WO2012083251A1 - Aliment ou boisson édulcorés avec la monatine et dotés d'un meilleur pouvoir sucrant - Google Patents

Aliment ou boisson édulcorés avec la monatine et dotés d'un meilleur pouvoir sucrant Download PDF

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Publication number
WO2012083251A1
WO2012083251A1 PCT/US2011/065643 US2011065643W WO2012083251A1 WO 2012083251 A1 WO2012083251 A1 WO 2012083251A1 US 2011065643 W US2011065643 W US 2011065643W WO 2012083251 A1 WO2012083251 A1 WO 2012083251A1
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Prior art keywords
monatin
beverage
sweetness
rebaudioside
ppm
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PCT/US2011/065643
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English (en)
Inventor
Jeffrey C. Evans
Melanie Jean Goulson
Original Assignee
Cargill, Incorporated
Yurttas, Nese
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Application filed by Cargill, Incorporated, Yurttas, Nese filed Critical Cargill, Incorporated
Priority to CA2821306A priority Critical patent/CA2821306A1/fr
Priority to AU2011343504A priority patent/AU2011343504A1/en
Publication of WO2012083251A1 publication Critical patent/WO2012083251A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides

Definitions

  • the present disclosure relates generally to a monatin-sweetened food or beverage. Aspects of the disclosure are particularly directed to a monatin-sweetened food or a beverage containing steviol glycosides, resulting in improved sweetener performance.
  • monatin is also known by a number of alternative chemical names, including but not limited to: 2-hydroxy-2-(indol-3-ylmethyl)-4- aminoglutaric acid; 4-amino-2-hydroxy-2-( l H-indol-3-ylmethyl)-pentanedioic acid; 4- hydroxy-4-(3-indolylmethyl)glutamic acid; and, 3-(3 -amino-I ,3-dicarboxy-3-hydroxy-bist-4- yl)indole.
  • monatin has an excellent sweetness quality, and depending on a particular composition, monatin may be several hundred times sweeter than sucrose and in some cases thousands of times sweeter than sucrose.
  • Monatin has four stereoisomeric configurations which exhibit differing levels of sweetness.
  • the R,R stereoisomer of monatin is about 2,000-3,000 times sweeter than sucrose by weight.
  • a monatin composition may include a pure stereoisomer or it may include a mixture of stereoisomers.
  • Monatin can be isolated from the bark of the roots of the plant Sclerochilon UicifoUas.
  • the bark can be ground and extracted with water, filtered and freeze dried to obtain a dark brown, amorphous mass.
  • the mass can be re-dissolved in water and reacted with a cation resin in the acid form, e.g., AG 50W-X8 in the HC1 form (Bio-Rad Laboratories, Richmond, Calif).
  • the resin can be washed with water and the compounds bound to the resin e luted using an aqueous ammonia solution.
  • the eluate can be freeze dried and subjected to aqueous gel filtration. See, e.g., U.S. Pat, No.
  • monatin can be chemically synthesized. See, e.g., the methods of Holzapfet and Olivier, Synth. Commim. 23:251 1 (3993); Holzapfei et a!., Synth. Commim. 38:7025 ( 1994); U.S. Pat. No. 5, 128, 164; U.S. Pat. No. 4,975,298; and U.S. Pat. No. 5,994,559, which are hereby incorporated by reference in their entirety.
  • One pathway described involves converting tryptophan to indole-3-pyruvate ("I-3-P"), converting indole-3-pyruvate to 2-hydroxy 2-(indol-3-ylmethyl)-4-keto glutaric acid (monatin precursor, "MP"), and converting MP to monatin, biologically, for example, with enzymes.
  • This process may be used to make stereoisomer enriched monatin compositions including a monatin composition that comprises greater than 90% R,R monatin.
  • Stevia is a natural sweetener, derived from the South American perennial Stevia rebaudicmct. The sweetness in the stevia plant is attributed to the presence of high potency sweet glycosides.
  • the two major glycosides found in the leaves and stems of the stevia plant are stevioside and rebaudioside A.
  • Rebaudioside A is a desirable glycoside for use in non-caloric sweeteners. It is recognized that other steviol glycosides or a combination of steviol glycosides may be used as a sweetener.
  • Various methods are available for the purification of rebaudioside A from crude rebaudioside A-containmg stevia extracts.
  • high-potency sweeteners allows for the formulation of sweetened beverages with zero, or at least significantly fewer, calories than standard sweetened beverages, an important health and wellness feature as many countries are attempting to address weight-related public health concerns.
  • a naturally occurring high- potency sweetener with a pleasing, sugar-like taste profile such as monatin
  • various high-potency sweeteners, including monatin may present formulation challenges due to varying chemical stability under common beverage conditions, such as low pH, exposure to light, presence of carbonation (“CO 2 "), presence of oxygen ⁇ "O2”), interaction with various flavor components, packaging that is transparent to ultraviolet (“UV”) light or visible light or packaging that is to some extent (3 ⁇ 4 permeable.
