RU2783538C2 - Sweetening and taste-masking compositions, products and their use - Google Patents

Abstract

FIELD: food industry.

SUBSTANCE: sweetening composition is proposed, containing a simple mixture of neohesperidine dihydrochalcone and gamma-cyclodextrin, or in which neohesperidine dihydrochalcone and gamma-cyclodextrin are present in the form of a complex, which is an inclusion complex formed between neohesperidine dihydrochalcone and gamma-cyclodextrin. In addition, the invention also relates to the use of the specified composition as an agent for taste masking, to a method for masking unpleasant tastes of edible products.

EFFECT: group of inventions provides high efficiency during the use.

16 cl, 9 dwg, 23 tbl, 13 ex

Description

The present application claims priority on the basis of provisional European patent application EP 17382503.5 filed on 27 July 2017.

FIELD OF TECHNOLOGY

The present invention relates to the field of sweetening and taste masking, in particular, it relates to sweetening and taste masking compositions containing neohesperidin dihydrochalcone.

BACKGROUND OF THE INVENTION

Sugar-sweetened foods and drinks are associated with an increased risk of obesity, diabetes, and heart disease, and are detrimental to dental health. Therefore, it is now generally accepted that consumption of sucrose, as well as other high-calorie sweeteners such as glucose, fructose, or high fructose corn syrup, should be reduced.

This need to reduce sugar intake is driven by the use of low calorie sweeteners such as stevia extract, arhat, saccharin, aspartame, acesulfame K, cyclamate, sucralose, or neohesperidin dihydrochalcone, among others.

In particular, neohesperidin dihydrochalcone (also known as neohesperidin DC or NHDC) is a well-known low-calorie sweetener that is a derivative of the natural product neohesperidin, a flavone found in citrus fruits. It is a high intensity sweetener that is about 1500 times sweeter than sucrose and is suitable for sweetening foods, beverages, and pharmaceutical products.

However, the use of high-intensity, low-calorie sweeteners as sugar substitutes presents some problems, since not only the intensity of the sweet taste is important, but also other organoleptic properties are required. Thus, it is generally accepted that an ideal sweetener should have a pleasant taste, with an early onset and no long aftertaste. In fact, the more a sweetener is similar in taste and action to sucrose, the better the consumer satisfaction. On the other hand, for economic reasons, it is also desirable to provide the desired degree of sweetness with the use of a minimum amount of sweetener.

Thus, for example, although neohesperidin dihydrochalcone is an intense sweetener, it has the disadvantage of a relatively slow onset of sweet taste and a long aftertaste reminiscent of licorice, which hinders its wider use as a sugar substitute.

Several solutions have now been proposed in the art to overcome these disadvantages and to improve the taste profile of low calorie sweeteners, in particular neohesperidin dihydrochalcone.

The first strategy combines low-calorie sweeteners with high-calorie sweeteners. Low calorie sweeteners, to some extent, provide the ability to reduce the content of caloric sweeteners. On the other hand, the amount of low calorie sweetener is low enough that it does not significantly affect the sweetening profile of the final sweetener blend. In this context, neohesperidin dihydrochalcone is a very promising potential low calorie sweetener because it has a very high synergy with caloric sweeteners. This synergy allows for a more effective reduction in the amount of caloric sweetener than would be expected without compromising the sweetening profile. Of course, there is interest and need to further enhance this synergy to further reduce caloric sweeteners.

The second strategy is to use mixtures of two or more low calorie sweeteners, since some such mixtures provide a synergistic effect, so the desired degree of sweetness can be achieved with less sweeteners, which saves money. In addition, some of these mixtures also provide qualitative synergy, ie. the taste quality of these mixtures is often better than the taste quality of the individual components, for example undesirable aftertaste can be reduced.

For example, US Pat. No. 4,158,068 describes that the use of a mixture of acesulfame K with other sweeteners, such as neohesperidin DC, provides a sweet taste that is more similar to sucrose than when these sweeteners are used alone.

In addition, European Patent Application EP0507598-A1 describes that the combination of neohesperidin DC and sucralose provides synergy as well as improved sweet taste quality.

Chung HJ ., The effect of β-cyclodextrin on the taste quality of neohesperidin dihydrochalcone , J. Food Sci. Nutr., 1996, 1(2), 186-189, studied the effect of beta-cyclodextrin on the sweetness and aftertaste of NHDC and concluded that the addition of beta-cyclodextrin reduced both the intensity of the sweet taste and the aftertaste of NHDC. It was found that the intensity of the sweet taste decreases faster than the aftertaste. Thus, the author concluded that by using beta-cyclodextrin it is not possible to reduce the aftertaste of NHDC while maintaining a sweet taste. In other words, the quality of the sweet taste of the resulting mixture was superior to that of pure NHDC.

Thus, there is a need in the art for new high intensity sweetener compositions with improved characteristics, namely those that can provide the desired sweet taste with a minimum amount of sweetener and that have improved taste quality, no aftertaste and taste more similar to sucrose. .

On the other hand, another related problem arises from the unpleasant taste of many substances that are often found in foods, beverages and pharmaceutical products.

The main tastes or taste sensations that are generally perceived as unpleasant are bitterness, astringency and metallic tastes.

Only rare consumers accept the bitter/astringent taste of foods and drinks, such as in black coffee, black or green tea, beer, red wine, grapefruit products, or bitter lemon. In most other cases, these flavors are undesirable and should be excluded or masked.

For example, many substances known to be healthy and intentionally added to healthy food formulations are nonetheless perceived by consumers to be unfavorable in terms of taste. This may be the bitter taste of certain vitamins, minerals, peptides, or protein hydrolysates, or the bitter or astringent taste of certain plant phenols, flavonoids, isoflavones, terpenes, and glucosinolates, which are reported to have positive antioxidant and anticarcinogenic properties.

Another example is the bitter aftertaste caused by potassium chloride, which is increasingly being used to provide a salty taste to foods, as a healthier substitute for sodium chloride.

A particularly problematic group of consumer products in terms of taste are pharmaceutical products, which often contain active ingredients that taste bitter, astringent or metallic. Such adverse perceptions may even undesirably affect patient compliance, especially in those populations that are particularly susceptible to unpleasant tastes, such as children.

Thus, since the taste of a consumer product plays an important role in consumer perception, attempts have been made to suppress or reduce unpleasant tastes in consumer products, such as foods, beverages, and pharmaceutical products.

Depending on each particular taste and each particular consumer product, various taste masking solutions can be used, as detailed in the prior art, for example, some possible strategies are to partially exclude bitter substances, to provide them with a coating or microencapsulation, in the addition of flavors and/or sweeteners or in the addition of special taste-masking agents.

The use of taste-masking agents, which can also modify, reduce or suppress unpleasant tastes, in particular bitter, astringent or metallic tastes, has been found effective in many specific applications.

A significant number of substances have been described in the art for use as taste masking agents in foods and pharmaceuticals, as shown, for example, by Ley JP in Masking bitter taste by molecules, Chem. Percept., 2008, 1, 58-77. Among the many taste masking agents listed are some sweeteners such as thaumatin and neohesperidin dihydrochalcone; polymers and complexing agents such as cyclodextrins, poly-γ-glutamic acid and chitosan; neodiosmin; L - ornithine and its derivatives, such as L-ornithyl-β-alanine or L-ornithinyltaurine; certain dipeptides containing aspartic acid, such as the potassium salt of L-aspartyl-L-phenylalanine; sodium salts of saturated fatty acids such as stearate, palmitate and sodium laurate; organic phosphates, phosphonates, vanadates, thiophosphates and biphosphates; flavanones such as eriodictyol and homoeriodictyol; and many others.

In particular, neohesperidin dihydrochalcone has been described as an effective taste masking agent, in particular, it is used to mask the bitter taste of substances such as paracetamol, dextromethorphan and other pharmaceuticals, as well as in specialty food products, as described in Borrego et al., Neohesperidin Dihydrochalcone, in: L O'Brien Nabors, eds. Alternative Sweeteners, fourth edition, CRC Press, 2012, 94-95.

However, in order to achieve an acceptable degree of taste masking, it is usually necessary to use a significant amount of taste masking agent, which is unacceptable in terms of costs and additional problems.

Thus, there is a need in the art for new taste masking compositions that can effectively modify, reduce, or suppress unpleasant tastes and that require the use of a smaller amount of taste masking composition.

BRIEF DESCRIPTION OF GRAPHICS

In FIG. 1 shows the concentrations of neohesperidin dihydrochalcone (NHDC) that provide sweetness equal to that of 1% and 3% sucrose solutions in water. The x-axis shows the two levels of sweetness tested, i.e. 1% and 3% sucrose solutions, and the y-axis represents the concentrations of NHDC required to achieve these levels of sweetness. Subsequent trials used neohesperidin dihydrochalcone (NHDC, black circles) alone, in combination with gamma-cyclodextrin (black squares, diamonds, triangles, crosses and a straight line - examples A - E), and in combination with beta-cyclodextrin (gray squares and diamonds). A partial overlap was observed between the lines corresponding to examples D (NHDC:gCD 1:6) and E (NHDC:gCD 1:10).

In FIG. 2 is an enlarged view of the graph shown in FIG. 1, which further demonstrates concentrations of neohesperidin dihydrochalcone (NHDC) in combination with gamma-cyclodextrin equal in sweetness to 1% and 3% sucrose solutions in water, in a 1:1 molar ratio of NHDC:gamma-cyclodextrin (Example A, squares), 1 :3 (example B, diamonds), 1.5:1 (example C, triangles), 1:6 (example D, crosses) and 1:10 (example E, straight line; partial overlap with the line corresponding to example D) .

In FIG. 3 shows the sweetening efficacy of the test compositions compared to sucrose, at different levels of sweetness. The y-axis represents the relative sweetening potency and the abscissa represents the level of sweetness, namely the sweetness of 1% and 3% sucrose solutions. The experimental substances were pure neohesperidin dihydrochalcone (NHDC, black circles) and in combination with gamma-cyclodextrin in a molar ratio of NHDC:gamma-cyclodextrin 1:1 (example A, squares), 1:3 (example B, diamonds), 1.5 :1 (example C, triangles) and 1:6 (example D, crosses).

In FIG. 4 is a spider diagram illustrating the sensory profile of sucrose (triangles), neohesperidin dihydrochalcone (NHDC, circles) and two compositions containing NHDC and gamma-cyclodextrin in a 1:1 molar ratio of NHDC:gamma-cyclodextrin (example A, squares) and 1: 3 (example B, diamonds). The perceived characteristics of perception were overall sweetness, time to first perception of sweetness, time to maximum sweetness, menthol/licorice flavor and mouthfeel, on a scale of 0 to 5.

In FIG. 5 shows the ¹ H-NMR spectrum in D ₂ O at 400 MHz of the complex of Example A having a 1:1 molar ratio of NHDC:gamma-cyclodextrin.

In FIG. 6 shows the ¹ H-NMR spectrum in D ₂ O at 400 MHz of gamma-cyclodextrin.

In FIG. 7 shows ¹ H-NMR spectrum in deuterated DMSO at 400 MHz NHDC.

In FIG. 8 schematically shows one glucopyranose ring forming part of the gamma-cyclodextrin structure, indicating the protons described in the ¹ H-NMR spectrum.

In FIG. 9 schematically shows the aglycone part of the neohesperidin dihydrochalcone structure, indicating the protons described in the ¹ H-NMR spectrum.

OBJECT OF THE INVENTION

In a first aspect, the present invention relates to a sweetener composition containing neohesperidin dihydrochalcone and gamma-cyclodextrin.

The second aspect of the present invention relates to the use of a composition containing neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin as a taste masking agent.

Another aspect of the present invention relates to the use of a sweetening composition for sweetening edible products.

Another aspect of the present invention relates to an edible product containing a sweetening composition.

Another aspect of the present invention relates to an edible product that contains an unpleasant taste and a taste masking composition that contains neohesperidin dihydrochalcone and a cyclodextrin selected from beta- and gamma-cyclodextrin.

DETAILED DESCRIPTION OF THE INVENTION

In a first aspect, the present invention relates to a sweetener composition containing neohesperidin dihydrochalcone and gamma-cyclodextrin.

In a second aspect, the present invention relates to the use of a composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin as a taste masking agent.

The inventors of the present invention have developed a novel sweetening composition containing a combination of neohesperidin dihydrochalcone (NHDC) and gamma-cyclodextrin, which unexpectedly provides an excellent synergistic effect, achieving the desired level of sweetness with the use of less NHDC. In addition, not only is the intensity of the sweet taste synergistically enhanced, but the sweet taste quality of this combination is markedly superior to that of pure NHDC, for example, the long aftertaste is significantly reduced, and the flavor time is also shortened, resulting in an improved overall flavor profile more similar to the flavor profile provided by sucrose.

In addition, it has also been unexpectedly found that compositions containing a combination of NHDC with beta-cyclodextrin or gamma-cyclodextrin exhibit effective taste-masking synergy, i.e., the taste-masking effect achieved by using said combination, usually to mask a bitter or astringent taste. , higher than the sum of the effects of each individual substance.

