1 to about 4 25 weight percent of the combination of high-potency sweeteners, more desirably in the range of about 0.1 to about 2 weight percent, and still more desirably in the range of about 0.5 to about 1 weight percent.
In another particular embodiment, stevioside is present in the combination of high-potency sweeteners in an amount in the range of about 0.5 to about 10 weight 30 percent of the combination of high-potency sweeteners, more desirably in the range of PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 24 about 1 to about 6 weight percent, and still more desirably in the range of about 1 to about 4 weight percent.
In still another particular embodiment, steviolbioside is present in the combination of high-potency sweeteners in an amount in the range of about 0.1 to about 4 5 weight percent of the combination of high-potency sweeteners, more desirably in the range of about 0.1 to about 2 weight percent, and still more desirably in the range of about 0.5 to about 1 weight percent.
According to a particularly desirable embodiment, the high-potency sweetener composition comprises a combination of rebaudioside A, stevioside, 10 rebaudioside B, rebaudioside C, and rebaudioside F; wherein rebaudioside A is present in the combination of high-potency sweeteners in an amount in the range of about 75 to about 85 weight percent based on the total weight of the combination of high-potency sweeteners, stevioside is present in an amount in the range of about 1 to about 6 weight percent, rebaudioside B is present in an amount in the range of about 2 to about 5 weight 15 percent, rebaudioside C is present in an amount in the range of about 3 to about 8 weight percent, and rebaudioside F is present in an amount in the range of about 0.1 to about 2 weight percent.
In addition, those of ordinary skill in the art should appreciate that the sweetener composition can be customized to obtain a desired calorie content. For 20 example, a low-caloric or non-caloric NHPS and/or other caloric additives may be combined with a caloric natural sweetener to produce a sweetener composition with a preferred calorie content. C. Sweet Taste Improving Compositions
As used herein, the phrase “sweet taste improving composition” includes 25 any composition which imparts a more sugar-like temporal profile or sugar-like flavor profile or both to a NHPS. Examples of sweet taste improving compositions include, but are not limited to, carbohydrates, polyols, amino acids, and other sweet taste improving taste additives imparting such sugar-like characteristics.
The term “carbohydrate” generally refers to aldehyde or ketone compounds 30 substituted with multiple hydroxyl groups, of the general formula (CH20)n, wherein n is 3-30, as well as their oligomers and polymers. The carbohydrates of the present invention PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 25 can, in addition, be substituted or deoxygenated at one or more positions. Carbohydrates as used herein encompasses unmodified carbohydrates, carbohydrate derivatives, substituted carbohydrates, and modified carbohydrates. Modified carbohydrate means any carbohydrate wherein at least one atom has been added, removed, substituted, or 5 combinations thereof. Thus, carbohydrate derivatives or substituted carbohydrates include substituted and unsubstituted monosaccharides, disaccharides, oligosaccharides, and polysaccharides. The carbohydrate derivatives or substituted carbohydrates optionally can be deoxygenated at any corresponding C-position, and/or substituted with one or more moieties such as hydrogen, halogen, haloalkyl, carboxyl, acyl, acyloxy, amino, amido, 10 carboxyl derivatives, alkylamino, dialkylamino, arylamino, alkoxy, aryloxy, nitro, cyano, sulfo, mercapto, imino, sulfonyl, sulfenyl, sulfinyl, sulfamoyl, carboalkoxy, carboxamido, phosphonyl, phosphinyl, phosphoryl, phosphino, thioester, thioether, oximino, hydrazino, carbamyl, phospho, phosphonato, or any other viable functional group provided die carbohydrate derivative or substituted carbohydrate functions to improve the sweet taste of 15 a NHPS.
Non-limiting examples of carbohydrates in embodiments of this invention include tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g., α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), maltodextrin (including resistant maltodextrins such as Fibersol-2™), dextran, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, 20 lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, glucono-lactone, abequose, galactosamine, beet oligosaccharides, isomalto-oligosaccharides (isomaltose, 25 isomaltotriose, panose and the like), xylo-oligosaccharides (xylotriose, xylobiose and the like), gentio-oligoscaccharides (gentiobiose, gentiotriose, gentiotetraose and the like), sorbose, nigero-oligosaccharides, palatinose oligosaccharides, fucose, ffuctooligosaccharides (kestose, nystose and the like), maltotetraol, maltotriol, malto-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose 30 and the like), lactulose, melibiose, raffinose, rhamnose, ribose, isomerized liquid sugars such as high fructose com/starch syrup (e.g., HFCS55, HFCS42, or HFCS90), coupling PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 26 sugars, soybean oligosaccharides, and glucose syrup. Additionally, the carbohydrates may be in either the D- or L- configuration.
The term “alkyl”, as used herein, unless otherwise specified, refers to a saturated straight, branched, or cyclic, primary, secondary, or tertiary hydrocarbon, 5 typically of Q to Cig, and specifically includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, cyclopentyl, isopentyl, neopentyl, hexyl, isohexyl, cyclohexyl, cyclohexylmethyl, 3-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, and .3,3-dimethylbutyl. The alkyl group optionally can be substituted with one or more moieties selected from the group consisting of hydroxyl, carboxy, carboxamido, carboalkoxy, acyl, 10 amino, alkylamino, arylamino, alkoxy, aryloxy, nitro, cyano, sulfo, sulfato, phospho, phosphato, or phosphonato.
The term “alkenyl”, as referred to herein, and unless otherwise specified, refers to a straight, branched, or cyclic hydrocarbon of C2 to Cjo with at least one double bond. The alkenyl groups optionally can be substituted in the same manner as described 15 above for the alkyl groups and also optionally can be substituted with a substituted or unsubstituted alkyl group.
The term “alkynyl”, as referred to herein, and unless otherwise specified, refers to a C2 to C10 straight or branched hydrocarbon with at least one triple bond. The alkynyl groups optionally can be substituted in the same manner as described above for 20 the alkyl groups and also optionally can be substituted with a substituted or unsubstituted alkyl group.
The term “aryl”, as used herein, and unless otherwise specified, refers to phenyl, biphenyl, or naphthyl, and preferably phenyl. The aryl group optionally can be substituted with one or more moieties selected from the group consisting of hydroxyl, 25 acyl, amino, halo, carboxy, carboxamido, carboalkoxy, alkylamino, alkoxy, aryloxy, nitro, cyano, sulfo, sulfato, phospho, phosphato, or phosphonato.
The term “heteroaryl” or “heteroaromatic”, as used herein, refers to an aromatic or unsaturated cyclic moiety that includes at least one sulfur, oxygen, nitrogen, or phosphorus in the aromatic ring. Non-limiting examples are furyl, pyridyl, pyrimidyl, 30 thienyl, isothiazolyl, imidazolyl, tetrazolyl, pyrazinyl, benzofuranyl, benzothiophenyl, quinolyl, isoquinolyl, benzothienyl, isobenzofuryl, pyrazolyl, indolyl, isoindolyl, PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 27 benzimidazolyl, purinyl, carbazolyl, oxazolyl, thiazolyl, isothiazolyl, 1,2,4-thiadiazolyl, isooxazolyl, pyrrolyl, quinazolinyl, pyridazinyl, pyrazinyl, cinnolinyl, phthalazinyl, quinoxalinyl, xanthinyl, hypoxanthinyl, and pteridinyl. The heteroaryl or heteroaromatic group optionally can be substituted with one or more moieties selected from the group 5 consisting of hydroxyl, acyl, amino, halo, alkylamino, alkoxy, aryloxy, nitro, cyano, sulfo, sulfato, phospho, phosphato, or phosphonato.
The term “heterocyclic” refers to a saturated nonaromatic cyclic group which may be substituted, and wherein there is at least one heteroatom, such as oxygen, sulfur, nitrogen, or phosphorus in the ring. The heterocyclic group optionally can be 10 substituted in the same manner as described above for the heteroaryl group.
The term “aralkyl”, as used herein, and unless otherwise specified, refers to an aryl group as defined above linked to the molecule through an alkyl group as defined above. The term alkaryl, as used herein, and unless otherwise specified, refers to an alkyl group as defined above linked to the molecule through an aryl group as defined above. 15 The aralkyl or alkaryl group optionally can be substituted with one or more moieties selected from the group consisting of hydroxyl, carboxy, carboxamido, carboalkoxy, acyl, amino, halo, alkylamino, alkoxy, aryloxy, nitro, cyano, sulfo, sulfato, phospho, phosphato, or phosphonato.
The term “halo”, as used herein, specifically includes chloro, bromo, iodo, 20 and fluoro.
The term “alkoxy”, as used herein, and unless otherwise specified, refers to a moiety of the structure -O-alkyl, wherein alkyl is as defined above.
The term “acyl”, as used herein, refers to a group of the formula C(0)R', wherein R’ is an alkyl, aryl, alkaryl or aralkyl group, or substituted alkyl, aryl, aralkyl or 25 alkaryl, wherein these groups are as defined above.
The term “polyol”, as used herein, refers to a molecule that contains more than one hydroxyl group. A polyol may be a diol, triol, or a tetraol which contains 2, 3, and 4 hydroxyl groups, respectively. A polyol also may contain more than four hydroxyl groups, such as a pentaol, hexaol, heptaol, or the like, which contain, 5, 6, or 7 hydroxyl 30 groups, respectively. Additionally, a polyol also may be a sugar alcohol, polyhydric alcohol, or polyalcohol which is a reduced form of carbohydrate, wherein the carbonyl PCT/US2006/044574 WO 2007/061795 28 2015203721 02 Jul 2015 group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
Non-limiting examples of polyols in embodiments of this invention include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol 5 (glycerine), threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, reduced glucose syrup, and sugar alcohols or any other carbohydrates capable of being reduced which do not adversely affect the taste of the NHPS or the orally ingestible composition.
As used herein, the phrase “sweet taste improving additive” means any 10 material that imparts a more sugar-like temporal profile or sugar-like flavor profile or both to a NHPS. Suitable sweet taste improving additives useful in embodiments of this invention include amino acids and their salts, polyamino acids and their salts, peptides, sugar acids and their salts, nucleotides and their salts, organic acids, inorganic acids, organic salts including organic acid salts and organic base salts, inorganic acid salts (e.g., 15 sodium chloride, potassium chloride, magnesium chloride), bitter compounds, flavorants and flavoring ingredients, astringent compounds, polymers, proteins or protein hydrolysates, surfactants, emulsifiers, flavonoids, alcohols, and synthetic sweeteners.
Suitable sweet taste improving amino acid additives for use in embodiments of this invention include but are not limited to aspartic acid, arginine, glycine, glutamic 20 acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid (alpha-, beta-, or gamma- isomers), glutamine, hydroxyproline, taurine, norvaline, sarcosine, and their salt forms such as sodium or potassium salts or acid salts. The sweet taste improving amino acid additives also may be in the D- or L- configuration 25 and in the mono-, di-, or tri- form of the same or different amino acids. Additionally, the amino acids may be α-, β-, γ-, δ-, and ε-isomers if appropriate. Combinations of the foregoing amino acids and their corresponding salts (e.g., sodium, potassium, calcium, magnesium salts or other alkali or alkaline earth metal salts thereof, or acid salts) also are suitable sweet taste improving additives in embodiments of this invention. The amino 30 acids may be natural or synthetic. The amino acids also may be modified. Modified amino acids refers to any amino acid wherein at least one atom has been added, removed, substituted, or combinations thereof (e.g., N-alkyl amino acid, N-acyl amino acid, or N- PCT/US2006/044574 WO 2007/061795 29 2015203721 02 Jul 2015 methyl amino acid). Non-limiting examples of modified amino acids include amino acid derivatives such as trimethyl glycine, N-methyl-glycine, and N-methyl-alanine. As used herein, modified amino acids encompass both modified and unmodified amino acids. As used herein, amino acids also encompass both peptides and polypeptides (e.g., dipeptides, 5 tripeptides, tetrapeptides, and pentapeptides) such as glutathione and L-alanyl-L-glutamine.
Suitable sweet taste improving polyamino acid additives include poly-L-aspartic acid, poly-L-lysine (e.g., poly-L-a-lysine or poly-L-8-lysine), poly-L-omithine (e.g., poly-L-a-omithine or poly-L-s-ornithine), poly-L-arginine, other polymeric forms of 10 amino acids, and salt forms thereof (e.g., magnesium, calcium, potassium, or sodium salts such as L-glutamic acid mono sodium salt). The sweet taste improving polyamino acid additives also may be in the D- or L- configuration. Additionally, the polyamino acids may be α-, β-, γ-, δ-, and ε-isomers if appropriate. Combinations of the foregoing polyamino acids and their corresponding salts (e.g., sodium, potassium, calcium, 15 magnesium salts or other alkali or alkaline earth metal salts thereof or acid salts) also are suitable sweet taste improving additives in embodiments of this invention. The polyamino acids described herein also may comprise co-polymers of different amino acids. The polyamino acids may be natural or synthetic. The polyamino acids also may be modified such that at least one atom has been added, removed, substituted, or combinations thereof 20 (e.g., N-alkyl polyamino acid or N-acyl polyamino acid). As used herein, polyamino acids encompass both modified and unmodified polyamino acids. In accordance with particular embodiments of this invention, modified polyamino acids include, but are not limited to polyamino acids of various molecular weights (MW), such as poly-L-a-lysine with a MW of 1,500, MW of 6,000, MW of 25,200, MW of 63,000, MW of 83,000, or MW of 25 300,000.
Suitable sweet taste improving sugar acid additives for use in embodiments of this invention include, but are not limited to, aldonic, uronic, aldaric, alginic, gluconic, glucuronic, glucaric, galactaric, galacturonic, and their salts (e.g., sodium, potassium, calcium, magnesium salts or other physiologically acceptable salts), and combinations 30 thereof.
Suitable sweet taste improving nucleotide additives for use in embodiments of this invention include, but are not limited to, inosine monophosphate (“IMP”), PCT/IIS2006/044574 WO 2007/061795 2015203721 02M2015 30 guanosine monophosphate (“GMP”), adenosine monophosphate (“AMP”), cytosine monophosphate (CMP), uracil monophosphate (UMP), inosine diphosphate, guanosine diphosphate, adenosine diphosphate, cytosine diphosphate, uracil diphosphate, inosine triphosphate, guanosine triphosphate, adenosine triphosphate, cytosine triphosphate, uracil 5 triphosphate, and their alkali or alkaline earth metal salts, and combinations thereof. The nucleotides described herein also may comprise nucleotide-related additives, such as nucleosides or nucleic acid bases (e.g., guanine, cytosine, adenine, thymine, uracil).
Suitable sweet taste improving organic acid additives include any compound which comprises a -COOH moiety. Suitable sweet taste improving organic 10 acid additives for use in embodiments of this invention include, but are not limited to, C2-C30 carboxylic acids, substituted hydroxyl C1-C30 carboxylic acids, benzoic acid, substituted benzoic acids (e.g., 2,4-dihydroxybenzoic acid), substituted cinnamic acids, hydroxyacids, substituted hydroxybenzoic acids, substituted cyclohexyl carboxylic acids, tannic acid, lactic acid, tartaric acid, citric acid, gluconic acid, glucoheptonic acids, adipic 15 acid, hydroxycitric acid, malic acid, fruitaric acid (a blend of malic, fumaric, and tartaric acids), fumaric acid, maleic acid, succinic acid, chlorogenic acid, salicylic acid, creatine, glucono delta lactone, caffeic acid, bile acids, acetic acid, ascorbic acid, alginic acid, erythorbic acid, polyglutamic acid, and their alkali or alkaline earth metal salt derivatives thereof. In addition, the organic acid additives also may be in either the D- or L-20 configuration.
Suitable sweet taste improving organic acid additive salts include, but are not limited to, sodium, calcium, potassium, and magnesium salts of all organic acids, such as salts of citric acid, malic acid, tartaric acid, fumaric acid, lactic acid (e.g., sodium lactate), alginic acid (e.g., sodium alginate), ascorbic acid (e.g., sodium ascorbate), 25 benzoic acid (e.g., sodium benzoate or potassium benzoate), and adipic acid. The examples of the sweet taste improving organic acid additives described optionally may be substituted with one or more of the following moiety selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, halo, haloalkyl, carboxyl, acyl, acyloxy, amino, amido, carboxyl derivatives, alkylamino, dialkylamino, arylamino, alkoxy, aryloxy, nitro, cyano, 30 sulfo, thiol, imine, sulfonyl, sulfenyl, sulfinyl, sulfamyl, carboxalkoxy, carboxamido, phosphonyl, phosphinyl, phosphoryl, phosphino, thioester, thioether, anhydride, oximino, hydrazino, carbamyl, phospho, phosphonato, or any other viable functional group PCT/US2006/044574 WO 2007/061795 31 2015203721 02 Μ 2015 provided the substituted organic acid additives function to improve the sweet taste of a NHPS.
Suitable sweet taste improving inorganic acid additives for use in embodiments of this invention include, but are not limited to, phosphoric acid, 5 phosphorous acid, polyphosphoric acid, hydrochloric acid, sulfuric acid, carbonic acid, sodium dihydrogen phosphate, and their corresponding alkali or alkaline earth metal salts thereof (e.g., inositol hexaphosphate Mg/Ca).
Suitable sweet taste improving bitter compound additives for use in embodiments of this invention include, but are not limited to, caffeine, quinine, urea, bitter 10 orange oil, naringin, quassia, and salts thereof.
Suitable sweet taste improving flavorant and flavoring ingredient additives for use in embodiments of this invention include, but are not limited to, vanillin, vanilla extract, mango extract, cinnamon, citrus, coconut, ginger, viridiflorol, almond, menthol (including menthol without mint), grape skin extract, and grape seed extract. “Flavorant” 15 and “flavoring ingredient” are synonymous and can include natural or synthetic substances or combinations thereof. Flavorants also include any other substance which imparts flavor and may include natural or non-natural (synthetic) substances which are safe for human or animals when used in a generally accepted range. Non-limiting examples of proprietary flavorants include Dohler™ Natural Flavoring Sweetness Enhancer K14323 (Dohler™, 20 Darmstadt, Germany), Symrise™ Natural Flavor Mask for Sweeteners 161453 and 164126 (Symrise™, Holzminden, Germany), Natural Advantage™ Bitterness Blockers 1, 2, 9 and 10 (Natural Advantage™, Freehold, New Jersey, U.S.A.), and Sucramask™ (Creative Research Management, Stockton, California, U.S.A.).
Suitable sweet taste improving polymer additives for use in embodiments of 25 this invention include, but are not limited to, chitosan, pectin, pectic, pectinic, polyuronic, polygalacturonic acid, starch, food hydrocolloid or crude extracts thereof (e.g., gum acacia Senegal (Fibergum™), gum acacia seyal, carageenan), poly-L-lysine (e.g., poly-L-a-lysine or poly-L-s-lysine), poly-L-omithine (e.g., poly-L-a-omithine or poly-L-s-ornithine), polypropylene glycol, polyethylene glycol, poly(ethylene glycol methyl ether), 30 polyarginine, polyaspartic acid, polyglutamic acid, polyethylene imine, alginic acid, sodium alginate, propylene glycol alginate, and sodium polyethyleneglycolalginate, PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 32 sodium hexametaphosphate and its salts, and other cationic polymers and anionic polymers.
Suitable sweet taste improving protein or protein hydrolysate additives for use in embodiments of this invention include, but are not limited to, bovine serum albumin 5 (BSA), whey protein (including fractions or concentrates thereof such as 90% instant whey protein isolate, 34% whey protein, 50% hydrolyzed whey protein, and 80% whey protein concentrate), soluble rice protein, soy protein, protein isolates, protein hydrolysates, reaction products of protein hydrolysates, glycoproteins, and/or proteoglycans containing amino acids (e.g., glycine, alanine, serine, threonine, asparagine, 10 glutamine, arginine, valine, isoleucine, leucine, norvaline, methionine, proline, tyrosine, hydroxyproline, and the like), collagen (e.g., gelatin), partially hydrolyzed collagen (e.g., hydrolyzed fish collagen), and collagen hydrolysates (e.g., porcine collagen hydrolysate).
Suitable sweet taste improving surfactant additives for use in embodiments of this invention include, but are not limited to, polysorbates (e.g., polyoxyethylene 15 sorbitan monooleate (polysorbate 80), polysorbate 20, polysorbate 60), sodium dodecylbenzenesulfonate, dioctyl sulfosuccinate or dioctyl sulfosuccinate sodium, sodium dodecyl sulfate, cetylpyridinium chloride (hexadecylpyridinium chloride), hexadecyltrimethylammonium bromide, sodium cholate, carbamoyl, choline chloride, sodium glycocholate, sodium taurodeoxycholate, lauric arginate, sodium stearoyl lactylate, 20 sodium taurocholate, lecithins, sucrose oleate esters, sucrose stearate esters, sucrose palmitate esters, sucrose laurate esters, and other emulsifiers, and the like.
Suitable sweet taste improving flavonoid additives for use in embodiments of this invention generally are classified as flavonols, flavones, flavanones, flavan-3-ols, isoflavones, or anthocyanidins. Non-limiting examples of flavonoid additives include 25 catechins (e.g., green tea extracts such as Polyphenon™ 60, Polyphenon™ 30, and Polyphenon™ 25 (Mitsui Norin Co., Ltd., Japan), polyphenols, rutins (e.g., enzyme modified rutin Sanmelin™ AO (San-fi Gen F.F.I., Inc., Osaka, Japan)), neohesperidin, naringin, neohesperidin dihydrochalcone, and the like.
Suitable sweet taste improving alcohol additives for use in embodiments of 30 this invention include, but are not limited to, ethanol. PCT/US2006/044574 WO 2007/061795 33 2015203721 02 Μ 2015
Suitable sweet taste improving astringent compound additives include, but are not limited to, tannic acid, europium chloride (EuC13), gadolinium chloride (GdCl3), terbium chloride (TbCl3), alum, tannic acid, and polyphenols (e.g., tea polyphenols).
Suitable sweet taste improving vitamins include nicotinamide (Vitamin B3) 5 and pyridoxal hydrochloride (Vitamin B6).
Suitable sweet taste improving synthetic sweetener additives for use in embodiments of this invention include, but are not limited to, sucralose, acesulfame potassium or other salts, aspartame, alitame, saccharin, neohesperidin dihydrochalcone, cyclamate, neotame, N-[N-[3-(3-hydroxy-4-methOxyphenyl)propyl]-L-a-aspartyl]-L-10 phenylalanine 1-methyl ester, N-[N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-L-a-aspartyl)-L-phenylalanine 1-methyl ester, N-[N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-L-a-aspartyl]-L-phenylalanine 1-methyl ester, salts thereof, and the like, Specific embodiments of synthetic sweetener compositions comprising sweet taste improving compositions are disclosed in U.S, Provisional Application No. 60/739,124, entitled 15 “Synthetic Sweetener Compositions with Improved Temporal Profile and/or Flavor Profile, Methods for Their Formulation, and Uses,” filed on November 23, 2005, by DuBois, et al., the disclosure of which is incorporated herein by reference in its entirety.
The sweet taste improving compositions also may be in salt form which may be obtained using standard procedures well known in the art. The term “salt” also 20 refers to complexes that retain the desired chemical activity of the sweet taste improving compositions of the present invention and are safe for human or animal consumption in a generally acceptable range. Alkali metal (for example, sodium or potassium) or alkaline earth metal (for example calcium or magnesium) salts also can be made. Salts also may include combinations of alkali and alkaline earth metals. Non-limiting examples of such 25 salts are (a) acid addition salts formed with inorganic acids and salts formed with organic acids; (b) base addition salts formed with metal cations such as calcium, bismuth, barium, magnesium, aluminum, copper, cobalt, nickel, cadmium, sodium, potassium, and the like, or with a cation formed from ammonia, Ν,Ν-dibenzylethylenediamine, D-glucosamine, tetraethylammonium, or ethylenediamine; or (c) combinations of (a) and (b). Thus, any 30 salt forms which may be derived from the sweet taste improving compositions may be used with the embodiments of the present invention as long as the salts of the sweet taste improving additives do not adversely affect the taste of NHPSs or the orally ingestible PCT/US2006/044574 WO 2007/061795 34 2015203721 02 Μ 2015 compositions which comprises NHPSs. The salt forms of the additives can be added to the NHPS sweetener composition in the same amounts as their acid or base forms.
In particular embodiments, suitable sweet taste improving inorganic salt additives useful as sweet taste improving additives include but are not limited to sodium 5 chloride, potassium chloride, sodium sulfate, potassium citrate, europium chloride (EUCI3), gadolinium chloride (GdCl3), terbium chloride (TbCIs), magnesium sulfate, alum, magnesium chloride, magnesium phosphate, mono-, di-, tri-basic sodium or potassium salts of phosphoric acid (e.g., inorganic phosphates), salts of hydrochloric acid (e.g., inorganic chlorides), sodium carbonate, sodium bisulfate, and sodium bicarbonate. 10 Furthermore, in particular embodiments, suitable organic salts useful as sweet taste improving additives include but are not limited to choline chloride, alginic acid sodium salt (sodium alginate), glucoheptonic acid sodium salt, gluconic acid sodium salt (sodium gluconate), gluconic acid potassium salt (potassium gluconate), guanidine HC1, glucosamine HC1, monosodium glutamate (MSG), adenosine monophosphate salt, 15 amiloride HC1, magnesium gluconate, potassium tartrate (monohydrate), and sodium tartrate (dihydrate).
Embodiments of the sweet taste improving compositions of this invention can impart a more sharp and clean sensation to the taste of NHPSs. Furthermore, embodiments of the sweet taste improving compositions of the present invention have a 20 superior effect in improving the temporal profile and/or flavor profile of NHPSs while at the same time providing a sweetener composition with a low-caloric or non-caloric content, imparting more sugar-like characteristics. D. Temporal Profile Modulation
According to an embodiment of this invention, a NHPS composition 25 comprises at least one sweet taste improving composition present in the NHPS composition in an amount effective for the NHPS composition to impart an osmolarity of at least 10 mOsmoles/L to an aqueous solution of the NHPS composition wherein the NHPS is present in the aqueous solution in an amount sufficient to impart a maximum sweetness intensity equivalent to that of a 10% aqueous solution of sucrose by weight. As 30 used herein, “mOsmoles/L” refers to milliosmoles per liter. According to another embodiment, a NHPS composition comprises at least one sweet taste improving PCT/US2006/044574 WO 2007/061795 35 2015203721 02 Jul2015 composition in an amount effective for the NHPS composition to impart an osmolarity of 10 to 500 mOsmoles/L, preferably 25 to 500 mOsmoles/L preferably, more preferably 100 to 500 mOsmoles/L, more preferably 200 to 500 mOsmoles/L, and. still more preferably 300 to 500 mOsmoles/L to an aqueous solution of the NHPS composition wherein the 5 NHPS is present in the aqueous solution in an amount sufficient to impart a maximum sweetness intensity equivalent to that of a 10% aqueous solution of sucrose by weight. In particular embodiments, a plurality of sweet taste improving compositions may be combined with a NHPS, and in that case, the osmolarity imparted is that of the total combination of the plurality of sweet taste improving compositions. 10 Osmolarity refers to the measure of osmoles of solute per liter of solution, wherein osmole is equal to the number of moles of osmotically active particles in an ideal solution (e.g., a mole of glucose is one osmole), whereas a mole of sodium chloride is two osmoles (one mole of sodium and one mole of chloride). Thus, in order to improve in the quality of taste of NHPSs, the osmotically active compounds or the compounds which 15 impart osmolarity must not introduce significant off taste to the formulation.
In one embodiment, suitable sweet taste improving compositions which improve the temporal profile of the natural high-potency sweetener or sweetenable composition to be more sugar-like include carbohydrates, polyols, amino acids, other sweet taste improving additives (e.g., sugar acids and their salts, nucleotides, organic 20 acids, inorganic acids, organic salts including organic acid salts and organic base salts, inorganic salts, bitter compounds, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, flavonoids, alcohols, and synthetic sweeteners).
In more preferred embodiments, non-limiting examples of suitable compounds which impart osmolarity include sweet taste improving carbohydrate 25 additives, sweet taste improving polyol additives, sweet taste improving alcohol additives, sweet taste improving inorganic acid additives, sweet taste improving organic acid additives, sweet taste improving inorganic salt additives, sweet taste improving organic salt additives, sweet taste improving organic base salt additives, sweet taste improving amino acid additives, sweet taste improving amino acid salt additives, sweet taste 30 improving bitter additives, and sweet taste improving astringent additives. In one embodiment, suitable compounds which impart osmolarity include, but are not limited to, sucrose, fructose, glucose, maltose, lactose, mannose, galactose, tagatose, erythritol, PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 36 glycerol, propylene glycol, ethanol, phosphoric acid (including corresponding sodium, potassium, and magnesium salts thereof), citric acid, malic acid, tartaric acid, fumaric acid, gluconic acid, adipic acid, glucosamine and glucosamine salt, choline salt, guanidine salt, protein or protein hydrolysate, glycine, alanine, serine, threonine, theanine, caffeine, 5 quinine, urea, naringin, tannic acid, AlNa(S04)2, A1K(S04>2 and other forms of alum, and combinations thereof.
In one embodiment, suitable sweet taste improving carbohydrate additives for the present invention have a molecular weight less than or equal to 500 and desirably have a molecular weight from 50 to 500. In particular embodiments, suitable 10 carbohydrates with a molecular weight less than or equal to 500 include but are not limited to sucrose, fructose, glucose, maltose, lactose, mannose, galactose, and tagatose. Generally, in accordance with desirable embodiments of this invention, a carbohydrate is present in the NHPS compositions in an amount from about 1,000 to about 100,000 ppm. (Throughout this specification, the term ppm means parts per million by weight or volume. 15 For example, 500 ppm means 500 mg in a liter.) In accordance with other desirable embodiments of this invention, a carbohydrate is present in the NHPS sweetened compositions in an amount from about 2,500 to about 10,000 ppm. In another embodiment, suitable sweet taste improving carbohydrate additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a 20 sweetenable composition include, but are not limited to sweet taste improving carbohydrate additives with a molecular weight ranging from about 50 to about 500.
In one embodiment, suitable polyol have a molecular weight less than or equal to 500 and desirably have a molecular weight from 76 to 500. In particular embodiments, suitable polyols with a molecular weight less than or equal to 500 include 25 but are not limited to erythritol, glycerol, and propylene glycol. Generally, in accordance with desirable embodiments of this invention, a polyol is present in the NHPS compositions in an amount from about 100 ppm to about 80,000 ppm. In accordance with other desirable embodiments of this invention, a polyol is present in the NHPS sweetened compositions in an amount from about 400 to about 80,000 ppm. In other embodiments of 30 this invention, a polyol is present in NHPS sweetened compositions in an amount from about 5,000 to about 40,000 ppm of the composition, more particularly from about 10,000 to about 35,000 ppm of the composition. Desirably, the at least one NHPS and at least one PCT/US2006/044574 WO 2007/061795 37 2015203721 02 Μ 2015 sweet taste improving polyol are present in the sweetener composition in a ratio from about 1:4 to about 1:800, respectively; more particularly from about 1:20 to about 1:600; even more particularly from about 1:50 to about 1:300; and still more particularly from about 1:75 to about 1:150. In a sub-embodiment, suitable sweet taste improving polyol 5 additives for imparting osmolalities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to sweet taste improving polyol additives with a molecular weight ranging from about 76 to about 500.
