METHODS, COMPOUNDS, AND COMPOSITIONS,

FOR MODULATING SWEET TASTE

Cross-Reference to Related Application [0001] This application claims the benefit of U.S. Provisional Application

62/327,825 filed on April 26, 2016, the disclosure of which is incorporated herein by reference in its entirety.

Field

[0002] The present invention relates to improved sweeteners and flavor in edible compositions.

Background [0003] There is an increasing demand worldwide to have broader available choices of reduced sugar content in foods and beverages, whether for taste preference, lifestyle reasons or for certain individuals (e.g., diabetic patients) for health-related goals. Accordingly, health benefits associated with the reduction of sugar content in foods and beverages is desirable. The use of non-caloric artificial and natural high-potency sweeteners to reduce the level of sweeteners such as caloric and non-caloric sweeteners in foods is limited due to temporal, mouthfeel and/or flavor issues, e.g., slow onset of sweetness, sweetness linger, thickness or thinness, bitter, metallic, astringent or licorice taste. It is, therefore, desirable to provide methods to improve such temporal, mouthfeel and/or flavor issues. Any improved sweeteners or sweet taste modulators may be added to food products, consumer products and pharmaceuticals allowing for the use of reduced amounts of caloric sweeteners (e.g., sugars) while maintaining desirable sweet taste and avoiding the flavor, mouthfeel and temporal issues associated with sugar substitutes and sweet taste modulators.

Summary

[0004] The present disclosure provides methods that reduce the negative taste attributes and/or improve the positive taste attributes of sugar

substitutes and sweet taste modulators (e.g. enhancers). It was surprisingly discovered that esterification of sweeteners and sweet taste modulators improves their taste attributes including temporal profile (e.g. faster onset of sweet taste, reduced duration ('linger') of sweet taste), enhanced sweetness, and/or reduced bitterness, reduced astringency or reduced licorice taste.

Such esterified sweeteners (or salts thereof) and esterified sweetness

modulators (or salts thereof) could be added to foods, beverages,

pharmaceutical compositions and edible consumer products that would be consumer preferred.

[0005] Such esterified sweeteners and esterified sweet taste modulators may be combined with or replace any suitable sweetener, such as a natural caloric sweetener, a natural high-potency sweetener, a synthetic sweetener including a synthetic high-potency sweetener, sugar alcohols, rare sugars, sweetener enhancers or combinations thereof, to provide a composition having an improved taste.

[0006] Other aspects of the present disclosure include edible compositions, such as beverage compositions, concentrates (for use in, e.g., beverage compositions), food products, pharmaceutical preparations and table-top sweeteners comprising the compositions of the present disclosure; methods for preparing an edible composition; methods for reducing the amount of a sweetener in an edible composition; methods for reducing caloric intake; methods of enhancing activation of a sweet taste receptor.

[0007] The esters of this invention can be isolated and purified and then used (e.g. added to a food, beverage or pharmaceutical preparation) or instead can be used as part of a reaction mixture or crude form.

[0008] Particular embodiments are set forth as follows: In some embodiments a method of improving at least one sensorial characteristic of a sweetener, the method comprising esterif ing one or more hydroxyl groups of such sweetener.

[0009] In some embodiments a method comprising esterifying one or more hydroxyl groups of a sweetener, wherein at least one sensorial characteristic of the sweetener is improved, compared to a sweetener that is not esterified at at least one hydroxyl group.

[0010] In some embodiments the method disclosed herein comprises esterifying at least one hydroxyl group of a sweetener as disclosed herein.

[0011] In some embodiments the sensorial characteristic of a sweetener is selected from: improved taste, improved temporal profile, faster onset of perception of sweetness, reduced lingering of sweet taste, reduction in bitterness, reduction of licorice taste, and increased potency of sweetness.

[0012] In some embodiments a method of improving at least one sensorial characteristic of a sweet taste modulator comprising the esterification of one or more hydroxyl groups on such sweet taste modulator.

[0013] In some embodiments a method of improving one or more sensorial characteristic of a sweet taste modulator comprising the esterification of one or more hydroxyl groups on such sweet taste modulator.

[0014] In some embodiments a method of improving two or more sensorial characteristic of a sweet taste modulator comprising the esterification of one or more hydroxyl groups on such sweet taste modulator.

[0015] In some embodiments a method of improving one or more sensorial characteristic of a sweet taste modulator comprising the esterification of at least one hydroxyl groups on such sweet taste modulator.

[0016] In some embodiments a method of improving one or more sensorial characteristic of a sweet taste modulator comprising the esterification of two or more hydroxyl groups on such sweet taste modulator.

[0017] In some embodiments the sensorial characteristic of a sweet taste modulator is selected from: improved taste, improved temporal profile, faster onset of perception of sweetness, and increased degree of sweet taste enhancement, of a sweetener. [0018] In some embodiments the sensorial characteristic of a sweet taste modulator is selected from: improved taste, improved temporal profile, and faster onset of perception of sweetness. In some embodiments a method of improving at least one sensorial characteristic of an esterified sweetener or esterified sweet taste modulator, wherein the sensorial characteristic is selected from: improved taste, improved temporal profile, faster onset of perception of sweetness, reduced lingering of sweet taste, reduction in bitterness, reduction of licorice taste, reduction in metallic taste, reduction in astringent taste and increased potency of sweetness.

[0019] In some embodiments a method of improving the taste of a sweetener comprising esterif ing one or more hydroxyl groups of such sweetener.

In some embodiments a method of improving the temporal profile of a sweetener esterified at one or more hydroxyl groups.

[0020] in some embodiments a method wherein the onset of the perception of sweetness from a sweetener esterified at one or more hydroxyl groups is more rapid.

[0021] In some embodiments a method wherein the linger of sweet taste from a sweetener esterified at one or more hydroxyl groups is diminished.

In some embodiments a method for reducing the bitterness of a sweetener, the method comprising esterifying said sweetener at one or more of its hydroxyl groups.

[0022] In some embodiments a method for reducing the licorice taste of a sweeter, the method comprising esterifying said sweetener at one or more of its hydroxyl groups.

[0023] In some embodiments a method of increasing potency of sweetness of a sweetener, the method comprising esterifying said sweetener at one or more of its hydroxyl groups.

[0024] In some embodiments a method of improving the taste of a sweet taste modulator, the method comprising esterifying said sweet taste modulator at one or more hydroxyl groups on said sweet taste modulator. [0025] In some embodiments a method of improving temporal profile of a sweet taste modulator, the method comprising esterifying said sweet taste modulator at one or more of its hydroxyl groups.

[0026] In some embodiments a method of reducing the time of perception of sweetness of a sweet taste modulator, the method comprising esterifying said sweet taste modulator at one or more of its hydroxyl groups.

[0027] In some embodiments a method of increasing enhancement of sweetness of a sweet taste modulator, the method comprising esterifying said sweet taste modulator at one or more of its hydroxyl groups.

[0028] In some embodiments a method of improving the taste of a food, beverage, pharmaceutical composition or consumer product comprising adding an effective amount of an esterified sweetener, esterified sweet taste modulator or a

combination thereof to such food, beverage, pharmaceutical composition or consumer product.

[0029] In some embodiments a method the esterified sweetener, esterified sweet taste modulator or a combination thereof are added in their pure form.

[0031] In some embodiments a method the esterified sweetener, esterified sweet taste modulator or a combination thereof are added in their crude form or as part of a reaction mixture.

[0032] In some embodiments the esterified sweetener, esterified sweet taste modulator or a combination thereof comprises an extract.

[0033] In some embodiments the esterified sweetener, esterified sweet taste modulator or a combination thereof is added in form of an extract.

[0034] In some embodiments the sweetener as disclosed herein is a high potency sweetener.

[0035] In some embodiments the high potency sweetener is a natural high potency sweetener.

[0036] In some embodiments the natural high potency sweetener is steviol glycoside, rebaudioside A, rebaudioside B, rebaudioside C (dulcoside B), rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M, dulcoside A, rubusoside, stevia leaf extract, stevioside, glycosylated steviol glycosides, mogrosides, mogroside V, isomogroside, mogroside IV, Luo Han Guo fruit extract, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hemandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, or cyclocarioside I or mixtures thereof.

[0037] In some embodiments the natural high potency sweetener is rebaudioside M, rebaudioside A or stevioside.

[0038] In some embodiments the natural high potency sweetener is a mogroside.

[0039] In some embodiments the sweetener is a synthetic high potency sweetener.

[0040] In some embodiments the synthetic high potency sweetener is sucralose, acesulfame potassium or other salts, aspartame, alitame, saccharin, neohesperidin dihydrochalcone, cyclamate, neotame, or advantame, or mixtures thereof.

[0041] In some embodiments a composition comprising an esterified sweetener or an esterified sweet taste modulator, or combinations thereof, or comestibly or biologically acceptable salts or derivatives thereof, wherein said composition is edible and capable of improving the sweet taste of a sweetener.

[0042] In some embodiments a composition wherein the esterified sweetener or esterified sweet taste modulator is present in one or more natural extracts.

[0043] In some embodiments a composition wherein the composition further comprises a sweetener.

[0044] In some embodiments a composition wherein the composition further comprises a solubilizing agent.

[0045] In some embodiments a composition wherein the sweetener is a caloric sweetener, an artificial sweetener, a natural high-potency sweetener, or

combinations thereof.

[0046] In some embodiments a composition, wherein the caloric sweetener is a carbohydrate selected from sucrose, high fructose corn or starch syrup, glucose and fructose.

[0047] In some embodiments a composition wherein the caloric sweetener is high fructose corn or starch syrup. [0048] In some embodiments a composition wherein the caloric sweetener is sucrose.

[0049] In some embodiments a composition wherein the caloric sweetener is a polyol selected from erythritol, sorbitol, mannitol and xylitol.

[0050] In some embodiments a composition, wherein the artificial sweetener is sucralose, acesulfame potassium or other salts, aspartame, alitame, sodium or calcium salt of saccharin, neohesperidin dihydrochalcone, sodium cyclamate, neotame, advantame, and salts thereof.

[0051] In some embodiments a composition, wherein the natural high-potency sweetener is steviol glycoside, rebaudioside A, rebaudioside B, rebaudioside C (dulcoside B), rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, Rebaudioside M, dulcoside A, rubusoside, stevia leaf extract, stevioside, glycosylated steviol glycosides, mogroside V, isomogroside, mogroside IV, Luo Han Guo fruit extract, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, or cyclocarioside I and mixtures thereof.

[0052] In some embodiments method of preparing an edible composition comprising, providing a comestibly acceptable carrier; and adding to said comestibly acceptable carrier a esterified sweetener, esterified sweet taste modulator or a combination of the foregoing.

[0053] In some embodiments a composition wherein said composition is a beverage selected from the group consisting of a non-carbonated beverage, carbonated beverage, cola, root beer, fruit flavored beverage, citrus-flavored beverage, fruit juice, fruit-containing beverage, vegetable juice, vegetable containing beverage, tea, coffee, dairy beverage, sports drinks, energy drinks, enhanced and flavored water.

[0054] In some embodiments a composition, wherein the composition is used in food, beverage products, pharmaceutical compositions, nutritional products, functional products, a dietary supplement, over-the-counter medications, or oral care products.

[0055] In some embodiments a tabletop sweetener composition comprising an esterified sweetener or esterified sweet taste modulator or a combination thereof.

[0056] In some embodiments a tabletop sweetener composition, further comprising at least one bulking agent, additive, anti-caking agent, functional ingredient and combinations thereof.