In the text of the present description, as well as in the claims, singular forms should be understood as including also plural forms, unless the context clearly indicates otherwise.

In this context, the term "about", used before a quantitative value, should be understood as including a specific quantitative value, as well as deviations of no more than ±10% of this value, preferably no more than ±5% of this value.

Neohesperidin dihydrochalcone

Neohesperidin dihydrochalcone (CAS number 20702-77-6) is a well-known synthetic intense sweetener, sometimes abbreviated as neohesperidin DC or NHDC. It is also known by the chemical name 1-[4-[[2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3- hydroxy-4-methoxyphenyl)propan-1-one.

Structurally, it is analogous to neohesperidin, a bitter flavonone found in citrus fruits. NHDC can be synthesized either from naringin, which is derived from grapefruit ( Citrus paradisi ), or from neohesperidin, which can be extracted from bitter orange ( Citrus aurantium ), as described, for example, in Borrego et al., Neohesperidin Dihydrochalcone, in: L O 'Brien Nabors, ed. Alternative Sweeteners, fourth edition, CRC Press, 2012, 117-131.

In addition, NHDC is widely available commercially, for example from Interquim S.A or Ferrer HealthTech.

Cyclodextrin

Cyclodextrins are cyclic oligosaccharides derived from starch. The cyclic structure of cyclodextrins is usually described as having a conical or toroidal shape, where the primary and secondary hydroxyl groups are oriented outward, and non-polar hydrogen atoms and ether-linked oxygen atoms are located inside the molecule, forming a hydrophilic outer surface and a non-polar, hydrophobic inner cavity.

Due to this three-dimensional structure, cyclodextrins can act as hosts to form inclusion complexes with a wide range of guest molecules, usually hydrophobic molecules or molecules containing a hydrophobic moiety. In such inclusion complexes, the guest molecule is held at least in part within the hydrophobic cavity of the cyclodextrin host molecule.

In particular, gamma-cyclodextrin (β-cyclodextrin, CAS number 17465-86-0), also known as cyclomaltooctaose or cyclooctaamylose, is a cyclodextrin containing 8 (1→4)-linked α-D-glucopyranosyl units.

Gamma-cyclodextrin can be prepared from starch by the action of the enzyme cyclodextrin glycosyltransferase (CDTGase; ED 2.4.1.19), for example, as described in Hedges A, Cyclodextrins: Properties and Applications, in: Starch. Chemistry and Technology, BeMiller J and Whistler R, eds., Food Science and Technology International Series, third edition, Elsevier, 2009, 833-851.

Gamma-cyclodextrin is readily available from several commercial sources such as Wacker Chemie and Roquette.

Beta-cyclodextrin (β-cyclodextrin, CAS number 7585-39-9), also known as beta-cycloamylose, beta-dextrin, betadex, cycloheptaamylose, cycloheptaglucan, or cyclomaltoheptose, is a cyclodextrin containing 7 (1→4)-linked α -D-glucopyranosyl units.

Beta-cyclodextrin can be prepared from starch by the action of the enzyme cyclodextrin glycosyltransferase (CDTGase; ED 2.4.1.19), for example, as described in Hedges A, Cyclodextrins: Properties and Applications, in: Starch. Chemistry and Technology, BeMiller J and Whistler R, eds., Food Science and Technology International Series, third edition, Elsevier, 2009, 833-851.

Beta-cyclodextrin is readily available from several commercial sources such as Wacker Chemie and Roquette.

Sweetening composition

The sweetening composition according to the present invention contains neohesperidin dihydrochalcone and gamma-cyclodextrin.

Said sweetener composition contains a simple mixture of neohesperidin dihydrochalcone and gamma-cyclodextrin, as well as a variant in which both components are presented in the form of a complex.

In one embodiment, the proposed sweetening composition is a mixture of both components.

The composition of this embodiment may be prepared by simple dry blending of NHDC and gamma cyclodextrin using any suitable mixing device, for example using a drum mixer or a paddle mixer.

In another embodiment of the present invention, NHDC and gamma-cyclodextrin are in the form of a complex.

In such a complex, the NHDC is presumably inserted, at least partially, into the gamma-cyclodextrin cavity to form an inclusion complex. However, the term "complex" as used herein includes other possibilities, including additional non-stoichiometric interactions between NHDC and gamma-CD to form a supramolecular complex.

Such a complex is usually prepared by dissolving the gamma-cyclodextrin in a suitable solvent, preferably water, followed by the addition of NHDC to the resulting solution and isolation of the complex from the solution.

The concentration of gamma-cyclodextrin in such a solution is usually 1-20% w/v, preferably 5-10% w/v. NHDC is added to said solution in an amount corresponding to the desired molar ratio of NHDC:gamma-cyclodextrin in the complex.

The mixture is usually stirred until complete dissolution, typically over a period of 10 minutes to 3 hours, at a temperature typically between 20°C and 60°C, preferably between 20°C and 25°C.

To isolate the solid complex, the solvent is removed by any suitable means, such as freeze-drying, or it can be evaporated under reduced pressure.

The molar ratio of NHDC:gamma-cyclodextrin in the sweetening composition according to the present invention is typically 1.5:1 to 1:10, preferably 1.5:1 to 1:6, more preferably 1.2:1 to 1:4 , even more preferably from 1.1:1 to 1:3.5 and even more preferably from 1:1 to 1:3.

In a preferred embodiment of the present invention, the molar ratio of NHDC:gamma-cyclodextrin is about 1:1.

In another preferred embodiment, the molar ratio of NHDC:gamma-cyclodextrin is about 1:3.

The compositions of the present invention provide an excellent synergistic effect such that the gamma-cyclodextrin unexpectedly significantly enhances the sweet taste of NHDC. For example, as described in Example 3 (Table 3), in a perception test conducted by a certified tasting panel, it was observed that 5 ppm NHDC was needed to achieve a level of sweetness equivalent to that of a 1% sucrose solution in water using pure NHDC. In contrast, when used in combination with gamma-cyclodextrin, significantly less NHDC is needed to achieve the same effect (only 3.5-3.9 ppm in examples A-E). Similarly, 24 ppm NHDC is needed to achieve a level of sweetness equal to that of 3% sucrose in water when using pure NHDC, and when used in combination with gamma-cyclodextrin, smaller amounts of NHDC are also needed (only 12.2-13.5 ppm in examples A-E).

In addition, for compositions containing beta-cyclodextrin instead of gamma-cyclodextrin, exactly the opposite effect was unexpectedly observed (see comparative examples A and B in table 3), i. when using pure NHDC, larger amounts of NHDC were required to achieve the same level of sweetness (e.g., 6.1 ppm and 7.7 ppm NHDC in said composition compared to 5 ppm pure NHDC to achieve a sweetness level of 1% sucrose; and 28.8 ppm and 28.3 ppm NHDC in said composition compared to 24 ppm pure NHDC to achieve a sweetness level of 3% sucrose).

The effective sweet taste synergy obtained with the sweetener composition of the present invention, which contains gamma-cyclodextrin and NHDC, is also plotted in FIG. 1 and 2.

In addition, a quantitative calculation of such a synergistic effect is also presented (example 3, tables 5 and 6). It can be seen that the compositions according to the present invention show a noticeable sweetening synergy, namely more than 15% for the sweetness level of 1% sucrose, preferably from 18% to 40% for the sweetness level of 1% sucrose, in particular 29.9% and 38.9 % for a sweetness level of 1% sucrose for a composition having a molar ratio of NHDC to gamma-cyclodextrin of 1:1 and 1:3, respectively; and a sweetening synergy greater than 60% for a sweetness level of 3% sucrose, preferably from 60% to 95%, in particular 76.5% and 92.3% sweetening synergy for a sweetness level of 3% sucrose - for a composition having a molar ratio of NHDC to gamma-cyclodextrin 1:1 and 1:3, respectively. Conversely, the compositions of Comparative Examples containing beta-cyclodextrin show negative synergy, ie. this combination exhibits a sweetness reduction effect.

This inhibitory effect of beta-cyclodextrin on the sweet taste of NHDC is in accordance with the prior art, as described, for example, in Chung HJ ., The effect of β-cyclodextrin on the taste quality of neohesperidin dihydrochalcone , J. Food Sci. Nutr., 1996, 1(2), 186-189.

Another property of the sweetening compositions of the present invention is that their relative sweetening potency decreases less as the level of sweetness increases, compared to pure NHDC.

The relative sweetening potency of a given compound at a given level of sweetness refers to how many times that compound is sweeter than sucrose, and it can be calculated as the ratio between the concentration of sucrose and the equal sweetness concentration of that compound.

A test was carried out to evaluate the enhancement of the relative sweetening effectiveness of the compositions according to the present invention (Example 4). The results demonstrate (Table 7) that while sweetening potency declines more rapidly with increasing sweetness levels when using pure NHDC, the sweetening potency of the sweetening compositions of the present invention shows a markedly slower decline. This effect is better understood with reference to FIG. 3.

Another advantage of the sweetener composition of the present invention is that it provides an overall flavor profile that is closer to that of sucrose than that of pure NHDC. The taste profiles of sucrose, NHDC and two compositions according to the present invention (Example 5) were tested using each sample at a concentration equal in sweetness to 3% sucrose. The certified tasting panel evaluated the following perception parameters on a scale from 0 to 5: time to the first sensation of sweetness (or the period of appearance, i.e. the period of time preceding the onset of the appearance of sweetness), time to maximum sweetness (i.e. the period of time preceding maximum perception of sweetness), duration of action (i.e., the period of time until the sweet taste disappears), menthol/licorice flavor (i.e., the perception of any taste other than sweet, namely menthol and/or licorice), and sensation in the mouth (described as density, i.e. perceptible viscosity in the mouth).

The results obtained, shown in Table 8 of Example 5, demonstrate that the NHDC taste profile differs markedly from the desired sucrose profile and has a much longer time before the first detection of the sweet taste and until maximum sweetness is reached, the duration of action is also longer, it causes noticeable off-flavors and less pronounced sensation in the mouth.

In contrast, the sweetening agent of the present invention has a flavor profile that is closer to that of sucrose. Thus, compared to NHDC, the time to appearance and maximum sweetness is reduced, the duration of action and off-flavours are also reduced, and the mouthfeel is improved.

In FIG. 4 shows the results of this comparative taste analysis in the form of a spider chart. This diagram clearly shows how gamma-cyclodextrin brings the taste profile of NHDC closer to that of sucrose. The best results in terms of flavor profile are achieved with example B, which contains a molar ratio of NHDC:gamma-cyclodextrin of 1:3.

Use as a sweetener

Due to the observed sweetening synergy and the improved overall flavor profile achieved, the sweetening composition of the present invention is particularly suitable for sweetening all kinds of edible products.

Thus, in a further aspect, the present invention relates to the use of the composition described above for sweetening a comestible.

In a further aspect, the present invention relates to a method for sweetening a edible product, comprising the step of adding the sweetening composition described above to the edible product. Typically, an effective amount of the sweetening composition is added.

The term "edible product" in the context of the present invention refers broadly to any substance suitable for sweetening intended for oral ingestion by a human or animal, and includes substances that are drunk, eaten, ingested or otherwise consumed products, namely food and pharmaceutical products. In addition, the term "edible product" also includes substances that are not intended to be swallowed, but which are initially placed in the mouth and then spit out, such as chewing gums and oral care compositions, such as, for example, mouthwashes. , toothpastes or tooth gels.

In one embodiment of the present invention, the comestible product is selected from the group consisting of foods, pharmaceuticals, and oral care compositions; preferably selected from foods and pharmaceuticals.

In another embodiment of the present invention, the edible product is a food product.

In another embodiment of the present invention, the comestible product is a pharmaceutical product.

The expression "food" in this context means any edible product intended for human or animal nutrition, and includes solid, semi-solid and liquid products, including also beverages. The expression "food product" also includes products that are intended only for partial consumption and subsequent spitting out of the mouth, in particular chewing gum.

Beverages suitable for sweetening with the composition of the present invention may be, without limitation, any type of sweetened beverage, carbonated or non-carbonated, alcoholic or non-alcoholic, and include, but are not limited to, fruit-flavored soft drinks, sodas, cola, sports drinks, and in general, any beverage containing and/or flavored with, for example, fruits, vegetables, aromatic plants, tea, coffee or cocoa; they also include drinks containing, for example, wine or beer. The beverage category includes ready-to-drink beverages as well as other forms such as powders, granules, tablets or liquid concentrates that are intended to be diluted with water.

Other food products are, for example, baked goods such as bread, pies, biscuits, muffins and, in general, any kind of baked goods; also dairy products such as yogurt, drinking yogurt, frozen yogurt, milk, milk drinks, condensed milk, cream, cheese or ice cream; soy products such as soybean oil or soy lecithin; confectionery products such as chocolate, caramel, candies, marzipan or chewing gums; cereal products such as breakfast cereals, cereal sticks, energy/nutrition bars or cereals; fruit products such as jams, fruit purees, canned fruits or sauces; vegetable products such as sauces, dried vegetables, canned vegetables, or frozen vegetables; oil-based products and emulsions such as mayonnaise and some dressings; and many others.

