Use of vanillyl ether to modify flavors

Abstract

The present disclosure relates generally to vanillyl ether compounds and their use in modifying the flavor of ingestible compositions, such as reducing bitterness, reducing astringency, reducing persistent sweetness, improving mouthfeel, or any combination thereof. In certain forms, the present disclosure provides an ingestible composition comprising a vanillyl ether compound. In some embodiments, the ingestible composition comprises a non-animal protein. In some embodiments, the ingestible composition comprises a high intensity sweetener, such as a steviol glycoside sweetener. In certain forms, the present disclosure provides flavored products, such as food products, beverage products, oral care products, nutraceutical products, or pharmaceutical products, comprising such ingestible compositions.

Description

TECHNICAL FIELD

[0001] The present disclosure relates generally to vanillyl ether compounds and their use in modifying the flavor of ingestible compositions, such as reducing bitterness, reducing astringency, reducing lingering sweetness, improving mouthfeel, or any combination thereof. In certain aspects, the present disclosure provides ingestible compositions comprising a vanillyl ether compound. In some embodiments, the ingestible composition comprises a non-animal protein. In some embodiments, the ingestible composition comprises a high intensity sweetener, such as a steviol glycoside sweetener. In certain aspects, the present disclosure provides a flavorer product, such as a food product, a beverage product, an oral care product, a nutraceutical product, or a pharmaceutical product, comprising such an ingestible composition. BACKGROUND

[0002] The taste system provides sensory information about the chemical composition of the outside world. Taste transduction is one of the more complex forms of chemically triggered sensation in animals. Signals for taste can be found throughout the animal kingdom, from simple invertebrates to the most complex vertebrates. Mammals are thought to have five basic forms of taste: sweet, bitter, sour, salty, and umami.

[0003] Obesity, diabetes, and cardiovascular disease are major health problems worldwide and are growing at an alarming rate. Sugar and calories are key ingredients that can be limited to have a positive nutritional effect on health. Even so, because many foods contain ingredients that stimulate bitter receptors, consumers often use sugar and other sweeteners to offset the bitterness in these foods. In addition, certain nutrient-rich foods, such as plant proteins, stimulate bitter receptors. Thus, despite their nutritional value, consumers can avoid consuming such foods because of the perceived bad taste. In addition, many pharmaceutical compounds, such as antibiotics, have a pronounced bitter taste. Thus, nutraceutical or pharmaceutical manufacturers must employ complex formulation techniques to enable subjects to orally administer such drugs without discomfort.

[0004] However, the physiological basis for bitter and astringent perception is not fully understood. Some compounds are known to reduce certain bitter and astringent tastes. But many such compounds are complex organic compounds that can be costly to manufacture and are not typically found in nature. Thus, there is a continuing need to discover new compounds that can act as effective blockers of certain bitter or astringent tastes. SUMMARY

[0005] The present disclosure relates to the unexpected discovery that vanillyl ether compounds can effectively reduce various bitter tastes as well as astringent tastes, and in some cases without compromising the perceived smoothness, perceived roundness, and mouthfeel of the product in which they are used.

[0006] In a first aspect, the present disclosure provides the use of a vanillyl ether compound for modifying the flavor of an ingestible composition, wherein the vanillyl ether compound is a compound of Formula (I) or an edible acceptable salt thereof:

[0007]

[0008] wherein:

[0009] R 1 is a methyl or ethyl group; and

[0010] R 2 is a hydrogen atom, C 1-8 alkyl group, or C 3-8 cycloalkyl group, or -CH2-(phenyl), wherein the phenyl moiety is optionally substituted one to two times with substituents independently selected from -OH and -OCH3.

[0011] In a related aspect, the present disclosure provides a method of modifying the flavor of an ingestible composition, the method comprising introducing a vanillyl ether compound into the ingestible composition, wherein the vanillyl ether compound is a compound of Formula (I) or an edible acceptable salt thereof as described above. In some embodiments, the ingestible composition comprises one or more bitter or astringent tastants, such as caffeine, tannins, compounds from coffee, compounds from ginseng, non-animal proteins (e.g., pea protein, soy protein, potato protein, or algal protein), animal proteins (e.g., whey protein or casein protein), citrus fruits or juices, and high intensity sweeteners (e.g., saccharin, steviol glycosides, mogrosides, aspartame), and the like. In some embodiments, modifying the flavor comprises reducing bitterness, reducing astringency, reducing a lingering aftertaste (e.g., a lingering sweet aftertaste), or any combination thereof.

[0012] In a second aspect, the present disclosure provides an ingestible composition comprising a vanillyl ether compound, wherein the vanillyl ether compound is a compound of Formula (I) or an edible acceptable salt thereof as described above, and one or more bitter or astringent tastants, such as caffeine, tannins, compounds from coffee, compounds from ginseng, non-animal proteins (e.g., pea protein, soy protein, potato protein, or algal protein), animal proteins (e.g., whey protein or casein protein), citrus fruits or juices, and high intensity sweeteners (e.g., saccharin, steviol glycosides, aspartame), and the like. In some embodiments, the ingestible composition is encapsulated.

[0013] In a third aspect, the present disclosure provides a flavored product comprising the ingestible composition of the second aspect. In some embodiments, the flavored product is a food product, a beverage product, an oral care product, or a pharmaceutical product or a nutraceutical product.

[0014] Further aspects and embodiments thereof are set out in the following detailed description, drawings, abstract and claims. BRIEF DESCRIPTION OF DRAWINGS

[0015] The accompanying drawings are included to provide illustration and a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and, together with the description, serve to explain the principles of the application. In the drawings:

[0016] Figure 1 Chemical formula representing a vanillyl ether compound is shown, wherein R 1 is methyl or ethyl; and R 2 is C 1-8 alkyl or C 3-8 cycloalkyl. DETAILED DESCRIPTION

[0017] The following detailed description illustrates various aspects and embodiments provided herein. This description will be read in connection with the appropriate drawings. The description is not necessarily exhaustive and does not limit the application to the precise embodiments disclosed.

[0018] Definitions

[0019] Unless otherwise defined herein, the following terms and phrases have the indicated meanings. The present disclosure can employ other terms and phrases not expressly defined herein. Such other terms and phrases have the meanings that they possess in the context of the present disclosure as understood by one of ordinary skill in the art. In some cases, a term or phrase can be defined in the singular or plural. In such cases, it is to be understood that the singular form of any term can include its plural form and vice versa, unless expressly indicated to the contrary.

[0020] The term “vanillyl ether compound” refers to a compound of Formula (I) or any comestibly acceptable salt thereof.

[0021] The term “sweetener” or “sweet flavoring agent” or “sweet flavor entity” or “sweetness- imparting compound” or “sweetness tastant” herein refers to a compound that elicits a detectable sweet taste in a subject, e.g., a compound that activates T1R2 / T1R3 taste receptors in vitro.

[0022] The term "bitter compound" or "bitter tastant" herein refers to a compound that elicits a detectable bitter taste in a subject, e.g., a compound that activates one or more T2R taste receptors in vitro. In many cases, such compounds will induce astringency.

[0023] As used herein, "C a to C b " or "C a-b " means the number of carbon atoms in the specified group. That is, the group can contain from "a" to "b" (inclusive) carbon atoms. Thus, for example, "C1to C4alkyl" or "C 1-4 alkyl" means all alkyl groups having from 1 to 4 carbons, i.e., CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, CH3CH2CH2CH2-, CH3CH2CH(CH3)- and (CH3)3C-.

[0024] As used herein, "alkyl" refers to a straight or branched chain hydrocarbon chain (i.e., containing no double or triple bonds) that is completely saturated. In some embodiments, the alkyl group has from 1 to 20 carbon atoms (whenever it appears in the 1-4 alkyl" or a similar name. By way of example only, "C 1-4 alkyl" denotes that there are from 1 to 4 carbon atoms present in the alkyl chain, i.e., the alkyl chain is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and t-butyl. Typical alkyl groups include, but are in no way limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, and the like. Unless indicated to the contrary, the term "alkyl" refers to groups that are unsubstituted.

[0025] As used herein, "cycloalkyl" refers to a non-aromatic, saturated ring or ring system containing only carbon atoms in the ring system backbone. Cycloalkyl groups can be referred to as "C 3-8 cycloalkyl" or a similar name. Examples of cycloalkyl rings include, but are in no way limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, adamantyl, and spiro[4.4]nonanyl. Unless indicated to the contrary, the term "cycloalkyl" refers to groups that are unsubstituted.

[0026] It should be understood that the nomenclature of certain radicals can include either a single radical or a diradical, depending on the context. For example, when a substituent is identified as requiring two points of attachment to the remainder of the molecule, it should be understood that the substituent is a diradical. For example, substituents identified as alkyl groups requiring two points of attachment include diradicals such as -CH2-, -CH2CH2-, -CH2CH(CH3)CH2-, and the like.

[0027] Whenever a substituent is described as a diradical (i.e., having two points of attachment to the remainder of the molecule), it should be understood that the substituent can be attached in either orientation, unless otherwise specified. Thus, for example, a substituent represented as -AE- or includes substituents in which A is attached at the leftmost point of attachment to the molecule and A is attached at the rightmost point of attachment to the molecule.

[0028] 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" covers a single substituent as well as two or more substituents, and so forth.

[0029] As used herein, "for example," "for instance," "such as," or "including" are meant to introduce examples that further clarify more general expressio s. Unless otherwise noted, providing such examples is merely an aid to understanding the illustrated embodiments in this disclosure, and is not meant to confine the disclosed embodiments in any way. These phrases do not mean that the disclosed embodiments are limited to only those examples that are described.

[0030] As used herein, "comprise," "comprises," "comprising," "containing," "include," "includes," "including" and "comprised of" refer to open-ended groups, meaning that the group can include other members in addition to those expressly stated. For example, the phrase "includes A" means that A must be present, but that other members can be present as well. The terms "comprising," "having," and "including" and grammatical variations thereof have the same meaning. In contrast, "consisting of" or "consisting" or "consists" refers to closed groups. For example, the phrase "consisting of A" means that A must be present, and there can be nothing else present.

[0031] As used herein, "optionally" means that the event or circumstance subsequently described can or can not occur. In some embodiments, the optional event does not occur. In some other embodiments, the optional event does occur one or more times.

[0032] As used herein, “or” is to be given its broadest reasonable interpretation, and is not limited to an either / or construction. Thus, the phrase “comprising A or B” means that A can be present and B can be absent, or B can be present and A can be absent, or both A and B can be present. Also, for example, if A defines a class that can have multiple members (e.g., A1 and A2), one or more members of the class can be present simultaneously.

[0033] Other terms are defined elsewhere in this specification, even if not included in this subsection.

[0034] Vanillyl ether compounds

[0035] The uses, methods, compositions, and articles of manufacture disclosed herein relate to vanillyl ether compounds, and primarily to compositions containing plant protein or stevia-derived sweeteners. The vanillyl ether compounds are compounds of Formula (I):

[0036]

[0037] wherein:

[0038] R 1 is a methyl or ethyl group; and

[0039] R 2 is a hydrogen atom, a C 1-8 alkyl group, or a C 3-8 cycloalkyl group, or -CH2-(phenyl), wherein the phenyl moiety is optionally substituted one to two times with substituents independently selected from -OH and -OCH3.

[0040] The variable R 1 may have any suitable value, depending on the above definitions. In some embodiments, R 1 is a methyl group. In some embodiments, R 1 is an ethyl group.