  • UV ultraviolet
  • High-potency sweeteners often affect sensory properties beyond simply maximum sweetness intensity. For example, some high- potency sweeteners cause a prolonged sweetness in the mouth, which is not common with caloric sweeteners. Finally, the combination of sweeteners may not behave in predictable ways with respect to sweetness intensity. Selection of appropriate blends of sweeteners may permit more cost-effective blends. The present disclosure addresses one or more of these commercially-relevant concerns.
  • compositions containing monatin and steviol glyclosides are provided herein.
  • a method of improving a sweetener performance in a food product comprising: adding monatin or a salt thereof to the food product ; and adding steviol glycosides to the food product, wherein the steviol glycosides are added in an amount sufficient such that the food product exhibits at least one of a reduction in discoloration and a reduction in off-flavors after exposure to ultraviolet or visible light, as compared to a comparable food product containing monatin without steviol glycosides.
  • the food product comprises between about 10 ppm and about 50 ppm of monatin and between about 10 ppm and about 80 ppm of rebaudioside A. In some embodiments, the food product contains less than about 0.5 ppm of 3-methyl indole after 28 days storage at about 22°C in the continuous presence of fluorescent lighting of about 4,000 lux. In some embodiments, the food product retains at least about 65% of its monatin equivalents after 28 days storage at about 22°C in the continuous presence of fluorescent Sighting of about 4,000 lux, wherein monatin equivalents are defined as monatin and monatin lactone.
  • the food product does not exhibit any appreciable discoloration or appreciable off-flavors after 28 days storage at about 22°C in the continuous presence of fluorescent lighting of about 4,000 lux.
  • the food product exhibits decreased sweetness linger as compared to a comparable food product containing either monatin or stevioi glycosides alone.
  • the food product exhibits greater sweetness than the sweetness expected from sweetness calculations made using the Beidler equation.
  • the food product is a beverage.
  • a method of making a stable beverage comprising: adding monatin or a salt thereof to the beverage; and adding stevioi glycosides to the beverage in an amount sufficient such that the beverage retains at least about 65% of its monatin equivalents after 28 days storage at about 22°C in the continuous presence of fluorescent lighting of about 4000 lux, wherein monatin equivalents are defined as monatin and monatin lactone.
  • the beverage retains at least about 80% of its monatin equivalents after 28 days storage at about 22°C in the continuous presence of fluorescent lighting of about 4,000 lux.
  • the beverage is a carbonated beverage.
  • the beverage is a still beverage.
  • the beverage comprises about 10 ppm to about 80 ppm of rebaudioside A. In some embodiments, the beverage comprises about 10 ppm to about 50 ppm of monatin. In some embodiments, the beverage exhibits decreased sweetness linger as compared to a comparable food product containing either monatin or stevioi glycosides a!one. In some embodiments, the beverage exhibits greater sweetness than the sweetness expected from sweetness calculations made using the Beidler equation.
  • a beverage comprising: about 10 ppm to about 50 ppm of monatin or a salt thereof; and about 10 ppm to about 80 ppm of stevioi glycosides, wherein the beverage retains at least about 65% of its monatin equivalents after 28 days storage at about 22°C in the continuous presence of fluorescent lighting of about 4,000 lux, wherein monatin equivalents are defined as monatin and monatin lactone.
  • the monatin is at least about 90% R,R-monaiin. In some embodiments, the monatin is at least about 95% R,R-monatin.
  • the beverage retains at least about 80% of its monatin equivalents after 28 days storage at about 22°C in the continuous presence of fluorescent lighting of about 4,000 lux.
  • the beverage is a carbonated beverage.
  • the steviol glycosides are at least about 95 wt% rebaudioside A.
  • the steviol glycosides are chosen from the group consisting of rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, stevioside, dulcoside A, steviolbioside, and a combination thereof.
  • the beverage exhibits decreased sweetness linger as compared to a comparable food product containing monatin without steviol glycosides.
  • the beverage exhibits greater sweetness than the sweetness expected from sweetness calculations made using the Beidler equation.
  • a beverage composition comprising: about 10 ppm to about 50 ppm of monatin or a salt thereof; and about 10 ppm to about 80 ppm of steviol glycosides, wherein the beverage composition does not exhibit any appreciable odors or arty appreciable off-flavors after 28 days storage at 22 °C in the continuous presence of fluorescent lighting of about 4,000 lux.
  • the beverage composition is a carbonated beverage.
  • the monatin comprises at least about 90% R,R- monatin.
  • the steviol glycosides include rebaudioside A.
  • the steviol glycosides are at least about 80 wt% rebaudioside A. In some embodiments, the steviol glycosides are at least about 95 wt% rebaudioside A. In some embodiments, the steviol glycosides are chosen from the group consisting of rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, stevioside, dulcoside A, steviolbioside, and a combination thereof. In some embodiments, the beverage exhibits decreased sweetness linger as compared to a comparable food product containing monatin without steviol glycosides, in some embodiments, the beverage exhibits greater sweetness than the sweetness expected from sweetness calculations made using the Beidler equation.
  • a beverage composition comprising: about 10 ppm to about 50 ppm of monatin or a salt thereof; and about 10 ppm to about 80 ppm of steviol glycosides, wherein the beverage does not exhibit any appreciable discoloration after 28 days storage at 22 °C in the continuous presence of fluorescent lighting of about 4,000 lux.
  • the beverage composition is a carbonated beverage.