Generally, in accordance with another embodiment of this invention, a suitable sweet taste improving alcohol is present in the NHPS compositions in an amount 10 from about 625 to about 10,000 ppm. In another embodiment, suitable sweet taste improving alcohol additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to sweet taste improving alcohol additives with a molecular weight ranging from about 46 to about 500. A non-limiting example of sweet taste improving alcohol additive 15 with a molecular weight ranging from about 46 to about 500 includes ethanol.
In one embodiment, suitable sweet taste improving amino acid additives have a molecular weight of less than or equal to 250 and desirably have a molecular weight from 75 to 250. In particular embodiments, suitable sweet taste improving amino acid additives with a molecular weight less than or equal to 250 include but are not limited 20 to glycine, alanine, serine, valine, leucine, isoleucine, proline, theanine, and threonine. Preferred amino acids include those which are sweet tasting at high concentrations, but are desirably present in embodiments of this invention at amounts below or above their sweetness taste detection threshold. Even more preferred are mixtures of amino acids at amounts below or above their sweetness taste detection threshold. Generally, in 25 accordance with desirable embodiments of this invention, a sweet taste improving amino acid additive is present in the NHPS compositions in an amount from about 100 ppm to about 25,000 ppm, more particularly from about 1,000 to about 10,000 ppm, and still more particularly from about 2,500 to about 5,000 ppm. In accordance with other desirable embodiments of this invention, a sweet taste improving amino acid additive is present in 30 the NHPS sweetened compositions in an amount from about 250 ppm to about 7,500 ppm. In a sub-embodiment, suitable sweet taste improving amino acid additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a PCT/US2006/044574 WO 2007/061795 2015203721 02M2015 38 sweetenable composition include, but are not limited to sweet taste improving amino acid additives with a molecular weight ranging from about 75 to about 250.
Generally, in accordance with yet another embodiment of this invention, a suitable sweet taste improving amino acid salt additive is present in the NHPS 5 compositions in an amount from about 25 to about 10,000 ppm more particularly from about 1,000 to about 7,500 ppm, and still more particularly from about 2,500 to about 5,000 ppm. In another embodiment, suitable sweet taste improving amino acid salt additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to, sweet taste 10 improving amino acid additives with a molecular weight ranging from about 75 to about 300. Non-limiting examples of sweet taste improving amino acid salt additives with a molecular weight ranging from about 75 to about 300 include salts of glycine, alanine, serine, theanine, and threonine.
Generally, in accordance with still another embodiment of this invention, a 15 suitable sweet taste improving protein or protein hydroyslate additive is present in the NHPS compositions in an amount from about 200 to about 50,000 ppm. In another embodiment, suitable sweet taste improving protein or protein hydrolysate additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to, sweet taste improving protein or 20 protein hydrolysate additives with a molecular weight ranging from about 75 to about 300. Non-limiting examples of sweet taste improving protein or protein hydrolysate additives with a molecular weight ranging from about 75 to about 300 include proteins or protein hydrolysates containing glycine, alanine, serine, and threonine.
Generally, in accordance with another embodiment of this invention, a 25 suitable sweet taste improving inorganic acid additive is present in the NHPS compositions in an amount from about 25 to about 5,000 ppm. In another embodiment, suitable sweet taste improving inorganic acid additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to phosphoric acid, HC1, and H2SO4 and any other inorganic 30 acid additives which are safe for human or animal consumption when used in a generally acceptable range. In a sub-embodiment, suitable suitable sweet taste improving inorganic acid additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 PCT/US2006/044574 WO 2007/061795 39 2015203721 02 Jul 2015 mOsmoles/L to a sweetenable composition include but are not limited to sweet taste improving inorganic acid additives with a molecular weight range from about 36 to about 98.
Generally, in accordance with still another embodiment of this invention, a 5 suitable sweet taste improving inorganic acid salt additive is present in the NHPS compositions in an amount from about 25 to about 5,000 ppm. In another embodiment, suitable sweet taste improving inorganic acid salt additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to salts of inorganic acids, for example sodium, 10 potassium, calcium, and magnesium salts of phosphoric acid, and any other alkali or alkaline earth metal salts of other inorganic acid additives (e.g., sodium bisulfate) which are safe for human or animal consumption when used in a generally acceptable range. In a particular embodiment, suitable sweet taste improving inorganic acid salt additives include magnesium chloride, magnesium sulfate, sodium chloride, or combinations thereof. In a 15 sub-embodiment, suitable suitable sweet taste improving inorganic acid salt additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to, sweet taste improving inorganic acid salt additives with a molecular weight range from about 58 to about 120.
Generally, in accordance with still another embodiment of this invention, a 20 suitable sweet taste improving organic acid additive is present in the NHPS compositions in an amount from about 10 to about 5,000 ppm. In another embodiment, suitable sweet taste improving organic acid additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to, creatine, citric acid, malic acid, succinic acid, hydroxycitric acid, tartaric acid, 25 fumaric acid, gluconic acid, glutaric acid, adipic acid, and any other sweet taste improving organic acid additives which are safe for human or animal consumption when used in a generally acceptable range. In one embodiment, the sweet taste improving organic acid additive comprises a molecular weight range from about 60 to about 208.
Generally, in accordance with still another embodiment of this invention, a 30 suitable sweet taste improving organic acid salt additive is present in the NHPS compositions in an amount from about 20 to about 10,000 ppm. In another embodiment, suitable sweet taste improving organic acid salt additives for imparting osmolarities WO 2007/061795 PCT/US2006/044574 40 2015203721 02 Μ 2015 ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to, salts of the sweet taste improving organic acid additive, such as sodium, potassium, calcium, magnesium, and other alkali or alkaline metal salts of citric acid, malic acid, tartaric acid, fumaric acid, gluconic acid, adipic acid, 5 hydroxycitric acid, succinic acid, glutaric acid, and salts of any other sweet taste improving organic acid additives which are safe for human or animal consumption when used in a generally acceptable range. In one embodiment, the sweet taste improving organic acid salt additive comprises a molecular weight range from about 140 to about 208. 10 Generally, in accordance with yet another embodiment of this invention, a suitable sweet taste improving organic base salt additive is present in the NHPS compositions in an amount from about 10 to about 5,000 ppm. In another embodiment, suitable sweet taste improving organic base salt additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable 15 composition include, but are not limited to, inorganic and organic acid salts of organic bases such as glucosamine salts, choline salts, and guanidine salts.
Generally, in accordance with yet another embodiment of this invention, a suitable sweet taste improving astringent additive is present in the NHPS compositions in an amount from about 25 to about 1,000 ppm. In another embodiment, suitable sweet 20 taste improving astringent additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to, tannic acid, tea polyphenols, catechins, aluminum sulfate, AlNa(SC>4)2, A1K(SC>4)2 and other forms of alum.
Generally, in accordance with yet another embodiment of this invention, a 25 suitable sweet taste improving nucleotide additive is present in the NHPS compositions in an amount from about 5 to about 1,000 ppm. In another embodiment, suitable sweet taste improving nucleotide additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to, adenosine monophosphate. 30 Generally, in accordance with yet another embodiment of this invention, a
suitable sweet taste improving polyamino acid additive is present in the NHPS PCT/US2006/044574 WO 2007/061795 41 2015203721 02 Μ 2015 compositions in an amount from about 30 to about 2,000 ppm. In another embodiment, suitable sweet taste improving polyamino acid additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to, poly-L-lysine (e.g., poly-L-a-lysine or poly-L-5 ε-lysine), poly-L-omithine (e.g., poly-L-a-omithine or poly-L-s-ornithine), and poly-L-arginine.
Generally, in accordance with yet another embodiment of this invention, a suitable sweet taste improving polymer additive is present in the NHPS compositions in an amount from about 30 to about 2,000 ppm. In another embodiment, suitable sweet taste 10 improving polymer additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to, chitosan, pectin, hydrocolloids such as gum acacia Senegal, propylene glycol, polyethylene glycol, and polyethylene glycol methyl ether).
Generally, in accordance with yet another embodiment of this invention, a 15 suitable sweet taste improving surfactant additive is present in the NHPS compositions in an amount from about 1 to about 5,000 ppm. In another embodiment, suitable sweet taste improving surfactant additives for imparting osmolarities ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to, polysorbates, choline chloride, sodium taurocholate, lecithins, sucrose oleate 20 esters, sucrose stearate esters, sucrose palmitate esters, and sucrlose laurate esters.
Generally, in accordance with yet another embodiment of this invention, a suitable sweet taste improving flavonoid additive is present in the NHPS compositions in an amount from about 0.1 to about 1,000 ppm. In another embodiment, suitable sweet taste improving flavonoid additives for imparting osmolarities ranging from about 10 25 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition include, but are not limited to, naringin, catechins, rutins, neohesperidin, and neohesperidin dihydrochalcone. E. Flavor Profile Modulation
As hypothesized above, flavor profile imparts a sugar-like characteristic to NHPS. In one embodiment, any sweet taste improving composition that imparts a sugar-30 like flavor profile to a NHPS will be effective by this mechanism. In particular, any sweet taste improving composition that imparts a more sugar-like osmotic taste will be effective PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 42 by this mechanism. In one embodiment, suitable sweet taste improving compositions which improve the flavor profile, including the osmotic taste, of the natural high-potency sweetener or sweetenable composition to be more sugar-like include carbohydrates, polyols, amino acid, and other sweet taste improving additives (e.g., polyamino acids, 5 peptides, sugar acids and their salts, nucleotides, organic acids, inorganic acids, organic salts including organic acid salts and organic base salts, inorganic salts, bitter compounds, flavorants and flavoring ingredients, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, flavonoids, alcohols, and synthetic sweeteners).
In a preferred embodiment, non-limiting examples of sweet taste improving 10 compositions enhancing a NHPS’s osmotic taste to be more sugar-like include sweet taste improving carbohydrate additives, sweet taste improving alcohol additives, sweet taste improving polyol additives, sweet taste improving amino acid additives, sweet taste improving amino acid salt additives, sweet taste improving inorganic add salt additives, sweet taste improving polymer additives, and sweet taste improving protein or protein 15 hydrolysate additives.
In another embodiment, suitable sweet improving amino acid additives include amino acids comprising a molecular weight less than or equal to 250. In one example, suitable sweet taste improving amino acids include, but are not limited to, low molecular weight amino acids such as glycine, leucine, valine, isoleucine, proline, 20 hydroxyproline, alanine, serine, theanine, and threonine.
In another embodiment, suitable sweet taste improving carbohydrate additives for improving the osmotic taste of the NHPS to be more sugar-like include, but are not limited to, sweet taste improving carbohydrate additives with a molecular weight ranging from about 50 to about 500. Non-limiting examples of sweet taste improving 25 carbohydrate additives with a molecular weight ranging from about 50 to about 500 include sucrose, fructose, glucose, maltose, lactose, mannose, galactose, ribose, rhamnose, trehalose, and tagatose.
In another embodiment, suitable sweet taste improving polyol additives for improving the osmotic taste of the NHPS to be more sugar-like include, but are not limited 30 to, sweet taste improving polyol additives with a molecular weight ranging from about 76 to about 500. Non-limiting examples of sweet taste improving polyol additives with a WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 43 molecular weight ranging from about 76 to about 500 include erythritol, glycerol, and propylene glycol. In a sub-embodiment, other suitable sweet taste improving polyol additives include sugar alcohols.
In another embodiment, suitable sweet taste improving alcohol additives for 5 improving the osmotic taste of the NHPS to be more sugar-like include, but are not limited to, sweet taste improving alcohol additives with a molecular weight ranging from about 46 to about 500. A non-limiting example of sweet taste improving alcohol additive with a molecular weight ranging from about 46 to about 500 includes ethanol.
In another embodiment, suitable sweet taste improving amino acid additives 10 for improving the osmotic taste of the NHPS to be more sugar-like include, but are not limited to, sweet taste improving amino acid additives with a molecular weight ranging from about 75 to about 250. Non-limiting examples of sweet taste improving amino acid additives with a molecular weight ranging from about 75 to about 250 include glycine, alanine, serine, leucine, valine, isoleucine, proline, hydroxyproline, glutamine, theanine, 15 and threonine.
In another embodiment, suitable sweet taste improving amino acid salt additives for improving the osmotic taste of the NHPS to be more sugar-like include, but are not limited to, sweet taste improving amino acid salt additives with a molecular weight ranging from about 75 to about 300. Non-limiting examples of sweet taste improving 20 amino acid salt additives with a molecular weight ranging from about 75 to about 300 include salts of glycine, alanine, serine, , leucine, valine, isoleucine, proline, hydroxyproline, glutamine, theanine, and threonine.
In another embodiment, suitable sweet taste improving protein or protein hydrolysate additives for improving the osmotic taste of the NHPS to be more sugar-like 25 include, but are not limited to, sweet taste improving protein or protein hydrolysate additives with a molecular weight ranging from about 75 to about 300. Non-limiting examples of sweet taste improving protein or protein hydrolysate additives with a molecular weight ranging from about 75 to about 300 include protein or protein hydrolysates containing glycine, alanine, serine, leucine, valine, isoleucine, proline, 30 hydroxyproline, glutamine, and threonine. WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 44
In another embodiment, suitable sweet taste improving inorganic acid salt additives for improving the osmotic taste of the NHPS to be more sugar-like include, but are not limited to, sodium chloride, potassium chloride, magnesium chloride, KH2PO4 and NaH2P04. Suitable sweet taste improving inorganic acid salt additives for improving the 5 osmotic taste may comprise a molecular weight from about 58 to about 120.
In another embodiment, suitable sweet taste improving bitter additives for improving the osmotic taste of the NHPS to be more sugar-like include, but are not limited to, caffeine, quinine, urea, quassia, tannic acid, and naringin.
In a further embodiment, the sweet taste improving compositions improve 10 the NHPS taste to be similar to that of sucrose by at least one mechanism selected from temporal profile (e.g., sweetness onset or sweetness linger), maximal response, flavor profile (e.g., osmotic taste), adaptation behavior, and flavor profile. In a sub-embodiment, the sweet taste improving compositions improve the NHPS taste to be similar to that of sucrose by at least one mechanism selected from temporal profile, maximal response, 15 flavor profile, adaptation behavior, and flavor profile, and optionally impart a masking effect to suppress, reduce, or eliminate the undesirable taste of the NHPS and/or impart sugar-like characteristics to the NHPS. F. Combinations of NHPSs and Sweet Taste Improving Compositions
It has been discovered that combinations of at least one NHPS and at least 20 one sweet taste improving composition improve the temporal profile and/or flavor profile, including the osmotic taste, to be more sugar-like. One of ordinary skill in the art, with the teachings of the present invention, may arrive at all the possible combinations of the NHPS and sweet taste improving compositions. For example, non-limiting combinations of the NHPS and sweet taste improving compositions include: 25 30 1. at least one NHPS and at least one carbohydrate; 2. at least one NHPS and at least one polyol; 3. at least one NHPS and at least one amino acid; 4. at least one NHPS and at least one other sweet taste improving additive; 5. at least one NHPS, at least one carbohydrate, at least one polyol, at least one amino acid, and at least one other sweet taste improving additive; at least one NHPS, at least one carbohydrate, and at least one polyol; 6. PCT/US2006/044574 WO 2007/061795 2015203721 02M2015 45 7. at least one NHPS, at least one carbohydrate, and at least one amino acid; 8. at least one NHPS, at least one carbohydrate, and at least one other sweet taste improving additive; 9. at least one NHPS, at least one polyol, and at least one amino acid; 5 10. at least one NHPS, at least one polyol, and at least one other sweet taste improving additive; 11. at least one NHPS, at least one amino acid, and at least one other sweet taste improving additive 12. at least one NHPS, at least one carbohydrate, at least one polyol, and at 10 least one amino acid; 13. at least one NHPS, at least one carbohydrate, at least one polyol, and at least one other sweet taste improving additive; 14. at least one NHPS, at least one polyol, at least one amino acid, and at least one other sweet taste improving additive; and 15 15. at least one NHPS, at least one carbohydrate, at least one amino acid, and at least one other sweet taste improving additive.
These fifteen major combinations further may be broken down into further combinations in order to improve the overall taste of the NHPS or the orally ingestible compositions comprising a NHPS. 20 1. Combinations of NHPSs A single NHPS may be combined with at least one sweet taste improving composition or a plurality of NHPSs may be combined with at least one sweet taste improving composition. Likewise, the sweet taste improving composition can include combinations of the foregoing identified polyols, carbohydrates, amino acids, other sweet 25 taste improving additives, and combinations thereof. Multiple NHPSs can be combined as long as the combined effect does not adversely affect the taste of the NHPS in combination with the sweet taste improving compositions or the taste of the orally ingestible compositions comprising NHPSs. Furthermore, multiple NHPSs can be combined to offset undesirable tastes of the individual NHPSs in the combination. 30 PCT/US2006/044574 WO 2007/061795 46 2. Combinations of Sweet Taste Improving Compositions
As explained above, the sweet taste improving composition is selected from the group consisting of polyols, carbohydrates, amino acids, other sweet taste improving additives, and combinations thereof. The other sweet taste improving additives useful in embodiments of this invention are described herein above. In one embodiment, a single sweet taste improving composition may be used with a single NHPS. In another embodiment of the present invention, a single sweet taste improving composition may be used with one or more NHPSs. In yet another embodiment, one or more sweet taste improving compositions may be used with a single NHPS. In a further embodiment, there may be a plurality of sweet taste improving compositions used in combination with one or more NHPSs. Thus, non-limiting examples of sweet taste improving composition combinations for embodiments of this invention include: i. at least one polyol, at least one carbohydrate, at least one amino add, and at least one other sweet taste improving additive; ii. at least one polyol, at least one carbohydrate, and at least one other sweet taste improving additive; iii. at least one polyol and at least one other sweet taste improving additive; iv. at least one polyol and at least one carbohydrate; v. at least one carbohydrate and at least one other sweet taste improving additive; vi. at least one polyol and at least one amino acid; vii. at least one carbohydrate and at least one amino acid; viii. at least one amino acid and at least one other sweet taste improving additive.
Other sweet taste improving composition combinations in accordance with embodiments of this invention include: 1. at least one polyol, at least one carbohydrate, and at least one amino acid; 2. at least one polyol, at least one carbohydrate, and at least one polyamino acid; 3. at least one polyol, at least one carbohydrate, and at least one sugar acid; 4. at least one polyol, at least one carbohydrate, and at least one nucleotide; 5. at least one polyol, at least one carbohydrate, and at least one organic acid; WO 2007/061795 PCT/US2006/044574 47 2015203721 02 Jul2015 10 20 25 30 6. at least one polyol, at least one carbohydrate, and at least one inorganic acid; 7. . at least one polyol, at least one carbohydrate, and at least one bitter compound; 8. at least one polyol, at least one carbohydrate, and at least one flavorant or flavoring ingredient; 9. at least one polyol, at least one carbohydrate, and at least one polymer; 10. at least one polyol, at least one carbohydrate, and at least one protein or protein hydrolysate or protein hydrolysate with low molecular weight amino acid; 11. at least one polyol, at least one carbohydrate, and at least one surfactant; 12. at least one polyol, at least one carbohydrate, and at least one flavonoid; 13. at least one polyol, at least one carbohydrate, and at least one alcohol; 14. at least one polyol, at least one carbohydrate, and at least one emulsifier; 15. at least one polyol, at least one carbohydrate, and at least one inorganic salt, 16. at least one polyol, at least one carbohydrate, and at least one organic salt, 17. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one other sweet taste improving additive; 18. at least one polyol, at least one carbohydrate, at least one polyamino acid, and at least one other sweet taste improving additive; 19. at least one polyol, at least one carbohydrate, at least one sugar acid, and at least one other sweet taste improving additive; 20. at least one polyol, at least one carbohydrate, at least one nucleotide, and at least one other sweet taste improving additive; 21. at least one polyol, at least one carbohydrate, at least one organic acid, and at least one other sweet taste improving additive; 22. at least one polyol, at least one carbohydrate, at least one inorganic acid, and at least one other sweet taste improving additive; 23. at least one polyol, at least one carbohydrate, at least one bitter compound, and at least one other sweet taste improving additive; 24. at least one polyol, at least one carbohydrate, at least one flavorant or flavoring ingredient, and at least one other sweet taste improving additive; 25. at least one polyol, at least one carbohydrate, at least one polymer, and at least one other sweet taste improving additive; WO 2007/061795 PCT/US2006/044574 48 2015203721 02 Μ 2015 5 10 15 20 25 30 26. at least one polyol, at least one carbohydrate, at least one protein or protein hydrolysate, and at least one other sweet taste improving additive; 27. at least one polyol, at least one carbohydrate, at least one surfactant, and at least one other sweet taste improving additive; 28. at least one polyol, at least one carbohydrate, at least one flavonoid, and at least one other sweet taste improving additive; 29. at least one polyol, at least one carbohydrate, at least one alcohol, and at least one other sweet taste improving additive; 30. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one polyamino acid; 31. at least one polyol, at least one carbohydrate, at least one amino acid, at least one polyamino acid, and at least one sugar acid; 32. at least one polyol, at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, and at least one nucleotide; 33. at least one polyol, at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, and at least one organic acid; 34. at least one polyol, at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, and at least one inorganic acid; 35. at least one polyol, at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, and at least one bitter compound; 36. at least one polyol, at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, and at least one polymer; 37. at least one polyol, at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, and at least one protein or protein hydrolysate; PCT/US2006/044574 WO 2007/061795 49 38. at least one polyol, at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, at least one protein or protein hydrolysate, and at least one surfactant; 39. at least one polyol, at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, at least one protein or protein hydrolysate, at least one surfactant, and at least one flavonoid; 40. at least one polyol, at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, at least one protein or protein hydrolysate, at least one surfactant, at least one flavonoid, and at least one alcohol; 41. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one sugar acid; 42. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one nucleotide; 43. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one organic acid; 44. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one inorganic acid; 45. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one bitter compound; 46. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one polymer; 47. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one protein or protein hydrolysate; 48. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one surfactant; WO 2007/061795 PCT/US2006/044574 2015203721 02 Μ 2015 50 49. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one flavonoid; 50. at least one polyol, at least one carbohydrate, at least one amino acid, and at least one alcohol; 5 51. at least one polyol, at least one carbohydrate, at least one polyamino acid, and at least one sugar acid; 52. at least one polyol, at least one carbohydrate, at least one polyamino acid, and at least one nucleotide; 53. at least one polyol, at least one carbohydrate, at least one polyamino acid, and 10 at least one organic acid; 54. at least one polyol, at least one carbohydrate, at least one polyamino acid, and at least one inorganic acid; 55. at least one polyol, at least one carbohydrate, at least one polyamino acid, and at least one bitter compound; 15 56. at least one polyol, at least one carbohydrate, at least one polyamino acid, and at least one polymer; 57. at least one polyol, at least one carbohydrate, at least one polyamino acid, and at least one protein or protein hydrolysate; 58. at least one polyol, at least one carbohydrate, at least one polyamino acid, and 20 at least one surfactant; 59. at least one polyol, at least one carbohydrate, at least one polyamino acid, and at least one flavonoid; 60. at least one polyol, at least one carbohydrate, at least one polyamino acid, and at least one alcohol; 25 61. at least one polyol, at least one carbohydrate, at least one sugar acid, and at least one nucleotide; 62. at least one polyol, at least one carbohydrate, at least one sugar acid, and at least one organic acid; 63. at least one polyol, at least one carbohydrate, at least one sugar acid, and at 30 least one inorganic acid; 64. at least one polyol, at least one carbohydrate, at least one sugar acid, and at least one bitter compound; WO 2007/061795 PCT/US2006/044574 2015203721 02 Jul2015 51 65. at least one polyol, at least one carbohydrate, at least one sugar acid, and at least one polymer; 66. at least one polyol, at least one carbohydrate, at least one sugar acid, and at least one protein or protein hydrolysate; 5 67. at least one polyol, at least one carbohydrate, at least one sugar acid, and at least one surfactant; 68. at least one polyol, at least one carbohydrate, at least one sugar acid, and at least one flavonoid; 69. at least one polyol, at least one carbohydrate, at least one sugar acid, and at 10 least one alcohol; 70. at least one polyol, at least one carbohydrate, at least one nucleotide, and at least one organic acid; 71. at least one polyol, at least one carbohydrate, at least one nucleotide, and at least one inorganic acid; 15 72. at least one polyol, at least one carbohydrate, at least one nucleotide, and at least one bitter compound; 73. at least one polyol, at least one carbohydrate, at least one nucleotide, and at least one polymer; 74. at least one polyol, at least one carbohydrate, at least one nucleotide, and at 20 least one protein or protein hydrolysate; 75. at least one polyol, at least one carbohydrate, at least one nucleotide, and at least one surfactant; 76. at least one polyol, at least one carbohydrate, at least one nucleotide, and at least one flavonoid; 25 77. at least one polyol, at least one carbohydrate, at least one nucleotide, and at least one alcohol; 78. at least one polyol, at least one carbohydrate, at least one organic acid, and at least one inorganic acid; 79. at least one polyol, at least one carbohydrate, at least one organic acid, and at 30 least one bitter compound; 80. at least one polyol, at least one carbohydrate, at least one organic acid, and at least one polymer; WO 2007/061795 PCT/US2006/044574 52 2015203721 02 Μ 2015 10 20 25 30 81. at least one polyol, at least one carbohydrate, at least one organic acid, and at least one protein or protein hydrolysate; 82. at least one polyol, at least one carbohydrate, at least one organic acid, and at least one surfactant; 83. at least one polyol, at least one carbohydrate, at least one organic acid, and at least one flavonoid; 84. at least one polyol, at least one carbohydrate, at least one organic acid, and at least one alcohol; 85. at least one polyol, at least one carbohydrate, at least one inorganic acid, and at least one bitter compound; 86. at least one polyol, at least one carbohydrate, at least one inorganic acid, and at least one polymer; 87. at least one polyol, at least one carbohydrate, at least one inorganic acid, and at least one protein or protein hydrolysate; 88. at least one polyol, at least one carbohydrate, at least one inorganic acid, and at least one surfactant; 89. at least one polyol, at least one carbohydrate, at least one inorganic acid, and at least one flavonoid; 90. at least one polyol, at least one carbohydrate, at least one inorganic acid, and at least one alcohol; 91. at least one polyol, at least one carbohydrate, at least one bitter compound, and at least one polymer; 92. at least one polyol, at least one carbohydrate, at least one bitter compound, and at least one protein or protein hydrolysate; 93. at least one polyol, at least one carbohydrate, at least one bitter compound, and at least one surfactant; 94. at least one polyol, at least one carbohydrate, at least one bitter compound, and at least one flavonoid; 95. at least one polyol, at least one carbohydrate, at least one bitter compound, and at least one alcohol; 96. at least one polyol, at least one carbohydrate, at least one polymer, and at least one protein or protein hydrolysate; 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 53 97. at least one polyol, at least one carbohydrate, at least one polymer, and at least one surfactant; 98. at least one polyol, at least one carbohydrate, at least one polymer, and at least one flavonoid; 5 99. at least one polyol, at least one carbohydrate, at least one polymer, and at least one alcohol; 100. at least one polyol, at least one carbohydrate, at least one protein or protein hydrolysate, and at least one surfactant; 101. at least one polyol, at least one carbohydrate, at least one protein or protein 10 hydrolysate, and at least one flavonoid; 102. at least one polyol, at least one carbohydrate, at least one surfactant, and at least one flavonoid; 103. at least one polyol, at least one carbohydrate, at least one surfactant, and at least one alcohol; and 15 104. at least one polyol, at least one carbohydrate, at least one flavonoid, and at least one alcohol. Other sweet taste improving composition combinations in accordance with embodiments of this invention include: 1. at least one polyol and at least one amino acid; 20 2. at least one polyol and at least one polyamino acid; 3., at least one polyol and at least one sugar acid; 4. at least one polyol and at least one nucleotide; 5. at least one polyol and at least one organic acid; 6. at least one polyol and at least one inorganic acid; 25 7. at least one polyol and at least one bitter compound; 8. at least one polyol and at least one flavorant or flavoring ingredient; 9. at least one polyol and at least one polymer; 10. at least one polyol and at least one protein or protein hydrolysate; 11. at least one polyol and at least one surfactant; 30 12. at least one polyol and at least one flavonoid; 13. at least one polyol and at least one alcohol; 14. at least one polyol and at least one emulsifier; WO 2007/061795 PCT/US2006/044574 2015203721 02 Μ 2015 54 10 20 25 30 15. at least one polyol and at least one inorganic salt; 16. at least one polyol and at least one organic salt; 17.. at least one polyol and at least one protein or protein hydrolysate or mixture of low molecular weight amino acids; 18. at least one polyol, at least one amino acid, and at least one other sweet taste improving additive; 19. at least one polyol, at least one polyamino acid, and at least one other sweet taste improving additive; 20. at least one polyol, at least one sugar acid, and at least one other sweet taste improving additive; 21. at least one polyol, at least one nucleotide, and at least one other sweet taste improving additive; 22. at least one polyol, at least one organic acid, and at least one other sweet taste improving additive; 23. at least one polyol, at least one inorganic acid, and at least one other sweet taste improving additive; 24. at least one polyol, at least one bitter compound, and at least one other sweet taste improving additive; 25. at least one polyol, at least one flavorant or flavoring ingredient, and at least one other sweet taste improving additive; 26. at least one polyol, at least one polymer, and at least one other sweet taste improving additive; 27. at least one polyol, at least one protein or protein hydrolysate, and at least one other sweet taste improving additive; 28. at least one polyol, at least one surfactant, and at least one other sweet taste improving additive; 29. at least one polyol, at least one flavonoid, and at least one other sweet taste improving additive; 30. at least one polyol, at least one alcohol, and at least one other sweet taste improving additive; 31. at least one polyol, at least one amino acid, and at least one polyamino acid; WO 2007/061795 PCT/US2006/044574 2015203721 02 Jul2015 55 5 10 15 20 25 30 32. at least one polyol, at least one amino acid, at least one polyamino acid, and at least one sugar acid; 33. at least one polyol, at least one amino acid, at least one polyamino acid, at least one sugar acid, and at least one nucleotide; 34. at least one polyol, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, and at least one organic acid; 35. at least one polyol, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, and at least one inorganic acid; 36. at least one polyol, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, and at least one bitter compound; 37. at least one polyol, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, and at least one polymer; 38. at least one polyol, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, and at least one protein or protein hydrolysate; 39. at least one polyol, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, at least one protein or protein hydrolysate, and at least one surfactant; 40. at least one polyol, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, at least one protein or protein hydrolysate, at least one surfactant, and at least one flavonoid; 41. at least one polyol, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, at least one PCT/US2006/044574 WO 2007/061795 56 protein or protein hydrolysate, at least one surfactant, at least one flavonoid, and at least one alcohol; 42. at least one polyol, at least one amino acid, and at least one sugar acid; 43. at least one polyol, at least one amino acid, and at least one nucleotide; 44. at least one polyol, at least one