[0041] The variable R 2 may have any suitable value, depending on the above definitions. In some embodiments, R 2 is a C 1-8 alkyl group. In some such embodiments, R 2 is a methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, butan-2-yl, pentan-2-yl, hexan-2-yl, isobutyl, 2-methylbutyl, isopentyl, or pentan-3-yl group. In some embodiments, R 2 is an ethyl or butyl group. In some embodiments, R 2 is an ethyl group. In some other embodiments, R 2 is a C 3-8cycloalkyl, such as cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl. In some embodiments, R 2 is cyclopentyl or cyclohexyl. In some other embodiments, R 2 is a hydrogen atom. In some other embodiments, R 2 is -CH2-(phenyl), wherein the phenyl moiety is optionally substituted one to two times with substituents independently selected from -OH and -OCH3. In some such embodiments, R 2 is benzyl. In some other such embodiments, R 2 is -CH2-(phenyl), wherein the phenyl moiety is substituted at the 3- or 4-position with at least one or two substituents independently selected from -OH and -OCH3.

[0042] Table 1 below lists examples of various vanillyl ether compounds according to certain embodiments. Each compound is itself a separate embodiment of a vanillyl ether compound.

[0043] Table 1

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051] In some embodiments, the safrole-based ether compound is any one of the compounds listed in Table 1. In some embodiments, the safrole-based ether compound is compound 101. In some embodiments, the safrole-based ether compound is compound 102. In some embodiments, the safrole-based ether compound is compound 103. In some embodiments, the safrole-based ether compound is compound 104. In some embodiments, the safrole-based ether compound is compound 105. In some embodiments, the safrole-based ether compound is compound 106. In some embodiments, the safrole-based ether compound is compound 107. In some embodiments, the safrole-based ether compound is compound 108. In some embodiments, the safrole-based ether compound is compound 109. In some embodiments, the safrole-based ether compound is compound 110. In some embodiments, the safrole-based ether compound is compound 111. In some embodiments, the safrole-based ether compound is compound 112. In some embodiments, the safrole-based ether compound is compound 113. In some embodiments, the safrole-based ether compound is compound 114. In some embodiments, the safrole-based ether compound is compound 115. In some embodiments, the safrole-based ether compound is compound 116. In some embodiments, the safrole-based ether compound is compound 117. In some embodiments, the safrole-based ether compound is compound 118. In some embodiments, the safrole-based ether compound is compound 119. In some embodiments, the safrole-based ether compound is compound 120. In some embodiments, the safrole-based ether compound is compound 121. In some embodiments, the safrole-based ether compound is compound 122. In some embodiments, the safrole-based ether compound is compound 123. In some embodiments, the safrole-based ether compound is compound 124. In some embodiments, the safrole-based ether compound is compound 125. In some embodiments, the safrole-based ether compound is compound 126. In some embodiments, the safrole-based ether compound is compound 127. In some embodiments, the safrole-based ether compound is compound 128. In some embodiments, the safrole-based ether compound is compound 129. In some embodiments, the safrole-based ether compound is compound 130. In some embodiments, the safrole-based ether compound is compound 131. In some embodiments, the safrole-based ether compound is compound 132. In some embodiments, the safrole-based ether compound is compound 133. In some embodiments, the safrole-based ether compound is compound 134. In some embodiments, the safrole-based ether compound is compound 135. In some embodiments, the safrole-based ether compound is compound 136. In some embodiments, the safrole-based ether compound is compound 137. In some embodiments, the safrole-based ether compound is compound 138.In some embodiments, the safrole-based ether compound is Compound 139. In some embodiments, the safrole-based ether compound is Compound 140. In some embodiments, the safrole-based ether compound is Compound 141. In some embodiments, the safrole-based ether compound is Compound 142. In some embodiments, the safrole-based ether compound is Compound 143. In some embodiments, the safrole-based ether compound is Compound 144. In some embodiments, the safrole-based ether compound is Compound 145. In some embodiments, the safrole-based ether compound is Compound 146. In some embodiments, the safrole-based ether compound is Compound 147. In some embodiments, the safrole-based ether compound is Compound 148.

[0052] Isotopes can be present in any of the safrole-based ether compounds described. Each of the chemical elements of compounds represented in the structures herein is intended to mean any isotopic form of the element, including but not limited to isotopic forms such as hydrogen-1 (protium), hydrogen-2 (deuterium), and hydrogen-3 (tritium). Thus, reference herein to a compound encompasses all potential isotopic forms of the compound, unless the context clearly indicates otherwise.

[0053] In some embodiments, the safrole-based ether compounds are capable of forming acid and / or base salts due to the presence of amino and / or carboxyl groups or groups similar thereto. Edibly 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. Edibly acceptable salts can be formed with inorganic bases and organic bases. Inorganic bases from which salts can be derived include, for example, alkali metal, alkaline earth metal, aluminum, zinc, copper, manganese, and ammonium hydroxides; particularly preferred are ammonium, potassium, sodium, calcium, and magnesium salts. In some embodiments, treatment of the safrole-based ether compounds disclosed herein with inorganic bases results in the loss of a labile hydrogen from the compound, resulting in the formation of a salt comprising an inorganic cation such as Li + , Na + , K + , Mg 2+ , and Ca 2+Salt forms of the vanillyl ether compounds can be derived from inorganic acids such as, for example, hydrochloric, sulfuric, nitric, phosphoric, sulfamic, and the like; from organic acids such as, for example, oxalic, tartaric, citric, malic, lactic, pyruvic, ascorbic, succinic, malonic, salicylic, propionic, glycolic, skatolic, formic, benzoic, acetic, methanesulfonic, benzenesulfonic, and the like; and from organic bases such as, for example, isopropylamine, trimethylamine, diethylamine, triethylamine, thpropanolamine, and the like; and the like. In some embodiments, the salt is a food-acceptable salt, which is a salt suitable for inclusion in an ingestible composition, such as a food or beverage product.

[0054] In some embodiments, the vanillyl ether compound is in its free (non-salt) form. In other embodiments, the vanillyl ether compound is a food-acceptable salt of any of the above compounds.

[0055] In some embodiments, the vanillyl ether compound is present in a crystalline solid form, either in substantially pure form or in the form of a formulation such as those described below. The crystalline solid can have any suitable polymorphic form, such as any polymorphic form that can be obtained by recrystallization in any suitable solvent system, according to techniques commonly used in the art of polymorph screening.

[0056] In some other embodiments, the vanillyl ether compound is present in an amorphous or semi-amorphous solid form, meaning that it lacks any regular crystal structure. Such a solid can be produced using standard techniques such as spray drying and the like.

[0057] In some embodiments, the vanillyl ether compound is present in the form of a solvate, which is a pseudo-polymorphic form of the compound in which one or more solvent molecules (e.g., water molecules) are absorbed into the crystal 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-propanediol, 1,3-propanediol, and the like. In some embodiments, the present disclosure provides a hydrate of the vanillyl ether compound. Such solvates can be produced by any suitable means, such as those commonly used by the skilled person in the art of polymorph and solvate screening.

[0058] In some other embodiments, the vanillyl ether compound is present as a co-crystal with one or more other compounds, such as one or more other sweetener compounds. The vanillyl ether compound can form a co-crystal with any suitable compound. Non-limiting examples of such suitable compounds include fructose, glucose, galactose, sucrose, lactose, maltose, allulose, sugar alcohols (e.g., erythritol, sorbitol, xylitol, and the like), sucralose, steviol glycosides (e.g., rebaudioside A, rebaudioside B, rebaudioside D, rebaudioside E, rebaudioside M, and the like natural stevioside compounds), other mogrosides (e.g., mogroside V, isomogroside V, siamenoside I, isomogroside III EAspartame, saccharin, acesulfame potassium, cyclamate, inulin, isomalt, and maltitol. Such co-crystals can be produced by any suitable means, such as those set forth in U.S. Patent Application Publication No. 2018 / 0363074, which is incorporated herein by reference.

[0059] In some embodiments, the vanillyl ether compound is in the form of a dry granulate. Such dry granulates can be formed by standard techniques in the art, such as dry granulation, wet granulation, and the like. Such granulates can also include a number of excipients, including inert diluents, such as calcium carbonate, sodium carbonate, lactose, calcium and sodium phosphates; granulating and disintegrating agents, such as starch, cellulose 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 commonly used in food and beverage products can also be included, such as typical food materials.

[0060] In some embodiments, the vanillyl ether compound is in the form of a liquid solution or liquid suspension. Such compositions can also include: carboxymethylcellulose, methylcellulose, hydroxypropylmethylcellulose, sodium alginate, polyvinylpyrrolidone, tragacanth, and acacia; dispersing or wetting agents can be a naturally occurring phosphatide, such as lecithin, or an alkyl ether of a partial glyceride of fatty acids, such as polyoxyethylene stearate, or a condensation product of an alkylene oxide with a fatty acid, such as polyoxyethylene stearate, or a condensation product of an alkylene oxide with a partial ester derived from fatty acids and a hexitol, such as polyoxyethylene sorbitol monooleate, or a condensation product of an alkylene oxide with a partial ester derived from fatty acids and a hexitol anhydride, such as polysorbate monooleate. Such compositions can also include one or more colorants, one or more flavoring agents, and the like. Such liquid suspensions and solutions have a liquid carrier. Typically, the liquid carrier comprises water. In some such cases, the liquid composition is an emulsion, such as an oil-in-water or water-in-oil emulsion. Further, in some cases, water can be too polar to dissolve the vanillyl ether compound to the desired concentration. In such cases, it can be desirable to introduce a water-miscible solvent, such as an alcohol, a glycol, a polyol, and the like, into the solvent to enhance the solubility of the vanillyl ether compound.

[0061] In some embodiments, the vanillyl ether compound is in the form of a solution, i.e., solvated in a liquid carrier. In some embodiments, the liquid carrier is an aqueous carrier. Such solutions can be diluted to any suitable concentration.

[0062] Uses and methods

[0063] In certain aspects, the present disclosure provides the use of a vanillyl ether compound for modifying the flavor of an ingestible composition. In some embodiments, the use for modifying flavor includes a use for reducing bitterness, a use for reducing astringency, a use for reducing a lingering aftertaste (e.g., a lingering sweet aftertaste), or any combination thereof. In some embodiments, the use for modifying flavor is a use for reducing bitterness. In some embodiments, the use for modifying flavor is a use for reducing astringency. In some embodiments, the use for modifying flavor is a use for reducing a lingering aftertaste (e.g., a lingering sweet aftertaste). In some embodiments, the use for modifying flavor is a use for enhancing mouthfeel. In some embodiments, the use for modifying flavor is a use for reducing the perceived intensity of an off-flavor.

[0064] In related aspects, the present disclosure provides a method of modifying the flavor of an ingestible composition, the method comprising introducing a vanillyl ether compound into the ingestible composition. In some embodiments, modifying flavor means reducing bitterness, reducing astringency, reducing a lingering (e.g., a lingering sweet) aftertaste, or any combination thereof. In some embodiments, modifying flavor means reducing bitterness. In some embodiments, modifying flavor means reducing astringency. In some embodiments, modifying flavor means reducing a lingering (e.g., a lingering sweet) aftertaste. In some embodiments, modifying flavor means reducing the perceived intensity of an off-flavor. In some embodiments, modifying flavor means enhancing mouthfeel (including reducing the perceived chalkiness or grittiness).

[0065] In some embodiments, the ingestible composition comprises a vanillyl ether compound and one or more bitter or astringent tastants, such as caffeine, tannins, compounds from coffee, compounds from ginseng, non-animal proteins (e.g., pea protein, soy protein, potato protein, or algal protein), animal proteins (e.g., whey protein or casein protein), citrus fruits or juices, and high intensity sweeteners (e.g., saccharin, steviol glycosides, aspartame, etc.). In some embodiments, the bitter or astringent tastant is a plant protein, such as pea protein or soy protein.