  • the monatin comprises at least about 90% R,R-monatin.
  • the steviol glycocides include rebaudioside A.
  • the steviol glycosides are at least about 80 wt% rebaudioside A.
  • the steviol glycosides are at least about 95 wt% rebaudioside A. In some embodiments, the steviol glycosides are chosen from the group consisting of rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, stevioside. dulcoside A, steviolbioside, and a combination thereof.
  • the beverage exhibits decreased sweetness linger as compared to a comparable food product containing monatin without steviol glycosides. In some embodiments, the beverage exhibits greater sweetness than the sweetness expected from sweetness calculations made using the Beidler equation.
  • FIG. 1 is a sweetness intensity versus time curve for various blends of monatin and 95wt% rebaudioside A, as compared to a monatin-only sample, a 95 wt% rebaudioside A-only sample, and a sucrose reference sample.
  • monatin has two chira! centers leading to four potential stereoisomeric configurations.
  • monatin is used to refer to compositions including any combination of the four stereoisomers of monatin (or any of the salts thereof), including a single isomeric form.
  • monatin includes any salt thereof.
  • monatin is independent of the method by which the monatin was made, and thus encompasses monatin that was, for example, synthesized in whole or in part by biosynthetic pathway(s), purely synthetic means, or isolated from a natural source.
  • sucrose equivalence value is a measure of sweetness.
  • the SEV is the concentration (% w/v) of a sucrose solution that gives a degree of sweetness that is perceived to be the same degree of sweetness as that of a test sample.
  • the % SEV of an aqueous solution containing monatin is determined through comparison of the monatin- containing solution to a series of sucrose-containing solutions prepared in the same medium.
  • the monatin-containing solution may also include a steviol glycoside, which may contribute sweetness to the solution.
  • an approximate % SEV can be calculated for a solution containing monatin and/or steviol glycosides, based on the concentration response curves for the monatin and/or steviol glycosides in the composition.
  • a "comparable food product” is used herein to compare a monatin- containing food product to essentially the same monatin-containing food product that also includes steviol glycosides.
  • Essentially the same food product means that the food product has essentially the same attributes, properties, and/or composition as the food product it is being compared to, and has been exposed to the same conditions as the food product it is being compared to.
  • a "comparable beverage” is used herein to compare a monatin- containing beverage to essentially the same monatin-containing beverage that also includes steviol glycosides.
  • "food”, “food product”, “foodstuff, and “food composition” include beverages.
  • monatin is subject to degradation in the combined presence of dissolved 0 2 and light resulting in one or more of a loss of sweetness, yellow discoloration, and development of off-flavors or aromas.
  • This light may be in either the visible or UV spectrum
  • an "off flavor” is defined as a sensory experience of a volatile compound(s) that may be detected orthonasally and/or retronasally.
  • the off flavor is a musty off flavor.
  • other negative off flavors may be predictive of monatin 's shelf stability.
  • Off flavors and discoloration may be referred to herein in terms of an "appreciable” off flavor or an “appreciable” discoloration.
  • an appreciable off flavor is detectable nasally by sniffing or retronasally by tasting by a trained human sensory evaluator and an appreciable discoloration is detectable visually by a trained human sensory evaluator.
  • a musty off flavor is believed to be, in part, from formation of 3- methyl indole from monatin.
  • instability may lead to a loss of monatin in a sweetened beverage composition, thus affecting the sweetness properties of the beverage.
  • the inventors unexpectedly observed that a combination of monatin and steviol glycosides in a beverage resulted in the beverage having an improved sweetener performance, as compared to a beverage containing monatin without steviol glycosides.
  • the sweetener performance of a beverage may be defined in terms of its stability, or more specifically, in terms of the absence of off flavors and yellow discoloration after exposure to light over a certain period of time. Sweetener performance may also be described in terms of the preservation or retention of the monatin in the beverage after exposure to light over a certain period of time.
  • sweetener performance of a beverage containing a blend of monatin and steviol glycosides may be described herein in terms of having a reduction in discoloration and/or a reduction in off flavors over a certain period of time as compared to a beverage containing monatin without stevioi glycosides.
  • the sweetener performance in a beverage may, in some cases, also be defined herein in terms of its sweetness linger.
  • sweetness linger is detectable by tasting by a trained human sensory evaluator.
  • the sweetener performance in a beverage may, in some cases, also be defined in terms of its sweetness synergy.
  • sweetness synergy is detectable by tasting by a trained human sensory evaluator.
  • compositions containing a blend of monatin and stevioi glycosides refers to any of the glycosides of the aglycone stevioi (ent-13-hydroxykaur-16-en-1 -oic-acid) including, but not limited to, stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside, rebusoside, steviolmonoside, steviolbioside, and 19- ⁇ - ⁇ glucopyranosol-steviol.
  • stevioi glycosides refers to any of the glycosides of the aglycone stevioi (ent-13-hydroxykaur-16-en-1 -oic-acid) including, but not limited to, stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E
  • stevioi glycosides also includes isomers and derivatives of stevioi glycosides.
  • Reb A refers to a stevia leaf- derived composition comprising greater than about 95% rebaudioside A.
  • RA80 refers to a stevia leaf-derived composition comprising greater than about 80% rebaudioside A.