amino acid, and at least one organic acid; 45. at least one polyol, at least one amino acid, and at least one inorganic acid; 46. at least one polyol, at least one amino acid, and at least one bitter compound; 47. at least one polyol, at least one amino acid, and at least one polymer; 48. at least one polyol, at least one amino acid, and at least one protein or protein hydrolysate; 49. at least one polyol, at least one amino acid, and at least one surfactant; 50. at least one polyol, at least one amino acid, and at least one flavonoid; 51. at least one polyol, at least one amino acid, and at least one alcohol; 52. at least one polyol, at least one polyamino acid, and at least one sugar acid; 53. at least one polyol, at least one polyamino acid, and at least one nucleotide; 54. at least one polyol, at least one polyamino acid, and at least one organic acid; 55. at least one polyol, at least one polyamino acid, and at least one organic salt; 56. at least one polyol, at least one polyamino acid, and at least one inorganic acid; 57. at least one polyol, at least one polyamino acid, and at least one inorganic salt; 58. at least one polyol, at least one polyamino acid, and at least one bitter compound; 59. at least one polyol, at least one polyamino acid, and at least one polymer; 60. at least one polyol, at least one polyamino acid, and at least one protein or protein hydrolysate; 61. at least one polyol, at least one polyamino acid, and at least one surfactant; 62. at least one polyol, at least one polyamino acid, and at least one flavonoid; 63. at least one polyol, at least one polyamino add, and at least one alcohol; 64. at least one polyol, at least one sugar acid, and at least one nucleotide; 65. at least one polyol, at least one sugar acid, and at least one organic acid; 66. at least one polyol, at least one sugar acid, and at least one inorganic acid; 67. at least one polyol, at least one sugar acid, and at least one bitter compound; 68. at least one polyol, at least one sugar acid, and at least one polymer; WO 2007/061795 PCT/US2006/044574 2015203721 02 Jul2015 10 15 20 30 57 69. at least one polyol, at least one sugar acid, and at least one protein or protein hydrolysate; 70. at least one polyol, at least one sugar acid, and at least one surfactant; 71. at least one polyol, at least one sugar acid, and at least one flavonoid; 72. at least one polyol, at least one sugar acid, and at least one alcohol; 73. at least one polyol, at least one nucleotide, and at least one organic acid; 74. at least one polyol, at least one nucleotide, and at least one inorganic acid; 75. at least one polyol, at least one nucleotide, and at least one bitter compound; 76. at least one polyol, at least one nucleotide, and at least one polymer; 77. at least one polyol, at least one nucleotide, and at least one or protein protein hydrolysate; 78. at least one polyol, at least one nucleotide, and at least one surfactant; 79. at least one polyol, at least one nucleotide, and at least one flavonoid; 80. at least one polyol, at least one nucleotide, and at least one alcohol; 81. at least one polyol, at least one organic acid, and at least one inorganic acid; 82. at least one polyol, at least one organic acid, and at least one bitter compound; 83. at least one polyol, at least one organic acid, and at least one polymer; 84. at least one polyol, at least one organic acid, and at least one protein or protein hydrolysate; 85. at least one polyol, at least one organic acid, and at least one surfactant; 86. at least one polyol, at least one organic acid, and at least one flavonoid; 87. at least one polyol, at least one organic acid, and at least one alcohol; 88. at least one polyol, at least one inorganic acid, and at least one bitter compound; 89. at least one polyol, at least one inorganic acid, and at least one polymer; 90. at least one polyol, at least one inorganic acid, and at least one protein or protein hydrolysate; 91. at least one polyol, at least one inorganic acid, and at least one surfactant; 92. at least one polyol, at least one inorganic acid, and at least one flavonoid; 93. at least one polyol, at least one inorganic acid, and at least one alcohol; 94. at least one polyol, at least one bitter compound, and at least one polymer; WO 2007/061795 PCT/US2006/044574 58 2015203721 02 Jul2015 5 10 15 20 25 30 95. at least one polyol, at least one bitter compound, and at least one protein or protein hydrolysate; 96. at least one polyol, at least one bitter compound, and at least one surfactant; 97. at least one polyol, at least one bitter compound, and at least one flavonoid; 98. at least one polyol, at least one bitter compound, and at least one alcohol; 99. at least one polyol, at least one polymer, and at least one protein or protein hydrolysate; 100. at least one polyol, at least one polymer, and at least one surfactant; 101. at least one polyol, at least one polymer, and at least one flavonoid; 102. at least one polyol, at least one polymer, and at least one alcohol; 103. at least one polyol, at least one protein or protein hydrolysate, and at least one surfactant; 104. at least one polyol, at least one protein or protein hydrolysate, and at least one flavonoid; 105. at least one polyol, at least one surfactant, and at least one flavonoid; 106. at least one polyol, at least one surfactant, and at least one alcohol; 107. at least one polyol, at least one flavonoid, and at least one alcohol; 108. at least one sweet taste improving additive and erythritol; 109. at least one sweet taste improving additive and maltitol; 110. at least one sweet taste improving additive and mannitol; 111. at least one sweet taste improving additive and sorbitol; 112. at least one sweet taste improving additive and lactitol; 113. at least one sweet taste improving additive and xylitol; 114. at least one sweet taste improving additive and isomalt; 115. at least one sweet taste improving additive and propylene glycol; 116. at least one sweet taste improving additive and glycerol; 117. at least one sweet taste improving additive and palatinose; 118. at least one sweet taste improving additive and reduced isomalto-oligosaccharides; 119. at least one sweet taste improving additive and reduced xylo-oligosaccharides; 120. at least one sweet taste improving additive and reduced gentio-oligosaccharides; WO 2007/061795 PCT/US2006/044574 59 2015203721 02 Jul2015 121. at least one sweet taste improving additive and reduced maltose syrup; 122. at least one sweet taste improving additive and reduced glucose syrup; 123. at least one sweet taste improving additive, erythritol, and at least one other polyol; 5 124. at least one sweet taste improving additive, maltitol, and at least one other polyol; 125. at least one sweet taste improving additive, mannitol, and at least one other polyol; 126. at least one sweet taste improving additive, sorbitol, and at least one other 10 polyol; 127. at least one sweet taste improving additive, lactitol, and at least one other polyol; 128. at least one sweet taste improving additive, xylitol, and at least one other polyol; 15 129. at least one sweet taste improving additive, isomalt, and at least one other polyol; 130. at least one sweet taste improving additive, propylene glycol, and at least one other polyol; 131. at least one sweet taste improving additive, glycerol, and at least one other 20 polyol; 132. at least one sweet taste improving additive, palatinose, and at least one other polyol; 133. at least one sweet taste improving additive, reduced isomalto-oligosaccharides, and at least one other polyol; 25 134. at least one sweet taste improving additive, reduced xylo-oligosaccharides, and at least one other polyol; 135. at least one sweet taste improving additive, reduced gentio-oligosaccharides, and at least one other polyol; 136. at least one sweet taste improving additive, reduced maltose syrup, and at least 30 one other polyol; and 137. at least one sweet taste improving additive, reduced glucose syrup, and at least one other polyol. WO 2007/061795 PCT/US2006/044574 60 2015203721 02 Μ 2015
Other sweet taste improving composition combinations in accordance with embodiments of this invention include: 1. at least one polyol and tagatose; 2. at least one polyol and trehalose; 5 3. at least one polyol and galactose; 4. at least one polyol and rhamnose; 5. at least one polyol and dextrin; 6. at least one polyol and cyclodextrin; 7. at least one polyol and a-cyclodextrin, β-cyclodextrin, or γ-cyclodextrin; 10 8. at least one polyol and maltodextrin; 9. at least one polyol and dextran; 10. at least one polyol and sucrose; 11. at least one polyol and glucose; 12. at least one polyol and fructose; 15 13. at least one polyol and threose; 14. at least one polyol and arabinose; 15. at least one polyol and xylose; 16. at least one polyol and lyxose; 17. at least one polyol and allose; 20 18. at least one polyol and altrose; 19. at least one polyol and mannose; 20. at least one polyol and idose; 21. at least one polyol and talose; 22. at least one polyol and lactose; 25 23. at least one polyol and maltose; 24. at least one polyol and invert sugar; 25. at least one polyol and trehalose; 26. at least one polyol and isotrehalose; 27. at least one polyol and neotrehalose; 30 28. at least one polyol and palatinose; 29. at least one polyol and galactose; 30. at least one polyol and beet oligosaccharides; WO 2007/061795 PCT/US2006/044574 2015203721 02 Jul2015 61 31. at least one polyol and isomalto-oligosaccharides; 32. at least one polyol and isomaltose; .. 33. at least one polyol and isomaltotriose; 34. at least one polyol and panose; 5 35. at least one polyol and xylo-oligosaccharides; 36. at least one polyol and xylotriose; 37. at least one polyol and xylobiose; 38. at least one polyol and gentio-oligoscaccharides; 39. at least one polyol and gentiobiose; 10 40. at least one polyol and gentiotriose; 41. at least one polyol and gentiotetraose; 42. at least one polyol and sorbose; 43. at least one polyol and nigero-oligosaccharides; 44. at least one polyol and palatinose oligosaccharides 15 45. at least one polyol and fucose; 46. at least one polyol and fructooligosaccharides; 47. at least one polyol and kestose; 48. at least one polyol and nystose; 49. at least one polyol and maltotetraol; 20 50. at least one polyol and maltotriol; 51. at least one polyol and malto-oligosaccharides; 52. at least one polyol and maltotriose; 53. at least one polyol and maltotetraose; 54. at least one polyol and maltopentaose; 25 55. at least one polyol and maltohexaose; 56. at least one polyol and maltoheptaose; 57. at least one polyol and lactulose; 58. at least one polyol and melibiose; 59. at least one polyol and raffinose; 30 60. at least one polyol and rhamnose; 61. at least one polyol and ribose; 62. at least one polyol and isomerized liquid sugars; WO 2007/061795 PCT/US2006/044574 2015203721 02 Μ 2015 62 63. at least HFCS9 64. at least 65. at least 5 66. at least 67. at least 68. at least 69. at least 70. at least 10 71. at least 72. at least 73. at least 74. at least 75. at least 15 76. at least 77. at least 78. at least 79. at least 80. at least 20 81. at least 82.. at least 83. at least 84. at least 85. at least 25 86. at least 87. at least 88. at least 89. at least 90. at least 30 91. at least 92. at least 93. at least PCT/US2006/044574 WO 2007/061795 63 94. at least one polyol, palatinose, and at least one other carbohydrate; 95. at least one polyol, galactose, and at least one other carbohydrate; 96. at least one polyol, beet oligosaccharides, and at least one other carbohydrate; 97. at least one polyol, isomalto-oligosaccharides, and at least one other carbohydrate; 98. at least one polyol, isomaltose, and at least one other carbohydrate; 99. at least one polyol, isomaltotriose, and at least one other carbohydrate; 100. at least one polyol, panose, and at least one other carbohydrate; 101. at least one polyol, xylo-oligosaccharides, and at least one other carbohydrate; 102. at least one polyol, xylotriose, and at least one other carbohydrate; 103. at least one polyol, xylobiose, and at least one other carbohydrate; 104. at least one polyol, gentio-oligoscaccharides, and at least one other carbohydrate; 105. at least one polyol, gentiobiose, and at least one other carbohydrate; 106. at least one polyol, gentiotriose, and at least one other carbohydrate; 107. at least one polyol, gentiotetraose, and at least one other carbohydrate; 108. at least one polyol, sorbose, and at least one other carbohydrate; 109. at least one polyol, nigero-oligosaccharides, and at least one other carbohydrate; 110. at least one polyol, palatinose oligosaccharides, and at least one other carbohydrate; 111. at least one polyol, fucose, and at least one other carbohydrate; 112. at least one polyol, fructooligosaccharides, and at least one other carbohydrate; 113. at least one polyol, kestose, and at least one other carbohydrate; 114. at least one polyol, nystose, and at least one other carbohydrate; 115. at least one polyol, maltotetraol, and at least one other carbohydrate; 116. at least one polyol, maltotriol, and at least one other carbohydrate; 117. at least one polyol, malto-oligosaccharides, and at least one other carbohydrate; 118. at least one polyol, maltotriose, and at least one other carbohydrate; 119. at least one polyol, maltotetraose, and at least one other carbohydrate; 120. at least one polyol, maltopentaose, and at least one other carbohydrate; 121. at least one polyol, maltohexaose, and at least one other carbohydrate; WO 2007/061795 PCT/US2006/044574 64 2015203721 02 Jul2015 10 20 25 30 122. at least one polyol, maltoheptaose, and at least one other carbohydrate; 123. at least one polyol, lactulose, and at least one other carbohydrate; 124. at least one polyol, melibiose, and at least one other carbohydrate; 125. at least one polyol, raffinose, and at least one other carbohydrate; 126. at least one polyol, rhamnose, and at least one other carbohydrate; 127. at least one polyol, ribose, and at least one other carbohydrate; 128. at least one polyol, isomerized liquid sugars, and at least one other carbohydrate; 129. at least one polyol, high fructose com syrup (e.g. HFCS55, HFCS42, or HFCS90) or starch syrup, and at least one other carbohydrate; 130. at least one polyol, coupling sugars, and at least one other carbohydrate; 131. at least one polyol, soybean oligosaccharides, and at least one other carbohydrate; 132. at least one polyol, glucose syrup, and at least one other carbohydrate; 133. at least one carbohydrate and erythritol; 134. at least one carbohydrate and maltitol; 135. at least one carbohydrate and mannitol; 136. at least one carbohydrate and sorbitol; 137. at least one carbohydrate and lactitol; 138. at least one carbohydrate, and xylitol; 139. at least one carbohydrate and isomalt; 140. at least one carbohydrate and propylene glycol; 141. at least one carbohydrate and glycerol; 142. at least one carbohydrate and palatinose; 143. at least one carbohydrate and reduced isomalto-oligosaccharides; 144. at least one carbohydrate and reduced xylo-oligosaccharides; 145. at least one carbohydrate and reduced gentio-oligosaccharides; 146. at least one carbohydrate and reduced maltose syrup; 147. at least one carbohydrate and reduced glucose syrup; 148. at least one carbohydrate, erythritol, and at least one other polyol; 149. at least one carbohydrate, maltitol, and at least one other polyol; 150. at least one carbohydrate, mannitol, and at least one other polyol; WO 2007/061795 PCT/US2006/044574 2015203721 02 Μ 2015 10 1. at least one carbohydrate and at 20 2. at least one carbohydrate and at 3. at least one carbohydrate and at 4. at least one carbohydrate and at 5. at least one carbohydrate and at 6. at least one carbohydrate and at 25 7. at least one carbohydrate and at 8. at least one carbohydrate and at 9. at least one carbohydrate and at 10. at least one carbohydrate and at 11. at least one carbohydrate and at 30 12. at least one carbohydrate and at 13. at least one carbohydrate and at 65 151. at least one carbohydrate, sorbitol, and at least one other polyol; 152. at least one carbohydrate, lactitol, and at least one other polyol; 153. at least one carbohydrate, xylitol, and at least one other polyol; 154. at least one carbohydrate, isomalt, and at least one other polyol; 155. at least one carbohydrate, propylene glycol, and at least one other polyol; 156. at least one carbohydrate, glycerol, and at least one other polyol; 157. at least one carbohydrate, palatinose, and at least one other polyol; 158. at least one carbohydrate, reduced isomalto-oligosaccharides, and at least one other polyol; 159. at least one carbohydrate, reduced xylo-oligosaccharides, and at least one other polyol; 160. at least one carbohydrate, reduced gentio-oligosaccharides, and at least one other polyol; 161. at least one carbohydrate, reduced maltose syrup, and at least one other polyol; and 162. at least one carbohydrate, reduced glucose syrup, and at least one other polyol.
Other sweet taste improving composition combinations in accordance with embodiments of this invention include: least one amino acid; least one polyamino acid; least one sugar acid; least one nucleotide; least one organic acid; least one inorganic acid; least one bitter compound; least one flavorant or flavoring ingredient; least one polymer; least one protein or protein hydrolysate; least one surfactant; least one flavonoid; least one alcohol; WO 2007/061795 PCT/US2006/044574 66 2015203721 02 Μ 2015 14. at least one carbohydrate and at least one protein or protein hydrolysate or mixture of low molecular weight amino acids; , 15. at least one carbohydrate and at least one emulsifier; 16. at least one carbohydrate and at least one inorganic salt; 5 17. at least one carbohydrate, at least one amino acid, and at least one other sweet taste improving additive; 18. at least one carbohydrate, at least one polyamino acid, and at least one other sweet taste improving additive; 19. at least one carbohydrate, at least one sugar acid, and at least one other sweet 10 taste improving additive; 20. at least one carbohydrate, at least one nucleotide, and at least one other sweet taste improving additive; 21. at least one carbohydrate, at least one organic acid, and at least one other sweet taste improving additive; 15 22. at least one carbohydrate, at least one inorganic acid, and at least one other sweet taste improving additive; 23. at least one carbohydrate, at least one bitter compound, and at least one other sweet taste improving additive; 24. at least one carbohydrate, at least one flavorant or flavoring ingredient, and at 20 least one other sweet taste improving additive; 25. at least one carbohydrate, at least one polymer, and at least one other sweet taste improving additive; 26. at least one carbohydrate, at least one protein or protein hydrolysate, and at least one other sweet taste improving additive; 25 27. at least one carbohydrate, at least one surfactant, and at least one other sweet taste improving additive; 28. at least one carbohydrate, at least one flavonoid, and at least one other sweet taste improving additive; 29. at least one carbohydrate, at least one alcohol, and at least one other sweet taste 30 improving additive; 30. at least one carbohydrate, at least one amino acid, and at least one polyamino acid; WO 2007/061795 PCT/US2006/044574 2015203721 02 Μ 2015 67 10 20 25 30 31. at least one carbohydrate, at least one amino acid, at least one polyamino acid, and at least one sugar acid; 32. at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, and at least one nucleotide; 33. at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, and at least one organic acid; 34. at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, and at least one inorganic acid; 35. at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, and at least one bitter compound; 36. at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, and at least one polymer; 37. at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, and at least one protein or protein hydrolysate; 38. at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, at least one protein or protein hydrolysate, and at least one surfactant; 39. at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, at least one protein or protein hydrolysate, at least one surfactant, and at least one flavonoid; 40. at least one carbohydrate, at least one amino acid, at least one polyamino acid, at least one sugar acid, at least one nucleotide, at least one organic acid, at least one inorganic acid, at least one bitter compound, at least one polymer, at least WO 2007/061795 PCT/US2006/044574 2015203721 02 Jul2015 68 5 10 15 20 25 30 one protein hydrolysate, at least one surfactant, at least one flavonoid, and at least one alcohol; 41. at least one carbohydrate, at least one amino acid, and at least one sugar acid; 42. at least one carbohydrate, at least one amino acid, and at least one nucleotide; 43. at least one carbohydrate, at least one amino acid, and at least one organic acid; 44. at least one carbohydrate, at least one amino acid, and at least one inorganic acid; 45. at least one carbohydrate, at least one amino acid, and at least one bitter compound; 46. at least one carbohydrate, at least one amino acid, and at least one polymer; 47. at least one carbohydrate, at least one amino acid, and at least one protein or protein hydrolysate; 48. at least one carbohydrate, at least one amino acid, and at least one surfactant; 49. at least one carbohydrate, at least one amino acid, and at least one flavonoid; 50. at least one carbohydrate, at least one amino acid, and at least one alcohol; 51. at least one carbohydrate, at least one polyamino acid, and at least one sugar acid; 52. at least one carbohydrate, at least one polyamino acid, and at. least one nucleotide; 53. at least one carbohydrate, at least one polyamino acid, and at least one organic acid; 54. at least one carbohydrate, at least one polyamino acid, and at least one inorganic acid; 55. at least one carbohydrate, at least one polyamino acid, and at least one bitter compound; 56. at least one carbohydrate, at least one polyamino acid, and at least one polymer; 57. at least one carbohydrate, at least one polyamino acid, and at least one protein or protein hydrolysate; 58. at least one carbohydrate, at least one polyamino acid, and at least one surfactant; WO 2007/061795 PCT/US2006/044574 69 2015203721 02 Μ 2015 5 10 15 20 25 30 59. at least one carbohydrate, at least one polyamino acid, and at least one flavonoid; 60. at least one carbohydrate, at least one polyamino acid, and at least one alcohol; 61. at least one carbohydrate, at least one sugar acid, and at least one nucleotide; 62. at least one carbohydrate, at least one sugar acid, and at least one organic acid; 63. at least one carbohydrate, at least one sugar acid, and at least one inorganic acid; 64. at least one carbohydrate, at least one sugar acid, and at least one bitter compound; 65. at least one carbohydrate, at least one sugar acid, and at least one polymer; 66. at least one carbohydrate, at least one sugar acid, and at least one protein or protein hydrolysate; 67. at least one carbohydrate, at least one sugar acid, and at least one surfactant; 68. at least one carbohydrate, at least one sugar acid, and at least one flavonoid; 69. at least one carbohydrate, at least one sugar acid, and at least one alcohol; 70. at least one carbohydrate, at least one nucleotide, and at least one organic acid; 71. at least one carbohydrate, at least one nucleotide, and at least one inorganic acid; 72. at least one carbohydrate, at least one nucleotide, and at least one bitter compound; 73. at least one carbohydrate, at least one nucleotide, and at least one polymer; 74. at least one carbohydrate, at least one nucleotide, and at least one protein or protein hydrolysate; 75. at least one carbohydrate, at least one nucleotide, and at least one surfactant; 76. at least one carbohydrate, at least one nucleotide, and at least one flavonoid; 77. at least one carbohydrate, at least one nucleotide, and at least one alcohol; 78. at least one carbohydrate, at least one organic acid, and at least one inorganic acid; 79. at least one carbohydrate, at least one organic acid, and at least one bitter compound; at least one carbohydrate, at least one organic acid, and at least one polymer; 80. WO 2007/061795 PCT/US2006/044574 70 2015203721 02M2015 5 10 15 20 25 30 81. at least one carbohydrate, at least one organic acid, and at least one protein or protein hydrolysate; 82. at least one carbohydrate, at least one organic acid, and at least one surfactant; 83. at least one carbohydrate, at least one organic acid, and at least one flavonoid; 84. at least one carbohydrate, at least one organic acid, and at least one alcohol; 85. at least one carbohydrate, at least one inorganic acid, and at least one bitter compound; 86. at least one carbohydrate, at least one inorganic acid, and at least one polymer; 87. at least one carbohydrate, at least one inorganic acid, and at least one protein or protein hydrolysate; 88. at least one carbohydrate, at least one inorganic acid, and at least one surfactant; 89. at least one carbohydrate, at least one inorganic acid, and at least one flavonoid; 90. at least one carbohydrate, at least one inorganic acid, and at least one alcohol; 91. at least one carbohydrate, at least one bitter compound, and at least one polymer; 92. at least one carbohydrate, at least one bitter compound, and at least one protein or protein hydrolysate; 93. at least one carbohydrate, at least one bitter compound, and at least one surfactant; 94. at least one carbohydrate, at least one bitter compound, and at least one flavonoid.; 95. at least one carbohydrate, at least one bitter compound, and at least one alcohol; 96. at least one carbohydrate, at least one polymer, and at least one protein or protein hydrolysate; 97. at least one carbohydrate, at least one polymer, and at least one surfactant; 98. at least one carbohydrate, at least one polymer, and at least one flavonoid; 99. at least one carbohydrate, at least one polymer, and at least one alcohol; 100. at least one carbohydrate, at least one protein or protein hydrolysate, and at least one surfactant; WO 2007/061795 PCT/US2006/044574 71 2015203721 02 Jul2015 10 15 20 25 101. at least one carbohydrate, at least one protein or protein hydrolysate, and at least one flavonoid; 102. at least one carbohydrate, at least one surfactant, and at least one flavonoid; 103. at least one carbohydrate, at least one surfactant, and at least one alcohol; 104. at least one carbohydrate, at least one flavonoid, and at least one alcohol; \ 105. at least one sweet taste improving additive and D-tagatose; 106. at least one sweet taste improving additive and trehalose; 107. at least one sweet taste improving additive and D-galactose; 108. at least one sweet taste improving additive and rhamnose; 109. at least one sweet taste improving additive and dextrin; 110. at least one sweet taste improving additive and cyclodextrin; 111. at least one sweet taste improving additive and β-cyclodextrin; 112. at least one sweet taste improving additive and maltodextrin; 113. at least one sweet taste improving additive and dextran; 114. at least one sweet taste improving additive and sucrose; 115. at least one sweet taste improving additive and glucose; 116. at least one sweet taste improving additive and fructose; 117. at least one sweet taste improving additive and threose; 118. at least one sweet taste improving additive and arabinose; 119. at least one sweet taste improving additive and xylose; 120. at least one sweet taste improving additive and lyxose; 121. at least one sweet taste improving additive and allose: 122. at least one sweet taste improving additive and altrose; 123. at least one sweet taste improving additive and mannose; 124. at least one sweet taste improving additive and idose; 125. at least one sweet taste improving additive and talose; 126. at least one sweet taste improving additive and lactose; 127. at least one sweet taste improving additive and maltose; 128. at least one sweet taste improving additive and invert sugar; 129. at least one sweet taste improving additive and trehalose; 130. at least one sweet taste improving additive and isotrehalose; 131. at least one sweet taste improving additive and neotrehalose; WO 2007/061795 PCT/US2006/044574 2015203721 02 Jul2015 72 10 15 20 25 132. at least one sweet taste improving 133. at least one sweet taste improving 134. at least one sweet taste improving 135. at least one sweet taste improving 136. at least one sweet taste improving 137. at least one sweet taste improving 138. at least one sweet taste improving 139. at least one sweet taste improving 140. at least one sweet taste improving 141. at least one sweet taste improving 142. at least one sweet taste improving 143. at least one sweet taste improving 144. at least one sweet taste improving 145. at least one sweet taste improving 146. at least one sweet taste improving 147. at least one sweet taste improving 148. at least one sweet taste improving 149. at least one sweet taste improving 150. at least one sweet taste improving 151. at least one sweet taste improving 152. at least one sweet taste improving 153. at least one sweet taste improving 154. at least one sweet taste improving 155. at least one sweet taste improving 156. at least one sweet taste improving 157. at least one sweet taste improving 158. at least one sweet taste improving 159. at least one sweet taste improving 160. at least one sweet taste improving 161. at least one sweet taste improving 162. at least one sweet taste improving 163. at least one sweet taste improving additive and palatinose; additive and galactose; additive and beet oligosaccharides; additive and isomalto-oligosaccharides; additive and isomaltose; additive and isomaltotriose; additive and panose; additive and xylo-oligosaccharides; additive and xylotriose; additive and xylobiose; additive and gentio-oligoscaccharides; additive and gentiobiose; additive and gentiotriose; additive and gentiotetraose; additive and sorbose; additive and nigero-oligosaccharides; additive and palatinose oligosaccharides; additive and fucose; additive and fructooligosaccharides; additive and kestose; additive and nystose; additive and maltotetraol; additive and maltotriol; additive and malto-oligosaccharides; additive and maltotriose; additive and maltotetraose; additive and maltopentaose; additive and maltohexaose; additive and maltoheptaose; additive and lactulose; additive and melibiose; additive and raffinose; WO 2007/061795 PCT/US2006/044574 2015203721 02 Μ 2015 73 10 15 20 25 164. at least one sweet taste improving additive and rhamnose; 165. at least one sweet taste improving additive and ribose; 166. at least one sweet taste improving additive and isomerized liquid sugars; 167. at least one sweet taste improving additive and high fructose com syrup (e.g., HFCS55, HFCS42, or HFCS90) or starch syrup; 168. at least one sweet taste improving additive and coupling sugars; 169. at least one sweet taste improving additive and soybean oligosaccharides; 170. at least one sweet taste improving additive and glucose syrup; 171. at least one sweet taste improving additive, D-tagatose, and at least one other carbohydrate; 172. at least one sweet taste improving additive, trehalose, and at least one other carbohydrate; 173. at least one sweet taste improving additive, D-galactose, and at least one other carbohydrate; 174. at least one sweet taste improving additive, rhamnose, and at least one other carbohydrate; 175. at least one sweet taste improving additive, dextrin, and at least one other carbohydrate; 176. at least one sweet taste improving additive, cyclodextrin, and at least one other carbohydrate; 177. at least one sweet taste improving additive, β-cyclodextrin, and at least one other carbohydrate; 178. at least one sweet taste improving additive, maltodextrin, and at least one other carbohydrate; 179. at least one sweet taste improving additive, dextran, and at least one other carbohydrate; 180. at least one sweet taste improving additive, sucrose, and at least one other carbohydrate; 181. at least one sweet taste improving additive, glucose, and at least one other carbohydrate; 182. at least one sweet taste improving additive, fructose, and at least one other carbohydrate; WO 2007/061795 PCT/US2006/044574 2015203721 02 Jul2015 74 183. at least one sweet taste improving additive, threose, and at least one other carbohydrate; 184. at least one sweet taste improving additive, arabinose, and at least one other carbohydrate; 5 185. at least one sweet taste improving additive, xylose, and at least one other carbohydrate; 186. at least one sweet taste improving additive, lyxose, and at least one other carbohydrate; 187. at least one sweet taste improving additive, allose, and at least one other 10 carbohydrate; 188. at least one sweet taste improving additive, altrose, and at least one other carbohydrate; 189. at least one sweet taste improving additive, mannose, and at least one other carbohydrate; 15 190. at least one sweet taste improving additive, idose, and at least one other carbohydrate; 191. at least one sweet taste improving additive, talose, and at least one other carbohydrate; 192. at least one sweet taste improving additive, lactose, and at least one other 20 carbohydrate; 193. at least one sweet taste improving additive, maltose, and at least one other carbohydrate; 194. at least one sweet taste improving additive, invert sugar, and at least one other carbohydrate; 25 195. at least one sweet taste improving additive, trehalose, and at least one other carbohydrate; 196. at least one sweet taste improving additive, isotrehalose, and at least one other carbohydrate; 197. at least one sweet taste improving additive, neotrehalose, and at least one other 30 carbohydrate; 198. at least one sweet taste improving additive, palatinose, and at least one other carbohydrate; WO 2007/061795 PCT/US2006/044574 75 2015203721 02 Μ 2015 10 15 20 25 199. at least one sweet taste improving additive, galactose, and at least one other carbohydrate; 200. at least one sweet taste improving additive, beet oligosaccharides, and at least one other carbohydrate; 201. at least one sweet taste improving additive, isomalto-oligosaccharides, and at least one other carbohydrate; 202. at least one sweet taste improving additive, isomaltose, and at least one other carbohydrate; 203. at least one sweet taste improving additive, isomaltotriose, and at least one other carbohydrate; 204. at least one sweet taste improving additive, panose, and at least one other carbohydrate; 205. at least one sweet taste improving additive, xylo-oligosaccharides, and at least one other carbohydrate; 206. at least one sweet taste improving additive, xylotriose, and at least one other carbohydrate; 207. at least one sweet taste improving additive, xylobiose, and at least one other carbohydrate; 208. at least one sweet taste improving additive, gentio-oligoscaccharides, and at least one other carbohydrate; 209. at least one sweet taste improving additive, gentiobiose, and at least one other carbohydrate; 210. at least one sweet taste improving additive, gentiotriose, and at least one other carbohydrate; 211. at least one sweet taste improving additive, gentiotetraose, and at least one other carbohydrate; 212. at least one sweet taste improving additive, sorbose, and at least one other carbohydrate; 213. at least one sweet taste improving additive, nigero-oligosaccharides, and at least one other carbohydrate; 214. at least one sweet taste improving additive, palatinose oligosaccharides, and at least one other carbohydrate; WO 2007/061795 PCT/US2006/044574 76 2015203721 02 Jul2015 215. at least one sweet taste improving additive, fucose, and at least one other carbohydrate; 216. at least one sweet taste improving additive, fructooligosaccharides, and at least one other carbohydrate; 5 111. at least one sweet taste improving additive, kestose, and at least one other carbohydrate; 218. at least one sweet taste improving additive, nystose, and at least one other carbohydrate; 219. at least one sweet taste improving additive, maltotetraol, and at least one other 10 carbohydrate; 220. at least one sweet taste improving additive, maltotriol, and at least one other carbohydrate; 221. at least one sweet taste improving additive, malto-oligosaccharides, and at least one other carbohydrate; 15 222. at least one sweet taste improving additive, maltotriose, and at least one other carbohydrate; 223. at least one sweet taste improving additive, maltotetraose, and at least one other carbohydrate; 224. at least one sweet taste improving additive, maltopentaose, and at least one 20 other carbohydrate; 225. at least one sweet taste improving additive, maltohexaose, and at least one other carbohydrate; 226. at least one sweet taste improving additive, maltoheptaose, and at least one other carbohydrate; 25 227. at least one sweet taste improving additive, lactulose, and at least one other carbohydrate; 228. at least one sweet taste improving additive, melibiose, and at least one other carbohydrate; 229. at least one sweet taste improving additive, raffinose, and at least one other 30 carbohydrate; 230. at least one sweet taste improving additive, rhamnose, and at least one other carbohydrate; PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 77 231. at least one sweet taste improving additive, ribose, and at least one other carbohydrate; 232. at least one sweet taste improving additive, isomerized liquid sugars, and at least one other carbohydrate; 5 10 233. at least one sweet taste improving additive, high fructose com syrup (e.g. HFCS55, HFCS42, or HFCS90) or starch syrup, and at least one other carbohydrate; 234. at least one sweet taste improving additive, coupling sugars, and at least one other carbohydrate; 235. at least one sweet taste improving additive, soybean oligosaccharides, and at least one other carbohydrate; and 236. at least one sweet taste improving additive, glucose syrup, and at least one other carbohydrate.