[0066] The vanillyl ether compound can be used in or introduced into the ingestible composition at any suitable concentration. In some embodiments, the vanillyl ether compound is used in or introduced into the ingestible composition at a concentration ranging from 0.01 ppm to 1000 ppm, or from 0.05 ppm to 500 ppm, or from 0.1 ppm to 250 ppm, or from 0.1 ppm to 100 ppm, or from 0.1 ppm to 50 ppm, or from 0.1 ppm to 20 ppm, or from 0.1 ppm to 10 ppm, based on the total dry weight of the ingestible composition.

[0067] Further embodiments regarding the ingestible composition are set forth in the following sections, any of which can be combined with the embodiments set forth in this section.

[0068] Ingestible compositions

[0069] In certain aspects, the present disclosure provides an ingestible composition comprising a vanillyl ether compound and one or more bitter or astringent tastant, such as caffeine, tannins, compounds from coffee, compounds from ginseng, non-animal proteins (e.g., pea protein, soy protein, potato protein, or algal protein), animal proteins (e.g., whey protein or casein protein), citrus fruits or juices, and high intensity sweeteners (e.g., saccharin, steviol glycosides, aspartame, neotame, acesulfame potassium, mogrosides), and the like.

[0070] In some embodiments, the bitter or astringent tastant is a plant protein, an algal protein, or any combination thereof. In some embodiments, the bitter or astringent tastant is a plant protein. Any suitable plant protein can be used. Some non-limiting examples of such plant proteins include pea protein, soy protein, almond protein, cashew protein, canola (rapeseed) protein, chickpea protein, fava bean protein, sunflower seed protein, mung bean protein, red lentil protein, wheat protein, oat protein, potato protein, and any combination thereof. In some embodiments, the plant protein is pea protein, soy protein, or any combination thereof. In some other embodiments, the bitter or astringent tastant is an algal protein, such as a protein from a microalgae (e.g., Spirulina or Chlorella) or a macroalgae (e.g., seaweed). In some embodiments, the bitter or astringent tastant is seaweed powder.

[0071] The ingestible composition can comprise any suitable concentration of plant protein. In some embodiments, the ingestible composition comprises a concentration ranging from 0.1 wt% to 15 wt%, or from 0.5 wt% to 12 wt%, or from 1 wt% to 10 wt% of plant protein, based on the total dry weight of the ingestible composition.

[0072] In some embodiments, the bitter or astringent tastant is a steviol glycoside compound, such as a stevia extract or a compound such as stevioside, rebaudioside A, rebaudioside D, rebaudioside M, or any combination thereof. The ingestible composition can comprise any suitable concentration of steviol glycoside. In some embodiments, the ingestible composition comprises a concentration ranging from 1 ppm to 5000 ppm, or from 5 ppm to 1000 ppm, or from 50 ppm to 1000 ppm, or from 100 ppm to 500 ppm of steviol glycoside, based on the total weight of the ingestible composition.

[0073] The ingestible compositions disclosed herein (including those mentioned in various uses and methods) can comprise any number of additional ingredients. Such embodiments will be set forth in greater detail below.

[0074] In certain particular embodiments, the ingestible composition comprises sodium (i.e., sodium cations, which can be replaced by potassium cations). In some such embodiments, the introduction of the vanillyl ether compound allows for the use of less sodium (e.g., a reduction of more than 10%, a reduction of more than 20%, a reduction of more than 30%, a reduction of more than 40%, a reduction of 50% of sodium cations, a reduction of more than 60%, or a reduction of more than 70%, or a reduction of more than 80%, or a reduction of more than 90%) and still achieves the taste profile of a comparable product that uses a higher concentration of sodium. In some related embodiments, the use of the vanillyl ether compound allows for the elimination of sodium from the composition. Such ingestible compositions can be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of those specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda, and the like. The sodium can be any suitable source of sodium, such as table salt, sea salt, soy sauce, fish sauce, shrimp paste, butter, miso, and Worcestershire sauce.

[0075] In certain instances, the amount of sugar in a product can be reduced by reducing bitter or astringent tastes. In some such embodiments, the introduction of the vanillyl ether compound allows for the use of less sugar (e.g., a reduction of more than 10%, a reduction of more than 20%, a reduction of more than 30%, a reduction of more than 40%, a reduction of more than 50%, a reduction of more than 60%, or a reduction of more than 70%) and still achieves the taste profile of a comparable product that uses more sugar. The sugar can be any suitable sugar or combination of sugars, including but not limited to sucrose, fructose (e.g., high fructose corn syrup), glucose, rare sugars, or any combination thereof. In some embodiments, the ingestible composition is a food product, such as any of those specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda, and the like.

[0076] In certain cases, the amount of non-sugar sweetener in a product can be reduced by reducing the bitter or astringent taste. In some such embodiments, the introduction of a magnolol-based ether compound allows for the use of less non-sugar sweetener (e.g., reduced by more than 10%, reduced by more than 20%, reduced by more than 30%, reduced by more than 40%, reduced by more than 50%, reduced by more than 60%, or reduced by more than 70%) and still achieves the taste profile of a comparable product that uses more non-sugar sweetener. The non-sugar sweetener can be any suitable sugar or combination of sugars, including but not limited to sucralose, rebaudioside (e.g., rebaudioside A, rebaudioside D, rebaudioside E, rebaudioside M, or any combination thereof), acesulfame potassium, a sugar alcohol (e.g., erythritol), aspartame, neotame, cyclamate, mogroside (e.g., mogroside III, mogroside IV, mogroside V, siamenoside I, iso-mogroside V, mogroside IVE, iso-mogroside IV, iso-mogroside IVE, mogroside IIIE, 11-oxo-mogroside V, 1,6-alpha anomer of siamenoside I, or any combination thereof), or any combination thereof. In some embodiments, the ingestible composition is a food product, such as any of those specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda, etc. In some such embodiments, the non-sugar sweetener is rebaudioside.

[0077] In certain embodiments of any of the aspects and embodiments set forth herein relating to ingestible compositions, the ingestible composition is a non-naturally occurring product, such as a composition specifically manufactured for the production of a flavored product, such as a food or beverage product.

[0078] In some embodiments, the ingestible composition comprises a sweetener. The sweetener may be present in the ingestible composition at any suitable concentration. For example, in some embodiments, the sweetener is present in an amount of 0.1% to 12% by weight. In some embodiments, the sweetener is present in an amount of 0.2% to 10% by weight. In some embodiments, the sweetener is present in an amount of 0.3% to 8% by weight. In some embodiments, the sweetener is present in an amount of 0.4% to 6% by weight. In some embodiments, the sweetener is present in an amount of 0.5% to 5% by weight. In some embodiments, the sweetener is present in an amount of 1% to 2% by weight. In some embodiments, the sweetener is present in an amount of 0.1% to 5% by weight. In some embodiments, the sweetener is present in an amount of 0.1% to 4% by weight. In some embodiments, the sweetener is present in an amount of 0.1% to 3% by weight. In some embodiments, the sweetener is present in an amount of 0.1% to 2% by weight. In some embodiments, the sweetener is present in an amount of 0.1% to 1% by weight. In some embodiments, the sweetener is present in an amount of 0.1% to 0.5% by weight. In some embodiments, the sweetener is present in an amount of 0.5% to 10% by weight. In some embodiments, the sweetener is present in an amount of 2% to 8% by weight. In some further embodiments of the embodiments set forth in this paragraph, the sweetener is sucrose, fructose, glucose, xylitol, erythritol, or a combination thereof.

[0079] In some other embodiments, lower concentrations of sweetener may be more suitable. For example, in some embodiments, the sweetener is present in an amount of 10 ppm to 1000 ppm. In some embodiments, the sweetener is present in an amount of 20 ppm to 800 ppm. In some embodiments, the sweetener is present in an amount of 30 ppm to 600 ppm. In some embodiments, the sweetener is present in an amount of 40 ppm to 500 ppm. In some embodiments, the sweetener is present in an amount of 50 ppm to 400 ppm. In some embodiments, the sweetener is present in an amount of 50 ppm to 300 ppm. In some embodiments, the sweetener is present in an amount of 50 ppm to 200 ppm. In some embodiments, the sweetener is present in an amount of 50 ppm to 150 ppm. In some further embodiments of the embodiments set forth in this paragraph, the sweetener is steviol glycoside, mogroside, a derivative of any of the above, such as a glycoside derivative (e.g., a glucosyl compound), or any combination thereof.

[0080] The composition can include any suitable sweetener or combination of sweeteners. In some embodiments, the sweetener is a common saccharide sweetener, such as sucrose, fructose, glucose, and sweetener compositions including 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. In some other embodiments, the sweetener is selected from rare natural sugars including D-allose, D- psicose, L-ribose, D-tagatose, L-glucose, L-fucose, L-arabinose, D-turanose, and D- leucrose. In some embodiments, the sweetener is selected from semi-synthetic “sugar alcohol” sweeteners such as erythritol, isomalt, lactitol, mannitol, sorbitol, xylitol, maltodextrin, and the like. In some embodiments, the sweetener is selected from artificial sweeteners such as aspartame, saccharin, acesulfame potassium, cyclamate, sucralose, and alitame. In some embodiments, the sweetener is selected from the group consisting of cyclamic acid, mogrosides, tagatose, maltose, galactose, mannose, sucrose, fructose, lactose, neotame and other aspartame derivatives, glucose, D-tryptophan, glycine, maltitol, lactitol, isomalt, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolysate (HSH), stevioside, rebaudioside A, other steviol glycosides, chemically modified steviol glycosides (such as glucosylated steviol glycosides), other mogrosides, chemically modified mogrosides (such as glucosylated mogrosides), carrelame and other guanidino sweeteners. In some embodiments, the sweetener is a combination of two or more sweeteners set forth in this paragraph. In some embodiments, the sweetener can be a combination of two, three, four, or five sweeteners disclosed herein. In some embodiments, the sweetener can be a sugar. In some embodiments, the sweetener can be a combination of one or more sugars and other natural and artificial sweeteners. In some embodiments, the sweetener is a sugar. In some embodiments, the sugar is a canesugar. In some embodiments, the sugar is a sugar beet sugar. In some embodiments, the sugar can be sucrose, fructose, glucose, or a combination thereof. In some embodiments, the sugar can be sucrose. In some embodiments, the sugar can be a combination of fructose and glucose.

[0081] Sweeteners can also include, for example, sweetener compositions comprising one or more natural or synthetic carbohydrates, such as corn syrup, high fructose corn syrup, high maltose corn syrup, glucose syrup, sucralose syrup, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolysate (HSH), or other syrups or sweetener concentrates from natural fruit and vegetable sources, or semi-synthetic "sugar alcohol" sweeteners, such as polyols. In some embodiments, non-limiting examples of polyols include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomaltitol, propylene glycol, glycerol (glycerin), threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, reduced glucose syrup, isomaltulose, maltodextrin, and the like, as well as sugar alcohols or any other carbohydrates capable of being reduced that do not adversely affect taste, or combinations thereof.

