CN119031856A - Fatty acid amides and their use as flavor modifiers - Google Patents

Abstract

The present disclosure relates generally to certain fatty acid amide compounds, such as hydroxy-alpha-sanshool, hydroxy-beta-sanshool, and hydroxy-gamma-sanshool, and the use of such compounds to impart or enhance sweetness, as well as to mask bitter, enhance mouthfeel, or mask astringency. In certain embodiments, such compounds are used in combination with other sweeteners or sweetness enhancers (e.g., flavonoids or dihydrochalcones). In certain aspects, the present disclosure provides ingestible compositions comprising such fatty acid amides. In some related aspects, the ingestible composition is or is included in a variety of flavored products, such as food products, beverage products, pharmaceutical products, or oral care products.

Description

Fatty acid amides and their use as flavor modifiers

Technical Field

The present disclosure generally relates to certain fatty acid amide compounds, such as hydroxyl-α-sanshools, hydroxyl-β-sanshools and hydroxyl-γ-sanshools, and such compounds are used to impart or enhance sweetness, and mask bitterness, enhance mouthfeel or mask the purposes of astringency. In certain embodiments, such compounds are used in combination with other sweeteners or sweetness enhancers (such as flavonoids or dihydrochalcone). In some forms, the present disclosure provides an ingestible composition comprising such fatty acid amide. In some related forms, the ingestible composition is various flavored (flavored, flavored) products or is included in various flavored products, such as food products, beverage products, pharmaceutical products or oral care products.

Background Art

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

Sweetness is the taste most often experienced when consuming foods that are high in sugar. Mammals generally perceive sweetness as a pleasant sensation, except in excess. Caloric sweeteners, such as sucrose and fructose, are classic examples of sweetening substances. Despite the existence of a variety of non-caloric and low-calorie alternatives, these caloric sweeteners remain the primary means of eliciting the perception of sweetness in edible products when consumed.

Metabolic disorders and related diseases, such as obesity, diabetes, and cardiovascular disease, are major public health issues worldwide. Their prevalence is growing at an alarming rate in almost every developed country. Caloric sweeteners are a key factor in this trend, as they have been included in a variety of packaged food and beverage products to make them more palatable to consumers. In many cases, non-caloric or low-calorie alternatives can be used in place of sucrose or fructose in food and beverages. Even so, the sweetness imparted by these compounds is different from that of caloric sweeteners, and many consumers fail to consider them as suitable substitutes. Moreover, such compounds can be difficult to incorporate into certain products. In some cases, they can be used as partial substitutes for caloric sweeteners, but their presence itself causes many consumers to perceive unpleasant off-flavors, including astringency, bitterness, metallic taste, and licorice. Therefore, low-calorie sweeteners face certain challenges in their adoption.

Sweet taste enhancement provides an alternative method to overcome some of the challenges of adoption faced by low-calorie sweeteners. Such compounds can be used in combination with sucrose or fructose to enhance their sweetness, thereby allowing the use of lower amounts of such caloric sweeteners in various food or beverage products. However, in addition to enhancing the perceived sweetness of the primary sweetener, such compounds still change the perceived taste of the sweetener. Therefore, many consumers find that it is more unpleasant to eat such products of sweet taste enhancement than unenhanced substitutes with higher calories. Therefore, there is a continuous need to find a class of compounds that can improve the sweetness of caloric sweeteners without changing their perceived taste in a way that impairs the pleasure experienced by consumers when eating or drinking products containing such sweeteners.

Summary of the invention

The present disclosure relates to the discovery that certain fatty acid amides can impart or enhance sweetness in a more natural tasting manner, and in some cases can also be used to mask bitterness, enhance mouthfeel, or mask astringency.

In a first aspect, the present disclosure provides a flavor-modifying compound, which is a compound of formula (I):

or a salt thereof, wherein:

R ¹ is -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 ) ₂ ; and

^R2 is _C9 alkyl, _C11 alkyl, _C9 alkenyl or _C11 alkenyl, each of which is optionally substituted one or more times with hydroxy, oxo or a combination thereof.

In a second aspect, the present disclosure provides a flavor modification composition comprising one or more flavor modification compounds of the first aspect. In some embodiments, the flavor modification composition is a composition obtained from Sichuan pepper oil. In some embodiments, the flavor modification composition is a composition obtained from extracting Sichuan pepper oil using an aqueous or water-miscible solvent system.

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 an 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.

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

In a fifth aspect, the present disclosure provides the use of a flavor-modifying compound of a first aspect or a flavor-modifying composition of a 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, the method comprising introducing a flavor-modifying compound of a first aspect or a flavor-modifying composition of a second aspect into an 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 licorice aftertaste of certain high-intensity sweeteners (e.g., high-intensity sweeteners based on stevia). In some embodiments, the ingestible composition comprises one or more flavonoids or dihydrochalcones.

In a sixth aspect, the present disclosure provides a use of a flavor-modifying compound of the first aspect or a flavor-modifying composition of the second aspect for enhancing the mouthfeel of an ingestible composition. In certain related aspects, the present disclosure provides a method for enhancing the mouthfeel of an ingestible composition, the method 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 flavonoids or dihydrochalcones.

In a seventh aspect, the present disclosure provides an ingestible composition comprising one or more 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 dihydrochalcone. In some embodiments, the ingestible composition comprises one or more bitter taste enhancers.

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.

Further aspects and embodiments thereof are set forth in the following detailed description, drawings, abstract and claims.

BRIEF DESCRIPTION OF THE DRAWINGS

The following figures are provided to illustrate various embodiments of the compositions and methods disclosed herein. The figures are provided for illustration purposes only and are not intended to describe any preferred compositions or preferred methods, nor as a source of any limitation on the scope of the claimed invention.

Figure 1 shows chemical formulas representing flavor-modifying compounds 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 _C9 alkyl, _C11 alkyl, _C9 alkenyl, or _C11 alkenyl, each of which is optionally substituted one or more times with hydroxy, oxo _, or a combination thereof.

DETAILED DESCRIPTION

The following detailed description sets forth various configurations and embodiments provided herein. This description will be read from the perspective of a person of ordinary skill in the relevant art. Therefore, information known to these persons of ordinary skill is not necessarily included.

definition

Unless otherwise provided herein, the following terms and phrases have the meanings indicated below. The present disclosure may employ other terms and phrases not expressly defined herein. Such other terms and phrases have the meanings they have in the context of the present disclosure for those of ordinary skill in the art. In some cases, a term or phrase may be defined in the singular or in the plural. In this case, it is to be understood that any term in the singular may include its plural form, and vice versa, unless expressly indicated to the contrary.

"Sweetener" refers to a compound, or an ingestibly acceptable salt thereof, that elicits a detectable sweet taste in a subject, such as a compound that activates T1R2 and T1R3 taste receptors in vivo or in vitro.

"Bitter tastant" refers to a compound, or an ingestibly acceptable salt thereof, that elicits a detectable bitter taste in a subject, such as a compound that activates one or more T2R taste receptors in vivo or in vitro.

As used herein, "C _a to C _b " or "C _ab ", where "a" and "b" are integers, refers to the number of carbon atoms in the specified group. That is, the group can contain from "a" to "b" (including the end values) carbon atoms. Thus, for example, "C ₁ to C ₄ alkyl" or "C _1-4 alkyl" refers to all alkyl groups having 1 to 4 carbons, i.e., CH ₃ -, CH ₃ CH ₂ -, CH ₃ CH ₂ CH ₂ -, (CH ₃ ) ₂ CH-, CH ₃ CH ₂ CH ₂ CH ₂ -, CH ₃ CH ₂ CH(CH ₃ )-, and (CH ₃ ) ₃ C-.