  • the stevioi glycosides have a rebaudioside A concentration of about 30 to 99.5 wt. % relative to all stevioi glycosides. In some embodiments, the stevioi glycosides have a rebaudioside A concentration of about 60 to 99.5 wt. % relative to all stevioi glycosides. In other embodiments, the stevioi glycosides have a rebaudioside A concentration of about 80 to 99.5 wt. % relative to all stevioi glycosides.
  • the stevioi glycosides have a rebaudioside A concentration of about 95 to 99.5 wt. % relative to all stevioi glycosides, and in yet other embodiments, the stevioi glycosides have a rebaudioside A concentration of about 97 to 99.5 wt. % relative to all stevioi glycosides.
  • the stevioi glycosides in the blend may be essentially ali or predominantly rebaudioside A (predominantly being defined herein as greater than 90% by weight).
  • the stevioi glycosides may include rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, stevioside, dulcoside A. steviolbioside, and a combination thereof.
  • the stevioi glycosides may be predominantly stevioside.
  • the steviol glycosides may be predominantly rebaudioside D.
  • a mixture of any or all of the steviol glycosides may be used.
  • a composition may be described herein in terms of its total indole concentration, which is defined as monatin and its intramolecular rearrangement products - monatin lactone and monatin lactam.
  • a composition may also be described herein as retaining a certain percentage of monatin equivalents, which is defined herein as monatin plus monatin lactone.
  • the addition of steviol glycosides to a monatin-containing composition can result in the composition retaining a larger percentage of monatin equivalents after exposure to light as compared to a sample containing monatin without steviol glycosides. Due to the higher percentage of monatin retained, it is believed that there is less yellow discoloration and less conversion to 3-methyl indole, which may be a significant contributor to a musty off flavor. While not being bound by theory, it is believed that steviol glycosides may inhibit monatin photooxidation.
  • a food product e.g., a beverage
  • monatin and steviol glycosides may exhibit decreased sweetness linger as compared to a comparable food product containing monatin or steviol glycosides alone
  • a food product e.g., a beverage
  • monatin and steviol glycosides may exhibit greater sweetness than the sweetness expected from sweetness calculations made using the Beidler equation, i.e. , sweetness synergy.
  • the concentration of each sweetener correlating to a target sucrose equivalent value (“% SEV") may be calculated from the Beidier curve of concentration response data for each of the individual sweeteners.
  • the standard form of the Beidier equation is:
  • C is the concentration of the sweetener (in mg/L)
  • a and b are coefficients calculated from the empirical measurements.
  • Monatin has a different Beidier equation at neutral pH as compared to acid pH.
  • a beverage composition disclosed herein can include a blend of monatin and steviol glycosides, in some embodiments, the amount of steviol glycosides is equal to or greater than an amount sufficient to cause the beverage composition to exhibit a reduction in discoloration and/or a reduction in off flavors after exposure to ultraviolet and visible light, as compared to a comparable beverage composition containing monatin without steviol glycosides. It is recognized that if steviol glycosides are added to the monatin containing composition, the resulting composition will have a higher sucrose equivalence value ("% SEV").
  • composition containing monatin and steviol glycosides In order for the composition containing monatin and steviol glycosides to have an essentially equal % SEV to the monatin only containing composition, it is recognized that a smaller amount of monatin would be used in order to account for the sweetness from the steviol glycosides.
  • the amount of steviol glycosides is equal to or greater than an amount sufficient such that the beverage retains at least about 65% of its monatin equivalents after 28 days stored at about 22°C in the continuous presence of fluorescent lighting of about 4000 lux. In other embodiments, the amount of steviol glycosides is equal to or greater than an amount sufficient such that the beverage retains at least about 80% of its monatin equivalents under the same conditions. It is recognized that other conditions may be used to define a certain percent retention of monatin equivalents.
  • beverage compositions containing monatin and steviol glycosides may comprise other stability enhancing features, such as, for example, antioxidants.
  • antioxidants such as, for example, antioxidants.
  • monatin is present in an amount that ranges from about 0.0003 to about 1 % of the beverage composition (i.e., about 3 to about 10,000 ppm) (e.g., about 0.0005 to about 0.2%), including any particular value within that range (e.g., 0.0003%, 0.005%, 0.06% or 0.2% of the beverage composition).
  • a beverage composition may comprise about 0.0005 to about 0.005% (e.g., about 0.001 to about 0.0050%) of the R,R monatin, or about 0.005 to about 0.2% (e.g., about 0.01 to about 0.175%) of S,S monaiin.
  • a beverage composition may comprise about 0.001 % to about 0.0050% (i.e. about 10 to about 50 ppm), about 0.001 %» to about 0.0040% (i.e. about 10 to about 40 ppm), or about 0.001 % to about 0.0035% (i.e. about 10 to about 35 ppm) of R,R monatin and about 0.001 % to about 0.008% (i.e.
  • the rebaudioside A may be 95 wt% rebaudioside A.
  • beverages containing monatin and steviol glycosides may have amounts of monatin and/or amounts of steviol glycosides that are outside of the ranges disclosed herein.