[0082] Sweeteners can be natural or synthetic sweeteners, including but not limited to agave inulin, agave nectar, agave syrup, amazake, brazzein, brown rice syrup, coconut crystals, coconut sugar, coconut sugar syrup, date sugar, fructans (also known as inulin fiber, fructo-oligosaccharides, or oligofructose), green stevia inulin, 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 steviol glycosides, stevioside, stevioside extract, honey, Jerusalem artichoke syrup, licorice root, luo han guo (fruit, powder, or extract), lucuma (fruit, powder, or extract), maple tree sap (including, for example, sap extracted from sugar maple (Acer saccharum), black maple (Acer nigrum), red maple (Acer rubrum), silver maple (Acer saccharinum), Norway maple (Acer platanoides), box elder (Acer negundo), bigleaf maple (Acer macrophyllum), Acer grandidentatum, Rocky Mountain maple (Acer glabrum), Acer mono), maple syrup, maple sugar, pecan tree sap (including, for example, sap extracted from white pecan (Juglans cinerea), black pecan (Juglans nigra), J. ailatifolia, English walnut (Juglans regia)), birch tree sap (including, for example, sap extracted from paper birch (Betula papyrifera), yellow birch (Betula alleghaniensis), sweet birch (Betula lenta), river birch (Betula nigra), gray birch (Betula populifolia), pendula birch (Betula pendula)), sycamore sap (for example, sap extracted from American sycamore (Platanus occidentalis)), ironwood sap (for example, sap extracted from American ironwood (Ostrya virginiana)), mascobado, molasses (for example, blackstrap molasses), molasses sugar, monatin, monellin, cane sugar, chayote (Sechium edule) syrup, chikoo (Sapindus saponaria) syrup, chitén (Chilopsis linearis) syrup, chufa (Cyperus esculentus) syrup, coconut water, coffeeberry (Coffea arabica) syrup, corn syrup, corn syrup solids, date (Phoenix dactylifera) syrup, dandelion (Taraxacum officinale) syrup, dandelion (Taraxacum officinale) honey, dandelion (Taraxacum officinale) nectar, dandelion (Taraxacum officinale) sap, dandelion (Taraxacum officinale) sugar, dandelion (Taraxacum officinale) syrup, date (Phoenix dactylifera) syrup, date (Phoenix dactylifera) sugar, date (Phoenix dactylifera) nectar, date (Phoenix dactylifera) sap, date (Phoenix dactylifera) honey, dextrin, dihydrochalcone, dihydroquercetin, dihydroxychalcone, dihydroxyphenyl propionate, dihydroxypropyl, dihydroxypropyl phenyl propionate, dihydroxypropyl phenyl propionate, dihydroxypropyl phenyl propionate, dihydroxypropyl phenyl propionate, dihydroxypropyl phenyl propionate, dihydroxypropyl phenyl propionate, dihydroxypropyl phenyl propionate, dihydroxypropyl phenyl propionate, dihydroxypropyl phenyl propionate, dihydroxypropyl phenyl propionate,sugar) (also known as natural sugar, unrefined glycosaccharide or sucrose), palm sugar, panocha, piloncillo, rapadura, gur, jaggery, rice syrup, sorghum, sorghum syrup, tapioca syrup (also known as tapioca starch syrup), thaumatin, yacon root, malt syrup, barley malt syrup, barley malt flour, beet sugar, cane sugar, crystalline fruit juice crystals, caramel, carbitol, carob syrup, castor sugar, hydrolates, hydrolyzed canned fruit juice, hydrolyzed starch, invert sugar, anise camphor, arabinogalactan, arrope, sugar syrup, P-4000, acesulfame potassium (also known as acesulfame potassium or ace-K), alitame (also known as aclame), advantame, aspartame, baiyunosdie, neotame, benzamide derivatives, bernadame, canderel, carrelame and other guanidine-based sweeteners, plant fibers, corn sugar, coupled sugar, curculin, cyclamates, cyclocaryoside I (cyclocaryoside II), dextrin, dihydrochalcone, dihydroxyacetone, dipeptide-based sweeteners, diplomat, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethylphosphonate, ethI) Demerara, dextran, dextrin, diastatic malt, dulcin, sucrol, valzin, dulcogenin A, dulcogenin B, emulin, enoxolone, maltodextrin, saccharin, estragole, ethyl maltol, glucin, gluconate, gluconolactone, glucosamine, glucuronic acid, glycerol, glycyphillin, glycyrrhizin, glycyrrhizin monoglucuronide, golden sugar, yellow sugar, golden syrup, granulated sugar, Gynostemma pentaphyllum, hernandulcin, isomerized liquid sugar, jallab, chicory root dietary fiber, kynurenine derivatives (including N) '-Formyl-kynurenine, N'-acetyl-kynurenine, 6-chloro-kynurenine), galactitol, litesse, ligicane, lycasin, N-(4-cyanophenyl)-N-(2,3-methylenedioxybenzyl)guanidinacetic acid, guanidine, farernum syrup, areca nut protein I, areca nut protein II, maltol, crystalline maltitol, maltodextrin, maltotriol, mannosamine, miraculin, mizuame, mogrosides (including, for example, mogroside IV, mogroside V and neomogroside), mukurozioside, nanosugars sugar), naringin dihydrochalcone, neohesperidin dihydrochalcone, raw sugar (nib sugar), black oligosaccharides, norbu, almond syrup, osladin, pekmez, pentadin, periandrin I, perillartine, petphyllum, phenylalanine, phloisosideside I, phlorodizin, phyllodulcin, polyglycitol syrup, polypodoside A, pterocaryoside A, pterocaryoside B, rebiana, refined syrup, rub syrup, rubusoside, selligueain A A) Shugr, ciprofloxacin I, and siraitiaGrosvenorii), soybean oligosaccharides, Splenda, SRIoxime V, steviol glycosides, steviolbioside, stevioside, strogins 1, 2, and 4, sucronic acid, sucrononate, sugar, sodium suosan, phloridzin, super aspartame, tetrasaccharide, threitol, treacle, trilobtain, tryptophan and derivatives (6-trifluoromethyl-tryptophan, 6-chloro-D-tryptophan), vanillin sugar, volemitol, xylitol, xylitol, xylitol, and combinations or blends of any two or more thereof.

[0083] In other embodiments, the sweetener can be a chemically or enzymatically modified natural high-potency sweetener. Modified natural high-potency sweeteners include glycosylated natural high-potency sweeteners, such as glucosyl, galactosyl, or fructosyl derivatives containing from 1 to 50 glycosyl residues. Glycosylated natural high-potency sweeteners can be prepared by enzymatic transglycosylation reactions catalyzed by various enzymes having transglycosylation activity. In some embodiments, the modified sweetener can be substituted or unsubstituted.

[0084] Additional sweeteners also include combinations of any two or more of any of the foregoing sweeteners. In some embodiments, the sweetener can comprise a combination of two, three, four, or five sweeteners disclosed herein. In some embodiments, the sweetener can be a sugar. In some embodiments, the sweetener can be a combination of one or more sugars with other natural and artificial sweeteners. In some embodiments, the sweetener is a caloric sweetener, such as sucrose, fructose, xylitol, erythritol, or combinations thereof. In some embodiments, the ingestible composition is free (or in some embodiments, substantially free) of stevia-derived sweeteners, such as steviol glycosides, glucosylated steviol glycosides, or rebaudioside.

[0085] In certain embodiments, the ingestible composition can comprise any additional ingredient or combination of ingredients commonly used in food and beverage products, including but not limited to:

[0086] acids, including, for example, citric acid, phosphoric acid, ascorbic acid, sodium bisulfate, lactic acid, or tartaric acid;

[0087] bittering ingredients, including, for example, caffeine, quinine, green tea, catechins, polyphenols, robusta green coffee extract, green coffee extract, potassium chloride, menthol, or proteins (such as proteins from plants, algae, or fungi and protein isolates);

[0088] Colorants, 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;

[0089] Preservatives, including, for example, sodium benzoate, potassium benzoate, potassium sorbate, sodium metabisulfite, sorbic acid, or benzoic acid;

[0090] Antioxidants, including, for example, ascorbic acid, calcium disodium EDTA, alpha-tocopherol, mixed tocopherols, rosemary extract, grape seed extract, resveratrol, or sodium hexametaphosphate;

[0091] Vitamins or functional ingredients, including, for example, resveratrol, Co-Q10, omega 3 fatty acids, theanine, choline chloride (Citocoline), inositol, inulin (chicory root), taurine, ginseng extract, guarana extract, ginger extract, L-phenylalanine, L-carnitine, L-tartrate, D-glucuronolactone, inositol, bioflavonoids, echinacea, Ginkgo Biloba, yerba mate, flaxseed oil, Garcinia cambogia peel extract, white tea extract, ribose, milk thistle extract, grape seed extract, pyridoxal hydrochloride (vitamin B6), cyanocobalamin (vitamin B12), niacinamide (vitamin B3), biotin, calcium lactate, calcium pantothenate (pantothenic acid), calcium phosphate, calcium carbonate, chromium chloride, chromium polynicotinate, copper 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 sulfate;

[0092] Clouding agents, including, for example, ester gum, brominated vegetable oil (BVO), or sucrose acetate isobutyrate (SAIB);

[0093] Buffers, including, for example, sodium citrate, potassium citrate, or salt;

[0094] Flavors, including, for example, propylene glycol, ethanol, glycerin, gum arabic (acacia gum), malt dextrin, modified corn starch, dextrose, natural flavoring, natural flavoring with other natural flavoring (natural flavoring WONF), natural and artificial flavoring, artificial flavoring, silicon dioxide, magnesium carbonate, or tribasic calcium phosphate; or

[0095] Starches and stabilizers, including, for example, gum arabic, xanthan gum, carboxymethylcellulose (CMC), polysorbate 60, polysorbate 80, medium-chain triglycerides, cellulose gel, cellulose gum, sodium caseinate, modified food starch, gum acacia (gum senegal), inulin, or carrageenan.

[0096] The ingestible compositions can have any suitable pH. In some embodiments, the amide compounds enhance the sweetness of a sweetener over a wide range of pH, for example, from a lower pH to a neutral pH. Lower and neutral pH values include, but are not limited to, pH values from 1.5 to 9.0, or 2.5 to 8.5; 3.0 to 8.0; 3.5 to 7.5, and 4.0 to 7; in certain embodiments, the compounds disclosed and described herein, alone or in combination, can enhance the perceived sweetness of a fixed concentration of a sweetener in a taste test at a compound concentration of 50 μΜ, 40 μΜ, 30 μΜ, 20 μΜ, or 10 μΜ at a low to neutral pH. In certain embodiments, the compounds disclosed and described herein, alone or in combination, have a fold enhancement at a lower pH that is substantially similar to the fold enhancement of the compounds at a neutral pH. This consistent sweetness-enhancing property over a wide pH range allows the compounds disclosed and described herein, alone or in combination, to be used widely in a variety of foods and beverages.

[0097] In some embodiments, the ingestible compositions disclosed herein comprise a combination of a vanillyl ether compound with one or more umami or kokumi tastants. Such umami or kokumi tastants include, but are not limited to, N-(heptan-4-yl)-benzo[d][l,3]dioxol-5- carboxamide, N 1 -(2,4-dimethoxybenzyl)-N 2-(2-(pyridin-2-yl)ethyl)-oxalyl amide, alkyl amides, glutamate (e.g., monosodium glutamate (MSG)), arginate, purine ribonucleotides (e.g., inosine monophosphate (IMP), adenosine monophosphate (AMP), guanosine monophosphate (GMP), and their sodium salts), amino acids (e.g., L-threonine), oligopeptides (e.g., glutamyl oligopeptides), cheese and cheese extracts, yeast extract, and alcohol (ethanol). The vanillyl ether compound can be used in combination with such umami or kokumi tastants in any suitable ratio (w / w) ranging from 1 : 1000 to 1000: 1, or 1 : 100 to 100: 1, or 1 : 50 to 50: 1, or 1 : 25 to 25: 1, or 1 : 10 to 10: 1, e.g., 1 : 25, 1 : 24, 1 : 23, 1 : 22, 1 : 21, 1 : 20, 1 : 19, 1 : 18, 1 : 17, 1 : 16, 1 : 15, 1 : 14, 1 : 13, 1 : 12, 1 : 11, 1 : 10, 1 : 9, 1 : 8, 1 : 7, 1 : 6, 1 : 5, 1 : 4, 1 : 3, 1 : 2, 1 : 1, 2: 1, 3: 1, 4: 1, 5: 1, 6: 1, 7: 1, 8: 1, 9: 1, 10: 1, 11 : 1, 12: 1, 13: 1, 14: 1, 15: 1, 16: 1, 17: 1, 18: 1, 19: 1, 20: 1, 21 : 1, 22: 1, 23: 1, 24: 1, or 25: 1.

