Dihydrochalcone compounds for enhancing alcohol perception

Abstract

The present disclosure generally relates to dihydrochalcone compounds and their use for enhancing the perception of alcohol (ethanol) in food, beverages, and other comestible compositions. In certain aspects, the disclosure provides the use of such dihydrochalcone compounds to enhance an alcoholic (ethanolic) flavor of a beverage, for example, a low-alcohol or zero-alcohol beverage. In certain other aspects, the disclosure provides low-alcohol or zero-alcohol beverages containing such dihydrochalcone compounds.

Description

[0001] DIHYDROCHALCONE COMPOUNDS FOR ENHANCING ALCOHOL PERCEPTION

[0002] TECHNICAL FIELD

[0003] The present disclosure generally relates to dihydrochalcone compounds and their use for enhancing the perception of alcohol (ethanol) in food, beverages, and other comestible compositions. In certain aspects, the disclosure provides the use of such dihydrochalcone compounds to enhance an alcoholic (ethanolic) flavor of a beverage, for example, a low-alcohol or zero-alcohol beverage. In certain other aspects, the disclosure provides low-alcohol or zero- alcohol beverages containing such dihydrochalcone compounds.

[0004] DESCRIPTION OF RELATED ART

[0005] Excessive ethanol (alcohol) consumption is a major public health concern throughout the world. Alcohol-related fatalities are one of the leading causes of death. Because alcohol tends to reduce inhibitions, people are more likely to engage in risky activities following the consumption of alcohol. Alcohol also places stress on the liver and can cause normal metabolic processes to slow. Thus, alcohol consumption frequently leads to weight gain and an overall increase in visceral fat, which contributes to the onset of various metabolic disorders, such as diabetes. Consistent alcohol consumption over many years can also lead to liver disease, which generally results in premature death. As people become more aware of the negative health impacts of alcohol consumption, there is an increasing demand for comparable beverages that are lower in alcohol or that lack alcohol altogether.

[0006] But alcohol in beverages imparts a variety of desirable organoleptic properties. For example, alcohol and certain byproducts of fermentation impart a desirable kokumi effect and tend to stimulate other taste receptors and ion channels in the mouth. And the presence of alcohol in beverages generally enhances the mouthfeel of the beverage. Thus, in many cases, low-alcohol or zero-alcohol beverages often lack the desirable organoleptic properties that consumers associate with standard alcoholic beverages. Such analogues often taste more like flavored seltzer than beer or a mixed drink. These deficiencies can be offset by the addition of sugars and other carbohydrates. But this increases the caloric content of the beverage and often leads to a beverage having a high glycemic load. This too contributes to weight gain and other metabolic disorders. Thus, the use of carbohydrates to compensate for the lack of alcohol is disfavored by many consumers today.

[0007] Therefore, there is a continuing need to discover compounds that, when added to zero- alcohol or low-alcohol beverages, impart the desirable organoleptic properties of alcohol without increased use of sugars or other carbohydrates. SUMMARY

[0008] The present disclosure relates to the discovery of certain flavoring compositions that enhance the perception of alcohol without using sugars or other caloric carbohydrates.

[0009] In a first aspect, the disclosure provides the use of a dihydrochalcone compound disclosed herein to enhance an alcoholic flavor of a comestible composition. In certain related embodiments, the disclosure provides methods of enhancing an alcoholic flavor of a comestible composition, the methods comprising introducing to the comestible composition a dihydrochalcone compound disclosed herein. In some embodiments of the foregoing aspects, the comestible composition is a liquid comestible composition, and comprises a liquid carrier. In some embodiments, the liquid carrier comprises water. In some embodiments, the liquid carrier comprises ethanol. In some embodiments, the liquid comestible composition comprises carbon dioxide. In some embodiments, the liquid carrier comprises one or more flavor compounds, such as compounds that impart the flavor (taste or aroma) of certain fruits, tea, coffee, vanilla, chocolate, and the like.

[0010] In a second aspect, the disclosure provides comestible compositions comprising a dihydrochalcone compound disclosed herein and a carrier. In some embodiments, the comestible composition is a liquid comestible composition, and comprises a liquid carrier. In some embodiments, the liquid carrier comprises water. In some embodiments, the liquid carrier comprises ethanol. In some embodiments, the liquid comestible composition comprises carbon dioxide. In some embodiments, the liquid carrier comprises one or more flavor compounds, such as compounds that impart the flavor (taste or aroma) of certain fruits, tea, coffee, vanilla, chocolate, and the like.

[0011] In a third aspect, the disclosure provides a flavored product comprising a comestible composition of the second aspect. In some embodiments, the flavored product is a beverage product, such as a zero-alcohol or low-alcohol beer, a zero-alcohol or low-alcohol cocktail or seltzer, or a reduced-alcohol spirit. In some embodiments, the flavored product is an oral care product, such as a mouthwash, a toothpaste, and the like.

[0012] Further aspects, and embodiments thereof, are set forth below in the Detailed Description, the Drawings, the Abstract, and the Claims.

[0013] BRIEF DESCRIPTION OF THE DRAWINGS

[0014] The drawings are provided for illustrative purposes only and are not intended to describe any preferred compositions or preferred methods, or to serve as a source of any limitations on the scope of the claimed inventions.

[0015] FIG. 1 shows a chemical formula representing a dihydrochalcone compound, wherein R1is a hydrogen atom, methyl, a monosaccharide, or an oligosaccharide; and R2, R3, R4, and R5are each independently a hydrogen atom, -OH, or -OCH3. DETAILED DESCRIPTION

[0016] The following Detailed Description sets forth various aspects and embodiments provided herein. The description is to be read from the perspective of the person of ordinary skill in the relevant art. Therefore, information that is well known to such ordinarily skilled artisans is not necessarily included.

[0017] Definitions

[0018] The following terms and phrases have the meanings indicated below, unless otherwise provided herein. This disclosure may employ other terms and phrases not expressly defined herein. Such other terms and phrases have the meanings that they would possess within the context of this disclosure to those of ordinary skill in the art. In some instances, a term or phrase may be defined in the singular or plural. In such instances, it is understood that any term in the singular may include its plural counterpart and vice versa, unless expressly indicated to the contrary.