In one embodiment, combinations of the at least one NHPS and at least one 15 sweet taste improving composition suppress, reduce, or eliminate undesirable taste and impart sugar-like characteristics to the NHPS composition. As used herein, the phrase “undesirable taste” includes any taste property which is not imparted by sugars such as glucose, sucrose, fructose, or similar saccharides. Non-limiting examples of undesirable tastes include delayed sweetness onset, lingering sweet aftertaste, metallic taste, bitter 20 taste, cooling sensation taste or menthol-like taste, licorice-like taste, and/or the like.
In another embodiment, at least one NHPS is combined with a plurality of sweet taste improving additives, desirably 3 or more sweet taste improving additives, and even more desirably 4 or more sweet taste improving additives, wherein each sweet taste improving additive is present in an amount such that no one sweet taste improving 25 additive imparts a substantial off taste to the NHPS composition. In other words, the amounts of the sweet taste improving additives in the NHPS composition are balanced so that no one sweet taste improving additive imparts a substantial off taste to the NHPS composition. Desirably, each of the plurality of sweet taste improving additives is present in the NHPS composition in an amount which imparts an osmlarity ranging from 10 to 100 30 mOsmoles/L to a sweetenable composition, but the combination of sweet improving additives imparts an osmolarity ranging from about 10 mOsmoles/L to about 500 mOsmoles/L to a sweetenable composition. PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 78
In one embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving nucleotide additive chosen from inosine monophosphate (“IMP”), 5 guanosine monophosphate (“GMP”), adenosine monophosphate (“AMP”), cytosine monophosphate (CMP), uracil monophosphate (UMP), inosine diphosphate, guanosine diphosphate, adenosine diphosphate, cytosine diphosphate, uracil diphosphate, inosine triphosphate, guanosine triphosphate, adenosine triphosphate, cytosine triphosphate, uracil triphosphate, nucleosides thereof, nucleic acid bases thereof, or salts thereof. 10 In one embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving carbohydrate additive chosen from tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g., a-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), 15 maltodextrin (including resistant maltodextrins such as Fibersol-2™), dextran, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, crythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, glucuronic acid, gluconic 20 acid, glucono-lactone, abequose, galactosamine, beet oligosaccharides, isomalto- oligosaccharides (isomaltose, isomaltotriose, panose and the like), xylo-oligosaccharides (xylotriose, xylobiose and the like), gentio-oligoscaccharides (gentiobiose, gentiotriose, gentiotetraose and the like), sorbose, nigero-oligosaccharides, palatinose oligosaccharides, fucose, fructooligosaccharides (kestose, nystose and the like), maltotetraol, maltotriol, 25 malto-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose and the like), lactulose, melibiose, raffinose, rhamnose, ribose, isomerized liquid sugars such as high fructose corn/starch syrup (e.g., HFCS55, HFCS42, or HFCS90), coupling sugars, soybean oligosaccharides, or glucose syrup.
In another embodiment, a sweetener composition is provided comprising at 30 least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving polyol additive chosen from erythritol, maltitol, mannitol, sorbitol, PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 79 lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerine), threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, or reduced glucose syrup.
In another embodiment, a sweetener composition is provided comprising at 5 least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving amino acid additive chosen from aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, 10 aminobutyric acid (alpha-, beta-, and gamma-isomers), glutamine, hydroxyproline, taurine, norvaline, sarcosine, or salts thereof.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet 15 taste improving polyamino acid additive chosen from poly-L-aspartic acid, poly-L-lysine (e.g., poly-L-a-lysine or poly-L-e-lysine), poly-L-omithine (e.g., poly-L-a-omithine or poly-L-s-omithine), poly-L-arginine, other polymeric forms of amino acids, or salts thereof.
In another embodiment, a sweetener composition is provided comprising at 20 least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving sugar acid additive chosen from aldonic, uronic, aldaric, alginic, gluconic, glucuronic, glucaric, galactaric, galacturonic, or salts thereof.
In another embodiment, a sweetener composition is provided comprising at 25 least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving organic acid additive chosen from the group C2-C30 carboxylic acids, substituted hydroxyl C1-C30 carboxylic acids, benzoic acid, substituted benzoic acids (e.g., 2,4-dihydroxybenzoic acid), substituted cinnamic acids, hydroxyacids, substituted 30 hydroxybenzoic acids, substituted cyclohexyl carboxylic acids, tannic acid, lactic acid, tartaric acid, citric acid, gluconic acid, glutaric acid, creatine, glucoheptonic acids, adipic PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 80 acid, hydroxycitric acid, malic acid, fmitaric acid, fumaric acid, maleic acid, succinic acid, chlorogenic acid, salicylic acid, caffeic acid, bile acids, acetic acid, ascorbic acid, alginic acid, erythorbic acid, polyglutamic acid, or salts thereof.
In another embodiment, a sweetener composition is provided comprising at 5 least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving inorganic acid additive chosen from phosphoric acid, phosphorous acid, polyphosphoric acid, hydrochloric acid, sulfuric acid, carbonic acid, sodium dihydrogen phosphate, or salts thereof. 10 In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving bitter compound additive chosen from caffeine, quinine, urea, bitter orange oil, naringin, quassia, or salts thereof. 15 In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving flavorant additive chosen from vanillin, vanilla extract, mango extract, cinnamon, citrus, coconut, ginger, viridiflorol, almond, menthol, grape skin extract, or 20 grape seed extract. In another particular embodiment, the at least one sweet taste improving flavorant additive comprises a proprietary sweetener chosen from Dohler™ Natural Flavoring Sweetness Enhancer K14323 (Dohler™, Darmstadt, Germany), Symrise™ Natural Flavor Mask for Sweeteners 161453 or 164126 (Symrise™, Holzminden, Germany), Natural Advantage™ Bitterness Blockers 1, 2, 9 or 10 (Natural 25 Advantage™, Freehold, New Jersey, U.S.A.), or Sucramask™ (Creative Research Management, Stockton, California, U.S.A.)
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet 30 taste improving polymer additive chosen from chitosan, pectin, pectic, pectinic, polyuronic, polygalacturonic acid, starch, food hydrocolloid or crude extracts thereof (e.g., PCT/US2006/044574 WO 2007/061795 81 2015203721 02 Μ 2015 gum acacia Senegal, gum acacia seyal, carageenan), poly-L-lysine (e.g., poly-L-a-lysine or poly-L-e-lysine), poly-L-omithine (e.g., poly-L-a-omithine or poly-L-s-omithine), polypropylene glycol, polyethylene glycol, poly(ethylene glycol methyl ether), polyarginine, polyaspartic acid, polyglutamic acid, polyethylene imine, alginic acid, 5 sodium alginate, propylene glycol alginate, sodium polyethyleneglycolalginate, sodium hexametaphosphate or its salts, or other cationic and anionic polymers.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet 10 taste improving protein or protein hydrolysate additive chosen from bovine serum albumin (BSA), whey protein (including fractions or concentrates thereof such as 90% instant whey protein isolate, 34% whey protein, 50% hydrolyzed whey protein, and 80% whey protein concentrate), soluble rice protein, soy protein, protein isolates, protein hydrolysates, reaction products of protein hydrolysates, glycoproteins, and/or 15 proteoglycans containing amino acids (e.g., glycine, alanine, serine, threonine, theanine, asparagine, glutamine, arginine, valine, isoleucine, leucine, norvaline, methionine, proline, tyrosine, hydroxyproline, or the like), collagen (e.g., gelatin), partially hydrolyzed collagen (e.g., hydrolyzed fish collagen), and collagen hydrolysates (e.g., porcine collagen hydrolysate). 20 In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving surfactant additive chosen from polysorbates (e.g., polyoxyethylene sorbitan monooleate (polysorbate 80), polysorbate 20, polysorbate 60), sodium 25 dodecylbenzenesulfonate, dioctyl sulfosuccinate or dioctyl sulfosuccinate sodium, sodium dodecyl sulfate, cetylpyridinium chloride, hexadecyltrimethylammonium bromide, sodium cholate, carbamoyl, choline chloride, sodium glycocholate, sodium taurodeoxycholate, lauric arginate, sodium stearoyl lactylate, lecithins, sucrose oleate esters, sucrose stearate esters, and other emulsifiers, or the like. 30 In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet PCT/US2006/044574 WO 2007/061795 82 2015203721 02 Μ 2015 taste improving flavonoid additive chosen from catechins, polyphenols, neohesperidin, naringin, neohesperidin dihydrochalcone, or the like.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside 5 V, Luo Han Guo sweetener, monatin, or curculin in combination with ethanol.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving astringent compound additive chosen from tannic acid, europium chloride 10 (EUCI3), gadolinium chloride (GdCL), terbium chloride (TbCls), alum, tannic acid, and polyphenols (e.g., tea polyphenol).
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet 15 taste improving inorganic salt additive chosen from sodium chloride, potassium chloride, sodium sulfate, potassium citrate, europium chloride (EuCL), gadolinium chloride (GdClj), terbium chloride (TbCL), magnesium sulfate, magnesium phosphate, alum, magnesium chloride, mono-, di-, tri-basic sodium or potassium salts of phosphoric acid (e.g., inorganic phosphates), salts of hydrochloric acid (e.g., inorganic chlorides), sodium 20 carbonate, sodium bisulfate, or sodium bicarbonate.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving nucleotide additive, at least one sweet taste improving carbohydrate 25 additive, and at least one sweet taste improving amino acid additive; wherein the at least one nucleotide additive is chosen from inosine monophosphate (“IMP”), guanosine monophosphate (“GMP”), adenosine monophosphate (“AMP”), cytosine monophosphate (CMP), uracil monophosphate (UMP), inosine diphosphate, guanosine diphosphate, adenosine diphosphate, cytosine diphosphate, uracil diphosphate, inosine triphosphate, 30 guanosine triphosphate, adenosine triphosphate, cytosine triphosphate, uracil triphosphate, nucleosides thereof, nucleic acid bases thereof, or salts thereof; wherein the at least one PCT/US2006/044574 WO 2007/061795 83 2015203721 02 Μ 2015 carbohydrate additive is chosen from tagatose, trehalose, galactose, rhamnose, ' cyclodextrin (e.g., a-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), maltodextrin (including resistant maltodextrins such as Fibersol-2™), dextran, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, 5 lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, glucono-lactone, abequose, galactosamine, beet oligosaccharides, isomalto-oligosaccharides (isomaltose, isomaltotriose, panose and the like), xylo-oligosaccharides 10 (xylotriose, xylobiose and the like), gentio-oligoscaccharides (gentiobiose, gentiotriose, gentiotetraose and the like), sorbose, nigero-oligosaccharides, palatinose oligosaccharides, fucose, fructooligosaccharides (kestose, nystose and the like), maltotetraol, maltotriol, malto-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose and the like), lactulose, melibiose, raffinose, rhamnose, ribose, isomerized 15 liquid sugars such as high fructose com/starch syrup (e.g., HFCS55, HFCS42, or HFCS90), coupling sugars, soybean oligosaccharides, or glucose syrup; and wherein the at least one amino acid additive is chosen from aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, 20 aminobutyric acid (alpha-, beta-, and gamma-isomers), glutamine, hydroxyproline, taurine, norvaline, sarcosine, or salts thereof.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet 25 taste improving nucleotide additive and at least one sweet taste improving carbohydrate additive; wherein the at least one nucleotide additive is chosen from inosine monophosphate (“IMP”), guanosine monophosphate (“GMP”), adenosine monophosphate (“AMP”), cytosine monophosphate (CMP), uracil monophosphate (UMP), inosine diphosphate, guanosine diphosphate, adenosine diphosphate, cytosine diphosphate, uracil 30 diphosphate, inosine triphosphate, guanosine triphosphate, adenosine triphosphate, cytosine triphosphate, uracil triphosphate, nucleosides thereof, nucleic acid bases thereof, or salts thereof; and wherein the at least one carbohydrate additive is chosen from PCT/US2006/044574 WO 2007/061795 84 2015203721 02 Μ 2015 tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g., a-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), maltodextrin (including resistant maltodextrins such as Fibersol-2™), dextran, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, 5 neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, amylopectin, glucosamine, maxmosamine, fucose, glucuronic acid,' gluconic acid, glucono-lactone, abequose, galactosamine, beet oligosaccharides, isomalto-oligosaccharides (isomaltose, isomaltotriose, panose and the like), xylo-oligosaccharides (xylotriose, xylobiose and the 10 like), gentio-oligoscaccharides (gentiobiose, gentiotriose, gentiotetraose and the like), sorbose, nigero-oligosaccharides, palatinose oligosaccharides, fucose, fructooligosaccharides (kestose, nystose and the like), maltotetraol, maltotriol, malto-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose and the like), lactulose, melibiose, raffinose, rhamnose, ribose, isomerized liquid sugars 15 such as high fructose com/starch syrup (e.g., HFCS55, HFCS42, or HFCS90), coupling sugars, soybean oligosaccharides, or glucose syrup.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet 20 taste improving nucleotide additive and at least one sweet taste improving polyol additive; wherein the at least one nucleotide additive is chosen from inosine monophosphate (“IMP”), guanosine monophosphate (“GMP”), adenosine monophosphate (“AMP”), cytosine monophosphate (CMP), uracil monophosphate (UMP), inosine diphosphate, guanosine diphosphate, adenosine diphosphate, cytosine diphosphate, uracil diphosphate, 25 inosine triphosphate, guanosine triphosphate, adenosine triphosphate, cytosine triphosphate, uracil triphosphate, nucleosides thereof, nucleic acid bases thereof, or salts thereof; and wherein the at least one polyol additive is chosen from erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, inositol, isomalt, propylene glycol, glycerol (glycerine), threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-30 oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, or reduced glucose syrup. PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 85
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving nucleotide additive and at least one sweet taste improving amino acid 5 additive; wherein the at least one nucleotide additive is chosen from inosine monophosphate (“IMP”), guanosine monophosphate (“GMP”), adenosine monophosphate (“AMP”), cytosine monophosphate (CMP), uracil monophosphate . (UMP), inosine diphosphate, guanosine diphosphate, adenosine diphosphate, cytosine diphosphate, uracil diphosphate, inosine triphosphate, guanosine triphosphate, adenosine triphosphate, 10 cytosine triphosphate, uracil triphosphate, nucleosides thereof, nucleic acid bases thereof, or salts thereof; and wherein the at least one amino acid additive is chosen from aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleudne, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid (alpha-, beta-, and gamma-isomers), glutamine, 15 hydroxyproline, taurine, norvaline, sarcosine, or salts thereof.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving carbohydrate additive, at least one sweet taste improving polyol additive, 20 and at least one sweet taste improving amino acid additive; wherein the at least one carbohydrate additive is chosen from tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g., a-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), maltodextrin (including resistant maltodextrins such as Fibersol-2™), dextran, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, 25 lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, tuxanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, glucono-lactone, abequose, galactosamine, beet oligosaccharides, isomalto-oligosaccharides (isomaltose, isomaltotriose, panose and the like), xylo-oligosaccharides 30 (xylotriose, xylobiose and the like), gentio-oligoscaccharides (gentiobiose, gentiotriose, gentiotetraose and the like), sorbose, nigero-oligosaccharides, palatinose oligosaccharides, fucose, fructooligosaccharides (kestose, nystose and the like), maltotetraol, maltotriol, PCT/US2006/044574 WO 2007/061795 86 2015203721 02 Μ 2015 malto-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose and the like), lactulose, melibiose, raffinose, rhamnose, ribose, isomerized liquid sugars such as high fructose com/starch syrup (e.g., HFCS55, HFCS42, or HFCS90), coupling sugars, soybean oligosaccharides, or glucose syrup; wherein the at 5 least one polyol additive is chosen from erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, inositol, isomalt, propylene glycol, glycerol (glycerine), threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, or reduced glucose syrup; and wherein the at least one amino acid additive is chosen from aspartic acid, arginine, glycine, 10 glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid (alpha-, beta-, and gamma-isomers), glutamine, hydroxyproline, taurine, norvaline, sarcosine, or salts thereof.
In another embodiment, a sweetener composition is provided comprising at 15 least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving carbohydrate additive and at least one sweet taste improving polyol additive; wherein the at least one carbohydrate additive is chosen from tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g., a-cyclodextrin, β-cyclodextrin, and γ-20 cyclodextrin), maltodextrin (including resistant maltodextrins such as Fibersol-2™), dextran, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, 25 glucuronic acid, gluconic acid, glucono-lactone, abequose, galactosamine, beet oligosaccharides, isomalto-oligosaccharides (isomaltose, isomaltotriose, panose and the like), xylo-oligosaccharides (xylotriose, xylobiose and the like), gentio-oligoscaccharides (gentiobiose, gentiotriose, gentiotetraose and the like), sorbose, nigero-oligosaccharides, palatinose oligosaccharides, fucose, fructooligosaccharides (kestose, nystose and the like), 30 maltotetraol, maltotriol, malto-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose and the like), lactulose, melibiose, raffinose, rhamnose, ribose, isomerized liquid sugars such as high fructose com/starch syrup (e.g., PCT/US2006/044574 WO 2007/061795 87 2015203721 02 Jul2015 HFCS55, HFCS42, or HFCS90), coupling sugars, soybean oligosaccharides, or glucose syrup; and wherein the at least one polyol additive is chosen from erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, inositol, isomalt, propylene glycol, glycerol (glycerine), threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-5 oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, or reduced glucose syrup.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet 10 taste improving carbohydrate additive and at least one sweet taste improving amino acid additive; wherein the at least one carbohydrate additive is chosen from tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g., a-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), maltodextrin (including resistant maltodextrins such as Fibersol-2™), dextran, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, 15 altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, glucono-lactone, abequose, galactosamine, beet oligosaccharides, isomalto-oligosaccharides (isomaltose, isomaltotriose, panose and the 20 like), xylo-oligosaccharides (xylotriose, xylobiose and the like), gentio-oligoscaccharides (gentiobiose, gentiotriose, gentiotetraose and the like), sorbose, nigero-oligosaccharides, palatinose oligosaccharides, fucose, fructooligosaccharides (kestose, nystose and the like), maltotetraol, maltotriol, malto-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose and the like), lactulose, melibiose, raffinose, 25 rhamnose, ribose, isomerized liquid sugars such as high fructose com/starch syrup (e.g„ HFCS55, HFCS42, or HFCS90), coupling sugars, soybean oligosaccharides, or glucose syrup; and wherein the at least one amino acid additive is chosen from aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleucine, asparagine, serine, lysine, histidine, ornithine, 30 methionine, carnitine, aminobutyric acid (alpha-, beta-, and gamma-isomers), glutamine, hydroxyproline, taurine, norvaline, sarcosine, or salts thereof. PCT/US2006/044574 WO 2007/061795 88 2015203721 02 Μ 2015
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving polyol additive and at least one sweet taste improving amino acid additive; 5 wherein the at least one polyol additive is chosen from erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, inositol, isomalt, propylene glycol, glycerol (glycerin), threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, or reduced glucose syrup; and wherein the at least one amino acid additive is chosen from aspartic acid, arginine, 10 glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid (alpha-, beta-, and gamma-isomers), glutamine, hydroxyproline, taurine, norvaline, sarcosine, or salts thereof.
In another embodiment, a sweetener composition is provided comprising at 15 least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving polyol additive and at least one sweet taste improving inorganic salt additive; wherein the at least one polyol additive is chosen from erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, inositol, isomalt, propylene glycol, glycerol (glycerin), 20 threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, or reduced glucose syrup; and wherein the at least one inorganic salt additive is chosen from sodium chloride, potassium chloride, sodium sulfate, potassium citrate, europium chloride (EuCl3), gadolinium chloride (GdCl3), terbium chloride (TbCl3), magnesium sulfate, alum, 25 magnesium chloride, mono-, di-, tri-basic sodium or potassium salts of phosphoric acid (e.g., inorganic phosphates), salts of hydrochloric acid (e.g., inorganic chlorides), sodium carbonate, sodium bisulfate, or sodium bicarbonate.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside 30 V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving carbohydrate additive and at least one sweet taste improving inorganic salt additive; wherein the at least one carbohydrate additive is chosen from tagatose, trehalose, PCT/US2006/044574 WO 2007/061795 89 2015203721 02 Μ 2015 galactose, rhamnose, cyclodextrin (e.g., a-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), maltodextrin (including resistant maltodextrins such as Fibersol-2™), dextran, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, 5 palatinose or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, glucono-lactone, abequose, galactosamine, beet oligosaccharides, isomalto-oligosaccharides (isomaltose, isomaltotriose, panose and the like), xylo-oligosaccharides (xylotriose, xylobiose and the like), gentio-oligoscaccharides 10 (gentiobiose, gentiotriose, gentiotetraose and the like), sorbose, nigero-oligosaccharides, palatinose oligosaccharides, fucose, fructooligosaccharides (kestose, nystose and the like), maltotetraol, maltotriol, malto-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose and the like), lactulose, melibiose, raffinose, rhamnose, ribose, isomerized liquid sugars such as high fructose com/starch syrup (e.g., 15 HFCS55, HFCS42, or HFCS90), coupling sugars, soybean oligosaccharides, or glucose syrup; and wherein the at least one inorganic salt additive is chosen from sodium chloride, potassium chloride, sodium sulfate, potassium citrate, europium chloride (EUCI3), gadolinium chloride (GdCl3), terbium chloride (TbCl3), magnesium phosphate, magnesium sulfate, alum, magnesium chloride, mono-, di-, tri-basic sodium or potassium 20 salts of phosphoric acid (e.g., inorganic phosphates), salts of hydrochloric acid (e.g., inorganic chlorides), sodium carbonate, sodium bisulfate, or sodium bicarbonate.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet 25 taste improving carbohydrate additive, at least one sweet taste improving amino acid additive, and at least one sweet taste improving inorganic salt additive; wherein the at least one carbohydrate additive is chosen from tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g., a-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), maltodextrin (including resistant maltodextrins such as Fibersol-2™), dextran, sucrose, glucose, 30 ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 90 cellobiose, amylopectin, glucosamine, maimosamine, fucose, glucuronic acid, gluconic acid, glucono-lactone, abequose, galactosamine, beet oligosaccharides, isomalto-oligosaccharides (isomaltose, isomaltotriose, panose and the like), xylo-oligosaccharides (xylotriose, xylobiose and the like), gentio-oligoscaccharides (gentiobiose, gentiotriose, 5 gentiotetraose and the like), sorbose, nigero-oligosaccharides, palatinose oligosaccharides, fucose, fructooligosaccharides (kestose, nystose and the like), maltotetraol, maltotriol, malto-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose and the like), lactulose, melibiose, raffinose, rhamnose, ribose, isomerized liquid sugars such as high fructose com/starch syrup (e.g., HFCS55, HFCS42, or 10 HFCS90), coupling sugars, soybean oligosaccharides, or glucose syrup; wherein the at least one amino acid additive is chosen from aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid (alpha-, beta-, and gamma-isomers), glutamine, hydroxyproline, 15 taurine, norvaline, sarcosine, or salts thereof; and wherein the at least one inorganic salt additive is chosen from sodium chloride, potassium chloride, sodium sulfate, potassium citrate, europium chloride (EuCb), gadolinium chloride (GdC^), terbium chloride (TbCl3), magnesium phosphate, magnesium sulfate, alum, magnesium chloride, mono-, di-, tri-basic sodium or potassium salts of phosphoric acid (e.g., inorganic phosphates), salts of 20 hydrochloric acid (e.g., inorganic chlorides), sodium carbonate, sodium bisulfate, or sodium bicarbonate.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet 25 taste improving polyol additive and at least one sweet taste improving polyamino acid additive; wherein the at least one polyol additive is chosen from erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, inositol, isomalt, propylene glycol, glycerol (glycerin), threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, or reduced 30 glucose syrup; and wherein the at least one polyamino acid additive is chosen from poly-L-aspartic acid, poly-L-lysine (e.g., poly-L-a-lysine or poly-L-s-lysine), poly-L-omithine PCT/US2006/044574 WO 2007/061795 2015203721 02M2015 91 (e.g., poly-L-a-omithine or poly-L-s-omithine), poly-L-arginine, and other polymeric forms of amino acids, or salts thereof.
In another embodiment, a sweetener composition is provided comprising at least one functional ingredient and at least one NHPS chosen from rebaudioside-A, stevia, 5 stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving protein or protein hydrolysate additive and at least one sweet taste improving inorganic salt additive; wherein the at least one sweet taste improving protein hydrolysate additive is chosen from bovine serum albumin (BSA), whey protein (including fractions or concentrates thereof such as 90% 10 instant whey protein isolate, 34% whey protein, 50% hydrolyzed whey protein, and 80% whey protein concentrate), soluble rice protein, soy protein, protein isolates, protein hydrolysates, reaction products of protein hydrolysates, glycoproteins, and/or proteoglycans containing amino acids (e.g., glycine, alanine, serine, threonine, asparagine, glutamine, arginine, valine, isoleucine, leucine, norvaline, methionine, proline, tyrosine, 15 hydroxyproline, or the like), collagen (e.g., gelatin), partially hydrolyzed collagen (e.g., hydrolyzed fish collagen), and collagen hydrolysates (e.g., porcine collagen hydrolysate); and wherein the at least one sweet taste improving inorganic salt additive is chosen from sodium chloride, potassium chloride, sodium sulfate, potassium citrate, europium chloride (EuCl3), gadolinium chloride (GdCl3), terbium chloride (TbCIs), magnesium phosphate, 20 magnesium sulfate, alum, magnesium chloride, mono-, di-, tri-basic sodium or potassium salts of phosphoric acid (e.g., inorganic phosphates), salts of hydrochloric acid (e.g., inorganic chlorides), sodium carbonate, sodium bisulfate, or sodium bicarbonate.
In another embodiment, a sweetener composition is provided comprising rebaudioside A in combination with at least one NHPS other than rebaudioside-A and at 25 least one sweet taste improving composition.
In another embodiment, a sweetener composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, monatin, or curculin in combination with at least one synthetic sweetener chosen from sucralose, acesulfame potassium and other salts, 30 aspartame, alitame, saccharin, neohesperidin dihydrochalcone, cyclamate, neotame, N-[N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-L-a-aspartyl]-L-phenylalanine 1-methyl ester, N-[N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-L-a-aspartyl]-L-phenylalanine 1- PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 92 methyl ester, N- [N- [3-(3-methoxy-4-hydroxyphenyl)propyl] -L-a-aspartyl] -L- phenylalanine 1-methyl ester, salts thereof, and the like.
In one embodiment, a composition comprising rebaudioside-A (REBA) in combination with at least one sweet taste improving amino acid additive and at least one 5 sweet taste improving polyol additive is provided. In a particular embodiment, the at least one sweet taste improving amino acid additive is present in an amount from about 100 ppm to about 25,000 ppm of the composition, and the at least one sweet taste improving polyol additive is present in an amount from about 400 to about 80,000 ppm of the composition. In a still more particular embodiment, the at least one sweet taste improving 10 amino acid additive is glycine or alanine, and the at least one sweet taste improving polyol additive is erythritol.
In one embodiment, a NHPS composition comprising rebaudioside-A (REBA) (with at least 50 % REBA in a steviol glycoside mixture) in combination with at least one sweet taste improving polyol additive is provided. Desirably, the at least one 15 sweet taste improving polyol additive comprises erythritol. In a particular embodiment of the NHPS composition, rebaudioside A is present in an amount from about 100 to about 3,000 ppm and the erythritol is present in an amount from about 400 to about 80,000 ppm of the total sweetener composition. In another embodiment of the functional sweetener composition, rebaudioside A is present in an amount from about 100 to about 3,000 ppm 20 and the erythritol is present in an amount from about 5,000 to about 40,000 ppm of the total sweetener composition. In still another embodiment of the NHPS composition, rebaudioside A is present in an amount from about 100 to about 3,000 ppm and the erythritol is present in an amount from about 10,000 to about 35,000 ppm of the total sweetener composition. In another particular embodiment of the NHPS composition, 25 rebaudioside A and erythritol are present in the sweetener composition in a ratio from about 1:4 to about 1:800, respectively. In yet another particular embodiment of the NHPS composition, rebaudioside A and erythritol are present in the sweetener composition in a ratio from about 1:20 to about 1:600, respectively; more particularly from about 1:50 to about 1:300; and still more particularly from about 1:75 to about 1:150. 30 In another embodiment, a functional sweetener composition comprising at least one functional ingredient and a sweetener composition comprising rebaudioside-A (REBA), stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, PCT/US2006/044574 WO 2007/061795 93 2015203721 02 Μ 2015 monatin, or curculin, in combination with at least one sweet taste improving synthetic sweetener additive is provided. In a particular embodiment, the functional sweetener composition comprises at least one functional ingredient and a sweetener comprising rebaudioside-A (REBA) in combination with saccharin or acesulfame potassium or other 5 salts in an amount from about 10 ppm to about 100 ppm of the composition.