The food category also includes, in particular, nutritional or dietary supplements, i. foods enriched with certain nutritional ingredients, such as vitamins, minerals, amino acids, proteins, botanicals, enzymes, or other substances intended to supplement the human diet, and which may be in any suitable food product form, such as beverages or, for example, bars.

Also included in the expression "food product" are any types of dried products, such as dessert mixes or dried products ready to eat.

Food products also include, in particular, any food intended for animal nutrition.

Suitable pharmaceutical products for sweetening with the composition of the present invention include dosage forms containing any drug for oral administration, for human or veterinary use, and include any kind of nutritional supplement, as well as, for example, vitamins, minerals, and mixtures thereof. The pharmaceutical products may be in any form suitable for oral administration well known to those skilled in the art, e.g., solid forms such as tablets, chewable tablets, disintegrating tablets in the mouth (ODT), sublingual tablets, disintegrating films in the mouth ( flash films), lozenges, chewing gums or powders; or liquid forms such as drops, syrups or suspensions; or alternatively in the form of powders, granules or tablets intended to be dissolved in a liquid for administration, for example in the form of effervescent tablets.

It should be understood that the above examples are not limiting and any edible product suitable for sweetening may be suitable for sweetening with the composition of the present invention.

The term "sweetening" in this context refers to the usual meaning of this term, ie. to provide a sweet taste to the edible product. It should be understood that such a sweetening effect includes embodiments in which the sweetening composition is the only source of sweet taste in the product, as well as other alternative implementations in which it is used in combination with other sweeteners.

Thus, in one embodiment, the sweetening composition of the present invention is used in combination with other sweeteners, e.g., other high intensity sweeteners (low calorie sweeteners) such as stevia extracts, arhat, acesulfame K, aspartame, cyclamate, neotame, saccharin, sucralose, thaumatin or mixtures thereof; and/or with carbohydrate sweeteners (caloric sweeteners) such as sucrose, glucose, fructose and mixtures thereof.

If the sweetened comestible is a food, in particular for human consumption, the sweetening composition is usually used in combination with a carbohydrate sweetener. In this particular embodiment, the composition is used as a sugar substitute or sugar reducing agent and its purpose is to reduce the amount of sugar contained in a food product as effectively as possible without changing the sugar-like taste of the product. Indeed, the sweet taste provided by carbohydrate sweeteners is generally best accepted by consumers, while in general, the taste profiles of high intensity sweeteners may not fully mimic the taste of sugar, due to their different onset time, duration of action, mouthfeel and/or aftertaste.

Surprisingly, it has been found that the use of a composition according to the present invention makes it possible to reduce the amount of NHDC required to replace some of the sugar in the edible product, namely the food product. For example, as shown in Example 6, the proposed composition was used to sweeten an orange soft drink to replace some of the high fructose corn syrup (HFCS) originally used as a sweetener. Using pure NHDC, the maximum sugar reduction with no change in taste perceived by the accredited tasting board was found to be 10% HFCS using 10 ppm NHDC as a substitute. However, using the composition containing NHDC and gamma-cyclodextrin according to the present invention, the same percentage of sugar replacement is achieved with only 4.5 ppm NHDC, also without any change in the overall taste profile.

In addition, the proposed composition is also effective in increasing the proportion of sugar that can be replaced in a sweetened comestible product without measurably changing the flavor profile. For example, as described in Example 7, using pure NHDC as a sugar substitute, a 15% reduction in the sucrose content of an orange juice soft drink can be achieved, while a combination of NHDC and gamma-cyclodextrin can reduce the sugar content by up to 25%. . Similarly, as described in Example 8, using pure NHDC as a sugar substitute, a 10% reduction in the sugar content of a dark chocolate product can be achieved; however, when used as a sugar substitute, the composition of the present invention can reduce the sugar content of said chocolate product by up to 28%.

Thus, the composition of the present invention containing NHDC and gamma-cyclodextrin improves the efficiency of sugar replacement by NHDC, i.e. for a given proportion of sugar to be replaced, it allows less NHDC to be used, and in addition, it also allows a greater portion of the sugar in the comestible to be replaced without any perceptible change in flavor than using NHDC alone.

In one embodiment of the present invention, the sweetening composition is used as a sugar substitute. In this context, sugar includes any suitable carbohydrate sweetener, such as sucrose, glucose, fructose, and mixtures thereof.

The percentage of sugar that is replaced by the sweetening agent varies depending on the particular food product. For example, the percentage of carbohydrate sweetener to be replaced is typically 5-60%, preferably 10-30%, which percentage refers to the weight of carbohydrate sweetener replaced relative to the total original carbohydrate content.

Typically, the use of the proposed composition for sweetening a edible product includes adding said composition to the edible product.

The sweetening composition according to the present invention can be added to the edible product in a conventional manner, similar to conventional sweetening agents. For example, it may be added to a pharmaceutical product along with other pharmaceutical excipients, or it may be added to food products by introduction at some stage in a process known to those skilled in the art of pharmaceutical or food technology.

In an alternative embodiment, the sweetener composition may be produced in situ such that both components, i. The NHDC and gamma-cyclodextrin may be added separately, preferably sequentially, during the manufacture of the comestible, usually followed by thorough mixing.

In a further aspect, the present invention relates to a method for sweetening a comestible product, comprising adding the sweetening composition described above to the comestible product.

In a further aspect, the present invention also relates to a sweetened edible product containing the sweetening composition described above.

The amount of sweetening composition used to sweeten a comestible or included in a sweetened comestible is an "effective amount" for sweetening it, i.e. to provide a sweet taste to the edible product. This "effective amount" varies widely depending on the particular product, as well as depending on the desired degree of sweetness. Those skilled in the art can easily determine the appropriate amount of the composition to be added to the comestible product, depending on the particular case.

For example, the amount of the sweetening composition used to sweeten the comestible or contained in the sweetened comestible may be 1-5000 ppm, preferably 1-500 ppm, more preferably 1-200 ppm, based on the total weight of the comestible. The total weight of the comestible product also includes the weight of the sweetener composition added.

Aspects of the present invention that relate to a sweetener composition containing NHDC and gamma-cyclodextrin can be defined in accordance with the following implementation options:

1. A sweetener composition containing neohesperidin dihydrochalcone and gamma-cyclodextrin.

2. Sweetening composition according to embodiment 1, characterized in that it is a mixture of neohesperidin dihydrochalcone and gamma-cyclodextrin.

3. Sweetening composition according to embodiment 1, characterized in that neohesperidin dihydrochalcone and gamma-cyclodextrin are presented in the form of a complex.

4. Sweetening composition according to any one of embodiments 1-3, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1.5:1 to 1:10.

5. Composition according to any one of embodiments 1-4, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1.5:1 to 1:6.

6. Composition according to embodiment 5, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1.2:1 to 1:4.

7. Composition according to embodiment 6, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1.1:1 to 1:3.5.

8. Composition according to embodiment 7, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1:1 to 1:3.

9. A composition according to any one of embodiments 1-8, wherein the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is about 1:1.

10. Composition according to any one of embodiments 1-8, characterized in that the molar ratio of neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.1 : 1 ± 0.1.

11. Composition according to embodiment 10, characterized in that the molar ratio of neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.05: 1 ± 0.05.

12. Composition according to any one of embodiments 1-11, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is 1:1.

13. A composition according to any one of embodiments 1-8, wherein the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is about 1:3.

14. Composition according to any one of embodiments 1-8, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is 1±0.1:3±0.3.

15. Composition according to embodiment 14, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is 1±0.05:3±0.15.

16. Composition according to any one of embodiments 1-15, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is 1:3.

17. The use of a composition according to any one of embodiments 1-16 for sweetening a comestible product.

18. Use according to embodiment 17, wherein the edible product is selected from a food product and a pharmaceutical product.

19. Use according to embodiment 17 or 18, wherein the edible product is a food product.

20. Use according to embodiment 19, characterized in that the food product is intended for human nutrition.

21. Use according to embodiment 19, characterized in that the food product is intended to feed an animal.

22. Use according to embodiment 19, wherein the food product is a beverage.

23. Use according to embodiment 19, characterized in that said composition is used as a sugar substitute.

24. Use according to any one of embodiments 17-23, characterized in that said composition is administered in combination with at least one additional sweetener.

25. Use according to embodiment 24, characterized in that at least one additional sweetener is selected from the group consisting of extracts of stevia, arhat, acesulfame K, aspartame, cyclamate, neotame, saccharin, sucralose, thaumatin, sucrose, glucose, fructose and their mixtures.

26. A method for sweetening a comestible product, comprising adding the sweetening composition of any one of Embodiments 1-16 to the comestible product.

27. The method of embodiment 26 wherein the sweetener composition is produced in situ .

28. The method of Embodiment 27, wherein each sweetener composition component is separately added during the production of the comestible, preferably each sweetener composition component is sequentially added during the production of the comestible.

29. The method of any one of embodiments 26-28, wherein the sweetening composition is added in an amount of 1 to 5000 ppm, preferably 1 to 500 ppm, and more preferably 1 to 200 ppm, based on the total weight of the edible product.

30. The method of any one of embodiments 26-29, wherein the edible product is selected from a food product and a pharmaceutical product.

31. The method of embodiment 30, wherein the edible product is a food product.

32. The method of embodiment 31, wherein the food product is intended for human nutrition.

33. The method according to embodiment 31, characterized in that the food product is intended to feed the animal.

34. The method of embodiment 31, wherein the food product is a beverage.

35. An edible product containing the sweetener composition of any one of embodiments 1-16.

36. The edible product of embodiment 35, wherein the sweetening composition is present in an amount of 1 to 5000 ppm, preferably 1 to 500 ppm, and more preferably 1 to 200 ppm, relative to the total weight of the edible product.

37. The edible product of embodiment 35 or 36, wherein said edible product is selected from a food product and a pharmaceutical product.

38. The edible product of embodiment 37, wherein said edible product is a food product.

39. An edible product according to embodiment 38, characterized in that said food product is intended for human nutrition.

40. An edible product according to embodiment 38, characterized in that said food product is intended to feed an animal.

41. An edible product according to embodiment 38, wherein said food product is a drink.

Taste masking agent

Another aspect of the present invention is the use of a composition containing neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin as a taste masking agent.

In one embodiment of the present invention, the taste-masking composition is a mixture of NHDC and beta- or gamma-cyclodextrin, and can be obtained by simply dry mixing both components using any suitable mixing devices, for example, using a drum mixer or a paddle mixer.

In another embodiment of the present invention, the taste-masking composition is in the form of a complex.

In such a complex, the NHDC is presumably inserted, at least partially, into the cavity of the beta- or gamma-cyclodextrin to form an inclusion complex. However, the term "complex" in the meaning of the present invention includes other options, including additional non-stoichiometric interactions between NHDC and cyclodextrin to form a supramolecular complex.

Such a complex is usually prepared by dissolving the cyclodextrin in a suitable solvent, preferably water, followed by adding NHDC to the resulting solution and isolating the complex from the solution.

To obtain a complex with gamma-cyclodextrin, the concentration of gamma-cyclodextrin in solution is usually 1-20% w/v, preferably 5-10% w/v. To obtain a complex with beta-cyclodextrin, the concentration of beta-cyclodextrin in solution is usually 0.5-5% w/v, preferably 1-2% w/v.

NHDC is added to the cyclodextrin solution in an amount corresponding to the desired molar ratio of NHDC:cyclodextrin in the complex.

The resulting mixture is usually stirred until complete dissolution, typically over a period of 10 minutes to 3 hours, at a temperature typically between 20°C and 60°C.

To isolate the solid complex, the solvent is removed by any suitable means, such as freeze-drying, or it can be evaporated under reduced pressure.

As used herein, a taste-masking agent or taste-masking agent means any substance or composition that provides a taste-masking effect. A taste-masking effect, as is known in the art, means a perceptible reduction, change, or elimination of an unpleasant taste or an unpleasant taste impression from a substance.

Generally, the taste masking composition is mixed with an objectionable taste agent to produce a taste masking effect, and both substances are typically contained in the comestible product.

In a further aspect, the present invention relates to a method for masking an unpleasant taste of a substance, comprising the step of adding a composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin to the object of unpleasant taste. Typically, a composition comprising neohesperidin dihydrochalcone and cyclodextrin is added to the off-flavour in an amount effective to mask the taste.

Alternatively, the taste-masking composition can be prepared in situ so that both components, i. The NHDC and the beta- or gamma-cyclodextrin can be added separately, preferably sequentially, to the off-flavour substance or to the edible product containing the off-taste substance, usually followed by thorough mixing.