  • an amount of monatin in a beverage composition may vary as a function, for example, of the desired sweetness intensity, the beverage formulation, and the stereoisomer ⁇ configuration of the monatin.
  • the amounts of steviol glycosides in a beverage composition may vary as a function, for example, of the profile of the steviol glycosides (i.e. rebaudioside A, rebaudioside D, stevioside, other steviol glycosides, and any combination thereof), the amount of monatin in the beverage, the desired stability profile, and the presence of any other stability enhancing features.
  • Beverage composition refers to a composition that is drinkable as is (i.e., does not need to be diluted, or is "ready-to-drink") or a liquid concentrate or a dry powder that can be diluted or mixed with additional liquid to form a drinkable beverage.
  • Beverage compositions herein include carbonated and non-carbonated soft drinks, coffee beverages, tea beverages, dairy beverages, liquid concentrates, flavored waters, enhanced waters, fruit juice and fruit juice-flavored drinks, sport drinks, and alcohol products. Beverages herein include beverages formed from a powder.
  • beverage compositions comprising monatin and steviol glycosides include other ingredients, such as, for example, a flavoring, coloring, organic acids, inorganic acids, preservatives, caffeine, other sweeteners, and/or poiyols.
  • the monatin and steviol glycosides containing beverage compositions comprise monaiin that consists essentially of S,S or R,R monatin. In other embodiments, the compositions contain predominantly S,S or R,R monatin. "Predominantly” means that of the monatin stereoisomers present in the composition, the monatin contains greater than 90% of a particular stereoisomer. In some embodiments, the compositions are substantially free of S,S or R,R monatin. "Substantially free” means that of the monatin stereoisomers present in the composition, the composition contains less than 2% of a particular stereoisomer.
  • a beverage composition in another aspect, includes a stereoisomerically-enriched monatin mixture.
  • “Stereoisomerically-enriched monatin mixture” means that the mixture contains more than one monatin stereoisomer and at least 60% of the monatin stereoisomers in the mixture is a particular stereoisomer, such as R,R, S,S, S,R or R,S.
  • the mixture contains greater than about 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98%, or 99% of a particular monatin stereoisomer.
  • a beverage composition comprises a stereoisomerically-enriched R.R or S,S monatin.
  • Stepoisomerically-enriched R,R monatin means that the monatin comprises at least 60% R,R monatin.
  • Stepreoisomerically-enriched S,S monatin means that the monatin comprises at least 60% S,S monatin. in other embodiments, "stereoisomerically-enriched” monatin comprises greater than about 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98%, or 99% of R,R or S,S monatin.
  • beverages and other beverage products in accordance with this disclosure may have any of numerous different specific formulations or constitutions.
  • the formulation of a beverage product in accordance with this disclosure can vary to a certain extent, depending upon such factors as the product's intended market segment, its desired nutritional characteristics, flavor profile and the like. For example, it will generally be an option to add further ingredients to the formulation of a particular beverage embodiment, including any of the beverage formulations described below.
  • a beverage in accordance with this disclosure typically comprises at least water, sweetener, acidtilant, and flavoring.
  • Exemplary flavorings which may be suitable for at least certain formulations in accordance with this disclosure include, without limitation, cola flavoring, citrus flavoring, root beer flavoring, and spice flavorings.
  • Carbonation, in the form of carbon dioxide, may be added for effervescence.
  • Natural and synthetic preservatives can be added if desired, depending upon the other ingredients, production technique, desired shelf life, etc.
  • caffeine can be added.
  • Certain exemplary embodiments of the beverages disclosed herein are, without limitation, cola-flavored carbonated beverages, characteristically containing carbonated water, sweetener, kola nut extract, and/or other cola flavoring, caramel coloring, and optionally other ingredients. Additional and alternative suitable ingredients will be recognized by those skilled in the art given the benefit of this disclosure.
  • Some embodiments may be considered still beverages, i.e., beverages which are not carbonated.
  • beverages which are not carbonated Common examples include, without limitation, coffee beverages, tea beverages, dairy beverages, flavored waters, enhanced waters, non-carbonated soft drinks, fruit juice and fruit juice-flavored drinks, sport drinks, and alcohol products other than beer and champagnes.
  • the beverage may contain dissolved carbon dioxide ("C0 2 ”) in amounts sufficient to provide effervescence.
  • C0 2 dissolved carbon dioxide
  • Common examples include, without limitation, carbonated soft drinks, beer and champagnes.
  • Such carbonated beverages typically have carbon dioxide concentrations of about 1 .6 volumes C0 2 per volume of beverage to about 4.2 volumes C0 2 per volume of beverage.
  • Carbon dioxide is typically introduced into a beverage by either fermentation (as in the case of beer and champagnes) or dissolving the carbon dioxide into the beverage under pressure (as in the case of carbonated beverages). Specific methods of beverage carbonation are well known to those skilled in the art.
  • the process of carbonation results in a removal or displacement of dissolved oxygen from the beverage.
  • the dissolved oxygen levels may be reduced or controlled for stability purposes, as disclosed in WO 2010/138513, which is hereby incorporated by reference in its entirety.