As used herein, "alkyl" refers to a fully saturated straight or branched hydrocarbon chain (i.e., not containing double or triple bonds). In some embodiments, the alkyl group has 1 to 20 carbon atoms (whenever it appears in this article, a numerical range such as "1 to 20" refers to each integer in the given range; for example, "1 to 20 carbon atoms" means that the alkyl group can be composed of 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc., up to and including 20 carbon atoms, although the present definition also covers the occurrence of the term "alkyl" in which no numerical range is specified). The alkyl group can also be a medium-sized alkyl group with 1 to 9 carbon atoms. The alkyl group can also be a low alkyl group with 1 to 4 carbon atoms. The alkyl group can be referred to as "C _1-4 alkyl" or similar names. By way of example only, "C _1-4 alkyl" means that there are 1 to 4 carbon atoms in the alkyl chain, that is, the alkyl chain is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl. Typical alkyl groups include, but are in no way limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, etc. Unless otherwise indicated, the term "alkyl" refers to a group that is not further substituted.

As used herein, "alkenyl" refers to a straight or branched hydrocarbon chain containing one or more double bonds. In some embodiments, the alkenyl group has 2 to 20 carbon atoms, although the definition also encompasses the occurrence of the term "alkenyl" in which no numerical range is specified. The alkenyl group may also be a medium-sized alkenyl group having 2 to 9 carbon atoms. The alkenyl group may also be a low-order alkenyl group having 2 to 4 carbon atoms. The alkenyl group may be referred to as " _C2-4 alkenyl" or similar names. By way of example only, " _C2-4 alkenyl" means 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. Typical alkenyl groups include, but are by no means limited to, ethenyl, propenyl, butenyl, pentenyl, and hexenyl, among others. Unless otherwise indicated, the term "alkenyl" refers to a group that is not further substituted.

As used herein, "hydroxyl" or "hydroxyl group" refers to an -OH substituent.

As used herein, "oxo" refers to a =0 substituent.

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

As used herein, "for example," "such as," "such as," or "including" are intended to introduce examples that further illustrate a more general subject matter. Unless otherwise expressly noted, such examples are provided merely to aid in understanding the embodiments shown in the present disclosure and are not meant to be limiting in any way. These phrases also do not indicate any kind of preference for the disclosed embodiments.

As used herein, "include," "comprising," "containing," and "comprised of" refer to an open group, meaning that the group may include other members in addition to those explicitly stated. For example, the phrase "comprising A" means that A must be present, but other members may also be present. The terms "including," "having," and "composed of" and their grammatical variants have the same meaning. In contrast, "consist of" or "composed of" or "composed of" refer to a closed group. For example, the phrase "consisting of A" means that only A is present.

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 does occur one or more times.

As used herein, "or" is to be given its broadest reasonable interpretation and is not limited to an "either/or" construction. Thus, the phrase "comprising A or B" means that A may be present and B may not be present, or B may be present and A may not be present, or both A and B may be present. Furthermore, for example, if A defines a class that may have multiple members (e.g., _A1 and _A2 ), then one or more members of the class may be present at the same time.

Chemical structures are often displayed using a "skeleton" format, so that the carbon atoms are not explicitly shown and hydrogen atoms attached to the carbon atoms are omitted entirely. For example, the structure represents butane (i.e., n-butane). In addition, aromatic groups such as benzene are represented by showing a contributing resonance structure. For example, the structure Represents toluene.

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, as well as any embodiment described herein. The term "flavor-modifying composition" refers to a composition comprising one or more such flavor-modifying compounds, such as a composition obtained by extracting Zanthoxylum bungeanum oil with an aqueous or water-miscible solvent system.

Other terms are defined in other parts of this specification even if not included in this section.

Flavour-modifying compounds and flavour-modifying compositions

In certain aspects, the present disclosure provides a flavor-modifying compound, which is a compound of formula (I):

or a salt thereof, wherein:

R ¹ is -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 ) ₂ ; and

^R2 is _C9 alkyl, _C11 alkyl, _C9 alkenyl or _C11 alkenyl, each of which is optionally substituted one or more times with hydroxy, oxo or a combination thereof.

The variable R ¹ may have any suitable value according to the above definition. In some embodiments, R ¹ is -CH ₂ -CH(CH ₃ ) ₂ . In some embodiments, R ¹ is -CH ₂ -C(OH)(CH ₃ ) ₂ . In some embodiments, R ¹ is -CH ₂ -C(═CH ₂ )-CH ₃ . In some embodiments, R ¹ is -CH═C(CH ₃ ) ₂ . In some embodiments, R ¹ is -CH ₂ -C(OH)(CH ₂ OH)(CH ₃ ), wherein the β-position carbon atom is in the R or S stereochemical configuration. In some such embodiments, the β-position carbon atom is in the R stereochemical configuration. In some other such embodiments, the β-position carbon atom is in the S stereochemical configuration.

The variable ^R2 may have any suitable value according to the above definition. In some embodiments of any of the foregoing embodiments, ^R2 is _C9 alkyl, which is optionally substituted one or more times by hydroxyl, oxo, or a combination thereof. In some embodiments, ^R2 is a straight chain _C9 alkyl (nonyl), which is optionally substituted one or two times by hydroxyl, oxo, or a combination thereof. In some embodiments, ^R2 is nonyl.

In certain embodiments of any of the foregoing embodiments, ^R is C ₁₁ alkyl, which is optionally substituted once or twice with hydroxyl, oxo, or a combination thereof. In some embodiments, ^R is straight chain C ₁₁ alkyl (undecyl), which is optionally substituted once or multiple times with hydroxyl, oxo, or a combination thereof. In some embodiments, ^R is undecyl.

In some embodiments of any of the foregoing embodiments, ^R is _C9 alkenyl, which is optionally substituted one or more times by hydroxyl, oxo, or a combination thereof. In some embodiments, ^R is a straight chain _C9 alkenyl, which is optionally substituted one or two times by hydroxyl, oxo, or a combination thereof. In some embodiments, ^R is an unsubstituted straight chain _C9 alkenyl having one to four carbon-carbon double bonds. In some embodiments, ^R is a straight chain _C9 alkenyl having one to four carbon-carbon double bonds, which is substituted one or two times by a substituent selected from hydroxyl, oxo, or a combination thereof.

In certain embodiments of any of the foregoing embodiments, ^R is C ₁₁ alkenyl, which is optionally substituted one or more times by hydroxyl, oxo, or a combination thereof. In some embodiments, ^R is a straight chain C ₁₁ alkenyl, which is optionally substituted one or two times by hydroxyl, oxo, or a combination thereof. In some embodiments, ^R is an unsubstituted straight chain C ₁₁ alkenyl having one to four carbon-carbon double bonds. In some embodiments, ^R is a straight chain C ₁₁ alkenyl having one to four carbon-carbon double bonds, which is substituted one or two times by a substituent selected from hydroxyl, oxo, or a combination thereof.

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

Table 1

When the flavor-modifying compounds disclosed herein have at least one chiral center, they may exist as individual enantiomers and diastereomers or as mixtures of such isomers. In some embodiments related to the second aspect, the sweet taste enhancing compound has substantial enantiomeric purity.

The separation of each isomer or the selective synthesis of each isomer is completed by applying various methods well known to those skilled in the art. Unless otherwise stated (for example, in the case of clearly showing the stereochemistry of the chiral center), all such isomers and mixtures thereof are included in the scope of the compounds disclosed herein. In addition, the compounds disclosed herein may exist in one or more crystalline or amorphous forms. Unless otherwise stated, all these forms are included in the scope of the compounds disclosed herein, including any polymorphic form. In addition, some compounds disclosed herein can form solvates with water (i.e., hydrates) or common organic solvents. Unless otherwise stated, these solvates are included in the scope of the compounds disclosed herein.

Those skilled in the art will recognize that some of the structures described herein may be resonance forms or tautomers of compounds that can be reasonably represented by other chemical structures, even kinetically; the skilled artisan recognizes that such structures may represent only a small fraction of such compound samples. Such compounds are considered to be within the scope of the structures shown, even though such resonance forms or tautomers are not shown herein.