As shown in Examples 10-12, it was unexpectedly found that compositions containing a composition that contains NHDC and beta-cyclodextrin or gamma-cyclodextrin exhibit high synergy in terms of taste masking, that is, the taste masking effect achieved using the combination of the components above than the sum of the effects of each individual substance.

This synergistic effect results in significant cost savings, since it allows the use of fewer substances to mask unpleasant tastes in edible products, namely foods and pharmaceuticals.

Unpleasant tasting substances in the context of the present invention are: a) bitter, astringent, cardboardy, dusty, mealy, rancid and/or metallic tasting substances and b) substances that are bitter, astringent, cardboardy, dusty, dry, mealy , rancid or metallic aftertaste.

Among the unpleasant tastes or unpleasant taste sensations that can be masked in accordance with the practice of the present invention are, for example, bitterness, astringency and metallic tastes, preferably bitterness and/or astringency.

In one embodiment, the taste masking agent of the present invention is used to mask an unpleasant taste, which is selected from bitterness and astringency, or a combination of bitterness and astringency.

When specifically used for bitterness masking, the taste masking agent or taste masking agent may be referred to as an anti-bitter agent or a bitterness masking agent.

When specifically used for masking an astringent taste, a taste masking agent or a taste masking agent may be referred to as an anti-astringent taste masking agent or an astringent taste masking agent.

The molar ratio of NHDC:cyclodextrin in the taste-masking composition of the present invention is typically 1.5:1 to 1:6, preferably 1.2:1 to 1:4, and more preferably 1.1:1 up to 1:3.5, and even more preferably from 1:1 to 1:3.

In a preferred embodiment, the molar ratio of NHDC:cyclodextrin is about 1:1.

In another preferred embodiment, the molar ratio of NHDC:cyclodextrin is about 1:3.

In one embodiment of the present invention, the cyclodextrin is a gamma cyclodextrin.

In another embodiment of the present invention, the cyclodextrin is a beta-cyclodextrin.

Bitter taste or bitterness is presumably due to certain substances that bind to specific bitter taste receptors located on the apical membrane of taste receptor cells that are located in the taste buds of the tongue. Bitterness receptors are thought to be members of the G protein-coupled receptor (GPCR) superfamily and are referred to as T2R. These bitter receptors can interact with ligands that are chemically very diverse, so there are a large number of substances that are described as bitter, the chemical structures of which can belong to many different chemical classes.

In general, the taste of any bitter taste agent can be masked using the composition of the present invention, i.e. using a combination of NHDC and beta- or gamma-cyclodextrin.

A non-limiting list of bitter substances includes, for example, flavanones such as naringin, neohesperidin or hesperidin; flavones such as tangeritin or nobiletin; flavonols such as avicularin, quercetin, quercitrin, isoquercetin, myricetin or rutin; flavanols such as taxifolin, catechins (catechin, epicatechin, epicatechin gallate, epigallocatechin or epigallocatechin gallate) or theaflavins (theaflavin, isoteaflavin, neotheaflavin, theaflavin-3-gallate, theaflavin-3'-gallate, theaflavin-3,3'-digallate, isoteaflavin -3-gallate or theaflavic acid); isoflavones such as genistein or daidzein; chalcones such as phloridzin, triterpenes such as limonin, nomylin or limonine glucoside; hydroxycinnamic acids such as caffeic acid or its esters; olive polyphenols such as oleuropein, glucosinolates such as sinigrin, progoitrin or glucobrassicin; alkaloids such as nicotine, theobromine, theophylline, quinine or caffeine; phenolic glycosides such as salicin or arbutin; bitter alpha acids found in hop resin such as humulone, adhumulone, cohumulone, posthumulone or prehumulone; metal salts, in particular potassium, magnesium and bismuth salts such as potassium chloride, potassium gluconate, potassium carbonate, potassium succinate, potassium lactate, potassium malate; bismuth subcitrate, bismuth citrate, bismuth subgalate, bismuth salicylate, or magnesium sulfate; certain pharmaceutically active ingredients such as fluoroquinolone antibiotics, aspirin, ibuprofen, paracetamol, dextromethorphan, phenylephrine, loperamide, tramadol, ranitidine hydrochloride, acetylcysteine, glucosamine sulfate, erythromycin, levosulpiride, chlorhexidine, diosmin, β-lactam antibiotics, ambroxol or guaifenesin; unsaturated fatty acids; vitamin; bitter-tasting amino acids (eg, leucine, isoleucine, valine, tryptophan, proline, histidine, tyrosine, lysine, or phenylalanine); and certain bitter-tasting peptides, particularly those containing the hydrophobic amino acids phenylalanine, tyrosine, tryptophan, leucine, isoleucine, and valine.

Astringent taste, as defined by the American Society for Testing and Materials (ASTM, 2004), is a complex of sensations caused by pulling, pulling, or wrinkling of the epithelium as a result of exposure to substances such as alum and tannins. It is believed that astringent molecules interact with salivary proteins, in particular high proline proteins, causing them to precipitate, and the resulting loss of lubrication leads to a tactile sensation associated with an astringent taste in the mouth.

Astringent molecules are usually plant products, most commonly tannins, found in fruits and leaves or bark.

Some substances commonly perceived as astringents are, for example, tea, red wine, rhubarb and unripe persimmons and bananas.

A typical example of an astringent in the mouth is green tea, which contains certain polyphenols known as catechins, which are known to be astringents, namely catechin, epigallocatechin gallate, epigallocatechin, epicatechin gallate, epicatechin and their respective stereoisomers. Other examples of substances that cause an astringent taste are proteins such as pea protein, whey protein and soy protein.

Another example of astringent substances are the black tea theaflavins, namely theaflavin, theaflavin-3-gallate, theaflavin-3'-gallate, theaflavin-3,3'-digallate and theaflavinic acid.

The taste of some substances can be perceived as a combination of bitterness and astringency. For example, the astringent taste of green tea and black tea is sometimes perceived as a combination of bitterness/astringency.

Other substances may have a main taste or aroma that is not unpleasant, but have an additional unpleasant taste such as bitterness, astringency, or metallic notes. Without limitation, such substances may belong to the group containing aspartame, neotame, superaspartame, saccharin, sucralose, tagatose, monellin, arhat, stevia extracts, single steviol glycosides or combinations thereof, hernandulcin, thaumatin, miraculin, glycyrrhizin, glycyrrhetinic acid, and cyclamate.

In one embodiment, a composition comprising NHDC and gamma or beta cyclodextrin according to the present invention is used as an anti-bitter agent.

In another embodiment, the composition containing NHDC and gamma or beta cyclodextrin according to the present invention is used as an anti-astringent agent.

Preferably, said composition is used to mask the bitterness and/or astringent taste of a substance selected from the group consisting of: caffeine, ibuprofen, limonin, naringin, paracetamol, aspirin, potassium chloride, quercetin, quinine, theobromine, catechin, epigallocatechin gallate, epigallocatechin, epicatechin gallate , epicatechin, dextromethorphan, phenylephrine, guaifenesin, bismuth subsalicylate, soy protein, whey protein, pea protein, aspartame, sucralose, saccharin, stevia extracts and mixtures thereof.

More preferably, the proposed composition is used to mask the bitterness and/or astringent taste of a substance selected from the group consisting of caffeine, naringin, paracetamol, potassium chloride, proteins, catechins, sucralose, stevia extracts and mixtures thereof.

In a preferred embodiment, the taste masking composition is used to mask the bitterness of paracetamol. Preferably, a composition containing NHDC and gamma-cyclodextrin is used. According to this embodiment, the molar ratio of NHDC:gamma-cyclodextrin is preferably 1.5:1 to 1:10, more preferably 1.5:1 to 1:6, even more preferably 1.2: 1 to 1:4, even more preferably 1.1:1 to 1:3.5, and even more preferably 1:1 to 1:3. In a particularly preferred embodiment, said ratio is about 1:3. In another particularly preferred embodiment, said ratio is about 1:1.

In another preferred embodiment, the taste masking composition is used to mask the bitterness of quinine. Preferably, a composition containing NHDC and beta-cyclodextrin is used. According to this embodiment, the molar ratio of NHDC:beta-cyclodextrin is preferably 1.5:1 to 1:10, more preferably 1.5:1 to 1:6, even more preferably 1.2: 1 to 1:4, even more preferably 1.1:1 to 1:3.5, and even more preferably 1:1 to 1:3. In a particularly preferred embodiment, said ratio is about 1:3. In another particularly preferred embodiment, said ratio is about 1:1.

In another preferred embodiment, the taste masking composition is used to mask the astringent taste of green tea. According to this embodiment, the inventive composition has an astringent taste masking effect against astringent green tea components, typically the catechins: epigallocatechin gallate, epigallocatechin, epicatechin gallate and/or epicatechin.

According to this embodiment, the molar ratio of NHDC:cyclodextrin is preferably 1.5:1 to 1:10, more preferably 1.5:1 to 1:6, even more preferably 1.2:1 to 1:4, even more preferably 1.1:1 to 1:3.5, and even more preferably 1:1 to 1:3. In a particularly preferred embodiment, said ratio is about 1:3. In another particularly preferred embodiment, said ratio is about 1:1.

The taste-masking agent of the present invention is typically added to an edible product that contains an objectionable taste, typically containing a bitter and/or astringent taste.

Another aspect of the present invention is a method of masking an unpleasant taste of a edible product that contains at least one objectionable substance, comprising adding to the edible product a taste masking composition containing neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin.

The step of adding the taste-masking composition to the edible product includes adding the premixed composition to the edible product as well as introducing both components, i.e. NHDC and beta and/or gamma cyclodextrin, individually, preferably sequentially.

Another aspect of the present invention is an edible product which contains at least one objectionable substance and a taste masking composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin. Preferably, the off-tasting substance is a bitter or astringent.

The amount of the off-tasting substance contained in the edible product is sufficient for the perception of an unpleasant taste if the edible product does not contain a taste-masking agent.

In one embodiment, the amount of the off-tasting substance in the comestible is 1-5000 ppm based on the total weight of the comestible without the taste masking agent.

The taste masking agent is added to the edible product in an amount effective to mask the taste. As used herein, a "taste-masking effective amount" is an amount of a taste-masking composition that is sufficient to reduce, modify, or eliminate the objectionable taste of an objectionable tastant compared to an edible product without a taste-masking agent. The amount effective for masking taste can vary widely depending on the particular objectionable substance, on its relative content in the comestible, and on the particular comestible.

Those skilled in the art can readily select the appropriate amount of the taste-masking agent in each particular case.

In one embodiment, the taste masking composition is added in an amount of 1-2000 ppm, preferably 1-1000 ppm, and more preferably 1-500 ppm, based on the total weight of the comestible. The total weight of the comestible product also includes the weight of the sweetener composition added.

The term "edible product" as used herein broadly refers to any substance suitable for oral ingestion by a human or animal, and includes substances that are drunk, eaten, ingested or otherwise consumed, namely foods and pharmaceuticals. In addition, the term "edible product" also includes substances that are not intended to be swallowed, but which are initially placed in the mouth and then spit out, such as chewing gums and oral care compositions, such as, for example, mouthwashes. , toothpastes or tooth gels.

In one embodiment of the present invention, the comestible product is selected from the group consisting of foods, pharmaceuticals, and oral care compositions; preferably selected from foods and pharmaceuticals.

In another embodiment of the present invention, the edible product is a food product.

In another embodiment of the present invention, the comestible product is a pharmaceutical product.

The expression "food" in this context means any edible product intended for human or animal nutrition, and includes solid, semi-solid and liquid products, including also beverages. The expression "food product" also includes products that are intended only for partial consumption and subsequent spitting out of the mouth, in particular chewing gum.

Beverages suitable for adding a taste-masking agent according to the present invention may be, without limitation, any kind of beverage containing an objectionable tastant, preferably containing a bitter and/or astringent tasting agent, and may be carbonated or still. , alcoholic or non-alcoholic, and includes, among others, fruit-flavored soft drinks, sodas, cola, sports drinks, and, in general, any beverage containing and/or flavored with, for example, fruits, vegetables, aromatic plants, tea, coffee or cocoa; they also include drinks containing, for example, wine or beer; they also include energy or health drinks containing, for example, protein hydrolysates, vitamins and/or phytonutrients having a bitter and/or astringent taste.

The beverage category includes ready-to-drink beverages as well as other forms such as powders, granules, tablets or liquid concentrates that are intended to be diluted with water.

Other food products suitable for the addition of a taste-masking agent according to the present invention are, for example, baked goods such as bread, pies, biscuits, muffins and, in general, any kind of baked goods; also dairy products such as yogurt, drinking yogurt, frozen yogurt, milk, milk drinks, condensed milk, cream, cheese or ice cream; soy products such as soybean oil or soy lecithin; confectionery products such as chocolate, caramel, candies, marzipan or chewing gums; cereal products such as breakfast cereals, cereal sticks, energy/nutrition bars or cereals; fruit products such as jams, fruit purees, canned fruits and sauces; vegetable products such as sauces, dried vegetables, canned vegetables, or frozen vegetables; oil-based products and emulsions such as mayonnaise and some dressings; and many others, provided that they contain an unpleasant tasting substance, preferably a bitter and/or astringent tasting substance.