In one embodiment, a composition comprising REBA in combination with at least one sweet taste improving amino acid additive and at least one sweet taste improving protein or protein hydrolysate additive is provided. In a particular embodiment, the at least one sweet taste improving amino acid additive is present in an amount from 10 about 100 to about 25,000 ppm of the composition, and the at least one sweet taste improving protein or protein hydrolysate additive is present in an amount from about 200 ppm to about 50,000 ppm of the composition. In a still more particular embodiment, the at least one sweet taste improving amino acid additive is glycine or lysine, and the at least one sweet taste improving protein or protein hydrolysate additive is protein, a hydrolysate, 15 or a reaction product of a hydrolysate of a protein containing glycine, alanine, serine, leucine, valine, isoleucine, proline, or threonine.
In one embodiment, a composition comprising REBA in combination with at least one sweet taste improving protein hydrolysate additive and at least one sweet taste improving polyol additive is provided. In a particular embodiment, the at least one sweet 20 taste improving protein or protein hydrolysate additive is present in an amount from about 200 ppm to about 50,000 ppm of the composition, and at least one sweet taste improving polyol additive is present in an amount from about 400 to about 80,000 ppm of the composition. In a still more particular embodiment, the at least one sweet taste improving protein or protein hydrolysate additive is a protein, a hydrolysate, or a reaction product of 25 a hydrolysate of proteins containing glycine, alanine, serine, leucine, valine, isoleucine, proline, or threonine, and the at least one sweet taste improving polyol additive is erythritol.
In one embodiment, a composition comprising REBA in combination with at least one sweet taste improving carbohydrate additive is provided. In a particular 30 embodiment, the at least one sweet taste improving carbohydrate additive is present in an amount from about 1,000 to about 100,000 ppm of the composition. In a still more PCT/US2006/044574 WO 2007/061795 94 2015203721 02 Μ 2015 particular embodiment, the composition comprises REBA and glucose, sucrose, HFCS, or D-fructose in an amount from about 10,000 ppm to about 80,000 ppm of the composition.
In one embodiment, a composition comprising REBA in combination with at least one sweet taste improving polyol additive is provided. In a particular embodiment, 5 the at least one sweet taste improving polyol additive is present in an amount from about 400 to about 80,000 ppm of the composition. In another particular embodiment, the at least one sweet taste improving polyol additive is present in an amount from about 5,000 to about 60,000 ppm of the composition. Non-limiting examples include REBA in combination with propylene glycol, erythritol, or combinations thereof. 10 In one embodiment, a composition comprising REBA in combination with at least one sweet taste improving polyol additive is provided. Desirably, the at least one sweet taste improving polyol comprises erythritol. In a particular embodiment of the composition, REBA is present in an amount from about 100 to about 3,000 ppm and the erythritol is present in an amount from about 400 to about 80,000 ppm of the total 15 composition. In another particular embodiment of the composition, REBA and erythritol are present in the composition in a ratio from about 1:4 to about 1:800, respectively. In yet another particular embodiment of the composition, REBA and erythritol are present in the composition in a ratio from about 1:20 to about 1:600, respectively; more particularly from about 1:50 to about 1:300; and still more particularly from about 1:75 to about 1:150. 20 Desirably, the REBA has a purity of at least 50 % REBA by weight in a steviolglycoside mixture.
In one embodiment, a composition comprising REBA in combination with at least one sweet taste improving carbohydrate additive and at least one sweet taste improving polyol additive is provided. In a particular embodiment, the at least one sweet 25 taste improving carbohydrate additive is present in an amount from about 1,000 to about 100,000 ppm of the composition and at least one sweet taste improving polyol additive is present in an amount from about 400 to about 80,000 ppm of the composition. Nonlimiting examples include REBA in combination with tagatose, fructose or sucrose and erythritol. 30 In one embodiment, a composition comprising REBA in combination with at least one sweet taste improving inorganic salt additive is provided. Non-limiting WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 95 examples include REBA in combination with NaCl, KC1, NaHS04.H20, NaH2P04, MgS04, KA1(S04)2 (alum), magnesium phosphate, magnesium chloride, KC1 and KH2PO4, or other combinations thereof. A particularly desirable embodiment comprises REBA in combination with a mixture of inorganic salt additives, such as chlorides, 5 phosphates, and sulfates of sodium, magnesium, potassium, and calcium (e.g., sodium chloride and potassium chloride; potassium phosphate and potassium chloride; sodium chloride and sodium phosphate; calcium phosphate and calcium sulfate; magnesium chloride and magnesium phosphate; and calcium phosphate, calcium sulfate, and potassium sulfate). 10 In one embodiment, a composition comprising REBA in combination with at least one sweet taste improving organic acid salt additive is provided. Non-limiting examples include REBA in combination with choline chloride in citrate buffer, D-gluconic acid sodium salt, guanidine HC1, D-glucosamine HC1, amiloride HC1, or combinations thereof. 15 In one embodiment, a composition comprising REBA in combination with at least one sweet taste improving organic acid additive is provided. Non-limiting examples include REBA in combination with fumaric acid, malic acid, tartaric acid, citric acid, adipic acid, ascorbic acid, tannic acid, lauric arginate, or combinations thereof.
In one embodiment, a composition comprising REBA in combination with 20 at least one sweet taste improving amino acid additive is provided. In a particular embodiment, the at least one sweet taste improving amino acid additive is present in an amount from about 100 to about 15,000 ppm of the composition. Non-limiting examples include REBA in combination with glycine, L-alanine, L-serine, L-threonine, β-alanine, aminobutyric acid (alpha-, beta-, and gamma- isomers), L-aspartic acid, L-glutamic acid, 25 L-lysine, glycine and L-alanine mixture, salt derivatives or combinations thereof.
In one embodiment, a composition comprising REBAin combination with at least one sweet taste improving surfactant additive is provided. Non-limiting examples include REBA in combination with dioctyl sulfosuccinate sodium, cetylpyridinium chloride, hcxadecyltrimethylammonium bromide, sucrose oleate, polysorbate 20, 30 polysorbate 80, lecithin, or combinations thereof. PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 96
In one embodiment, a composition comprising REBA in combination with at least one sweet taste improving polymer additive is provided. Non-limiting examples include REBA in combination with cationic polymers such as polyethyleneimine, poly-L-lysine (e.g., poly-L-a-lysine or poly-L-s-lysine), poly-L-omithine (e.g., poly-L-a-omithine 5 or poly-L-s-omithine), chitosan, or combinations thereof.
In one embodiment, a composition comprising REBA in combination with at least one sweet taste improving polymer additive and at least one sweet taste improving polyol additive is provided. In a particular embodiment, the at least one sweet taste improving polymer additive is present in an amount from about 30 to about 2,000 ppm of 10 the composition, and the at least one sweet taste improving polyol additive is present in an amount from about 400 to about 80,000 ppm of the composition. Non-limiting examples include REBA in combination with a hydrocolloid, such as a gum acacia seyal, and erythritol.
In one embodiment, a composition comprising REBA in combination with 15 at least one sweet taste improving protein or protein hydrolysate additive is provided. Non-limiting examples include REBA in combination with bovine serum albumin (BSA), whey protein or combinations thereof.
In another embodiment, a composition comprising REBA in combination with at least one sweet taste improving amino acid additive and at least one sweet taste 20 improving inorganic acid salt additive is provided. In a particular embodiment, the at least one sweet taste improving amino acid additive is present in an amount from about 100 to about 25,000 ppm of the composition and the at least one sweet taste improving inorganic acid salt additive additive is present in an amount from about 25 to about 5,000 ppm of the composition. Non-limiting examples include REBA in combination with glycine and 25 alum; REBA in combination with glycine and potassium chloride; REBA in combination with glycine and sodium chloride; REBA in combination with glycine, potassium phosphate, and potassium chloride; and REBA in combination with glycine, sodium chloride, and potassium chloride.
In another embodiment, a composition comprising REBA in combination 30 with at least one sweet taste improving carbohydrate additive and at least one sweet taste improving inorganic acid salt additive is provided. In a particular embodiment, the at least PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 97 one sweet taste improving carbohydrate additive is present in an amount from about 1,000 to about 100,000 ppm of the composition and the at least one sweet taste improving inorganic acid salt additive is present additive is present in an amount from about 25 to about 5,000 ppm of the composition. Non-limiting examples include REBA in 5 combination with fructose, sucrose, or glucose and alum; REBA in combination with fructose, sucrose, or glucose and potassium chloride; REBA in combination with fructose, sucrose, or glucose and sodium chloride; REBA in combination with fructose, sucrose, or glucose, potassium phosphate, and potassium chloride; and REBA in combination with fructose, sucrose, or glucose, sodium chloride, and potassium chloride. 10 In another embodiment, a composition comprising REBA in combination with at least one sweet taste improving bitter additive and at least one sweet taste improving inorganic salt additive is provided. A non-limiting example includes REBA in combination with urea and sodium chloride.
In another embodiment, a composition comprising REBA in combination 15 with at least one sweet taste improving amino acid additive and at least one sweet taste improving polyamino acid additive is provided. In a particular embodiment, the at least one sweet taste improving amino acid additive is present in an amount from about 100 to about 25,000 ppm of the composition and the at least one sweet taste improving polyamino acid additive is present in an amount from about 30 to about 2,000 ppm of the 20 composition. Non-limiting examples include REBA in combination with glycine and poly-L-a-lysine; and REBA in combination with glycine and poly-L-s-lysine.
In another embodiment, a composition comprising REBA in combination with at least one sweet taste improving amino acid additive and at least one sweet taste improving organic acid additive is provided, hi a particular embodiment, the at least one 25 sweet taste improving amino acid additive is present in an amount from about 100 to about 25,000 ppm of the composition and the at least one sweet taste improving organic acid additive is present in an amount from about 10 to about 5,000 ppm of the composition. A non-limiting example includes REBA in combination with glycine and sodium gluconate.
In another embodiment, a composition comprising REBA in combination 30 with at least one sweet taste improving amino acid additive and at least one sweet taste improving carbohydrate additive is provided. In a particular embodiment, the at least one PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 98 sweet taste improving amino acid additive is present in an amount from about 100 to about 25,000 ppm of the composition and the at least one sweet taste improving carbohydrate additive is present in an amount from about 1,000 to about 100,000 ppm of the composition. A non-limiting example includes REBA in combination with L-alanine and 5 fructose.
In another embodiment, a composition comprising REBA in combination with at least one sweet taste improving amino acid additive, at least one sweet taste improving polyol additive, at least one sweet taste improving inorganic salt additive, and at least one sweet taste improving organic acid salt additive is provided. In a particular 10 embodiment, the at least one sweet taste improving amino acid additive is present in an amount from about 100 to about 25,000 ppm of the composition, the at least one sweet taste improving polyol additive is present in an amount from about 400 to about 80,000 ppm of the composition, the at least one sweet taste improving inorganic salt additive is present in an amount from about 25 to about 5,000 ppm of the composition, and the at 15 least one sweet taste improving organic acid salt additive is present in an amount from about 20 to about 10,000 ppm of the composition. A non-limiting example includes REBA in combination with erythritol, glycine, KC1, KH2PO4, and choline chloride.
In another embodiment, a composition comprising REBA in combination with at least one sweet taste improving amino acid additive, at least one sweet taste 20 improving carbohydrate additive, and at least one sweet taste improving polyol additive is provided. In a particular embodiment, the at least one sweet taste improving amino acid additive is present in an amount from about 100 to about 25,000 ppm of the composition, the at least one sweet taste improving carbohydrate additive is present in an amount from about 1,000 to about 100,000 ppm of the composition, and the at least one sweet taste 25 improving polyol additive is present in an amount from about 400 to about 80,000 ppm of the composition. A non-limiting example includes REBA in combination with L-alanine, fructose, and erythritol.
In another embodiment, a composition comprising REBA in combination with at least one sweet taste improving amino acid additive, at least one sweet taste 30 improving polyol, additive, and at least one sweet taste improving inorganic acid salt additive is provided. In a particular embodiment, the at least one sweet taste improving amino acid additive is present in an amount from about 100 to about 25,000 ppm of the PCT/US2006/044574 WO 2007/061795 99 2015203721 02 Jul2015 composition, the at least one sweet taste improving polyol additive is present in an amount from about 400 to about 80,000 ppm of the composition, and the at least one sweet taste improving inorganic acid salt additive is present in an amount from about 25 to about 5,000 ppm of the composition. A non-limiting example includes REBA in combination 5 with erythritol, glycine, KC1, and KH2PO4.
In another embodiment, a composition comprising REBA in combination with a sweet taste improving inorganic acid salt additive is provided. A non-limiting example includes REBA in combination with sodium chloride.
In another embodiment, a composition comprising glycyrrihizin such as 10 mono-ammonium glycyrrhizic acid salt hydrate in combination with a sweet taste improving inorganic acid salt additive is provided. A non-limiting example includes monoammonium glycyrrhizic acid salt hydrate in combination with sodium chloride.
In one embodiment, a composition is provided comprising at least one NHPS chosen from rebaudioside-A, stevia, stevioside, mogroside IV, mogroside V, Luo 15 Han Guo sweetener, monatin, or curculin in combination with at least one sweet taste improving polyol additive and at least one sweet taste improving organic acid additive. Desirably, the at least one sweet taste improving polyol additive is present in an amount from about 20,000 to about 50,000 ppm of the composition and the at least one sweet taste improving organic acid additive is present in an amount from about 10 to about 5,000 ppm 20 of the composition. Wherein more than one sweet taste improving organic acid additive is present in the composition, the plurality of sweet taste improving organic acid additives are present in an amount from about 500 to about 2,500 ppm of the composition, more particularly in an amount from about 500 to about 1,500 ppm of the composition. In a particular embodiment, the composition described hereinabove further comprises at least 25 one sweet taste improving inorganic acid additive, at least one sweet taste improving inorganic acid salt additive, at least one sweet taste improving organic acid salt additive, or combinations thereof.
In another embodiment, a composition comprising REBA in combination with at least one sweet taste improving polyol additive and at least one sweet taste 30 improving organic acid additive is provided. Desirably, the REBA has a purity from about 50 to about 100% by weight of REBA, more desirably from about 80 to about 99.5% by WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 100 weight REBA, most desirably from about 97 to about 99.5% by weight REBA in a steviolglycoside mixture. In a particular embodiment, the REBA is present in the composition in an amount from about 100 to about 3,000 ppm, more desirably in an amount from about 200 to about 2,000 ppm, and even more desirably in an amount from 5 about 250 to about 750 ppm of the composition. Desirably, the at least one sweet taste improving polyol additive is present in an amount from about 20,000 to about 50,000 ppm of the composition and the at least one sweet taste improving organic acid additive is present in an amount from about 10 to about 5,000 ppm of the composition. In a particularly desirable embodiment, the at least one sweet taste improving polyol additive is 10 present in an amount from about 30,000 to about 40,000 ppm and the at least one sweet taste improving organic acid additive is present in an amount from about 500 to about 2,500 ppm of the composition. In a particular embodiment, a plurality of sweet taste improving organic acid additives are present in the sweetener composition in an amount from about 500 to about 2,500 ppm of the composition, the plurality of organic acid 15 additives comprising a mixture of lactic acid in an amount from about 40 to about 250 ppm, citric acid in an amount from about 150 to about 460 ppm, malic acid in an amount from about 150 to about 460 ppm, and tartaric acid in an amount from about 150 to about 460 ppm. A non-limiting example includes REBA in combination with erythritol, lactic acid, citric acid, malic acid, tartaric acid, or combinations thereof. In a particular 20 embodiment, the composition comprises 34,000 ppm of erythritol, 80 ppm of lactic acid, 310 ppm of citric acid, 310 ppm of malic acid, 310 ppm or tartaric acid, and 550 ppm of REBA. Desirably, the REBA has a purity from about 80 to about 99.5% by weight of REBA, more desirably from about 97 to about 99.5% by weight REBA in a steviolglycoside mixture. The composition optionally also may include flavorants such as 25 caramel, vanilla, or other such flavorants as described herein, or combinations thereof. In a particular embodiment, such a composition is a carbonated soft drink, such as a cola, although other types of beverages are contemplated as well. Those of ordinary skill in the art should appreciate that the amounts of the sweet taste improving organic acids in a carbonated beverage may be modified to obtain a pH from about 2.3 to about 3.5. In 30 addition, those of ordinary skill in the art also should appreciate that sweet taste improving inorganic acid additives, such as phosphoric acid, benzoic acid, and sorbic acid, may be PCT/US2006/044574 WO 2007/061795 2015203721 02M2015 101 used individually or in combination in a carbonated beverage in order'to obtain a pH from about 2.3 to about 3.5.
In another embodiment, the composition comprising REBA in combination with at least one sweet taste improving polyol additive and at least one sweet taste 5 improving organic acid additive described hereinabove further comprises at least one sweet taste improving inorganic acid additive. Desirably, at least one sweet taste improving inorganic acid additive is present in an amount from about 25 to about 5,000 ppm of the composition. Non-limiting examples of sweet taste improving inorganic acid additives include phosphoric acid, benzoic acid, sorbic acid, and combinations thereof. 10 In yet another embodiment, the composition comprising REBA in combination with at least one sweet taste improving polyol additive and at least one sweet taste improving organic acid additive described hereinabove further comprises at least one sweet taste improving inorganic acid salt additive and/or at least one sweet taste improving organic acid salt additive. Desirably, the at least one sweet taste improving inorganic acid 15 salt additive is present in an amount from about 25 to about 5,000 ppm of the composition, more desirably in an amount from about 50 to about 250 ppm, most desirably in an amount of about 150 ppm. Desirably, the at least one sweet taste improving organic acid salt additive is present in an amount from about 20 to about 10,000 ppm of the composition, more desirably in an amount from about 50 to about 350 ppm, most 20 desirably in an amount of about 148 ppm. Non-limiting examples include REBA in combination with erythritol, sodium chloride or magnesium chloride, and lactic acid, citric acid, malic acid, tartaric acid, or combinations thereof; REBA in combination with erythritol, potassium citrate or sodium citrate, and lactic acid, citric acid, malic acid, tartaric acid, or combinations thereof; or REBA in combination with erythritol, sodium 25 chloride and sodium citrate, lactic acid, citric acid, malic acid, and tartaric acid, or combinations thereof.
In another embodiment, the composition comprising REBA in combination with at least one sweet taste improving polyol additive, at least one sweet taste improving inorganic acid additive, and at least one sweet taste improving organic acid additive 30 described hereinabove further comprises at least one sweet taste improving inorganic acid salt additive and/or at least one sweet taste improving organic acid salt additive. Desirably, the at least one sweet taste improving inorganic acid salt additive is present in PCT/US2006/044574 WO 2007/061795 2015203721 02M2015 102 an amount from about 25 to about 5,000 ppm of the composition, more desirably in an amount from about 50 to about 250 ppm, most desirably in an amount of about 150 ppm. Desirably, the at least one sweet taste improving organic acid salt additive is present in an amount from about 20 to about 10,000 ppm of the composition, more desirably in an 5 amount from about 50 to about 350 ppm, most desirably in an amount of about 148 ppm. Non-limiting examples include REBA in combination with erythritol, phosphoric acid, sodium chloride or magnesium chloride, and lactic acid, citric acid, malic acid, tartaric acid, or combinations thereof; REBA in combination with erythritol, phosphoric acid, potassium citrate or sodium citrate, and lactic acid, citric acid, malic acid, tartaric acid, or 10 combinations thereof; or REBA in combination with erythritol, phosphoric acid, sodium chloride and sodium citrate, lactic acid, citric acid, malic acid, and tartaric acid, or combinations thereof.
The desired weight ratio of the NHPS to sweet taste improving composition(s) in the NHPS composition will depend on the particular NHPS, and the 15 sweetness and other characteristics desired in the final product or orally ingestible composition. NHPSs vary greatly in their potency, ranging from about 30 times more potent than sucrose to about 8,000 times more potent than sucrose on a weight basis. In general, the weight ratio of the NHPS to sweet taste improving composition may for example range from between 10,000:1 to about 1:10,000; a further non-limiting example 20 may range from about 9,000:1 to about 1:9,000; yet another example may range from about 8,000:1 to about 1:8,000; a further example may range from about 7,000:1 to about 1:7,000; another example may range from about 6,000:1 to about 1:6000; in yet another example may range from about 5,000:1 to about 1:5,000; in yet another example may range from about 4,000:1 to about 1:4,000; in yet another example may range from about 25 3,000:1 to about 1:3,000; in yet another example may range from about 2,000:1 to about 1:2,000; in yet another example may range from about 1,500:1 to about 1:1,500; in yet another example may range from about 1,000:1 to about 1:1,000; in yet another example may range from about 900:1 to about 1:900; in yet another example may range from about 800:1 to about 1:800; in yet another example may range from about 700:1 to about 1:700; 30 in yet another example may range from about 600:1 to about 1:600; in yet another example may range from about 500:1 to about 1:500; in yet another example may range from about 400:1 to about 1:400; in yet another example may range from about 300:1 to PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 103 about 1:300; in yet another example may range from about 200:1 to about 1:200; in yet another example may range from about 150:1 to about 1:150; in yet another example may range from about 100:1 to about 1:100; in yet another example may range from about 90:1 to about 1:90; in yet another example may range from about 80:1 to about 1:80; in yet 5 another example may range from about 70:1 to about 1:70; in yet another example may range from about 60:1 to about 1:60; in yet another example may range from about 50:1 to about 1:50; in yet another example may range from about 40:1 to about 1:40; in yet another example may range from about 30:1 to about 1:30; in yet another example may range from about 20:1 to about 1:20; in yet another example may range from about 15:1 to 10 about 1:15; in yet another example may range from about 10:1 to about 1:10; in yet another example may range from about 9:1 to about 1:9; in yet another example may range from about 8:1 to about 1:8; in yet another example may range from about 7:1 to about 1:7; in yet another example may range from about 6:1 to about 1:6; in yet another example may range from about 5:1 to about 1:5; in yet another example may range from about 4:1 15 to about 1:4; in yet another example may range from about 3:1 to about 1:3; in yet another example may range from about 2:1 to about 1:2; and in yet another example may be about 1:1; depending on the particular NHPS selected.
It is contemplated that the combination of at least one NHPS to at least one sweet taste improving composition may be carried out in any pH range that does not 20 materially or adversely affect the taste of a NHPS or the orally ingestible composition which comprises a NHPS. A non-limiting example of the pH range may be from about 2 to about 8. A further example includes a pH range from about 2 to about 5.
One of ordinary skill in the art may combine at least one NHPS with at least one sweet taste improving composition in any manner which does not materially or 25 adversely affect the taste of the orally ingestible composition. For example, a NHPS may be added to the orally ingestible composition before the sweet taste improving composition. In another example, a NHPS may be added to the orally ingestible composition after the sweet taste improving composition. In yet another example, a NHPS may be added to the orally ingestible composition simultaneously with the sweet taste 30 improving composition.
In another embodiment, a NHPS may be combined with the sweet taste improving composition prior to being added to the orally ingestible composition. For PCT/US2006/044574 WO 2007/061795 104 2015203721 02 Μ 2015 example, a NHPS may be in a pure, diluted, or concentrated form as a liquid (e.g., solution), solid (e.g., powder, chunk, pellet, grain, block, crystalline, or the like), suspension, gas state, or combinations thereof may be contacted with the sweet taste improving composition which may be in a pure, diluted, or concentrated form as a liquid 5 (e.g., solution), solid (e.g., powder, chunk, pellet, grain, block, crystalline, or the like), suspension, gas state, or combinations thereof before both are contacted with an orally ingestible composition. In yet another embodiment, when there are more than one NHPSs or more than one sweet taste improving composition, each component of die NHPS and sweet taste improving composition may be added simultaneously, in an alternating pattern, 10 in a random pattern, or any other pattern which will not adversely affect the taste of the orally ingestible composition. 3. Tabletop Compositions
In a particular embodiment of the present invention, the NHPS compositions comprise a tabletop sweetener composition comprising at least one NHPS in 15 combination with at least one bulking agent and optionally at least one sweet taste improving composition and/or anti-caking agent with improved temporal and/or flavor profile.
In accordance with particular embodiments, suitable “bulking agents” include maltodextrin (10 DE, 18 DE, or 5 DE), com syrup solids (20 or 36 DE), sucrose, 20 fructose, glucose, invert sugar, sorbitol, xylose, ribulose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharides, cellulose and cellulose derivatives, and the like, and mixtures thereof. Additionally, in accordance with still other embodiments of the invention, granulated sugar (sucrose) or other caloric sweeteners such 25 as crystalline fructose, other carbohydrates, or sugar alcohol can be used as a bulking agent due to their provision of good content uniformity without the addition of significant calories. In one embodiment, a bulking agent may be used as a sweet taste improving composition.
As used herein the phrase “anti-caking agent” and “flow agent” refer to any 30 composition which prevents, reduces, inhibits, or suppresses at least one natural and/or synthetic high-potency sweetener molecule from attaching, binding, or contacting to PCT/US2006/044574 WO 2007/061795 105 2015203721 02 Μ 2015 another natural and/or synthetic high-potency sweetener molecule. Alternatively, anticaking agent may refer to any composition which assists in content uniformity and uniform dissolution. In accordance with particular embodiments, non-limiting examples of anti-caking agents include cream of tartar, calcium silicate, silicon dioxide, 5 microcrystalline cellulose (Avicel, FMC BioPolymer, Philadelphia, Pennsylvania), and tricalcium phosphate. In one embodiment, the anti-caking agents are present in the tabletop functional sweetener composition in an amount from about 0.001 to about 3 % by weight of the tabletop functional sweetener composition.
Tabletop NHPS compositions are embodied and packaged in numerous 10 different forms and it is intended that the tabletop NHPS compositions of the present invention may be of any form known in the art. In accordance with particular embodiments, non-limiting examples include powder form, granular form, packets, tablets, sachets, pellets, cubes, solids, and liquids.
In an embodiment, a tabletop NHPS composition comprises a single-serving 15 (portion control) packet comprising a dry-blend of a functional sweetener formulation. Dry-blend formulations generally may comprise powder or granules. Although the tabletop NHPS composition may be in a packet of any size, an illustrative non-limiting example of conventional portion control tabletop sweetener packets are approximately 2.5 by 1.5 inches and hold approximately 1 gram of a sweetener composition having a 20 sweetness equivalent to 2 teaspoons of granulated sugar (~ 8 g). The amount of NHPS in a dry-blend tabletop NHPS formulation will vary due to the varying potency of different NHPSs. hi a particular embodiment, a dry-blend tabletop NHPS formulation may comprise a NHPS in an amount from about 1 % (w/w) to about 10 % (w/w) of the tabletop NHPS composition. 25 Solid tabletop NHPS embodiments include cubes and tablets. A non limiting example of conventional cubes are equivalent in size to a standard cube of granulated sugar, which is approximately 2.2 x 2.2 x 2.2 cm3 and weigh approximately 8 g. In one embodiment, a solid tabletop sweetener is in the form of a tablet or any other form known to those skilled in the art. 30 A tabletop NHPS composition also may be embodied in the form of a liquid, wherein the NHPS is combined with a liquid carrier. Suitable non-limiting PCT/US2006/044574 WO 2007/061795 106 examples of carrier agents for liquid tabletop functional sweeteners include water, alcohol, polyol, glycerin base or citric acid base dissolved in water, and mixtures thereof. Due to the varying potencies of the different high-potency sweeteners, the amount of high-potency sweetener in a liquid tabletop NHPS formulation will also vary. The sweetness equivalent of a tabletop NHPS composition for any of the forms described herein or known in the art may be varied to obtain a desired sweetness profile. For example, a tabletop NHPS composition may comprise a sweetness comparable to that of an equivalent amount of standard sugar. In another embodiment, the tabletop NHPS composition may comprise a sweetness of up to 100 times that of an equivalent amount of sugar. In another embodiment, the tabletop NHPS composition may comprise a sweetness of up to 90 times, 80 times, 70 times, 60 times, 50 times, 40 times, 30 times, 20 times, 10 times, 9 times, 8 times, 7 times, 6 times, 5 times, 4 times, 3 times, and 2 times that of an equivalent amount of sugar.
In one embodiment, the tabletop NHPS composition also may be formulated for targeted uses, for example, in beverage, food, pharmaceutical, cosmetics, herbal/vitamins, tobacco, and in any other products which may be sweetened. For example, a tabletop NHPS composition for baking may be formulated having additional protecting agents such as encapsulants. Other forms will be readily apparent to those skilled in the tabletop sweetener art.
Commonly used methods for making powder or granulated NHPS formulations for packets include fluid bed agglomeration processes. Other methods for making tabletop sweetener compositions are well known to those of ordinary skill in the art.
Those skilled in the art appreciate that the amount of NHPS and amount and types of sweet taste improving composition, bulking agent, and/or anti-caking agent can be modified in order to tailor the taste of the tabletop sweetener composition to a desired profile and end use.
Specific embodiments of tabletop sweetener compositions and methods of making tabletop functional sweetener compositions are disclosed in U.S. Provisional Application No. 60/805,209, entitled “Natural High-Potency Tabletop Sweetener Compositions with Improved Temporal and/or Flavor Profile, Methods for Their PCT/US2006/044574 WO 2007/061795 107 2015203721 02 Jul2015
Formulation, and Uses,” filed on June 19, 2006, by DuBois, et al., the disclosure of which is incorporated herein by reference in its entirety. 4. Orally Ingestible Sweetened Compositions
As explained hereinabove, sweetened compositions in accordance with 5 embodiments of this invention comprise a sweetenable composition, at least one NHPS and/or at least one modified NHPS, and at least one sweet taste improving composition. A multitude of suitable sweetenable compositions are described hereinabove.
Generally, the amount of NHPS present in a sweetened composition varies widely depending on the particular type of sweetened composition and its desired 10 sweetness. Those of ordinary skill in the art can readily discern the appropriate amount of sweetener to put in the sweetened composition. In a particular embodiment, the at least one NHPS is present in the sweetened composition in an amount in the range of about 1 to about 5,000 ppm of the sweetened composition, and the at least one sweet taste improving composition is present in the sweetened composition in an amount in the range of about 15 0.1 to about 100,000 ppm of the sweetened composition.