[0019] As used herein, the singular forms “a," “an,” and “the” include plural referents unless the context clearly dictates otherwise. For example, reference to “a substituent” encompasses a single substituent as well as two or more substituents, and the like.

[0020] As used herein, “for example,” “for instance,” “such as,” or “including” are meant to introduce examples that further clarify more general subject matter. Unless otherwise expressly indicated, such examples are provided only as an aid for understanding embodiments illustrated in the present disclosure and are not meant to be limiting in any fashion. Nor do these phrases indicate any kind of preference for the disclosed embodiment.

[0021] As used herein, “comprise” or “comprises” or “comprising” or “comprised of’ refer to groups that are open, meaning that the group can include additional members in addition to those expressly recited. For example, the phrase, “comprises A” means that A must be present, but that other members can be present too. The terms “include,” “have,” and “composed of’ and their grammatical variants have the same meaning. In contrast, “consist of’ or “consists of’ or “consisting of’ refer to groups that are closed. For example, the phrase “consists of A” means that A and only A is present.

[0022] As used herein, “optionally” means that the subsequently described event(s) may or may not occur. In some embodiments, the optional event does not occur. In some other embodiments, the optional event does occur one or more times.

[0023] As used herein, “or” is to be given its broadest reasonable interpretation and is not to be limited to an either / or construction. Thus, the phrase “comprising A or B” means that A can be present and not B, or that B is present and not A, or that A and B are both present. Further, if A, for example, defines a class that can have multiple members, e.g., Ai and A2, then one or more members of the class can be present concurrently. As used herein, the term “alcoholic flavor” refers to combination of organoleptic properties humans associate with the oral consumption of ethanol concomitantly with such consumption, including certain taste sensations, olfactory sensations, burning or warming sensations, and textural sensations, including activating of one or more transient receptor potential (TRP) channels, such as TRPA1 channels, TRPV1 channels, and TRPM8 channels. The term does not include certain sensations that may follow the consumption of ethanol, such as the various physical, mental, and psychological effects that eventually result from alcohol consumption and inebriation.

[0024] As used herein, the term “dihydrochalcone compound” refers to any compound encompassed by the genus defined by formula (I), whether or not the compound is specifically set forth herein.

[0025] Other terms are defined in other portions of this description, even though not included in this subsection.

[0026] Dihydrochalcone Compounds

[0027] The uses, methods, compositions, and products disclosed herein relate to dihydrochalcone compounds. The dihydrochalcone compounds are compounds of formula (I): wherein:

[0028] R1is a hydrogen atom, methyl, a monosaccharide, or an oligosaccharide; and

[0029] R2, R3, R4, and R5are each independently a hydrogen atom, -OH, or -OCH3.

[0030] In some embodiments, at least one of R2and R3is not a hydrogen atom. In some further embodiments, both of R2and R3are not a hydrogen atom.

[0031] In some embodiments of any of the foregoing embodiments, at least one of R4and R5is not a hydrogen atom. In some further embodiments, both of R4and R5are not a hydrogen atom.

[0032] In some embodiments, R1is a hydrogen atom. In some other embodiments, R1is methyl (i.e., -CH3).

[0033] In some embodiments, R1is a monosaccharide, such as D-glucose, D-mannose, D-galactose, D-talose, D-gulose, D-iodose, D-allose, D-altrose, D-psisose, D-fructose, D-sorbose, or D-tagatose. In some such embodiments, the monosaccharide is D-glucose, such as D-a-glucose or D-p-glucose. In some embodiments, the monosaccharise is D-p-glucose, such as a D-p-glucose connected via the 1 -position, 2-position, 3-position, 4-position, or 6-position. In some embodiments, the monosaccharide is D-p-glucose connected via the 1 -position.

[0034] In some embodiments, R1is an oligosaccharide, for example, a polysaccharide having from 2 to 20 saccharide units. In some embodiments, the oligosaccharide has from 2 to 5 saccharide units. In some embodiments, the oligosaccharide has 2 or 3 saccharide units. In some embodiments, the oligosaccharide has 2 saccharide units. The saccharide units in the oligosaccharide can be made up of any suitable monosaccharides, such as D-glucose, D-mannose, D-galactose, D-talose, D-gulose, D-iodose, D-allose, D-altrose, D-psisose, D-fructose, D-sorbose, or D-tagatose. In some such embodiments, the oligosaccharide consists of D-glucose units, such as D-a-glucose units or D-p-glucose units. In some embodiments, the oligosaccharide consists of D-p-glucose units. In some embodiments, the oligosaccharide consists of two D-p-glucose units, where the initial D-p-glucose unit is connected to the 1- position and the two D-p-glucose units are connected via a 1 ,6 linkage.

[0035] The variable R2can have any suitable value, according to the definition set forth above. In some embodiments, R2is a hydrogen atom. In some embodiments, R2is -OH. In some embodiments, R2is -OCH3.

[0036] The variable R3can have any suitable value, according to the definition set forth above. In some embodiments, R3is a hydrogen atom. In some embodiments, R3is -OH. In some embodiments, R3is -OCH3.

[0037] The variable R4can have any suitable value, according to the definition set forth above. In some embodiments, R4is a hydrogen atom. In some embodiments, R4is -OH. In some embodiments, R4is -OCH3.

[0038] The variable R5can have any suitable value, according to the definition set forth above. In some embodiments, R5is a hydrogen atom. In some embodiments, R5is -OH. In some embodiments, R5is -OCH3.

[0039] Table 1 below sets forth various examples of dihydrochalcone compounds according to certain embodiments. Each compound is itself a separate embodiment of a dihydrochalcone compound.

[0040] Table 1 In some embodiments, the dihydrochalcone compound is any one of the compounds set forth in Table 1. In some embodiments, the dihydrochalcone compound is Compound 101. In some embodiments, the dihydrochalcone compound is Compound 102. In some embodiments, the dihydrochalcone compound is Compound 103. In some embodiments, the dihydrochalcone compound is Compound 104. In some embodiments, the dihydrochalcone compound is Compound 105. In some embodiments, the dihydrochalcone compound is Compound 106. In some embodiments, the dihydrochalcone compound is Compound 107. In some embodiments, the dihydrochalcone compound is Compound 108. In some embodiments, the dihydrochalcone compound is Compound 109. In some embodiments, the dihydrochalcone compound is Compound 110.