[0098] In some embodiments, the ingestible compositions disclosed herein comprise a vanillyl ether compound in combination with one or more bitter or astringent tastants. Such bitter or astringent tastants include, but are not limited to, active pharmaceutical ingredients (APIs), tannins (such as those in coffee, tea, or wine), ginseng, vitamins, minerals, limonin or nomilin (such as found in citrus juices), caffeine, quinine, catechins, polyphenols, potassium chloride, menthol, other commonly used oral care ingredients, cooling agents (such as N-ethyl-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, 2-(4-fluorophenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide, 2-(2-hydroxy-4-methylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide, 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide, 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiazol-5-ylmethyl)-acetamide, and 2-((5-methoxybenzofuran-2-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide), vegetable starches or proteins (such as pea protein, soy protein, chickpea protein, bean protein, or potato protein), algal proteins or starches, fungal proteins or starches, or alcohols (ethanol), high intensity sweeteners such as saccharin, steviol glycosides, mogrosides, aspartame, and the like. In some embodiments, the bitter or astringent tastant is a plant protein. In other embodiments, the bitter or astringent tastant is a steviol glycoside compound, such as stevioside, rebaudioside A, rebaudioside D, rebaudioside E, rebaudioside M, or any combination thereof.The vanillyl ether compound can be used in combination with such bitter or astringent tastants in any suitable ratio (w / w) ranging from 1 : 1000 to 1000: 1, or 1 : 100 to 100: 1, or 1 : 50 to 50: 1, or 1 : 25 to 25: 1, or 1 : 10 to 10: 1, for example 1 : 25, 1 : 24, 1 : 23, 1 : 22, 1 : 21, 1 : 20, 1 : 19, 1 : 18, 1 : 17, 1 : 16, 1 : 15, 1 : 14, 1 : 13, 1 : 12, 1 : 11, 1 : 10, 1 : 9, 1 : 8, 1 : 7, 1 : 6, 1 : 5, 1 : 4, 1 : 3, 1 : 2, 1 : 1, 2: 1, 3: 1, 4: 1, 5: 1, 6: 1, 7: 1, 8: 1, 9: 1, 10: 1, 11 : 1, 12: 1, 13: 1, 14: 1, 15: 1, 16: 1, 17: 1, 18: 1, 19: 1, 20: 1, 21 : 1, 22: 1, 23: 1, 24: 1, or 25: 1.

[0099] The ingestible composition according to any of the preceding embodiments, in certain embodiments, further comprises one or more additional flavor modifying compounds, such as a compound that enhances sweet taste (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), a compound that blocks bitter taste, a compound that enhances umami taste, a compound that reduces sour or licorice taste, a compound that enhances salty taste, a compound that enhances cooling effect, or any combination of the foregoing.

[0100] Accordingly, in some embodiments, the ingestible compositions disclosed herein comprise a vanillyl ether compound and one or more sweet taste enhancing compounds. Such sweet taste enhancing compounds include, but are not limited to, 3-((4-amino-2,2-dioxo-1H- benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2,2-dimethyl-N-propyl-propanamide, N-(1-((4-amino-2,2- dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methyl-propan-2-yl)-isonicotinamide, 4-amino- 5,6-dimethylthieno[2,3-d]pyrimidin-2(1H)-one, hesperetin dihydrochalcone, hesperetin dihydrochalcone-4’-O’glucoside, neohesperetin dihydrochalcone, naringenin, naringin, phloretin, glucosylated steviol glycosides, trilobatin, eriodictyol, homoeriodictyol, brazzein, (2R,3R)-3-acetoxy-5,7,4’-trihydroxyflavanone, (2R,3R)-3-acetoxy-5,7,3’-trihydroxy-4’- methoxyflavanone, rebaudioside, or compounds described in, e.g., 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, and U.S. Patent Application Publication No. 2017 / 0119032. In some embodiments, the ingestible compositions comprise phloretin, hesperetin dihydrochalcone, or any combination thereof. The vanillyl ether compound can be used in combination with such other sweet taste enhancing agents in any suitable ratio (w / w) ranging from 1 :1000 to 1000:1, or 1 :100 to 100:1, or 1 :50 to 50:1, or 1 :25 to 25:1, or 1 :10 to 10:1, e.g., 1 :25, 1 :24, 1 :23, 1 :22, 1 :21, 1 :20, 1 :19, 1 :18, 1 :17, 1 :16, 1 :15, 1 :14, 1 :13, 1 :12, 1 :11, 1 :10, 1 :9, 1 :8, 1 :7, 1 :6, 1 :5, 1 :4, 1 :3, 1 :2, 1 :1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11 :1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21 :1, 22:1, 23:1, 24:1, or 25:1. In some embodiments of any of the foregoing embodiments, the vanillyl ether compound is combined with glucosylated steviol glycosides in any of the aforementioned ratios. As used herein, the term “glucosylated steviol glycoside” refers to the product of enzymatic glucosylation of a natural steviol glycoside compound. Glucosylation typically occurs through a glycosidic bond, e.g., an a-1,2 bond, an a-1,4 bond, an a-1.6 bond, a b-1,2 bond, a b-1,4 bond, a b-1,6 bond, etc.

[0101] In some further embodiments, the ingestible compositions disclosed herein comprise a combination of a shikimide compound with one or more umami or kokumi-enhancing compounds. Such umami-enhancing compounds include, but are not limited to, compounds of natural origin, such as (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)-acrylamide, or synthetic compounds, such as N-(heptan-4-yl)-benzo[d][l,3]dioxol-5- carboxamide, N 1 -(2,4-dimethoxybenzyl)-N 2 -(2-(pyridin-2-yl)ethyl)-oxalylamide, alkylamides, or any other compounds described in U.S. Patent Nos. 8,735,081, 8,124,121, and 8,968,708. The shikimide compound can be used in combination with such umami-enhancing agents in any suitable ratio (w / w) ranging from 1:1000 to 1000:1, or 1:100 to 100:1, or 1:50 to 50:1, or 1:25 to 25:1, or 1:10 to 10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1.

[0102] In some further embodiments, the ingestible compositions disclosed herein comprise a combination of a vanillyl ether compound and one or more cooling-enhancing compounds. Such cooling-enhancing compounds include, but are not limited to, compounds of natural origin, such as menthol or its analogs, or synthetic compounds, such as any of the compounds described in U.S. Patent Nos. 9,394,287 and 10,421,727. The vanillyl ether compound can be combined with such umami-enhancing agents in any suitable ratio (w / w) ranging from 1 : 1000 to 1000: 1, or 1 : 100 to 100: 1, or 1 : 50 to 50: 1, or 1 : 25 to 25: 1, or 1 : 10 to 10: 1, such as 1 : 25, 1 : 24, 1 : 23, 1 : 22, 1 : 21, 1 : 20, 1 : 19, 1 : 18, 1 : 17, 1 : 16, 1 : 15, 1 : 14, 1 : 13, 1 : 12, 1 : 11, 1 : 10, 1 : 9, 1 : 8, 1 : 7, 1 : 6, 1 : 5, 1 : 4, 1 : 3, 1 : 2, 1 : 1, 2: 1, 3: 1, 4: 1, 5: 1, 6: 1, 7: 1, 8: 1, 9: 1, 10: 1, 11 : 1, 12: 1, 13: 1, 14: 1, 15: 1, 16: 1, 17: 1, 18: 1, 19: 1, 20: 1, 21 : 1, 22: 1, 23: 1, 24: 1, or 25: 1. In some embodiments, the edible compositions comprise: N-ethyl-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide; N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide; 2-(4-fluorophenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide; 2-(2-hydroxy-4-methylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide; 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide; 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiazol-5-ylmethyl)-acetamide; 2-((5-methoxybenzofuran-2-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide, or any combination of any of the above ratios. In some embodiments, such edible compositions comprise menthol or menthol analogs. In some further embodiments, such edible compositions are compositions for oral care products, such as toothpastes, mouthwashes, whitening compositions, dentifrices, and the like.

[0103] In some further embodiments, the ingestible compositions disclosed herein comprise a combination of a vanillyl ether compound with one or more other bitter blocking compounds. Such bitter blocking compounds include, but are not limited to, 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(3- hydroxybenzyl)-imidazolidine-2,4-dione, N-(7-acetyl-2,3-dihydrobenzo-[b][1,4]dioxepin-6-yl)-2-(4- acetylpiperazin-1-yl)acetamide, or other compounds listed in U.S. Patent Nos. 8,076,491, 8,445,692, and 9,247,759, or in PCT Publication No. WO 2020 / 033669. The vanillyl ether compound can be used in combination with such bitter blockers in any suitable ratio (w / w) ranging from 1:1000 to 1000:1, or 1:100 to 100:1, or 1:50 to 50:1, or 1:25 to 25:1, or 1:10 to 10:1, for example 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1.

[0104] In some further embodiments, the ingestible compositions disclosed herein comprise a combination of a vanillyl ether compound with one or more sour taste modulating compounds. The vanillyl ether compound can be used in combination with such sour taste modulating compounds in any suitable ratio (w / w) ranging from 1:1000 to 1000:1, or 1:100 to 100:1, or 1:50 to 50:1, or 1:25 to 25:1, or 1:10 to 10:1, for example 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1.

[0105] In some further embodiments, the ingestible compositions disclosed herein comprise a combination of a vanillyl ether compound with one or more mouthfeel modifying compounds. Such mouthfeel modifying compounds include, but are not limited to, tannins, cellulosic materials, bamboo powder, and the like. The vanillyl ether compound can be combined with such mouthfeel enhancers in any suitable ratio (w / w) ranging from 1 : 1000 to 1000: 1, or 1 : 100 to 100: 1, or 1 : 50 to 50: 1, or 1 : 25 to 25: 1, or 1 : 10 to 10: 1, such as 1 : 25, 1 : 24, 1 : 23, 1 : 22, 1 : 21, 1 : 20, 1 : 19, 1 : 18, 1 : 17, 1 : 16, 1 : 15, 1 : 14, 1 : 13, 1 : 12, 1 : 11, 1 : 10, 1 : 9, 1 : 8, 1 : 7, 1 : 6, 1 : 5, 1 : 4, 1 : 3, 1 : 2, 1 : 1, 2: 1, 3: 1, 4: 1, 5: 1, 6: 1, 7: 1, 8: 1, 9: 1, 10: 1, 11 : 1, 12: 1, 13: 1, 14: 1, 15: 1, 16: 1, 17: 1, 18: 1, 19: 1, 20: 1, 21 : 1, 22: 1, 23: 1, 24: 1, or 25: 1.