[0057] In some embodiments a tabletop sweetener composition, wherein the tabletop sweetener composition is in the form of a liquid.

[0058] In some embodiments a composition as disclosed herein, wherein the food or beverage product is selected from the group consisting of soup, powdered soft drinks, bakery products, chewing gums, confections, cereals, edible gels, jams and jellies, spreads, ketchup, dairy products, frozen dairy products, gelatins/puddings, ice-creams.

[0059] In some embodiments a composition, wherein the composition is a beverage.

[0060] In some embodiments, the sweet taste modulator is a compound according to Formula I:

or comestibly or biologically acceptable salts or derivatives thereof,

wherein: Rl, R2, R3, R4 are each independently methyl, ethyl, hydroxyl, methoxy, ethoxy or hydrogen and least one R in the formula is a hydroxyl group.

[0061] In some embodiments, the sweet taste modulator is a compound according to Formula II:

or comestibly or biologically acceptable salts or derivatives thereof,

wherein: Rl, R2, R3, R4 are each independently methyl, ethyl, hydroxyl, methoxy, ethoxy or hydrogen and least one R in the formula is a hydroxyl group.

[0062] In some embodiments, the estenfied sweet taste modulator is selected from any one of Compounds 2, 4, or 6:

[0063] In some embodiments, the sweet taste modulator is a compound selected a compound according to Formula I, Formula II, or any one of compounds 2, 4, or 6, or a combination of the foregoing.

[0064] In some embodiments, the sweet taste modulator is a compound selected a compound according to Formula I, Formula II, or any one of compounds 2, 4, or 6, or a combination of the foregoing, wherein the esterified sweetener is present in one or more natural extracts.

[0065] In some embodiments, the sweet taste modulator is a compound selected a compound according to Formula I, Formula II, or any one of compounds 2, 4, or 6, or a combination of the foregoing, wherein the compound is isolated and purified.

Brief Description of the Drawings

[0066] Figure 1 depicts the ESI MS Spectrum of Reb M acetate.

[0067] Figure 2 depicts a NMR spectra of Compound 2.

[0068] Figure 3 depicts DA assessment of off-taste profile of Compound 1 and Compound 2 (esterified Compound 1). The * indicates significance by ANOVA at 95% CL.

[0069] Figure 4 depicts a NMR spectra of Compound 4.

[0070] Figure 5 depicts DA assessment of off-taste profile of Compound 3 and Compound 4 (esterified Compound 3). The * indicates significance by ANOVA at 95% CL.

[0071] Figure 6 depicts a NMR spectra of Compound 6.

[0072] Figure 7 depicts DA assessment of off-taste profile of Compound 5 and Compound 6 (esterified Compound 5). The * indicates significance by ANOVA at 95% CL.

Detailed Description

[0073] In order that the invention described herein may be fully understood, the following detailed description is set forth.

[0074] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as those commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, suitable methods and materials are described below. The materials, methods and examples are illustrative only, and are not intended to be limiting. All publications, patents and other documents mentioned herein are incorporated by reference in their entirety.

[0075] Throughout this specification, the word "comprise" or variations such as "comprises" or "comprising" will be understood to imply the inclusion of a stated integer or groups of integers but not the exclusion of any other integer or group of integers.

[0076] The term "bitter" or "bitter taste" as used herein refers to the perception or gustatory sensation resulting following the detection of a bitter tastant. The following flavor attributes may contribute to bitter taste: astringent, bitter- astringent, metallic, bitter-metallic, as well as off-tastes aftertastes and undesirable tastes including but not limited to freezer-burn and card-board taste or a combination of these. It is noted that, in the art, the term "off-taste" is often synonymous with "bitter taste."

[0077] The term "bitter tastant" refers to a compound that activates or that can be detected by a bitter taste receptor and/or confers the perception of a bitter taste in a subject. A "bitter tastant" also refers to a multiplicity of compounds that combine to activate or be detected by a bitter taste receptor and/or confer the perception of a bitter taste in a subject. Those of skill in the art can readily identify and understand what is meant by a bitter tastant. Bitter tastants may include substances which also possess or primarily possess a sweet taste. Examples of such substances include steviol glycosides and acesulfame potassium.

[0078] The term "diet" collectively refers to the food products and/or beverages consumed by a subject. A subject's "diet" also includes any consumer products or pharmaceutical compositions the subject ingests.

[0079] The term "flavor modifier" refers to a compound or a mixture of compounds that, when added to an edible composition, such as a food product, changes the individual characteristics of a food flavor (odor and/or taste). Flavor modification effects can include increasing, decreasing, masking, eliminating, reducing, enhancing or changing the perception of relevant sensorial characteristics of flavor in the edible composition. The ability of flavor modifiers to modify flavor may be independent of their aromatic or taste characteristics.

[0080] The term "pharmaceutically active ingredient" refers to a compound in a pharmaceutical composition which is biologically active.

[0081] The term "replace" or "replacing" refers to substituting one compound for another compound in or in the preparation of, for example, an edible composition, such as food product. It includes complete and partial replacements or

substitutions.

Improved Sweet Taste Modulators

[0082] According to one aspect, the invention provides methods for improving the taste or performance of substances modulating sweet taste (e.g., enhancing or potentiating the sweet taste of a sweetener). Selective esterification of the hydroxyl groups of such sweet taste modulators improves the overall liking of edible comestibles comprising such sweet taste modulators and may increase the potency of such sweet taste modulators.

[0083] As used herein, the term "sweet taste modulators" refers to flavor substances with taste modifying properties. Sweetness enhancers are understood to be a type of "sweet taste modulator" where perception of sweetness is increased in a manner not solely attributable to the inherent sweetness of the sweetness enhancer alone. The term "sweetness enhancer" is understood to include at least compositions capable of enhancing or intensifying the perception of sweet taste of sweetener compositions or sweetened compositions. The term "sweetness enhancer" is synonymous with the terms "sweet taste potentiator," "sweetness potentiator," "sweetness amplifier," and "sweetness intensifier." Sweet taste modulating compositions to enhance flavor profile of sweetener compositions are described in detail in Patent Application Nos. US2015/0050410,

PCT/US2015/48400, and PCT/US2016/13296. Generally, the improved sweet taste modulating compounds provided herein (which serve to enhance the perception of sweetness) may enhance or potentiate the sweet taste of sweeteners without providing any noticeable sweet taste by themselves at acceptable use levels;

however, the sweetness enhancers may themselves provide sweet taste at concentrations above a sweetness threshold level. It is noted that the sweetness enhancers may be effective as enhancers even if present at concentrations above their sweetness threshold level. In such embodiments, there is major contribution of the sweetness enhancer to the sweetness of the composition via enhancement of the inherently sweet taste attributed to a sweetener, where the sweetener is also present in the composition. As used herein, the term "sweetness threshold level" is understood to include at least the concentration at which the sweetness is perceptible as sweet in the edible compositions. The sweetness threshold level varies for different edible compositions (e.g., in different matrices), and may be varied with respect to the individual perceiving the sweetness.

[0084] In all embodiments of the present invention, the sweet taste modulator(s) of the present invention is a different compound from any sweetener. Accordingly, although an ingredient may be characterized as both a sweet taste modulator and a sweetener, in all embodiments of the disclosure, the sweet taste modulator and the sweetener are different ingredients, i.e., the sweet taste modulator and the sweetener are not the same compound.

[0000] Each embodiment of the invention described herein may be taken alone or in combination with one or more other embodiments of the invention.

[0030] The term "comestibly or biologically acceptable salt" refers to any comestibly or biologically acceptable salt, ester, or salt of such ester, of a sweet taste modulator of the present invention, which, upon ingestion, is capable of providing (directly or indirectly) a sweet taste modulator of the present invention, or a polymorph, metabolite, residue or portion thereof, characterized by the ability to enhance the perception of a sweet taste attributed to a sweetener. Similarly, the term "comestibly or biologically acceptable derivative" refers to any comestibly or biologically acceptable derivative of a sweet taste modulator of the present invention, which, upon ingestion, is capable of providing (directly or indirectly) a sweet taste modulator of the present invention, or a polymorph metabolite, residue or portion thereof, characterized by the ability to enhance the perception of a sweet taste attributed to a sweetener. A "comestible product" is a product suitable for oral use, such as eating or drinking. Therefore, a comestibly acceptable compound is an edible compound.

[0031] If a comestibly or biologically acceptable salt of a compound of the present invention is used, such salt is preferably derived from inorganic or organic acids and bases. Examples of such salts include, but are not limited to, acetate, adipate, alginate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, citrate, camphorate, camphorsulfonate, cyclopentanepropionate, digluconate,

dodecyl sulfate, ethanesulfonate, formate, fumarate, glucoheptanoate, glycerophosphate, glycolate, hemisulfate, heptanoate, hexanoate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxyethanesulfonate, lactate, maleate, malonate, methanesulfonate, 2-naphthalenesulfonate, nicotinate, nitrate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, phosphate, picrate, pivalate, propionate, salicylate, succinate, sulfate, tartrate, thiocyanate, tosylate and undecanoate. Salts derived from appropriate bases include alkali metal (e.g., sodium and potassium), alkaline earth metal (e.g., magnesium), ammonium and N+ (Cl-4 alkyl)4 salts. This invention also envisions the quaternization of any basic nitrogen-containing groups of the compounds disclosed herein. Water or oil-soluble or dispersible products may be obtained by such quaternization. In some embodiments, the compounds of the present invention are present as sodium, potassium or citrate salts.

[0032] The term "comestibly or biologically acceptable derivative" refers to any comestibly or biologically acceptable derivative of a sweet taste modulator of the present invention, which, upon ingestion, is capable of providing (directly or indirectly) a sweet taste modulator the present invention, or a polymorph, metabolite, residue or portion thereof, characterized by the ability to improve taste attributed to a sweetener or reduce or block the perception of aversive taste attributed to certain sweeteners. A "comestible product" is a product suitable for oral use, such as eating or drinking. Therefore, a comestibly acceptable compound is an edible compound.

[0033] The terms "effective concentration" and "effective amount" are used interchangeably herein and refer to an amount sufficient to produce a desired property or result. For example, an effective amount of a sweet taste modulator of the present invention is an amount capable of modulating (e.g., enhancing) the perception of sweet taste associated with a sweetener. The term "effective amount" of a sweet taste modulator of the invention also refers to an amount which, when added to an edible composition, enhances the sweet taste of, e.g., a sugar, thereby allowing for the maintenance of the perception of a desired sweet flavor of the edible composition. The term "effective amount" also refers to the amount of an esterified sweet taste modulator or esterified sweetener of the present invention capable of improving the taste of a food product or an inherently sweet food product. The sweet taste modulators of the present invention may impart a sweetness or taste at certain concentrations and no perceptible sweetness or taste at other concentrations.

Improved Sweeteners

[0034] In compositions and methods of the invention that comprise a sweetener, the sweetener can be of any type, for example a natural, non-natural, or synthetic sweetener. Non-limiting examples of such sweeteners include caloric

carbohydrate sweeteners, natural carbohydrate sweeteners, non-natural

carbohydrate sweeteners, natural high-potency sweeteners, non-natural high- potency sweeteners, synthetic high potency sweeteners, synthetic carbohydrate sweeteners, sugar alcohols, rare sugars and combinations thereof. In some embodiments, the at least one sweetener is chosen from caloric sweeteners. In another embodiment, the at least one sweetener is chosen from synthetic sweeteners. In another embodiment, the at least one sweetener is chosen from non- natural sweeteners. Non-limiting examples of rare sugars include D-Psicose, D- Turanose, D-allose, D-Tagatose, D-Sorbose, L-fructose, L-glucose, L-fructose, L- talose, L-ribose, L-arabinose.