In accordance with particular embodiments, suitable amounts of NHPSs for sweetenable compositions comprise amounts in the range from about 100 ppm to about 3,000 ppm for rebaudioside A; from about 50 ppm to about 3,000 ppm for stevia; from about 50 ppm to about 3,000 ppm for stevioside; from about 50 ppm to about 3,000 ppm 20 for morgroside IV; from about 50 ppm to about 3,000 ppm for morgroside V; from about 50 ppm to about 3,000 ppm for Luo Han Guo sweetener; from about 5 ppm to about 300 ppm for monatin, from about 5 ppm to about 200 ppm for curculin; and from about 50 ppm to about 3,000 ppm for mono-ammonium glycyrrhizic acid salt hydrate.
In one particular embodiment, an orally ingestible composition comprises a 25 carbonated beverage comprising at least one NHPS and at least one sweet taste improving composition; wherein the at least one NHPS is chosen from rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, dulcoside B, rubusoside, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid 30 and its salts, thaumatin, monellin, mabinlin, brazzein, hemandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 108 A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, cyclocarioside I, or combinations thereof; and wherein the at least one sweet taste, improving composition is selected from the group consisting of carbohydrates, polyols, amino acids and their corresponding salts, polyamino acids and their corresponding salts, 5 sugar acids and their corresponding salts, organic acids, inorganic acids, organic salts, inorganic salts, bitter compounds, flavorants, astringent compounds, polymers, proteins or protein hydrolysates, surfactants, emulsifiers, flavonoids, alcohols, and combinations thereof. IV. Examples 10 The present invention is further illustrated by the following examples, which are not to be construed in any way as imposing limitations upon the scope thereof. On the contrary, it is to be clearly understood that resort may be had to various other embodiments, modifications, and equivalents thereof which, after reading the description therein, may suggest themselves to those skilled in the art without departing from the spirit 15 of the present invention and/or the scope of the appended claims. Unless otherwise specified, %’s are by weight.
A. Example A
An exemplary method of sensory evaluation is provided in the following protocol, similar to that described hereinabove. In this test protocol, none of the samples 20 were swallowed. All samples were expectorated and the mouth was rinsed with water after the tasting. In step 1, the 10% sucrose control sample was tasted by distributing ca. 10 mL of sample quickly throughout the oral cavity, wherein the maximal “Sweetness Intensity” was measured. This intensity is defined as a 10 on a 0-15 scale where 0 is defined as no perceptible sweetness and 15, the sweetness of 15% sucrose. Immediately 25 upon sensing maximal sweetness, the sample was expectorated, the mouth was rinsed with water and the rate of sweetness decay (“Sweetness Linger”) was measured, where attention was focused on the sweetness 3-4 min after the water rinse. The sweetness linger was rated by a panel of experts in the sensory evaluation of foods and beverages using the following scale: 0 = no sweetness linger, 1 = very slight sweetness linger, 2 = slight 30 sweetness linger, 3 = moderate sweetness linger, 4 = moderately high sweetness linger, 5 = high sweetness linger. After sample tasting was complete, a salty oyster cracker was PCT/US2006/044574 WO 2007/061795 109 2015203721 02 Μ 2015 chewed followed by a water rinse, and at least 5 minutes followed before tasting the next sample.
The “Sweetness Linger” rating for sucrose observed by this protocol was defined as 0. Experimental samples were tasted by the same protocol, always allowing 5 sufficient time between samples to ensure re-equilibration of the sensory system. Retasting of control samples during the course of the experiment was allowed and encouraged.
The comparison taste test was performed between two controls and addition of sweet taste improving additive on the onset and/or sweetness linger.
10 B. Example Set B
Where there are ranges provided in the examples, a number of beverages comprising the NHPS, such as rebaudioside-A (REBA), were made 5-7 levels from the top to the bottom range, using a 1:1 dilution of the corresponding sweet taste improving compositions. The sweetness linger rating reported was the most sugar-like in sweetness 15 linger (the lowest numerical value) attained of all the samples (i.e., the shortest sweetness linger). The tasting protocol and sensory scores described in the exemplary protocol of Example A were used in the Examples of Set B.
Control Samples REBA is a natural non-caloric sweetener with a very clean flavor profile 20 (i.e., only sweet) and an acceptable sweetness onset rate but with a sweetness which lingers quite noticeably more than that of carbohydrate sweeteners.
The effects of formulation change on the sweetness linger of 400 ppm REBA (equivalent to 8 g sucrose) in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage were evaluated. The sweetness linger rating of this 25 solution was determined to be 5. 8 g of sugar was dissolved in 100 ml of citrate buffer. The sweetness linger rating of this control sample was determined to be 0. 30 WO 2007/061795 2015203721 02 Μ 2015 PCT/US2006/044574 110
Example B1 400 mg of REBA was dissolved in a citrate buffer. 35 g of erythritol was then mixed with the base solution. The sweetness linger rating of this solution was determined to be 1. 5 Example B2 400 mg of REBA was dissolved in a citrate buffer. 10 g of D-Tagatose was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example B3 10 180 ppm of REBA was dissolved in a citrate buffer. 70 g of HFCS 55 was then mixed with the base solution. The sweetness linger of this solution was determined to be 1.
Example B4 400 ppm of REBA was dissolved in a citric acid/potassium citrate matrix 15 equivalent to that in a diet lemon-lime beverage. 1,175 ppm of choline chloride was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example B5 400 ppm of REBA was dissolved in a citric acid/potassium citrate 20 composition equivalent to that in a diet lemon-lime beverage. 7,500 ppm of D-tagatose was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example B6 400 ppm of REBA was dissolved in a citric acid/potassium citrate 25 composition equivalent to that in a diet lemon-lime beverage. 10,000 ppm of D-tagatose was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 111
Example B7 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 64 ppm of mono sodium glutamate was then mixed with the base solution. The sweetness linger of this solution 5 was determined to be 4.
Example B8 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 1.2 ppm of viridiflorol was then mixed with the base solution. The sweetness linger of this solution was determined 10 to be 3.
Example B 9 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 25 ppm of naringin was then mixed with the base solution. The sweetness linger of this solution was determined 15 to be 3.
Example B10 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 25 ppm of AMP was then mixed with the base solution. The sweetness linger of this solution was determined to be 20 3.
Example Bll 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 800 ppm of malic acid was then mixed with the base solution. The sweetness linger of this solution was determined 25 to be 4.
Example B12 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 1 ppm of quinine was then WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 112 mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example B13 400 ppm REBA was dissolved in a citric acid/potassium citrate composition 5 equivalent to that in a diet lemon-lime beverage. 150 ppm of sodium chloride was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example B14 400 ppm of REBA was dissolved in a citric acid/potassium citrate 10 composition equivalent to that in a diet lemon-lime beverage. 500 ppm of sodium gluconate was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example B15 400 ppm of REBA was dissolved in a citric acid/potassium citrate 15 composition equivalent to that in a diet lemon-lime beverage. 100 ppm of D/L alanine was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example B16 400 ppm of REBA was dissolved in a citric acid/potassium citrate 20 composition equivalent to that in a diet lemon-lime beverage. 1,250 ppm of trehalose was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example B17 400 ppm of REBA was dissolved in a citric acid/potassium citrate 25 composition equivalent to that in a diet lemon-lime beverage. 250 ppm of 2,4-dihydroxybenzoic acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 113
Example B18 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 100 ppm of theanine was then mixed with the base solution. The sweetness linger of this solution was determined 5 to be 3.
Example B19 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 112 ppm of caffeic acid was then mixed with the base solution. The sweetness linger of this solution was 3. 10 Example B20 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 10,000 ppm of fructooligosaccharides was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. 15 Example B21 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 10,000 ppm fructooligosaccharide (55%) was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. 20 Example B22 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 150 ppm of potassium chloride was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. 25 Example B23 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 300 ppm of potassium dihydrogenphosphate was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. 2015203721 02 Jul2015 WO 2007/061795 PCT/US2006/044574 114
Example B24 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 125 ppm of potassium tartrate was then mixed with the base solution. The sweetness linger of this solution was 5 determined to be 3.
Example B25 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 200 ppm of sodium tartrate was then mixed with the base solution. The sweetness linger of this solution was 10 determined to be 3.
Example B26 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 400 ppm of acacia Senegal was then mixed with the base solution. The sweetness linger of this solution was 15 determined to be 2.
Example B27 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 200 ppm acacia Senegal was then mixed with the base solution. The sweetness linger of this solution was determined 20 to be 3.
Example B28 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 400 ppm of Fibergum was then mixed with the base solution. The sweetness linger of this solution was determined 25 to be 2.
Example B29 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 100 ppm of chlorogenic PCT/US2006/044574 WO 2007/061795 115 2015203721 02 Jul2015 acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example B30 400 ppm of REBA was dissolved in a citric acid/potassium citrate 5 composition equivalent to that in a diet lemon-lime beverage. 2,500 ppm of ethanol was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example B31 400 ppm of REBA was dissolved in a citric acid/potassium citrate 10 composition equivalent to that in a diet lemon-lime beverage. 2,500 ppm of taurine was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example B32 400 ppm of REBA was dissolved in a citric acid/potassium citrate 15 composition equivalent to that in a diet lemon-lime beverage. 625 ppm of propylene glycol was then mixed with the base solution. The sweetness linger of this solution was 4.
Example B33 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 5,000 ppm of glycine was 20 then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example B34 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. β-Cyclodextrin was then 25 mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example B35 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 2,500 ppm β-Cyclodextrin PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 116 was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Examples B36-B40 were 50% calorie-reduced products that were prepared by diluting commercially available products 1:1 with a 360 ppm REBA/citrate 5 composition. The resulting products contained 180 ppm REBA (equivalent to 5% sucrose), and were compared to the products diluted 1:1 with a 10% sucrose/citrate composition (to compare the products at similar flavor levels).
Example B36
Commercially available Nestea Cool lemon Iced Tea product was diluted 10 1:1 with a 360 ppm REBA/citrate composition. This gave a product that contained 180 ppm REBA (equivalent to 5% sucrose). This product was compared to the commercially available Nestea Cool Lemon Iced Tea. The REBA product was very similar to the corresponding sucrose products in flavor and taste. The sweetness linger of this solution was determined to be 1. 15 Example B37
Commercially available Welch’s 100% Grape Juice product was diluted 1:1 with a 360 ppm REBA/citrate composition. This gave a product that contained 180 ppm REBA (equivalent to 5% sucrose). This product was compared to the commercially available Welch’s 100% Grape Juice. The REBA product was very similar to the 20 corresponding sucrose products in flavor and taste. The sweetness linger of this solution was determined to be 1.
Example B38
Commercially available Minute Maid Apple Juice 100% juice product was diluted 1:1 with a 360 ppm REBA/citrate composition. This gave a product that contained 25 180 ppm REBA (equivalent to 5% sucrose). This product was compared to the commercially available Minute Maid Apple Juice 100% juice. The REBA product was very similar to the corresponding sucrose products in flavor and taste. The sweetness linger of this solution was determined to be 1. 30 WO 2007/061795 2015203721 02M2015 PCT/US2006/044574 117
Example B39
Cominercially available Minute Maid Cranberry/Apple/Raspberry 25% juice product was diluted 1:1 with a 360 ppm REBA/citrate composition. This gave a product that contained 180 ppm REBA (equivalent to 5% sucrose). This product was 5 compared to the commercially available Minute Maid Cranberry/Apple/Raspberry 25% juice. The REBA product was very similar to the corresponding sucrose products in flavor and taste. The sweetness linger of this solution was determined to be 1.
Example B40
Commercially available Minute Maid Cranberry/Grape 25% juice product 10 was diluted 1:1 with a 360 ppm REBA/citrate composition. This gave a product that contained 180 ppm REBA (equivalent to 5% sucrose). This product was compared to the commercially available Minute Maid Cranberry/Grape 25% juice. The REBA product was very similar to the corresponding sucrose products in flavor and taste. The sweetness linger of this solution was determined to be 1. 15 Example B41 A 500 ppm REBA sweetened diet lemon-lime beverage (sweetness level 10% sucrose equivalent) was prepared. The sweetness linger of this product was determined to be 5.
Example B42 20 A 400 ppm REBA sweetened diet lemon-lime beverage (sweetness level 10% sucrose equivalent) was prepared with 3.5% erythritol. The sweetness linger of this product was determined to be 2.
Example B43 A 180 ppm REBA sweetened diet lemon-lime beverage (sweetness level 25 10% sucrose equivalent) was prepared with 8% erythritol. The sweetness linger of this product was determined to be 1. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 118
Example B44 A 180 ppm REBA sweetened diet lemon-lime beverage (sweetness level 10% sucrose equivalent) was prepared with 3.3% sucrose and 3.5% erythritol. The sweetness linger of this product was determined to be 1. 5 Example B45 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 400 ppm of Fibergum-P (e.g., gum acacia Senegal) was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. 10 Example B46 500 ppm of REBA was dissolved in one liter citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 100 ppm to 300 ppm of poly-L-a-lysine, MW 83,000, was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. 15 Example B47 5% sucrose (weight by volume of the final product) and 80 ppm REBA were dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. 3.5% erythritol was then mixed with the base solution. The sweetness linger of this solution was determined to be 0. 20 Example B48 5% sucrose (weight by volume of the final product) and 180 ppm of REBA were dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. The sweetness linger of this solution was determined to be 2.
Example B49
25 5% sucrose (weight by volume of the final product) and 80 ppm of REBA were dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. 0.75% D-tagatose was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. 2015203721 02 Jul2015 WO 2007/061795 PCT/US2006/044574 119
Example B50 5% sucrose (weight by volume of the final product) and 80 ppm of REBA were dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. 3.5% erythritol and 0.75% D-tagatose were then mixed with the base 5 solution. The sweetness linger of this solution was determined to be 0.
Example B51 3.3% sucrose (weight by volume of the final product) and 160 ppm of REBA were dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. 3.5% erythritol was then mixed with the base solution. The 10 sweetness linger of this solution was determined to be 1.
Example B52 3.3% sucrose (weight by volume of the final product) and 160 ppm of REBA were dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. 3.5% erythritol and 0.75% D-tagatose were then mixed with the 15 base solution. The sweetness linger of this solution was determined to be 1.
Example B53 3.3% sucrose and 280 ppm of REBA were dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. The sweetness linger of this solution was determined to be 0. 20 Example B54 360 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 3.5% erythritol, 0.75% glycine, 250 ppm of potassium chloride and 650 ppm of potassium dihydrogen phosphate were then mixed with the base solution. The sweetness linger of this solution was 25 determined to be 2.
Example B55 480 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 0.75% glycine, 250 ppm of PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 120 potassium chloride and 650 ppm of potassium dihydrogen phosphate were then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example B56 320 ppm of REBA was dissolved in a citric acid/potassium citrate 5 composition equivalent to that in a diet lemon-lime beverage. 3.5% erythritol, 0.75% fructose, 250 ppm of potassium chloride and 650 ppm of potassium dihydrogen phosphate were then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example B57 10 450 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 0.75% fructose, 250 ppm of potassium chloride and 650 ppm potassium dihydrogen phosphate were then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example B58 15 360 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 3.5% erythritol and 400 ppm of Fibergum-P (e.g., gum acacia Senegal) were then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example B59 20 480 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 400 ppm of Fibergum-P (e.g., gum acacia Senegal) was then mixed with the base .solution. The sweetness linger of this solution was determined to be 3.
Example B60 25 360 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 3.5% erythritol, 0.5% glycine, 0.25% alanine, 250 ppm of potassium chloride and 650 ppm of potassium dihydrogen phosphate were then mixed with the base solution. The sweetness linger of this solution was determined to be 1. WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 121
Example B61 480 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 0.5% glycine, 0.25% alanine, 250 ppm of potassium chloride and 650 ppm of potassium dihydrogen phosphate 5 were then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example B62 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 2,500 ppm of creatine was 10 then mixed with the base solution. The sweetness linger of this solution was determined to be 2. This formulation was found to have sugar-like taste characteristics.
Example B63 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 250-500 ppm of L-sodium 15 lactate was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example B64
Two solutions were prepared. In each, 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime 20 beverage. 78 ppm to 156 ppm and 1,250 ppm of soluble rice protein were then mixed with their respective base solutions. The sweetness linger of these solutions was determined to be 3. These formulations were found to have sugar-like taste characteristics.
Example B65 400 ppm of REBA was dissolved in a citric acid/potassium citrate 25 composition equivalent to that in a diet lemon-lime beverage. 312 ppm to 625 ppm of soluble rice protein was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. This formulation was found to have sugar-like taste characteristics. WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 122
Example B 66 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 1,000 ppm to 2,000 ppm of polypropylene glycol alginate (PGA) was then mixed with the base solution. The 5 sweetness linger of this solution was determined to be 5. This formulation was found to have sugar-like taste characteristics.
Example B67 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 5,000 ppm Glycerin was 10 then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example B68 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 2,500 ppm of Fibersol-2 15 was then mixed with the base solution. The sweetness linger of this solution was determined to be 1.
Example B69 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 125 ppm collagen 20 (unflavored gelatin) was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. This formulation was found to have sugar-like taste characteristics.
Example B70 400 ppm of REBA was dissolved in a citric acid/potassium citrate 25 composition equivalent to that in a diet lemon-lime beverage. 2,000 ppm collagen (unflavored gelatin) was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. This formulation was found to have sugar-like taste characteristics. 123 2015203721 02 Jul2015 WO 2007/061795 PCT/US2006/044574
Example B71 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 125 ppm of enzyme modified rutin Sanmelin™ AO (San-Ei Gen F.F.I., Inc., Osaka, Japan) was then mixed 5 with the base solution. The sweetness linger of this solution was determined to be 4. This formulation was found to have sugar-like taste characteristics.
Example B72 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 250 ppm of enzyme 10 modified rutin Sanmelin™ AO (San-Ei Gen F.F.I., Inc., Osaka, Japan) was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example B73 400 ppm of REBA was dissolved in a citric acid/potassium citrate 15 composition equivalent to that in a diet lemon-lime beverage. 625 ppm of grape skin extract was then mixed with the base solution. The sweetness linger of this solution was determined to be 4. This formulation was found to have sugar-like taste characteristics.
Example B74 400 ppm of REBA was dissolved in a citric acid/potassium citrate 20 composition equivalent to that in a diet lemon-lime beverage. 625 ppm of Symrise™ Natural Flavor Mask for Sweeteners, 164126 (Symrise™, Holzminden, Germany) was then mixed with the base solution. The sweetness linger of this solution was determined to be 4. This formulation was found to have sugar-like taste characteristics.
Example B75 25 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 1,250 ppm to 2,500 ppm of Symrise™ Natural Flavor Mask for Sweeteners 164126 (Symrise™, Holzminden, Germany) was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. This formulation was found to have sugar-like taste 30 characteristics. PCT/US2006/044574 WO 2007/061795 124 2015203721 02 Μ 2015
Example B76 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 2 ppm of Natural Advantage™ Bitterness Blocker 9 (Natural Advantage, Freehold, New Jersey, U.S.A.) 5 was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. This formulation was found to have sugar-like taste characteristics.
Example B77 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 1 ppm to 2 ppm of Natural 10 Advantage™ Bitterness Blocker 2 (Natural Advantage, Freehold, New Jersey, U.S.A.) was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example B78 400 ppm of REBA was dissolved in a citric acid/potassium citrate 15 composition equivalent to that in a diet lemon-lime beverage. 2 ppm of Natural Advantage™ Bitterness Blocker 1 (Natural Advantage, Freehold, New Jersey, U.S.A.) was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example B79 20 400 ppm of REBA was dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. 4 ppm to 8 ppm of Natural Advantage™ Bitterness Blocker 10 (Natural Advantage, Freehold, New Jersey, U.S.A.) was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
25 C. Example Set C
Control Samples 375 mg of mono-ammonium glycyrrhizic acid salt hydrate (sweetness level 4% sucrose equivalent) was dissolved in one liter of carbon-treated water. The sweetness linger of this solution was determined to be 5. WO 2007/061795 2015203721 02 Μ 2015 PCT/US2006/044574 125 10 g of sucrose was dissolved in 100 ml of carbon treated water. The sweetness linger rating of this control sample was determined to be 0.
Example Cl 375 mg of monoammonium glycyrrhizic acid salt hydrate, was dissolved in 5 one liter of carbon-treated water. 50,000 ppm of NaCl was then mixed with the base solution. The sweetness linger of this solution was determined to be 1.
Example C2 375 mg of monoammonium glycyrrhizic acid salt hydrate, was dissolved in one liter of carbon-treated water.. 25,000 ppm of NaCl was then mixed with the base 10 solution. The sweetness linger of this solution was determined to be 2.
Example C3 375 mg of mono-ammonium glycyrrhizic acid salt hydrate, was dissolved in one liter of carbon-treated water. 10,000 ppm of NaCl was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. 15 Example C4 375 mg of mono-ammonium glycyrrhizic acid salt hydrate, was dissolved in one liter of carbon-treated water. 5,000 ppm of NaCl was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.5.
D. Example Set D 20
Example D1 400-500 ppm of stevia are dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution. 25 Example D2 5% sucrose and 400-500 ppm stevia are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 126
Example D3 5% sucrose and 400-500 ppm of stevia are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. D-Tagatose is then mixed with the base solution. 5 Example D4 5% sucrose and 400-500 ppm of stevia are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution.
Example D5 10 3.3% sucrose and 400-500 ppm of stevia are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution.
Example D6 3.3% sucrose and 400-500 ppm of stevia are dissolved in a citric 15 acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution.
Example D7 3.3% sucrose and 400-500 ppm of stevia are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. 20 Example D8 400-500 ppm of stevia is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. 25 Example D9 400-500 ppm of stevia is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Glycine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 127
Example DIO 400-500 ppm of stevia is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, fructose, potassium chloride and potassium dihydrogen phosphate are then mixed with the base 5 solution.
Example Dll 400-500 ppm of stevia is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fructose, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. 10 Example D12 400-500 ppm of stevia is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol and fibergum (e.g., gum acacia seyal) are then mixed with the base solution.
Example D13 15 400-500 ppm of stevia is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution.
Example D14 400-500 ppm of stevia is dissolved in a citric acid/potassium citrate 20 composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D15 400-500 ppm of stevia is dissolved in a citric acid/potassium citrate 25 composition equivalent to that in a diet lemon-lime beverage. Glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 128
Example D16 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid is then mixed with the base solution. 5 Example D17 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid, potassium salt is then mixed with the base solution.
Example D18 10 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-threonine is then mixed with the base solution.
Example D19 400-500 mg of stevia is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-serine is then mixed with the base solution.
Example D20 400-500 mg of stevia is dissolved in one liter carbon-treated water and add phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. L-alanine is then 20 mixed with the base solution.
Example D21 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Glycine is then mixed with the base solution. 25 Example D22 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached, β-alanine is then mixed with the base solution. 2015203721 02M2015 WO 2007/061795 PCT/US2006/044574 129
Example D23 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-a-lysine are then mixed with the base solution. 5 Example D24 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-e-lysine are then mixed with the base solution,
Example D25 10 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Adipic acid is then mixed with the base solution.
Example D26 400-500 mg of stevia is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 63,000) is then mixed with the base solution.
Example D27 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine 20 (molecular weight ~ 6,000) is then mixed with the base solution.
Example D28 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 83,000) is then mixed with the base solution. 25 Example D29 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 1,300,000) is then mixed with the base solution. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 130
Example D30 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Fruitaric acid is 5 then mixed with the base solution.
Example D31 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Tartaric acid is then mixed with the base solution. 10 Example D32 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Sodium bisulfate is then mixed with the base solution.
Example D33 15 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Laurie arginate is then mixed with the base solution.
Example D34 400-500 mg of stevia is dissolved in one liter carbon-treated water and 20 phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. L-lysine is then mixed with the base solution.
Example D35 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Guanidine 25 hydrochloride is then mixed with the base solution. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 131
Example D36 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Urea and sodium chloride are then mixed with the base solution. 5 Example D37 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Urea is then mixed with the base solution.
Example D38 10 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Choline chloride is then mixed with the base solution.
Example D39 400-500 mg of stevia is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. D-glucosamine hydrochloride is then mixed with the base solution.
Example D40 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Poly-L-e-lysine is 20 then mixed with the base solution.
Example D41 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Glycine, sodium chloride and potassium chloride are then mixed with the base solution. 25 PCT/US2006/044574 WO 2007/061795 132 2015203721 02M2015
Example D42 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Glycine and aluminum sulfate (alum) are then mixed with the base solution. 5 Example D43 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Glycine and potassium chloride are then mixed with the base solution.
Example D44 10 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Glycine and sodium gluconate are then mixed with the base solution.
Example D45 400-500 mg of stevia is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Polyethylenimine is then mixed with the base solution.
Example D46 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Chitosan is then 20 mixed with the base solution.
Example D47 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Poly L-omithine is then mixed with the base solution. 25 Example D48 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Magnesium chloride is then mixed with the base solution. WO 2007/061795 2015203721 02 Μ 2015 PCT/US2006/044574 133
Example D49 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Whey protein (concentrate 34%) is then mixed with the base solution. 5 400-500 mg of stevia is dissolved in one liter carbon-treated water and phosphoric acid (75%) until a pH between pH 2.4 and 2.5 is reached. Fumaric acid, malic acid and tartaric acid are then mixed with the base solution.
Example D50 400-500 ppm of stevioside is dissolved in a citric acid/potassium citrate 10 composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution.
Example D51 5% sucrose and 400-500 ppm stevioside are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol 15 is then mixed with the base solution.
Example D52 5% sucrose and 400-500 ppm of stevioside are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. D-Tagatose is then mixed with the base solution. 20 Example D53 5% sucrose and 400-500 ppm of stevioside are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution.
Example D54 25 3.3% sucrose and 400-500 ppm of stevioside are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 134
Example D55 3.3% sucrose and 400-500 ppm of stevioside are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution. 5 Example D56 400-500 ppm of stevioside are dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. 10 Example D57 400-500 ppm of stevioside is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Glycine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D58 15 400-500 ppm of stevioside is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, fructose, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D59 20 400-500 ppm of stevioside is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fructose, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D60 400-500 ppm of stevioside is dissolved in a citric acid/potassium citrate 25 composition equivalent to that in a diet lemon-lime beverage. Erythritol and fibergum (e.g., gum acacia seyal) are then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 135 2015203721 02 Μ 2015
Example D61 400-500 ppm of stevioside is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution. 5 Example D62 400-500 ppm of stevioside is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. 10 Example D63 400-500 ppm of stevioside is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D64 15 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid is then mixed with the base solution.
Example D65 400-500 mg of stevioside is dissolved in one liter carbon-treated water and 20 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid, potassium salt is then mixed with the base solution.
Example D66 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-25 Threonine is then mixed with the base solution.
Example D67 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached L-serine is then mixed with the base solution. WO 2007/061795 PCT/US2006/044574 136
Example D68 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-alanine is then mixed with the base solution.
Example D69 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine is then mixed with the base solution.
Example D70 400-500 mg of stevioside is dissolved in one liter carbon-treated, water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached., β-alanine is then mixed with the base solution.
Example D71 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-a-lysine are then mixed with the base solution.
Example D72 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-e-lysine are then mixed with the base solution.
Example D73 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Adipic acid is then mixed with the base solution.
Example D74 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 63,000) is then mixed with the base solution. 2015203721 02 Jul2015 WO 2007/061795 PCT/US2006/044574 137
Example D75 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 6,000) is then mixed with the base solution. 5 Example D76 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 93,000) is then mixed with the base solution.
Example D77 10 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 1,300,000) is then mixed with the base solution.
Example D78 400-500 mg of stevioside is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Fruitaric acid is then mixed with the base solution.
Example D79 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric add (75%) is added until a pH between pH 2.4 and 2.5 is reached Tartaric 20 acid is then mixed with the base solution.
Example D80 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Sodium bisulfate is then mixed with the base solution. 25 Example D81 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Laurie arginate is then mixed with the base solution. 2015203721 02 Jul2015 WO 2007/061795 PCT/US2006/044574 138
Example D82 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-lysine is then mixed with the base solution. 5 Example D83 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Guanidine hydrochloride is then mixed with the base solution.
Example D84 10 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Urea and sodium chloride are then mixed with the base solution.
Example D85 400-500 mg of stevioside is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Urea is then mixed with the base solution.
Example D86 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Choline 20 chloride is then mixed with the base solution.
Example D87 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-glucosamine hydrochloride is then mixed with the base solution. 25 Example D88 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-ε-lysine is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 139
Example D89 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine, sodium chloride and potassium chloride are then mixed with the base solution. 5 Example D90 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached.. Glycine and aluminum sulfate (alum) are then mixed with die base solution.
Example D9l 10 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and potassium chloride are then mixed with the base solution.
Example D92 400-500 mg of stevioside is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and sodium gluconate are then mixed with the base solution.
Example D93 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. 20 Polyethylenimine is then mixed with the base solution.
Example D94 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Chitosan is then mixed with the base solution. 25 Example D95 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly L-omithine is then mixed with the base solution. WO 2007/061795 PCT/US2006/044574 140
Example D 96 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Magnesium chloride is then mixed with the base solution.
Example D97 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Whey protein (concentrate 34%) is then mixed with the base solution. 400-500 mg of stevioside is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Fumaric acid, malic acid and tartaric acid are then mixed with the base solution.
Example D98 400-500 ppm of Mogroside IV is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution.
Example D99 5% sucrose and 400-500 ppm Mogroside IV are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution.
Example D100 5% sucrose and 400-500 ppm of Mogroside IV are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage.
Example D101 5% sucrose and 400-500 ppm of Mogroside IV are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. D-Tagatose is then mixed with the base solution. PCT/U S2006/044574 WO 2007/061795 141 2015203721 02 Jul2015
Example D102 5% sucrose and 400-500 ppm of Mogroside IV are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution. 5 Example D103 3.3% sucrose and 400-500 ppm of Mogroside IV are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution.
Example D104 10 3.3% sucrose and 400-500 ppm of Mogroside IV are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution.
Example D105 3.3% sucrose and 400-500 ppm of Mogroside IV are dissolved in a citric 15 acid/potassium citrate composition equivalent to that in a lemon-lime beverage.
Example D106 400-500 ppm of Mogroside IV is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base 20 solution.
Example D107 400-500 ppm of Mogroside IV is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Glycine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. 25 Example D108 400-500 ppm of Mogroside IV is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol. fructose, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. 142 2015203721 02 Jul2015 WO 2007/061795 PCT/US2006/044574
Example D109 400-500 ppm of Mogroside IV is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fructose, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
5 Example DUO 400-500 ppm of Mogroside IV is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol and fibergum (e.g., gum acacia seyal) are then mixed with the base solution.
Example Dill 10 400-500 ppm of Mogroside IV is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution.
Example D112 400-500 ppm of Mogroside IV is dissolved in a citric acid/potassium citrate 15 composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D113 400-500 ppm of Mogroside IV is dissolved in a citric acid/potassium citrate 20 composition equivalent to that in a diet lemon-lime beverage. Glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D114 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-25 Gluconic acid is then mixed with the base solution.