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

In some embodiments, the flavor modification compounds disclosed herein are capable of forming acidic and/or basic salts due to the presence of amino and/or carboxyl groups or groups similar thereto. Edible 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. Edible 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; ammonium, potassium, sodium, calcium, and magnesium salts are particularly preferred. In some embodiments, treatment of the compounds disclosed herein with an inorganic base results in the compound losing unstable hydrogen, thereby obtaining a salt form containing inorganic cations such as Li ⁺ , Na ⁺ , K ⁺ , Mg ²⁺ and Ca ²⁺ , etc. 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, etc., particularly 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.

In certain forms, the present disclosure provides a flavor modification composition comprising one or more flavor modification compounds selected from the group consisting of compounds 1 to 41, and edible acceptable salts thereof. Many of these compounds are present in certain pepper varieties, such as Sichuan pepper or Szechuan pepper.

Thus, in some embodiments, the flavor-modifying composition is a composition obtained from Zanthoxylum bungeanum oil.In some embodiments, Zanthoxylum bungeanum or Sichuan pepper includes, but is not limited to, ingredient FEMA 4754 or ingredient N342 in GB2760 or ingredient EC/Listno.:306-820-8 or ingredient CAS 97404-53-0.

Thus, in some embodiments, the flavor-modifying composition is a composition obtained by extracting Zanthoxylum bungeanum oil using an aqueous or water-miscible solvent system (eg, a water/ethanol solvent system or a pure ethanol solvent system).

Uses and methods

In certain aspects, the present disclosure provides the use of the above-described flavor-modifying compounds or flavor-modifying compositions 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 the above-described flavor-modifying compounds or flavor-modifying compositions into an ingestible composition.

In certain aspects, the present disclosure provides a use of the above-described flavor-modifying compound or flavor-modifying composition for reducing the bitterness of an ingestible composition. In certain related aspects, the present disclosure provides a method for reducing the bitterness of an ingestible composition, the method comprising introducing the above-described flavor-modifying compound or flavor-modifying composition into the ingestible composition.

In certain aspects, the present disclosure provides the use of the above-described flavor-modifying compounds or flavor-modifying compositions for reducing the astringency of an ingestible composition (e.g., the lingering aftertaste of a high-intensity sweetener or a licorice aftertaste). In certain related aspects, the present disclosure provides a method of reducing the astringency of an ingestible composition, the method comprising introducing the above-described flavor-modifying compounds or flavor-modifying compositions into the ingestible composition.

In certain aspects, the present disclosure provides the use of the above-mentioned flavor-modifying compound or flavor-modifying composition for enhancing the mouthfeel of an ingestible composition. In certain related aspects, the present disclosure provides a method for enhancing the mouthfeel of an ingestible composition, the method comprising introducing the above-mentioned flavor-modifying compound or flavor-modifying composition into the ingestible composition.

The aforementioned uses and methods relate to ingestible compositions.In addition to those ingestible composition features set forth above, the ingestible composition may also comprise any feature or combination of features set forth below.

Ingestible composition

In certain aspects, the present disclosure provides an ingestible composition comprising a flavor-modifying compound or a flavor-modifying composition according to the above embodiments. When introduced into or used in an ingestible composition, the flavor-modifying compound is used or introduced into the ingestible composition at a concentration ranging from 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.

In some embodiments, the ingestible composition comprises one or more bitter taste agents. In some embodiments, the bitter taste agent is a high intensity sweetener, such as acesulfame potassium, aspartame, neotame, cyclamates, saccharin, sucralose, steviol glycosides (e.g., rebaudioside A, rebaudioside B, rebaudioside M, rebaudioside D, or rebaudioside E), and mogrosides (e.g., mogroside III, mogroside IV, mogroside V, simonoside I, isomogroside V, mogroside IV _E , isomogroside IV, mogroside III _E , 11-oxomogroside V, or 1,6-α isomer of simonoside I). Therefore, the flavor-modifying compound may be suitable for use in low-sugar or zero-sugar products to reduce the bitterness imparted by low-calorie or zero-calorie sweeteners.

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

In some embodiments, the bitter taste agent is a non-animal protein, such as a plant protein, an algae protein, or a fungal protein. In some embodiments, the ingestible composition comprises a plant protein. Non-limiting examples of plant proteins include pea protein, soy protein, almond protein, cashew protein, canola (canola) (rapeseed) protein, chickpea protein, broad bean protein, sunflower protein, wheat protein, oat protein, barley protein, and potato protein. Such non-animal proteins are commonly used as partial or complete substitutes for animal proteins in dairy analogs and meat analogs. Therefore, flavor-modifying compounds may be suitable for use 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 tonality and green tonality experienced by consumers.

In some embodiments, the bitter tastants are caffeine, quinine, green tea, catechins, polyphenols (e.g., polyphenol antioxidants), tannins, robusta green coffee bean extract, green coffee bean extract, menthol, etc. Such compounds are commonly found in various natural food products such as tea and coffee, as well as packaged food products such as instant tea, instant coffee, packaged beverages, etc. When one or more such bitter tastants are present, the flavor modifying compounds are suitable for blocking the bitter taste of such compounds and improving the perceived taste of the product by the consumer.

In some embodiments, the bitter tastant is a drug compound. Non-limiting examples of drug compounds with a bitter taste include atropine, brinzolamide, chloramphenicol, chloroquine, clindamycin, dexamethasone, digoxin, diltiazem, diphenhydramine, docusate, dorzolamide, doxepin, doxylamine, enalapril, erythromycin, esomeprazole, famotidine, gabapentin, ginkgolide A, phenoxyethanol, quinolinol ... A), guaifenesin, L-histidine, lomefloxacin, methylprednisolone, ofloxacin, oleuropein, oxyphenonium, pirenzepine, prednisone, ranitidine, trapidil, trimethoprim and cetirizine. When one or more of these pharmaceutical compounds are used in oral pharmaceutical preparations, the flavor-modifying compounds are suitable for blocking the bitter taste of these compounds and improving the perceived taste of the pharmaceutical product by consumers.

In some embodiments, the bitter taste promoting agent is an oral care ingredient. Many oral care ingredients impart bitterness, and this bitterness must be masked or blocked to improve consumer acceptance of the product. Non-limiting examples of such oral care ingredients include menthol, menthol analogs, peppermint extracts, sodium bicarbonate, alkali metal persulfate (potassium persulfate), cetylpyridinium chloride, lauryl amide propyl 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, flavor modifying compounds are suitable for blocking the bitterness of such compounds and improving the perceived taste of oral care products by consumers.

In some embodiments, the bitter taste enhancer is a bitter taste enhancer found in citrus, such as limonin, nomelin, or naringin. Many citrus-containing formulations impart a bitter off-flavor that must be masked or blocked to increase consumer acceptance of the product. In some cases, this bitter off-flavor may be caused by citrus greening disease, which turns citrus fruits green before they are fully ripe. When one or more of these citrus bittering agents are present in a product, flavor-modifying compounds are suitable for blocking the bitterness of these compounds and improving the perceived taste of the citrus product by consumers.

In some embodiments, the ingestible composition comprises one or more flavonoids, dihydrochalcone or other related compounds. Non-limiting examples of such compounds include hesperidin dihydrochalcone, hesperidin dihydrochalcone-4'-O'glucoside, neohesperidin dihydrochalcone, brazzein, hesperidin, phytosterol, naringenin, naringin, phloretin, glucosylated steviol glycosides, (2R, 3R)-3-acetoxy-5,7,4'-trihydroxyflavanone, (2R, 3R)-3-acetoxy-5,7,3'-trihydroxy-4'-methoxyflavanone, sweet leaf glycoside, thaumatin, monellin, miraculin, glycyrrhizin and and their edible acceptable salts (e.g., monoammonium salts), naringin dihydrochalcone, myricetin, nobiletin, polymethoxyflavonoids, mixed methoxy and hydroxyflavonoids, quercetin, amino acids, eriodictyol, homoeriodictyol, trilobatin, phlorizin, monellin, malonyl steviol glycosides, malonyl mogroside, malonyl sweet leaf rubusoside, eriodictyol-6-glucoside, glucosylated steviol glycosides (GSG), glucosylated mogrosides, and glucosylated sweet leaf rubusoside. As used herein, the terms "glucosylated steviol glycosides" and "glucosylated mogrosides" and "glucosylated sweet leaf rubusoside" refer to products obtained by enzymatic glucosylation of natural steviol glycoside compounds, mogroside compounds, or sweet leaf rubusoside compounds. Glucosylation typically occurs via glycosidic bonds, such as α-1,2 bonds, α-1,4 bonds, α-1,6 bonds, β-1,2 bonds, β-1,4 bonds, β-1,6 bonds, etc. Any of the above compounds may be present in the ingestible composition in combination with the flavor-modifying compounds disclosed herein at any suitable concentration, such as a concentration ranging from 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.