The food category also includes, in particular, nutritional or dietary supplements, i. foods enriched with certain nutritional ingredients, such as vitamins, minerals, amino acids, proteins, botanicals, enzymes, or other substances intended to supplement the human diet, and which may be in any suitable food product form, such as beverages or, for example, bars.

Also included in the expression "food product" are any types of dried products, such as dessert mixes or dried products ready to eat.

Food products also include, in particular, any food intended for animal nutrition.

Pharmaceutical products suitable for adding the taste masking agent according to the present invention are pharmaceutical products containing an unpleasant tasting active ingredient, namely a bitter or astringent tasting ingredient, including also any kind of food additives with an unpleasant taste, for example, vitamins, minerals and mixtures thereof. Preferably, the bitter or astringent active ingredient is selected from fluoroquinolone antibiotics, ibuprofen, paracetamol, β-lactam antibiotics, ambroxol, guaifenesin and mixtures thereof; preferably, the active ingredient is paracetamol.

The pharmaceutical products may be in any form suitable for oral administration to humans or veterinary therapy. The pharmaceutical products may be in any form suitable for oral administration well known to those skilled in the art, e.g., solid forms such as tablets, chewable tablets, disintegrating tablets in the mouth (ODT), sublingual tablets, disintegrating films in the mouth ( flash films), lozenges, chewing gums or powders; or liquid forms such as drops, syrups and suspensions; or alternatively in the form of powders, granules or tablets intended to be dissolved in a liquid for administration, for example in the form of effervescent tablets.

The taste-masking composition of the present invention may be added to the edible product in a conventional manner known to those skilled in the art of pharmaceutical or food technology, for example, may be added to a pharmaceutical product along with other formulation excipients, or to a food product at an appropriate stage in the process.

It should be understood that the above examples are non-limiting, and any edible product containing an unpleasant tastant, preferably a bitter and/or astringent tastant, may be suitable for the addition of a taste masking composition of the present invention.

Another aspect of the present invention relates to a taste masking composition comprising neohesperidin dihydrochalcone and gamma-cyclodextrin.

In one embodiment, the proposed taste-masking composition is a mixture of both components.

In another embodiment, the NHDC and gamma-cyclodextrin are in the form of a complex.

The molar ratio of NHDC:gamma-cyclodextrin according to this aspect of the invention is usually from 1.5:1 to 1:10, preferably from 1.5:1 to 1:6, more preferably from 1.2:1 to 1:4, still more preferably 1.1:1 to 1:3.5 and even more preferably 1:1 to 1:3.

In a preferred embodiment of this aspect of the invention, the molar ratio of NHDC:gamma-cyclodextrin is about 1:1.

In another preferred embodiment, the molar ratio of NHDC:gamma-cyclodextrin is about 1:3.

Aspects of the present invention that relate to a taste masking composition comprising NHDC and gamma-cyclodextrin or beta-cyclodextrin can be defined according to the following embodiments:

1. Use of a composition containing neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin as a taste masking agent.

2. Use according to embodiment 1, characterized in that said composition is a mixture of neohesperidin dihydrochalcone and cyclodextrin.

3. Use according to embodiment 1, characterized in that neohesperidin dihydrochalcone and cyclodextrin are in the form of a complex.

4. Use according to any one of embodiments 1-3, characterized in that the molar ratio of neohesperidin dihydrochalcone:cyclodextrin is from 1.5:1 to 1:10.

5. Use according to any one of embodiments 1-4, characterized in that the molar ratio of neohesperidin dihydrochalcone:cyclodextrin is from 1.5:1 to 1:6.

6. Use according to embodiment 5, characterized in that the molar ratio of neohesperidin dihydrochalcone:cyclodextrin is from 1.2:1 to 1:4.

7. Use according to embodiment 6, characterized in that the molar ratio of neohesperidin dihydrochalcone:cyclodextrin is from 1.1:1 to 1:3.5.

8. Use according to embodiment 7, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1:1 to 1:3.

9. Use according to any one of embodiments 1-8, characterized in that the molar ratio of neohesperidin dihydrochalcone:cyclodextrin is 1:1.

10. Use according to any one of embodiments 1-8, characterized in that the molar ratio of neohesperidin dihydrochalcone:cyclodextrin is about 1:1.

11. Use according to any one of embodiments 1-8, characterized in that the molar ratio of neohesperidin dihydrochalcone:cyclodextrin is 1 ± 0.1: 1 ± 0.1.

12. Use according to embodiment 11, characterized in that the molar ratio of neohesperidin dihydrochalcone:cyclodextrin is 1 ± 0.05: 1 ± 0.05.

13. Use according to any one of embodiments 1-8, characterized in that the molar ratio of neohesperidin dihydrochalcone:cyclodextrin is 1:3.

14. Use according to any one of embodiments 1-8, characterized in that the molar ratio of neohesperidin dihydrochalcone:cyclodextrin is about 1:3.

15. Use according to any one of embodiments 1-8, characterized in that the molar ratio of neohesperidin dihydrochalcone: cyclodextrin is 1 ± 0.1 : 3 ± 0.3.

16. Use according to embodiment 15, characterized in that the molar ratio of neohesperidin dihydrochalcone: cyclodextrin is 1 ± 0.05 : 3 ± 0.15.

17. Use according to any one of embodiments 1-16, wherein the cyclodextrin is beta-cyclodextrin.

18. Use according to any one of embodiments 1-16, wherein the cyclodextrin is a gamma cyclodextrin.

19. Use according to any one of embodiments 1-18 to mask bitterness.

20. Use according to any one of embodiments 1-19 to mask astringent taste.

21. Use according to any one of embodiments 1-20 to mask metallic notes.

22. Use according to any one of embodiments 1-21 to mask bitterness and/or astringency and/or metallic notes.

23. Use according to any one of embodiments 1-20 to mask bitterness and/or astringent taste of a substance selected from the group consisting of: caffeine, ibuprofen, limonin, naringin, paracetamol, aspirin, potassium chloride, quercetin, quinine, theobromine, catechin , epigallocatechin gallate, epigallocatechin, epicatechin gallate, epicatechin, dextromethorphan, phenylephrine, guaifenesin, bismuth subsalicylate, soy protein, whey protein, pea protein, aspartame, sucralose, saccharin, stevia extracts and mixtures thereof.

24. Use according to embodiment 23, characterized in that said substance is selected from the group consisting of: caffeine, naringin, paracetamol, potassium chloride, proteins, catechins, sucralose, stevia extracts and mixtures thereof.

25. Use according to any one of embodiments 1-18, characterized in that it is intended to mask the bitter taste of paracetamol.

26. Use according to any one of embodiments 1-18, characterized in that it is intended to mask the bitter taste of quinine.

27. Use according to any one of embodiments 1-18, characterized in that it is intended to mask the astringent taste of green tea.

28. A method for masking an unpleasant taste of an edible product that contains at least one substance with an unpleasant taste, including adding to the edible product a taste masking composition containing neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin.

29. The method of embodiment 28, wherein the taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1.5:1 to 1:10.

30. The method of embodiment 28 or 29, wherein the taste masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1.5:1 to 1:6.

31. The method of Embodiment 30, wherein the taste masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1.2:1 to 1:4.

32. The method of Embodiment 31 wherein the taste masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1.1:1 to 1:3.5.

33. The method of embodiment 32, wherein the taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1:1 to 1:3.

34. The method of any one of embodiments 28-33, wherein said taste-masking composition has a molar ratio of neohesperidin dihydrochalcone:cyclodextrin of 1:1.

35. The method of any one of embodiments 28-33, wherein said taste masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of about 1:1.

36. The method of any one of embodiments 28-33, wherein said taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1±0.1:1±0.1.

37. The method of Embodiment 36 wherein the taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1±0.05:1±0.05.

38. The method of any one of embodiments 28-33, wherein said taste masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1:3.

39. The method of any one of embodiments 28-33, wherein said taste masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of about 1:3.

40. The method of any one of embodiments 28-33, wherein said taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1±0.1:3±0.3.

41. The method of Embodiment 40, wherein the taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1±0.05:3±0.15.

42. The method of any one of embodiments 28-41, wherein the off-flavour is bitter and/or astringent.

43. The method according to any one of embodiments 28-42, wherein the objectionable taste is selected from the group consisting of: caffeine, ibuprofen, limonin, naringin, paracetamol, aspirin, potassium chloride, quercetin, quinine, theobromine, catechin, epigallocatechin gallate, epigallocatechin, epicatechin gallate, epicatechin, dextromethorphan, phenylephrine, guaifenesin, bismuth subsalicylate, soy protein, whey protein, pea protein, aspartame, sucralose, saccharin, stevia extracts and mixtures thereof.

44. The method of embodiment 43, wherein the off-tasting substance is selected from the group consisting of: caffeine, naringin, paracetamol, potassium chloride, proteins, catechins, sucralose, stevia extracts, and mixtures thereof.

45. The method of any one of embodiments 28-44, wherein the edible product is selected from a food product and a pharmaceutical product.

46. The method of embodiment 45, wherein the edible product is a pharmaceutical product containing a bitter active ingredient selected from paracetamol, ibuprofen, aspirin, dextromethorphan, phenylephrine, guaifenesin, and bismuth subsalicylate.

47. The method of embodiment 45, wherein the edible product is a food product that contains a bitter or astringent selected from caffeine, limonine, naringin, potassium chloride, quercetin, quinine, catechins, soy protein, whey protein, pea protein, aspartame, sucralose, saccharin and stevia extracts.

48. An edible product that contains at least one objectionable substance and a taste masking composition, said taste masking composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin.

49. The edible product of embodiment 48, wherein the objectionable substance is bitter or astringent.

50. Edible product according to embodiment 48 or 49, characterized in that the objectionable substance is selected from the group consisting of: caffeine, ibuprofen, limonin, naringin, paracetamol, aspirin, potassium chloride, quercetin, quinine, theobromine, catechin, epigallocatechin gallate , epigallocatechin, epicatechin gallate, epicatechin, dextromethorphan, phenylephrine, guaifenesin, bismuth subsalicylate, soy protein, whey protein, pea protein, aspartame, sucralose, saccharin, stevia extracts and mixtures thereof.

51. Edible product according to any one of embodiments 48-50, characterized in that the objectionable substance is selected from the group consisting of: caffeine, naringin, paracetamol, potassium chloride, proteins, catechins, sucralose, stevia extracts, and mixtures thereof.

52. An edible product according to any one of embodiments 48-51, wherein said edible product is selected from a food product and a pharmaceutical product.

53. The edible product according to embodiment 52, characterized in that it is a pharmaceutical product containing an unpleasant tastant, which is a bitter active ingredient selected from paracetamol, ibuprofen, aspirin, dextromethorphan, phenylephrine, guaifenesin, and bismuth subsalicylate.

54. The edible product according to embodiment 52, wherein said edible product is a food product containing an unpleasant tasting substance, which is a bitter or astringent selected from caffeine, limonine, naringin, potassium chloride, quercetin, quinine, catechins, soy protein, whey protein, pea protein, aspartame, sucralose, saccharin and stevia extracts.

55. An edible product according to any one of embodiments 48-54, wherein said taste masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1.5:1 to 1:10.

56. An edible product according to any one of embodiments 48-55, wherein said taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1.5:1 to 1:16

57. The edible product of Embodiment 56, wherein the taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1.2:1 to 1:4.

58. The edible product of Embodiment 57, wherein the taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1.1:1 to 1:3.5.

59. The edible product of Embodiment 58, wherein the taste masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1:1 to 1:3.

60. An edible product according to any one of embodiments 48-59, wherein said taste-masking composition has a molar ratio of neohesperidin dihydrochalcone:cyclodextrin of 1:1.

61. An edible product according to any one of embodiments 48-59, wherein said taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of about 1:1.

62. An edible product according to any one of embodiments 48-59, wherein said taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1±0.1:1±0.1.

63. The edible product of embodiment 62, wherein the taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1 ± 0.05: 1 ± 0.05.

64. An edible product according to any one of embodiments 48-59, wherein said taste masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1:3.

65. An edible product according to any one of embodiments 48-59, wherein said taste masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of about 1:3.

66. An edible product according to any one of embodiments 48-59, wherein said taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1±0.1:3±0.3.

67. An edible product according to embodiment 66, wherein the taste-masking composition has a neohesperidin dihydrochalcone:cyclodextrin molar ratio of 1±0.05:3±0.15.

68. An edible product according to any one of embodiments 48-67, wherein the cyclodextrin is beta-cyclodextrin.

69. An edible product according to any one of embodiments 48-67, wherein the cyclodextrin is a gamma cyclodextrin.

70. A taste masking composition containing neohesperidin dihydrchalcone and gamma-cyclodextrin.

71. A taste masking composition according to embodiment 70, characterized in that it is a mixture of neohesperidin dihydrochalcone and gamma-cyclodextrin.