Example D115 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid, potassium salt is then mixed with the base solution. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 143
Example D116 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-Threonine is then mixed with the base solution. 5 Example D117 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-Serine is then mixed with the base solution.
Example D118 10 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-alanine is then mixed with the base solution.
Example D119 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water 15 and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine is then mixed with the base solution.
Example D120 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached, β-20 alanine is then mixed with the base solution.
Example D121 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-a-lysine are then mixed with the base solution. 25 Example D122 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-e-lysine are then mixed with the base solution. 2015203721 02 Jul2015 WO 2007/061795 PCT/US2006/044574 144
Example D123 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Adipic acid is then mixed with the base solution. 5 Example D124 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 63,000) is then mixed with the base solution.
Example D125 10 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 6,000) is then mixed with the base solution.
Example D126 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water 15 and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-l^a-lysine (molecular weight ~ 93,000) is then mixed with the base solution.
Example D127 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-20 L-a-lysine (molecular weight ~ 1,300,000) is then mixed with the base solution.
Example D128 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Fruitaric acid is then mixed with the base solution. 25 Example D129 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Tartaric acid is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 145
Example D130 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Sodium bisulfate is then mixed with the base solution. 5 Example D131 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Laurie arginate is then mixed with the base solution.
Example D132 10 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-lysine is then mixed with the base solution.
Example D133 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water 15 and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Guanidine hydrochloride is then mixed with the base solution.
Example D134 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Urea 20 and sodium chloride are then mixed with the base solution.
Example D135 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Urea is then mixed with the base solution. 25 Example D136 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Choline chloride is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 146
Example D137 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-glucosamine hydrochloride is then mixed with the base solution. 5 Example D138 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-s-lysine is then mixed with the base solution.
Example D139 10 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine, sodium chloride and potassium chloride are then mixed with the base solution.
Example D140 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water 15 and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and aluminum sulfate (alum) are then mixed with the base solution.
Example D141 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine 20 and potassium chloride are then mixed with the base solution.
Example D142 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and sodium gluconate are then mixed with the base solution. 25 Example D143 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Polyethylenimine is then mixed with the base solution. WO 2007/061795 PCT/US2006/044574 147
Example D144 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Chitosan is then mixed with the base solution.
Example D145 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly L-omithine is then mixed with the base solution.
Example D146 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Magnesium chloride is then mixed with the base solution.
Example D147 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Whey protein (concentrate 34%) is then mixed with the base solution.
Example D148 400-500 mg of Mogroside IV is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Fumaric acid, malic acid and tartaric acid are then mixed with the base solution.
Example D149 400-500 ppm of Mogroside V is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution.
Example D150 5% sucrose and 400-500 ppm Mogroside V are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution. 2015203721 02 Jul2015 WO 2007/061795 PCT/US2006/044574 148
Example D151 5% sucrose and 400-500 ppm of Mogroside V are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. D-Tagatose is then mixed with the base solution. 5 Example D152 5% sucrose and 400-500 ppm of Mogroside V are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution.
Example D153 10 3.3% sucrose and 400-500 ppm of Mogroside V are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution.
Example D154 3.3% sucrose and 400-500 ppm of Mogroside V are dissolved in a citric 15 acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution.
Example D155 3.3% sucrose and 400-500 ppm of Mogroside V are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. 20 Example D156 400-500 ppm of Mogroside V is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. 25 Example D157 400-500 ppm of Mogroside V is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Glycine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 149
Example D158 400-500 ppm of Mogroside V is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, fructose, potassium chloride and potassium dihydrogen phosphate are then mixed with the base 5 solution.
Example D159 400-500 ppm of Mogroside V is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fructose, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. 10 ExampleD160 400-500 ppm of Mogroside V is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol and fibergum (e.g., gum acacia seyal) are then mixed with the base solution.
Example D161 15 400-500 ppm of Mogroside V is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution.
Example D162 400-500 ppm of Mogroside V is dissolved in a citric acid/potassium citrate 20 composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D163 400-500 ppm of Mogroside V is dissolved in a citric acid/potassium citrate 25 composition equivalent to that in a diet lemon-lime beverage. Glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 150 2015203721 02 Μ 2015
Example D164 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid is then mixed with the base solution. 5 Example D165 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid, potassium salt is then mixed with the base solution.
Example D166 10 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-Threonine is then mixed with the base solution.
Example D167 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water 15 and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-Serine is then mixed with the base solution.
Example D168 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-20 alanine is then mixed with the base solution.
Example D169 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine is then mixed with the base solution. 25 Example D170 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached, β-alanine is then mixed with the base solution. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 151
Example D171 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-a-lysine are then mixed with the base solution. 5 Example D172 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-s-lysine are then mixed with the base solution.
Example D173 10 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Adipic acid is then mixed with the base solution.
Example D174 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water 15 and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 63,000) is then mixed with the base solution.
Example D175 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-20 L-oc-lysine (molecular weight ~ 6,000) is then mixed with the base solution.
Example D176 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 93,000) is then mixed with the base solution. 25 Example D177 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 1,300,000) is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 152
Example D178 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Fruitaric acid is then mixed with the base solution. 5 Example D179 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Tartaric acid is then mixed with the base solution.
Example D180 10 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Sodium bisulfate is then mixed with the base solution.
Example D181 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water 15 and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Laurie arginate is then mixed with the base solution.
Example D182 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-20 lysine is then mixed with the base solution.
Example D183 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Guanidine hydrochloride is then mixed with the base solution. 25 Example D184 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Urea and sodium chloride are then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02M2015 153
Example D185 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Urea is then mixed with the base solution. 5 Example D186 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Choline chloride is then mixed with the base solution.
Example D187 10 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-glucosamine hydrochloride is then mixed with the base solution.
Example D188 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water 15 and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-s-lysine is then mixed with the base solution.
Example D189 400-500 mg of Mogroside Y is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. 20 Glycine, sodium chloride and potassium chloride are then mixed with the base solution.
Example D190 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and aluminum sulfate (alum) are then mixed with the base solution. 25 Example D191 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and potassium chloride are then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 154 2015203721 02 Jul2015
Example D192 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and sodium gluconate are then mixed with the base solution. 5 Example D193 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Polyethylenimine is then mixed with the base solution.
Example D194 10 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Chitosan is then mixed with the base solution.
Example D195 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water 15 and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly L-omithine is then mixed with the base solution.
Example D196 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. 20 Magnesium chloride is then mixed with the base solution.
Example D197 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Whey protein (concentrate 34%) is then mixed with the base solution. 25 Example D198 400-500 mg of Mogroside V is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Fumaric acid, malic acid and tartaric acid are then mixed with the base solution. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 155
Example D199 400-500 ppm of Luo Han Guo sweetener is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution. 5 Example D200 5% sucrose and 400-500 ppm of Luo Han Guo sweetener are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution.
Example D201 10 5% sucrose and 400-500 ppm of Luo Han Guo sweetener are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage.
Example D202 5% sucrose and 400-500 ppm of Luo Han Guo sweetener are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. D-15 Tagatose is then mixed with the base solution.
Example D203 5% sucrose and 400-500 ppm of Luo Han Guo sweetener are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution. 20 Example D204 3.3% sucrose and 400-500 ppm of Luo Han Guo sweetener are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution.
Example D205 25 3.3% sucrose and 400-500 ppm of Luo Han Guo sweetener are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution. 2015203721 02Jul2015 WO 2007/061795 PCT/US2006/044574 156
Example D206 400-500 ppm of Luo Han Guo sweetener is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, potassium chloride and potassium dihydrogen phosphate are then 5 mixed with the base solution.
Example D207 400-500 ppm of Luo Han Guo sweetener is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Glycine, potassium chloride and potassium dihydrogen phosphate are then mixed with the 10 base solution.
Example D208 400-500 ppm of Luo Han Guo sweetener is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, fructose, potassium chloride and potassium dihydrogen phosphate are then 15 mixed with the base solution.
Example D209 400-500 ppm of Luo Han Guo sweetener is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fructose, potassium chloride and potassium dihydrogen phosphate are then mixed with the 20 base solution.
Example D210 400-500 ppm of Luo Han Guo sweetener is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol and fibergum (e.g., gum acacia seyal) are then mixed with the base solution. 25 Example D211 400-500 ppm of Luo Han Guo sweetener is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution. WO 2007/061795 2015203721 02 Μ 2015 PCT/US2006/044574 157
Example D212 400-500 ppm of Luo Han Guo sweetener is dissolved in a citric acidypotassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, alanine, potassium chloride and potassium dihydrogen phosphate are 5 then mixed with the base solution.
Example D213 400-500 ppm of Luo Han Guo sweetener is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed 10 with the base solution.
Example D214 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid is then mixed with the base solution. 15 Example D215 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid, potassium salt is then mixed with the base solution.
Example D216 20 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon- treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-threonine is then mixed with the base solution.
Example D217 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-25 treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-Serine is then mixed with the base solution. WO 2007/061795 2015203721 02 M2015 PCT/US2006/044574 158
Example D218 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-alanine is then mixed with the base solution. 5 Example D219 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine is then mixed with the base solution.
Example D220 10 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon- treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached, β-alanine is then mixed with the base solution.
Example D221 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-15 treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-a-lysine are then mixed with the base solution.
Example D222 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is 20 reached. Glycine and poly-L-e-lysine are then mixed with the base solution.
Example D223 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Adipic acid is then mixed with the base solution. 25 Example D224 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is PCT/US2006/044574 WO 2007/061795 159 2015203721 02 Μ 2015 reached. Poly-L-a-lysine (molecular weight ~ 63,000) is then mixed with the base solution.
Example D225 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-5 treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 6,000) is then mixed with the base solution.
Example D226 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is 10 reached. Poly-L-a-lysine (molecular weight ~ 93,000) is then mixed with the base solution.
Example D227 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is 15 reached. Poly-L-a-lysine (molecular weight ~ 1,300,000) is then mixed with the base solution.
Example D228 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is 20 reached. Fruitaric acid is then mixed with the base solution.
Example D229 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Tartaric acid is then mixed with the base solution. 25 Example D230 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Sodium bisulfate is then mixed with the base solution. 2015203721 02M2015 WO 2007/061795 PCT/US2006/044574 160
Example D231 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Laurie arginate is then mixed with the base solution. 5 Example D232 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-lysine is then mixed with the base solution.
Example D233 10 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon- treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Guanidine hydrochloride is then mixed with the base solution.
Example D234 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-15 treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Urea and sodium chloride are then mixed with the base solution.
Example D235 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is 20 reached. Urea is then mixed with the base solution.
Example D236 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Choline chloride is then mixed with the base solution. 25 Example D237 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-glucosamine hydrochloride is then mixed with the base solution. 161 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574
Example D238 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-e-lysine is then mixed with the base solution. 5 Example D239 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine, sodium chloride and potassium chloride are then mixed with the base solution. 10 ExampleD240 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and aluminum sulfate (alum) are then mixed with the base solution.
Example D241 15 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon- treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and potassium chloride are then mixed with the base solution.
Example D242 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-20 treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and sodium gluconate are then mixed with the base solution.
Example D243 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is 25 reached. Polyethylenimine is then mixed with the base solution.
Example D244 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Chitosan is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 162 2015203721 02 Μ 2015
Example D245 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly L-omithine is then mixed with the base solution. 5 Example D246 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Magnesium chloride is then mixed with the base solution.
Example D247 10 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon- treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Whey protein (concentrate 34%) is then mixed with the base solution.
Example D248 400-500 mg of Luo Han Guo sweetener is dissolved in one liter carbon-15 treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Fumaric acid, malic acid and tartaric acid are then mixed with the base solution.
Example D249 25-50 ppm of monatin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia 20 seyal) is then mixed with the base solution.
Example D250 5% sucrose and 25-50 ppm monatin are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution. 25 Example D251 5% sucrose and 25-50 ppm of monatin are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. D-Tagatose is then mixed with the base solution. WO 2007/061795 2015203721 02 Μ 2015 PCT/U S2006/044574 163
Example D252 5% sucrose and 25-50 ppm of monatin are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution. 5 Example D253 3.3% sucrose and 25-50 ppm of monatin are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution.
Example D254 10 3.3% sucrose and 25-50 ppm of monatin are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution.
Example D255 25-50 ppm of monatin is dissolved in a citric acid/potassium citrate 15 composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D256 25-50 ppm of monatin is dissolved in a citric acid/potassium citrate 20 composition equivalent to that in a diet lemon-lime beverage. Glycine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D257 25-50 ppm of monatin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, fructose, 25 potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 164
Example D258 25-50 ppm of monatin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fructose, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. 5 Example D259 25-50 ppm of monatin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol and fibergum (e.g., gum acacia seyal) are then mixed with the base solution.
Example D260 10 25-50 ppm of monatin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution.
Example D261 25-50 ppm of monatin is dissolved in a citric acid/potassium citrate 15 composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D262 25-50 ppm of monatin is dissolved in a citric acid/potassium citrate 20 composition equivalent to that in a diet lemon-lime beverage. Glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D263 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic 25 acid is then mixed with the base solution.
Example D264 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid, potassium salt is then mixed with the base solution. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 165
Example D265 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-Threonine is then mixed with the base solution. 5 Example D266 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-Serine is then mixed with the base solution.
Example D267 10 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-alanine is then mixed with the base solution.
Example D268 25-50 mg of monatin is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine is then mixed with the base solution.
Example D269 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached, β-alanine is 20 then mixed with the base solution.
Example D270 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-a-lysine are then mixed with the base solution. 25 Example D271 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-e-lysine are then mixed with the base solution. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 166
Example D272 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Adipic acid is then mixed with the base solution. 5 Example D273 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 63,000) is then mixed with the base solution.
Example D274 10 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 6,000) is then mixed with the base solution.
Example D275 25-50 mg of monatin is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 83,000) is then mixed with the base solution.
Example D276 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-20 lysine (molecular weight ~ 1,300,000) is then mixed with the base solution.
Example D277 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Fruitaric acid is then mixed with the base solution. 25 Example D278 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Tartaric acid is then mixed with the base solution. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 167
Example D279 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Sodium bisulfate is then mixed with the base solution. 5 Example D280 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Laurie arginate is then mixed with the base solution.
Example D281 10 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-lysine is then mixed with the base solution.
Example D282 25-50 mg of monatin is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Guanidine hydrochloride is then mixed with the base solution.
Example D283 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Urea and 20 sodium chloride are then mixed with the base solution.
Example D284 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Urea is then mixed with the base solution. 25 Example D285 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Choline chloride is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 168 2015203721 02M2015
Example D286 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-glucosamine hydrochloride is then mixed with the base solution. 5 Example D287 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-ε-lysine is then mixed with the base solution.
Example D288 10 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine, sodium chloride and potassium chloride are then mixed with the base solution.
Example D289 25-50 mg of monatin is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and aluminum sulfate (alum) are then mixed with the base solution.
Example D290 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and 20 potassium chloride are then mixed with the base solution.
Example D291 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and sodium gluconate are then mixed with the base solution. 25 Example D292 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Polyethylenimine is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 169 2015203721 02 Μ 2015
Example D293 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Chitosan is then mixed with the base solution. 5 Example D294 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly L-omithine is then mixed with the base solution.
Example D295 10 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Magnesium chloride is then mixed with the base solution.
Example D296 25-50 mg of monatin is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Whey protein (concentrate 34%) is then mixed with the base solution.
Example D297 25-50 mg of monatin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Fumaric 20 acid, malic acid and tartaric acid are then mixed with the base solution.
Example D298 50-200 ppm of curculin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution. 25 Example D299 5% sucrose and 50-200 ppm curculin are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02M2015 170
Example D300 5% sucrose and 50-200 ppm of curculin are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. D-Tagatose is then mixed with the base solution. 5 Example D301 5% sucrose and 50-200 ppm of curculin are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution.
Example D302 10 3.3% sucrose and 50-200 ppm of curculin are dissolved in a citric acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol is then mixed with the base solution.
Example D303 3.3% sucrose and 50-200 ppm of curculin are dissolved in a citric 15 acid/potassium citrate composition equivalent to that in a lemon-lime beverage. Erythritol and D-tagatose are then mixed with the base solution.
Example D304 50-200 ppm of curculin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, 20 potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D305 50-200 ppm of curculin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Glycine, potassium chloride 25 and potassium dihydrogen phosphate are then mixed with the base solution.
Example D306 50-200 ppm of curculin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, fructose, 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 171 potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D307 50-200 ppm of curculin is dissolved in a citric acid/potassium citrate 5 composition equivalent to that in a diet lemon-lime beverage. Fructose, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D308 50-200 ppm of curculin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol and fibergum 10 (e.g., gum acacia seyal) are then mixed with the base solution.
Example D309 50-200 ppm of curculin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Fibergum (e.g., gum acacia seyal) is then mixed with the base solution. 15 Example D310 50-200 ppm of curculin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Erythritol, glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution. 20 Example D311 50-200 ppm of curculin is dissolved in a citric acid/potassium citrate composition equivalent to that in a diet lemon-lime beverage. Glycine, alanine, potassium chloride and potassium dihydrogen phosphate are then mixed with the base solution.
Example D312 25 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 172 2015203721 02 Jul2015
Example D313 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-Gluconic acid, potassium salt is then mixed with the base solution. 5 Example D314 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-Threonine is then mixed with the base solution.
Example D315 10 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-Serine is then mixed with the base solution.
Example D316 50-200 mg of curculin is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-alanine is then mixed with the base solution.
Example D317 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine is 20 then mixed with the base solution.
Example D318 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached, β-alanine is then mixed with the base solution. 25 Example D319 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-a-lysine are then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 173 2015203721 02 Jul2015
Example D320 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and poly-L-e-lysine are then mixed with the base solution. 5 Example D321 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Adipic acid is then mixed with the base solution.
Example D322 10 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight - 63,000) is then mixed with the base solution.
Example D323 50-200 mg of curculin is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 6,000) is then mixed with the base solution.
Example D324 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-20 lysine (molecular weight ~ 93,000) is then mixed with the base solution.
Example D325 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-a-lysine (molecular weight ~ 1,300,000) is then mixed with the base solution. 25 Example D326 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Fruitaric acid is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 174
Example D327 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Tartaric acid is then mixed with the base solution. 5 Example D328 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Sodium bisulfate is then mixed with the base solution.
Example D329 10 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Laurie arginate is then mixed with the base solution.
Example D330 50-200 mg of curculin is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. L-lysine is then mixed with the base solution.
Example D331 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Guanidine 20 hydrochloride is then mixed with the base solution.
Example D332 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Urea and sodium chloride are then mixed with the base solution. 25 Example D333 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Urea is then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 175
Example D334 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Choline chloride is then mixed with the base solution. 5 Example D335 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. D-glucosamine hydrochloride is then mixed with the base solution.
Example D336 10 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly-L-ε-lysine is then mixed with the base solution.
Example D337 50-200 mg of curculin is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine, sodium chloride and potassium chloride are then mixed with the base solution.
Example D338 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine 20 and aluminum sulfate (alum) are then mixed with the base solution.
Example D339 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and potassium chloride are then mixed with the base solution. 25 Example D340 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Glycine and sodium gluconate are then mixed with the base solution. PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 176
Example D341 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Polyethylenimine is then mixed with the base solution. 5 Example D342 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Chitosan is then mixed with the base solution.
Example D343 10 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Poly L-omithine is then mixed with the base solution.
Example D344 50-200 mg of curculin is dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Magnesium chloride is then mixed with the base solution.
Example D345 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Whey 20 protein (concentrate 34%) is then mixed with the base solution.
Example D346 50-200 mg of curculin is dissolved in one liter carbon-treated water and phosphoric acid (75%) is added until a pH between pH 2.4 and 2.5 is reached. Fumaric acid, malic acid and tartaric acid are then mixed with the base solution.
25 E. Example Set E
The formulations provided in Example Set E may be used in combination with other compounds found in orally ingestible compositions to form a total sum of 100% weight. The compounds which may be used in combination with the formulations provided may be in the form of a liquid, solid, gas, gel, or the like to act as a carrier for the PCT/U S2006/044574 WO 2007/061795 177 2015203721 02 Μ 2015 formulation. For example, water (e.g., carbonated, carbon-treated, or non-carbonated), flavors, and/or acidulant may be used to in addition to the provided formulations to give 100% weight total.
Example El 5 A composition comprising 3.5 % erythritol, 400 ppm of REBA, 0.02% flavor, and 0.5% tagatose are combined.
Example E2 A composition comprising 3.5 % erythritol, 400 ppm of REBA, 0.0015 flavor, and 0.5% tagatose are combined. 10 Example E3 A composition comprising 3.5 % erythritol, 400 ppm of REBA, 0.0033% flavor, and 0.5 % tagatose are combined.
Example E4 A composition comprising 3.4 % sucrose, 3.5 % erythritol, and 180 ppm of 15 REBA are combined.
Example E5 A composition comprising 5 % sucrose, 3.5 % erythritol, and 100 ppm of REBA are combined.
Example E6 20 A composition comprising 360 ppm of REBA, 0.75 % glycine, 250 ppm of KC1, and 650 ppm of KH2PO4 are combined.
Example E7 A composition comprising 3.5 % erythritol, 320 ppm of REBA, 0.75 % fructose, 250 ppm of KC1, and 650 ppm of KH2PO4 are combined. 25 Example E8 A composition comprising 3.5 % erythritol, 360 ppm of REBA, and 400 ppm of Fibergum P (acacia seyal) are combined. PCT/US2006/044574 WO 2007/061795 17Β 2015203721 02 Μ 2015
Example E9 A composition comprising 3.3% sucrose, 3.5 % erythritol, and 160 ppm of REBA are combined.
Example E10 5 A composition comprising 5 % sucrose, 3.5 % erythritol, and 90 ppm of REBA are combined.
Example Ell
A composition comprising 65 ppm of glutamic acid and 580 ppm of REBA are combined. 10 Example E12 A composition comprising 0.7 ppm of oleanolic acid, 3.5 % erythritol, 580 ppm of REBA, and flavorants are combined.
Example E13 A composition comprising 0.2% tagatose and 580 ppm of REBA are 15 combined.
Example E14 A composition comprising 0.2% tagatose, 0.6 ppm of flavorants, and 580 ppm of REBA are combined.
Example E15 20 A composition comprising 3.5% erythritol, and 580 ppm of REBA are combined.
Example E16 A composition comprising 0.005% flavorant and 580 ppm of REBA are combined. 25 Example E17 A composition comprising 20 ppm of talin and 580 ppm of REBA are combined. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 179
Example E18
A composition comprising 30 ppm of citrus extract and 580 ppm of REB A are combined.
Example E19
5 A composition comprising 0.1 to 0.05% flavorant and 580 ppm of REB A are combined.
Example E20 A composition comprising 0.033 Luo Han Guo sweetener and 580 ppm of REBA are combined. 10 Example E21 A composition comprising 3 ppm of flavorant and 580 ppm of REBA are combined.
Example E22 A composition comprising 0.004 ppm of bitter orange and 580 ppm of 15 REBA are combined.
Example E23
A composition comprising 0.004% of bitter orange and 580 ppm of REBA are combined.
Example E24 20 A composition comprising 2 ppm of heptadienal and 580 ppm of REBA are combined.
Example E25 A composition comprising 0.33% frutaric acid and 580 ppm of REBA are combined. 25 Example E26 A composition comprising 1,400 ppm of choline chloride and 580 ppm of REBA are combined. WO 2007/061795 PCT/US2006/044574 180
Example E27 A composition comprising 0.1% colloid and 580 ppm of REBA are combined.
Example E28 A composition comprising 0.033% flavorant and 580 ppm of REBA are combined.
Example E29 A composition comprising 0.15% of flavorant and 580 ppm of REBA are combined.
Example E30 A composition comprising 0.1% polyhydroxy alcohol and 580 ppm of REBA are combined.
Example E31 A composition comprising 3.5% erythritol, 65 ppm of succinic acid, and 3ppm of flavorant are combined with REBA.
F. Example Set F
Sweet taste improving compositions were combined with a REBA solution to determine their effect on sweetness linger. Screening of the initial sample, or further dilutions, allowed identification of concentrations which were just above-threshold, herein defined as “near-threshold concentrations.” The near-threshold additive concentrations, a 6- to 100-fold higher higher additive concentration (depending on the off-taste intensity), and a mid-level additive concentration (halfway between the near-threshold and higher additive concentration) were evaluated to determine the effect on sweetness linger of a REBA solution.
Formulations of a 500 ppm REBA in a phosphoric acid solution (75%) at a pH of 2.5 with phosphoric acid or a pH of 3.1 with citric acid and potassium citrate were prepared prior to the addition of the additives at the three levels of concentration.
Sensory evaluation using the protocol described in Example Set G then was used to evaluate the sweetness linger of the REBA solutions. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 181
Control Samples 500 ppm of REBA was dissolved in one liter of carbon-treated water and phosphoric acid (75%) was added until a pH between 2.4 and 2.5 was reached. The sweetness linger rating of this control sample was determined to be 5. 5 10 g of sugar was dissolved in 100 ml of carbon treated water and phosphoric acid (75%) was added until a pH between 2.4 and 2.5 was reached. The sweetness linger rating of this control sample was determined to be 0.
The following Examples F 1-148 illustrate combinations of rebaudioside A and sweet taste improving compositions in accordance with particular embodiments of this 10 invention:
Example FI 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5,000 ppm of D-fructose was then mixed with the base solution. The sweetness linger of this 15 solution was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example F2 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 2,500 20 ppm to 20,000 ppm of propylene glycol was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F3 360 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 35,000 25 ppm of erythritol was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F4 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 93 WO 2007/061795 2015203721 02 Μ 2015 PCT/US2006/044574 182 ppm to 368 ppm of NaCl was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F5 500 ppm of REBA was dissolved in one liter carbon-treated water and 5 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 25,000 ppm to 50,000 ppm of NaCl was then mixed with the base solution. The sweetness linger of this solution was determined to be 1.
Example F6 500 ppm of REBA was dissolved in one liter carbon-treated water and 10 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,192 ppm to 4,770 ppm of KC1 was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example F7 15 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 10 ppm to 500 ppm of NaHSC>4.H20 was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F8 20 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 10,000 ppm to 50,000 ppm of NaH2P04.H20 was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example F9 25 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 10,000 ppm to 20,000 ppm of KH2PO4 was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. PCT/US2006/044574 WO 2007/061795 183 2015203721 02 Jul2015
Example F10 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5,000 ppm of MgSC>4 was then mixed with the base solution. The sweetness linger of this 5 solution was determined to be 3.
Example Fll 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 404 ppm to 1,003 ppm of KA1(SC>4)2 (alum) was then mixed with the base solution. The 10 sweetness linger of this solution was determined to be 3.
Example F12 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 250 ppm of KA1(SC>4)2 (alum) was then mixed with the base solution. The sweetness linger 15 of this solution was determined to be 4.
Example F13 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 24 ppm to 700 ppm of zinc chloride was then mixed with the base solution. The sweetness 20 linger of this solution was determined to be 3.
Example F14 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 450 ppm of KC1 and 680 ppm of KH2PO4 were then mixed with the base solution. The 25 sweetness linger of this solution was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example F15 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 470 WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 184 ppm of choline chloride was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F16 500 ppm of REBA was dissolved in one liter carbon-treated water and 5 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,175 ppm to 1,400 ppm of choline chloride was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.5.
Example F17 500 ppm of REBA was dissolved in one liter carbon-treated water and 10 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 50 ppm to 1,000 ppm of D-gluconic acid, Na Salt was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F18 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 50 ppm to 1,000 ppm of D-gluconic acid, K Salt was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F19 500 ppm of REBA was dissolved in one liter carbon-treated water and 20 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 10 ppm to 33 ppm of Guanidine HC1 was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F20 500 ppm of REBA was dissolved in one liter carbon-treated water and 25 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 500 ppm to 2,000 ppm of potassium benzoate was then mixed with the base solution. The sweetness linger of this solution was determined to be 4. 2015203721 02M2015 WO 2007/061795 PCT/US2006/044574 185
Example F21 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3,500 ppm to 7,000 ppm of D-Glucosamine HC1 was then mixed with the base solution. The 5 sweetness linger of this solution was determined to be 4.
Example F22 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 647 ppm of fumaric acid was then mixed with the base solution. The sweetness linger of this 10 solution was determined to be 3.
Example F23 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 887 ppm of malic acid was then mixed with the base solution. The sweetness linger of this 15 solution was determined to be 4.
Example F24 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 150 ppm to 200 ppm of malic acid was then mixed with the base solution. The sweetness 20 linger of this solution was determined to be 3.
Example F25 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 2,500 ppm of malic acid was then mixed with the base solution. The sweetness linger of this 25 solution was determined to be 2.
Example F26 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 813 PCT/US2006/044574 WO 2007/061795 186 2015203721 02 Μ 2015 ppm of tartaric acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F27 500. ppm of REBA was dissolved in one liter carbon-treated water and 5 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 50 ppm to 200 ppm of citric acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F28 500 ppm of REBA was dissolved in one liter carbon-treated water and 10 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,171 ppm of citric acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F29 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,500 ppm of citric acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example F30 500 ppm of REBA was dissolved in one liter carbon-treated water and 20 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 50 ppm to 1,400 ppm of adipic acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example F31 25 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,400 ppm of adipic acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. This formulation was found to have sugar-like tastecharacteristics. WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 187
Example F32 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 2,553 ppm of ascorbic acid was then mixed with the base solution. The sweetness linger of this 5 solution was determined to be 4.
Example F33 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 200 ppm to 400 ppm of tannic acid was then mixed with the base solution. The sweetness 10 linger of this solution was determined to be 3.
Example F34 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 15,000 ppm of glycine was then mixed with the base solution. The sweetness linger of this 15 solution was determined to be 1. This formulation was found to have sugar-like taste characteristics.
Example F35 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3,750 20 ppm of glycine was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.5. This formulation was found to have sugar-like taste characteristics.
Example F36 500 ppm of REBA was dissolved in one liter carbon-treated water and 25 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 7,000 ppm of glycine was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. This formulation was found to have sugar-like taste characteristics. WO 2007/061795 2015203721 02 Jul 2015 PCT/US2006/044574 188
Example F37 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5,000 ppm of L-alanine was then mixed with the base solution. The sweetness linger of this 5 solution was determined to be 2. This formulation was found to have sugar-like taste characteristics.
Example F38 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 2,500 10 ppm, and 7,000 ppm tol0,000 ppm of L-alanine were then dissolved in their respective base solutions. The sweetness linger of both solutions was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example F39 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5,000 ppm to 25,000 ppm of L-Serine was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F40 500 ppm of REBA was dissolved in one liter carbon-treated water and 20 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 150 ppm to 15,000 ppm of L-threonine was then mixed in their respective base solutions. The sweetness linger of these solutions were determined to be 4.