[0106] In some further embodiments, the ingestible compositions disclosed herein comprise a combination of a vanillyl ether compound with one or more flavor masking compounds. Such flavor masking compounds include, but are not limited to, cellulosic materials, materials extracted from fungi, materials extracted from plants, citric acid, carbonic acid (or carbonate), and the like. The vanillyl ether compound can be combined with such mouthfeel enhancers in any suitable ratio (w / w) ranging from 1 : 1000 to 1000: 1, or 1 : 100 to 100: 1, or 1 : 50 to 50: 1, or 1 : 25 to 25: 1, or 1 : 10 to 10: 1, such as 1 : 25, 1 : 24, 1 : 23, 1 : 22, 1 : 21, 1 : 20, 1 : 19, 1 : 18, 1 : 17, 1 : 16, 1 : 15, 1 : 14, 1 : 13, 1 : 12, 1 : 11, 1 : 10, 1 : 9, 1 : 8, 1 : 7, 1 : 6, 1 : 5, 1 : 4, 1 : 3, 1 : 2, 1 : 1, 2: 1, 3: 1, 4: 1, 5: 1, 6: 1, 7: 1, 8: 1, 9: 1, 10: 1, 11 : 1, 12: 1, 13: 1, 14: 1, 15: 1, 16: 1, 17: 1, 18: 1, 19: 1, 20: 1, 21 : 1, 22: 1, 23: 1, 24: 1, or 25: 1.

[0107] In an embodiment, the ingestible composition comprises i) a vanillyl ether compound; ii) a carrier; and iii) optionally at least one adjuvant. The term "carrier" means an auxiliary substance generally inert, such as a solvent, a binder, or other inert medium, which is used in combination with the compound of the present application and one or more optional adjuvants to form a formulation. For example, water or a starch can be a carrier for a flavor concentrate formulation. In some embodiments, the carrier is the same as the dilution medium used to reconstitute the flavor concentrate formulation; in other embodiments, the carrier is different from the dilution medium. As used herein, the term "carrier" includes, but is not limited to, an ingestibly acceptable carrier.

[0108] The term "adjuvant" means an additive that supplements, stabilizes, maintains, or enhances the intended function or efficacy of an active ingredient, such as a compound of the present application. In an embodiment, the at least one adjuvant comprises one or more flavoring agents. The flavoring agent can have any flavor known to one of skill in the art or to a consumer, such as a flavor of chocolate, coffee, tea, mocha, French vanilla, peanut butter, chai, or combinations thereof. In another embodiment, the at least one adjuvant comprises one or more sweetening agents. The one or more sweetening agents can be any sweetening agent described in the present application. In another embodiment, the at least one adjuvant comprises one or more ingredients selected from the group consisting of emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, salts, and combinations thereof. Examples of emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, and salts are described in U.S. Patent No. 6,468,576, the entire contents of which are incorporated by reference herein in their entirety for all purposes.

[0109] In some embodiments, the ingestible composition is encapsulated, such as in a cellulose-based or starch-based microcapsule.

[0110] Flavored products

[0111] In certain aspects, the present disclosure provides a flavored product comprising any of the ingestible compositions of the preceding aspects. In some embodiments, the flavored product is a beverage product, such as a soda, a flavored water, a tea, and the like. In some other embodiments, the flavored product is a food product, such as a dairy analog product or a meat analog product. In some other embodiments, the flavored product is an oral care product, such as a toothpaste, a mouthwash, a whitening formulation, and the like. In some other embodiments, the flavored product is a nutraceutical or a pharmaceutical product.

[0112] In embodiments where the flavored product is a beverage, the beverage can be selected from the group consisting of enhanced sparkling beverages, colas, lemon-lime flavored sparkling beverages, orange flavored sparkling beverages, grape flavored sparkling beverages, strawberry flavored sparkling beverages, pineapple flavored sparkling beverages, ginger-ales, root beers, fruit juices, fruit-flavored juices, juice drinks, nectars, vegetable juices, vegetable-flavored juices, sports drinks, energy drinks, fortified water drinks, vitamin-containing fortified waters, near water drinks, coconut waters, tea-based drinks, coffee, cocoa drinks, dairy ingredient-containing drinks, cereal extract-containing drinks, and smoothies. In some embodiments, the beverage can be a soft drink.

[0113] In certain embodiments of any of the aspects and embodiments set forth herein relating to a flavored product, the flavored product is a non-naturally occurring product, such as a packaged food or beverage product.

[0114] Other non-limiting examples of food and beverage products or formulations include sweet coatings, frostings or icings for such products, or any entity included in the following: soups, dry processed foods, beverages, ready-to-eat foods, canned or pickled foods, frozen processed foods, refrigerated processed foods, snack foods, baked goods, confections, dairy products, ice creams, meal replacements, pastas and noodles, and sauces, dressings, condiments, baby foods, and / or spreads.

[0115] In general, soups refer to canned / pickled, dehydrated, instant, refrigerated, UHT, and frozen soups. For purposes of this definition, soup refers to a food made from meat, poultry, fish, vegetables, grains, fruits, and other ingredients, cooked in a liquid, which can contain some or all of these ingredients in visible pieces. It can be clear (as a broth) or thick (as a chowder), smooth, pureed, or chunky, ready-to-serve, semi-concentrated, or concentrated, and cold or hot, as a first course or main course or as a between-meal snack (sipping beverage). Soups can be used as a base for making other dietary components, ranging from consommé to sauce (cream or cheese-based soups).

[0116] Dehydrated and cooked food categories generally refer to: (i) cooking aid products, such as: powdered, granular, pasty, concentrated liquid products, including concentrated bouillon, broth, and pressed blocks, tablets, or powdered or granular bouillon-like products, sold either as finished products or as ingredients in products, seasonings, and recipe mixes, regardless of technology; (ii) meal solution products, such as: dehydrated soups and freeze-dried soups, including dehydrated soup mixes, dehydrated instant soups, dehydrated ready-to-eat soups, dehydrated or self-heating preparations of ready meals, meals, and single-serve entrees, including pasta, potatoes, and rice; (iii) meal garnish products, such as: condiments, marinades, salad dressings, salad toppings, dips, breading, batter mixes, shelf-stable sauces, barbecue sauces, liquid recipe mixes, concentrates, sauce or gravy mixes, including salad recipe mixes, sold either as finished products or as ingredients in products, whether dehydrated, liquid, or frozen.

[0117] Beverage categories generally refer to beverages, beverage mixes, and concentrates, including but not limited to carbonated and non-carbonated beverages, alcoholic and non-alcoholic beverages, ready-to-drink beverages, liquid concentrate formulations for making beverages (e.g., soda), and dry powdered beverage precursor mixes. Beverage categories also include alcoholic beverages, soft drinks, sports drinks, isotonic drinks, and hot beverages. Alcoholic beverages include but are not limited to beer, cider / perry, FABs, wine, and spirits. Soft drinks include but are not limited to carbonated beverages, such as colas and non-cola carbonated beverages; fruit juices, such as juice drinks, nectars, juice beverages, and fruit-flavored beverages; bottled waters, including seltzer, spring, and purified / table waters; functional beverages, which can be carbonated or still, including sports drinks, energy drinks, or elixir drinks; and concentrates, such as liquid and powder concentrates that can be ready-to-drink. Hot beverages include but are not limited to coffee or iced coffee, such as fresh, instant, and blended coffee; tea or iced tea, such as black, green, white, oolong, and flavored tea; and other beverages, including flavored, malt-based, or plant-based powders, granules, blocks, or tablets that are mixed with milk or water.

[0118] Snack (savoury) categories generally refer to any food that is a simple, informal meal, including but not limited to sweet and savory snacks and snack bars. Examples of snacks include but are not limited to fruit snacks, potato chips / crisps, extruded snacks, tortilla / tortilla chips, popcorn, pretzels, nuts, and other sweet and savory snacks. Examples of snack bars include but are not limited to granola / muesli bars, breakfast bars, energy bars, fruit bars, and other snack bars.

[0119] Bakery items generally refer to any edible product that involves exposure to heat or excessive sunlight during the preparation process. Examples of bakery items include, but are not limited to, bread, buns, biscuits, muffins, cereals (granola), toaster pastries, cakes, waffles, tortillas, cookies, pies, bagels, quiches, custards, cakes, any bakery item, and any combination thereof.

[0120] Ice cream generally refers to a frozen confectionery that includes cream, sugar, and flavorings. Examples of ice cream include, but are not limited to, impulse ice cream; family-sized ice cream; frozen yogurt and artisanal ice cream; soy-, oat-, legume (e.g., red bean and green bean)- and rice-based ice cream.

[0121] Confectionery generally refers to a sweet-tasting edible product. Examples of confectionery include, but are not limited to, hard candies, gelatin, chocolate candies, fondants, chewing gum, and the like, as well as any combination product.

[0122] Meal replacement generally refers to any food product that is intended to replace a regular meal, particularly for those who are health or fitness conscious. Examples of meal replacements include, but are not limited to, weight loss products and recovery products.

[0123] Ready-to-eat food generally refers to any food product that can be consumed as a meal without extensive preparation or processing. Ready-to-eat foods include products for which the manufacturer has added recipe "skills" and thus have a high degree of ready-to-eat-ness, completeness, and convenience. Examples of ready-to-eat foods include, but are not limited to, canned / preserved, frozen, dried, refrigerated ready-to-eat foods; dinner mixes; frozen pizza; refrigerated pizza; and pre-made salads.

[0124] Pasta and noodle generally refers to any pasta and / or noodle, including, but not limited to, canned, dried, and refrigerated / fresh pasta; and plain, instant, refrigerated, frozen, and snack noodles.

[0125] Canned / preserved foods generally refer to, but are not limited to, canned / preserved meats and meat products, fish / seafood, vegetables, tomatoes, legumes, fruits, ready-to-eat foods, soups, pastas, and other canned / preserved foods.

[0126] Frozen processed foods generally refer to, but are not limited to, frozen processed red meats, processed poultry, processed fish / seafood, processed vegetables, meat substitutes, processed potatoes, baked products, desserts, ready-to-eat foods, pizza, soups, noodles, and other frozen foods.

[0127] Dry processed food classes include, but are not limited to, rice, dessert mixes, dry ready-to-eat foods, dehydrated soups, instant soups, dry pasta, plain noodles, and instant noodles. Chilled processed food classes include, but are not limited to, chilled processed meats, processed fish / seafood products, lunch kits, fresh-cut fruits, ready meals, pizza, prepared salads, soups, fresh pasta, and noodles.

[0128] Sauces, condiments, and relishes classes include, but are not limited to, ketchup and relish, bouillon / cubes, herbs and spices, monosodium glutamate (MSG), cocktail sauce, soy-based sauces, pasta sauce, wet / cooking sauces, dry sauce / powder mixes, tomato sauce, mayonnaise, mustard, salad dressing, vinaigrette, dips, marinades, and other sauces, condiments, and relishes.

[0129] Infant food classes include, but are not limited to, milk- or soy-based formula; and prepared, dry, and other infant foods.

[0130] Spread classes include, but are not limited to, jams and preserves, honey, chocolate spreads, nut-based spreads, and yeast-based spreads.

[0131] Dairy products classes generally refer to edible products produced from the milk of a mammal. Examples of dairy products include, but are not limited to, drinking milk products, cheese, yogurt, and sour milk drinks, and other dairy products.