[0035] In some embodiments, the sweetener is a natural or inherent component of an edible composition. For example, the sweetener may be an inherent component of a food product or of a food stuff, such as fruit or a fruit product (e.g., fruit sauce). Accordingly, the compounds of the present invention may be used in edible compositions to which no sweetener is added.

[0036] The terms "caloric sweeteners" and "caloric carbohydrate sweeteners," are used interchangeably herein, and refer to nutritive sweeteners that provide calories and include all caloric carbohydrate sweeteners, such as sugars and polyols. Non-limiting examples of suitable caloric carbohydrate sweeteners include sucrose, fructose, glucose, erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol, D-tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g., - cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), ribulose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, glucono- lactone, abequose, galactosamine, xylo-oligosaccharides (xylotriose, xylobiose and the like), gentio-oligoscaccharides (gentiobiose, gentiotriose, gentiotetraose and the like), galacto-oligosaccharides, sorbose, nigero-oligosaccharides,

fructooligosaccharides (kestose, nystose and the like), maltotetraol, maltotriol, malto-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose and the like), lactulose, melibiose, raffinose, rhamnose, ribose, isomerized liquid sugars such as high fructose corn/starch syrup (e.g., HFCS55, HFCS42, or HFCS90), honey, maple syrup, coupling sugars, soybean

oligosaccharides, and glucose syrup.

[0037] The term "polyol," as used herein, refers to a molecule that contains more than one hydroxyl group. A polyol may be a diol, triol, or a tetraol which contain 2, 3, and 4 hydroxyl groups, respectively. A polyol also may contain more than four hydroxyl groups, such as a pentaol, hexaol, heptaol, or the like, which contain 5, 6, or 7 hydroxyl groups, respectively. Additionally, a polyol also may be a sugar alcohol, polyhydric alcohol, or polyalcohol which is a reduced form of carbohydrate, wherein the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Non-limiting examples of polyols in some embodiments include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerin), threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, reduced glucose syrup, and sugar alcohols or any other carbohydrates capable of being reduced which do not adversely affect the taste of the edible composition.

[0038] In some embodiments, the sweetener is a carbohydrate sweetener. In such embodiments, the sweetener is chosen from sucrose, fructose, glucose, erythritol, high fructose corn or starch syrup, and mixtures thereof.

[0039] The terms "synthetic high potency sweetener" and "artificial high potency sweetener" are used interchangeably herein and refer to any composition which is not found naturally in nature and characteristically has a sweetness potency greater than sucrose, fructose, or glucose, yet have fewer or no calories. Non-limiting examples of synthetic sweeteners suitable for embodiments of this invention include sucralose, acesulfame potassium or other salts, aspartame, alitame, saccharin, neohesperidin dihydrochalcone, cyclamate, neotame, advantame, and salts thereof.

[0040] In some embodiments, the sweetener is a synthetic sweetener. Preferably, the synthetic sweetener is chosen from sucralose, aspartame, potassium

acesulfame, and mixtures thereof.

[0041] Other sweeteners suitable for use in embodiments provided herein, for example, include natural sweeteners. The terms "natural high-potency sweetener," "NHPS," "NHPS composition," and "natural high-potency sweetener composition" are used interchangeably, herein, and refer to any sweetener found in nature which may be in raw, extracted, purified, or any other form, singularly or in combination thereof and characteristically have a sweetness potency greater than sucrose, fructose, or glucose, yet have fewer or no calories. Non-limiting examples of NHPSs suitable for embodiments of this disclosure include steviol glycoside, rebaudioside A, rebaudioside B, rebaudioside C (dulcoside B), rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M, dulcoside A, rubusoside, stevia leaf extract, stevioside, glycosylated steviol glycosides, mogrosides, mogroside V, isomogroside, mogroside IV, Luo Han Guo fruit extract, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, or cyclocarioside I. NHPS also includes modified NHPSs. Modified NHPSs include NHPSs which have been altered naturally. For example, a modified NHPS includes, but is not limited to, NHPSs which have been fermented, contacted with enzyme, or derivatized or substituted on the NHPS. In one embodiment, at least one modified NHPS may be used in combination with at least one NHPS. In another embodiment, at least one modified NHPS may be used without a NHPS. Thus, modified NHPSs may be substituted for a NHPS or may be used in combination with NHPSs for any of the embodiments described herein. For the sake of brevity, however, in the description of embodiments, a modified HPS is not expressly described as an alternative to an unmodified NHPS, but it should be understood that modified NHPSs can be substituted for NHPSs in any embodiment disclosed herein.

[0042] In some embodiments, the improved esterified sweetener may be used individually or in combination with other sweeteners. For example, the sweetener composition may comprise a single caloric sweetener, a single NHPS or a single synthetic sweetener; a single caloric sweetener with a single NHPS; a single caloric sweetener with a single synthetic sweetener; one or more caloric sweetener with a single NHPS; one or more caloric sweetener with a single synthetic sweetener; a single caloric sweetener with one or more NHPS; a single caloric sweetener with one or more synthetic sweeteners; a single NHPS in combination with a single synthetic sweetener; one or more NHPSs in combination with a single synthetic sweetener; a single NHPS in combination with one or more synthetic sweeteners; one or more NHPSs in combination with one or more synthetic sweeteners; or one or more caloric sweetener with one or more NHPS and one or more synthetic sweetener. A plurality of natural and/or synthetic sweeteners may be used as long as the combined effect does not adversely affect the taste of the sweetener composition or orally sweetened composition.

[0043] One of ordinary skill in the art should appreciate that the improved esterified sweetener composition can be customized to obtain a desired calorie content. For example, a low-caloric or non-caloric esterified synthetic sweetener may be combined with a caloric sweetener and/or other caloric additives to produce a sweetener composition with a preferred calorie content.

[0044] The esterified sweetener is present in the composition in an amount greater than its sweetness threshold level. In some embodiments, the esterified sweetener may be present in an amount ranging from 0.01% to 99.9% by weight, relative to the total weight of the composition. For example, the at least one esterified sweetener may be present in an amount ranging from 2% to 50%, or for example from 4% to 50% by weight, relative to the total weight of the

composition. In some embodiments, the at least one esterified sweetener may be present in about 5% to 20% by weight. In further embodiments, the at least one esterified sweetener may be present in about 5% to 15% by weight. In yet further embodiments, the at least one esterified sweetener may be present in about 5% to 12%) by weight in beverages, for example, in non-alcoholic beverages.

[0045] The sweetness of a composition may be based on (i.e., relative to) a known sweet standard. Sweet compounds based on such sweet standards include, but are not limited to, for example natural, non-natural, or synthetic sweeteners. Non- limiting examples of such sweeteners include caloric carbohydrate sweeteners, natural carbohydrate sweeteners, non-natural carbohydrate sweeteners, natural high-potency sweeteners, non-natural high-potency sweeteners, synthetic high potency sweeteners, synthetic carbohydrate sweeteners, and combinations thereof. For example, the sweetness of a composition may be based on to a 5% sucrose solution. In such cases, a composition comprising the esterified sweetener, an esterified sweet taste modulator or a combination of the foregoing invention may be perceived as having a sweetness equivalent to a 5.5% sucrose solution. In other embodiments, the composition comprising the esterified sweetener esterified sweet taste modulator or a combination of the foregoing of the present invention may be perceived as having a sweetness equivalent to a 6.0%, 6.5%, Ί.0%, 1.5%, 8.0%>, 8.5%), 9.0%), 9.5%o, or 10%> sucrose solution. Suitable sweet standards include, but are not limited to, sucrose standards, fructose standards and glucose standards. Each of these standards may be used at concentrations which include, but are not limited to, 0.5%, 1.0%, 1.5%, 2.0%, 2.5%, 3.0%, 3.5%, 4.0%, 4.5%, 5.0%, 5.5%, 6.0%, 6.5%, 7.0%, 7.5%, 8.0%, 8.5%, 9.0%, 9.5%, or 10% solution.

[0046] It is contemplated that the combination of at least one esterified sweetener, esterified sweetness enhancer or a combination of the foregoing and at least one sweetener may be carried out in any pH range that does not materially or adversely affect the taste of the sweetener composition or the sweetened composition. A non-limiting example of the pH range may be from about 1.5 to about 9.0. Further examples include a pH range from about 2.0 to about 8.5, from about 2.0 to about 8.0, from about 2.0 to about 7.5, from about 2.0 to about 7.0, from about 2.5 to about 7.0, and from about 3.0 to about 7.0. Additional examples of pH ranges include from about 2.0 to about 4.0, from about 2.5 to about 4.5, from about 3.5 to about 5.5, from about 5.0 to about 6.0, from about 4.0 to about 5.5, from about 5.0 to about 6.0, from about 6.5 to about 7.5, and from about 6.0 to about 8.0. In some embodiments, the pH is about 3.0 or about 7.0. The temperature of the composition may, for example, range from about -4° C to about 90° C.

[0047] One of ordinary skill in the art may combine the esterified sweetener(s) and esterified sweet taste modulator(s), in any manner with or without another sweetener or sweet taste modulator.

[0048] The terms "sugar-like characteristic," "sugar-like taste," "sugar-like sweet," "sugary," and "sugar-like" are used interchangeably, herein, and include any characteristic similar to that of sucrose and include, but are not limited to, maximal response, flavor profile, temporal profile, adaptation behavior, mouth feel, concentration/response function behavior, tastant and flavor/sweet taste interactions, spatial pattern selectivity, and temperature effects. These

characteristics are dimensions in which the taste of sucrose is different from the tastes of sweetness enhanced sweetener compositions. Suitable procedures for determining whether a composition has a more sugar-like taste are well known in the art.

[0049] The compositions of the present invention may also further comprise at least one additional additive, such as a sweet taste improving composition, and/or a sweet taste improving additive. For example, the composition of the disclosure may comprise at least one sweet taste improving composition for balancing the temporal and/or flavor profile of the sweetness enhanced sweetener composition. The use of sweet taste improving compositions to improve the temporal and/or flavor profile of sweetener compositions are described in detail in U.S. Patent Application Publication Nos. 2007/0128311, 2007/0275147, 2008/0292765,

2011/0160311, and US 2011/0318464 the disclosures of which are incorporated herein by reference in their entirety. The disclosure of PCT/2017/021866 relates to certain esters of steviol glycosides which are suitable for use as sweeteners, for example, by incorporation into edible compositions and is incorporated herewith by reference.

[0050] Exemplary suitable sweet-taste improving compounds include, but are not limited to, carbohydrates, polyols, amino acids and their corresponding salts, poly- amino acids and their corresponding salts, sugar acids and their corresponding salts, nucleotides, organic acids, inorganic acids, organic salts including organic acid salts and organic base salts, inorganic salts, bitter compounds, flavorants and flavoring ingredients, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, flavonoids, alcohols, polymers, other sweet taste improving taste additives imparting such sugar-like characteristics, and

combinations thereof. In some embodiments, the sweet-taste improving compound is erythritol.