  • Lemon-lime flavored carbonated beverages were stored in the dark and evaluated over a seven week period. Solutions of about 9 mM citric acid/trisodium citrate (pH of approximately 3.0) in high purity water were sweetened to about 8.0% SEV (the calculated % SEV of each sample is shown in Table 1 below) with various amounts of monatin and/or Reb A. depending on the intended blend, and then flavored with lemon-lime flavor; and preserved with approximately 150 ppm sodium benzoate. The solutions were carbonated in 10 liter batch sizes using an Armfield carbonator, by adding approximately 3.5 liters of carbon dioxide (“C0 2 ”) per liter of solution before being transferred to twelve ounce clear, glass bottles. Caps were placed on the bottles after filling. The bottles were stored in a dark oven maintained at a temperature of approximately 38°C. Multiple bottles of each sample were created since a bottle was sacrificed when the measurements below were taken.
  • C0 2 carbon dioxide
  • the integrated peak areas for the three compounds were expressed in terms of monatin concentration (mg/L) based on a standard curve prepared for monatin.
  • the extinction coefficient for monatin was applied to estimate concentrations of monatin lactone and monatin lactam since standards for these compounds were unavailable.
  • Total indole concentrations are shown in Table 1 for each of the blends. The percent of the original indole concentration is shown in parentheses. Table 2 shows monatin equivalents, which is defined for purposes herein as monatin and monatin lactone; the percent of the original monatin equivalents is shown in parentheses.
  • Table 2 shows that there is a decrease in monatin equivalents (monatin plus monatin lactone) over time.
  • the decrease in monatin equivalents may be attributed to the formation of monatin lactam from monatin.
  • the presence of Reb A in samples 2 through 5 did not affect the proportion of monatin converted to monatin lactam.
  • compositions from Example 1 were freshly prepared and exposed to light.
  • the solutions were prepared using the same steps described above for Example 1.
  • the bottles containing the solutions were exposed to light in a light box (approximately 4,000 lux light intensity) continuously (24 hours per day), using a rotating carousel to provide even illumination.
  • the source of light was provided by ultra-violet ("UV") light wavelength transmitting bulbs and standard fluorescent bulbs.
  • UV ultra-violet
  • the heat produced by the lights warmed the samples to a temperature of about 22°C.
  • Multiple bottles of each sample were created since each bottle was sacrificed when the measurements below were taken.
  • the samples were analyzed for total indole concentration and monatin equivalents, using the methodology disclosed in Example 1 above.
  • Tables 4 and 5 show that each of the blends of monatin and Reb A, with the exception of sample 3. had a smaller loss of monatin over time, as compared to sample 1 having monatin alone.
  • Sample 3 which contained an amount of Reb A in between the amount in samples 2 and 4, showed the largest loss of monatin over time compared to all samples, including sample 3 .
  • Table 8 shows the various blends of monatin and Reb A.
  • the amount of monatin varied at 13.1 ppm, 17.6 ppm, 21.2 ppm, 25.4 ppm and 31.6 ppm. Except for the sample containing 31.6 ppm monatin, the samples were created by making a composition and dividing it into two equal sized samples, with the first sample containing only monatin and the second sample containing monatin and Reb A.
  • sample 1 contained 33.1 ppm of monatin for a % SEV of 4.2%
  • sample 2 contained 13.1 ppm of monatin and 73.2 ppm of Reb A for a % SEV of 7.2%.
  • This sample preparation method reduced the potential for a formulation error and improved the validity of the resulting comparative data between monatin alone and its corresponding monatin/Reb A blend.
  • Samples 2, 4, 6, and 8 had % SEVs of 7.2%, 7.4%, 7.3%, and 7.3% respectively, and contained a blend of monatin and Reb A. These samples were compared to sample 9 having a % SEV of 7.4% without any Reb A.
  • Lemon-lime flavored carbonated soft drinks were made using the formulas shown in the table below.
  • C is the concentration of the sweetener (in mg/L)
  • b are coefficients calculated from the empirical measurements.
  • Table 16 shows the formulation for each of the blends in Table 15, as well as the 8% sucrose reference sample.
  • a panel of six trained and experienced panelists performed the time intensity evaluation testing. The panelists were instructed to put the entire one fluid ounce sample in his or her mouth and hold for ten seconds while continuously rating the intensity of sweetness, then swallow or spit the sample and continue rating sweetness intensity for one minute. Sweetness intensity was recorded using a computer mouse and Sensory Information Management System ("SIMS") 2000 software (Sensory Computer Systems, Morristown, NJ). The panelists moved the mouse to the right as the sweetness intensity increased and to the left as the intensity decreased. All samples were served at room temperature in a balanced random order, one at a time, and evaluated in duplicate. Panelists took a five-minute break between samples and cleansed their mouth with water and crackers. Results of the time intensity evaluation are shown in Figure 1.
  • SIMS Sensory Information Management System
  • Sweetener samples were prepared to about 8 % SEV for quantitative descriptive analysis ("QDA") as described in Example 5.
  • a panel of nine trained and experienced panelists performed quantitative descriptive analysis ("QDA") on the samples using typical QDA methodology.
  • the panelists tasted a set of control and test samples to develop the ballot with taste attributes, and then were further trained with reference solutions to practice scoring all of the samples on a fifteen-point intensity line scales developed for each attribute.