72. The taste masking composition of Embodiment 70, wherein neohesperidin dihydrochalcone and gamma-cyclodextrin are in the form of a complex.

73. A taste masking composition according to any one of embodiments 70-72, wherein the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1.5:1 to 1:10.

74. A taste masking composition according to any one of embodiments 70-73, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1.5:1 to 1:6.

75. The taste masking composition of Embodiment 74, wherein the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1.2:1 to 1:4.

76. The taste masking composition of Embodiment 75, wherein the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1.1:1 to 1:3.5.

77. A taste masking composition according to any one of embodiments 70-76, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1:1 to 1:3.

78. The taste masking composition of any one of embodiments 70-77, wherein the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is 1:1.

79. The taste masking composition of any one of embodiments 70-77, wherein the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is about 1:1.

80. A taste masking composition according to any one of embodiments 70-77, characterized in that the molar ratio of neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.1 : 3 ± 0.3.

81. The taste-masking composition of embodiment 80, wherein the molar ratio of neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.05: 3 ± 0.15.

82. The taste masking composition of any one of embodiments 70-77, wherein the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is 1:3.

83. The taste masking composition of any one of embodiments 70-77, wherein the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is about 1:3.

84. A taste masking composition according to any one of embodiments 70-77, characterized in that the molar ratio of neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.1 : 3 ± 0.3.

85. A taste masking composition according to embodiment 84, characterized in that the molar ratio of neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.05: 3 ± 0.15.

The following examples further illustrate the present invention.

EXAMPLES

Example 1 Sweetener Compositions

Several sweetener compositions of the present invention were prepared using various molar ratios between neohesperidin dihydrochalcone (NHDC) and gamma cyclodextrin (gCD) as shown in Table 1. NHDC was purchased from Ferrer HealthTech and gamma cyclodextrin was purchased from Wacker.

From the molar masses of NHDC (613) and gamma-cyclodextrin (1297), the weight percentage of NHDC contained in each composition was calculated.

TABLE 1

sweetening agent NHDC:gCD ratio NHDC, % wt. Example A 1:1 32.10 Example B 1:3 13.61 Example C 1.5:1 41.48 Example D 1:6 7.30 Example E 1:10 4.51

The sweetening compositions used were presented in the form of a complex.

To prepare the complex of example A, NHDC (14.0 g, 20.6 mmol) was added to a stirred solution of gCD (30 g, 20.6 mmol) in deionized water (500 ml). The mixture was stirred for one hour at 20-25°C until complete dissolution. The solution was clarified through a filter with a pore size of 0.8 μm to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (40 g) of the 1:1 complex was obtained.

To prepare the complex of example B, NHDC (7.5 g, 11 mmol) was added to a stirred solution of gCD (47.7 g, 33 mmol) in deionized water (500 ml). The mixture was stirred for one hour at 20-25°C until complete dissolution. The solution was clarified through a filter with a pore size of 0.8 μm to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (54 g) of the 1:3 complex was obtained.

Examples C-E complexes were prepared under the same conditions as described above for examples A and B.

Example 2 Comparative Sweetening Compositions

For comparison, sweetener compositions were prepared that were equal in sweetness to Examples A and B, but using beta-cyclodextrin instead of gamma-cyclodextrin, also in complex form. Thus, Comparative Examples A and B were prepared using the molar ratios between NHDC and beta-cyclodextrin (bCD) shown in Table 2. Beta-cyclodextrin was purchased from Wacker.

Similarly to example 1, using the molar masses of NHDC (613) and beta-cyclodextrin (1138) calculated the mass percentage of NHDC contained in each composition.

TABLE 2

sweetening agent NHDC:bCD ratio NHDC, % wt. Comparative example A 1:1 35.07 Comparative example B 1:3 15.26

To obtain the complex of comparative example A was added NHDC (7.0 g, 10.2 mmol) to a stirred solution of bCD (13.4 g, 10.2 mmol) in deionized water (900 ml) at 50°C. The mixture was stirred for two hours at 50°C until complete dissolution. The solution was clarified through a filter with a pore size of 0.8 μm to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (18.1 g) of the 1:1 complex was obtained.

To obtain the complex of comparative example B, NHDC (4.0 g, 5.8 mmol) was added to a stirred solution of bCD (22.9 g, 17.5 mmol) in deionized water (1500 ml) at 50°C. The mixture was stirred for two hours at 50°C until complete dissolution. The solution was clarified through a filter with a pore size of 0.8 μm to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (23.9 g) of the 1:3 complex was obtained.

Example 3 Sweetening Synergy Tests

A sensory test was conducted to evaluate the sweetening synergy achieved with the composition of the present invention (Examples A and B) and also compared the effect obtained with the effect achieved with similar compositions containing beta-cyclodextrin (Comparative Examples A and B). Other compositions according to the present invention were also evaluated in this sensory test (examples C, D and E).

A group of tasters in the field of sweet taste description tested the sweet taste of various compositions, as well as the ingredients - NHDC, beta-cyclodextrin and gamma-cyclodextrin, used separately.

Each tested sweetener was dissolved in water at various concentrations at room temperature. Then a group of tasters determined the concentration of each product, equal in sweetness to the reference solutions of 1% and 3% sucrose in water. The results are summarized in Table 3 (Examples A and B are abbreviated as Ex A and Ex B, respectively, and comparative examples A and B are abbreviated as Comp. A and Comp. B, respectively).

TABLE 3

sweetening agent NHDC Etc. A NHDC:gCD 1:1 Etc. B NHDC:gCD 1:3 Etc. C NHDC:gCD 1.5:1 Etc. D NHDC:gCD 1:6 Etc. E NHDC:gCD 1:10 Wed A NHDC:bCD 1:1 Wed B NHDC:bCD 1:3 1% sucrose (actual sweetness) Sweetness Equivalent Concentration (ppm) 5.0 12.0 26.0 9.0 50.0 85.0 17.0 50.0 NHDC content (ppm) (5.0) (3.9) (3.5) (3.6) (3.9) (3.7) (6.1) (7.7) 3% sucrose (actual sweetness) Sweetness Equivalent Concentration (ppm) 24.0 42.0 90.0 32.0 180.0 300.0 82.0 185.0 NHDC content (ppm) (24.0) (13.5) (12.2) (12.7) (13.0) (13.0) (28.8) (28.3)

Since beta- and gamma-cyclodextrins are also sweet compounds, the panel of tasters also determined equal sweetness concentrations of both cyclodextrins to evaluate their possible contribution to the overall sweet taste of the composition. It was found that the concentration of beta-cyclodextrin, equal in sweetness to 1% and 3% sucrose, was 12,000 and 70,000 ppm, respectively, and equal in sweetness to the concentration of gamma-cyclodextrin were 25,000 and 85,000 ppm. Thus, since the equal sweetness concentrations of both cyclodextrins at least three orders of magnitude higher than similar NHDC concentrations, it was concluded that their contribution to the sweet taste is negligible.

The first row of data for each sucrose concentration in Table 3 shows the equal sweetness concentrations (in ppm) of each tested agent, and the second row shows the calculated amount of pure NHDC (in ppm) contained in such equal sweetness concentrations. The results obtained are graphically presented in Fig. 1 and 2.

A more accurate quantification of the sweetness synergy provided by the compositions of the present invention was made by comparing the actually measured sweetness of the compositions containing gamma-cyclodextrin and NHDC with the theoretical sweetness expected from the sum of the individual contributions of each component of the composition.

To do this, the relative sweetening efficiency of each component was first calculated. For comparison, the relative sweetening potency of beta-cyclodextrin was also calculated. The relative sweetening potency of a given compound for a given level of sweetness refers to how many times that compound is sweeter than sucrose. Thus, it is calculated as the ratio between the sucrose concentration and the equal sweetness concentration of each ingredient for each level of sweetness. The relative sweetening potencies of NHDC, beta-cyclodextrin (bDC), and gamma-cyclodextrin (gCD) are shown in Table 4.

TABLE 4

1% sucrose (actual sweetness) Individual Ingredients NHDC bCD gCD Sweetness Equivalent Concentration (ppm) 5 12000 25000 Relative sweetening efficiency 2000 0.8333 0.4000 3% sucrose (actual sweetness) Individual Ingredients NHDC bCD gCD Sweetness Equivalent Concentration (ppm) 24 70000 85000 Relative sweetening efficiency 1250 0.4286 0.3529

Based on the relative sweetening potency of each ingredient, the expected sweetness (sucrose equivalent) of a mixture of said ingredients can be calculated according to Formula I :

Expected sweetness (sucrose equivalent) of mixture C1 + C2 =

Compound C1 concentration x relative sweetening potency of C1+ compound

Concentration of Compound C2 x Relative Sweetening Potency of Compound C2

The sweetening synergy of the mixture of components can then be calculated using Formula II :

Sweetening Synergy = Actual sweetness - expected sweetness Expected sweetness

Tables 5 and 6 below show the expected (theoretical) sweetness and sweetening synergy for compositions according to the present invention (examples A and B) and, for comparison purposes, also for comparative examples A and B containing a combination of NHDC and beta-cyclodextrin , for a sucrose concentration of 1% (table 5) and a sucrose concentration of 3% (table 6).

TABLE 5

1% sucrose (actual sweetness) Etc. A NHDC:gCD 1:1 Etc. B NHDC:gCD 1:3 Wed A NHDC:bCD 1:1 Wed B NHDC:bCD 1:3 Etc. C NHDC:gCD 1.5:1 Etc. D NHDC:gCD 1:6 Etc. E NHDC:gCD 1:10 Sweetness Equivalent Concentration (ppm) 12.00 26.00 17.50 50.00 9.00 50.00 85.00 NHDC content (ppm) 3.85 3.54 6.14 7.65 3.56 3.62 3.69 Content of gCD/bCD (ppm) 8.12 22.46 11.36 42.35 5.44 46.38 81.31 Expected sweetness (%) 0.77 0.72 1.24 1.57 0.81 0.82 0.84 Sweetening synergy (%) 29.9 38.9 -19.4 -36.3 23.4 21.2 18.6

TABLE 6

3% sucrose (actual sweetness) Etc. A NHDC:gCD 1:1 Etc. B NHDC:gCD 1:3 Wed A NHDC:bCD 1:1 Wed B NHPD:bCD 1:3 Etc. C NHDC:gCD 1.5:1 Etc. D NHDC:gCD 1:6 Etc. E NHDC:gCD 1:10 Sweetness Equivalent Concentration (ppm) 42.00 90.00 82.00 185.00 32.00 180.00 300.00 NHDC content (ppm) 13.48 12.24 28.78 28.31 12.67 13.02 13.03 Content of gCD/bCD (ppm) 28.52 77.76 53.22 156.69 17.64 158.34 264.17 Expected sweetness (%) 1.70 1.56 3.62 3.61 1.80 1.86 1.86 Sweetening synergy (%) 76.5 92.3 -17.1 -16.9 66.6 61.5 61.1

For example, for a sucrose content of 1% (table 5), the expected sweetness of 12 ppm of the composition of example A (first column) was calculated from formula I as follows: 3.85 10 ^-4 x 2000 + 8.12 10 ^-4 x 0.4, t .e. equivalent to 0.77% sucrose. Since the actual sweetness is equivalent to 1% sucrose, the synergy can be calculated according to formula II as follows: 1-0.77/0.77, i.e. synergy is 29.9%.

Similarly, for a sucrose content of 3% (Table 6), the expected ^sweetness of the ⁴² ppm composition of Example A (first column) was calculated from Formula I as follows: .e. equivalent to 1.70% sucrose. The synergy can then be calculated from Formula II as follows: (3-1.70)/1.70, i.e. synergy is 76.5%.

All expected sweetness and sweetening synergy values in Tables 5 and 6 were calculated in a similar manner using the respective relative sweetening potency values (from Table 4) and the respective actual sweetness values (1% or 3%).

Example 4 Enhancement of Sweetening Efficiency with Increase in Sweetness Level

As described in Example 3 above, the relative sweetening potency of a given compound at a given level of sweetness means how many times a given compound is sweeter than sucrose, and this value is calculated as the ratio between the concentration of sucrose and an equal sweetness concentration of the given compound.

The relative sweetening potency of NHDC at 1% and 3% sucrose was calculated in Example 3 and presented in Table 4.

The sweetening potency of the compositions of the present invention with respect to sucrose can be calculated similarly for a given sucrose content. So, for example, since 12 and 42 ppm compositions of example A are equal in sweetness to 1% and 3% sucrose solutions, respectively (see table 3), then the composition of example A is 833 and 714 times sweeter than sucrose at a sucrose content of 1% and 3% , respectively.

Similarly, since the 26 and 90 ppm compositions of Example B are equal in sweetness to 1% and 3% sucrose solutions, respectively (see Table 3), the composition of Example B is 385 and 333 times sweeter than sucrose at 1% and 3% sucrose, respectively. .