Useful concentrations of the sweeteners and sweet taste modulators as disclosed herein are between about 0.001 ppm and about 1000 ppm. In some embodiments between about 0.005 ppm to about 500 ppm; about 0.01 ppm to 25 about 100 ppm; about 0.05 ppm to about 50 ppm; about 0.1 ppm to about 5 ppm; about 0 .1 ppm to about 10 ppm; about 0. 1 ppm to about 100 ppm; about 1 ppm to about 10 ppm; about 1 ppm to about 30 ppm; about 1 ppm to about 50 ppm; about 10 ppm to about 20 ppm; about 10 ppm to about 25 ppm; about 10 ppm to about 30 ppm; about 1 ppm to about 50 ppm; about 5 ppm to about 50 ppm; about 30 ppm to about 50 ppm; about 30 ppm to about 50 ppm; about 1 ppm to about 60; ppm; about 100 ppm to about 300 ppm; about 100 ppm to about 1000 ppm; or about 30 ppm to about 3000 ppm; about 50 ppm to about 100 ppm; about 100 ppm to about 200 ppm; about 200 ppm to about 300 ppm; about 300 ppm to about 400 ppm; about 400 ppm to about 500 ppm; 10 about 500 ppm to about 600 ppm; about 600 ppm to about 700 ppm; about 700 ppm to about 800 ppm; about 800 ppm to about 900 ppm; about 900 ppm to aboutlOOO ppm; about 1000 ppm to about 1100 ppm; about 1100 ppm to about 1200 ppm; about 1200 ppm to about 1300 ppm; about 1300 ppm to about 1400 ppm; about 1400 ppm to about 1500 ppm; about 1500 ppm to about 1600 ppm; about 1600 ppm to about 1700 ppm; about 1700 ppm to about 1800 ppm; about 1800 ppm to about 1900 ppm; about 1900 ppm to about 2000 ppm; about 2000 ppm to about 2100 ppm; about 2100 ppm to about 2200 ppm; about 2200 ppm to about 2300 ppm; about 2300 ppm to about 2400 ppm; about 2400 ppm to about 2500 ppm; about 2500 ppm to about 2600 ppm; about 2600 ppm to about 2700 ppm; 20 about 2700 ppm to about 2800 ppm; about 2800 ppm to about 2900 ppm, or about 2900 ppm to about 3000 ppm. [0051] Suitable sweet taste improving amino acid additives for use in embodiments of this disclosure include, but are not limited to, aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid (α-, β-, or γ-isomers), glutamine, hydroxyproline, taurine, norvaline, sarcosine, and their salt forms such as sodium or potassium salts or acid salts. The sweet taste improving amino acid additives also may be in the D- or L-configuration and in the mono-, di-, or tri- form of the same or different amino acids. Additionally, the amino acids may be α-, β-, γ-, δ-, and ε-isomers if appropriate. Combinations of the foregoing amino acids and their corresponding salts (e.g., sodium, potassium, calcium, magnesium salts or other alkali or alkaline earth metal salts thereof, or acid salts) also are suitable sweet taste improving additives in some embodiments. The amino acids may be natural or synthetic. The amino acids also may be modified. Modified amino acids refers to any amino acid wherein at least one atom has been added, removed, substituted, or combinations thereof (e.g., N-alkyl amino acid, N-acyl amino acid, or N-methyl amino acid). Non-limiting examples of modified amino acids include amino acid derivatives such as trimethyl glycine, N-methyl -glycine, and N-methyl-alanine. As used herein, modified amino acids encompass both modified and unmodified amino acids. As used herein, amino acids also encompass both peptides and polypeptides (e.g., dipeptides, tripeptides, tetrapeptides, and pentapeptides) such as glutathione and L-alanyl-L-glutamine. Suitable sweet taste improving polyamino acid additives include poly-L-aspartic acid, poly-L-lysine (e.g., poly-L-a-lysine or poly-L-8-lysine), poly-L-ornithine (e.g., poly-L-a-ornithine or poly-L-8-ornithine), poly-L-arginine, other polymeric forms of amino acids, and salt forms thereof (e.g., calcium, potassium, sodium, or magnesium salts such as L-glutamic acid mono sodium salt). The sweet taste improving poly-amino acid additives also may be in the D- or L-configuration. Additionally, the poly-amino acids may be α-, β-, γ-, δ-, and ε-isomers if appropriate. Combinations of the foregoing poly-amino acids and their corresponding salts (e.g., sodium, potassium, calcium, magnesium salts or other alkali or alkaline earth metal salts thereof or acid salts) also are suitable sweet taste improving additives in some embodiments. The poly-amino acids described herein also may comprise co-polymers of different amino acids. The poly-amino acids may be natural or synthetic. The poly-amino acids also may be modified, such that at least one atom has been added, removed, substituted, or combinations thereof (e.g., N-alkyl poly-amino acid or N-acyl poly-amino acid). As used herein, poly- amino acids encompass both modified and unmodified poly-amino acids. For example, modified poly-amino acids include, but are not limited to poly-amino acids of various molecular weights (MW), such as poly-L-a-lysine with a MW of 1,500, MW of 6,000, MW of 25,200, MW of 63,000, MW of 83,000, or MW of 300,000. In some embodiments, the taste improving amino acid additive is glycine, alanine, taurine, serine or proline. In such embodiments, the taste improving amino acid additive is present in a concentration of about 10 ppm to about 25,000ppm or about 100 to about lOOOppm.

[0052] Suitable sweet taste improving sugar acid additives include, for example, but are not limited to aldonic, uronic, aldaric, alginic, gluconic, glucuronic, glucaric, galactaric, galacturonic, and salts thereof (e.g., sodium, potassium, calcium, magnesium salts or other physiologically acceptable salts), and combinations thereof.

[0053] For example, suitable sweet taste improving nucleotide additives include, but are not limited to, inosine monophosphate ("IMP"), guanosine monophosphate ("GMP"), adenosine monophosphate ("AMP"), cytosine monophosphate ("CMP"), uracil monophosphate ("UMP"), inosine diphosphate, guanosine diphosphate, adenosine diphosphate, cytosine diphosphate, uracil diphosphate, inosine triphosphate, guanosine triphosphate, adenosine triphosphate, cytosine

triphosphate, uracil triphosphate, alkali or alkaline earth metal salts thereof, and combinations thereof. The nucleotides described herein also may comprise nucleoti de-related additives, such as nucleosides or nucleic acid bases (e.g., guanine, cytosine, adenine, thymine, uracil).

[0054] Suitable sweet taste improving organic acid additives include any compound which comprises a— COOH moiety. Suitable sweet taste improving organic acid additives, for example, include but are not limited to C2-C 30 carboxylic acids, substituted hydroxyl C2-C30 carboxylic acids, benzoic acid, substituted benzoic acids (e.g., 2,4-dihydroxybenzoic acid), substituted cinnamic acids, hydroxyacids, substituted hydroxybenzoic acids, substituted cyclohexyl carboxylic acids, tannic acid, lactic acid, tartaric acid, citric acid, gluconic acid, glucoheptonic acids, adipic acid, hydroxy citric acid, malic acid, fruitaric acid (a blend of malic, fumaric, and tartaric acids), fumaric acid, maleic acid, succinic acid, chlorogenic acid, salicylic acid, creatine, caffeic acid, bile acids, acetic acid, ascorbic acid, alginic acid, erythorbic acid, polyglutamic acid, glucono delta lactone, and their alkali or alkaline earth metal salt derivatives thereof. In addition, the organic acid additives also may be in either the D- or L-configuration.

[0055] For example, suitable sweet taste improving organic acid additive salts include, but are not limited to, sodium, calcium, potassium, and magnesium salts of all organic acids, such as salts of citric acid, malic acid, tartaric acid, fumaric acid, lactic acid (e.g., sodium lactate), alginic acid (e.g., sodium alginate), ascorbic acid (e.g., sodium ascorbate), benzoic acid (e.g., sodium benzoate or potassium benzoate), and adipic acid. The examples of the sweet taste improving organic acid additives described optionally may be substituted with at least one group chosen from hydrogen, alkyl, alkenyl, alkynyl, halo, haloalkyl, carboxyl, acyl, acyloxy, amino, amido, carboxyl derivatives, alkylamino, dialkylamino, arylamino, alkoxy, aryloxy, nitro, cyano, sulfo, thiol, imine, sulfonyl, sulfenyl, sulfinyl, sulfamyl, carboxalkoxy, carboxamido, phosphonyl, phosphinyl, phosphoryl, phosphino, thioester, thioether, anhydride, oximino, hydrazino, carbamyl, phospho, phosphonato, and any other viable functional group provided the substituted organic acid additives function to improve the sweet taste of a synthetic sweetener.

[0071] Some aspects of the present disclosure include edible compositions, such as beverage compositions, concentrates (for use in, e.g., beverage compositions), food products, pharmaceutical preparations and table-top sweeteners comprising the compositions of the present disclosure; methods for preparing an edible composition; methods for reducing the amount of a sweetener in an edible composition; methods for reducing caloric intake; methods of enhancing activation of a sweet taste receptor. [0056] The esters of this invention can be isolated and purified and then used (e.g. added to a food, beverage or pharmaceutical preparation) or instead can be used as part of a reaction mixture or crude form.

[0057] Some embodiments of the present disclosure include a method of improving at least one sensorial characteristic of a sweetener, the method comprising esterif ing one or more hydroxyl groups of such sweetener.

[0058] Some embodiments of the present disclosure include a method comprising esterifying one or more hydroxyl groups of a sweetener, wherein at least one sensorial characteristic of the sweetener is improved, compared to a sweetener that is not esterified at at least one hydroxyl group.

[0059] In some embodiments the method disclosed herein comprises esterifying at least one hydroxyl group of a sweetener as disclosed herein.

[0076] In some embodiments the sensorial characteristic of a sweetener is selected from: improved taste, improved temporal profile, faster onset of perception of sweetness, reduced lingering of sweet taste, reduction in bitterness, reduction of licorice taste, and increased potency of sweetness.

[0077] In some embodiments a method of improving at least one sensorial characteristic of a sweet taste modulator comprising the esterification of one or more hydroxyl groups on such sweet taste modulator.

[0078] In some embodiments a method of improving one or more sensorial characteristic of a sweet taste modulator comprising the esterification of one or more hydroxyl groups on such sweet taste modulator.

[0079] In some embodiments a method of improving two or more sensorial characteristic of a sweet taste modulator comprising the esterification of one or more hydroxyl groups on such sweet taste modulator.

[0080] In some embodiments a method of improving one or more sensorial characteristic of a sweet taste modulator comprising the esterification of at least one hydroxyl groups on such sweet taste modulator.

[0081] In some embodiments a method of improving one or more sensorial characteristic of a sweet taste modulator comprising the esterification of two or more hydroxyl groups on such sweet taste modulator. [0082] In some embodiments the sensorial characteristic of a sweet taste modulator is selected from: improved taste, improved temporal profile, faster onset of perception of sweetness, and increased degree of sweet taste enhancement, of a sweetener.

[0083] In some embodiments the sensorial characteristic of a sweet taste modulator is selected from: improved taste, improved temporal profile, and faster onset of perception of sweetness.

[0084] In some embodiments the sweet taste modulator improves at least one sensorial characteristic selected from: improved taste, improved temporal profile, and faster onset of perception of sweetness without an increased degree of sweet taste enhancement.

[0085] In some embodiments a method of improving the taste of a sweetener comprising esterif ing one or more hydroxyl groups of such sweetener.

In some embodiments a method of improving the temporal profile of a sweetener esterified at one or more hydroxyl groups.

[0086] In some embodiments a method wherein the onset of the perception of sweetness from a sweetener esterified at one or more hydroxyl groups is more rapid.

[0087] In some embodiments a method wherein the linger of sweet taste from a sweetener esterified at one or more hydroxyl groups is diminished.