[0132] Additional examples of flavored products, particularly food and beverage products or formulations, are provided as follows. Exemplary ingestible compositions include one or more of the following: confectionery, chocolate bar, chocolate tablet, countlines, selflines / softlines, boxed assortment, standard boxed assortment, twist wrapped miniatures, flavoured chocolate, chocolate with toys, biscuit bars, other chocolate confectionery, mints, standard mints, power mints, boiled sweets, pastilles, gum, jelly and chewing gum, toffee, caramel and nougat, pharmaceutical confectionery, lollipops, liquorice, other confectionery, bread, packaged / industrial bread, loose / handmade bread, cakes, cake, packaged / industrial cakes, loose / handmade cakes, biscuits, chocolate coated biscuits, sandwich biscuits, filled biscuits, savoury biscuits and crackers, bread substitutes, breakfast cereals, ready breakfast cereals, family breakfast cereals, cornflakes, muesli, other cereals, children's breakfast cereals, hot cereals, ice cream, ready ice cream, single portion dairy ice cream, single portion water ice cream, multi-pack dairy ice cream, multi-pack water ice cream, family ice cream, family dairy ice cream, ice cream desserts, bulk ice cream, family water ice cream, frozen yoghurt, artisan ice cream, dairy products, milk, fresh / pasteurised milk, full fat fresh / pasteurised milk, semi skimmed fresh / pasteurised milk, longer shelf life / ultra-heat treated milk, full fat longer shelf life / ultra-heat treated milk, semi skimmed longer shelf life / ultra-heat treated milk, fat free longer shelf life / ultra-heat treated milk, goat's milk, condensed / evaporated milk, plain condensed / evaporated milk, flavoured, functional and other condensed milk, flavoured milk drinks, dairy only flavoured milk drinks, flavoured milk drinks with fruit juice, soya milk, yoghurt drinks, fermented milk drinks, creamers for coffee, powdered milk, flavoured powdered milk drinks, creams, processed cheese, spreadable processed cheese, processed cheese not easily spreadable, unprocessed cheese, spreadable unprocessed cheese, hard cheese, packaged hard cheese, unpackaged hard cheese, yoghurt, plain / natural yoghurt, flavoured yoghurt, fruit yoghurt, probiotic yoghurt, drinking yoghurt, regular drinking yoghurt, probiotic drinking yoghurt, frozen and shelf stable snacks, dairy based snacks, soya based desserts, frozen snacks, fresh cheese and quark, plain fresh cheese and quark, flavoured fresh cheese and quark, savoury fresh cheese and quark, sweet and savoury snacks, fruit snacks, potato crisps / chips, extruded snacks, tortilla / tortilla chips, popcorn, pretzels, nuts, other sweet and savoury snacks, snack bars, granola bars, breakfast bars, energy bars, fruit bars, other snack bars, meal replacements, weight management products, recovery drinks, ready meals, canned ready meals, frozen ready meals, dried ready meals, frozen ready meals, dinner mixes, frozen pizza, chilled pizza, soups, canned soups, dehydrated soups, instant soups, chilled soups, hot soups, frozen soups, pasta, canned pasta, dried pasta,Frozen / fresh pasta, noodles, plain noodles, instant noodles, cup / bowl instant noodles, bagged instant noodles, frozen noodles, snack noodles, canned foods, canned meat and meat products, canned fish / seafood, canned vegetables, canned tomatoes, canned beans, canned fruit, canned ready-to-eat foods, canned soups, canned pasta, other canned foods, frozen foods, frozen processed red meat, frozen processed poultry, frozen processed fish / seafood, frozen processed vegetables, frozen meat substitutes, frozen potatoes, oven-baked potato chips, other oven-baked potato products, non-oven frozen potatoes, frozen baked foods, frozen desserts, frozen ready-to-eat foods, frozen pizzas, frozen soups, frozen noodles, other frozen foods, dried foods, dessert mixtures, dried ready-to-eat foods, dehydrated soups, instant soups, dried pasta, plain noodles, instant noodles, cup / bowl instant noodles, bagged instant noodles, refrigerated foods, refrigerated processed meats, refrigerated fish / seafood products, refrigerated processed fish, refrigerated coated fish Refrigerated smoked fish, refrigerated lunch packs, refrigerated ready-to-eat foods, refrigerated pizzas, refrigerated soups, refrigerated / fresh pasta, refrigerated noodles, oils and fats, olive oil, vegetable and seed oils, cooking fats, butter, margarine, spread oils and fats, functional spread oils and fats, sauces, seasonings and condiments, tomato paste and puree, broth / soup cubes, soup cubes, gravy granules, liquid soup bases and ingredients, herbs and spices, fermented sauces, soy sauces, pasta sauces, wet sauces, dry sauces / powder mixtures, tomato sauce, mayonnaise, regular mayonnaise, mustard, salad dressing, regular salad dressing, low-fat salad dressing, balsamic vinegar sauce, dips, marinades, other sauces, seasonings and condiments, baby food, formula milk powder, standard formula milk powder, growing-up formula milk powder, toddler formula milk powder, hypoallergenic formula, prepared baby food, dried baby food, other baby food, spreads, jams and preserves, honey, chocolate spread, nut spreads and yeast spreads. Exemplary ingestible compositions also include confectionery, baked goods, ice cream, dairy products, sweet and delicious snacks, snack bars, meal replacement products, ready-to-eat foods, soups, pasta, noodles, canned foods, frozen foods, dried foods, refrigerated foods, oils and fats, baby foods, or spreads, or mixtures thereof. Exemplary ingestible compositions also include breakfast cereals, sweetened beverages, or solid or liquid concentrate compositions for preparing beverages, ideally enabling the reduction of the concentration of previously known sugar sweeteners or artificial sweeteners.

[0133] Some embodiments provide chewable compositions that can be swallowed or not. In some embodiments, the chewable composition may be gum, chewing gum, saccharified gum, sugar-free gum, functional gum, bubble gum, which individually or in combination comprises compounds disclosed and described herein.

[0134] In one embodiment, the flavor concentrate formulation of the present application can be in a form selected from the group consisting of liquids, solids, foams, pastes, gels, emulsions, and combinations thereof, for example, a liquid containing an amount of solid content. In one embodiment, the flavor concentrate formulation is in a liquid form including water-based and non-water-based. In some embodiments, the flavor concentrate formulation of the present application can be carbonated or non-carbonated.

[0135] The flavored product can further comprise a freezing point depressant, a nucleating agent, or both as the at least one adjuvant. A freezing point depressant is an ingestionally acceptable compound or agent that can lower the freezing point of a liquid or solvent to which the compound or agent is added. That is, the freezing point of a liquid or solution containing a freezing point depressant is lower than the freezing point of a liquid or solvent without the freezing point depressant. In addition to lowering the initial freezing point, a freezing point depressant can also lower the water activity of the flavor concentrate formulation. Examples of freezing point depressants include, but are not limited to, carbohydrates, oils, ethanol, polyols such as glycerol, and combinations thereof. A nucleating agent refers to an ingestionally acceptable compound or agent that is capable of promoting nucleation. The presence of a nucleating agent in the flavor concentrate formulation can improve the mouthfeel of the slush and help maintain the physical properties and performance of the slush at freezing temperatures by increasing the number of ice crystal centers desired. Examples of nucleating agents include, but are not limited to, calcium silicate, calcium carbonate, titanium dioxide, and combinations thereof.

[0136] In one embodiment, the flavored product is formulated to have a low water activity to extend the shelf life. Water activity is the ratio of the vapor pressure of water in a formulation to the vapor pressure of pure water at the same temperature. In one embodiment, the water activity of the flavor concentrate formulation is less than about 0.85. In another embodiment, the water activity of the flavor concentrate formulation is less than about 0.80. In another embodiment, the water activity of the flavor concentrate formulation is less than about 0.75.

[0137] In some embodiments, the flavored product can be used in a number of different physical forms well known in the art to provide an initial burst of flavor and / or a prolonged flavor perception. Without limitation, these physical forms include free forms such as spray-dried, powdered, beaded, encapsulated, and combinations thereof.

[0138] In some embodiments, the flavored product comprises a bulking agent. 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, ribose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharides, cellulose and cellulose derivatives, and the like, and mixtures thereof. In addition, granulated sugar (sucrose) or other caloric sweetener (e.g., crystalline fructose, other carbohydrates, or sugar alcohols) can be used as a bulking agent as they provide good content uniformity without adding significant calories.

[0139] In an embodiment, the bulking agent can be a bulking agent described in U.S. Patent No. 8,993,027. In an embodiment, the bulking agent can be a bulking agent described in U.S. Patent No. 6,607,771. In an embodiment, the bulking agent can be a bulking agent described in U.S. Patent No. 6,932,982.

[0140] In some embodiments, the flavored product can further comprise at least one anticaking agent. As used herein, the phrases “anticaking agent” and “flow agent” mean any composition that prevents, reduces, inhibits, or suppresses the attachment, bonding, or contact of at least one sweetener to another sweetener molecule. Alternatively, an anticaking agent can mean any composition that aids in content uniformity and uniform dissolution. Non-limiting examples of anticaking agents include cream of tartar, calcium silicate, silicon dioxide, microcrystalline cellulose (Avicel, FMC BioPolymer, Philadelphia, PA), and tricalcium phosphate. In an embodiment, the anticaking agent is present in the tableted sweetener composition in an amount of from about 0.001% to about 3% by weight of the tableted sweetener composition.

[0141] Non-animal protein materials and products made therefrom

[0142] Products intended to replace or substitute for meat or dairy products often rely on various non-animal based materials, such as starches and proteins derived from plants, algae, fungi, or combinations thereof, to mimic the texture and flavor of meat or dairy products. Non-limiting examples of non-animal based proteins include plant proteins, such as soy protein, pea protein, bean protein, grain protein, and the like. Due to the compositional differences between such plant-derived materials and animal-derived materials, these proteins can impart a bitter taste.

[0143] Accordingly, in certain aspects, the present disclosure provides a flavored product comprising a plant-based material (e.g., a plant-based starch, a plant-based protein, or a combination thereof) and a piperonyl ether compound. In some embodiments, the flavored product comprises a piperonyl ether compound and a plant protein, such as a pea protein, a soy protein, a potato protein, a chickpea protein, a legume protein, or any combination thereof. In some further embodiments, the flavored product can comprise any feature or combination of features of the ingestible compositions described above that contain a piperonyl ether compound. In some embodiments, the flavored product is a beverage, such as a soy milk, an almond milk, a rice milk, an oat milk, a protein drink, a meal replacement drink, or other similar product. In some other embodiments, the flavored product is a meat substitute product, such as a plant-based chicken product (e.g., plant-based chicken nuggets), a plant-based beef product (e.g., a plant-based burger), and the like. In some other embodiments, the flavored product is a protein powder, a meal replacement powder, a plant-based creamer for coffee or tea, and the like. In certain additional embodiments, any such product comprises additional ingredients and has additional features, such as those typically used in the preparation and / or manufacture of such products. For example, such piperonyl ether compounds can be combined with other flavorants and taste modifiers, and can even be encapsulated in certain materials, in accordance with known techniques in the relevant art. Suitable concentrations of the piperonyl ether compounds are as described above.

[0144] In some embodiments, the flavored product comprises one or more plant proteins that impart a bitter taste to the product, which is at least partially reduced by the use of a piperonyl ether compound in the product. Such plant proteins include, but are not limited to, pea proteins, soy proteins, canola (rapeseed) proteins, potato proteins, chickpea proteins, mycoproteins, algal proteins, fava bean proteins, sunflower proteins, wheat proteins, and the like.

[0145] In some further embodiments similar to the above-described embodiments, algal or fungal proteins or starches are used instead, such as oat proteins, potato proteins, and the like. In some embodiments, these flavored products further comprise a fiber to provide a texture to the product. Suitable fibers for use include, but are not limited to, psyllium fiber, pea fiber, potato fiber, gellan gum, soluble corn fiber (glucan and / or maltodextrin), citrus fiber, and combinations thereof. In such products, the piperonyl ether compound can be introduced in any suitable manner. In some embodiments, the piperonyl ether compound is incorporated with other flavor imparting ingredients into a flavoring emulsion, such as a water-in-oil emulsion.