The relative sweetening potency values of each substance, as well as those of the compositions of Examples A-D, are summarized in Table 7 below.

TABLE 7

Relative sweetening efficiency Sucrose content NHDC Etc. A NHDC:gCD 1:1 Etc. B NHDC:gCD 1:3 Etc. C NHDC:gCD 1.5:1 Etc. D NHDC:gCD 1:6 one% 2000 833 385 1111 200 3% 1250 714 333 937 167

The results of Table 7 are shown in the diagram in FIG. 3.

Example 5: Taste Profile

The overall flavor profile achieved with the sweetener composition of the present invention was evaluated and compared to the desired flavor profile of sucrose.

For this analysis, all samples were evaluated at the same degree of sweetness, so that each sample was used at a concentration equal in sweetness to 3% sucrose. The following parameters were evaluated for each sample:

- Time to first perception of sweetness

- Time to maximum sweetness

- Duration of action (time until sweetness disappears)

- Taste: menthol, licorice (any flavor other than sweet)

- Mouthfeel (thickness, i.e. perceptible viscosity in the mouth).

The tests were carried out by a certified tasting committee, and the tests were carried out at room temperature.

Each of these parameters was evaluated on a scale from 0 to 5. The values for sucrose were reference values and were considered as the target value for simulation.

The results obtained in this test are summarized in the following table:

TABLE 8

Perceptual characteristics Sucrose (3%) NHDC (24ppm) Etc. A (42ppm) Etc. B (90ppm) General sweetness 5.00 5.00 5.00 5.00 Time to first perception of sweetness 1.00 3.75 3.25 3.00 Time to maximum sweetness 2.00 4.25 3.25 2.75 Duration of action 2.00 4.00 3.50 2.75 Taste: menthol, licorice 0.00 3.25 2.50 2.00 Mouthfeel (density) 4.00 1.75 2.50 3.00

The results presented in Table 8 are graphically depicted in FIG. 4 in the form of a web diagram.

Example 6 Sweetened Beverage

A reference orange soft drink sweetened with high fructose corn syrup (HFCS) was prepared using the ingredients listed in Table 9 (Formulation 1). All percentages in the table are expressed by weight.

TABLE 9

Ingredient Recipe 1 (Standard) Recipe 2 Recipe 3 HFCS-42* (71°Bx) (sugar reduction) 15.27% (0%) 13.75% (10%) 13.75% (10%) NHDC - 10ppm - Example B (NHDC:bCD 1:3) (NHDC content) - - 33ppm (4.5ppm) sodium benzoate 0.02% 0.02% 0.02% Potassium sorbate 0.02% 0.02% 0.02% Lemon acid 0.34% 0.34% 0.34% Coloring for orange soda water 0.05% 0.05% 0.05% Orange Soda Flavor 0.22% 0.22% 0.22% Water 84.08% 85.61% 85.61% Total 100.00% 100.00% 100.00%

* HFCS-42 = HFCS with 42% fructose.

Drinks were obtained in the following way. High fructose corn syrup was weighed into a 1 L beaker. The remaining minor ingredients (sodium benzoate, potassium sorbate, citric acid, orange soda color and orange soda flavor) were individually weighed into small beakers and water was added to each small beaker and mixed until each ingredient was solubilized. After dissolution, all minor ingredients were added to a 1 L HFCS beaker. The resulting solution was thoroughly mixed and water was gradually added up to 1 kg.

To analyze the possible replacement of HFCD with NHDC and with the composition according to the present invention (example B), a 0.1% stock solution of NHDC in water was prepared by gradually adding 0.1 g of NHDC to 99.9 g of water, stirring and heating to 66°C. within 15 minutes to obtain a yellowish solution; the solution was then allowed to cool to room temperature. Similarly, a 1% stock solution of Example B in water was prepared by adding 1 g of Example B to 99 g of water and stirring to give a yellowish solution.

The maximum sugar substitution for NHDC was then determined, replacing increasing amounts of HFCS with NHDC, and then the tasting panel checked the reference sample and the experimental sample using a sensory evaluation using the triangle method. Thus, the criterion for determining the maximum degree of sugar replacement is not only an equal degree of sweetness between the reference sample and the experimental sample, but also the overall flavor profile.

The maximum sugar replacement achieved with NHDC without any noticeable difference in the triangle sensory score was 10% (Formulation 2 in Table 9). This displacement was achieved using 10 ppm NHDC.

In the second step, the tasters determined the amount of Example B (composition containing a 1:3 molar ratio of NHDC:bCD) needed to achieve the same sugar replacement. The same 10% sugar replacement was achieved using the 33 ppm formulation of Example B which contained 4.5 ppm NHDC (Formulation 3 in Table 9).

Example 7 Sweetened Beverage

The objective of this example was to maximize sugar replacement in an orange juice soft drink while maintaining the same overall flavor profile. The tasting panel could not distinguish the reference from the various experimental samples in the test using the organoleptic evaluation using the triangle method.

The reference product (Formulation 1 in Table 10) contained 10% added sucrose. The maximum sucrose replacement achieved with NHDC was 15% compared to the original 10% using 10 ppm NHDC (Formulation 2 in Table 10). Using the sweetener composition of the present invention, it is possible to increase the degree of sucrose substitution up to 25% without changing the flavor profile of the beverage (Formulation 3 in Table 10).

The composition of each drink is described in Table 10. Orange juice concentrate at 65°Bx (Dallant) and orange flavor No. 2N341/C (Dallant) were used to prepare these drinks. All percentages in the table are expressed by weight.

TABLE 10

Ingredient Recipe 1 (Standard) Recipe 2 Recipe 3 Sucrose (sugar reduction) 10,000% (0%) 8.500% (15%) 7.500% (25%) NHDC - 8.0ppm - Example B (NHDC:bCD 1:3) (NHDC content) - - 80.0ppm (10.9ppm) Orange juice concentrate (65°Bx) 1.850% 1.850% 1.850% sodium benzoate 0.015% 0.015% 0.015% Lemon acid 0.225% 0.225% 0.225% orange flavor 0.100% 0.100% 0.100% orange dye 0.100% 0.100% 0.100% Water 87.710% 89.210% 90.210% Total 100.00% 100.00% 100.00%

Example 8: Sweetened Dark Chocolate

Received various formulations of sweetened dark chocolate, using the ingredients listed in table 11. Percentages in the table are expressed by weight.

TABLE 11

Ingredient Recipe 1 (Standard) Recipe 2 Recipe 3 Recipe 4 Powdered sugar (sugar reduction) 6.00% 5.40% (10.00%) 4.91% (18.17%) 4.32% (28.00%) 1% NHDC solution in glycerol (NHDC content) - 0.03% (3ppm) - - Composition of example B (NHDC:bCD 1:3)
(NHDC content) - - 0.0022% (3ppm) 0.004% (5.45ppm) Chocolate with 70% cocoa content up to 100% up to 100% up to 100% up to 100% Total 100.00% 100.00% 100.00% 100.00%

The reference product (Formulation 1 in Table 11) contained a commercially available chocolate containing 70% cocoa ( ^Lindt® ) and 6% powdered sugar.

In addition to all analyzes, the goal was to maximize the degree of sucrose substitution while maintaining the same overall flavor profile. The tasting committee could not distinguish the standard from the various experimental samples tested.

The first trial evaluated the maximum substitution of sucrose for pure NHDC. In this case, NHDC was added in the form of a 1% solution in glycerol, and the maximum sugar replacement in this case was 10% sucrose (compared to the original 6% in the formulation). This reduction was achieved using a 0.03% glycerol solution, equivalent to 3 ppm NHDC (Formulation 2 in Table 11).

Using the same amount of pure NHDC, i.e. 3 ppm, but contained in the composition of example B (equivalent to 22 ppm of example B), it was found that it is possible to replace a higher percentage of sugar in the reference product, up to 18.17% sugar (formulation 3 in table 11).

In the following assay, the maximum sugar replacement was determined by the composition of example B. Using this composition, it is possible to reduce the sugar content of the reference product by up to 28% without changing the taste profile of the product, using 40 ppm of example B (containing 5.45 ppm NHDC) (formulation 4 in table 11).

Used the following method to obtain products based on dark chocolate for this analysis. First, a 1% solution of NHDC in glycerol was prepared by gradually adding 1 g of NHDC to 99 g of glycerol, stirring and heating to 60° C. for 15 minutes until a clear solution was obtained. The solution was left to cool to room temperature. The dark chocolate was weighed and heated to 45°C, and when the chocolate was completely melted, powdered sugar and optionally also a 1% solution of NHDC in glycerol or the composition of example B were added, and then the mixture was thoroughly mixed. The mixture was heated to reach 45°C, then left to cool to 30°C, and then poured into molds (6 g/sample). The molds with chocolate were placed in the refrigerator for quick hardening.

Example 9 Taste Masking Compositions

Various taste-masking compositions were prepared as complexes of neohesperidin dihydrochalcone with gamma-cyclodextrin (gCD) or beta-cyclodextrin (bCD) using various molar ratios shown in Table 12. NHDCs were purchased from Ferrer HealthTech and cyclodextrins were purchased from Wacker .

TABLE 12

Taste masking agent cyclodextrin NHDC:CD ratio Example A gCD 1:1 Example B gCD 1:3 Example C gCD 1.5:1 Example D gCD 1:6 Example E gCD 1:10 Example F bCD 1:1 Example G bCD 1:3

The sweetening compositions used were presented in the form of a complex.

To prepare the complex of example A, NHDC (14.0 g, 20.6 mmol) was added to a stirred solution of gCD (30 g, 20.6 mmol) in deionized water (500 ml). The mixture was stirred for one hour at 20-25°C until complete dissolution. The solution was clarified through a filter with a pore size of 0.8 μm to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (40 g) of the 1:1 complex was obtained.

To prepare the complex of example B, NHDC (7.5 g, 11 mmol) was added to a stirred solution of gCD (47.7 g, 33 mmol) in deionized water (500 ml). The mixture was stirred for one hour at 20-25°C until complete dissolution. The solution was clarified through a filter with a pore size of 0.8 μm to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (54 g) of the 1:3 complex was obtained.

The NHDC-gCD complexes of Examples C, D and E were prepared under the same conditions as described above for Examples A and B.

To obtain the complex of example F was added NHDC (7.0 g, 10.2 mmol) to a stirred solution of bCD (13.4 g, 10.2 mmol) in deionized water (900 ml) at 50°C. The mixture was stirred for two hours at 50°C until complete dissolution. The solution was clarified through a filter with a pore size of 0.8 μm to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (18.1 g) of the 1:1 complex was obtained.

To obtain the complex of example G was added NHDC (4.0 g, 5.8 mmol) to a stirred solution of bCD (22.9 g, 17.5 mmol) in deionized water (1500 ml) at 50°C. The mixture was stirred for two hours at 50°C until complete dissolution. The solution was clarified through a filter with a pore size of 0.8 μm to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (23.9 g) of the 1:3 complex was obtained.

Example 10: Masking the bitterness of paracetamol

The effect of masking the bitter taste of paracetamol was analyzed. The anti-bitter effect was measured as a dose-response profile relative to paracetamol solution.

The following substances were analyzed: only NHDC, only gamma-cyclodextrin and compositions containing NHDC and gamma-cyclodextrin in a molar ratio of 1:3 (example B), 1.5:1 (example C), 1:6 (example D) and 1 :10 (example E).

To assess the masking effect of each substance, several aqueous solutions were obtained containing 5000 ppm of paracetamol and various concentrations of the experimental substance, namely 5, 25, 50, 75 and 100 ppm

A certified tasting panel compared each solution with several solutions of paracetamol in water at various concentrations and determined the solution of paracetamol equal in bitterness. Equal bittering solution was calculated as the average of all commission ratings.

The masking effect was then calculated from the reference amount of paracetamol contained in each experimental solution (5000 ppm) and the amount of paracetamol in the solution equal in bitterness using the following formula ( Formula III ):

masking effect = 5000 - equal in bitterness to the amount of paracetamol (ppm) 5000

For example, a solution containing 5000 ppm paracetamol and 100 ppm NHDC was equal in bitterness to a solution containing 3266.7 ppm paracetamol. Thus, the masking effect was 34.67%.

In the same way, the masking effect was calculated for each substance at each concentration. The results are presented in table 13.