In some embodiments a method for reducing the bitterness of a sweetener, the method comprising esterifying said sweetener at one or more of its hydroxyl groups.

[0088] In some embodiments a method for reducing the licorice taste of a sweeter, the method comprising esterifying said sweetener at one or more of its hydroxyl groups.

[0089] In some embodiments a method of increasing potency of sweetness of a sweetener, the method comprising esterifying said sweetener at one or more of its hydroxyl groups.

[0090] In some embodiments a method of improving the taste of a sweet taste modulator, the method comprising esterifying said sweet taste modulator at one or more hydroxyl groups on said sweet taste modulator. [0091] In some embodiments a method of improving temporal profile of a sweet taste modulator, the method comprising esterifying said sweet taste modulator at one or more of its hydroxyl groups.

[0092] In some embodiments a method of reducing the time of perception of sweetness of a sweet taste modulator, the method comprising esterifying said sweet taste modulator at one or more of its hydroxyl groups.

[0093] In some embodiments a method of increasing enhancement of sweetness of a sweet taste modulator, the method comprising esterifying said sweet taste modulator at one or more of its hydroxyl groups. In some embodiments a method of improving at least one sensorial characteristic of an esterified sweetener or esterified sweet taste modulator, wherein the sensorial characteristic is selected from: improved taste, improved temporal profile, faster onset of perception of sweetness, reduced lingering of sweet taste, reduction in bitterness, reduction of licorice taste, reduction in metallic taste, reduction in astringent taste and increased potency of sweetness.

[0094] In some embodiments a method of improving the taste of a food, beverage, pharmaceutical composition or consumer product comprising adding an effective amount of an esterified sweetener, esterified sweet taste modulator or a

combination thereof to such food, beverage, pharmaceutical composition or consumer product.

[0095] In some embodiments a method the esterified sweetener, esterified sweet taste modulator or a combination thereof are added in their pure form.

[0096] In some embodiments a method the esterified sweetener, esterified sweet taste modulator or a combination thereof are added in their crude form or as part of a reaction mixture.

[0097] In some embodiments the esterified sweetener, esterified sweet taste modulator or a combination thereof comprises an extract.

[0098] In some embodiments the esterified sweetener, esterified sweet taste modulator or a combination thereof is added in form of an extract.

[0099] In some embodiments the sweetener as disclosed herein is a high potency sweetener. [0100] In some embodiments the high potency sweetener is a natural high potency sweetener.

[0101] In some embodiments the natural high potency sweetener is steviol glycoside, rebaudioside A, rebaudioside B, rebaudioside C (dulcoside B), rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M, dulcoside A, rubusoside, stevia leaf extract, stevioside, glycosylated steviol glycosides, mogrosides, mogroside V, isomogroside, mogroside IV, Luo Han Guo fruit extract, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hemandulcin, phyllodulcin, glycyphyllin, phloridzin, tnlobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, or cyclocarioside I or mixtures thereof.

[0102] In some embodiments the natural high potency sweetener is rebaudioside M, rebaudioside A or stevioside.

[0103] In some embodiments the natural high potency sweetener is a mogroside.

[0104] In some embodiments the sweetener is a synthetic high potency sweetener.

[0105] In some embodiments the synthetic high potency sweetener is sucralose, acesulfame potassium or other salts, aspartame, alitame, saccharin, neohesperidin dihydrochalcone, cyclamate, neotame, or advantame, or mixtures thereof.

[0106] In some embodiments a composition comprising an esterified sweetener or an esterified sweet taste modulator, or combinations thereof, or comestibly or biologically acceptable salts or derivatives thereof, wherein said composition is edible and capable of improving the sweet taste of a sweetener.

[0107] In some embodiments a composition wherein the esterified sweetener or esterified sweet taste modulator is present in one or more natural extracts.

[0108] In some embodiments a composition wherein the composition further comprises a sweetener.

[0109] In some embodiments a composition wherein the composition further comprises a solubilizing agent. [0110] In some embodiments a composition wherein the sweetener is a caloric sweetener, an artificial sweetener, a natural high-potency sweetener, or

combinations thereof.

[0111] In some embodiments a composition, wherein the caloric sweetener is a carbohydrate selected from sucrose, high fructose corn or starch syrup, glucose and fructose.

[0112] In some embodiments a composition wherein the caloric sweetener is high fructose corn or starch syrup.

[0113] In some embodiments a composition wherein the caloric sweetener is sucrose.

[0114] In some embodiments a composition wherein the caloric sweetener is a polyol selected from erythritol, sorbitol, mannitol and xylitol.

[0115] In some embodiments a composition, wherein the artificial sweetener is sucralose, acesulfame potassium or other salts, aspartame, alitame, sodium or calcium salt of saccharin, neohesperidin dihydrochalcone, sodium cyclamate, neotame, advantame, and salts thereof.

[0116] In some embodiments a composition, wherein the natural high-potency sweetener is steviol glycoside, rebaudioside A, rebaudioside B, rebaudioside C (dulcoside B), rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, Rebaudioside M, dulcoside A, rubusoside, stevia leaf extract, stevioside, glycosylated steviol glycosides, mogroside V, isomogroside, mogroside IV, Luo Han Guo fruit extract, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, or cyclocarioside I and mixtures thereof.

[0117] In some embodiments method of preparing an edible composition comprising, providing a comestibly acceptable carrier; and adding to said comestibly acceptable carrier a esterified sweetener, esterified sweet taste modulator or a combination of the foregoing. [0118] In some embodiments a composition wherein said composition is a beverage selected from the group consisting of a non-carbonated beverage, carbonated beverage, cola, root beer, fruit flavored beverage, citrus-flavored beverage, fruit juice, fruit-containing beverage, vegetable juice, vegetable containing beverage, tea, coffee, dairy beverage, sports drinks, energy drinks, enhanced and flavored water.

[0119] In some embodiments a composition, wherein the composition is used in food, beverage products, pharmaceutical compositions, nutritional products, functional products, a dietary supplement, over-the-counter medications, or oral care products.

[0120] In some embodiments a tabletop sweetener composition comprising an esterified sweetener or esterified sweet taste modulator or a combination thereof.

[0121] In some embodiments a tabletop sweetener composition, further comprising at least one bulking agent, additive, anti-caking agent, functional ingredient and combinations thereof.

[0121] In some embodiments a tabletop sweetener composition, wherein the tabletop sweetener composition is in the form of a liquid.

[0122] In some embodiments a composition as disclosed herein, wherein the food or beverage product is selected from the group consisting of soup, powdered soft drinks, bakery products, chewing gums, confections, cereals, edible gels, jams and jellys, spreads, ketchup, dairy products, frozen dairy products, gelatins/puddings, ice-creams.

[0123] In some embodiments a composition, wherein the composition is a beverage.

[0124] In some embodiments, the sweet taste modulator is a compound according to Formula I:

or comestibly or biologically acceptable salts or derivatives thereof, wherein: Rl, R2, R3, R4 are each independently methyl, ethyl, hydroxyl, methoxy, ethoxy or hydrogen and at least one R in the formula is a hydroxyl group.

[0125] In some embodiments, the sweet taste modulator is a compound according to Formula II:

or comestibly or biologically acceptable salts or derivatives thereof, wherein: Rl, R2, R3, R4 are each independently methyl, ethyl, hydroxyl, methoxy, ethoxy or hydrogen and least one R in the formula is a hydroxyl group.

[0126] In some embodiments, the esterified sweet taste modulator is selected from any one of Compounds 2, 4, or 6:

[0126] In some embodiments, the sweet taste modulator is a compound selected a compound according to Formula I, Formula II, or any one of compounds 2, 4, or 6, or a combination of the foregoing.

[0127] In some embodiments, the sweet taste modulator is a compound selected a compound according to Formula I, Formula II, or any one of compounds 2, 4, or 6, or a combination of the foregoing, wherein the esterified sweetener is present in one or more natural extracts.

[0128] In some embodiments, the sweet taste modulator is a compound selected a compound according to Formula I, Formula II, or any one of compounds 2, 4, or 6, or a combination of the foregoing, wherein the compound is isolated and purified.

Edible compositions

[0129] According to one aspect, the invention provides an edible composition comprising an esterified sweetener or an esterified sweet taste modulator of the invention or a combination of the foregoing.

[0130] The terms "edible composition," "orally ingestible composition" and "sweetenable composition" are used interchangeably, herein, and refer to a composition suitable for consumption, typically via the oral cavity (although consumption may occur via non-oral means such as inhalation). Edible compositions may be present in any form including, but not limited to, liquids, solids, semi-solids, tablets, lozenges, powders, gels, gums, pastes, slurries, syrups, aerosols and sprays. As used herein, edible compositions include food products, pharmaceutical compositions, and consumer products. The term edible composition also refers to, for example, dietary and nutritional supplements. As used herein, edible compositions also include compositions that are placed within the oral cavity but not swallowed, including professional dental products, such as dental treatments, fillings, packing materials, molds and polishes. The term "comestible" refers to similar compositions and is generally used as a synonym to the term "edible."

[0131] The term "food product" refers to any composition comprising one or more processed foodstuffs. Food products include, but are not limited to, confectionaries, bakery products (including, but not limited to, doughs, breads, biscuits, crackers, cakes, pastries, pies, tarts, quiches, and cookies), ice creams (including but not limited to impulse ice cream, take-home ice cream, frozen yogurt, gelato, sorbet, sherbet and soy, oat, bean and rice-based ice cream), dairy products (including, but not limited to, drinking milk, cheese, yogurt, and sour milk drinks), cheeses (including, but not limited to, natural cheeses and processed cheeses), butter, margarine, sweet and savory snacks (including but not limited to fruit snacks, chips/crisps, tortilla/corn chips, popcorn, pretzels, chocolates, and nuts), hot and cold beverages (including, but not limited to, beverages, beverage mixes, concentrates, juices, carbonated beverages, non-carbonated beverages, alcoholic beverages, non-alcoholic beverages, soft drinks, sports drinks, isotonic drinks, coffees, teas, bottled waters, and beverages prepared from botanicals and botanical extracts (including cold beverages that are prepared with botanical or fungi extracts as ingredients, and drinks that are prepared in various ways, such as infusions, decoctions, or other means of extraction or distillation of various plant parts, including, but not limited to leaves, flowers, stems, fruits, roots, rhizomes, stems, bark, volatile oils, or even the whole plant), snack bars (including, but not limited to granola bars, muesli bars, protein bars, breakfast bars, energy bars, and fruit bars), meal replacement products, ready meals (including, but not limited to canned meals, preserved meals, frozen meals, dried meals, chilled meals, dinner mixes, macaroni and cheese, frozen pizza, chilled pizza, and prepared salads), soups (including but not limited to broth-like soups and cream-based soups), broth, gravy, soy sauce, meats and fish (including raw, cooked, and dried meats), deli products (including but not limited to meats and cheeses suitable for slicing or pre- sliced meats and cheeses, e.g., turkey, chicken, ham, bologna, salami, bierwurst, capicola, chorizo, corned beef, dutch loaf, Serrano, prosciutto, head cheese, liverwurst, meatloaf (including olive loaf, pepper loaf, pimento loaf, and ham and cheese loaf), mortadella, pastrami, pepperoni, roast beef, roast pork, saucisson, smoked meat, summer sausage, tongue, American cheese, blue cheese, cheddar cheese, Colby cheese, Colby- Jack cheese, gouda, Monterey Jack cheese, muenster cheese mozzarella, parmigiano cheese, pepper jack cheese, provolone, romano cheese, string cheese, spray cheese, and swiss cheese), vegetables (including, but not limited to, raw, pickled, cooked, and dried vegetables, such as firench fries), fruits (including raw, cooked, and dried fruits), grains (including, but not limited to, dried cereals and breads), prepared foods (including, but not limited to, dried, canned, or jarred sauces and soups), snack foods, pastas (including, but not limited to, fresh pasta, chilled pasta, frozen pasta, dried pasta, and macaroni), noodles (including, but not limited to, egg noodles, wheat noodles, rice noodles, mung bean noodles, potato noodles, buckwheat noodles, corn noodles, cellophane noodles, chow mein, fettuccini, fusilli, gnocchi, lasagna, linguini, lo mein, macaroni, manicotti, pad thai, penne, ramen, rice vermicelli, rigatoni, soba, spaghetti, spatzle, udon, and ziti), canned foods, frozen foods, dried foods, chilled foods, oils and fats, baby food, spreads, salads, cereals (including, but not limited to, hot and cold cereals), sauces (including, but not limited to, cheese sauces (e.g., for macaroni and cheese) tomato pastes, tomato purees, bouillon cubes, stock cubes, table sauces, boys bases sauces, pasta sauces, cooking sauces, marinades, dry sauces, powder mixes, ketchups, mayonnaises, salad dressings, vinaigrettes, mustards, and dips), jellies, jams, preserves, honey, puddings, recipe mixes, syrups, icings, fillings, infused foods, salt-preserved food, marinated foods and condiments (such as ketchup, mustard and steak sauce). In some embodiments, the food product is animal feed. For example, the food product may be a pet food product, i.e. a food product for consumption by a household pet. In other embodiments, the food product is a livestock food product, i.e. a food product for consumption by livestock.