[0041] Isotopes may be present in any of the dihydrochalcone compounds described. Each chemical element as represented in a compound structure may include any isotope of said element. For example, in a compound structure a hydrogen atom may be explicitly disclosed or understood to be present in the compound. At any position of the compound that a hydrogen atom may be present, the hydrogen atom can be any isotope of hydrogen, including but not limited to hydrogen-1 (protium) and hydrogen-2 (deuterium). Thus, reference herein to a compound encompasses all potential isotopic forms unless the context clearly dictates otherwise.

[0042] In some embodiments, the dihydrochalcone compounds capable of forming acid or base salts by virtue of the presence of amino or carboxyl groups or groups similar thereto. Comestibly acceptable acid addition salts can be formed with inorganic acids and organic acids. Inorganic acids from which salts can be derived include, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like. Organic acids from which salts can be derived include, for example, acetic acid, propionic acid, glycolic acid, pyruvic acid, oxalic acid, maleic acid, malonic acid, succinic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicylic acid, and the like. Comestibly acceptable salts can be formed using inorganic and organic bases. Inorganic bases from which salts can be derived include, for example, bases that contain sodium, potassium, lithium, ammonium, calcium, magnesium, iron, zinc, copper, manganese, aluminum, and the like; particularly preferred are the ammonium, potassium, sodium, calcium and magnesium salts. In some embodiments, treatment of the dihydrochalcone compounds disclosed herein with an inorganic base results in loss of a labile hydrogen from the compound to afford the salt form including an inorganic cation such as Li+, Na+, K+, Mg2+and Ca2+and the like. Organic bases from which salts can be derived include, for example, primary, secondary, and tertiary amines, substituted amines including naturally occurring substituted amines, cyclic amines, basic ion exchange resins, and the like, specifically such as isopropylamine, trimethylamine, diethylamine, triethylamine, tripropylamine, and ethanolamine. In some embodiments, the salts are comestibly acceptable salts, which are salts suitable for inclusion in ingestible compositions, such as food or beverage products.

[0043] In some embodiments, the dihydrochalcone compound is in its free (non-salt) form. In other embodiments, the dihydrochalcone compound is a comestibly acceptable salt of any of the compounds set forth above.

[0044] In some embodiments, the dihydrochalcone compounds exist as a crystalline solid, either in substantially pure form or in a formulation such as those set forth below. The crystalline solid can have any suitable polymorphic form, such as any polymorphic form obtainable via recrystallization in any suitable solvent system, according to techniques commonly used in the art of polymorph screening.

[0045] In some other embodiments, the dihydrochalcone compounds exist as an amorphous solid or a semi-amorphous solid, meaning that it lacks any regular crystalline structure. Such solids can be generated using standard techniques, such as spray drying, and the like.

[0046] In some embodiments, the dihydrochalcone compounds exist as a solvate, which is a pseudomorphic form of the compound in which one or more solvent molecules (such as water molecules) are taken up into the crystalline structure. Any suitable solvent or combination of solvents can be used, including, but not limited to, water, methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-butanol, isobutanol, ethyl acetate, ethylene glycol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, and the like. In some embodiments, the disclosure provides hydrates of the dihydrochalcone compounds. Such solvates can be generated by any suitable means, such as those techniques typically used by skilled artisans in the field of polymorph and solvate screening.

[0047] In some embodiments, the dihydrochalcone compounds are in the form of a dry particle. Such dry particles can be formed by standard techniques in the art, such as dry granulation, wet granulation, and the like. Such particles can also contain a number of excipients, including, inert diluents, such as calcium carbonate, sodium carbonate, lactose, calcium phosphate, and sodium phosphate; granulating and disintegrating agents, such as starch, cellulosic materials, and alginic acid; binding agents, such as gelatin, guar gum, and acacia; and lubricating agents, such as magnesium stearate, stearic acid, and talc. Other excipients typically used in food and beverage products can also be included, such as typical foodstuff materials.

[0048] In some embodiments, the dihydrochalcone compounds are in the form of a liquid solution or a liquid suspension. Such compositions can also include: carboxymethyl-cellulose, methylcellulose, hydroxypropylmethylcellulose, sodium alginate, polyvinyl-pyrrolidone, gum tragacanth and gum acacia; dispersing or wetting agents may be a naturally-occurring phosphatide such as lecithin, or condensation products of an alkylene oxide with fatty acids, for example polyoxyethylene stearate, or condensation products of ethylene oxide with long chain aliphatic alcohols, for example, heptadecaethyl-eneoxycetanol, or condensation products of ethylene oxide with partial esters derived from fatty acids and a hexitol such as polyoxyethylene sorbitol monooleate, or condensation products of ethylene oxide with partial esters derived from fatty acids and hexitol anhydrides, for example polyethylene sorbitan monooleate. Such compositions can also include one or more coloring agents, one or more flavoring agents, and the like. Such liquid suspensions and solutions have a liquid carrier. In general, the liquid carrier comprises water. In some such cases, the liquid composition is an emulsion, such as an oil-in-water or a water-in-oil emulsion. Further, in some cases, water may be too polar to dissolve the dihydrochalcone compounds to the desired concentration. In such instances, it can be desirable to introduce water-miscible solvents, such as alcohols, glycols, polyols, and the like, to the solvent to enhance solubilization of the dihydrochalcone compounds.

[0049] In some embodiments, the dihydrochalcone compounds are in the form of a solution, i.e. , are solvated within a liquid carrier. In some embodiments, the liquid carrier is an aqueous carrier. Such solutions can be diluted to any suitable concentration.

[0050] Uses and Methods

[0051] In certain aspects, the disclosure provides use of a dihydrochalcone compound, as disclosed herein, for enhancing an alcoholic (ethanolic) flavor of a comestible composition. In certain related aspects, the disclosure provides methods of enhancing an alcoholic (ethanolic) flavor of a comestible composition, the method comprising introducing a dihydrochalcone compound, as disclosed herein, to the comestible composition.