In some embodiments, the ingestible composition comprises a combination of sweetener or multiple sweeteners. In some embodiments, sweetener is a common sugar sweetener, such as sucrose, fructose, glucose, and 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 vegetable sources. In some embodiments, sweetener is sucrose, fructose or a combination thereof. In some embodiments, sweetener is sucrose. In some other embodiments, sweetener is selected from rare natural sugars, including D-allose, D-psicose, L-ribose, D-tagatose, L-glucose, L-fucose, L-arabinose, D-turanose and D-white bacteria disaccharide. In some embodiments, sweetener is selected from semi-synthetic "sugar alcohol" sweetener, such as erythritol, isomalt, lactitol, mannitol, sorbitol, xylitol, maltodextrin etc. In some embodiments, the sweetener is selected from artificial sweeteners, such as aspartame, saccharin, acesulfame potassium, cyclamates, sucralose and alitame. In some embodiments, the sweetener is selected from the group consisting of cyclamic acid, mogroside, tagatose, maltose, galactose, mannose, sucrose, fructose, lactose, allulose, neotame and other aspartame derivatives, glucose, D-tryptophan, glycine, maltitol, lactitol, isomalt, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolysate (HSH), stevioside, rebaudioside A, other sweet steviosides, chemically modified steviol glycosides (such as glucosylated steviol glycosides), other mogrosides, chemically modified mogrosides (such as glucosylated mogrosides), guanidine sweeteners (carrelame) and other guanidine sweeteners. In some embodiments, sweetener is a combination of two or more sweeteners set forth in this paragraph. In some embodiments, sweetener can be a combination of two, three, four or five sweeteners disclosed herein. In some embodiments, sweetener can be sugar. In some embodiments, sweetener can be a combination of one or more sugars and other natural and artificial sweeteners. In some embodiments, sweetener is sugar. In some embodiments, sugar is cane sugar. In some embodiments, sugar is beet sugar. In some embodiments, sugar can be sucrose, fructose, glucose or a combination thereof. In some embodiments, sugar can be sucrose. In some embodiments, sugar can be a combination of fructose and glucose.

Sweeteners can also include, for example, sweetener compositions comprising one or more natural or synthetic carbohydrates such as corn syrup, high fructose corn syrup, high maltose corn syrup, glucose syrup, sucralose syrup, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolysate (HSH), or other syrups or sweetener concentrates from natural fruit and vegetable sources, or semi-synthetic "sugar alcohol" sweeteners, such as polyols. In some embodiments, non-limiting examples of polyols include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerine), threitol, galactitol, palatinose, reduced isomaltooligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, reduced glucose syrup, isomaltulose, maltodextrin, etc., as well as sugar alcohols or any other carbohydrates or combinations thereof that can be reduced without adversely affecting the taste.

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 known as inulin fiber, fructooligosaccharides or oligofructose), green stevia powder, stevia rebaudiana, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M and other steviol-based glycosides, stevioside, stevioside extract, honey, Jerusalem artichoke, artichoke syrup, licorice root, monk fruit (fruit, powder or extract), lucuma (fruit, powder or extract), maple sap (including, for example, sap extracted from sugar maple (Acer saccharum), black maple (Acer nigrum), American red maple (Acer rubrum), silver maple (Acersaccharinum), Norway maple (Acer platanoides), ash maple (Acer negundo), bigleaf maple (Acer macrophyllum), roughtooth maple (Acer grandidentatum), Rocky Mountain maple (Acer glabrum), monochromatic maple (Acer mono), maple syrup, maple sugar, walnut sap (including, for example, sap extracted from white walnut (Juglans cinerea), black walnut (Juglans nigra), ghost walnut (Juglans ailatifolia), walnut (Juglans regia), birch sap (including, for example, sap extracted from paper birch (Betula papyrifera, yellow birch (Betula alleghaniensis), mountain birch (Betula lenta), river birch (Betula nigra), gray birch (Betula populifolia), weeping birch (Betula pendula), sycamore sap (e.g., sap extracted from Platanus occidentalis), ironwood sap (e.g., sap extracted from Ostrya virginiana), unrefined cane sugar (mascobado), molasses (e.g., blackstrap molasses), molasses sugar, monatin, monellin, cane sugar (e.g., sugar (also known as natural sugar, unrefined sucrose or table sugar), palm sugar, panocha, piloncillo, rapadura, raw sugar, rice syrup, sorghum, sorghum syrup, tapioca syrup (also known as tapioca syrup), thaumatin, yacon root, malt syrup, barley malt syrup, barley malt powder, beet sugar, cane sugar (cane sugar) sugar), crystallized fruit juice crystals, caramel, carbitol, carob syrup, castor sugar, hydrogenated starch hydrolates, hydrolyzed canned fruit juices, hydrolyzed starch, invert sugar, anethole, arabinogalactan, concentrated grape juice (arrope), syrup, P-4000, acesulfame potassium (also known as acesulfame potassium or ace-K), alitame (also known as aclame), advantame, aspartame, baiyunosdie, neotame, benzamide derivatives, bernadame, canderel, guanidine sweeteners (carrelame) and other guanidine sweeteners, plant fiber, corn sugar, coupling sugar, curculin, cyclamates, cyclocaryoside I ( I), demerara, dextran, dextrin, diastatic malt, dulcin, sucrol, valzin, dulcoside A, dulcoside B, emulin, enoxolone, maltodextrin, saccharin, estragole, ethyl maltol, glucin, gluconic acid, gluconic acid lactone, glucosamine, glucuronic acid, glycerol, glycine, glycyphillin, glycyrrhizin, glycyrrhetinic acid monoglucuronide, golden sugar, brown sugar, golden syrup, granulated sugar, gynostemma pentaphyllum, hernandulcin, isomerized liquid sugar, jallab, chicory root dietary fiber, kynurenine derivatives (including N '-formyl-kynurenine, N'-acetyl-kynurenine, 6-chloro-kynurenine), galactitol, litesse, ligicane, lycasin, N-(4-cyanophenyl)-N-(2,3-methylenedioxybenzyl)guanidineacetic acid (lugduname), guanidine, falernum, mabinin I, mabinin II, maltol, crystalline maltitol (maltisorb), maltodextrin, maltotriol, mannosamine, micraculin, mizuame, mogrosides (including, for example, mogroside IV, mogroside V and neomogroside), mukurozioside, nanosaccharide (nano sugar), naringin dihydrochalcone, neohesperidin dihydrochalcone, nib sugar, nib oligosaccharide, norbu, almond syrup, osladin, pekmez, pentadin, periandrin I, perillaldehyde, perillartine, petphyllum, phenylalanine, phloisosideside I, phloretin, phlorodizin, phyllodulcin, polyglycitol syrup, polypodoside A, pterocaryoside A, pterocaryoside B, rebiana, refined syrup, rub syrup, rubusoside, selligueain A), shugr, simonoside I, siraitia grosvenorii, soy oligosaccharides, Splenda, SRIoxime V, steviol glycosides, steviol biosides, steviosides, strogins 1, 2 and 4, sucrose, sucronic acid, sucrononate, sugar, sodium p-nitrophenylureidopropionate (suosan), phloridzin, super aspartame, tetrasaccharide, threitol, treacle, trilobatin, tryptophan and derivatives (6-trifluoromethyl-tryptophan, 6-chloro-D-tryptophan), vanilla sugar, heptyl heptol, birch syrup, aspartame-acesulfame, assugrin, and combinations or blends of any two or more thereof.