[0132] The term "foodstuff refers to an unprocessed ingredient or a basic nutrient or flavor containing element used to prepare a food product. Non-limiting examples of foodstuffs include: fruits, vegetables, meats, fishes, grains, milks, eggs, tubers, sugars, sweeteners, oils, herbs, snacks, sauces, spices and salts.

[0133] The term "processed foodstuff refers to a foodstuff has been subjected to any process which alters its original state (excluding, e.g., harvesting, slaughtering, and cleaning). Examples of methods of processing foods include, but are not limited to, removal of unwanted outer layers, such as potato peeling or the skinning of peaches; chopping or slicing; mincing or macerating; liquefaction, such as to produce fruit juice; fermentation (e.g. beer); emulsification; cooking, such as boiling, broiling, frying, heating, steaming or grilling; deep frying; baking; mixing; addition of gas such as air entrainment for bread or gasification of soft drinks; proofing; seasoning (with, e.g., herbs, spices, salts); spray drying; pasteurization; packaging (e.g., canning or boxing); extrusion; puffing; blending; and preservation (e.g., adding salt, sugar, potassium lactate or other preservatives).

[0134] The term "consumer product" refers to health and beauty products for the personal use and/or consumption by a subject. Consumer products may be present in any form including, but not limited to, liquids, solids, semi-solids, tablets, capsules, lozenges, strips, powders, gels, gums, pastes, slurries, syrups, aerosols and sprays. Non-limiting examples of consumer products include nutriceuticals, nutritional supplements, lipsticks, lip balms, soaps, shampoos, gums, adhesives (e.g., dental adhesives), toothpastes, oral analgesics, breath fresheners,

mouthwashes, tooth whiteners, and other dentifrices.

[0135] The term "combinations thereof as used herein refers to all permutations and combinations of the listed items preceding the term. For example, "A, B, C, or combinations thereof is intended to include at least one of: A, B, C, AB, AC, BC, or ABC, and if order is important in a particular context, also BA, CA, CB, CBA, BCA, ACB, BAC, or CAB. Continuing with this example, expressly included are combinations that contain repeats of one or more item or term, such as BB, AAA, AB, BBC, AAABCCCC, CBBAAA, CABABB, and so forth. The skilled artisan will understand that typically there is no limit on the number of items or terms in any combination, unless otherwise apparent from the context.

[0136] In some embodiments, the edible composition naturally or inherently comprises a sweetener. For example, the sweetener may be an inherent component of a food product or of a food stuff, such as fruit or a fruit product (e.g., fruit sauce). Accordingly, the esterified sweeteners, esterified sweet taste modulators or combinations of the foregoing of the present invention may be added to edible compositions to which no other sweetener is added.

[0137] Non-limiting examples of suitable carbohydrates include

monosaccharides, disaccharides, oligosaccharides, complex polysaccharides or combinations thereof. Non-limiting examples of suitable types of

monosaccharides for use in particular embodiments include trioses, tetroses, pentoses, hexoses, heptoses, octoses, and nonoses. Non-limiting examples of specific types of suitable monosaccharides include glyceraldehyde,

dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, xylose, ribulose, xylulose, allose, altrose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose,

sedoheltulose, octolose, and sialose. Non-limiting examples of suitable

disaccharides include sucrose, lactose, and maltose. Non-limiting examples of suitable oligosaccharides include saccharose, maltotriose, and maltodextrin. In other particular embodiments, the carbohydrates are provided by a corn syrup, a beet sugar, a cane sugar, a juice, or a tea.

[0138] The amount of both an esterified sweet taste modulating compound of the present invention and an esterified sweetener used in an edible composition depends upon a variety of factors, including the purpose of the composition and the desired or acceptable perception of sweetness. The amount may depend on the nature of the edible composition, the particular compound added, the sweetener, other compounds present in the composition, the method of preparation (including amount of heat used), and the pH of the edible composition. Those of skill in the art will know how to determine the amounts needed to produce the desired taste(s).

[0139] In some embodiments, the edible compositions are formulated as a concentrate, which is intended for dilution prior to consumption. Such

concentrates include syrups, frozen concentrates, dry mixes, and food additives. When present in a concentrate, the esterified sweeteners or esterified sweet taste modulating compounds or combinations thereof are present at a concentration about 2-fold, about 3-fold, about 4-fold, about 5-fold, about 6-fold, about 7-fold, about 8-fold, about 9-fold, about 10-fold, about 15-fold, about 20-fold, about 25- fold, about 30-fold, about 35-fold, about 40-fold, about 45-fold, about 50-fold, about 55-fold, about 60-fold, about 65-fold, about 70-fold, about 75-fold, about 80- fold, about 85-fold, about 90-fold, about 95-fold, about 100-fold, about 150-fold, about 200-fold, about 250-fold, about 300-fold, about 350-fold, about 400-fold, about 450-fold, about 500-fold, about 550-fold, about 600-fold, about 650-fold, about 700-fold, about 750-fold, about 800-fold, about 850-fold, about 900-fold, about 950-fold, or about 1000-fold above any of the effective concentrations discussed herein.

[0140] Preferred auxiliaries or carriers include maltodextrin, starch, natural or artificial polysaccharides and/or vegetable gums such as modified starches or gum arabic, coloring agents, for example permitted foodstuff dyes, coloring plant extracts, stabilizers, preservatives, antioxidants, viscosity-influencing substances

[0141] The edible compositions may be included in a package. Optionally, the edible composition is packaged in bulk, in which the package contains more of the compositions than would typically be used for a single dish or serving of food or beverage. Such bulk packages can be in the form of paper, plastic, or cloth bags or cardboard boxes or drums. Such bulk packages may be fitted with plastic or metal spouts to facilitate the dispensing of the edible composition.

[0142] The package may contain an edible composition comprising an esterified sweetener or esterified sweet taste modulating compound of the present invention and a sweetener. In some embodiments, the package contains an edible

composition comprising an esterified sweetener or an esterified sweet taste modulating compound (or a combination of the foregoing) of the present invention and caloric carbohydrate sweetener. In some embodiments, the package contains an edible composition comprising a sweet taste modulating compound of the present invention and glucose, fructose, sucrose, or a mixture thereof. In some embodiments, the package contains an edible composition comprising an esterified sweetener or an esterified sweet taste modulating (or a combination of the foregoing) compound and a synthetic sweetener. In some embodiments, the package contains an edible composition comprising an esterified sweetener or an esterified sweet taste modulating compound (or a combination of the foregoing) and a natural high-potency sweetener.

[0143] The edible compositions may be used for medicinal or hygienic purposes, for example, in mouthwash, medicines, pharmaceuticals, cough syrup, throat spray, toothpaste, dental adhesives, tooth whiteners, glues (e.g., on stamps and

envelopes), and toxins used in insect and rodent control.

[0144] In some embodiments of the disclosure, the sweetener composition is in a form of a tabletop sweetener composition comprising at least one esterified sweetener or esterified sweet taste modulator or combinations thereof, at least one sweetener, and at least one bulking agent and optionally at least an anti -caking agent.

[0145] For example, suitable "bulking agents" include, but are not limited to maltodextrin (10 DE, 18 DE, or 5 DE), corn syrup solids (20 or 36 DE), sucrose, fructose, glucose, invert sugar, sorbitol, xylose, ribulose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharides, cellulose and cellulose derivatives, and mixtures thereof. Additionally, the at least one bulking agent is chosen from, granulated sugar (sucrose) or other caloric sweeteners such as crystalline fructose, other carbohydrates, and sugar alcohols. In one embodiment, a bulking agent may be used as a sweet taste improving composition.

[0146] As used herein the phrase "anti-caking agent" is understood to mean any composition which prevents, reduces, inhibits, or suppresses at least one sweetener molecule from attaching, binding, or contacting to another sweetener molecule. Alternatively, "anti-caking agent" may refer to any composition which assists in content uniformity and uniform dissolution. In accordance with some

embodiments, non-limiting examples of anti-caking agents include cream of tartar, calcium silicate, silicon dioxide, microcrystalline cellulose (Avicel, FMC

BioPolymer, Philadelphia, Pa.), and tricalcium phosphate. In at least one embodiment, the anti-caking agents are present in the tabletop sweetener composition in an amount from about 0.001 to about 3% by weight of the tabletop sweetener composition.

[0147] Tabletop sweetener compositions may be embodied and packaged in numerous different forms, and may be of any form known in the art. For example, and not by way of limitation, the tabletop sweetener compositions may be in the form of powders, granules, packets, tablets, sachets, pellets, cubes, solids, or liquids.

Method of preparing an edible composition

[0060] According to another aspect, the invention provides a method of preparing an edible composition. The method comprises: (a) providing a sweetener; and (b) adding to the sweetener of (a) an esterified sweetener an esterified sweet taste modulator or combinations thereof. In some embodiments, the esterified sweetener or esterified sweet taste modulator of the invention has been solubilized prior to the addition step (b). In other embodiments, a

solubilizing agent is added to the composition. In some embodiments, the sweetener of step (a) is provided in a comestibly acceptable carrier. The skilled artisan will appreciate that method steps (a) and (b) can be performed in any order - i.e., the method may comprise: (a) adding an esterified sweetener or esterified sweet taste modulator as described herein, or combinations thereof; and (b) adding a sweetener to the Compound(s) of (a).

[0149] Methods for solubilizing compounds of the present invention include but are not limited to chemical, physical or mechanical means. Additives, solubilizing or stabilizing agents may provide chemical means for increasing the concentration of compounds of the present invention in solution. Application of mechanical forces resulting in shearing, dispersion or emulsification of compounds of the present invention may also result in an increase in the concentration of compounds of the present invention in solution. Changes in temperature, pressure, and/or pH are non-limiting physical means for increasing the solubility of compounds of the present invention and/or maintaining the concentration of the compound in solution. The mechanical, physical or chemical means may be used in

combination, in the presence or absence of cosolvents, surfactant systems, complexing agents and also including self-assembling nanomicelles,

nanosuspensions, micronization and cocrystallizations. The methods as well as the importance of increasing the solubility of compounds in solution are well known in the art, for example, "Drug solubility: importance and enhancement techniques", ISRN Pharmaceutics, volume 2012, article ID 195727, Ketan T. Savjani, Anuradha K. Gajjar and Jignasa K. Savjani.