[0052] In certain aspects, the disclosure provides use of a dihydrochalcone compound, as disclosed herein, for reducing an alcohol (ethanol) content of a comestible composition. In certain related aspects, the disclosure provides methods of reducing an alcohol (ethanol) content of a comestible composition, the method comprising introducing to the comestible composition a dihydrochalcone compound, as disclosed herein. In some embodiments of the foregoing uses or methods, introducing the dihydrochalcone compound allows one to reduce the ethanol content of the comestible composition by at least 5%, or at least 10%, or at least 20%, or at least 30%, or at least 40%, or at least 50%, or at least 60%, or at least 70%, or at least 80%, or at least 90%, or 100%, in comparison to a comparable composition having a standard ethanol content and not including any dihydrochalcone compound.

[0053] Any suitable concentration of a dihydrochalcone compound can be used in or introduced to the comestible composition. In some embodiments, the dihydrochalcone compound is used in or introduced to the comestible composition at a concentration ranging from 1 ppm to 1000 ppm, or from 5 ppm to 500 ppm, or from 10 ppm to 200 ppm, or from 20 ppm to 100 ppm, or from 25 ppm to 75 ppm, or from 35 ppm to 65 ppm, or from 5 ppm to 50 ppm, or from 10 ppm to 50 ppm, based on the total weight of the comestible composition. Further embodiments concerning the comestible compositions are set forth in the section below, any of which may be combined with the embodiments set forth in this section.

[0054] Comestible Compositions and Flavored Products

[0055] In certain aspects, the disclosure provides comestible compositions comprising the dihydrochalcone compounds, as disclosed herein, and a carrier.

[0056] The comestible composition can have any suitable physical form, such as a solid, a solid-liquid dispersion or suspension, or a liquid. In some embodiments, the comestible composition is a liquid and comprises a liquid carrier. In some embodiments, the liquid carrier comprises water and, optionally, one or more water-miscible solvents, such as certain glycols, emulsifiers, and the like. In some embodiments, the comestible composition comprises carbon dioxide, for example, dissolved in the liquid under pressure. Any suitable concentration of carbon dioxide can be used. For example, in some embodiments, the liquid comestible composition comprises from 1 g / L to 25 g / L, or from 2 g / L to 15 g / L, or from 3 g / L to 10 g / L, based on the total volume of the liquid comestible composition.

[0057] In some embodiments, the comestible composition is substantially free of ethanol, for example, it comprises no more than 1.2% by volume, or no more than 1.1% by volume, or no more than 1 .0% by volume, or no more than 0.9% by volume, or no more than 0.8% by volume, or no more than 0.7% by volume, or no more than 0.6% by volume, or no more than 0.5% by volume, or no more than 0.4% by volume, or no more than 0.3% by volume, or no more than 0.2% by volume, or no more than 0.1% by volume, based on the total volume of the comestible composition. In some other embodiments, the comestible composition comprises ethanol, for example at concentrations ranging from 1% by volume to 10% by volume, or from 1% by volume to 8% by volume, or from 1% by volume to 6% by volume, or from 1% by volume to 5% by volume, or from 1% by volume to 4% by volume, or from 1% by volume to 3% by volume, or from 1% by volume to 2% by volume, based on the total volume of the comestible composition. In some embodiments, the comestible composition may be a reduced-alcohol spirit. For some such embodiments, the comestible composition comprises ethanol at concentrations ranging from 15% by volume to 35% by volume, or from 20% by volume to 35% by volume, or from 25% by volume to 35% by volume, based on the total volume of the comestible composition.

[0058] In a preferred embodiment, the comestible composition, preferably liquid comestible composition, comprises ethanol at a concentration from 4% to 6% by volume, preferably of 5% by volume.

[0059] In certain embodiments, the comestible composition comprises one or more organic acids. Any suitable organic acid can be used. Certain non-limiting examples include citric acid, malic acid, ascorbic acid, lactic acid, fumaric acid, tartaric acid, maleic acid, quinic acid, aconitic acid, succinic acid, pyruvic acid, pyroglutamic acid, gallic acid, ascorbic acid, formic acid, acetic acid, propionic acid, butyric acid, lactic acid, creatine, oxalic acid, and any acid addition salts thereof, such as sodium salts of any of the foregoing. In some embodiments, the one or more organic acids. In some embodiments, the organic acid is citric acid, an acid addition salt thereof (such as a sodium salt), or any combination of the foregoing. In some embodiments, the organic acid is malic acid, an acid addition salt thereof (such as a sodium salt), or any combination of the foregoing. In some embodiments, the organic acid is lactic acid, an acid addition salt thereof (such as a sodium salt), or any combination of the foregoing. In some embodiments, the organic acid is succinic acid, an acid addition salt thereof (such as a sodium salt), or any combination of the foregoing. In some embodiments, the organic acid is ascorbic acid, an acid addition salt thereof (such as a sodium salt), or any combination of the foregoing. Such organic acids can be present at any suitable concentration. For example, in some such embodiments, the organic acid is present in the comestible composition at a concentration ranging from 10 ppm to 500 ppm, or from 10 ppm to 250 ppm, based on the total weight of the comestible composition.

[0060] In some embodiments, the comestible composition comprises a fusel alcohol. Any suitable fusel alcohols can be used. This includes C3.6alkanols, as well as certain arylalkanols, certain heteroarylalkanols, and certain C3.6alkanols comprising ether or thioether groups in the alkane chain. In some embodiments, the fusel alcohol is 3-methyl-1 -butanol, 2-methyl-1- butanol, 2-methyl-1 -propanol, 1 -propanol, isopropanol, 1 -butanol, 1 -pentanol, 1 -hexanol,

[0061] 2-phenylethanol, tyrosol, tryptophol, methionol, or any combination thereof. In some embodiments, the fusel alcohol is 3-methyl-1 -butanol, 2-methyl-1-butanol, 2-methyl- 1-propanol, 1-propanol, or any combination thereof. In some embodiments, the fusel alcohol is

[0062] 3-methyl-1 -butanol, 2-methyl-1-butanol, or any combination thereof. The fusel alcohol can be present in the comestible composition in any suitable concentration. In some such embodiments, the fusel alcohol is present in the comestible composition at a concentration ranging from 1 ppm to 100 ppm, or from 2 ppm to 50 ppm, based on the total weight of the comestible composition.