Other sweeteners also include any two or more combinations 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 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 a combination thereof. In some embodiments, the ingestible composition may be free of (or in some embodiments, substantially free of) stevia-derived sweeteners, such as steviol glycosides, glucosylated steviol glycosides or rebaudioside.

In some embodiments, the ingestible composition comprises a sour taste enhancer, such as an organic acid. Non-limiting examples of such organic acids include acetic acid, malonic acid, citric acid, lactic acid, and the like.

In certain embodiments, the ingestible compositions may include any additional ingredients or combinations 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 bisulfate, lactic acid, or tartaric acid;

bitter ingredients, including, for example, caffeine, quinine, green tea, catechins, polyphenols, robusta green coffee bean extract, green coffee bean extract, potassium chloride, menthol, or proteins (e.g., proteins and protein isolates from plants, algae, or fungi);

Coloring agents, including, for example, caramel, red #40, yellow #5, yellow #6, blue #1, red #3, purple carrot, black carrot juice, purple sweet potato, vegetable juice, fruit juice, beta-carotene, turmeric curcumin, or titanium dioxide;

preservatives, including, for example, sodium benzoate, potassium benzoate, potassium sorbate, sodium metabisulfite, sorbic acid, or benzoic acid;

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

Vitamins or functional ingredients, including, for example, resveratrol, Co-Q10, omega 3 fatty acids, theanine, choline chloride (Citcoline), inositol, inulin (chicory root), taurine, ginseng extract, guarana extract, ginger extract, L-phenylalanine, L-carnitine, L-tartrate, D-glucuronolactone, inositol, bioflavonoids, echinacea, Ginkgo Biloba, yerba mate, flaxseed oil, Garcinia cambogia peel extract, white tea extract, ribose, milk thistle, thistle extract, grape seed extract, pyridoxine hydrochloride (vitamin B6), cyanocobalamin (vitamin B12), niacinamide (vitamin B3), biotin, calcium lactate, calcium pantothenate (pantothenic acid), calcium phosphate, calcium carbonate, chromium chloride, chromium polynicotinate, cupric sulfate, folic acid, ferric pyrophosphate, iron, magnesium lactate, magnesium carbonate, magnesium sulfate, monopotassium phosphate, monosodium phosphate, phosphorus, potassium iodide, potassium phosphate, riboflavin, sodium sulfate, sodium gluconate, sodium polyphosphate, sodium bicarbonate, thiamine mononitrate, vitamin D3, vitamin A palmitate, zinc gluconate, zinc lactate, or zinc sulfate;

Clouding agents, including, for example, ester gums, brominated vegetable oil (BVO), or sucrose acetate isobutyrate (SAIB);

buffers, including, for example, sodium citrate, potassium citrate, or saline;

Flavors, including, for example, propylene glycol, ethanol, glycerin, gum arabic (acacia), maltodextrin, modified corn starch, dextrose, natural flavorings, natural flavorings with other natural flavorings (natural flavoring WONF), natural and artificial flavorings, artificial flavorings, silicon dioxide, magnesium carbonate, or tricalcium phosphate; or

Starches and stabilizers, including, for example, pectin, xanthan gum, carboxymethyl cellulose (CMC), polysorbate 60, polysorbate 80, medium chain triglycerides, cellulose gel, cellulose gum, sodium caseinate, modified food starch, gum arabic (acacia gum), inulin, or carrageenan.

The ingestible composition may have any suitable pH value. In some embodiments, the amide compound at a wide range of pH values, such as from a lower pH value to a neutral pH value, enhances the sweetness of the sweetener. Lower and neutral pH values include, but are not limited to, 1.5 to 9.0, or 2.5 to 8.5; 3.0 to 8.0; 3.5 to 7.5, and 4.0 to 7 pH values; in certain embodiments, the compounds disclosed and described herein, alone or in combination, can enhance the perceived sweetness of a fixed concentration of sweeteners at low to neutral pH values in a taste test with a compound concentration of 50 μM, 40 μM, 30 μM, 20 μM or 10 μM. In certain embodiments, the enhancement factor of the compounds disclosed and described herein, alone or in combination, at a lower pH is substantially similar to the enhancement factor of the compound at a neutral pH. This consistent sweet taste enhancement property over a wide pH range allows the compounds disclosed and described herein to be widely used in a variety of foods and beverages, alone or in combination.

In some embodiments, the ingestible composition includes flavorings. Any suitable flavoring can be used. In some embodiments, the flavoring includes synthetic flavoring oils and flavoring aromatic substances or oils, oleoresins and extracts from plants, leaves, flowers, fruits, etc., and combinations thereof. Non-limiting examples of flavor oils include spearmint oil, cinnamon oil, sedge oil (methyl salicylate), peppermint oil, Japanese mint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, nutmeg oil, allspice, sage oil, mace, bitter almond oil, and cinnamon oil. Non-limiting examples of other flavors include natural and synthetic fruit flavors, such as vanilla, and citrus oils, including lemon, orange, lime, grapefruit, yazu, sudachi, and fruit essences, including apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, pineapple, watermelon, apricot, banana, melon, apricot, plum, cherry, raspberry, blackberry, tropical fruits, mango, mangosteen, pomegranate, papaya, etc. Other potential flavors include milk flavors, butter flavors, cheese flavors, cream flavors, and yogurt flavors; vanilla flavors; tea or coffee flavors, such as green tea flavors, oolong tea flavors, tea flavors, cocoa flavors, chocolate flavors, and coffee flavors; mint flavors, such as peppermint flavors, spearmint flavors, and Japanese mint flavors; spice flavors, such as asafoetida flavors, ajwain flavors, anise flavors, angelica flavors, fennel flavors, allspice flavors, cinnamon flavors, chamomile flavors, mustard flavors, cardamom flavors, coriander flavors, cumin flavors, clove flavors, pepper flavors, cilantro flavors, sassafras flavors, and cumin flavors. Flavoring agent, salty flavoring agent, Sichuan pepper flavoring agent, basil flavoring agent, juniper berry flavoring agent, ginger flavoring agent, star anise flavoring agent, horseradish flavoring agent, thyme flavoring agent, tarragon flavoring agent, dill flavoring agent, vegetable pepper flavoring agent, nutmeg flavoring agent, basil flavoring agent, marjoram flavoring agent, rosemary flavoring agent, bay leaf flavoring agent and wasabi (Japanese horseradish) flavoring agent; Wine flavoring agent, such as red wine flavoring agent, whiskey flavoring agent, brandy flavoring agent, rum flavoring agent, gin flavoring agent and liqueur flavoring agent; Flower flavoring agent; And vegetable flavoring agent, such as onion flavoring agent, garlic flavoring agent, cabbage flavoring agent, carrot flavoring agent, celery flavoring agent, mushroom flavoring agent and tomato flavoring agent. These flavoring agents can be used in liquid or solid form, and can be used alone or in combination. In dairy or dairy analog products, the most commonly used flavoring agents are agents that impart flavors such as vanilla, French vanilla, chocolate, banana, lemon, hazelnut, coconut, almond, strawberry, mocha, coffee, tea, chai, cinnamon, caramel, cream, brown sugar, toffee, pecan, butter pecan, toffee, Irish cream, white chocolate, raspberry, pumpkin pie spice, spearmint or any combination thereof.

In some embodiments, the ingestible composition comprises vanillin or a vanillin analog that imparts a vanilla flavor to the flavoring agent. In some additional embodiments, the ingestible composition comprises one or more lactones that impart a creamy flavor to the flavoring agent.