[0150] Solubilizing agents include, but are not limited to, glycoprotein- polysaccharides, such as Gum Arabic; homopolymers, such as poly(N-vinyl- pyrrolidone); medium chain mono- and diglycerides, such as Capmul MCM;

oligosaccharides, such as Hp-beta-cyclodextrin, alpha-cyclodextrin, beta- cyclodextrin or gamma-cyclodextrin, and cellulose; polyglycerol esters, such as Caprol PEG 860 ^® , Caprol 10G40 ^® or Drewpol 10- 1 -CC ^® ; polysorbates, such as Tween 20 ^® (polysorbate 20), Tween 60 ^® (polysorbate 60), and Tween

80 ^® (polysorbate 80); and saponin/triterpene glycoside, such as quillaja saponin or Q-NATURALE ^® . For example, solubilizing agents include, but are not limited to, GRINDSTED ^® ACETEM, alpha-Cyclodextrin, beta-Cyclodextrin, DATEM, Decaglycerol dioleate, Decaglycerol monooleate, Decaglycerol monostearate,

Ethoxylated monoglyceride, gamma-Cyclodextrin, Glycerol monoleate, Glycerol monostearate, Glyerol dioleate, Gum Arabic, Hexaglycerol dioleate, Hp-beta- Cyclodextrin, Lecithin, Methyl cellulose, Oleic acid, Poly(N-vinyl-pyrrolidone), Polyoxyethylene (20) sorbitan monooleate, Polyoxyethylene (20) sorbitan monopalmitate, Polyoxyethylene (20) sorbitan monostearate, Polyoxyethylene (20) sorbitan trioleate, Polyoxyethylene (20) sorbitan tristearate, Polysaccharides, polysorbate 20, polysorbate 60, polysorbate 80, Potassium oleate, Propylene glycol monostearate, Propylene glycol monolaurate, Quillaja saponins, Sodium lauryl sulfate, Sodium oleate, Sodium stearoyllactylate, Sorbitan monolaurate, Sorbitan trioleate, Sorbitan tristearate, Sorbitan monooleate, Sorbitan monostearate, Sucrose monoester, or Sucrose monolaurate. In some embodiments, the solubilizing agent is alpha-Cyclodextrin, beta-Cyclodextrin, gamma-Cyclodextrin, Gum Arabic, Hp- beta-Cyclodextrin, Lecithin, Methyl cellulose, Poly(N-vinyl-pyrrolidone), or Quillaja saponins (Q-NATURALE ^® ). In some embodiments, the solubilizing agent is alpha-Cyclodextrin. In some embodiments, the solubilizing agent is beta- Cyclodextrin. In some embodiments, the solubilizing agent is gamma- Cyclodextrin. In some embodiments, the solubilizing agent is Gum Arabic. In some embodiments, the solubilizing agent is Hp-beta-Cyclodextrin. In some embodiments, the solubilizing agent is Lecithin. In some embodiments, the solubilizing agent is Methyl cellulose. In some embodiments, the solubilizing agent is Poly(N-vinyl-pyrrolidone). In some embodiments, the solubilizing agent is Quillaja saponins. Solubilizing agents may be used at concentrations between 0.001% to 50% to solubilize the compounds of the invention. In some

embodiments, concentrations of solubilizing agents in the final product range from about 0.05% to about 2%.

[0151] Solvents for dissolving the esterified sweeteners and esterified sweet taste modulators of the invention include, but are not limited to, 1,3-butylene glycol, amyl acetate, benzyl alcohol, butane-l,3-diol, castor oil, diethyl tartrate, diethylene glycol monoethyl ether, ethyl acetate, ethyl alcohol, glycerin, glycerol, glycerol diacetate, isopropyl alcohol, EOBEE ^® M-5 oil, propylene glycol, and triacetin. In some embodiments, the solvent is 1,3-butylene glycol. In some embodiments, the solvent is amyl acetate. In some embodiments, the solvent is benzyl alcohol. In some embodiments, the solvent is butane- 1, 3 -diol. In some embodiments, the solvent is castor oil. In some embodiments, the solvent is diethyl tartrate. In some embodiments, the solvent is diethylene glycol monoethyl ether. In some embodiments, the solvent is ethyl acetate. In some embodiments, the solvent is ethyl alcohol. In some embodiments, the solvent is glycerin. In some

embodiments, the solvent is glycerol. In some embodiments, the solvent is glycerol diacetate. In some embodiments, the solvent is isopropyl alcohol. In some embodiments, the solvent is propylene glycol. In some embodiments, the solvent is triacetin. Solvents may be used at concentrations between 0.001% to 50% to solubilize the compounds of the invention. In some embodiments, solvent concentrations in the final product range from about 0.05 to about 2%.

[0152] In general, the method of preparing an edible composition of the invention comprises mixing a component or ingredient of the edible composition, such as a sweetener, with an esterified sweetener, esterified sweet taste modulating compound of the invention or a combination thereof. Alternatively, an esterified sweetener or esterified sweet taste modulating compound (or a combination of thereof) of the invention can be added directly to an edible composition comprising a sweetener. In some embodiments, the sweetener is added to the edible composition simultaneously or sequentially with a sweet taste modulating compound of the invention. If sequentially, the sweetener may be added before or after the sweet taste modulating compound of the invention. When solubilizing agents are utilized, the method includes the addition of the solubilizing agent at any point. For example, if the composition compromises three components - the sweetener, the sweet taste modulating agent, and the solubilizing compound - the solubilizing compound may be added as the first, second, or third component. The solubilizing agent may also be added concurrently with any other component.

[0153] In some embodiments, the methods of preparing an edible composition further comprise adding at least one additional additive, such as a sweet taste improving composition, and/or a sweet taste improving additive.

[0154] The edible compositions may be a food product, a pharmaceutical composition, or a consumer product. In some embodiments, the edible

composition is in the form of, for example, a gum, lozenge, sauce, condiment, meat matrix, meat slurry, paste, suspension, spread, coating, a liquid, a gel, an emulsion, granules, or seasoning. Method of reducing the amount of a sweetener in an edible composition

[0155] It may be desirable to reduce the amount of a caloric sweetener in an edible composition to reduce the calorie content of that edible composition. It may also be desirable to decrease the amount of a synthetic sweetener or a non-natural high potency sweetener in an edible composition to decrease an undesirable taste or aftertaste associated with the synthetic sweetener or non-natural high potency sweetener. Accordingly, another aspect of the present invention provides a method of reducing the amount of a sweetener in an edible composition, such as a food product, a pharmaceutical composition or a consumer product. An amount of the sweetener in the edible composition may be replaced with an esterified sweetener or esterified sweet taste modulator, or combinations thereof. In such methods, an amount of solubilizing agent may also be added to the edible composition, as described herein.

[0156] The term "replace" or "replacing" refers to substituting one compound for another compound in or in the preparation of, for example, an edible composition, such as food product. It includes complete and partial replacements or

substitutions.

[0157] In some embodiments, the method of reducing the amount of a sweetener in an edible composition comprises the steps of: (a) ingesting a first edible composition, in which the amount of a sweetener has been reduced; and (b) ingesting a second edible compound, which comprises an esterified sweet taste modulator compound of the present invention. In some embodiments, the first edible composition is ingested before the second edible composition. In some embodiments, the first edible composition is ingested after the second edible composition. In some embodiments, the first edible composition is ingested concurrently with the second edible composition. In such methods, an amount of solubilizing agent may also be added along with the sweet taste modulator of the present invention.

[0158] In some embodiments, the edible composition is a food product. In some embodiments, the edible composition is a pharmaceutical composition. In some embodiments, the edible composition is a consumer product. The sweetener being replaced may be a natural caloric sweetener, a natural high-potency sweetener, a synthetic sweetener, or combinations thereof. When the sweetener being replaced is a natural caloric sweetener, the sweetener may be sucrose, fructose, glucose, erythritol, high fructose corn/starch syrup, and mixtures thereof. When the sweetener being replaced is a synthetic sweetener, the sweetener may be sucralose, aspartame, potassium acesulfame, and mixtures thereof. The method also comprises replacing an amount of a natural caloric sweetener with an esterified synthetic or natural high-potency sweetener and, optionally an esterified sweet modulating compound of the present invention, such that any off-taste or after taste associated with the synthetic or natural high-potency sweetener is reduced or eliminated. In such embodiments, the "sweetener replaced" is the natural caloric sweetener.

[0159] In some embodiments, the methods of reducing sugar intake of a subject further comprise the step of identifying a subject in need thereof. The skilled worker would be able to identify a subject in need of reducing sugar intake. Non- limiting examples of such subjects include subjects that suffer from any one or more of the following disorders: diabetes, pre-diabetes, insulin resistance, obesity, excessive weight, and hyperglycemia.

[0160] In some embodiments, the amount of the sweetener replaced in the edible composition in step (a) is an amount sufficient to maintain or restore the health of a subject. For example, the amount of the sweetener replaced in the edible composition may be an amount sufficient to decrease diabetes, pre-diabetes, insulin resistance, obesity, excessive weight, and hyperglycemia in a subject. The amount of the sweetener replaced may be up to 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70% 75%, 80%, 85%, 90%, 95% or 99%. These amounts are not meant to be limiting, and increments between the recited percentages are specifically envisioned as part of the invention.

[0161] In some embodiments, the method of reducing the amount of a sweetener in an edible composition further comprises adding at least one additional additive, such as a sweet taste improving composition, and/or a sweet taste improving additive. Method of reducing caloric intake

[0162] Another aspect of the invention provides a method of reducing caloric intake of a subject. In some embodiments, the method comprises the step of providing an edible composition to the subject, wherein all or a portion of a natural caloric sweetener in the edible composition is replaced with (a) an esterified sweetener or an esterified sweet taste modulating compound as described herein or combinations thereof. The edible composition may be a food product, a pharmaceutical composition, or a consumer product. In such methods, an amount of solubilizing agent may also be added to the edible composition, as described herein.

[0163] The methods of reducing caloric intake of a subject may further comprise the step of identifying a subject in need thereof. The skilled worker would be able to identify a subject in need of reducing sugar intake. Non-limiting examples of such subjects include subjects that suffer from any one or more of the following disorders: diabetes, pre-diabetes, insulin resistance, obesity, excessive weight, and hyperglycemia.

[0164] In some embodiments, the amount of the natural caloric sweetener replaced in the edible composition is an amount sufficient to maintain or restore the health of a subject. For example, the amount of the natural caloric sweetener replaced in the edible composition may be an amount sufficient to result in weight loss in a subject. Alternatively, the amount of the natural caloric sweetener replaced in the edible composition may be an amount sufficient to alleviate the effects of, or treat, a disease associated with sugar consumption or excessive weight of the subject (e.g., diabetes). In some embodiments, the amount of the natural caloric sweetener replaced in the edible composition is up to 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70% 75%, 80%, 85%, 90%, 95% or 99%. These amounts are not meant to be limiting, and increments between the recited percentages are specifically envisioned as part of the invention. In some embodiments, the present method results in the subject's daily natural caloric sweetener intake being less than 250 g/day, less than 200 g/day, less than 175 g/day, less than 150 g/day, less than 125 g/day, less than 100 g/day, less than 75 g/day, less than 50 g/day, less than 25 g/day, less than 20 g/day, less than 15 g/day, less than 10 g/day, or less than 25 g/day.