[0063] In some embodiments, the comestible composition comprises one or more sweeteners. In some embodiments, the sweetener includes common saccharide sweeteners, such as sucrose, fructose, glucose, and sweetener compositions comprising natural sugars, such as corn syrup (including high fructose corn syrup) or other syrups or sweetener concentrates derived from natural fruit and vegetable sources. In some embodiments, the sweetener is sucrose, fructose, or a combination thereof. In some embodiments, the sweetener is sucrose.

[0064] In some other embodiments, the sweetener includes rare natural sugars, such as D-allose, D-psicose, L-ribose, D-tagatose, L-glucose, L-fucose, L-arbinose, D-turanose, D-leucrose, or any combinations thereof. In some embodiments, the sweetener includes semisynthetic “sugar alcohol” sweeteners such as erythritol, isomalt, lactitol, mannitol, sorbitol, xylitol, maltodextrin, and the like. In some embodiments, the sweetener includes artificial sweeteners such as aspartame, saccharin, acesulfame potassium, cyclamate, and sucralose. In some embodiments, the sweetener includes a sweetener selected from the group consisting of cyclamic acid, mogroside, tagatose, maltose, galactose, mannose, sucrose, fructose, lactose, allulose, neotame and other aspartame derivatives, glucose, D-tryptophan, glycine, maltitol, lactitol, isomalt, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolyzate (HSH), stevioside, rebaudioside A, other sweet Stevia-based glycosides, chemically modified steviol glycosides (such as glucosylated steviol glycosides), mogrosides, chemically modified mogrosides (such as glucosylated mogrosides), carrelame and other guanidine-based sweeteners.

[0065] In some embodiments, he sweetener includes agave inulin, agave nectar, agave syrup, amazake, brazzein, brown rice syrup, coconut crystals, coconut sugars, coconut syrup, date sugar, fructans (also referred to as inulin fiber, fructo-oligosaccharides, or oligo-fructose), green stevia powder, stevia rebaudiana, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M and other sweet stevia-based glycosides, stevioside, stevioside extracts, honey, honey distillate, Jerusalem artichoke syrup, licorice root, luo han guo (fruit, powder, or extracts), lucuma (fruit, powder, or extracts), maple sap (including, for example, sap extracted from Acer saccharum, Acer nigrum, Acer rubrum, Acer saccharin urn, Acer platanoides, Acer negundo, Acer macrophyllum, Acer grandidentatum, Acer glabrum, Acer mono), maple syrup, maple sugar, walnut sap (including, for example, sap extracted from Juglans cinerea, Juglans nigra, Juglans ailantifolia, Juglans regia), birch sap (including, for example, sap extracted from Betula papyrifera, Betula alleghaniensis, Betula lenta, Betula nigra, Betula populifolia, Betula pendula), sycamore sap (such as, for example, sap extracted from Platanus occidentalis), ironwood sap (such as, for example, sap extracted from Ostrya virginiana), mascobado, molasses (such as, for example, blackstrap molasses), molasses sugar, monatin, monellin, cane sugar (also referred to as natural sugar, unrefined cane sugar, or sucrose), palm sugar, panocha, piloncillo, rapadura, raw sugar, rice syrup, sorghum, sorghum syrup, cassava syrup (also referred to as tapioca syrup), thaumatin, yacon root, malt syrup, barley malt syrup, barley malt powder, beet sugar, cane sugar, crystalline juice crystals, caramel, carbitol, carob syrup, castor sugar, hydrogenated starch hydrolates, hydrolyzed can juice, hydrolyzed starch, invert sugar, anethole, arabinogalactan, arrope, syrup, P-4000, acesulfame potassium (also referred to as acesulfame K or ace-K), alitame (also referred to as aclame), advantame, aspartame, baiyunoside, neotame, benzamide derivatives, bernadame, canderel, carrelame and other guanidine-based sweeteners, vegetable fiber, corn sugar, coupling sugars, curculin, cyclamates, cyclocarioside I, demerara, dextran, dextrin, diastatic malt, dulcin, sucrol, valzin, dulcoside A, dulcoside B, emulin, enoxolone, maltodextrin, saccharin, estragole, ethyl maltol, glucin, gluconic acid, glucono-lactone, glucosamine, glucoronic acid, glycerol, glycine, glycyphillin, glycyrrhizin, glycyrrhetic acid monoglucuronide, golden sugar, yellow sugar, golden syrup, granulated sugar, gynostemma, hernandulcin, isomerized liquid sugars, jallab, chicory root dietary fiber, kynurenine derivatives (including N'-formyl-kynurenine, N'-acetyl-kynurenine, 6-chloro-kynurenine), galactitol, litesse, ligicane, lycasin, lugduname, guanidine, falernum, mabinlin I, mabinlin II, maltol, maltisorb, maltodextrin, maltotriol, mannosamine, miraculin, mizuame, mogrosides (including, for example, mogroside IV, mogroside V, and neomogroside), mukurozioside, nano sugar, naringin dihydrochalcone, neohesperidine dihydrochalcone, nib sugar, nigero-oligosaccharide, norbu, orgeat syrup, osladin, pekmez, pentadin, periandrin I, perillaldehyde, perillartine, petphyllum, phenylalanine, phlomisoside I, phlorodizin, phyllodulcin, polyglycitol syrups, polypodoside A, pterocaryoside A, pterocaryoside B, rebiana, refiners syrup, rub syrup, rubusoside, selligueain A, shugr, siamenoside I, siraitia grosvenorii, soybean oligosaccharide, Splenda, SRI oxime V, steviol glycoside, steviolbioside, stevioside, strogins 1 , 2, and 4, sucronic acid, sucrononate, sugar, suosan, phloridzin, superaspartame, tetrasaccharide, threitol, treacle, trilobtain, tryptophan and derivatives (6-trifluoromethyl- tryptophan, 6-chloro-D-tryptophan), vanilla sugar, volemitol, birch syrup, aspartameacesulfame, assugrin, or combinations or blends of any two or more thereof.

[0066] In some embodiments, the sweetener includes a natural high-intensity sweetener, such as a steviol glycoside, a mogroside, another plant-derived sweetener, such as glycyrrhizin, or any combination thereof. Suitable steviol glycosides include stevioside, rebaudioside A, rebaudioside B, rebaudioside D, rebaudioside E, rebaudioside M, or any combinations thereof. Suitable mogrosides include monk fruit extract, mogroside III, mogroside IV, mogroside V, siamenoside I, isomogroside V, mogroside IVE, isomogroside IV, mogroside lllE, 11- oxomogroside V, the 1 ,6-a isomer of siamenoside I, or any combinations thereof.