  • Samples were served at room temperature in a balanced random order, one at a time, and evaluated in duplicate. Panelists had a five- minute break between evaluations and used water and crackers for rinsing. Results of the QDA testing are summarized in Table 1 7.
  • Tabie 17 Quantitative Descriptive Analysis Results
  • Reb A sample scored significantly higher in: time to reach max sweetness (slower onset); herbal flavor; bitter taste/aftertaste; and non-sucrose flavors/aftertaste compared to sucrose, monatin, 20Monatin/20Reb A, and 60Monatin/40Reb A samples.
  • the 80Monatin/20Reb A blend scored the closest to sucrose in herbal, bitter, and non-sucrose flavors attributes followed by monatin and 60Monatin/40Reb A blend.
  • the 80Monatin/20Reb A scored closer to sucrose in herbal, bitter and non-sucrose flavor attributes followed by monatin, and 60Monatin/40Reb A blend.
  • Reb A scored the most different in its flavor/aftertaste profile except for sweetness compared to sucrose.
  • Samples of the solutions were served at ambient temperature (approximately 70 to 72 °F).
  • Each of the panelists then swallowed or spit the sample, and continued rating sweetness intensity of each sample every 10 seconds. All samples were served blind coded in a balanced random order to the panelists. The panelists rated each sample in duplicate. Table 23 shows the mean sweetness intensity of the six panelists at four specific points in time.
  • Each panelist recorded the sweetness intensity at 10 second intervals up to 80 seconds. Each panelist's rating for the duplicate samples was then averaged and plotted. The area under the curve (AUC) was calculated for each sample for each panelist. A linger index was calculated by dividing the AUC for each test sample by the AUC for sucrose for that panelist. This compares each panelist's linger response of the blends relative to that panelist's response to sucrose. The linger index for each panelist, as well as the mean value and standard deviation across panelists, is shown below. Table 24. Linger Index Values
  • Solutions of about 9 mM citric acid/trisodium citrate (pH of approximately 3.0) in high purity water were sweetened with monatin (about 6.4 % SEV) and equimolar stevioi glycoside concentrations (about 1 .6 % SEV), flavored with lemon-iime flavor, and preserved with approximately 1 50 ppm sodium benzoate.
  • the solutions were carbonated in four liter batch sizes using an Arm field carbonator with approximately 3.5 liters of carbon dioxide (“C0 2 ”) per liter of solution and then transferred to 12 ounce clear, plastic bottles. Caps were placed on the bottles after filling. Multiple bottles of each sample were created since a bottle was sacrificed when the measurements below were taken.
  • the yellow color intensity (b*) of each sample was also measured using a HunterLab ColorQuest XE colorimeter (Hunter Associates Laboratory, Inc., Reston, VA). As shown in Table 26, the addition of RA80, Reb B, Reb D, and stevioside did not reduce yellow discoloration relative to the solution containing monatin alone (untreated).
  • the integrated peak areas for the three (3) compounds were expressed in terms of monatin concentration (mg/L) based on a standard curve prepared for monatin. Monatin lactone and monatin lactam were quantified using the monatin standard curve and empirically determined response factors.
  • C/R concentration-response
  • test solution was monatin, Reb A, lo han guo, or a blend. Panelists were instructed to taste the test sample and then to identify the sucrose reference sample that matched the perceived sweetness of the test sample. If the sweetness of the test sample was judged to fall between that of two references, panelists were instructed to estimate sweetness to one decimal point. A rigorous rinsing procedure was adopted following each sip of test or reference solution to minimize the potential for sweetness adaptation and carry-over. Panelists evaluated each sample in duplicate. Results for each test sample were averaged.
  • each sweetener was evaluated at 4 or 5 evenly spaced points across a range of sucrose equivalence values ("% SEV").
  • Monatin was evaluated at 10-40 ppm, stevia at 120-600 ppm, and lo han guo at 200-800 ppm.
  • the sweetener concentrations tested and measured % SEV values are summarized in Table 30.
  • the Beidler equation was applied to these data to create an individual C/R curve for each sweetener.
  • Tabletop sweeteners were formulated to be equisweet to two teaspoons of sucrose (8.5 g).
  • the amount of monatin and Reb A used in each formulation was calculated from the Beidler equations for each sweetener, determined previously in Example 5.
  • % SEV 1 1 .26* [Reb A] / (253+ [Reb A]).
  • Dextrose was considered to be 75% as sweet as sucrose in formulating.
  • Packet weight for each sweetener was 1 gram using dextrose for the majority of the bulk.
  • each sweetener sample for tasting one packet (1 gram) of each sweetener blend was added to 170g of reverse osmosis-purified water and stirred to dissolve. Sensory attributes of these products were determined by an expert panel of sixteen applications and sensory scientists from the Cargill Research Center who were all experienced in working with and tasting monatin and Reb A. Samples were evaluated in individual sensory booths. Panelists were offered water and crackers to rinse their palates and then waited one minute between samples. Three samples were evaluated in each tasting session. All three tasting sessions were completed in one day. The blind coded samples were presented in a balanced rotation and served at room temperature in 2 fluid ounce souffle cups.