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, wherein such an extract is suitable for human consumption. Non-limiting examples of such yeasts include: yeasts of the genus Saccharomyces, such as Saccharomyces cerevisiae or Saccharomyces pastorianus; yeasts of the genus Candida, such as Candida utilis; yeasts of the genus Kluyveromyces, such as Kluyveromyces lactis or Kluyveromyces marxianus; yeasts of the genus Pichia, such as Pichia pastoris; yeasts of the genus Debaryomyces, such as Debaryomyces hansenii; and yeasts of the genus Zygosaccharomyces, 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 is dried after collection (dried yeast).

Such extracts can be produced by any suitable means. In general, yeast extracts or lysates are prepared by extracting the contents of yeast cells from cell wall materials. In many cases, the digestive enzymes in the cells (or other enzymes added to the composition) decompose the proteins and polynucleotides in the yeast into amino acids, oligopeptides (e.g., 2 to 10 peptides), nucleotides, oligonucleotides (2 to 10 nucleotides) and mixtures thereof. Yeast lysates can be prepared by cracking yeast. For example, in some embodiments, the cultured yeast is crushed or cracked by enzymolysis, self-digestion, alkali extraction, hot water extraction, acid decomposition, ultrasonic crushing, homogenizer crushing, freezing and thawing, etc. (two or more of which can be used in combination), thereby obtaining yeast lysates. Yeast can be cultured according to conventional methods. In some embodiments, the cultured yeast is heat treated and then treated with a lysing enzyme to obtain an enzyme lysate. The conditions of the heat treatment are, for example, 80°C to 90°C for 5 to 30 minutes. As a lysing enzyme for enzymolysis, various enzymes can be used as long as the cell wall of the yeast can be cracked. The reaction conditions can be set to be optimal or suitable for the lytic enzyme used, and specific examples thereof may include a temperature of 50 to 60° C. and a pH of 7.0 to 8.0. The reaction time is also not particularly limited, and may be, for example, 3 to 5 hours.

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

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

Examples of suitable synthetic sweetness 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 edible acceptable salt thereof, 3-hydroxybenzoic acid, or any compound listed in U.S. Patent Nos. 8,541,421, 8,815,956, 9,834,544, 8,592,592, 8,877,922, 9,000,054 and 9,000,051, and U.S. Patent Application Publication No. 2017/0119032. Suitable examples of natural sweetness enhancers include, but are not limited to, hesperidin dihydrochalcone, hesperidin dihydrochalcone-4′-O′ glucoside, neohesperidin dihydrochalcone, brazein, hesperidin, phytosterol, 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, monelin, miraculin, glycyrrhizin and their edible acceptable salts (e.g., 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 glycoside" refers to the product of enzymatic glucosylation of natural steviol glycoside compounds. Glucosylation usually occurs through glycosidic bonds, such as α-1,2 bonds, α-1,4 bonds, α-1,6 bonds, β-1,2 bonds, β-1,4 bonds, β-1,6 bonds, etc.

In some embodiments of any of the preceding 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-propionamide, N-(1-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methyl-propan-2-yl)isonicotinamide, or an 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 an 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.

In some embodiments, the ingestible composition comprises one or more umami enhancing compounds. Such umami enhancing compounds include, but are not limited to, compounds of natural origin or synthetic compounds, such as any of the compounds described in U.S. Patent Nos. 8,735,081, 8,124,121, and 8,968,708. In some embodiments, the umami enhancing compound is (2R, 4R)-1,2,4-trihydroxy-17 carbon-16-ene, (2R, 4R)-1,2,4-trihydroxy-17 carbon-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-(heptane-4-yl)benzo-[d][1,3]dioxole-5-carboxamide.

In some other embodiments, the ingestible composition includes one or more cooling enhancing compounds. Such cooling enhancing compounds include, but are not limited to, compounds of natural origin, such as menthol or its analogs, or synthetic compounds, such as any of the compounds described in U.S. Patent Nos. 9,394,287 and 10,421,727. Non-limiting examples include N-ethyl-N-(thiophene-2-ylmethyl)-2-(p-tolyloxy)acetamide, N-(1H-pyrazol-3-yl)-N-(thiophene-2-ylmethyl)-2-(p-tolyloxy)acetamide, 2-(4-fluorophenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophene-2-ylmethyl)acetamide, 2-(2-hydroxy-4-methylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophene-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-(thiophen-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.

In some additional embodiments, the ingestible composition comprises one or more bitter blocking or bitter masking compounds. Such bitter blocking compounds or bitter masking compounds include, but are not limited to, naturally derived compounds or synthetic compounds, such as any of the compounds described in U.S. Pat. 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)-imidazoline-2,4-dione, 4-(2,2,3-trimethylcyclopentyl)butyric acid, 3β-hydroxydihydrocostus lactone, 3β-hydroxypelenolide, probenecid, sakuranetin, 6-methoxysakuranetin, jaceosidin, 4'-fluoro-6-methoxyflavone, 6,3'-dimethoxyflavone, 6-methoxyflavone, γ-aminobutyric acid, Nα,Nα-bis(carboxymethyl)-L-lysine Acid, (+/-) abscisic acid, sodium gluconate, monosodium glutamate, sodium acetate, homoeriodictyol, 7-O-methyleriodictyol (sterubin), eriodictyol, 2,4, dihydrobenzoic acid, neodiosmin, 1-carboxymethyl-5-hydroxy-2-hydroxymethylpyridinium, flavan-3-spiro-C-glycoside, poly-γ-glutamic acid, α,α-trehalose, taurine, (2)-gingerdione, 2,4,-dihydroxybenzoic acid, L-theanine, enterodiol, lariciresinol, enterolactone, matairesinol, and any combination thereof.

In some additional embodiments, the ingestible compositions include one or more sour taste adjusting compounds.

In some additional embodiments, the ingestible composition comprises one or more mouthfeel-modifying compounds. Such mouthfeel-modifying compounds include, but are not limited to, tannins, cellulosic materials, bamboo powder, and the like.

In some other embodiments, the ingestible composition comprises one or more flavor masking compounds. Such flavor masking compounds include, but are not limited to, cellulosic materials, materials extracted from fungi, materials extracted from plants, citric acid, carbonic acid (or carbonates), and the like.

Flavored products

In certain forms, the present disclosure provides a flavored product comprising any of the ingestible compositions of the foregoing forms. 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, dentifrice, whitening agent, etc.

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, juice, fruit-flavored juice, fruit drinks, nectar drinks, vegetable juice, vegetable-flavored juice, sports drinks, energy drinks, fortified water drinks, vitamin-fortified water, near water drinks, coconut water, tea drinks, coffee, cocoa drinks, beverages containing milk ingredients, beverages containing cereal extracts, and smoothies. In some embodiments, the beverage may be a soft drink.

In certain embodiments of any of the configurations and embodiments described herein involving a flavored product, the flavored product is a non-naturally occurring product, such as a packaged food or beverage product.

Other non-limiting examples of food and beverage products or formulations include sweetened coatings, frostings or icings of such products, or any entity included in the following: soups, dry processed foods, beverages, ready-to-eat foods, canned or preserved foods, frozen processed foods, refrigerated processed foods, snack foods, baked foods, confectionery, dairy products, ice cream, meal replacements, pasta and noodles, as well as sauces, dressings, condiments, baby foods and/or spreads.

In general, soups refer to canned/preserved, dehydrated, instant, refrigerated, UHT and frozen soups. For the purpose of this definition, soup refers to a food made from meat, poultry, fish, vegetables, grains, fruits and other ingredients, cooked in a liquid, which may contain visible fragments of some or all of these ingredients. It may be clear (as a stock) or thick (as a chowder), smooth, pureed or chunky, ready-to-eat, semi-concentrated or concentrated, and served hot or cold, as a first or main course or as a snack (sipping beverage) between meals. Soup can be used as a raw material for preparing other meal ingredients, ranging from broth (consommé) to sauces (cream- or cheese-based soups).