[0067] Suitable concentrations for such sweeteners are well known in the art. In some embodiments, the natural high-intensity sweeteners are present in the comestible composition at a concentration ranging from 10 ppm to 500 ppm, or from 50 ppm to 200 ppm, based on the total weight of the comestible composition.

[0068] In some embodiments, the flavoring composition comprises a fatty acid, which can enhance mouthfeel and block certain astringent or bitter notes. Some non-limiting examples of suitable fatty acids include octanoic acid, decanoic acid, undecylenic acid, dodecanoic acid, myristic acid, palmitic acid, stearic acid, oleic acid, and any combinations thereof. In general, such fatty acids, when present, are included at low quantities. For example, in some embodiments, the fatty acids are present in the comestible composition at a concentration ranging from 0.01 ppm to 10 ppm, or from 0.5 ppm to 5 ppm, based on the total weight of the comestible composition. In some cases, the flavoring composition is designed to impart a beer-like flavor. Thus, in some embodiments, the flavoring composition comprises one or more ingredients that impart certain flavors characteristic of those found in beer, such as hop oil, certain sulfur-containing compounds, and fermented products, such as yeast extracts or other products of fermentation processes. Depending on their flavor intensity, such ingredients can be used at relatively low concentrations, such as at concentrations ranging from 0.05 ppm to 10 ppm in the comestible composition.

[0069] In some embodiments, the flavoring compositions include compounds that have a cooling or heating effect. These include compounds that activate of one or more transient receptor potential (TRP) channels, such as TRPA1 channels, TRPV1 channels, and TRPM8 channels, such as menthol and menthol analogs, various pepper or peppercorn extracts, piperine and its analogs, capsaicin and its analogs, hydroxy-alpha-sanshool and its analogs, and the like. In general, such compounds are used at relatively low concentrations, such as from 0.5 ppm to 50 ppm in the comestible composition.

[0070] In certain embodiments, the comestible compositions comprises additional ingredients or combination of ingredients as are commonly used in beverage products, including, but not limited to: acids, including, for example citric acid, phosphoric acid, ascorbic acid, sodium acid sulfate, lactic acid, or tartaric acid; coloring agents, including, for example caramel color, Red #40, Yellow #5, Yellow #6, Blue #1 , Red #3, purple carrot, black carrot juice, purple sweet potato, vegetable juice, fruit juice, beta carotene, turmeric curcumin, or titanium dioxide; preservatives, including, for example sodium benzoate, potassium benzoate, potassium sorbate, sodium metabisulfate, sorbic acid, or benzoic acid; antioxidants including, for example ascorbic acid, calcium disodium EDTA, alpha tocopherols, mixed tocopherols, rosemary extract, grape seed extract, resveratrol, or sodium hexametaphosphate; vitamins or functional ingredients including, for example resveratrol, Co-Q10, omega 3 fatty acids, theanine, choline chloride (citocoline), fibersol, inulin (chicory root), taurine, panax ginseng extract, guanana extract, ginger extract, L-phenylalanine, L-carnitine, L-tartrate, D- glucoronolactone, inositol, biodihydrochalcones, Echinacea, ginko biloba, yerba mate, flax seed oil, garcinia cambogia rind extract, white tea extract, ribose, milk thistle extract, grape seed extract, pyrodixine HCI (vitamin B6), cyanoobalamin (vitamin B12), niacinamide (vitamin B3), biotin, calcium lactate, calcium pantothenate (pantothenic acid), calcium phosphate, calcium carbonate, chromium chloride, chromium polynicotinate, cupric sulfate, folic acid, ferric pyrophosphate, iron, magnesium lactate, magnesium carbonate, magnesium sulfate, monopotassium phosphate, monosodium phosphate, phosphorus, potassium iodide, potassium phosphate, riboflavin, sodium sulfate, sodium gluconate, sodium polyphosphate, sodium bicarbonate, thiamine mononitrate, vitamin D3, vitamin A palmitate, zinc gluconate, zinc lactate, or zinc sulphate; clouding agents, including, for example ester gun, brominated vegetable oil (BVO), or sucrose acetate isobutyrate (SAIB); buffers, including, for example sodium citrate, potassium citrate, or salt; flavors, including, for example propylene glycol, ethyl alcohol, glycerine, gum arabic (gum acacia), maltodextrin, modified corn starch, dextrose, natural flavor, natural flavor with other natural flavors (natural flavor WONF), natural and artificial flavors, artificial flavor, silicon dioxide, magnesium carbonate, or tricalcium phosphate; or starches and stabilizers, including, for example pectin, xanthan gum, carboxylmethylcellulose (CMC), polysorbate 60, polysorbate 80, medium chain triglycerides, cellulose gel, cellulose gum, sodium caseinate, modified food starch, gum Arabic (gum acacia), inulin, or carrageenan.

[0071] The comestible compositions can have any suitable pH. In some embodiments, the flavor-modifying compounds enhance the sweetness of a sweetener under a broad range of pH, e.g., from lower pH to neutral pH. The lower and neutral pH includes a pH from 1 .5 to 9.0, or from 2.5 to 8.5; from 3.0 to 8.0; from 3.5 to 7.5; and from 4.0 to 7.