Example F41 500 ppm of REBA was dissolved in one liter carbon-treated water and 25 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 2,500 ppm and 10,000 ppm of β-alanine were then mixed with the base solution. The sweetness linger of this solution was determined to be 2. The combination was found to have sugarlike characteristics. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 189
Example F42 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5,000 ppm of β-alanine was then mixed with the base solution. The sweetness linger of this 5 solution was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example F43 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 100 10 ppm to 10,000 ppm of γ-amino butyric acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F44 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 10 15 ppm to 100 ppm of γ-amino butyric acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F45 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 100 20 ppm of L-aspartic acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F46 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,000 25 ppm of L-aspartic acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F47 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 4,000 PCT/US2006/044574 WO 2007/061795 190 2015203721 02 Jul2015 ppm of L-glutamic acid, Na salt was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F48 500 ppm of REBA was dissolved in one liter carbon-treated water and 5 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 150 ppm to 750 ppm of L-lysine was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F49 500 ppm of REBA was dissolved in one liter carbon-treated water and 10 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,500 ppm of L-lysine was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F50 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5,000 ppm of glycine and 2,500 ppm of L-alanine were then mixed with the base solution. The sweetness linger of this solution was determined to be 2. This formulation was found to have sugar-like taste characteristics.
Example F51 20 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3,750 ppm of glycine and 3,750 ppm of L-alanine were then mixed with the base solution. The sweetness linger of this solution was determined to be 2. This formulation was found to have sugar-like taste characteristics. 25 Example F52 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 150 ppm of dioctyl sulfosuccinate sodium was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 191
Example F53 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 10 ppm to 40 ppm of cetylpyridinium chloride was then mixed with the base solution. The 5 sweetness linger of this solution was determined to be 4.
Example F54 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached 0.4 ppm to 10 ppm of cetylpyridinium chloride was then mixed with the base solution. The 10 sweetness linger of this solution was determined to be 4.5.
Example F55 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 20 ppm to 63 ppm of hexadecyltrimethylammonium bromide was then mixed with the base 15 solution. The sweetness linger of this solution was determined to be 4.
Example F56 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 2,500 ppm of sucrose oleate was then mixed with the base solution. The sweetness linger of this 20 solution was determined to be 2.
Example F57 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 400 ppm of sucrose oleate was then mixed with the base solution. The sweetness linger of this 25 solution was determined to be 3.
Example F58 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 20 WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 192 ppm to 5,000 ppm of sucrose stearate was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F59 500 ppm of REBA was dissolved in one liter carbon-treated water and 5 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 300 ppm of Polysorbate 20 was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F60 500 ppm of REBA was dissolved in one liter carbon-treated water and 10 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 600 ppm of Polysorbate 80 was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F61 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 500 ppm of lecithin (HLB value: 9.0) was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F62 500 ppm of REBA was dissolved in one liter carbon-treated water and 20 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5 ppm to 50 ppm of polyethyleneimine (50% in water) was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F63 500 ppm of REBA was dissolved in one liter carbon-treated water and 25 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 80 ppm to 200 ppm of poly-L-omithine was then mixed with the base solution. The sweetness linger of this solution was determined to be 4. PCT/US2006/044574 WO 2007/061795 193 2015203721 02 Μ 2015
Example F64 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 400 ppm of poly-L-omithine was then mixed with the base solution. The sweetness linger of 5 this solution was determined to be 3.
Example F65 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 200 ppm of poly-L-a-lysine, MW 1,300,000 was then mixed with the base solution. The 10 sweetness linger of this solution was determined to be 3.
Example F66 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 400 ppm of poly-L-a-lysine, MW 1,300,000 was then mixed with the base solution. The 15 sweetness linger of this solution was determined to be 2.
Example F67 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 200 ppm of poly-L-a-lysine, MW 1,500 was then mixed with the base solution. The sweetness 20 linger of this solution was determined to be 3.
Example F68 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 400 ppm of poly-L-a-lysine, MW 1,500 was then mixed with the base solution. The sweetness 25 linger of this solution was determined to be 2.
Example F69 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 40 WO 2007/061795 2015203721 02M2015 PCT/IIS2006/044574 194 ppm to 200 ppm of poly-L-a-lysine, MW 25,200 was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F70 500 ppm of REBA was dissolved in one liter carbon-treated water and 5 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 200 ppm of poly-L-a-lysine, MW 6,000 was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F71 500 ppm of REBA was dissolved in one liter carbon-treated water and 10 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 400 ppm of poly-L-a-lysine, MW 6,000 was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example F72 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 200 ppm of poly-L-a-lysine, MW 63,000 was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F73 500 ppm of REBA was dissolved in one liter carbon-treated water and 20 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 400 ppm of poly-L-a-lysine, MW 63,000 was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example F74 500 ppm of REBA was dissolved in one liter carbon-treated water and 25 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 300 ppm of poly-L-a-lysine, MW 83000 was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. WO 2007/061795 2015203721 02M2015 PCT/US2006/044574 195
Example F75 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 40 ppm of poly-L-a-lysine, MW 83,000 was then mixed with the base solution. The 5 sweetness linger of this solution was determined to be 4.
Example F76 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 10 ppm to 1,000 ppm of poly-L-s-lysine was then mixed with the base solution. The 10 sweetness linger of this solution was determined to be 2.
Example F77 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 502 ppm of poly-L-s-lysine (25% solution) was then mixed with the base solution. The 15 sweetness linger of this solution was determined to be 2.
Example F78 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 50 ppm of poly-L-s-lysine (25% solution) was then mixed with the base solution. The 20 sweetness linger of this solution was determined to be 4.
Example F79 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 10 ppm to 1,000 ppm of chitosan was then mixed with the base solution. The sweetness 25 linger of this solution was determined to be 3.
Example F80 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,000 WO 2007/061795 PCT/US200(i/044574 196 2015203721 02 Jul 2015 ppm of bovine serum albumin (BSA) was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F81 500 ppm of REBA was dissolved in one liter carbon-treated water and 5 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 200 ppm to 5,000 ppm of whey protein (concentrate 34%) was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F82 500 ppm of REBA was dissolved in one liter carbon-treated water and 10 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 200 ppm to 5,000 ppm of whey protein hydrolysate, 90% was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F83 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 7,500 ppm of L-alanyl-L-glutamine was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. This formulation was found to have sugarlike taste characteristics.
Example F84 20 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 15,000 ppm of glycine and 375 ppm of KA1(S04)2.12H20 (Alum) were then mixed with the base solution. The sweetness linger of this solution was determined to be 2. This formulation was found to have sugar-like taste characteristics. 25 Example F85 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5,000 ppm of urea and 584 ppm of sodium chloride were then mixed with the base solution. The sweetness linger of this solution was determined to be 4. 197 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574
Example F86 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,500 ppm of urea and 584 ppm of sodium chloride were then mixed with the base solution. The 5 sweetness linger of this solution was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example F87 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3,750 10 ppm of glycine and 60 ppm to 90 ppm of poly-L-a-lysine were then mixed with the base solution. The sweetness linger of this solution was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example F88 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3,750 ppm of glycine and 10 ppm of poly-L-s-lysine were then mixed with the base solution. The sweetness linger of this solution was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example F89 20 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3,750 ppm of glycine and 119 ppm of potassium chloride were then mixed with the base solution. The sweetness linger of this solution was determined to be 4. This formulation was found to have sugar-like taste characteristics. 25 Example F90 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 15,000 ppm of glycine and 239 ppm of potassium chloride were then mixed with the base solution. The sweetness linger of this solution was determined to be 2. This formulation 30 was found to have sugar-like taste characteristics. 198 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574
Example F91 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3,750 ppm of glycine and 238 ppm of sodium chloride were then mixed with the base solution. 5 The sweetness linger of this solution was determined to be 4. This formulation was found to have sugar-like taste characteristics.
Example F92 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3,750 10 ppm of glycine, 43 ppm of NaCl and 51 ppm of KC1 were then mixed with the base solution. The sweetness linger of this solution was determined to be 4. This formulation was found to have sugar-like taste characteristics.
Example F93 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 15,000 ppm of glycine and 501 ppm of sodium gluconate were then mixed with the base solution. The sweetness linger of this solution was determined to be 2. This formulation was found to have sugar-like taste characteristics.
Example F94 20 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,000 ppm of lauric arginate was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F95 25 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 2,500 ppm of L-alanine and 5,000 ppm of fructose were then mixed with the base solution. The sweetness linger of this solution was determined to be 4. This formulation was found to have sugar-like taste characteristics. 30 PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 199
Example F96 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 164 ppm to 540 ppm of ffuitaric acid was then mixed with the base solution. The sweetness 5 linger of this solution was determined to be 4.
Example F97 360 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3,750 ppm glycine and 35,000 ppm of erythritol were then mixed with the base solution. The 10 sweetness linger of this solution was determined to be 2. This formulation was found to have sugar-like taste characteristics.
Example F98 360 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 35,000 15 ppm of erythritol, 3,750 ppm of glycine, 450 ppm of KC1, 680 ppm of KH2PO4, and 1,175 ppm of choline chloride were then mixed with the base solution. The sweetness linger of this solution was determined to be 1. This formulation was found to have sugar-like taste characteristics.
Example F99 20 360 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 2,500 ppm of L-alanine, 5,000 ppm of fructose, and 35,000 ppm of erythritol were then mixed with the base solution. The sweetness linger of this solution was determined to be 4. This formulation was found to have sugar-like taste characteristics. 25 Example F100 360 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 35,000 ppm of erythritol, 3,750 ppm of glycine, 450 ppm of KC1, and 680 ppm of KH2PO4 were then mixed with the base solution. The sweetness linger of this solution was determined 30 to be 4. This formulation was found to have sugar-like taste characteristics. PCT/US2006/044574 WO 2007/061795 2015203721 02M2015 200
Example F101 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 625 ppm to 10,000 ppm of D-tagatose was then mixed with the base solution. The sweetness 5 linger of this solution was determined to be 2.
Example F102 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 625 ppm to 20,000 ppm of trehalose was then mixed with the base solution. The sweetness 10 linger of this solution was determined to be 2.
Example F103 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,250 ppm to 20,000 ppm of Fructooligosaccharide was then mixed with the base solution. The 15 sweetness linger of this solution was determined to be 2.
Example F104 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 25 ppm to 800 ppm of gum acacia Senegal was then mixed with the base solution. The 20 sweetness linger of this solution was determined to be 2.
Example F105 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 1,000 ppm of Fructooligosaccharide (55%) was then mixed with the base solution. The 25 sweetness linger of this solution was determined to be 3. This formulation was found to have sugar-like taste characteristics.
Example F106 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 625 WO 2007/061795 2015203721 02 Μ 2015 PCT /US2006/044574 201 ppm to 10,000 ppm of ethanol was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example F107 500 ppm of REBA was dissolved in one liter carbon-treated water and 5 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 312 ppm to 10,000 ppm of propylene glycol was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F108 500 ppm of REBA was dissolved in one liter carbon-treated water and 10 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 312 ppm to 10,000 ppm of β-cyclodextrin was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F109 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 37 ppm to 600 ppm of NaCl was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F110 500 ppm of REBA was dissolved in one liter carbon-treated water and 20 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 37 ppm to 600 ppm of KC1 was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example Fill 500 ppm of REBA was dissolved in one liter carbon-treated water and 25 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 37 ppm to 600 ppm of KH2PO4 was then mixed with the base solution. The sweetness linger of this solution was determined to be 3. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 202
Example F112 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 16 ppm to 206 ppm of MSG was then mixed with the base solution. The sweetness linger of 5 this solution was determined to be 4.
Example F113 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 12 ppm to 400 ppm of AMP was then mixed with the base solution. The sweetness linger of 10 this solution was determined to be 3.
Example F114 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 125 ppm to 4,000 ppm of sodium gluconate was then mixed with the base solution. The 15 sweetness linger of this solution was determined to be 4.
Example F115 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 31 ppm to 1,000 ppm of potassium tartrate was then mixed with the base solution. The 20 sweetness linger of this solution was determined to be 3.
Example F116 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 31 ppm to 1,000 ppm of sodium tartrate was then mixed with the base solution. The 25 sweetness linger of this solution was determined to be 3.
Example F117 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 200 WO 2007/061795 2015203721 02M2015 PCT/US2006/044574 203 ppm to 1,000 ppm of malic acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F118 500 ppm of REBA was dissolved in one liter carbon-treated water and 5 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 31 ppm to 500 ppm of 2,4-dihydroxybenzoic acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example F119 500 ppm of REBA was dissolved in one liter carbon-treated water and 10 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 28 ppm to 900 ppm of caffeic acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F120 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 25 ppm to 400 ppm of chlorogenic acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F121 500 ppm of REBA was dissolved in one liter carbon-treated water and 20 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 25 ppm to 400 ppm of D/L-alanine was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F122 500 ppm of REBA was dissolved in one liter carbon-treated water and 25 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 25 ppm to 800 ppm of threonine was then mixed with the base solution. The sweetness linger of this solution was determined to be 2. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 204
Example F123 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 312 ppm to 10,000 ppm of taurine was then mixed with the base solution. The sweetness 5 linger of this solution was determined to be 3.
Example F124 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 312 ppm to 10,000 ppm of glycine was then mixed with the base solution. The sweetness 10 linger of this solution was determined to be 2.
Example F125 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3 ppm to 100 ppm of naringin was then mixed with the base solution. The sweetness linger of 15 this solution was determined to be 3.
Example F126 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 0.3 ppm to 10 ppm of quinine was then mixed with the base solution. The sweetness linger of 20 this solution was determined to be 3.
Example F127 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 0.3 ppm to 10 ppm of viridiflorol was then mixed with the base solution. The sweetness 25 linger of this solution was determined to be 3.
Example F128 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 31 WO 2007/061795 2015203721 02 Jul2015 PCT/US2006/044574 205 ppm to 1,000 ppm of Polyphenon 60 was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F129 500 ppm of REBA was dissolved in one liter carbon-treated water and 5 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 31 ppm to 1,000 ppm of hydroxycitric acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F130 500 ppm of REBA was dissolved in one liter carbon-treated water and 10 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 300 ppm to 10,000 ppm of glucosamine HC1 was then mixed with the base solution. The sweetness linger of this solution was determined to be 4.
Example F131 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 31 ppm to 1,000 ppm of Salicylic acid was then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F132 500 ppm of REBA was dissolved in one liter carbon-treated water and 20 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5% sucrose, 3.5% erythritol, and 0.75% D-tagatose were then mixed with the base solution. The sweetness linger of this solution was determined to be 0.
Example F133 500 ppm of REBA was dissolved in one liter carbon-treated water and 25 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5% sucrose and 0.75% D-tagatose were then mixed with the base solution. The sweetness linger of this solution was determined to be 2. PCT/US2006/044574 WO 2007/061795 2015203721 02 Jul2015 206
Example F134 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3.3% sucrose, 3.5% erythritol, and 0.75% D-tagatose were then mixed with the base solution. 5 The sweetness linger of this solution was determined to be 1.
Example F135 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3.3% sucrose and 3.5% D-tagatose were then mixed with the base solution. The sweetness 10 linger of this solution was determined to be 2.
Example F136 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5% sucrose and 3.5% erythritol were then mixed with the base solution. The sweetness linger 15 of this solution was determined to be 0.
Example F137 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 5% of sucrose was then mixed with the base solution. The sweetness linger of this solution was 20 determined to be 2.
Example F138 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3.3% sucrose and 3.5% erythritol were then mixed with the base solution. The sweetness linger 25 of this solution was determined to be 1.
Example F139 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3.30% WO 2007/061795 2015203721 02 Μ 2015 PCT/US2006/044574 207 of sucrose was then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example F140 500. ppm of REBA was dissolved in one liter carbon-treated water and 5 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3.5% erythritol, 0.75% glycine, 250 ppm of KC1, 650 ppm of KH2P04 were then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example F141 500 ppm of REBA was dissolved in one liter carbon-treated water and 10 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 0.75% glycine, 250 ppm of KC1, 650 ppm of KH2PO4 were then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example F142 500 ppm of REBA was dissolved in one liter carbon-treated water and 15 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3.5% erythritol, 0.75% fructose, 250 ppm of KC1, 650 ppm of KH2PO4 were then mixed with the base solution. The sweetness linger of this solution was determined to be 2.
Example F143 500 ppm of REBA was dissolved in one liter carbon-treated water and 20 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 0.75% fructose, 250 ppm of KC1, and 650 ppm of KH2PO4 were then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
Example F144 500 ppm of REBA was dissolved in one liter carbon-treated water and 25 phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3.5% erythritol and 400 ppm of gum acacia Senegal were then mixed with the base solution. The sweetness linger of this solution was determined to be 2. 2015203721 02 Μ 2015 WO 2007/061795 PCT/US2006/044574 208
Example F145 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 400 ppm of gum acacia Senegal was then mixed with the base solution. The sweetness linger 5 of this solution was determined to be 3.
Example F146 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 3.5% erythritol, 0.5% glycine, 250 ppm of KC1, 650 ppm of KH2PO4, and 0.25% of D-alanine 10 were then mixed with the base solution. The sweetness linger of this solution was determined to be 1.
Example F147 500 ppm of REBA was dissolved in one liter carbon-treated water and phosphoric acid (75%) was added until a pH between pH 2.4 and 2.5 was reached. 0.5% 15 glycine, 250 ppm of KC1 650, ppm of KH2PO4, and 0.25% of D-alanine were then mixed with the base solution. The sweetness linger of this solution was determined to be 3.
The following Examples G1-G3, H1-H3,1, J1-J3, and K illustrate methods of making purified rebaudioside A in accordance with particular embodiments of this invention:
20 G. Example Set G
Table 3: Summary of Examples Gl-3
Crude Rebaudioside A (ε) Ethanol (95%)(mL) Solvent Methanol (99%)(mL) Water (mL) Heating TOC) Drying TOC) Yield (g) HPLC Purity (wt/wt %) G1 400 1200 400 320 50 50 130 98.9 G2 100 320 120 50 30-40 60 72 98.3 G3 50 160 60 25 ~ 30 60 27.3 98.2
Example G1
Crude rebaudioside A (77.4% purity) mixture was obtained from a 25 commercial source. The impurities (6.2% stevioside, 5.6% rebaudioside C, 0.6 % rebaudioside F, 1.0 % other steviolglycosides 2, 3.0% rebaudioside D, 4.9% rebaudioside 2015203721 02 Μ 2015 WO 2007/061795 PCT/IJS2006/044574 209 Β, 0.3% steviolbioside) were identified and quantified using HPLC on dry basis, moisture content 4.7%.
Crude rebaudioside A (400 g), ethanol (95%, 1200 mL), methanol (99%, 400 mL) and water (320 mL) were combined and heated to 50°C for 10 minutes. The 5 clear solution was cooled to 22°C for 16 hours. The white crystals were filtered and washed twice with ethanol (2 x 200 mL, 95%) and dried in a vacuum oven at 50°C for 16-24 hours under reduced pressure (20 mm).
The final composition of substantially pure rebaudioside A (130 g) comprised 98.91% rebaudioside A, 0.06% stevioside, 0.03% rebaudioside C, 0.12% 10 rebaudioside F, 0.13% other steviolglycosides, 0.1% rebaudioside D, 0.49% rebaudioside B and 0.03% steviolbioside, all by weight.
Example G2
Crude rebaudioside A (80.37 %) was obtained from a commercial source. The impurities (6.22% stevioside, 2.28% rebaudioside C, 0.35% Dulcoside, 0.78 % 15 rebaudioside F, 0.72 % other steviolglycosides, 3.33% rebaudioside B, 0.07% steviolbioside) were identified by HPLC on dry basis, moisture content 3.4%.
Crude rebaudioside A (100 g), ethanol (95%, 320 mL), methanol (99%, 120 mL) and water (50 mL) were combined and heated to 30-40°C for 10 minutes. The clear solution was cooled to 22°C for 16 hours. The white crystals were filtered and washed 20 twice with ethanol (2 x 50 mL, 95%). The wet filter cake (88 g) was slurried in ethanol (95%, 1320 mL) for 16 hours, filtered, washed with ethanol (95%, 2 x 100 mL) and dried in a vacuum oven at 60°C for 16-24 hours under reduced pressure (20 mm).
The final composition of substantially pure rebaudioside A (72 g) comprised 98.29% rebaudioside A, 0.03% stevioside, 0.02% rebaudioside C, 0.17% rebaudioside F, 25 0.06% rebaudioside D and 1.09% rebaudioside B. Steviolbioside was not detected by HPLC.
Example G3
Crude rebaudioside A (80.37%) was obtained from a commercial source. The impurities (6.22% stevioside, 2.28% rebaudioside C, 0.35% Dulcoside, 0.78 % PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 210 rebaudioside F, 0.72 % other steviolglycosides, 3.33% rebaudioside B, 0.07% steviolbioside) were identified by HPLC on dry basis, moisture content 3.4%.
Crude rebaudioside A (50 g), ethanol (95%, 160 mL), methanol (99%, 60 mL) and water (25 mL) were combined and heated to approximately 30°C for 10 minutes. 5 The clear solution was cooled to 22°C for 16 hours. The white crystals were filtered and washed twice with ethanol (2 x 25 mL, 95% ). The wet filter cake (40 g) was slurried in methanol (99%, 600 mL) for 16 hours, filtered, washed with methanol (99%, 2 x 25 mL) and dried in a vacuum oven at 60°C for 16-24 hours under reduced pressure (20 mm).
The final composition of substantially pure rebaudioside A (27.3g) 10 comprised 98.22% rebaudioside A, 0.04% stevioside, 0.04% rebaudioside C, 0.18% rebaudioside F, 0.08% rebaudioside D and 1.03% rebaudioside B. Steviolbioside was not detected by HPLC.
H. Example Set H
Table 4: Summary of Examples H1-H3 1 Solvent I 1 Crude Rebaudioside A(g) Ethanol (95%)(mL) Organic Co-solvent (mL) Water (mL) Wash Solvent Yield (g) HPLC Purity (%) HI 5 15 Methanol (6) 3.5 EtOH/MeOH (3:1 v/v) 2.6 >99 H2 5 15 Methanol (5) 4 EtOH/MeOH (3:1 v/v) 2.3 >99 H3 5 16 Methanol (6) 2.5 *EtOH/MeOH (8:3 v/v) 3.2 >98
15 Example HI A mixture of crude rebaudioside A (80.37 % purity, 5 g), ethanol (95%, 15 mL), methanol (5 mL) and water (3.5 mL) were combined and heated to reflux for 10 minutes. The clear solution was cooled to 22°C for 16 hours while stirring. The white crystalline product was filtered, washed twice with ethanokmethanol (5.0 mL, 3:1, v/v) 20 mixture and dried in a vacuum oven at 50°C for 16-24 hours under reduced pressure (20 mm) to yield 2.6 g of purified product (>99% by HPLC).
Example 112 A mixture of crude rebaudioside A (80.37 % purity, 5 g), ethanol (95%, 15 mL), methanol (5 mL) and water (4.0 mL) were combined and heated to reflux for 10 25 minutes. The clear solution was cooled to 22°C for 16 hours while stirring. The white PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 211 crystalline product was filtered, washed twice with ethanohmethanol (5.0 mL, 3:1, v/v) mixture and dried in a vacuum oven at 50°C for 16-24 hours under reduced pressure (20 mm) to yield 2.3 g of purified product (>99% by HPLC).
Example H3 5 A mixture of crude rebaudioside A (80.37 % purity, 5 g), ethanol (95%, 16 mL), methanol (6 mL) and water (2.5 mL) were combined and heated to reflux for 10 minutes. The clear solution was cooled to 22°C for 2 hours. During this time, crystals started to appear. The mixture is stirred at room temperature for 16 hours. The white crystalline product was filtered, washed twice with ethanohmethanol (5.0 mL, 8:3, v/v) 10 mixture and dried in a vacuum oven at 50°C for 16-24 hours under reduced pressure (20 mm) to yield 3.2 g of purified product (>98% by HPLC).
1. Example Set I
Table 5: Summary of Example I
Solvent Crude Rebaudioside A (g) Organic Solvent (mL) Water (mL) Wash Solvent Yield (g) HPLC Purity (%) I 50 EtOH (160) 40 EtOH 19.8 99.5 15 A mixture of crude rebaudioside A (80.37 % purity, 50 g), ethanol (95%, 160 mL) and water (40 mL) were combined and heated to reflux for 30 minutes. The mixture was then allowed to cool to ambient temperature for 16-24 hours. The white crystalline product was filtered, washed twice with ethanol (95%, 25 mL), and dried in a vacuum oven at 60°C for 16-24 hours under reduced pressure (20 mm) to yield 19.8 g of 20 purified product (99.5% by HPLC).
J. Example Set J
Table 6: Summary of Examples J1-J3
Crude Rebaudioside A(g) Ethanol (95%)(mL) Organic Co-solvent (mL) Water (mL) Methanol Slurry (mL) Yield (g) HPLC Purity (%) J1 50 160 Methanol (60) 25 200 12.7 >97 J2 50 160 Methanol (60) 25 300 18.6 >97 J3 50 160 Methanol (60) 25 350 22.2 >97 PCT/US2006/044574 WO 2007/061795 2015203721 02 Μ 2015 212
Example J1 A mixture of crude rebaudioside A (41% purity, 50 g), ethanol (95%, 160 mL), methanol (99.8 %, 60 mL) and water (25 mL) were combined by stirring at 22°C. A white product crystallized out in 5-20 hours. The mixture was stirred for additional 48 5 hours. The white crystalline product was filtered and washed twice with ethanol (95%, 25 mL). The wet cake of white crystalline product then was slurried in methanol (99.8 %, 200 mL) for 16 hours, filtered, washed twice with methanol (99.8 %, 25 mL), and dried in a vacuum oven at 60°C for 16-24 hours under reduced pressure (20 mm) to yield 12.7 g of purified product (>97% by HPLC). 10 Example J2 A mixture of crude rebaudioside A (48% purity, 50 g), ethanol (95%, 160 mL), methanol (99.8 %, 60 mL) and water (25 mL) was combined by stirring at 22°C. The white product crystallized out in 3-6 hours. The mixture was stirred for additional 48 hours. The white crystalline product was filtered and washed twice with ethanol (95%, 25 15 mL). The wet cake of white crystalline product then was slurried in methanol (99.8 %, 300 mL) for 16 hours, filtered, washed twice with methanol (99.8 %, 25 mL) and dried in a vacuum oven at 60°C for 16-24 hours under reduced pressure (20 mm) to yield 18.6 g of purified product (>97% by HPLC).
Example J3 20 A mixture of crude rebaudioside A (55% purity, 50 g), ethanol (95%, 160 mL), methanol (99.8 %, 60 mL) and water (25 mL) was combined by stirring at 22°C. The white product crystallized out in 15-30 minutes. The mixture was stirred for an additional 48 hours. The white crystalline product was filtered and washed twice with ethanol (95%, 25 mL). The wet cake of white crystalline product was slurried in methanol (99.8 %, 350 25 mL) for 16 hours, filtered, washed twice with methanol (99.8 %, 25 mL) and dried in a vacuum oven at 60°C for 16-24 hours under reduced pressure (20 mm) to yield 22.2 g of purified product (>97 % by HPLC).
K. Example K A solution of rebaudioside A ( >97% pure by HPLC ) was prepared in 30 double distilled water (12.5 gm in 50 mL, 25 % concentration) by stirring the mixture at WO 2007/061795 2015203721 02 Μ 2015 PCT/US2006/044574 213 40°C for 5 minutes. An amorphous rebaudioside A polymorph was formed by immediately using the clear solution for spray drying with the Lab-Plant spray drier SD-04 instrument (Lab-Plant Ltd., West Yorkshire, U.K.). The solution was fed through the feed pump into the nozzle atomizer which atomized it into a spray of droplets with the help of a 5 constant flow of nitrogen / air. Moisture was evaporated from the droplets under controlled temperature conditions (about 90 to about 97°C) and airflow conditions in the drying chamber and resulted in the formation of dry particles. This dry powder (11-12 g) was discharged continuously from the drying chamber and was collected in a bottle. The solubility in water at room temperature was determined to be > 35.0 %. 10 While the invention has been described in detail with respect to specific embodiments thereof, it will be appreciated that those skilled in the art, upon attaining an understanding of the foregoing, may readily conceive of alterations to, variations of, and equivalents to these embodiments. Accordingly, the scope of the present invention should be assessed as that of the appended claims and any equivalents thereof. 15

Claims (13)

  1. The claims defining the invention are as follows:
    1. A sweetener composition comprising rebaudioside A and psicose, wherein the rebaudioside A has a purity greater than about 80% by weight on a dry basis and the psicose is in the D-configuration.
  2. 2. The sweetener composition of claim 1, wherein the rebaudioside A has a purity greater than about 95% by weight on a dry basis.
  3. 3. The sweetener composition of claim 1 or 2, further comprising at least one sweet taste improving polyol additive selected from the group consisting of erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, inositol, isomalt, propylene glycol, glycerol, threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup and reduced glucose syrup.
  4. 4. The sweetener composition of claim 3, wherein the at least one sweet taste improving polyol additive is erythritol.
  5. 5. The sweetener composition of any one of claims 1 to 4, further comprising at least one sweet taste improving amino acid additive or salt thereof, wherein the amino acid additive is selected from the group consisting of aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid, glutamine, hydroxyproline, taurine, norvaline and sarcosine.
  6. 6. The sweetener composition of any one of claims 1 to 5, further comprising at least one sweet taste improving inorganic salt additive selected from the group consisting of sodium chloride, potassium chloride, sodium sulfate, potassium citrate, europium chloride, gadolinium chloride, terbium chloride, magnesium phosphate, magnesium sulfate, alum, magnesium chloride, mono-, di- or tri-basic sodium or potassium salts of phosphoric acid, salts of hydrochloride acid, sodium carbonate, sodium bisulfate and sodium bicarbonate.
  7. 7. A sweetened composition comprising a sweetenable composition and a sweetener composition of any one of claims 1-6.
  8. 8. The sweetened composition of claim 7, wherein the sweetenable composition is a beverage.
  9. 9. The sweetened composition of claim 8, wherein the beverage is a carbonated beverage.
  10. 10. The sweetened composition of claim 9, wherein the carbonated beverage is selected from the group consisting of a cola, ginger ale, root beer, cider, fruit-flavored soft drink and powdered soft drink.
  11. 11. The sweetened composition of claim 10, wherein the carbonated beverage is a soft drink.
  12. 12. The sweetened composition of claim 8, wherein the beverage is a non-carbonated beverage.
  13. 13. The sweetened composition of claim 12, wherein the non-carbonated beverage is selected from the group consisting of fruit juices, beverages with fruit flavorings, vegetable juices, sports drinks, energy drinks, near water, tea, coffee, cocoa and beverages containing milk components.
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WO2004089113A1 (en) * 2003-04-08 2004-10-21 Quest International B.V. Oxigen stable active containing compositions

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US4612942A (en) * 1984-03-08 1986-09-23 Stevia Company, Inc. Flavor enhancing and modifying materials
JP2000236842A (en) * 1998-12-24 2000-09-05 Nippon Paper Industries Co Ltd Stevia sweetener
WO2004089113A1 (en) * 2003-04-08 2004-10-21 Quest International B.V. Oxigen stable active containing compositions

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