The Dehydrated and Cooking Foods category generally refers to: (i) cooking aid products, such as powdered, granulated, paste-like, concentrated liquid products, including concentrated bouillon, bouillon, and bouillon-like products in pressed blocks, tablets, or powdered or granulated form, sold individually as finished products or as ingredients in products, sauces, and recipe mixes (regardless of technology); (ii) dietary solution products, such as dehydrated soups and freeze-dried soups, including dehydrated soup mixes, dehydrated instant soups, dehydrated instant soups, dehydrated ready-to-eat soups, dehydrated or self-heating preparations of ready-made dishes, meals, and single-serving entrees, including pasta, potatoes, and rice; and (iii) dietary garnish products, such as condiments, marinades, salad dressings, salad toppings, dips, mixes, batter mixes, shelf-stable sauces, barbecue sauces, liquid recipe mixes, concentrates, sauces or sauce mixes, including salad recipe mixes, sold as finished products or as ingredients in products, whether dehydrated, liquid, or frozen.

Beverages generally refer to beverages, beverage mixes and concentrates, including but not limited to carbonated and non-carbonated beverages, alcoholic and non-alcoholic beverages, ready-to-drink beverages, liquid concentrates for preparing beverages (e.g., soda), and dry powder beverage precursor mixtures. Beverages also include alcoholic beverages, soft drinks, sports drinks, isotonic beverages and hot drinks. Alcoholic beverages include but are not limited to beer, cider/perry, FABs, wine and spirits. Soft drinks include but are not limited to carbonated beverages, such as cola and non-cola carbonated beverages; fruit juices, such as fruit juices, honey drinks, fruit drinks and fruit-flavored drinks; bottled water, including soda water, spring water and purified/table water; functional beverages, which can be carbonated or still beverages, including sports drinks, energy drinks or elixir drinks; concentrates, such as ready-to-drink liquids and powder concentrates. The beverages, whether hot or cold, include, but are not limited to, coffee or iced coffee, such as freshly ground coffee, instant coffee, and blended coffee; tea or iced tea, such as black tea, green tea, white tea, oolong tea, and flavored tea; and other beverages, including flavored, malt-based or plant-based powders, granules, blocks, or tablets mixed with milk or water.

Snacks (snack foods) generally refer to any food that is a simple, informal meal, including but not limited to sweet and savory (salty, spicy, etc. non-sweet) snacks and snack bars. Examples of snacks include but are not limited to fruit snacks, potato chips/crisps, extruded snacks, tortillas/corn chips, popcorn, pretzels, nuts and other sweet and savory snacks. Examples of snack bars include but are not limited to granola/cereal bars, breakfast bars, energy bars, fruit bars and other snack bars.

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

Ice cream generally refers to frozen desserts containing cream, sugar and flavorings. Examples of ice cream include, but are not limited to: impulse ice cream; family-packed ice cream; frozen yogurt and handmade ice cream; soy, oat, bean (such as red bean and mung bean) and rice-based ice cream.

Candy generally refers to edible products that are sweet in taste. Examples of candy include, but are not limited to, hard candy, gelatin, chocolate candy, granulated candy, chewing gum, etc. and any combination products.

The meal replacement category generally refers to any food that is intended to replace a normal meal, especially for those who are concerned with health or fitness. Examples of meal replacements include, but are not limited to, weight loss products and recovery products.

The ready-to-eat food category generally refers to any food that can be consumed as a meal without extensive preparation or processing. Ready-to-eat foods include products to which the manufacturer has added recipe "skills" so that they have a high degree of readiness, completeness, and convenience. Examples of ready-to-eat foods include, but are not limited to, canned/preserved, frozen, dried, refrigerated ready meals; dinner mixes; frozen pizza; refrigerated pizza; and prepared salads.

The Pasta and Noodle category includes any pasta and/or noodles, including but not limited to canned, dried and refrigerated/fresh pasta; and plain, instant, refrigerated, frozen and snack noodles.

The canned/preserved foods category includes, but is not limited to, canned/preserved meats and meat products, fish/seafood, vegetables, tomatoes, beans, fruits, ready meals, soups, pasta, and other canned/preserved foods.

The frozen processed food 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.

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 refrigerated processed food category includes, but is not limited to, refrigerated processed meats, processed fish/seafood products, lunch boxes, fresh-cut fruit, ready meals, pizza, prepared salads, soups, fresh pasta, and noodles.

The Sauces, Dressings and Condiments category includes, but is not limited to, tomato sauces 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, pickles, and other sauces, dressings and condiments.

The baby food category includes, but is not limited to, milk- or soy-based formulas; and prepared, dry, and other baby foods.

Spreads include, but are not limited to, jams and preserves, honey, chocolate spreads, nut spreads and yeast spreads.

Dairy products generally refer to edible products produced from the milk of mammals. Examples of dairy products include, but are not limited to, drinking milk products, cheese, yogurt and sour milk drinks, and other dairy products.

Additional examples of flavored products, particularly food and beverage products or formulations, are provided below. Exemplary ingestible compositions include one or more candies, chocolate candies, chocolate chips, chocolate slabs (countlines), bagged chocolate bars (selflines)/softlines, boxed varieties, standard boxed varieties, twist-wrapped miniature chocolates, flavored chocolates, chocolates with toys, sandwiches, other chocolate candies, mints, standard mints, strong mints, hard candies, pastilles, gums, jellies and chews, toffees, caramels and nougats, medicated candies, lollipops, licorice, other candies, breads, wraps, Packaged/industrial bread, bulk/artisan bread, pastries, cakes, packaged/industrial cakes, bulk/artisan cakes, biscuits, chocolate coated biscuits, sandwich biscuits, sandwich crackers, salty crackers and crackers, bread substitutes, breakfast cereals, ready-to-eat cereals, family breakfast cereals, flakes, cereals, other cereals, children's breakfast cereals, hot cereals, ice cream, ready-to-eat ice cream, single-serve dairy ice cream, single-serve water ice cream, multi-pack dairy ice cream, multi-pack water ice cream, family-pack ice cream, family-pack dairy ice cream, ice cream desserts, bulk ice cream, family-pack water ice cream, frozen yogurt , handmade ice cream, dairy products, milk, fresh/pasteurized milk, whole fat fresh/pasteurized milk, semi-skimmed fresh/pasteurized milk, long-life/UHT milk, whole fat long-life/UHT milk, semi-skimmed long-life/UHT milk, fat-free long-life/UHT milk, goat's milk, condensed milk/evaporated milk, plain condensed milk/evaporated milk, flavored, functional and other condensed milk, flavored milk drinks, only dairy flavored milk drinks, flavored milk drinks with fruit juice, soy milk, yogurt drinks, fermented milk drinks, coffee creamer, milk powder, flavored milk powder drinks, cream, cheese, processed dry cheese, spreadable cheese, processed cheese, non-spreadable, unprocessed cheese, spreadable unprocessed cheese, hard cheese, packaged hard cheese, unpackaged hard cheese, yogurt, plain/natural yogurt, flavored yogurt, fruit yogurt, probiotic yogurt, drinkable yogurt, regular drinkable yogurt, probiotic drinkable yogurt, frozen and shelf-stable snacks, dairy-based snacks, soy-based desserts, frozen snacks, fresh cheese and quark, plain fresh cheese and quark, flavored fresh cheese and quark, savory fresh cheese and quark, sweet and savory snacks, fruit snacks, chips/crisps, puffed snacks, cornmeal Corn flakes/corn chips, popcorn, pretzels, nuts, other sweet and savory snacks, snack bars, granola, breakfast bars, energy bars, fruit bars, other snack bars, meal replacements, weight loss products, recovery drinks, ready meals, canned ready meals, frozen ready meals, dried ready meals, frozen ready meals, dinner mixes, frozen pizza, refrigerated pizza, soup, canned soup, dehydrated soup, instant soup, cold soup, hot soup, frozen soup, pasta, canned pasta, dried pasta, frozen/fresh pasta, noodles, plain noodles, instant noodles, instant noodles in cups/bowls, instant noodles in bags Noodles, Frozen Noodles, Snack Noodles, Canned Foods, Canned Meat and Meat Products, Canned Fish/Seafood, Canned Vegetables, Canned Tomatoes, Canned Beans, Canned Fruit, Canned Ready-to-eat Foods, Canned Soups, Canned Pasta, Other Canned Foods, Frozen Foods, Frozen Processed Red Meat, Frozen Processed Poultry, Frozen Processed Fish/Seafood, Frozen Processed Vegetables, Frozen Meat Substitutes, Frozen Potatoes, Oven-baked Potato Chips, Other Oven-baked Potato Products, Non-oven Frozen Potatoes, Frozen Baked Foods, Frozen Desserts, Frozen Ready-to-eat Foods, Frozen Pizza, Frozen Soups, Frozen Noodles, Other Frozen Foods, Dried Foods, Desserts Mixes, Dried ready meals, Dehydrated soups, Instant soups, Dried pasta, Plain noodles, Instant noodles, Instant noodles in cups/bowls, Instant noodles in bags, Refrigerated foods, Refrigerated processed meats, Refrigerated fish/seafood products, Refrigerated processed fish, Refrigerated coated fish, Refrigerated smoked fish, Refrigerated lunch packs, Refrigerated ready meals, Refrigerated pizza, Refrigerated soups, Refrigerated/fresh pasta, Refrigerated noodles, Oils and fats, Olive oil, Vegetable and seed oils, Cooking fats, Butter, Margarine, Spreads, Functional spreads, Sauces, Seasonings and condiments, Tomato paste and puree, Broth/stock cubes, Stock cubes, Gravy granules, liquid stocks and stock, herbs and spices, fermented sauces, soy 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, marinades, other sauces, seasonings and condiments, baby food, formula, standard formula, growing-up formula, toddler formula, hypoallergenic formula, prepared baby food, dry baby food, other baby food, spreads, jams and preserves, honey, chocolate spreads, nut spreads, and yeast spreads. Exemplary ingestible compositions also include candies, baked goods, ice cream, dairy products, sweet and savory snacks, snack bars, meal replacement products, ready-to-eat foods, soups, pasta, noodles, canned foods, frozen foods, dry foods, refrigerated foods, oils and fats, baby food or spreads or mixtures thereof. Exemplary ingestible compositions also include breakfast cereals, sweetened beverages, or solid or liquid concentrate compositions for preparing beverages, ideally allowing for reduced concentrations of previously known carbohydrate sweeteners or artificial sweeteners.