[0072] In some embodiments, the comestible composition comprises a flavoring. Such flavorings can include volatile compounds, which primarily affect the aroma of the comestible composition, or nonvolatile compounds, which primarily affect the taste of the comestible composition. Any suitable flavoring can be used. In some embodiments, the flavoring comprises synthetic flavor oils and flavoring aromatics or oils, oleoresins and extracts derived from plants, leaves, flowers, fruits, and so forth, or combinations thereof. Non-limiting examples of flavor oils include spearmint oil, cinnamon oil, oil of Wintergreen (methyl salicylate), peppermint oil, Japanese mint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, oil of nutmeg, allspice, oil of sage, mace, oil of bitter almonds, and cassia oil. Nonlimiting examples of other flavors include natural and synthetic fruit flavors such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, yazu, sudachi, and fruit essences including apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, pineapple, watermelon, apricot, banana, melon, apricot, ume, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya and so forth. Other potential flavors include a milk flavor, a butter flavor, a cheese flavor, a cream flavor, and a yogurt flavor; a vanilla flavor; tea or coffee flavors, such as a green tea flavor, a oolong tea flavor, a tea flavor, a cocoa flavor, a chocolate flavor, and a coffee flavor; mint flavors, such as a peppermint flavor, a spearmint flavor, and a Japanese mint flavor; spicy flavors, such as an asafetida flavor, an ajowan flavor, an anise flavor, an angelica flavor, a fennel flavor, an allspice flavor, a cinnamon flavor, a chamomile flavor, a mustard flavor, a cardamom flavor, a caraway flavor, a cumin flavor, a clove flavor, a pepper flavor, a coriander flavor, a sassafras flavor, a savory flavor, a Zanthoxyli Fructus flavor, a perilla flavor, a juniper berry flavor, a ginger flavor, a star anise flavor, a horseradish flavor, a thyme flavor, a tarragon flavor, a dill flavor, a capsicum flavor, a nutmeg flavor, a basil flavor, a marjoram flavor, a rosemary flavor, a bayleaf flavor, and a wasabi (Japanese horseradish) flavor; alcoholic flavors, such as a wine flavor, a whisky flavor, a brandy flavor, a rum flavor, a gin flavor, and a liqueur flavor; floral flavors; and vegetable flavors, such as an onion flavor, a garlic flavor, a cabbage flavor, a carrot flavor, a celery flavor, mushroom flavor, and a tomato flavor. These flavoring agents may be used in liquid or solid form and may be used individually or in admixture. In the context of dairy or dairy analog products, the most commonly used flavor agents are agents that impart flavors such as vanilla, French vanilla, chocolate, banana, lemon, hazelnut, coconut, almond, strawberry, mocha, coffee, tea, chai, cinnamon, caramel, cream, brown sugar, toffee, pecan, butter pecan, toffee, Irish creme, white chocolate, raspberry, pumpkin pie spice, peppermint, or any combination thereof.

[0073] In some embodiments, the comestible composition comprises certain aromatic compounds, such as aromatic esters and aldehydes. In some further embodiments, the comestible composition comprises one or more lactones, which impart a creamy flavor to the composition.

[0074] In some embodiments, the comestible composition comprises yeast, probiotic bacteria, or any combination thereof, such as symbiotic colonies of both, which ferment various sugars and include probiotic benefits to the comestible composition.

[0075] In some embodiments, the comestible composition comprises a sweetness enhancer. Any suitable sweetness enhancer can be used in the ingestible compositions disclosed herein, including synthetic sweetness enhancers, natural sweetness enhancers, or any combinations thereof.

[0076] Examples of suitable synthetic sweetness enhancers include, but are not limited to, / V-(1-((4-amino-2,2-dioxo-1 / - / -benzo[c][1 ,2,6]thiadiazin-5-yl)oxy)-2-methylpropan- 2-yl)isonicotinamide, 3-((4-amino-2,2-dioxo-1 / - / -benzo[c][1 ,2,6]thiadiazin-5-yl)oxy)- 2,2-dimethyl- / V-propyl-propanamide, 3-hydroxybenzoic acid, 2,4-dihydroxybenzoic acid, or any compounds set forth in U.S. Patent Nos. 8,541 ,421 ; 8,815,956; 9,834,544; 8,592,592; 8,877,922; 9,000,054; and 9,000,051 , as well as U.S. Patent Application Publication No. 2017 / 0119032.

[0077] Suitable examples of natural sweetness enhancers include, but are not limited to, hesperetin dihydrochalcone, hesperetin dihydrochalcone-4’-0’glucoside, neohesperetin dihydrochalcone, brazzein, hesperidin, phyllodulcin, naringenin, naringin, phloretin, glucosylated steviol glycosides, (2R,3R)-3-acetoxy-5,7,4’-trihydroxyflavanone, (2R,3R)-3-acetoxy-5,7,3’-trihydroxy-4’-methoxyflavanone, rubusosides, thaumatin, monellin, miraculin, glycyrrhizin and comestible acceptable salts thereof (such as the mono-ammonium salt), naringin dihydrochalcone, myricetin, nobiletin, polymethoxyflavones, mixed methoxy- and hydroxyflavones, quercetin, certain amino acids, and the like. As used herein, the term “glucosylated steviol glycoside” refers to the product of enzymatically glucosylating natural steviol glycoside compounds. The glucosylation generally occurs through a glycosidic bond, such as an a-1 ,2 bond, an a-1 ,4 bond, an a-1.6 bond, a p-1 ,2 bond, a p-1 ,4 bond, a p-1 ,6 bond, and so forth.

[0078] In some embodiments, the comestible composition comprises one or more umami enhancing compounds. Such umami enhancing compounds include, but are not limited to, naturally derived compounds, or synthetic compounds, such as any compounds set forth in U.S. Patent Nos. 8,735,081 ; 8,124,121 ; and 8,968,708. In some embodiments, the umamienhancing compound is (2R,4R)-1 ,2,4-trihydroxy-heptadec-16-ene, (2R,4R)-1 ,2,4- trihydroxyheptadec-16-yne, or a mixture thereof. In some embodiments, the umami-enhancing compound is (3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol diacetate. In some embodiments, the umami-enhancing compound is A / -(heptan-4-yl)benzo-[d][1 ,3]dioxole-5- carboxamide.

[0079] In some further embodiments, the comestible composition comprises one or more cooling enhancing compounds. Such cooling enhancing compounds include, but are not limited to, naturally derived compounds, such as menthol or analogs thereof, or synthetic compounds, such as any compounds set forth in U.S. Patent Nos. 9,394,287 and 10,421 ,727. Non-limiting examples include N-ethyl-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, N-(1 H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, 2-(4-fluorophenoxy)-N- (1 H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide, 2-(2-hydroxy-4-methylphenoxy)- N-(1 H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide, 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N- (1 H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide, 2-((2,3-dihydro-1 H-inden- 5-yl)oxy)-N-(1 H-pyrazol-3-yl)-N-(thiazol-5-ylmethyl)-acetamide, 2-((5-methoxybenzofuran- 2-yl)oxy)-N-(1 H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide, (E / Z)-2-methyl- 2-butenal, (E / Z)-2-isopropyl-5-methyl-2-hexenal, phloretin, naringenin, and any combinations thereof.