[0146] Blocking bitterness in pharmaceutical APIs and nutraceuticals

[0147] Many pharmaceutical compounds have a bitter taste, thus limiting their formulation and mode of administration. Accordingly, in certain aspects, the present disclosure provides a nutritional or pharmaceutical composition comprising a bitter-tasting nutritional or pharmaceutical active ingredient and a vanillyl ether compound. Such nutritional or pharmaceutical compositions can be in any form suitable for oral administration, such as tablets, lozenges, capsules, powders, liquid solutions, liquid suspensions, and the like. Such nutritional or pharmaceutical compositions can include any suitable excipients, binders, and the like, such as those set forth in Remington's Pharmaceutical Sciences. In some embodiments, the bitter-tasting pharmaceutical active ingredient is an ion channel inhibitor, such as a proton channel inhibitor. Other examples of bitter-tasting APIs whose bitterness can be reduced by a saturated fatty acid compound include, but are not limited to, acetaminophen, atropine, brinzolamide, chloramphenicol, chloroquine, clindamycin, dexamethasone, digoxin, diltiazem, diphenhydramine, docusate, doxazosin, doxepin, doxylamine, enalapril, erythromycin, esomeprazole, famotidine, gabapentin, ginkolide A, guaifenesin, L-histidine, lomefloxacin, methylprednisolone, ofloxacin, oleuropein, oxyphenonium, perenzepine, prednisone, ranitidine, trapidil, trimethoprim, and cetirizine.

[0148] Use in oral care products

[0149] Oral care products often contain ingredients that impart astringency or bitterness. These ingredients include menthol, menthol analogs, peppermint extract, sodium bicarbonate, oxides of alkali metal (oxides of potassium), cetylpyridinium chloride, lauryl amidopropyl betaine, cocamidopropyl betaine, arginine, hydrogen peroxide, chlorhexidine gluconate, zinc phosphate, zinc chloride, zinc citrate, potassium nitrate, pentasodium triphosphate, tetrasodium pyrophosphate, stannous fluoride, thymol, methyl salicylate, eucalyptol, or any combination thereof. Suitable oral care products include toothpastes, mouthwashes, whitening agents, dentifrices, and the like. In certain aspects, the present disclosure provides an oral care product comprising a vanillyl ether compound described herein.

[0150] Examples

[0151] To further illustrate the application, the following examples are included. Of course, these examples should not be construed as specifically limiting the application. Variations of these examples that are within the purview of persons skilled in the art are deemed to fall within the scope of the present application as described and claimed herein. The reader will recognize that skilled artisans and experts in the art can prepare and use the present application without undue experimentation, absent the exhaustive examples.

[0152] Example 1 - Pea protein with vanillyl ether

[0153] A liquid pea protein concentrate composition (3 wt% in water) was prepared without added sugar. Control and test samples were prepared. To two test samples, vanillyl ethyl ether (VEE) and vanillyl butyl ether (VBE) were added at a concentration of 0.5 ppm, respectively. Sensory panelists evaluated the control and test samples and scored the bitterness and astringency of the control and two test samples on a scale of 0 to 10. Table 2 reports the average difference between the bitterness and astringency scores of the control and two test samples.

[0154] Table 2

[0155] Bitterness ]]> ​ Astringency ]]> ​ VEE sample -0.5 -1.5 VBE sample -1.0 -2.2

[0156] Thus, the introduction of vanillyl ether compounds into a pea protein solution can moderately reduce bitterness and significantly reduce astringency.

[0157] Example 2 - Lemon tea beverage with vanillyl ether

[0158] A lemon tea beverage sample was prepared. Table 3 lists the ingredients of the lemon tea base, which was used as a control sample.

[0159] Table 3

[0160] Ingredients ]]> ​ Weight percent ]]> ​ Sodium benzoate 0.014 Potassium sorbate 0.012 Black tea solids 0.100 Citric acid 0.120 Ascorbic acid 0.010 Trisodium citrate 0.020 Stevia sweetener (50% rebaudioside A) 0.046 Orange flavoring 0.050 Lemon flavoring 0.145 Water Balance

[0161] Two test samples were prepared by adding (a) vanillyl ethyl ether (VEE) at a concentration of 0.5 ppm and (b) vanillyl ethyl ether (VEE) at a concentration of 0.5 ppm and phloretin at a concentration of 8 ppm, respectively. Sensory panelists evaluated the control and test samples and scored the various attributes of the control and two test samples on a scale of 0 to 10. Higher scores indicate a stronger intensity of the attribute in the sample. Table 4 shows the average results of the control and two test samples.

[0162] Table 4

[0163] Control ]]> ​ VEE ]]> ​ VEE + phloretin ]]> ​ Unfront sweetness 4.5 4.7 4.9 Peak sweetness 5.4 5.4 5.3 Prolonged sweetness 4.9 4.0 4.2 Lemon flavor 4.6 4.8 5.0 Bitterness 3.8 2.7 2.4 Astringency 3.0 2.1 2.3 Mouthfeel 3.1 3.5 3.7 Off flavor intensity 2.9 2.4 2.5

Claims

1. Use of a vanillyl ether compound for modifying the flavor of an ingestible composition, wherein the vanillyl ether compound is a compound of Formula (I) or an edible acceptable salt thereof: wherein: R1is H, CH3, or CH2CH3; R2is H, CH3, or CH2CH3; R3is H, CH3, or CH2CH3; R4is H, CH3, or CH2CH3; R5is H, CH3, or CH2CH3; R6is H, CH3, or CH2CH3; R7is H, CH3, or CH2CH3; R8is H, CH3, or CH2CH3; R9is H, CH3, or CH2CH3; R10is H, CH3, or CH2CH3; R11is H, CH3, or CH2CH3; R12is H, CH3, or CH2CH3; R13is H, CH3, or CH2CH3; R14is H, CH3, or CH2CH3; R15is H, CH3, or CH2CH3; R16is H, CH3, or CH2CH3; R17is H, CH3, or CH2CH3; R18is H, CH3, or CH2CH3; R19is H, CH3, or CH2CH3; R20is H, CH3, or CH2CH3; R21is H, CH3, or CH2CH3; R22is H, CH3, or CH2CH3; R23is H, CH3, or CH2CH3; R24is H, CH3, or CH2CH3; R25is H, CH3, or CH2CH3; R26is H, CH3, or CH2CH3; R27is H, CH3, or CH2CH3; R28is H, CH3, or CH2CH3; R29is H, CH3, or CH2CH3; R30is H, CH3, or CH2CH3; R31is H, CH3, or CH2CH3; R32is H, CH3, or CH2CH3; R33is H, CH3, or CH2CH3; R34is H, CH3, or CH2CH3; R35is H, CH3, or CH2CH3; R36is H, CH3, or CH2CH3; R37is H, CH3, or CH2CH3; R38is H, CH3, or CH2CH3; R39is H, CH3, or CH2CH3; R40is H, CH3, or CH2CH3; R41is H, CH3, or CH2CH3; R42is H, CH3, or CH2CH3; R43is H, CH3, or CH2CH3; R44is H, CH3, or CH2CH3; R45is H, CH3, or CH2CH3; R46is H, CH3, or CH2CH3; R47is H, CH3, or CH2CH3; R48is H, CH3, or CH2CH3; R49is H, CH3, or CH2CH3; R50is H, CH3, or CH2CH3; R51is H, CH3, or CH2CH3; R52is H, CH3, or CH2CH3; R53is H, CH3, or CH2CH3; R54is H, CH3, or CH2CH3; R55is H, CH3, or CH2CH3; R56is H, CH3, or CH2CH3; R57is H, CH3, or CH2CH3; R58is H, CH3, or CH2CH3; R59is H, CH3, or CH2CH3; R60is H, CH3, or CH2CH3; R61is H, CH3, or CH2CH3; R62is H, CH3, or CH2CH3; R63is H, CH3, or CH2CH3; R64is H, CH3, or CH2CH3; R65is H, CH3, or CH2CH3; R66is H, CH3, or CH2CH3; R67is H, CH3, or CH2CH3; R68is H, CH3, or CH2CH3; R69is H, CH3, or CH2CH3; R70is H, CH3, or CH2CH3; R71is H, CH3, or CH2CH3; R72is H, CH3, or CH2CH3; R73is H, CH3, or CH2CH3; R74is H, CH3, or CH2CH3; R75is H, CH3, or CH2CH3; R76is H, CH3, or CH2CH3; R77is H, CH3, or CH2CH3; R78is H, CH3, or CH2CH3; R79is H, CH3, or CH2CH3; R80is H, CH3, or CH2CH3; R81is H, CH3, or CH2CH3; R82is H, CH3, or CH2CH3; R83is H, CH3, or CH2CH3; R84is H, CH3, or CH2CH3; R85is H, CH3, or CH2CH3; R86is H, CH3, or CH2CH3; R87is H, CH3, or CH2CH3; R88is H, CH3, or CH2CH3; R89is H, CH3, or CH2CH3; R90is H, CH3, or CH2CH3; R91is H, CH3, or CH2CH3; R92is H, CH3, or CH2CH3; R93is H, CH3, or CH2CH3; R94is H, CH3, or CH2CH3; R95is H, CH3, or CH2CH3; R96is H, CH3, or CH2CH3; R97is H, CH3, or CH2CH3; R98is H, CH3, or CH2CH3; R99is H, CH3, or CH2CH3; R100is H, CH3, or CH2CH3; R101is H, CH3, or CH2CH3; R102is H, CH3, or CH2CH3; R103is H, CH3, or CH2CH3; R104is H, CH3, or CH2CH3; R105is H, CH3, or CH2CH3; R106is H, CH3, or CH2CH3; R107is H, CH3, or CH2CH3; R108is H, CH3, or CH2CH3; R109is H, CH3, or CH2CH3; R110is H, CH3, or CH2CH3; R111is H, CH3, or CH2CH3; R112is H, CH3, or CH2CH3; R113is H, CH3, or CH2CH3; R114is H, CH3, or CH2CH3; R115is H, CH3, or CH2CH3; R116is H, CH3, or CH2CH3; R117is H, CH3, or CH2CH3; R118is H, CH3, or CH2CH3; R119is H, CH3, or CH2CH3; R120is H, CH3, or CH2CH3; R121is H, CH3, or CH2CH3; R122is H, CH3, or CH2CH3; R123is H, CH3, or CH2CH3; R124is H, CH3, or CH2CH3; R125is H, CH3, or CH2CH3; R126is H, CH3, or CH2CH3; R127is H, CH3, or CH2CH3; R128is H, CH3, or CH2CH3; R129is H, CH3, or CH2CH3; R130is H, CH3, or CH2CH3; R131is H, CH3, or CH2CH3; R132is H, CH3, or CH2CH3; R133is H, CH3, or CH2CH3; R134is H, CH3, or CH2CH3; R135is H, CH3, or CH2CH3; R136is H, CH3, or CH2CH3; R137is H, CH3, or CH2CH3; R138is H, CH3, or CH2CH3; R139is H, CH3, or CH2CH3; R140is H, CH3, or CH2CH3; R141is H, CH3, or CH2CH3; R142is H, CH3, or CH2CH3; R143is H, CH3, or CH2CH3; R144 ​ R 1 R is hydrogen, methyl or ethyl; and R 2 is a hydrogen atom, C 1-8 alkyl, or C 3-8 cycloalkyl, or -CH2-(phenyl), wherein the phenyl moiety is optionally substituted one to two times with substituents independently selected from the group consisting of -OH and -OCH3.

2. Use according to claim 1, wherein R 1 is methyl and R 2 is C 1-8 alkyl. ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ R 1 is methyl or ethyl; and R 2 is a hydrogen atom, C 1-8 alkyl, or C 3-8 cycloalkyl, or -CH2-(phenyl), wherein the phenyl moiety is optionally substituted one to two times with substituents independently selected from the group consisting of -OH and -OCH3. ​ ​ R 1 is methyl or ethyl; and R 2 is a hydrogen atom, C 1-8 alkyl, or C 3-8 cycloalkyl, or -CH2-(phenyl), wherein the phenyl moiety is optionally substituted one to two times with substituents independently selected from the group consisting of -OH and -OCH3. ​ ​ ​

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