TABLE 13

Conc. (ppm) Masking effect (%) NHDC gCD Etc. A NHDC:gCD (1:1) Etc. B NHDC:gCD (1:3) Etc. C NHDC:gCD (1.5:1) Etc. D NHDC:g D (1:6) Etc. E NHDC:gCD (1:10) 5 6.00 1.00 1.33 2.00 3.00 6.00 4.00 25 14.00 2.00 5.67 6.67 9.00 7.70 5.30 fifty 15.33 4.00 9.33 12.00 10.00 9.30 8.70 75 27.00 5.00 22.00 18.33 14.00 12.00 10.70 100 34.67 6.00 30.67 27.00 14.50 15.30 12.00

To calculate the masking synergy between gamma-cyclodextrin and NHDC, first, for each amount of the combination (examples A-E), the amount of gamma-cyclodextrin and NHDC contained therein was calculated using the molecular weight of each component. For example, 100 ppm of example B contains 13.61 ppm NHDC and 86.39 ppm gamma-cyclodextrin. The anti-bitter contribution of each component was then calculated based on the data presented in Table 13. For example, 13.61 ppm NHDC provides 9.44% masking effect and 86.39 ppm gamma-cyclodextrin provides 5.46% masking effect (anti-bitter effect). for each specific concentration was calculated by interpolating the data points presented in Table 13). Thus, the expected masking effect was calculated as the sum of the contributions of each component. For example, the expected masking effect of 100 ppm of example B is 14.90% (i.e. 9.44 plus 5.46).

Finally, masking synergy was calculated using Formula IV :

Masking synergy (%) = Actual masking effect - expected masking effect x100 Expected masking effect

The results corresponding to the composition of NHDC-gCD with a molar ratio of 1:3 are presented in table 14.

TABLE 14

[Etc. B] (ppm) [gCD] (ppm) Expected masking contribution of gCD (%) [NHDC] (ppm) Expected masking contribution of NHDC (%) Expected masking effect (%) Actual masking effect (%) Synergy (%) 5 4.32 0.86 0.68 0.82 1.68 2.00 19.01 25 21.60 1.83 3.40 4.08 5.91 6.67 12.75 fifty 43.19 3.46 6.81 6.72 10.18 12.00 17.91 75 64.79 4.59 10.21 8.08 12.67 18.33 44.64 100 86.39 5.46 13.61 9.44 14.90 27.00 81.21

The masking effect of examples C (NHDC:gCD 1.5:1), D (NHDC:gCD 1:6) and E (NHDC:gCD 1:10) was also evaluated. Aqueous solutions were prepared, each containing 5000 ppm of paracetamol and various concentrations of each of the experimental formulations Pr. C-E, namely 25 and 50 ppm The results are presented in tables 15 - 17.

TABLE 15

[Etc. C] (ppm) [gCD] (ppm) Expected masking contribution of gCD (%) [NHDC] (ppm) Expected masking contribution of NHDC (%) Expected masking effect (%) Actual masking effect (%) Synergy (%) 25 14.55 1.16 10.45 5.85 7.02 9.00 28.28 fifty 29.10 2.33 20.90 6.41 8.74 10.00 14.45

TABLE 16

[Etc. D] (ppm) [gCD] (ppm) Expected masking contribution of gCD (%) [NHDC] (ppm) Expected masking contribution of NHDC (%) Expected masking effect (%) Actual masking effect (%) Synergy (%) 25 23.10 1.85 1.90 1.06 2.91 7.67 163.28 fifty 46.20 3.70 3.80 1.17 4.86 9.33 91.99

TABLE 17

[Etc. E] (ppm) [gCD] (ppm) Expected masking contribution of gCD (%) [NHDC] (ppm) Expected masking contribution of NHDC (%) Expected masking effect (%) Actual masking effect (%) Synergy (%) 25 23.83 1.91 1.18 0.66 2.56 5.33 108.01 fifty 47.65 3.81 2.35 0.72 4.53 8.67 91.20

Example 11: Masking the bitterness of quinine

The effect of masking the bitterness of quinine was analyzed using a method similar to that used in Example 10 for paracetamol.

The following substances were analyzed: NHDC only, beta-cyclodextrin only, a composition containing NHDC and beta-cyclodextrin in a 1:1 molar ratio (example F), and a composition containing NHDC and beta-cyclodextrin in a 1:3 molar ratio (example G) .

Similarly to example 10, several aqueous solutions were obtained containing 250 ppm of quinine and various concentrations of the experimental substance, namely 5, 25, 50, 75 and 100 ppm a formula analogous to formula III (replacing 5000 with 259). The masking effect of each substance at each concentration tested is listed in Table 18.

TABLE 18

Concentration (ppm) Masking effect (%) NHDC bCD Example F (1:1 NHDC:bCD) Example G (1:3 NHDC:bCD) 5 5.00 0.00 5.00 1.67 25 13.33 6.67 20.00 15.00 fifty 30.00 11.67 30.00 31.67 75 48.33 16.67 33.33 40.00 100 50.00 13.33 45.00 48.33

The masking synergy between beta-cyclodextrin and NHDC in examples F and G was calculated in a manner similar to that described in example 10. Thus, using the molecular weight of each component, the amount of beta-cyclodextrin and NHDC contained in each number of combinations of examples F and G was calculated. , then the contribution of each component against bitterness was calculated based on the data presented in Table 19. The expected masking effect was calculated as the sum of the contributions of each component, and finally the masking synergy was calculated (by formula IV).

The results of examples F and G are presented in tables 19 and 20, respectively.

TABLE 19

[Etc. F] (ppm) [bCD] (ppm) Expected masking contribution bCD (%) [NHDC] (ppm) Expected masking contribution of NHDC (%) Expected masking effect (%) Actual masking effect (%) Synergy (%) 5 3.25 0.00 1.75 1.75 1.75 5.00 185.15 25 16.23 3.74 8.77 6.57 10.31 20.00 93.91 fifty 32.47 8.16 17.53 10.22 18.38 30.00 63.20 75 48.70 11.41 26.30 14.20 25.61 33.33 30.17 100 64.93 14.65 35.07 20.05 34.70 45.00 29.69

TABLE 20

[Etc. G] (ppm) [bCD] (ppm) Expected masking contribution bCD (%) [NHDC] (ppm) Expected masking contribution of NHDC (%) Expected masking effect (%) Actual masking effect (%) Synergy (%) 5 4.24 0.00 0.76 0.76 0.76 1.67 118.49 25 21.19 5.40 3.81 3.81 9.21 15.00 62.88 fifty 42.37 10.14 7.63 6.10 16.24 31.67 95.04 75 63.56 14.38 11.44 7.68 22.06 40.00 81.30 100 84.74 15.37 15.26 9.27 24.64 48.33 96.15

Example 12 Masking the Astringent Taste of Green Tea Extract

The ability to mask astringent taste was measured in the same way as described for assessing the ability to mask bitterness (examples 10 and 11).

The following substances were analyzed: a composition containing NHDC and gamma-cyclodextrin in a molar ratio of 1:3 (example B), and a composition containing NHDC and beta-cyclodextrin in a molar ratio of 1:3 (example G), and only NHDC, only gamma -cyclodextrin and only beta-cyclodextrin. Experimental taste masking agents were dissolved in water along with 5 ppm green tea extract.

First, a certified taste panel compared a solution made with 30 ppm of Example G and 5 ppm of green tea extract with various stock solutions of green tea extract in water and determined an equal astringent stock solution in water. Two solutions were then prepared containing, respectively, proportional amounts of NHDC and beta-cyclodextrin contained in 30 ppm of example G, together with 5 ppm of green tea extract, and the tasting panel determined an equal astringent base solution in water for both solutions.

The masking effect of each substance was calculated using a formula similar to formula III (replacing 5000 with 5) and the astringent masking synergy between beta-cyclodextrin and NHDC in Example G was calculated using formula IV.

The masking effect and astringent taste masking synergy between gamma-cyclodextrin and NHDC for 30 ppm Example B was calculated in a similar manner.

The results are presented in Table 21:

TABLE 21

Etc. [gCD] (ppm) Expected masking contribution of gCD (%) [NHDC] (ppm) Expected masking contribution of NHDC (%) Expected masking effect (%) Actual masking effect (%) Synergy (%) G 25.60 28.00 4.40 10.00 38.00 50.00 33.33 B 25.92 19.00 4.08 8.00 27.00 33.00 23.26

Example 13: ¹ H NMR characterization of the NHDC:gCD complex

The composition of example A is presented in the form of a complex having a molar ratio of NHDC:gCD 1:1. It was obtained as described in examples 1 and 9.

^{The 1} H NMR spectrum of this complex was recorded in D ₂ O at 400 MHz and shown in FIG. 5.

In addition, ¹ H NMR of pure gamma-cyclodextrin in D ₂ O at 400 MHz (FIG. 6) and ¹ H NMR of pure NHDC in deuterated DMSO (DMSO-d6) at 400 MHz (FIG. 7) were also recorded and compared with the spectrum the specified complex.

In particular, the following table 22 compares the chemical shifts in ¹ H NMR for the H1 - H6 protons of pure gamma-cyclodextrin (FIG. 6) versus the chemical shifts of the equivalent protons in the complex (FIG. 5). Each proton in gamma CD is indicated in the schematic formula shown in FIG. eight.

TABLE 22

H in Gamma CD gCD(δ(ppm)) Example A
(δ(ppm)) ∆δ (ppm) _H1 5.016 4.971 0.045 _H2 3.841 3,760 0.081 _H3 3.561 3,540 0.021 _H4 3.495 3.465 0.030 _H5 3.759 3.673 0.086 _H6 3.778 3.701 0.077

It can be seen that there is a change in chemical shifts in the complex compared to pure cyclodextrin (last column of the table).

Similarly, the following Table 23 provides, in particular, a comparison of ¹ H NMR chemical shifts for pure NHDC protons (FIG. 7) versus equivalent proton chemical shifts when NHDC forms part of the complex, in Example A (FIG. 5). Each proton in NHDC is indicated in the schematic formula shown in FIG. 9.

TABLE 23

H at NHDC NHDC (δ(ppm)) Example A (δ(ppm)) ∆δ (ppm) H-5' 6.788 6.688 0.100 H-2' 6.647 6.519 0.128 H-6' 6.587 6.357 0.230 H-6 H-8 5,998 5.907 5.050 0.091 0.948 G-1 5.121 5.010 0.111 CH ₂ (2) 2.723 (t) 2.611 (m) 0.112 CH ₂ (3)** 3.251 (t) 3.050 (m) 0.201

It can be seen that there is a change in chemical shifts in the complex compared to pure NHDC (last column of the table).

In addition, it can also be seen that the H-6 and H-8 protons, which are chemical equivalents in pure NHDC, differ in the complex of example A. In addition, the protons in the methylene groups (CH ₂ ) at positions 2 and 3, which appear as triplets in ¹ H NMR NHDC appear as multiplets in this complex.

Claims (16)

1. A sweetener composition containing a simple mixture of neohesperidin dihydrochalcone and gamma cyclodextrin, or in which neohesperidin dihydrochalcone and gamma cyclodextrin are present in the form of a complex, which is an inclusion complex formed between neohesperidin dihydrochalcone and gamma cyclodextrin. 2. Composition according to claim 1, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1.5:1 to 1:10. 3. Composition according to claim 1 or 2, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is from 1.5:1 to 1:6. 4. The composition according to any one of paragraphs. 1-3, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is approximately 1:1. 5. The composition according to any one of paragraphs. 1-3, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is approximately 1 ± 0.1:1 ± 0.1. 6. Composition according to claim 5, characterized in that the molar ratio of neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.05: 1 ± 0.05. 7. The composition according to any one of paragraphs. 1-3, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is approximately 1:3. 8. The composition according to any one of paragraphs. 1-3, characterized in that the molar ratio of neohesperidin dihydrochalcone:gamma-cyclodextrin is approximately 1 ± 0.1:3 ± 0.3. 9. Composition according to claim 8, characterized in that the molar ratio of neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.05: 3 ± 0.15. 10. The use of a sweetening composition according to any one of paragraphs. 1-9 for sweetening the edible product. 11. Use according to claim 10, characterized in that the edible product is selected from a food product and a pharmaceutical product. 12. The method of sweetening an edible product, including adding a sweetening composition according to any one of paragraphs. 1-9 to an edible product. 13. An edible product containing a sweetening composition according to any one of paragraphs. 1-9. 14. Use of a composition containing a simple mixture of neohesperidin dihydrochalcone and cyclodextrin, or in which neohesperidin dihydrochalcone and cyclodextrin are in the form of a complex, which is an inclusion complex formed between neohesperidin dihydrochalcone and cyclodextrin, wherein the cyclodextrin is selected from beta-cyclodextrin and gamma-cyclodextrin , as a taste masking agent. 15. A method for masking an unpleasant taste of a edible product that contains at least one unpleasant tasting substance, comprising adding to the edible product a taste masking composition containing a simple mixture of neohesperidin dihydrochalcone and cyclodextrin, or in which neohesperidin dihydrochalcone and cyclodextrin are presented in the form of a complex, which is an inclusion complex formed between neohesperidin dihydrochalcone and a cyclodextrin, the cyclodextrin being selected from beta-cyclodextrin and gamma-cyclodextrin. 16. An edible product that contains at least one objectionable tasting substance and a taste masking composition comprising a simple mixture of neohesperidin dihydrochalcone and cyclodextrin, or in which neohesperidin dihydrochalcone and cyclodextrin are present in the form of a complex, which is an inclusion complex formed between neohesperidin dihydrochalcone and cyclodextrin, while the cyclodextrin is selected from beta-cyclodextrin and gamma-cyclodextrin.

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