[0080] In some further embodiments, the comestible composition comprises one or more bitter blocking or bitter masking compounds. Such bitter blocking compounds or bitter masking compounds include, but are not limited to, naturally derived compounds or synthetic compounds, such as any compounds set forth in U.S. Patent Nos. 8,076,491 ; 8,445,692; and 9,247,759. Non-limiting examples include 3-(1-((3,5-dimethylisoxazol-4-yl)-methyl)-1 / - / -pyrazol- 4-yl)-1-(3-hydroxybenzyl)-imidazolidine-2, 4-dione, 4-(2,2,3-trimethyl-cyclopentyl)butanoic acid, 3p-hydroxydihydrocostunolide, 3|3-hydroxypelenolide, probenecid, sakuranetin, 6- methoxysakuranetin, jaceosidin, 4’-fluoro-6-methoxyflavonone, 6,3’-dimethoxyflavonone, 6- methoxyflavonone, y-aminobutyric acid, Na,Na-bis(carbomethyl)-L-lysine, (+ / -) abscisic acid, sodium gluconate, monosodium glutamate, sodium acetate, homoeriodictyol, sterubin, eriodictyol, 2, 4, dihydroxybenzoic acid, neodiosmin, 1-carboxymethyl-5-hydroxy-2- hydroxymethylpyridinium, flavan-3-spiro-C-glycosides, poly-y-glutamic acid, a,a-trehalose, taurine, (2)-gingerdione, L-theanine, enterodiol, lariciresinol, enterolactone, matairesinol, and any combinations thereof.

[0081] In some further embodiments, the comestible composition comprises one or more sour taste modulating compounds.

[0082] In some further embodiments, the comestible composition comprises one or more mouthfeel modifying compounds. Such mouthfeel modifying compounds include, but are not limited to, tannins, cellulosic materials, bamboo powder, and the like.

[0083] In some further embodiments, the comestible composition comprises one or more flavor masking compounds. Such flavor masking compounds include, but are not limited to, cellulosic materials, materials extracted from fungus, materials extracted from plants, citric acid, carbonic acid (or carbonates), and the like.

[0084] In some embodiments, the comestible product comprises carbon dioxide, for example, to form a carbonated beverage. Flavored seltzers are a non-limiting example of such beverages.

[0085] The comestible composition can also include various other ingredients that are commonly used in food and beverage products. These include various emulsifiers, stabilizers, surfactants, freezing point depressants, preservatives, colorants, caffeine, taurine, foaming agents, antioxidants, buffering agents, and the like.

[0086] In certain aspects, the disclosure provides a flavored product comprising a comestible composition of the previous aspect. In some embodiments, the flavored product is a beverage product, such as a zero-alcohol or low-alcohol beer, or a zero-alcohol or low-alcohol cocktail or seltzer. In some embodiments, the flavored product is a reduced-alcohol spirit, such as reduced-alcohol analogue of vodka, gin, tequila, whisky, bourbon, rum, grappa, brandy, cognac, and the like. In some embodiments, the flavored product is a fermented product, such as a kombucha.

[0087] EXAMPLES

[0088] To further illustrate this invention, the following examples are included. The examples should not, of course, be construed as specifically limiting the invention. Variations of these examples within the scope of the claims are within the purview of one skilled in the art and are considered to fall within the scope of the invention as described and claimed herein. The reader will recognize that the skilled artisan, armed with the present disclosure, and skill in the art is able to prepare and use the invention without exhaustive examples. 16500 / SNMX / WC

[0089] Example 1 - Sensory Testing

[0090] Compound 103 was added at various concentrations to model beverages and compared to a model beverage without Compound 103. Table 2 records the consensus of the sensory panelists who participated in the tests. Table 2

Claims

CLAIMS1. Use of a dihydrochalcone compound to enhance an alcoholic flavor of a comestible composition, wherein the dihydrochalcone compound is a compound of formula (I) or a comestibly acceptable salt thereof:wherein:R1is a hydrogen atom, methyl, a monosaccharide, or an oligosaccharide; and R2, R3, R4, and R5are each independently a hydrogen atom, -OH, or -OCHs.

2. The use of claim 1 , wherein R2is a hydrogen atom or -OH, and R3is -OH.

3. The use of claim 1 or 2, wherein R4is -OH or -OCH3, and R5is a hydrogen atom or -OH.

4. The use of any one of claims 1 to 3, wherein R1is a hydrogen atom or methyl.

5. The use of any one of claims 1 to 3, wherein R1is a monosaccharide or a disaccharide.

6. The use of any one of claims 1 to 5, wherein the comestible composition is a liquid comestible composition.

7. The use of any one of claims 1 to 6, wherein the comestible composition comprises no more than 1 .2% ethanol by volume.

8. The use of any one of claims 1 to 6, wherein the comestible composition comprises from 1 % ethanol by volume to 10% ethanol by volume.

9. A method of enhancing an alcoholic flavor of a comestible composition, the method comprising introducing to the comestible composition a dihydrochalcone compound, wherein the dihydrochalcone compound is a compound of formula (I) or a comestibly acceptable salt thereof:wherein:R1is a hydrogen atom, methyl, a monosaccharide, or an oligosaccharide; and R2, R3, R4, and R5are each independently a hydrogen atom, -OH, or -OCH3.

10. The method of claim 9, wherein R2is a hydrogen atom or -OH, and R3is -OH.11 . The method of claim 9 or 10, wherein R4is -OH or -OCH3, and R5is a hydrogen atom or - OH.

12. The method of any one of claims 9 to 11 , wherein R1is a hydrogen atom or methyl.

13. The method of any one of claims 9 to 11 , wherein R1is a monosaccharide or a disaccharide.

14. The method of any one of claims 9 to 13, wherein the comestible composition is a liquid comestible composition.

15. The method of any one of claims 9 to 14, wherein the comestible composition comprises no more than 1 .2% ethanol by volume.

16. The method of any one of claims 9 to 14, wherein the comestible composition comprises from 1% ethanol by volume to 10% ethanol by volume.

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