[0165] In some embodiments, the amount of esterified sweetener or esterified sweet taste modulator of the invention added to the edible composition is sufficient to permit reduction of a subject's natural caloric sweetener intake by up to 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70% 75%, 80%, 85%, 90%, 95% or 99%. These amounts are not meant to be limiting, and increments between the recited percentages are specifically envisioned as part of the invention. In some embodiments, the amount of sweet taste modulating compound of the invention added to the edible composition is sufficient to permit reduction of a subject's natural caloric sweetener intake by up to 25%. In other embodiments, the amount of sweet taste modulating compound of the invention added to the edible composition is sufficient to permit reduction of a subject's natural caloric sweetener intake by up to 50%. In other embodiments, the amount of sweet taste modulating compound of the invention added to the edible composition is sufficient to permit reduction of a subject's natural caloric sweetener intake by up to 75%. In yet other embodiments, the amount of sweet taste modulating compound of the invention added to the edible composition is sufficient to permit reduction of a subject's natural caloric sweetener intake by up to 99%.

[0166] In some embodiments, the method of reducing the amount of a sweetener in an edible composition further comprises adding at least one additional additive, such as a sweet taste improving composition, and/or a sweet taste improving additive. Method of enhancing activation of a sweet taste receptor

[0167] Another aspect of the invention provides a method of activating, enhancing or potentiating activation and/or signaling of a sweet taste receptor. In some embodiments, the method comprises contacting a sweet taste receptor with an esterified sweetener or esterified sweet taste modulator or combinations thereof.

[0168] In some embodiments, the method comprises contacting a sweet taste receptor with an edible composition comprising a esterified sweetener or esterified sweet taste modulator or combinations thereof. The edible composition may be a food product, a pharmaceutical composition, or a consumer product. In such methods, an amount of solubilizing agent may also be present in the edible composition, as described herein.

[0169] In various embodiments, the sweet taste receptor is an ex vivo or in vivo receptor present in, for example, an assay. The sweet taste receptor also may be an in vivo receptor present in a subject. In such embodiments, the sweet taste receptor is typically present in the oral cavity or gastrointestinal tract of the subject. In some embodiments, the sweet receptor is in the oral cavity of a human.

Alternatively, the sweet receptor is in the oral cavity of a non-human animal, such as an animal model.

[0170] An in vivo sweet responsive assay means an assay where an assessment of increased perception of sweetness can be ascribed. Such an assay may be, for example, but not limited to, a human sensory descriptive analysis panel, a human sensory discriminative panel, and/or an expert flavorist assessment. Non-human assessments of sweet response include, but not limited to, operant conditioned animal studies of sweetness taste perception and/or lick rate/amount bottle preference tests

[0171] An in vitro sweet responsive assay refers to an assay where an assessment of increased sweet response or interaction can be ascribed. An example of such an assay may be, but is not limited to, in vitro receptor binding assays, in vitro receptor cell-based assays, and/or electronic tongue taste analysis.

[0172] In some embodiments, enhancement of a sweet taste receptor activation will affect a physiological process or condition. Non-limiting examples of physiological processes and conditions affected by the enhancement of sweet taste receptor activation include sweet taste, effects on the gastrointestinal tract, appetite, nutrition, nutrient absorption, satiety, hunger, diabetes, obesity, blood glucose levels, blood glucose regulation, metabolism, diet, and eating disorders.

EXAMPLES Preparation of the Compounds of the Invention

[0173] Methods of preparing esters are well known in the art, and the following synthetic scheme is merely illustrative and should not be interpreted as limiting the scope of the invention. An ESI MS Spectrum of Reb M acetate is shown in Figure 1.

[0174] Reb M acetates synthesis: 0.2gram Reb M is dissolved in 20ml acetic acid. The solution is heated at 45°C for three days. The reaction mixture is dried under vacuum and then dissolved in DMSO, which is further subjected to a C18 column eluting with a solvent system of 30% acetonitrile and 70% water.

[0175] In order that this invention be more fully understood, the following example is set forth. The example is for the purpose of illustration only and not to be construed as limiting the scope of the invention in any way.

[0176] The test compounds used in the following example may be obtained from the synthetic methods disclosed above.

[0177] The taste test panelists used in Example 1, 2, 3 and 4 were selected using a sensory acuity screening program and then trained in descriptive analysis taste testing. Candidate panelists were recruited, with prescreening and personal interviews, and were assessed for their ability to detect, recognize and differentiate basic taste attributes or mixtures thereof as part of a standardized acuity test.

These candidate panelists were also assessed for their innate ability to identify flavors, and to rank on intensity scales. Other senses such as smell and vision were also included as part of the assessment. Candidates also were screened for their ability to use the language to describe and articulate ideas.

[0178] Due to the complex nature of taste perception in subjects and the inherently subjective nature of the following experiments, individual taste test trials may yield different results for a given compound. The data presented in the following Example is illustrative of the taste testing results observed.

Example 1

[0179] The method was performed as a double blinded, randomized test, where trained Descriptive Analysis taste panelists (n >12) profiled the sweetness maximum perceived intensity, at 18 seconds, of a Rebaudioside M control sample, as well as a Rebaudioside M Acetate Ester Mixture variant sample prepared in accordance with the above synthetic scheme, in pH4 aqueous buffer. Each panelist scored sweetness intensity on a 15 cm scale, with the control and variant sample being determined to be iso-sweet by ANOVA at 18 seconds. The panelists continued to assess sweetness intensity (at lmin30s, 3 min), as well as bitterness intensity (3 min, 4 min) to generate a discontinuous time scale intensity profile (TSI) of sweet and bitter percepts. The results of such assessment are set forth in Table 1. Both for sweetness and bitter, the lingering effects were significantly less by ANOVA in the Rebaudioside M - acetate ester reaction mixture variant sample, as compared to the Rebaudioside M control sample. Therefore the taste profile was seen to be improved.

Table 1. DA assessment of sweetness intensity and bitterness

Example 2

[0180] Preparation of Compound 2: R-4-(4-acetoxy-3-methoxyphenyl)-7- methyl-2-oxochroman-5-yl acetate

To a solution of mixture of R-5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7- methylchroman-2-one in DCM, acetic anhydride (2mmol) and triethyl amine (2mmol) were added. The reaction was stirring at 50°C for 2 hours and evaporated to dryness. The acylated product was purified by C18 reverse phase with 50% AcN in Water (0.1% formic acid). LC-MS. 385 (M+H). Figure 2 depicts a MR spectra of Compound 2.

[0181] Preparation of Samples for sensory taste tests

The aqueous solutions were prepared by adding appropriate levels of citric acid and sodium citrate to water to achieve a target pH of 4.0. Each aqueous sample also contained high fructose corn syrup (HFCS) in the range of 6.7%- 7.7%.

Control Sample: Compound 1 @ 20ppm in aqueous solution

Variant Sample: Compound 2 @ 20ppm in aqueous solution

Compounds, in both the control and variant samples, were solubilized, at the same concentration, directly in the aqueous solution at the desired test concentration.

[0182] Sensory Methodology:

The method was performed as a double blinded, randomized test, using trained Descriptive Analysis taste panelists (n >12). The panelists compared the maximum perceived intensity, at 18 seconds, of the control and the variant sample for the following 4 off-note attributes; bitterness, astringent, licorice and metallic.

Each panelist scored the intensity on a 15 cm scale. The results of such assessment are set forth in Figure 3. For all 4 attributes, the mean intensities were significantly less by ANOVA in the Compound 2 containing variant sample, compared to the Compound 1 containing control sample. Thereby indicating that the taste profile was improved with Compound 2.

Example 3

[0183] Preparation of Compound 4: mixture of 4-(4-acetoxy-3-methoxyphenyl)- 7-methyl-2-oxochroman-5-yl acetate and 4-(4-acetoxy-3-methoxyphenyl)-5- methyl-2-oxochroman-7-yl acetate.

To a solution of 7-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-5-methylchroman-2- one (0.5mmol) and 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methylchroman- 2-one (0.5mmol) in DCM, acetic anhydride (2mmol) and tri ethyl amine (2mmol) were added. The reaction was stirring at 50°C for 2hours and evaporated to dryness. The acylated product was purified by CI 8 reverse phase HPLC with 50% AcN in Water (0.1% formic acid). LC-MS. 385 (M+H). Figure 4 depicts a MR spectra of Compound 4. Preparation of Samples for sensory taste tests:

[0184] The aqueous solutions were prepared by adding appropriate levels of citric acid and sodium citrate to water to achieve a target pH of 4.0. Each aqueous sample also contained high fructose corn syrup (HFCS) in the range of 6.7%- 7.7%. Control Sample: Compound 3 @ 35ppm in aqueous solution

Variant Sample: Compound 4 @ 35ppm in aqueous solution

Compounds, in both the control and variant samples, were solubilized, at the same concentration, directly in the aqueous solution at the desired test concentration. Sensory Methodology:

[0185] The method was performed as a double blinded, randomized test, using trained Descriptive Analysis taste panelists (n >12). The panelists compared the maximum perceived intensity, at 18 seconds, of the control and the variant sample for the following 4 off-note attributes; bitterness, astringent, licorice and metallic. Each panelist scored the intensity on a 15 cm scale. The results of such assessment are set forth in Figure 5. For 3 of the 4 attributes, the mean intensities were significantly less by ANOVA in the Compound 4 containing variant sample, compared to the Compound 3 containing control sample. Thereby indicating that the taste profile was improved with Compound 4.

Example 4

Preparation of Compound 6

[0186] S-2-(3-acetoxy-4-methoxyphenyl)-8-methylchroman-7-yl acetate

To a solution of mixture of (S)-2-(3-hydroxy-4-methoxyphenyl)-8- methylchroman-7-ol (0.5mmol) in DCM, acetic anhydride (2mmol) and tri ethyl amine (2mmol) were added. The reaction was stirring at 50°C for 2hours and evaporated to dryness. The acylated product was purified by CI 8 reverse phase with 50% AcN in Water (0.1% formic acid). LC-MS. 371 (M+H). Figure 6 depicts a NMR spectra of Compound 6.

Preparation of Samples for sensory taste tests:

[0187] The aqueous solutions were prepared by adding appropriate levels of citric acid and sodium citrate to water to achieve a target pH of 4.0. Each aqueous sample also contained high fructose corn syrup (FIFCS) in the range of 6.7%- 7.7%.

Control Sample: Compound 5 @ 35ppm in aqueous solution

Variant Sample: Compound 6 @ 35ppm in aqueous solution

Compounds, in both the control and variant samples, were solubilized, at the same concentration, directly in the aqueous solution at the desired test concentration. Sensory Methodology:

[0188] The method was performed as a double blinded, randomized test, using trained Descriptive Analysis taste panelists (n >12). The panelists compared the maximum perceived intensity, at 18 seconds, of the control and the variant sample for the following 4 off-note attributes; bitterness, astringent, licorice and metallic. Each panelist scored the intensity on a 15 cm scale. The results of such assessment are set forth in Figure 7. For all 4 attributes, the mean intensities were significantly less by ANOVA in the Compound 6 containing variant sample, compared to the Compound 5 containing control sample. Thereby indicating that the taste profile was improved with Compound 6.

The unesterified and corresponding esterified compounds as exemplified in Examples 2-4 are listed below: