Fatty acid amides and their use as flavour modifiers - Patents.com

Abstract

The present disclosure generally relates to certain fatty acid amide compounds, such as hydroxy-α-sanshool, hydroxy-β-sanshool, and hydroxy-γ-sanshool, and the use of such compounds to impart or enhance sweetness, and to mask bitterness, enhance texture, or mask astringency.In certain embodiments, such compounds are used in combination with other sweeteners or sweetness enhancers, such as flavonoids or dihydrochalcones.In certain aspects, the present disclosure provides ingestible compositions that include such fatty acid amides.In some related aspects, the ingestible compositions are or are included in various flavored products, such as food, beverage products, pharmaceutical products, or oral care products.

Description

[Technical field]

[0001] The present disclosure generally relates to certain fatty acid amide compounds, such as hydroxy-α-sanshool, hydroxy-β-sanshool, and hydroxy-γ-sanshool, and the use of such compounds to impart or enhance sweetness, and to mask bitterness, enhance texture, or mask astringency.In certain embodiments, such compounds are used in combination with other sweeteners or sweetness enhancers, such as flavonoids or dihydrochalcones.In certain aspects, the present disclosure provides ingestible compositions that include such fatty acid amides.In some related aspects, the ingestible compositions are or are included in various flavored products, such as food, beverage products, pharmaceutical products, or oral care products. [Background technology]

[0002] The taste system provides sensory information about the chemical composition of the external world. Gustatory transduction is one of the more sophisticated forms of chemically triggered sensation in animals. Taste signaling is found throughout the animal kingdom, from the simplest metazoans to the most complex of vertebrates. Mammals are thought to have five basic taste modalities: sweet, bitter, sour, salty, and umami.

[0003] Sweetness is the most commonly perceived taste when eating foods rich in sugars. Mammals generally perceive sweetness as a pleasant sensation, provided it is not excessive. Caloric sweeteners such as sucrose and fructose are the prototypical examples of sweet tastants. Although a variety of non-caloric and low-caloric alternatives exist, these caloric sweeteners remain the primary means by which edible products induce the perception of sweetness upon consumption.

[0004] Metabolic disorders and associated conditions, such as obesity, diabetes, and cardiovascular disease, are major public health concerns worldwide. And their prevalence is increasing at an alarming rate in nearly all developed countries. Caloric sweeteners are an important factor contributing to this trend, as they are included in various packaged food and beverage products to make them more palatable to consumers. In many cases, non-caloric or low-caloric substitutes can be used in place of sucrose or fructose in foods and beverages. Yet, these compounds impart a sweetness that is different from that of caloric sweeteners, and many consumers fail to see them as suitable substitutes. Moreover, such compounds can be difficult to incorporate into certain products. In some cases, they can be used as partial replacements for caloric sweeteners, but their presence alone can cause many consumers to perceive unpleasant off-tastes, including astringency, bitterness, and metallic and licorice tastes. Thus, low-calorie sweeteners face certain challenges to their adoption.

[0005] Sweetness enhancement provides an alternative approach to overcome some of the adoption challenges faced by low-calorie sweeteners. Such compounds can be used in combination with sucrose or fructose to enhance sweetness, thereby allowing the use of such calorie sweeteners in smaller amounts in various food or beverage products. However, such compounds still change the perceived taste of sweeteners in addition to enhancing the perceived sweetness of primary sweeteners. Thus, many consumers find that consuming such sweetness-enhancing products is less enjoyable compared to more calorie-rich non-enhanced alternatives. Therefore, there is a continuing need to discover compounds that enhance the sweetness of calorie sweeteners but do not change the perceived taste to the detriment of the enjoyment consumers experience when eating and drinking products that contain such sweeteners.

[0006] Summary of the Invention The present disclosure relates to the discovery that certain fatty acid amides can impart or enhance sweetness with a more natural taste, and in some cases can also be used to mask bitterness, improve texture, or mask astringency.

[0007] In a first aspect, the present disclosure provides a compound of formula (I): [ka] or a salt thereof, R 1 is -CH2-CH(CH3)2, -CH2-C(OH)(CH3)2, -CH2-C(=CH2)-CH3, -CH=C(CH3)2, or -CH2-C(OH)(CH2OH)(CH3); R 2 C9 alkyl, C 11 Alkyl, C9 alkenyl, or C 11 alkenyl, each of which is optionally substituted one or more times with hydroxy groups, oxo groups, or combinations thereof; Flavor-modifying compounds are provided.

[0008] In a second aspect, the present disclosure provides a flavor-modifying composition comprising one or more flavor-modifying compounds of the first aspect.In some embodiments, the flavor-modifying composition is a composition obtained from Zanthoxylum moniliforme oil.In some embodiments, the flavor-modifying composition is a composition obtained from the extraction of Zanthoxylum moniliforme oil using an aqueous or water-miscible solvent system.

[0009] In a third aspect, the present disclosure provides the use of a flavor modifying compound of the first aspect or a flavor modifying composition of the second aspect for enhancing the sweetness of an ingestible composition. In certain related aspects, the present disclosure provides a method for enhancing the sweetness of an ingestible composition, the method comprising introducing a flavor modifying compound of the first aspect or a flavor modifying composition of the second aspect into the ingestible composition. In some embodiments, the ingestible composition comprises one or more sweeteners, such as caloric or non-caloric sweeteners. In some embodiments, the ingestible composition comprises one or more flavonoids or dihydrochalcones.

[0010] In a fourth aspect, the present disclosure provides the use of a flavor modifying compound of the first aspect or a flavor modifying composition of the second aspect to reduce the bitterness of an ingestible composition. In certain related aspects, the present disclosure provides a method of reducing the bitterness of an ingestible composition, the method comprising introducing a flavor modifying compound of the first aspect or a flavor modifying composition of the second aspect into the ingestible composition. In some embodiments, the ingestible composition comprises one or more bitter tastants, such as certain high-intensity sweeteners, caffeine, tannins, pharmaceutical APIs, etc. In some embodiments, the ingestible composition comprises one or more flavonoids or dihydrochalcones.

[0011] In a fifth aspect, the present disclosure provides a use of the flavor modifying compound of the first aspect or the flavor modifying composition of the second aspect for reducing the astringency of an ingestible composition. In certain related aspects, the present disclosure provides a method for reducing the astringency of an ingestible composition, comprising introducing the flavor modifying compound of the first aspect or the flavor modifying composition of the second aspect into the ingestible composition. In some embodiments, the ingestible composition comprises one or more astringent compounds. Non-limiting examples of such uses and methods include reducing the lingering liquorice aftertaste of certain high-intensity sweeteners, such as stevia-based high-intensity sweeteners. In some embodiments, the ingestible composition comprises one or more flavonoids or dihydrochalcones.

[0012] In a sixth aspect, the present disclosure provides the use of a flavor modifying compound of the first aspect or a flavor modifying composition of the second aspect to enhance the texture of an ingestible composition. In certain related aspects, the present disclosure provides a method of enhancing the texture of an ingestible composition, the method comprising introducing a flavor modifying compound of the first aspect or a flavor modifying composition of the second aspect into the ingestible composition. In some embodiments, the ingestible composition comprises one or more flavonoids or dihydrochalcones.

[0013] In a seventh aspect, the present disclosure provides an ingestible composition comprising one or more of the flavor modifying compounds of the first aspect or the flavor modifying composition of the second aspect. In some embodiments, the ingestible composition comprises one or more sweeteners. In some embodiments, the ingestible composition comprises one or more sweetness enhancers, such as flavonoids or dihydrochalcones. In some embodiments, the ingestible composition comprises one or more bitter tastants.

[0014] In an eighth aspect, the present disclosure provides a flavored product comprising the ingestible composition of the seventh aspect. In some embodiments, the flavored product is a food or beverage product. In some embodiments, the flavored product is an oral care product or a pharmaceutical product.

[0015] Further aspects and embodiments thereof are described below in the detailed description, drawings, abstract, and claims.

[0016] The following drawings are provided for the purpose of illustrating various embodiments of the compositions and methods disclosed herein. The drawings are provided for illustrative purposes only and are not intended to illustrate any preferred compositions or preferred methods or to cause any limitation on the scope of the claimed invention. [Brief description of the drawings]

[0017] [Figure 1]1 is a chemical formula showing a flavor modifying compound disclosed herein, wherein R1 is -CH2-CH(CH3)2, -CH2-C(OH)(CH3)2, -CH2-C(=CH2)-CH3, -CH=C(CH3)2, or -CH2-C(OH)(CH2OH)(CH3), and R2 is a C9 alkyl, a C11 alkyl, a C9 alkenyl, or a C11 alkenyl, each of which is optionally substituted one or more times with a hydroxy group, an oxo group, or combinations thereof. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0018] The following detailed description describes various aspects and embodiments provided herein. The description should be read from the perspective of one of ordinary skill in the art. As such, it does not necessarily include information that is known to such a person of ordinary skill in the art.

[0019] definition The following terms and phrases have the meanings set forth below unless otherwise specified herein. This disclosure may use other terms and phrases that are not expressly defined herein. Such other terms and phrases have the meanings that they would have within the context of this disclosure to a person skilled in the art. In some cases, a term or phrase may be defined in the singular or plural. In such cases, it is understood that any term in the singular can include its plural counterpart, and vice versa, unless expressly indicated to the contrary.

[0020] "Sweetener" refers to a compound or an ingestibly acceptable salt thereof that induces a detectable sweet taste in a subject, e.g., a compound that activates the T1R2 and T1R3 taste receptors in vivo or in vitro.

[0021] "Bitter tastant" refers to a compound or an ingestibly acceptable salt thereof that induces a detectable bitter taste in a subject, e.g., a compound that activates one or more T2R taste receptors in vivo or in vitro.

[0022] As used herein, "C a ~C b " or "C a-b " (where "a" and "b" are integers) refers to the number of carbon atoms in a particular group. That is, the group may contain at least "a" and at most "b" carbon atoms. Thus, for example, "C1-C4 alkyl" or "C 1-4 An "alkyl" group refers to all alkyl groups having 1 to 4 carbons, i.e., CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, CH3CH2CH2CH2-, CH3CH2CH(CH3)-, and (CH3)3C-.

[0023] As used herein, "alkyl" refers to a straight or branched hydrocarbon chain that is fully saturated (i.e., contains no double or triple bonds). In some embodiments, the alkyl group has 1-20 carbon atoms (wherever it appears herein, a numerical range such as "1-20" refers to each integer within the given range. For example, "1-20 carbon atoms" means that the alkyl group may consist of 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc., up to 20 carbon atoms, although this definition also encompasses the occurrence of the term "alkyl" where no numerical range is specified). The alkyl group may also be a medium sized alkyl having 1-9 carbon atoms. The alkyl group may also be a lower alkyl having 1-4 carbon atoms. The alkyl group may also be a "C 1-4 By way of example only, "C 1-4 "Alkyl" indicates that the alkyl chain has 1 to 4 carbon atoms, i.e., the alkyl chain is selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and t-butyl. Typical alkyl groups include, but are in no way limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, pentyl, hexyl, and the like. Unless indicated to the contrary, the term "alkyl" refers to a group that is not further substituted.

[0024] As used herein, "alkenyl" refers to a straight or branched hydrocarbon chain containing one or more double bonds. In some embodiments, alkenyl groups have 2-20 carbon atoms, although this definition also encompasses the occurrence of the term "alkenyl" where no numerical range is specified. Alkenyl groups can also be medium size alkenyls having 2-9 carbon atoms. Alkenyl groups can also be lower alkenyls having 2-4 carbon atoms. An alkenyl group can be any of the groups "C 2-4 Alkenyl" or similar designations. 2-4 "Alkenyl" indicates that there are 2 to 4 carbon atoms in the alkenyl chain, i.e., the alkenyl chain is selected from the group consisting of ethenyl, propen-1-yl, propen-2-yl, propen-3-yl, buten-1-yl, buten-2-yl, buten-3-yl, buten-4-yl, 1-methyl-propen-1-yl, 2-methyl-propen-1-yl, 1-ethyl-ethen-1-yl, 2-methyl-propen-3-yl, buta-1,3-dienyl, buta-1,2,-dienyl, and buta-1,2-dien-4-yl. Exemplary alkenyl groups include, but are in no way limited to, ethenyl, propenyl, butenyl, pentenyl, and hexenyl. Unless indicated to the contrary, the term "alkenyl" refers to a group that is not further substituted.

[0025] As used herein, "hydroxy" or "hydroxyl" refers to an --OH substituent.

[0026] As used herein, "oxo" refers to a =O substituent.

[0027] 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" includes a single substituent as well as two or more substituents, and the like.

[0028] As used herein, "for example," "for instance," "such as," or "including" is meant to introduce examples that make the general subject matter more clear. Unless expressly stated otherwise, such examples are provided only as an aid to understanding the embodiments described in the present disclosure and are not meant to be limiting in any way. These phrases do not imply any kind of preference for the disclosed embodiments.

[0029] As used herein, "comprise" or "comprises" or "comprising" or "comprised of" refers to an open group, meaning that the group can include additional members in addition to those explicitly listed. For example, the phrase "comprising A" means that A must be present, but other members may be present. The terms "include," "have," and "composed of," and their grammatical variations, have the same meaning. In contrast, "consist of" or "consists of" or "consisting of" refers to a closed group. For example, the phrase "consisting of A" means that A is present and only A is present.

[0030] As used herein, "optionally" means that the subsequently described event may or may not occur. In some embodiments, the optional event does not occur. In some other embodiments, the optional event occurs one or more times.

[0031] As used herein, "or" should be given its broadest reasonable interpretation and should not be limited to an either / or configuration. Thus, the phrase "comprising A or B" means that A is present and B is absent, or B is present and A is absent, or both A and B are present. Furthermore, if, for example, A defines a class that can have multiple members, e.g., A1 and A2, one or more members of the class can be present at the same time.

[0032] Chemical structures are often shown using a "skeletal" format, such that the carbon atoms are not explicitly shown and the hydrogen atoms attached to carbon atoms are omitted entirely. For example, the structure [ka] represents butane (i.e., n-butane). Additionally, aromatic groups such as benzene are represented by showing one of the resonance contributing structures. For example, the structure [ka] represents toluene.

[0033] As used herein, the term "flavor modifying compound" or "fatty acid amide" or "fatty acid amide compound" or "sanshool compound" refers to any compound of formula (I) or any salt thereof and any embodiment thereof described herein.The term "flavor modifying composition" refers to a composition that comprises one or more such flavor modifying compounds, for example, the composition obtained from the extraction of Zanthoxylum moniliforme oil with aqueous or water-miscible solvent system.

[0034] Other terms not included in this subsection are defined elsewhere in this description.

[0035] Flavour modifying compounds and flavour modifying compositions In certain aspects, the present disclosure provides a compound of formula (I): [ka] or a salt thereof, R 1 is -CH2-CH(CH3)2, -CH2-C(OH)(CH3)2, -CH2-C(=CH2)-CH3, -CH=C(CH3)2, or -CH2-C(OH)(CH2OH)(CH3); R 2 C9 alkyl, C 11 Alkyl, C9 alkenyl, or C 11 alkenyl, each of which is optionally substituted one or more times with hydroxy groups, oxo groups, or combinations thereof; Flavor-modifying compounds are provided.

[0036] Variable R 1 can have any suitable value, in accordance with the above definition. In some embodiments, R 1 is -CH-CH(CH). In some embodiments, R 1 is -CH-C(OH)(CH). In some embodiments, R 1 is -CH2-C(=CH2)-CH3. In some embodiments, R 1 is -CH=C(CH). In some embodiments, R 1 is -CH-C(OH)(CHOH)(CH), where the β carbon atom is in either the R or S stereochemical configuration. In some such embodiments, the β carbon atom is in the R stereochemical configuration. In some other such embodiments, the β carbon atom is in the S stereochemical configuration.

[0037] Variable R 2 can have any suitable value, in accordance with the definition above. In some embodiments of any of the foregoing embodiments, R 2 is a C alkyl optionally substituted one or more times with a hydroxy group, an oxo group, or a combination thereof. In some embodiments, R 2is a straight chain C alkyl (nonyl) optionally substituted once or twice with a hydroxy group, an oxo group, or a combination thereof. In some embodiments, R 2 is nonyl.

[0038] In some embodiments of any of the foregoing embodiments, R 2 is optionally substituted once or twice with a hydroxy group, an oxo group, or a combination thereof; 11 In some embodiments, R 2 is a linear C optionally substituted one or more times with a hydroxy group, an oxo group, or a combination thereof; 11 In some embodiments, R 2 is undecyl.

[0039] In some embodiments of any of the foregoing embodiments, R 2 is a C alkenyl optionally substituted one or more times with a hydroxy group, an oxo group, or a combination thereof. In some embodiments, R 2 is a straight chain C alkenyl optionally substituted once or twice with a hydroxy group, an oxo group, or a combination thereof. In some embodiments, R 2 is an unsubstituted straight chain C alkenyl having 1 to 4 carbon-carbon double bonds. In some embodiments, R 2 is a straight chain C9 alkenyl having 1 to 4 carbon-carbon double bonds substituted once or twice with a substituent selected from the group consisting of hydroxy, oxo, or combinations thereof.

[0040] In some embodiments of any of the foregoing embodiments, R 2 is optionally substituted one or more times with a hydroxy group, an oxo group, or a combination thereof; 11 In some embodiments, R is alkenyl. 2is a linear C optionally substituted once or twice with a hydroxy group, an oxo group, or a combination thereof; 11 In some embodiments, R is alkenyl. 2 is an unsubstituted linear C 11 In some embodiments, R 2 is a straight-chain C having 1 to 4 carbon-carbon double bonds substituted once or twice with a substituent selected from the group consisting of hydroxy, oxo, or a combination thereof; 11 It is alkenyl.

[0041] Table 1 provides examples of flavor altering compounds of the present disclosure. In some embodiments, the flavor altering compound is compound 1 or a edible salt thereof. In some embodiments, the flavor altering compound is compound 2 or a edible salt thereof. In some embodiments, the flavor altering compound is compound 3 or a edible salt thereof. In some embodiments, the flavor altering compound is compound 4 or a edible salt thereof. In some embodiments, the flavor altering compound is compound 5 or a edible salt thereof. In some embodiments, the flavor altering compound is compound 6 or a edible salt thereof. In some embodiments, the flavor altering compound is compound 7 or a edible salt thereof. In some embodiments, the flavor altering compound is compound 8 or a edible salt thereof. In some embodiments, the flavor altering compound is compound 9 or a edible salt thereof. In some embodiments, the flavor altering compound is compound 10 or a edible salt thereof. In some embodiments, the flavor altering compound is compound 11 or a edible salt thereof. In some embodiments, the flavor altering compound is compound 12 or a edible salt thereof. In some embodiments, the flavor modifying compound is compound 13 or a edible acceptable salt thereof. In some embodiments, the flavor modifying compound is compound 14 or a edible acceptable salt thereof. In some embodiments, the flavor modifying compound is compound 15 or a edible acceptable salt thereof. In some embodiments, the flavor modifying compound is compound 16 or a edible acceptable salt thereof. In some embodiments, the amide compound is compound 17 or a edible acceptable salt thereof. In some embodiments, the amide compound is compound 18 or a edible acceptable salt thereof. In some embodiments, the amide compound is compound 19 or a edible acceptable salt thereof. In some embodiments, the amide compound is compound 20 or a edible acceptable salt thereof. In some embodiments, the amide compound is compound 21 or a edible acceptable salt thereof.In some embodiments, the amide compound is Compound 22 or a edible salt thereof. In some embodiments, the amide compound is Compound 23 or a edible salt thereof. In some embodiments, the amide compound is Compound 24 or a edible salt thereof. In some embodiments, the amide compound is Compound 25 or a edible salt thereof. In some embodiments, the amide compound is Compound 26 or a edible salt thereof. In some embodiments, the amide compound is Compound 27 or a edible salt thereof. In some embodiments, the amide compound is Compound 28 or a edible salt thereof. In some embodiments, the amide compound is Compound 29 or a edible salt thereof. In some embodiments, the amide compound is Compound 30 or a edible salt thereof. In some embodiments, the amide compound is Compound 31 or a edible salt thereof. In some embodiments, the amide compound is Compound 32 or a edible salt thereof. In some embodiments, the amide compound is Compound 33 or a edible salt thereof. In some embodiments, the amide compound is compound 34 or a edible salt thereof. In some embodiments, the amide compound is compound 35 or a edible salt thereof. In some embodiments, the amide compound is compound 36 or a edible salt thereof. In some embodiments, the amide compound is compound 37 or a edible salt thereof. In some embodiments, the amide compound is compound 38 or a edible salt thereof. In some embodiments, the amide compound is compound 39 or a edible salt thereof. In some embodiments, the amide compound is compound 40 or a edible salt thereof. In some embodiments, the amide compound is compound 41 or a edible salt thereof.

[0042] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6]

[0043] When the flavor modifying compounds disclosed herein have at least one chiral center, they can exist as individual enantiomers and diastereomers, or as mixtures of such isomers. In some embodiments related to the second aspect, the sweetening enhancing compounds have comparable enantiomeric purity.

[0044] Separation of individual isomers or selective synthesis of individual isomers can be achieved by applying various methods well known to those skilled in the art. Unless otherwise indicated (e.g., when the stereochemistry of a chiral center is explicitly indicated), all such isomers and mixtures thereof are included within the scope of the compounds disclosed herein. Furthermore, the compounds disclosed herein may exist in one or more crystalline or amorphous forms. Unless otherwise indicated, all such forms are included within the scope of the compounds disclosed herein, including any polymorphs. Furthermore, some of the compounds disclosed herein may form solvates with water (i.e., hydrates) or common organic solvents. Unless otherwise indicated, such solvates are included within the scope of the compounds disclosed herein.

[0045] Those skilled in the art will recognize that some structures described herein may be resonance forms or tautomers of compounds that may be significantly represented, even kinetically, by other chemical structures. Those skilled in the art will recognize that such structures may only represent a small portion of a sample of such compounds. Although such resonance forms or tautomers are not represented herein, such compounds are considered to be within the scope of the structures shown.

[0046] Isotopes may be present in the compounds described. Each chemical element represented in a compound structure may include any isotope of said element. For example, in a compound structure, a hydrogen atom may be explicitly disclosed or understood to be present in the compound. At any position of the compound where a hydrogen atom may be present, the hydrogen atom may be any isotope of hydrogen, including but not limited to hydrogen-1 (protium) and hydrogen-2 (deuterium). Thus, reference to a compound herein encompasses all possible isotopic forms, unless the context clearly indicates otherwise.

[0047] In some embodiments, the flavor-modifying compounds disclosed herein can form acid salts and / or base salts due to the presence of phenolic, amino and / or carboxyl groups or groups similar thereto. Food-acceptable acid addition salts can be formed with inorganic 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. Food-acceptable salts can be formed with inorganic and organic bases. Inorganic bases from which salts can be derived include, for example, bases containing sodium, potassium, lithium, ammonium, calcium, magnesium, iron, zinc, copper, manganese, aluminum, and the like, with ammonium, potassium, sodium, calcium, and magnesium salts being particularly preferred. In some embodiments, treatment of the compounds disclosed herein with an inorganic base results in the loss of a labile hydrogen from the compound, forming Li + , Na + , K + , Mg 2+ and Ca 2+ Salt forms containing inorganic cations such as are obtained. Organic bases from which salts can be derived include, for example, primary, secondary and tertiary amines, substituted amines including naturally occurring substituted amines, cyclic amines, basic ion exchange resins, and the like, specifically isopropylamine, trimethylamine, diethylamine, triethylamine, tripropylamine and ethanolamine. In some embodiments, the salt is an edible acceptable salt, which is a salt suitable for inclusion in an ingestible composition, such as a food or beverage product. In some embodiments, the edible acceptable salt is a sodium salt or a potassium salt.

[0048] In certain aspects, the present disclosure provides flavor-modifying compositions comprising one or more flavor-modifying compounds selected from the group consisting of compounds 1-41 and edible acceptable salts thereof. Many of these compounds are available in certain species of Capsicum, such as Sichuan pepper or Szechuan pepper.

[0049] Thus, in some embodiments, the flavor modifying composition is a composition obtained by Zanthoxylum moniliforme oil. In some embodiments, Zanthoxylum moniliforme or Zanthoxylum moniliforme includes, but is not limited to, ingredient FEMA 4754 or ingredient N342 of GB2760, or ingredient EC / List No: 306-820-8, or ingredient CAS 97404-53-0.

[0050] Thus, in some embodiments, the flavor-altering composition is a composition obtained by extracting Zanthoxylum arborescens oil using an aqueous or water-miscible solvent system, such as a water / ethanol solvent system or a pure ethanol solvent system.

[0051] Uses and Methods In certain aspects, the disclosure provides the use of a flavor modifying compound or flavor modifying composition of the preceding aspects to enhance the sweetness of an ingestible composition. In certain related aspects, the disclosure provides a method of enhancing the sweetness of an ingestible composition, the method comprising introducing a flavor modifying compound or flavor modifying composition of the preceding aspects into the ingestible composition.

[0052] In certain aspects, the disclosure provides the use of a flavor modifying compound or flavor modifying composition of the preceding aspects to reduce the bitter taste of an ingestible composition. In certain related aspects, the disclosure provides a method of reducing the bitter taste of an ingestible composition, the method comprising introducing a flavor modifying compound or flavor modifying composition of the preceding aspects into the ingestible composition.

[0053] In certain aspects, the disclosure provides for the use of a flavor modifying compound or flavor modifying composition of the preceding aspects to reduce the astringent taste of an ingestible composition (such as the lingering aftertaste of high intensity sweeteners or a licorice aftertaste). In certain related aspects, the disclosure provides a method of reducing the astringent taste of an ingestible composition, the method comprising introducing into the ingestible composition a flavor modifying compound or flavor modifying composition of the preceding aspects.

[0054] In certain aspects, the disclosure provides the use of a flavor modifying compound or flavor modifying composition of the preceding aspects to enhance the texture of an ingestible composition. In certain related aspects, the disclosure provides a method of enhancing the texture of an ingestible composition, the method comprising introducing a flavor modifying compound or flavor modifying composition of the preceding aspects into the ingestible composition.

[0055] The aforementioned uses and methods include ingestible compositions. In addition to the ingestible composition features described above, the ingestible composition may incorporate any of the features or combinations of features described below.

[0056] Ingestible Composition In certain aspects, the disclosure provides an ingestible composition comprising a flavor modifying compound or flavor modifying composition according to the above embodiments. When introduced or used in an ingestible composition, the flavor modifying compound is used or introduced in the ingestible composition at a concentration in the range of 0.01 ppm to 1000 ppm, or 0.01 ppm to 900 ppm, or 0.01 ppm to 800 ppm, or 0.01 ppm to 700 ppm, or 0.01 ppm to 600 ppm, or 0.1 ppm to 500 ppm, or 0.1 ppm to 400 ppm, or 0.1 ppm to 300 ppm, or 0.1 ppm to 200 ppm, or 1 ppm to 100 ppm, or 1 ppm to 80 ppm, or 1 ppm to 60 ppm, or 1 ppm to 50 ppm, or 1 ppm to 40 ppm.

[0057] In some embodiments, the ingestible composition comprises one or more bitter tastants. In some embodiments, the bitter tastants are high intensity sweeteners, such as acesulfame potassium, aspartame, neotame, cyclamate, saccharin, sucralose, steviol glycodise (e.g., rebaudioside A, rebaudioside B, rebaudioside M, rebaudioside D, or rebaudioside E), and mogrosides (e.g., mogroside III, mogroside IV, mogroside V, siamenoside I, isomogroside V, mogroside IV ... E , Isomogroside IV, Mogroside III E , 11-oxomogroside V, or the 1,6-α isomer of siamenoside I). The flavour modifying compounds may therefore be suitable for use in reduced or zero sugar products to reduce the bitter taste imparted by low or zero calorie sweeteners.

[0058] In some embodiments, the bitter tastant is a potassium salt, such as potassium chloride, which is often used as a partial or complete replacement for sodium chloride in certain low or zero sodium foods. Thus, the flavor modifying compounds may be suitable for use in such products to reduce the bitter taste imparted by the potassium salt.

[0059] In some embodiments, the bitter tastant is a non-animal protein, such as a vegetable protein, an algae protein, or a mycoprotein. In some embodiments, the ingestible composition comprises a vegetable protein. Non-limiting examples of vegetable proteins include pea protein, soy protein, almond protein, cashew protein, canola (rapeseed) protein, chickpea protein, broad bean protein, sunflower protein, wheat protein, oat protein, barley protein, and potato protein. Such non-animal proteins are often used as partial or complete replacements for animal proteins in dairy and meat analogues. Therefore, flavor modifying compounds can be suitably used in such products to reduce the bitterness imparted by non-animal proteins. By blocking the bitterness of such proteins, flavor modifying compounds can reduce the perceived cereal and herbaceous notes experienced by consumers.

[0060] In some embodiments, the bitter tastants are caffeine, quinine, green tea, catechins, polyphenols (such as polyphenol antioxidants), tannins, green robusta coffee extract, green coffee extract, menthol, etc. Such compounds are commonly present in a variety of natural foods, such as tea and coffee, as well as packaged foods, such as instant tea, instant coffee, packaged beverages, etc. When one or more such bitter tastants are present, the flavor-modifying compounds are suitably used to mask the bitterness of such compounds and improve the taste of the product as perceived by the consumer.

[0061] In some embodiments, bitter tastant is a pharmaceutical compound.Non-limiting examples of pharmaceutical compounds with bitter taste include atropine, brinzolamide, chloramphenicol, chloroquine, clindamycin, dexamethasone, digoxin, diltiazem, diphenhydramine, docusate, dorzolamide, doxepin, doxylamine, enalapril, erythromycin, esomeprazole, famotidine, gabapentin, ginkgolide A, guaifenesin, L-histidine, lomefloxacin, methylprednisolone, ofloxacin, oleuropein, oxyphenonium, pirenzepine, prednisone, ranitidine, trapidil, trimethoprim and cetirizine.When one or more such pharmaceutical compounds are used in oral pharmaceutical formulations, taste-modifying compounds are preferably used to block the bitterness of such compounds and improve the taste of pharmaceuticals perceived by consumers.

[0062] In some embodiments, the bitter tastant is an oral care ingredient.Many oral care ingredients give bitter off-taste, which must be masked or blocked to improve consumer product acceptance.Non-limiting examples of such oral care ingredients include menthol, menthol analogs, mint extracts, sodium bicarbonate, alkali metal salts of peroxymonosulfate (potassium peroxymonosulfate), cetylpyridinium chloride, lauramidopropyl betaine, cocamidopropyl betaine, arginine, hydrogen peroxide, chlorhexidine gluconate, potassium nitrate, pentasodium triphosphate, tetrasodium pyrophosphate, stannous fluoride, thymol, methyl salicylate, eucalyptol, thymol, cubebol, and any combination thereof.When one or more such oral care compounds are used in oral care products, the taste modifying compound is preferably used to block the bitterness of such compounds and improve the taste of the oral care product as perceived by consumers.

[0063] In some embodiments, the bitter tasting substance is a bittering agent found in citrus fruits, such as limonin, nomellin or naringin. Many citrus-containing preparations give a bitter off-taste, which must be masked or blocked to improve consumer acceptance of the product. This bitter off-taste can sometimes be caused by citrus greening disease, in which citrus fruits turn green before they are fully ripe. When one or more such citrus bitter tasting substances are present in a product, the flavor modifying compound is preferably used to block the bitterness of such compounds and improve the taste of the citrus product as perceived by consumers.

[0064] In some embodiments, the ingestible composition comprises one or more flavonoids, dihydrochalcones, or other related compounds. Non-limiting examples of such compounds include hesperetin dihydrochalcone, hesperetin dihydrochalcone-4'-O' glucoside, neohesperetin dihydrochalcone, brazzein, hesperidin, phyllodulcin, naringenin, naringin, phloretin, (2R,3R)-3-acetoxy-5,7,4'-trihydroxyflavanone, (2R,3R)-3-acetoxy-5,7,3'-trihydroxy-4'-methoxyflavanone, rubusoside, thaumatin, monellin, miraculin, glycyrrhizin, and the edible forms thereof. Acceptable salts (such as monoammonium salts), naringin dihydrochalcone, myricetin, nobiletin, polymethoxyflavones, mixed methoxy- and hydroxyflavones, quercetin, amino acids, eriodictyol, homoeriodictyol, trilobatin, phloridzin, monellin, malonyl steviol glycoside, malonyl mogroside, malonyl rubusoside, eriodictyol-6-glucoside, glucosylated steviol glycoside (GSG), glucosylated mogroside, and glucosylated rubusoside. As used herein, the terms "glucosylated steviol glycoside" and "glucosylated mogroside" and "glucosylated rubusoside" refer to the product of enzymatic glucosylation of natural steviol glycoside or mogroside or rubusoside compounds. Glucosylation generally occurs via glycosidic bonds such as α-1,2, α-1,4, α-1.6, β-1,2, β-1,4, and β-1,6.Any of the foregoing compounds can be present in the ingestible composition in combination with the flavor modifying compounds disclosed herein at any suitable concentration, for example, in a range of from 0.01 ppm to 1000 ppm, or from 0.01 ppm to 900 ppm, or from 0.01 ppm to 800 ppm, or from 0.01 ppm to 700 ppm, or from 0.01 ppm to 600 ppm, or from 0.1 ppm to 500 ppm, or from 0.1 ppm to 400 ppm, or from 0.1 ppm to 300 ppm, or from 0.1 ppm to 200 ppm, or from 1 ppm to 100 ppm, or from 1 ppm to 80 ppm, or from 1 ppm to 60 ppm, or from 1 ppm to 50 ppm, or from 1 ppm to 40 ppm.

[0065] In some embodiments, the ingestible composition comprises a sweetener or a combination of sweeteners. In some embodiments, the sweetener is a common sugar sweetener, such as sucrose, fructose, glucose, as well as a sweetener composition comprising natural sugars, such as corn syrup (including high fructose corn syrup), or other syrups or sweetener concentrates derived from natural fruit and plant 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-albinose, 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, etc. In some embodiments, the sweetener is selected from aspartame, saccharin, acesulfame-K, cyclamate, sucralose, and artificial sweeteners such as alitame. In some embodiments, the sweetener is selected from the group consisting of cyclamic acid, mogrosides, tagatose, maltose, galactose, mannose, sucrose, fructose, lactose, allulose, neotame and other aspartame derivatives, glucose, D-tryptophan, glycine, maltitol, lactitol, isomalt, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolysates (HSH), stevioside, rebaudioside A, other sweet stevia-based glycosides, chemically modified steviol glycosides (e.g., glucosylated steviol glycosides), mogrosides, chemically modified mogrosides (e.g., glucosylated mogrosides), carrelame, and other guanidine-based sweeteners. In some embodiments, the sweetener is a combination of two or more of the sweeteners described in this paragraph. In some embodiments, the sweetener may be a combination of two, three, four or five sweeteners disclosed herein. In some embodiments, the sweetener may be a sugar.In some embodiments, the sweetener may 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 sucrose. In some embodiments, the sugar is beet sugar. In some embodiments, the sugar may be sucrose, fructose, glucose or a combination thereof. In some embodiments, the sugar may be sucrose. In some embodiments, the sugar may be a combination of fructose and glucose.

[0066] Sweeteners may also include, for example, sweetener compositions containing 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 hydrolysates (HSH), or other syrups or sweetener concentrates derived from natural fruit and plant sources, or semi-synthetic "sugar alcohol" sweeteners such as polyols. Non-limiting examples of polyols in some embodiments include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerin), threitol, galactitol, palatinose, reduced isomaltooligosaccharides, reduced xylooligosaccharides, reduced gentiooligosaccharides, reduced maltose syrup, reduced glucose syrup, isomaltulose, maltodextrin, and the like, as well as sugar alcohols or any other carbohydrates that can be reduced and do not adversely affect the taste, or combinations thereof.

[0067] The sweetener may be a natural or synthetic sweetener, including, but not limited to, agave inulin, agave nectar, agave syrup, amazake, brazzein, brown rice syrup, coconut crystals, coconut sugar, coconut syrup, date sugar, fructans (also called inulin fiber, fructooligosaccharides or oligofructose), green stevia powder, stevia rebaudiana, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, rebaudioside I ... Rebaudioside E, Rebaudioside F, Rebaudioside I, Rebaudioside H, Rebaudioside L, Rebaudioside K, Rebaudioside J, Rebaudioside N, Rebaudioside O, Rebaudioside M and other sweet stevia glycosides, stevioside, stevioside extract, honey, Jerusalem artichoke syrup, licorice root, Monk fruit (fruit, powder, or extract), Lucuma (fruit, powder, or extract), maple sap (e.g., Acer saccharum ( saccharum, Acer nigrum, Acer rubrum, Acer saccharinum, Acer platanoides, Acer negundo, Acer macrophyllum, Acer grandidentatum, Acer glabrum, Acer mono), maple syrup, maple sugar, walnut sap (including sap extracted from Juglans cinerea, Juglans nigra, Juglans ailatifolia, Juglans regia, Juglans regia), birch sap (e.g., Betula papyrifera, Betula alleghaniensis, Betula lenta, Betula nigra, Betula populifolia, Betulapopulifolia, Betula pendula), sycamore sap (e.g., Platanus occidentalis), ironwood sap (e.g., Ostrya virginiana), virginiana), mascovado, molasses (e.g., blackstrap molasses), molasses sugar, monatin, monellin, sucrose (also called natural sugar, unrefined sucrose, or sucrose), palm sugar, panocha, piloncillo, rapadura, raw sugar, rice syrup, sorghum, sorghum syrup, cassava syrup (also called tapioca syrup), thaumatin, yacon root, malt syrup, barley malt syrup, barley malt powder, beet sugar, sucrose, crystalline fruit juice crystals, caramel, carbitol, carob syrup, castor sugar, hydrogenated starch hydrolysate, invert sucrose juice (hydrolyzed cane sugar),juice), hydrolyzed starch, invert sugar, anethole, arabinogalactan, arop, syrup, P-4000, acesulfame potassium (also called acesulfame K or ace-K), alitame (also called aclame), advantame, aspartame, bayunoside, neotame, benzamide derivatives, bernademe, candelal, carrelame and other guanidine sweeteners, vegetable fiber, corn sugar, coupling sugar, curculin, cyclamate, cyclocaryoside I, demerara, Dextran, dextrin, saccharified malt, dulcin, sucrose, valgin, dulcoside A, dulcoside B, emulin, enoxolone, maltodextrin, saccharin, estragole, ethyl maltol, glucine, gluconic acid, glucono-lactone, glucosamine, glucoronic acid, glycerol, glycine, glycyphillin, glycyrrhizin, glycyrrhetinic acid monoglucuronide, golden sugar, yellow sugar, golden syrup, granulated sugar, gynostemma, hernan Dulcin, isomerized liquid sugar, jalab, chicory root dietary fiber, kynurenine derivatives (including N'-formyl-kynurenine, N'-acetyl-kynurenine, 6-chloro-kynurenine), galactitol, litesse, ligicane, lycasin, lugusnum, guanidine, falannum, mabinlin I, mabinlin II, maltol, multisorb, maltodextrin, maltotriol, mannosamine, miraculin, starch syrup, mogrosides (e.g. mogroside IV, mogroside V, and and neomogroside), mukurodiosides, nano sugar, naringin dihydrochalcone, neohesperidin dihydrochalcone, nib sugar, nigero-oligosaccharides, norbu, orgeat syrup, osladin, pekmez, pentasin, periandrin I, perillaldehyde, perillartine, petophyllum, phenylalanine, phlomisoside I, phlorogidin, phyllodulcin, polyglycitol syrup, polypodoside A, pterocaryoside A, pterocaryoside B, rebiana, refiner syrup, rub syrup, rubusoside, selligueain A, shugr, siamenoside I, siraitiagrosvenorii, soy oligosaccharides, Splenda, SRI oxime V, steviol glycosides, steviolbioside, stevioside, strogin 1, 2 and 4, sucronic acid, sucrononate, sugar, suosan, phlorizin, super aspartame, tetrasaccharide, threitol, molasses, trilobtain, tryptophan and derivatives (6-trifluoromethyl-tryptophan, 6-chloro-D-tryptophan), vanilla sugar, volemitol, birch xylose, aspartame-acesulfame, asgulin, and combinations or blends of any two or more thereof.

[0068] Additional sweeteners also include combinations of any two or more of any of the aforementioned sweeteners. In some embodiments, the sweetener may include a combination of two, three, four or five sweeteners disclosed herein. In some embodiments, the sweetener may be a sugar. In some embodiments, the sweetener may be a combination of one or more sugars and 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 of, or (in some embodiments) substantially free of, stevia-derived sweeteners, such as steviol glycosides, glucosylated steviol glycosides, or rebaudiosides.

[0069] In some embodiments, the ingestible composition comprises an acidic tastant, such as an organic acid, non-limiting examples of which include acetic acid, malonic acid, citric acid, lactic acid, and the like.

[0070] The ingestible compositions, in certain embodiments, can include any additional ingredient or combination of ingredients commonly used in food and beverage products, including, but not limited to, Acids, including, for example, citric acid, phosphoric acid, ascorbic acid, sodium sulfate, lactic acid, or tartaric acid; For example, bitter components including caffeine, quinine, green tea, catechins, polyphenols, green robusta coffee extract, green coffee extract, potassium chloride, menthol, or proteins (such as proteins and protein isolates derived from plants, algae, or fungi), Colorants containing, for example, caramel color, Red No. 40, Yellow No. 5, Yellow No. 6, Blue No. 1, Red No. 3, purple carrot, black carrot juice, purple sweet potato, vegetable juice, fruit juice, beta carotene, turmeric curcumin, or titanium dioxide; preservatives, such as sodium benzoate, potassium benzoate, potassium sorbate, sodium metabisulfate, sorbic acid, or benzoic acid; antioxidants, including, for example, ascorbic acid, disodium calcium EDTA, alpha tocopherol, mixed tocopherols, rosemary extract, grape seed extract, resveratrol, or sodium hexametaphosphate; For example, Resveratrol, Co-Q10, Omega-3 fatty acids, Theanine, Choline chloride (Cytocholine), Fibersol, Inulin (Chicory root), Taurine, Ginseng extract, Guanana extract, Ginger extract, L-Phenylalanine, L-Carnitine, L-Tartrate, D-Glucoronolactone, Inositol, Bioflavonoids, Echinacea, Ginkgo biloba, Yerba mate, Flaxseed oil, Garcinia cambogia lind extract, White tea extract, Ribose, Milk thistle extract, Grape seed extract, Pyroxyxine HCl (Vitamin B6), Cyanocobalamin (Vitamin B12), Niacinamide Vitamins or functional ingredients, including (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, Opacifiers, including, for example, ester gun, brominated vegetable oil (BVO), or sucrose acetate isobutyrate (SAIB); For example, sodium citrate, potassium citrate, or a buffer containing a salt; For example, propylene glycol, ethyl alcohol, glycerin, gum arabic (gum acacia), maltodextrin, modified corn starch, dextrose, natural flavors, natural flavors with other natural flavors (natural flavors WONF), natural and artificial flavors, artificial flavors, flavors containing silicon dioxide, magnesium carbonate, or tricalcium phosphate, or Examples include starches and stabilizers, including pectin, xanthan gum, carboxymethylcellulose (CMC), polysorbate 60, polysorbate 80, medium chain triglycerides, cellulose gel, cellulose gum, sodium caseinate, modified food starch, gum arabic (gum acacia), inulin or carrageenan.

[0071] The ingestible composition can have any suitable pH. In some embodiments, the flavor modifying compound enhances the sweetness of the sweetener under a wide range of pH, for example, from low to neutral pH. Low and neutral pH include, but are not limited to, pH of 1.5-9.0, or 2.5-8.5, 3.0-8.0, 3.5-7.5, and 4.0-7. In certain embodiments, the compounds disclosed and described herein, individually or in combination, can enhance the perceived sweetness of a fixed concentration of sweetener in a taste test at compound concentrations of 50 μM, 40 μM, 30 μM, 20 μM, or 10 μM, both at low and neutral pH values. In certain embodiments, the enhancement factor of the compounds disclosed and described herein, individually or in combination, at low pH is substantially similar to the enhancement factor of the compounds at neutral pH. Such consistent sweetness enhancing properties over a wide range of pH allow the compounds disclosed and described herein to be widely used, individually or in combination, in a wide variety of foods and beverages.

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

[0073] In some embodiments, the ingestible composition comprises vanillin or a vanillin analogue that imparts a vanilla flavor to the flavorant, hi some further embodiments, the ingestible composition comprises one or more lactones that impart a creamy flavor to the composition.

[0074] In some embodiments, the ingestible composition comprises a yeast extract, such as a yeast lysate. Such an extract can be obtained from any suitable yeast strain, where such an extract is suitable for human consumption. Non-limiting examples of such yeasts include Saccharomyces yeasts such as Saccharomyces cerevisiae or Saccharomyces pastorianus; Candida yeasts such as Candida utilis; Kluyveromyces yeasts such as Kluyveromyces lactis or Kluyveromyces marxianus; Pichia yeasts such as Pichia pastoris; Debaryomyces yeasts such as Debaryomyces hansenii; and Zygosaccharomyces yeasts such as Zygosaccharomyces mellis. In some embodiments, the yeast is yeast collected after brewing beer, sake, etc. In some embodiments, the yeast is yeast that has been subjected to a drying process after collection (dried yeast).

[0075] Such extracts can be produced by any suitable means. Generally, yeast extracts or lysates are made by extracting the contents of yeast cells from cell wall material. Often, digestive enzymes in the cells (or additional enzymes added to the composition) break down proteins and polynucleotides in the yeast into amino acids, oligopeptides (e.g., 2-10 peptides), nucleotides, oligonucleotides (2-10 nucleotides) and mixtures thereof. Yeast lysates can be prepared by dissolving yeast. For example, in some embodiments, yeast after culture is disrupted or dissolved by enzymatic degradation, autolysis, alkaline extraction, hot water extraction, acid degradation, ultrasonic disruption, homogenizer disruption, freeze-thawing, or the like (two or more of these may be used in combination) to obtain yeast lysates. Yeast can be cultured by conventional methods. In some embodiments, yeast after culture is heat-treated and then treated with a lytic enzyme to obtain enzymatic lysates. The heat treatment conditions are, for example, 80°C to 90°C for 5 to 30 minutes. As the lytic enzyme used in the enzymatic decomposition method, various enzymes can be used as long as they can dissolve the cell wall of yeast. The reaction conditions can be set to be optimal or suitable for the lytic enzyme used, and specific examples include a temperature of 50°C to 60°C and a pH of 7.0 to 8.0. The reaction time is not particularly limited, and can be, for example, 3 to 5 hours.

[0076] Compositions comprising yeast lysate can be obtained from a variety of commercial sources. For example, in some embodiments, the yeast lysate is provided by a flavor additive sold under the name MODUMAX (DSM Food Specialties BV, Delft, Netherlands).

[0077] In some embodiments, the ingestible composition comprises a sweetener enhancer. Any suitable sweetener enhancer, including synthetic sweetener enhancers, natural sweetener enhancers, or any combination thereof, can be used in the ingestible compositions disclosed herein.

[0078] Examples of suitable synthetic sweetener enhancers include, but are not limited to, N-(1-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methylpropan-2-yl)isonicotinamide, or any of its edible acceptable salts, 3-hydroxybenzoic acid, or any of the compounds described in U.S. Pat. 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. Suitable examples of natural sweetener enhancers include, but are not limited to, hesperetin dihydrochalcone, hesperetin dihydrochalcone-4'-O' glucoside, neohesperetin dihydrochalcone, brazzein, hesperidin, phyllodulcin, naringenin, naringin, phloretin, glucosylated steviol glycosides, (2R,3R)-3-acetoxy-5,7,4'-trihydroxyflavanone, (2R,3R)-3-acetoxy-5,7,3'-trihydroxy-4'-methoxyflavanone, rubusoside, thaumatin, monellin, miraculin, glycyrrhizin and edible acceptable salts thereof (such as monoammonium salts), naringin dihydrochalcone, myricetin, nobiletin, polymethoxyflavones, mixed methoxy- and hydroxyflavones, quercetin, certain amino acids, and the like. As used herein, the term "glucosylated steviol glycosides" refers to the products of enzymatic glucosylation of natural steviol glycoside compounds. Glucosylation generally occurs through glycosidic linkages such as α-1,2, α-1,4, α-1.6, β-1,2, β-1,4, and β-1,6 linkages.

[0079] In some embodiments of any of the foregoing embodiments, the ingestible composition comprises 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, or a edible acceptable salt thereof. In some embodiments, the ingestible composition comprises N-(1-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methyl-propan-2-yl)isonicotinamide, or a edible acceptable salt thereof. In some embodiments, the ingestible composition comprises N-(1-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methyl-propan-2-yl)isonicotinamide.

[0080] In some embodiments, the ingestible composition comprises one or more umami enhancing compounds. Such umami enhancing compounds include, but are not limited to, naturally occurring compounds or synthetic compounds, such as any of the compounds described in U.S. Patents 8,735,081, 8,124,121, and 8,968,708. In some embodiments, the umami enhancing compound is (2R,4R)-1,2,4-trihydroxy-heptadeca-16-ene, (2R,4R)-1,2,4-trihydroxyheptadeca-16-yne, or a mixture thereof. In some embodiments, the umami enhancing compound is (3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol diacetate. In some embodiments, the umami enhancing compound is N-(heptan-4-yl)benzo-[d][1,3]dioxole-5-carboxamide.

[0081] In some further embodiments, the ingestible composition comprises one or more cooling-promoting compounds, including, but not limited to, naturally occurring compounds such as menthol or analogs thereof, or synthetic compounds, such as any of the compounds described in U.S. Patent Nos. 9,394,287 and 10,421,727. Non-limiting examples include N-ethyl-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, N-(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, (E / Z)-2-methyl-2-butenal, (E / Z)-2-isopropyl-5-methyl-2-hexenal, phloretin, naringenin, and any combination thereof.

[0082] In some further embodiments, the ingestible composition comprises one or more bitter taste blocking or bitter taste masking compounds. Such bitter taste blocking or bitter taste masking compounds include, but are not limited to, naturally occurring or synthetic compounds, such as any of the compounds described in U.S. Patent Nos. 8,076,491, 8,445,692 and 9,247,759. Non-limiting examples include 3-(1-((3,5-dimethylisoxazol-4-yl)-methyl)-1H-pyrazol-4-yl)-1-(3-hydroxybenzyl)-imidazolidine-2,4-dione, 4-(2,2,3-trimethyl-cyclopentyl)butanoic acid, 3β-hydroxydihydrocostunolide, 3β-hydroxyperenolide, probenecid, sakuranetin, 6-methoxysakuranetin, jaceocidin, 4′-fluoro-6-methoxyflavonone, 6,3′-dimethoxyflavonone, 6-methoxyflavonone, γ-aminobutyric acid, Nα,Nα-bis(carbomethyl)-L-lysine. , (+ / -) abscisic acid, sodium gluconate, monosodium glutamate, sodium acetate, homoeriodictyol, sterubin, eriodictyol, 2,4,dihydrobenzoic acid, neodiosmin, 1-carboxymethyl-5-hydroxy-2-hydroxymethylpyridinium, flavan-3-spiro-C-glycoside, poly-gamma-glutamic acid, alpha,alpha-trehalose, taurine, (2)-gingerdione, 2,4,dihydroxybenzoic acid, L-theanine, enterodiol, lariciresinol, enterolactone, matairesinol, and any combination thereof.

[0083] In some further embodiments, the ingestible composition comprises one or more acidity regulating compounds.

[0084] In some further embodiments, the ingestible composition comprises one or more texture modifying compounds, including but not limited to tannins, cellulosic materials, bamboo powder, and the like.

[0085] In some further embodiments, the ingestible composition comprises one or more flavor-masking compounds, including, but not limited to, cellulosic materials, materials extracted from fungi, materials extracted from plants, citric acid, carbonic acid (or carbonates), and the like.

[0086] Flavoured products 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 soda, flavored water, tea, etc. In some other embodiments, the flavored product is a food product, such as yogurt. In some embodiments, the flavored product is an oral care product, such as toothpaste, mouthwash, dentrifrices, whitening agents, etc.

[0087] In embodiments where the flavored product is a beverage, the beverage may be selected from the group consisting of enhanced sparkling beverages, cola, lemon-lime flavored sparkling beverages, orange flavored sparkling beverages, grape flavored sparkling beverages, strawberry flavored sparkling beverages, pineapple flavored sparkling beverages, ginger ale, root beer, fruit juices, fruit flavored juices, juice drinks, nectars, vegetable juices, vegetable flavored juices, sports drinks, energy drinks, enhanced water drinks, enhanced waters with vitamins, near water drinks, coconut water, tea-based drinks, coffee, cocoa drinks, beverages containing dairy ingredients, beverages containing cereal extracts, and smoothies. In some embodiments, the beverage may be a soft drink.

[0088] In certain embodiments of any aspect, and in embodiments described herein that refer to a flavored product, the flavored product is a non-naturally occurring product, such as a packaged food or beverage product.

[0089] Further non-limiting examples of food and beverage products or formulations include sweet coatings, frostings, or glazes for such products or any entity included in the soup category, the dried prepared foods category, the beverage category, the ready meals category, the canned or preserved foods category, the frozen prepared foods category, the chilled prepared foods category, the snack foods category, the baked goods category, the confectionery category, the dairy category, the ice cream category, the meal replacements category, the pasta and noodles category, and the sauces, dressings, condiments category, the baby food category, and / or the spreads category.

[0090] In general, the soup category refers to canned / preserved, dehydrated, instant, chilled, UHT and frozen soups. For the purposes of this definition, soup means food prepared from meat, poultry, fish, vegetables, grains, fruits and other ingredients and cooked in a liquid that may contain some or all visible portions of these ingredients. Soups may be clear (as broths) or thick (as chowders), smooth, pureed or chunky, ready to serve, semi-condensed or condensed, and may be served hot or cold, as the first or main course of a meal, or as a snack between meals (sipped in sips like a beverage). Soups may be used as ingredients for preparing other meal components and may range from broths (consomme) to sauces (cream or cheese-based soups).

[0091] The dehydrated and prepared foods category generally refers to: (i) cooking aid products, e.g., powders, granules, pastes, concentrated liquid products, e.g., compressed cubes, tablets, or concentrated bouillons, bouillon and bouillon-like products in powder or granule form, sold separately as finished products (regardless of technology) or as an ingredient in products, sauces and recipe mixes; (ii) dietary solution products, e.g., dehydrated and freeze-dried soups, e.g., dehydrated soup mixes, dehydrated instant soups, dehydrated semi-cooked soups, ready-made dishes including pasta, potato and rice dishes, dehydrated or ambient shelf-stable preparations of meals and single-serving entrees; (iii) meal accompaniment products, e.g., condiments, marinades, salad dressings, salad toppings, dips, bread crumbs, batter mixes, shelf stable spreads, barbecue sauces, liquid recipe mixes, concentrates, sauces or sauce mixes, e.g., salad recipe mixes, etc., sold in a dehydrated, liquid or frozen state, either as finished products or as an ingredient in products.

[0092] The beverage category generally refers 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 preparing beverages such as sodas, and dry powdered beverage pre-mixes. The beverage category also includes alcoholic drinks, soft drinks, sports drinks, isotonic drinks and hot drinks. Alcoholic drinks include but are not limited to beer, cider / perry, FAB, wine and spirits. Soft drinks include carbonated, e.g. cola and non-cola carbonated; fruit juices, e.g. juices, nectars, juice drinks and fruit-flavored drinks; bottled waters, e.g. sparkling water, spring water and purified water / table water; functional drinks, e.g. sports drinks, energy drinks or elixir drinks, which may be carbonated or non-carbonated; concentrates, e.g. liquid and powder concentrates prepared into portions for drinking. Beverages include, but are not limited to, coffee or iced coffee, either hot or cold, such as brewed, instant and combination coffee; tea or iced tea, such as black tea, green tea, white tea, oolong tea and flavored tea; and other beverages, including flavored, malt or plant-based powders, granules, blocks or tablets mixed with milk or water.

[0093] The snack food category generally refers to any food that can be a light informal meal, including but not limited to sweet and savory snacks, and snack bars. Examples of snack foods include, but are not limited to, fruit snacks, chips / crisps, extruded snacks, tortilla / corn 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.

[0094] The baked goods category generally refers to any edible product whose preparation method involves exposure to heat or excessive sunlight. Examples of baked goods include, but are not limited to, bread, buns, cookies, muffins, cereals, toaster pastries, pastries, waffles, tortillas, biscuits, pies, bagels, tarts, quiches, cakes, any baked food product, and any combination thereof.

[0095] The ice cream category generally refers to frozen desserts that contain cream and sugar and flavorings. Examples of ice cream include, but are not limited to, impulse ice cream; take-home ice cream; frozen yogurt and artisanal ice cream; soy, oat, bean (e.g., red bean and mung bean), and rice-based ice cream.

[0096] The confectionery category generally refers to sweet tasting edible products. Examples of confectionery include, but are not limited to, candy, gelatin, chocolate confectionery, sugar confectionery, gum, and the like, and any combination products.

[0097] The meal replacement category generally refers to any food product intended to replace a regular meal, especially for people who are health or fitness conscious. Examples of meal replacements include, but are not limited to, slimming products and recovery products.

[0098] The ready meal category generally refers to any food that can be served as a meal without extensive preparation or processing. Ready meals include products to which recipe "skill" has been added by the manufacturer, resulting in a high degree of speed, completeness, and convenience. Examples of ready meals include, but are not limited to, canned / preserved, frozen, dried, chilled ready meals; dinner mixes; frozen pizza; chilled pizza; and prepared salads.

[0099] The pasta and noodles category includes any pasta and / or noodles, including but not limited to canned, dried and chilled / fresh pasta; and plain, instant, chilled, frozen and snack noodles.

[0100] The canned / preserved food category includes, but is not limited to, canned / preserved meat and meat products, fish / seafood, vegetables, tomatoes, beans, fruit, ready meals, soups, pasta, and other canned / preserved foods.

[0101] The frozen processed foods category includes, but is not limited to, frozen processed red meat, processed poultry, processed fish / seafood, processed vegetables, meat substitutes, processed potatoes, bakery products, desserts, ready meals, pizza, soups, noodles and other frozen foods.

[0102] The dry processed food category includes, but is not limited to, rice, dessert mixes, dry ready meals, dehydrated soups, instant soups, dry pasta, plain noodles and instant noodles. The chilled processed food category includes, but is not limited to, chilled processed meats, processed fish / seafood products, lunch kits, fresh cut fruit, ready meals, pizza, prepared salads, soups, fresh pasta and noodles.

[0103] The sauces, dressings and condiments category includes, but is not limited to, tomato paste and purees, bouillon / stock cubes, herbs and spices, monosodium glutamate (MSG), table sauces, soy-based sauces, pasta sauces, wet / cooking sauces, dry sauces / powder mixes, ketchup, mayonnaise, mustard, salad dressings, vinaigrettes, dips, pickle products and other sauces, dressings and condiments.

[0104] Baby food categories include, but are not limited to, milk or soy-based formulas; prepared, dry and other baby foods.

[0105] Spreads categories include, but are not limited to, jams and preserves, honey, chocolate spreads, nut-based spreads and yeast-based spreads.

[0106] The dairy category generally refers to edible products produced from mammalian milk. Examples of dairy products include, but are not limited to, drinking dairy products, cheese, yogurt and sour milk drinks, and other dairy products.

[0107] Additional examples of flavored products, particularly food and beverage products or formulations, are provided below. Exemplary ingestible compositions include one or more of confectionery, chocolate confectionery, tablets, countlines, bagged selflines / softlines, boxed assortments, standard boxed assortments, twist wrapped miniatures, and the like. miniatures, seasonal chocolates, chocolates with toys, alfajores, other chocolate confectionery, mints, standard mints, power mints, boiled sweets, pastel tablets, gum, jellies and chews, toffee, caramel and nougat, medicated confectionery, lollipops, liquorice, other sugar confectionery, bread, packaged / industrial bread, unpackaged / artisan bread, pastries, cakes, packaged / industrial cakes, unpackaged / artisan cakes, cookies, chocolate coated biscuits, sandwich biscuits, filled biscuits, savoury biscuits and crackers, bread substitutes, breakfast cereals, rte cereals, family breakfast cereals, flakes, muesli, other cereals, children's breakfast cereals, hot cereals, ice cream, impulse ice cream, single portion dairy ice cream, single portion water ice cream, multi-pack dairy ice cream ice cream, multipack water ice cream, take away ice cream, take away dairy ice cream, ice cream desserts, bulk ice cream, take away water ice cream, frozen yogurt, artisanal ice cream, dairy products, milk, raw milk / pasteurized milk, full fat raw milk / pasteurized milk, semi skimmed raw milk / pasteurized milk, long life / uht milk, full fat long life / uht milk, semi skimmed long life / uht milk, non fat long life / uht milk, goat milk, condensed milk / evaporated milk, plain condensed milk / evaporated milk, flavoured, functional and other condensed milk, flavoured milk drinks, dairy only flavoured milk drinks, flavoured dairy drinks with fruit juice, soy milk, sour milk drinks, fermented dairy drinks, coffee whitener, milk powder, flavoured milk powder drinks, cream, cheese, processed cheese, spreadable processed cheese, non spreadable processed cheese, raw cheese,Spreads Raw Cheese, Hard Cheese, Packaged Hard Cheese, Unpackaged Hard Cheese, Yogurt, Plain Yogurt / Natural Yogurt, Flavoured Yogurt, Fruit Yogurt, Probiotic Yogurt, Drinking Yogurt, Regular Drinking Yogurt, Probiotic Drinking Yogurt, Refrigerated Shelf Stable Desserts, Dairy Based Desserts, Soy Based Desserts, Chilled Snacks, Fromage Frais and Quark, Plain Fromage Frais and Quark, Flavoured Fromage Frais and Quark, Savory Fromage Frais and Quark, Sweet and Savory Snacks, Fruit Snacks, Chips / Crisps, Extruded Snacks, Tortilla / Corn Chips, Popcorn, Pretzels, Nuts, Other Sweet and Savory Snacks, Snack Bars, Granola Bars, Breakfast Bars, Energy Bars, Fruit Bars, Other Snack Bars, Meal Replacement Products, Slimming Products, Recovery Drinks, Ready Meals, Canned Ready Meals, Frozen Ready Meals, Dried Ready Meals, Chilled Ready Meals, Dinner Mixes, Frozen Pizza, Chilled Pizza, Soups, Canned Soups, Dehydrated Water soup, Instant soup, Chilled soup, Hot soup, Frozen soup, Pasta, Canned pasta, Dried pasta, Chilled / fresh pasta, Noodles, Plain noodles, Instant noodles, Cup / bowl instant noodles, Pouch instant noodles, Chilled noodles, Snack noodles, Canned food, Canned meat and meat products, Canned fish / seafood, Canned vegetables, Canned tomatoes, Canned beans, Canned fruits, Canned ready meals, Canned soup, Canned pasta, Other canned food, Frozen food, 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 bakery products, frozen desserts, frozen ready meals, frozen pizza, frozen soups, frozen noodles, other frozen foods, dehydrated foods, dessert mixes, dehydrated ready meals, dehydrated soups, instant soups, dehydrated pasta, plain noodles, instant noodles, cup / bowl instant noodles, pouch instant noodles, chilled foods, chilled processed meat, chilled fish / seafood products, chilled processed fish, chilled coated fish, chilled smoked fish, chilled lunch kits, chilled ready meals, chilled pizza, chilled soups, chilled / fresh pasta,chilled noodles, oils and fats, olive oil, vegetable seed oils, cooking oils and fats, butter, margarine, spreadable oils and fats, functional spreadable oils and fats, sauces, dressings and condiments, tomato paste and puree, bouillon / stock cubes, stock cubes, gravy granules, liquid stocks and fonds, herbs and spices, fermented sauces, soy based sauces, pasta sauces, wet sauces, dry sauces / powder mixes, ketchup, mayonnaise, regular mayonnaise, mustard, salad dressings, regular salad dressings, low fat salad dressings, vinaigrettes, dips, pickle products, other sauces, dressings and condiments, baby food, formulas, standard formulas, follow-on formulas, toddler formulas, hypoallergenic formulas, prepared baby foods, dry baby foods, other baby foods, spreads, jams and preserves, honey, chocolate spreads, nut based spreads, and yeast based spreads. Exemplary ingestible compositions also include confectionery, bakery products, ice cream, dairy products, sweet and savory snacks, snack bars, meal replacement products, ready meals, soups, pastas, noodles, canned foods, frozen foods, dry foods, chilled foods, fats and oils, baby foods or spreads, or mixtures thereof. Exemplary ingestible compositions also include breakfast cereals, sweetened drinks, or solid or liquid concentrate compositions for preparing beverages, ideally allowing for the reduction of the concentration of previously known sugar or artificial sweeteners.

[0108] Some embodiments provide chewable compositions that may or may not be intended to be swallowed. In some embodiments, the chewable compositions may be gums, chewing gums, sugar gums, sugarless gums, functional gums, bubble gums, containing the compounds disclosed and described herein, individually or in combination.

[0109] Typically, at least a sweet receptor modulating amount, a sweet receptor ligand modulating amount, a sweet flavor modulating amount, a sweet flavor agent amount, a sweet flavor enhancing amount, or a therapeutically effective amount of one or more of the present compounds, optionally in the presence of a sweetener, is added to an ingestible composition such that the sweet flavor modified ingestible composition has increased sweetness compared to an ingestible composition prepared without the compounds of the present invention, as determined by procedures generally known in the art, generally by a human or animal, or, in the case of formulation testing, by a majority of a panel of at least eight human taste testers.

[0110] In some embodiments, the compounds disclosed and described herein, individually or in combination, modulate the sweetness or other taste characteristics of other natural or synthetic sweeteners and ingestible compositions made therefrom. In one embodiment, the compounds disclosed and described herein, individually or in combination, can be used or provided at their ligand-enhanced concentrations. For example, the compounds disclosed and described herein, individually or in combination, can be present in amounts of 0.001 ppm to 100 ppm, or within the narrower alternative ranges of 0.1 ppm to 50 ppm, 0.01 ppm to 40 ppm, 0.05 ppm to 30 ppm, 0.01 ppm to 25 ppm, or 0.1 ppm to 30 ppm, or 0.1 ppm to 25 ppm, or 1 ppm to 30 ppm, or 1 ppm to 25 ppm.

[0111] In some embodiments, the ingestible compositions disclosed herein may be provided individually or in combination, for example, in a flavor concentrate formulation suitable for subsequent processing to produce a ready-to-use (i.e., ready-to-serve) product. A "flavor concentrate formulation" refers to a formulation that is to be reconstituted with one or more dilution media to become a ready-to-use composition. The term "ready-to-use composition" is used interchangeably herein with "ingestible composition", which refers to any substance that can be taken by mouth, whether or not it is intended for consumption, alone or together with another substance. In one embodiment, a ready-to-use composition includes a composition that can be directly consumed by a human or animal. A flavor concentrate formulation is typically used by mixing with or diluting with one or more dilution media, for example, any consumable or ingestible ingredient or product, to impart or modify one or more flavors to the dilution medium. Such a method of use is often referred to as reconstitution. Reconstitution can be performed in a domestic or industrial environment. For example, a frozen fruit juice concentrate can be reconstituted with water or other aqueous medium by a consumer in the kitchen to obtain a ready-to-use fruit juice beverage. In another example, soft drink syrup concentrates can be reconstituted with water or other aqueous media by manufacturers on a large industrial scale to produce ready-to-use soft drinks. Because flavor concentrate formulations have higher concentrations of flavoring agents or flavor modifiers than ready-to-use compositions, flavor concentrate formulations are typically not suitable for direct consumption without reconstitution. There are many benefits to the use and production of flavor concentrate formulations. For example, one benefit is that flavor concentrate formulations can be reconstituted at the time of use by the addition of a suitable solvent, solid or liquid, thus reducing the weight and volume of shipping.

[0112] The flavored products according to any of the foregoing embodiments also, in certain embodiments, comprise one or more additional flavor modifying compounds, such as a compound that enhances sweetness (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), a compound that blocks bitterness, a compound that enhances umami, a compound that reduces sourness, a compound that enhances saltiness, a compound that enhances cooling effect, or any combination of the foregoing.

[0113] In certain embodiments of any aspect, and in embodiments described herein referring to a sweetening or flavoring concentrate, the sweetening or flavoring concentrate is a composition specially manufactured for the production of a non-naturally occurring product, e.g., a flavored product, such as a food or beverage product.

[0114] In one embodiment, the flavor concentrate formulation comprises i) the compound disclosed and described herein, either individually or in combination, ii) a carrier, and iii) optionally at least one adjuvant. The term "carrier" refers to a normally inert accessory substance, such as a solvent, binder, or other inert medium, which is used in combination with the compound and one or more optional adjuvants to form a formulation. For example, water or starch can be a carrier for the flavor concentrate formulation. In some embodiments, the carrier is the same as the dilution medium for reconstituting the flavor concentrate formulation, and in other embodiments, the carrier is different from the dilution medium. The term "carrier" as used herein includes, but is not limited to, a carrier that is acceptable for ingestion.

[0115] The term "adjuvant" refers to an additive that supplements, stabilizes, maintains or enhances the intended function or effectiveness of an active ingredient, such as a compound of the present invention. In one embodiment, the at least one adjuvant includes one or more flavoring agents. The flavoring agents may be of any flavor known to the skilled artisan or consumer, such as the flavors of chocolate, coffee, tea, mocha, French vanilla, peanut butter, chai, or combinations thereof. In another embodiment, the at least one adjuvant includes one or more sweeteners. The one or more sweeteners may be any of the sweeteners described in this application. In another embodiment, the at least one adjuvant includes 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. Pat. No. 6,468,576, the contents of which are incorporated herein by reference in their entirety for all purposes.

[0116] In one embodiment, the flavor concentrate formulation may be in a form selected from the group consisting of liquids, including solutions and suspensions, solids, foams, pastes, gels, creams, and combinations thereof, such as liquids containing a certain amount of solids. In one embodiment, the flavor concentrate formulation is in the form of a liquid, including aqueous and non-aqueous. In some embodiments, the flavor concentrate formulation may be carbonated or non-carbonated.

[0117] The flavor concentrate formulation may further include a freezing point depressant, a nucleating agent, or both as at least one adjuvant. A freezing point depressant is an ingestibly acceptable compound or agent that can depress the freezing point of the liquid or solvent to which the compound or agent is added. That is, a liquid or solution containing the freezing point depressant has a lower freezing point than a liquid or solvent without the freezing point depressant. In addition to depressing the starting freezing point, the freezing point depressant can also reduce the water activity of the flavor concentrate formulation. Examples of freezing point depressants include, but are not limited to, carbohydrates, oils, ethyl alcohol, polyols such as glycerol, and combinations thereof. A nucleating agent refers to an ingestibly acceptable compound or agent that can promote nucleation. The presence of a nucleating agent in the flavor concentrate formulation can improve the texture of the frozen blushes of the frozen slush by increasing the number of desirable ice crystallization centers, and help maintain the physical properties and performance of the slush at freezing temperatures. Examples of nucleating agents include, but are not limited to, calcium silicate, calcium carbonate, titanium dioxide, and combinations thereof.

[0118] In one embodiment, the flavor concentrate formulation is formulated to have a low water activity to extend shelf life. Water activity is the ratio of the vapor pressure of water in the formulation to the vapor pressure of pure water at the same temperature. In one embodiment, the flavor concentrate formulation has a water activity of less than about 0.85. In another embodiment, the flavor concentrate formulation has a water activity of less than about 0.80. In another embodiment, the flavor concentrate formulation has a water activity of less than about 0.75.

[0119] In one embodiment, the flavor concentrate formulation has the compound at a concentration at least twice as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 5 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 10 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 15 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 20 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 30 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 40 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 50 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration of at least 60 times the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration of up to 100 times the concentration of the compound in the ready-to-use composition.

[0120] In some embodiments, flavorants can be used in many different physical forms known in the art to provide an initial burst of flavor and / or a long-term sensation of flavor, including, but not limited to, free forms such as spray-dried forms, powdered forms, beaded forms, encapsulated forms, and mixtures thereof.

[0121] In some embodiments, the ingestible composition comprises a flavor modifying compound according to any of the above embodiments and a bulking agent.Suitable bulking agents include, but are not limited to, maltodextrin (10DE, 18DE, or 5DE), corn syrup solids (20 or 36DE), sucrose, fructose, glucose, invert sugar, sorbitol, xylose, ribulose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharides, cellulose and cellulose derivatives, and the like, and mixtures thereof.In addition, granulated sugar (sucrose) or other caloric sweeteners such as crystalline fructose, other carbohydrates, or sugar alcohols can be used as bulking agents, since they provide good content uniformity without adding significant calories.

[0122] In one embodiment, the at least one bulking agent may be a bulking agent described in US Pat. No. 8,993,027.

[0123] In one embodiment, the at least one bulking agent may be a bulking agent described in US Pat. No. 6,607,771.

[0124] In one embodiment, the at least one bulking agent may be a bulking agent described in US Pat. No. 6,932,982.

[0125] In some embodiments, the tabletop sweetener composition may further comprise at least one anti-caking agent. As used herein, the phrases "anti-caking agent" and "flow agent" refer to any composition that prevents, reduces, inhibits, or inhibits at least one sweetener from attaching to, binding to, or contacting another sweetener molecule. Alternatively, an anti-caking agent can refer to any composition that aids in content uniformity and uniform dissolution. Non-limiting examples of anti-caking agents include cream of tartaric acid, calcium silicate, silicon dioxide, microcrystalline cellulose (Avicel, FMC BioPolymer, Philadelphia, PA), and tricalcium phosphate. In one embodiment, the anti-caking agent is present in the tabletop sweetener composition in an amount of about 0.001 to about 3% by weight of the tabletop sweetener composition.

[0126] In some embodiments, the sweetener composition of any of the foregoing aspects and embodiments thereof is encapsulated using typical means for encapsulating flavor or aroma compounds. Non-limiting examples of such techniques include U.S. Patent Application Publication Nos. 2016 / 0235102, 2019 / 0082727, 2018 / 0369777, 2018 / 0103667, 2016 / 0346752, 2015 / 0164117, 2014 / 0056836, 2012 / 0027866, 2010 / 0172945, and the like. and 2007 / 0128234, as well as U.S. Patent Nos. 7,488,503, 6,416,799, 5,897,897, 5,786,017, 5,603,971, 4,689,235, 4,610,890, 3,704,137, 3,041,180, and 2,809,895. All of the foregoing patent publications and patents are incorporated herein by reference as if set forth in their entireties herein.

[0127] Non-animal protein materials and products made therefrom Products intended to replace or substitute 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 vegetable proteins, such as pea protein, soybean protein, almond protein, cashew protein, canola (rapeseed) protein, chickpea protein, broad bean protein, sunflower protein, wheat protein, oat protein, barley protein, potato protein, and combinations thereof.Due to the compositional differences between such plant-based materials and animal-derived materials, such as the lack of glutamic acid-containing proteins and glutathione, these products may lack the umami or kokumi flavor that consumers traditionally associate with meat or dairy products, or may have the bitter taste that animal proteins lack.

[0128] Thus, 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 zinc salt according to any of the above embodiments. In some further embodiments, the flavored product can include any of the combinations of features described above for ingestible compositions containing zinc salts. In some embodiments, the flavored product is a beverage, such as soy milk, almond milk, rice milk, oat milk, a protein drink, a meal replacement drink, or other similar products. In some other embodiments, the flavored product is a meat replacement product, such as a plant-based chicken product (e.g., a plant-based chicken nugget), a plant-based beef product (e.g., a plant-based burger), or 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 further embodiments, any such product contains additional ingredients and has additional features typically used in the preparation and / or manufacture of such products. For example, the flavor-modifying compound may be combined with other flavorings and taste modifiers, or even encapsulated in a particular material, according to known techniques in the relevant art. Suitable concentrations of the flavour modifying compounds are given above.

[0129] In some embodiments, the flavored product comprises one or more plant-based proteins that impart a bitter taste that is at least partially reduced by using a flavor modifying compound in the product. Such plant-based proteins include, but are not limited to, pea protein, soy protein, almond protein, cashew protein, canola (rapeseed) protein, chickpea protein, broad bean protein, sunflower protein, wheat protein, oat protein, barley protein, potato protein, and combinations thereof.

[0130] In some alternative embodiments similar to those described above, algae or fungal proteins or starches are used instead. In some embodiments, these flavored products also contain fiber to provide texture to the product. Fibers suitable for use include, but are not limited to, psyllium fiber, pea fiber, potato fiber, curdlan, soluble corn fiber (dextran and / or maltodextrin), citrus fiber, and combinations thereof. In such products, the flavor-modifying compound can be introduced in any suitable manner. In some embodiments, the flavor-modifying compound is incorporated into a flavored emulsion, such as a water-in-oil emulsion, along with other flavor-imparting ingredients.

[0131] Non-meat protein materials and products made therefrom Certain non-meat animal proteins, such as dairy proteins and proteins from bone broth, are commonly used in foods and are also sold as the main ingredient of certain protein powders. Such proteins can impart a bitter taste that consumers may not want. This is particularly true for protein isolates, such as whey protein, collagen protein, casein protein, and other protein isolates. Thus, the present disclosure provides ingestible compositions that include non-meat animal proteins and flavor-modifying compounds. The flavor-modifying compounds can be present in any suitable combination according to the embodiments described in the preceding sections of the present disclosure. In some embodiments, the non-meat animal protein is a bone protein, such as collagen protein, derived from the bones of animals, such as cows, pigs, donkeys, horses, chickens, ducks, goats, geese, rabbits, lambs, sheep, buffalo, ostriches, camels, and the like. In some embodiments, the non-meat animal protein is a milk protein, such as whey protein, casein protein, or any combination thereof. The milk can be the milk of any suitable animal, such as cows, donkeys, horses, sheep, buffalo, camels, and the like.

[0132] The flavor modifying compounds may also be included in certain food or beverage products that contain animal milk or ingredients derived from animal milk, such as cheese, cheese spreads, yogurt, kefir, milk, processed dairy products, cottage cheese, sour cream, butter, etc.

[0133] Blocking bitterness in pharmaceutical APIs Many drug compounds impart a bitter taste, which therefore limits the way in which they can be formulated and administered. Thus, in certain aspects, the present disclosure provides pharmaceutical compositions comprising a bitter tasting medicament active ingredient and a taste-modifying compound. Such pharmaceutical compositions can be in any form suitable for oral administration, such as tablets, lozenges, capsules, powders, liquid solutions, liquid suspensions, etc. Such pharmaceutical compositions can include any suitable pharmaceutical excipients, binders, etc., such as those described in Remington's Pharmaceutical Sciences. In some embodiments, the bitter tasting medicament active ingredient is an ion channel inhibitor, e.g., a proton channel inhibitor. Other examples of bitter tasting APIs whose bitterness is reduced by the taste-modifying compounds include, but are not limited to, atropine, brinzolamide, chloramphenicol, chloroquine, clindamycin, dexamethasone, digoxin, diltiazem, diphenhydramine, docusate, dorzolamide, doxepin, doxylamine, enalapril, erythromycin, esomeprazole, famotidine, gabapentin, ginkgolide A, guaifenesin, L-histidine, lomefloxacin, methylprednisolone, ofloxacin, oleuropein, oxyphenonium, pirenzepine, prednisone, ranitidine, trapidil, trimethoprim, and cetirizine.

[0134] Use in oral care products Oral care products often contain ingredients that give an astringent or bitter off-taste. Such ingredients include menthol, menthol analogs, mint extracts, sodium bicarbonate, alkali metal salts of peroxymonosulfate (potassium peroxymonosulfate), cetylpyridinium chloride, lauramidopropyl betaine, cocamidopropyl betaine, arginine, hydrogen peroxide, chlorhexidine gluconate, potassium nitrate, pentasodium triphosphate, tetrasodium pyrophosphate, stannous fluoride, thymol, methyl salicylate, eucalyptol, or any combination thereof. Suitable oral care products include toothpaste, mouthwash, whitening agents, dentifrices, etc. Such oral care products may include flavor modifying compounds to block or mask the bitterness of such compounds. EXAMPLES

[0135] The following examples are included to further illustrate the present invention. Of course, the examples should not be construed as specifically limiting the present invention. Variations of these examples within the scope of the claims are within the scope of the skilled artisan's awareness and are considered to be within the scope of the invention described and claimed herein. The reader will recognize that a person skilled in the art equipped with this disclosure and the skills in the art can prepare and use the present invention without exhaustive examples.

[0136] Example 1 - Sample Preparation, Zanthoxylum nigra Oil and Sanshool Extract Commercially available Zanthoxylum candida oil (R1) was used as the raw material for fractionation and sensory testing. The chemical composition of the commercial Zanthoxylum candida oil was analyzed by GCMS and U(H)PLC-HRMS, revealing the presence of the following compounds: hydroxy-α-sanshool, hydroxy-γ-sanshool, hydroxy-β-sanshool, hydroxy-ε-sanshool, bungeanool, isobungeanool, γ-sanshool, linalyl acetate, trans-sabinene acetate, α-terpinyl acetate, cis-sabinene acetate, 4-terpinenyl acetate, linalool, 4-terpinenol, 1,8-trimethylsilyl 1,2 ... -Cineole, α-terpineol, α-elemol, limonene, sabinene, myrcene, trans-sabinene hydrate, cis-sabinene hydrate, γ-terpinene, α-thujene, trans-β-ocimene, α-caryophyllene, germacrene D, δ-cadinene, α-terpinene, β-caryophyllene, γ-cadinene, glyceryl dicaprylate monocaprate, glyceryl 1,2-dicaprylate, glyceryl (1- or 2-)caprate caprylate, glyceryl tricaprylate, glyceryl 1,3-dicaprylate, and glyceryl 1-caprate 3-caprylate.

[0137] Approximately 40 g of Zanthoxylum moniliforme oil (R1) was mixed with 360 g of aqueous ethanol solution (53% w / w). The mixture was stirred (375 rpm) at 50° C. for 2 hours. After stirring, the solution was placed in a fume hood and cooled to room temperature. The mixture was then cooled to 4° C. overnight in a refrigerator. The oil phase was separated from the bottom aqueous phase. The aqueous phase was filtered through a 0.45 μm PTFE membrane filter. Approximately 16.0 g of oil phase and 358.0 g of aqueous ethanol extract (W2) were obtained. Both were kept refrigerated at 4° C. until use.

[0138] Approximately 40 g of Zanthoxylum moniliforme oil (R1) was mixed with 360 g of aqueous ethanol to form a solution (67% w / w). The resulting solution was stirred (375 rpm) at 50 degrees for 2 hours. The solution was then placed in a fume hood to allow the solution to cool to room temperature. The solution was then placed in a refrigerator and cooled to 4°C overnight. The oil phase was separated from the original mixture. The aqueous ethanol extract was filtered through a 0.45 μm PTFE membrane filter. Finally, approximately 13.0 g of oil phase and 361.0 g of aqueous ethanol extract (W3) were obtained. Both were kept at 4°C until use.

[0139] The chemical composition of the aqueous ethanol extract of Zanthoxylum candida oil was analyzed by GCMS and U(H)PLC-HRMS analysis. The following compounds were identified: linalyl acetate, limonene, linalool, sabinene, 4-terpinenol, α-terpinyl acetate, mycene, 1,8-cineole, trans-β-ocimene, germacrene D, α-terpineol, hydroxy-α-sanshool, hydroxy-β-sanshool, hydroxy-γ-sanshool, hydroxy-ε-sanshool; hydroxy-γ-isosanshool, hydroxy-γ-isosanshool I, bungeanool, isobungeanool, and sabinene. Sanshool, γ-sanshool, 2',3'-dihydroxy-α-sanshool, tetrahydrobundianol, 2,6,8-decatrienamide, N-(2-hydroxy-2-methylpropyl)-10-oxo-, 2,8,10-dodecatrienamide, N-(2-methyl-1-propen-1-yl)-7-oxo-, N-(2-hydroxy-2-methylpropyl)-2,4,8,10-dodecatetraenamide, (2E,6Z)-N-(2-hydroxy-2-methylpropyl)-2,6-dodecadienamide , 2,4-dodecadienamide, N-(2-hydroxy-2-methylpropyl)-(2E,4E)-, (2E)-N-(2-hydroxy-2-methylpropyl)-2-dodecenamide, (2E)-N-(2-hydroxy-2-methylpropyl)-2-dodecenamide, γ-dehydrosanshool, (2E,4E,8E,10E,12E)-N-(2-methyl-2-propen-1-yl)-2,4,8,10,12 tetradecapentaenamide, (2E,4E,8E,10E,12E)-N-(2-methylpropyl) -2,4,8,10,12-tetradecapentaenamide, (2E,4E,8Z,11E)-N-(2-methylpropyl)-2,4,8,11-tetradecatetraenamide, N-(2-methylpropyl)-2,4,8,10-tetradecatetraenamide, 2,4,8,10-tetradecatetraenamide, N-(2-methylpropyl)-, (E,E,Z,Z)-, (2E,6E,8E,10E)-N-(2,3-dihydroxy-2-methylpropyl)-2,6,8,10-dodecatetraenamide, (2E,7E,9E)-11-hydroxy-N-(2-methylpropyl)-6-oxo-2,7,9-dodecatrienamide, 2,7,9-dodecatrienamide, 6-hydroxy-N-(2-methylpropyl)-11-oxo-, (2E,7E,9E)-, 2,7,9-dodecatrienamide, 6,11-dihydroxy-N-(2-methylpropyl)-, (2E,7E,9E)-, (2E,4E,10E)-8,9-dihydroxy-N-(2-methylpropyl)-2,4,10-dodecatrienamide, (2E,4E,10Z)-8,9- Dihydroxy-N-(2-methylpropyl)-2,4,10-dodecatrienamide; 2,4,8,10,12-pentadecapentaenamide; N-(2-methylpropyl)-, (2E,4E,8E,10Z,12E)-, (2E,4E,8Z)-N-(2-methylpropyl)-12-oxo-2,4,8-tetradecatrienamide; 2,4,8,11-tetradecatetraenamide; N-(2-hydroxy-2-methylpropyl)-, (E,E,Z,E)-, dihydrobungeanool; (2E,4E)-N-(2-methylpropyl)- (2E,7E,9E)-6-hydroxy-N-(2-hydroxy-2-methylpropyl)-11-oxo-2,7,9-dodecatrienamide, (2E,7E,9E)-11-hydroxy-N-(2-hydroxy-2-methylpropyl)-6-oxo-2,7,9-dodecatrienamide, (E)-N-(2-hydroxy-2-methylpropyl)tetradec-2-enamide, 2,4,8,10-tetradecatetraenamide, 12-hydroxy-N-(2-hydroxy ... hydroxy-2-methylpropyl)-, (2E,4E,8Z,10E)-, 2,4,9,11-tetradecatetraenamide, 8,13-dihydroxy-N-(2-methylpropyl)-, (2E,4E,9E,11E)-, (2E,4E,8Z)-N-(2-hydroxy-2-methylpropyl)-12-oxo-2,4,8-tetradecatrienamide, and 2,4,9,11-tetradecatetraenamide, 8-hydroxy-N-(2-hydroxy-2-methylpropyl)-13-oxo, (2E,4E,9E,11E)-.

[0140] Sanshool standards, hydroxy-β-sanshool (S3), hydroxy-γ-sanshool (S2) were purchased from the market. NMR and LCHRMS analyses were used to confirm the structure and purity. Hydroxy-α-sanshool (S1) was isolated from the aqueous ethanol extract.

[0141] Then, 10.744 g of dried extract from Zanthoxylum candida oil using aqueous ethanol extraction was dissolved in 40 mL of ethanol. The solution was then loaded on top of a flash column (80 g, 150 mL, ID 3.12 cm × H. 19.5 cm) packed with MCI gel (Mitsubishi Chemical Corporation, CHP20). After adsorption, desorption was performed in an ethanol / water solvent system by gradually increasing the ratio of ethanol to water. The desorption process started with 20% v / v ethanol, 10 bed volumes, then continued with 60% v / v ethanol, 10 bed volumes, and finally washed with 95% v / v ethanol, 10 bed volumes. The constant flow rate of the mobile phase was 10 mL / min. The fractions were characterized using U(H)LC-HRMS C18 method. The fractions contained high purity hydroxy-α-sanshool (>95%) and were collected and dried. The structure was confirmed by NMR analysis.

[0142] Example 2 - Sensory Analysis A panel of eight experts evaluated the samples for their sensory attributes (sweetness, liquorice, length of sweetness lingering) in addition to the reference at 0.2 or 5 ppm on a scale of -5 to 5 (-5 indicating a strong masking effect, 5 indicating a strong enhancing effect, and 0 being the intensity of the reference aqueous solution containing 4% sucrose or 0.02% SG95). The results are shown in Table 2.

[0143] [Table 2]

[0144] In some embodiments of the present disclosure, the flavor modifying composition provides multiple benefits, for example, the test samples, i.e., Zanthoxylum ketata extract and Sanshool, can significantly increase the sweetness intensity of the solution sweetened with sucrose or stevia extract.All test samples, i.e., Zanthoxylum ketata extract and Sanshool, can significantly mask the lingering taste of stevia extract.

[0145] A panel of eight experts spiked R1 at 50 ppm with various sweeteners and evaluated their sweetness characteristics (0 indicates no sweetness and 10 indicates too sweet). The sweetener doses were designed below the sweetness threshold in water. The results are shown in Table 3.

[0146] [Table 3]

[0147] In some embodiments of the present disclosure, the flavor modifying compositions provide multiple benefits, for example, the tested Zanthoxylum arborescens oil (R1) can significantly enhance the sweetness of compound solutions including solutions of naringenin, eriodictyol, homoeriodictyol, trilobatin, hesperetin dihydrochalcone 4'-O-glucoside, hesperidin dihydrochalcone, neohesperidin dihydrochalcone (NHDC), alpha-mogroside IV (2379350-24-8), mogroside V, rebaudioside A, malonyl rebaudioside A, rebaudioside E, malonyl rebaudioside E, and rubusoside.

Claims

1. 1. Use of a flavor altering composition to enhance the sweetness of an ingestible composition, said flavor altering composition comprising one or more compounds of formula I: 【Chemistry 1】 or a salt thereof, R １ But -CH ２ -CH(CH ３ ) ２ , -CH ２ -C(OH)(CH ３ ) ２ , -CH ２ -C(=CH ２ )-CH ３ , -CH=C(CH ３ ) ２ , or -CH ２ -C(OH)(CH ２ OH)(CH ３ ) and R ２ But C ９ Alkyl, C １１ Alkyl, C ９ alkenyl, or C １１ alkenyl, each of which is optionally substituted one or more times with a hydroxy group, an oxo group, or a combination thereof.

2. R １ Ga-CH ２ -CH(CH ３ ) ２ The use according to claim 1, wherein

3. R １ Ga-CH ２ -C(=CH ２ )-CH ３ The use according to claim 1, wherein

4. R １ Ga-CH ２ -C(OH)(CH ２ OH)(CH ３ 2. The use according to claim 1, wherein

5. R １ Ga-CH ２ -C(OH)(CH ３ ) ２ The use according to claim 1, wherein

6. R ２ is optionally substituted one or more times with a hydroxy group, an oxo group, or a combination thereof; ９ The use according to claim 1, wherein the alkyl is alkyl.

7. R ２ is optionally substituted one or more times with a hydroxy group, an oxo group, or a combination thereof; ９ The use according to claim 1, wherein the alkyl group is alkenyl.

8. R ２ is optionally substituted one or more times with a hydroxy group, an oxo group, or a combination thereof; １１ The use according to claim 1, wherein the alkyl is alkyl.

9. R ２ is optionally substituted one or more times with a hydroxy group, an oxo group, or a combination thereof; １１ The use according to claim 1, wherein the alkyl group is alkenyl.

10. 2. The use according to claim 1, wherein the taste-altering composition comprises one or more compounds selected from the group consisting of compounds 1 to 41, or a edible acceptable salt thereof.

11. 2. The use according to claim 1, wherein the flavor-altering composition comprises hydroxy-α-sanshool.

12. 2. The use according to claim 1, wherein the flavor-altering composition comprises hydroxy-β-sanshool.

13. 2. The use according to claim 1, wherein the flavor-altering composition comprises hydroxy-γ-sanshool.

14. 2. The use of claim 1, wherein the flavor-altering composition comprises an extract of Zanthoxylum chinense oil.

15. 15. The use of claim 14, wherein the extract is obtained by an extraction method comprising contacting Zanthoxylum chinense oil with an extraction medium, wherein the extraction medium comprises water, a water-miscible solvent, or a combination thereof.

16. 16. The use according to claim 15, wherein the extraction medium comprises water and ethanol.

17. The use of claim 1 , wherein the ingestible composition comprises a sweetener.

18. 18. The use of claim 17, wherein the sweetener is naringenin, eriodictyol, homoeriodictyol, trilobatin, hesperetin dihydrochalcone, hesperetin dihydrochalcone-4'-O-glucoside, neohesperidin dihydrochalcone, α-mogroside IV, mogroside V, rebaudioside A, malonylebaudioside A, malonylebaudioside E, rebaudioside E, rebaudioside M, rubusoside, or any combination thereof.

19. The sweetener may be a high-intensity sweetener, such as acesulfame potassium, aspartame, neotame, cyclamate, saccharin, sucralose, steviol glycosides (e.g., rebaudioside A, rebaudioside B, rebaudioside M, rebaudioside D, or rebaudioside E), or a mogroside (e.g., mogroside III, mogroside IV, mogroside V, siamenoside I, isomogroside V, mogroside IV, Ｅ , Isomogroside IV, Mogroside III Ｅ 18. The use of claim 17, wherein the 1,6-α isomer of 11-oxomogroside V, or siamenoside I, or any combination thereof, is used.

20. 18. The use according to claim 17, wherein the concentration of the sweetener is below the sweetness threshold.

21. 10. The use of claim 1, wherein the concentration of sanshool compound used in the ingestible composition is in the range of 0.001 ppm to 1000 ppm.

22. 1. A method of enhancing the sweetness of an ingestible composition, comprising introducing a flavor-altering composition into said ingestible composition, said flavor-altering composition comprising one or more of Formula I: 【Chemistry 2】 or a salt thereof, R １ But -CH ２ -CH(CH ３ ) ２ , -CH ２ -C(OH)(CH ３ ) ２ , -CH ２ -C(=CH ２ )-CH ３ , -CH=C(CH ３ ) ２ , or -CH ２ -C(OH)(CH ２ OH)(CH ３ ) and R ２ But C ９ Alkyl, C １１ Alkyl, C ９ alkenyl, or C １１ alkenyl, each of which is optionally substituted one or more times with a hydroxy group, an oxo group, or a combination thereof.

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