  • the greater sweetness intensity may also have driven the higher overall quality, and sweetness onset scores for the 75/25 (4, 1 and 4.9) and 50/50 (4.1 and 4.4) blends relative to either monatin (3,8 and 4,2) or Reb A (3.3 and 4.3) alone.
  • Panelist Number nine trained panelists
  • Panelist Number eleven trained panelists
  • Panelist Number ten trained panelists Table 45. Concentrations of Monatin, Reb A, 80Monatin/20RebA Blend, and Sucrose
  • Panelist Number eight trained panelists
  • Panelist Number nine trained panelists
  • Panelist Number six trained panelists
  • Reb A sample was not included in the testing. Based on sweetness dose response characteristics of Reb A. a 12% SEV level with Reb A as a single sweetener cannot be reached. Therefore Reb A was not included here as the sweetness of all samples initially needed to match at 10 seconds of tasting.
  • Tables 48 to 52 show sweetness intensity scores and the change in the scores over time. Panelists scored sweetness intensity of each sample initially within 10 seconds when the sweetness reached its peak while they were holding the sample in their mouth. Then they spit the samples, and continue evaluating the remaining sweetness (sweetness linger) in their mouth every 10 seconds until panelist no longer received any sweetness. As seen from the tables above, monatin, Reb A, and monatin/Reb A blend (80/20, 60/40, and 50/50) samples scored the same or not statistically significantly different from each other for sweetness intensity at initial 10 seconds of evaluation. In other words initially all of the samples matched in sweetness intensity to each other. Over time a decrease in sweetness intensities were observed for all of the samples.
  • Table 53 shows another example of blending monatin with RA80. As the data in Table 53 show, the 80Monatin/20RA80 blend was significantly lower in sweetness at 20, 40, 50, and 60 seconds of tasting compared to both monatin and RA80 samples indicating less sweetness linger for the blend over time.

Abstract

Cette invention concerne des compositions de monatine contenant des glycosides de stéviol, lesdites compositions présentant un meilleur pouvoir sucrant que les compositions comparables contenant de la monatine mais pas de glycosides de stéviol. Plus précisément, après exposition à la lumière, les compositions pour boisson à base de monatine contenant du rebaudioside A présentent une réduction de la décoloration, une réduction des arômes anormaux et une plus grande conservation des équivalents de monatine par rapport aux compositions comparables contenant de la monatine mais pas de rebaudioside A. Les compositions pour boisson à base de monatine contenant du rebaudioside A présentent une réduction de l'arôme persistant par rapport aux compositions comparables contenant de la monatine mais pas de glycosides de stéviol, et présentent une plus grande saveur sucrée que celle calculée à l'aide de l'équation de Beidler.
PCT/US2011/065643 2010-12-16 2011-12-16 Aliment ou boisson édulcorés avec la monatine et dotés d'un meilleur pouvoir sucrant WO2012083251A1 (fr)

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EP2793615A4 (fr) * 2011-12-20 2016-07-20 Cargill Inc Mélange à faible teneur en monatine et en rébaudioside a
US20180139986A1 (en) * 2016-03-31 2018-05-24 Suntory Holdings Limited Fading reduced beverage
WO2019071220A1 (fr) * 2017-10-06 2019-04-11 Cargill, Incorporated Composés modificateurs sensoriels
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Cited By (14)

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EP2793615A4 (fr) * 2011-12-20 2016-07-20 Cargill Inc Mélange à faible teneur en monatine et en rébaudioside a
RU2658361C2 (ru) * 2013-06-19 2018-06-21 Конаджен Инк. Ребаудиозид е и пищевые продукты, подслащенные ребаудиозидом е
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JP2016529878A (ja) * 2013-06-19 2016-09-29 ファイト テック コーポレーション レバウジオシドｅおよびレバウジオシドｅで甘味化された食品製品
AU2014281353B2 (en) * 2013-06-19 2017-06-29 Conagen, Inc. Rebaudioside E and food products sweetened with rebaudioside E
WO2014205265A1 (fr) * 2013-06-19 2014-12-24 Phyto Tech Corp. Rébaudioside d et produits alimentaires sucrés avec le rébaudioside d
TWI657746B (zh) * 2013-06-19 2019-05-01 美商科納根股份有限公司 含有甜葉菊苷ｅ之可食用產品及使用其製備和強化可食用產品之甜味的方法
US11911497B2 (en) 2013-06-19 2024-02-27 Conagen Inc. Rebaudioside E and food products sweetened with rebaudioside E
US20180139986A1 (en) * 2016-03-31 2018-05-24 Suntory Holdings Limited Fading reduced beverage
WO2019071220A1 (fr) * 2017-10-06 2019-04-11 Cargill, Incorporated Composés modificateurs sensoriels
US11701400B2 (en) 2017-10-06 2023-07-18 Cargill, Incorporated Steviol glycoside compositions with reduced surface tension
US11717549B2 (en) 2017-10-06 2023-08-08 Cargill, Incorporated Steviol glycoside solubility enhancers
US11918014B2 (en) 2019-04-06 2024-03-05 Cargill, Incorporated Sensory modifiers
CN111599416A (zh) * 2020-06-04 2020-08-28 广东省生物工程研究所（广州甘蔗糖业研究所） 一种快速确定甜味剂配方及使用量的方法及其应用

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