Some embodiments provide chewable compositions that may or may not be swallowed. In some embodiments, the chewable composition may be gum, chewing gum, saccharified gum, sugarless gum, functional gum, bubble gum, which contain the compounds disclosed and described herein, alone or in combination.

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

In some embodiments, the compounds disclosed and described herein adjust the sweetness or other taste characteristics of other natural or synthetic sweet tastants and ingestible compositions prepared therefrom, either alone or in combination. In one embodiment, the compounds disclosed and described herein can be used or provided alone or in combination with their ligand-enhanced concentrations. For example, the amount of the compounds disclosed and described herein, alone or in combination, can be 0.001ppm to 100ppm, or a narrower alternative range of 0.1ppm to 50ppm, 0.01ppm to 40ppm, 0.05ppm to 30ppm, 0.01ppm to 25ppm, 0.1ppm to 30ppm, or 0.1ppm to 25ppm, or 1ppm to 30ppm, or 1ppm to 25ppm.

In some embodiments, the ingestible compositions disclosed herein can be provided in the form of flavoring concentrate preparations, either alone or in combination, such as being suitable for subsequent processing to produce ready-to-use (i.e., ready-to-eat) products. "Flavoring concentrate preparations" refer to preparations that should be reconstituted with one or more dilution media to become ready-to-use compositions. The term "ready-to-use composition" is used interchangeably with "ingestible composition" herein, and it means that no matter it is intended to be used for or not for consumption, any substance that can be taken orally, either alone or together with another substance. In one embodiment, the ready-to-use composition includes a composition that can be directly eaten by a human or animal. The flavoring concentrate preparation is usually used by mixing or diluting with one or more dilution media, such as any edible or ingestible ingredients or products, to impart or change the dilution medium with one or more flavorings. Such a use process is generally referred to as reconstitution. Reconstitution can be carried out in a home environment or an industrial environment. For example, a consumer can reconstitute a frozen fruit juice concentrate in a kitchen with water or other aqueous media to obtain a ready-to-use fruit juice beverage. In another example, soft drink syrup concentrate can be reconstituted with water or other aqueous media on a large-scale industrial scale by manufacturers to produce instant soft drinks. Since the concentration of the flavoring or seasoning that the flavoring concentrate preparation has is higher than the instant composition, the flavoring concentrate preparation is usually not suitable for direct consumption without reconstitution. There are many benefits to using and producing the flavoring concentrate preparation. For example, one benefit is to reduce the weight and volume of transportation, because the flavoring concentrate preparation can be reconstituted by adding a suitable solvent, solid or liquid when using.

The flavor product according to any of the foregoing embodiments further comprises, in certain embodiments, one or more additional flavor-modifying compounds, such as compounds that enhance sweetness (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), compounds that block bitterness, compounds that enhance umami taste, compounds that reduce sourness, compounds that enhance saltiness, compounds that enhance cooling effects, or any combination of the foregoing.

In certain embodiments of any of the forms and embodiments described herein involving a sweetening or flavoring concentrate, the sweetening or flavoring concentrate is a non-naturally occurring product, such as a composition specifically manufactured for the production of a flavored product, such as a food or beverage product.

In one embodiment, the flavoring concentrate formulation comprises i) a compound disclosed and described herein, either alone or in combination; ii) a carrier; and iii) optionally at least one adjuvant. The term "carrier" refers to a generally inactive auxiliary substance, such as a solvent, adhesive, or other inert medium, which is used in combination with the compounds of the present invention and one or more optional adjuvants to form a formulation. For example, water or starch can be a carrier for the flavoring concentrate formulation. In some embodiments, the carrier is the same as the dilution medium used to reconstitute the flavoring concentrate formulation; in other embodiments, the carrier is different from the dilution medium. As used herein, the term "carrier" includes, but is not limited to, an ingestible carrier.

The term "adjuvant" means an additive that supplements, stabilizes, maintains or enhances the expected function or efficacy of an active ingredient such as the compounds of the present invention. In one embodiment, at least one adjuvant comprises one or more flavoring agents. Flavoring agents can have any flavor known to those skilled in the art or consumers, such as chocolate, coffee, tea, mocha, French vanilla, peanut butter, Indian milk tea (chai), or the flavor of a combination thereof. In another embodiment, at least one adjuvant comprises one or more sweeteners. One or more sweeteners can be any sweetener described in the present application. In another embodiment, the at least one adjuvant comprises one or more ingredients selected from the group consisting of: emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, salts, and combinations thereof. Examples of emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates and salts are described in U.S. Patent No. 6,468,576, the entire contents of which are incorporated herein by reference for all purposes.

In one embodiment, the flavoring concentrate formulation of the present invention can be in the form of a liquid, solid, foam, paste, gel, emulsion and a combination thereof selected from solutions and suspensions, such as a liquid containing a certain amount of solid content. In one embodiment, the flavoring concentrate formulation is in the form of a liquid including water-based and non-aqueous. In some embodiments, the flavoring concentrate formulation of the present invention can be carbonated or non-carbonated.

The flavoring concentrate formulation may further include a freezing point depression agent, a nucleating agent or both as the at least one adjuvant. A freezing point depression agent is an acceptable compound or agent for ingestion, which can reduce the freezing point of a liquid or solvent to which the compound or agent has been added. That is, the freezing point of a liquid or solution containing a freezing point depression agent is lower than the freezing point of a liquid or solvent without a freezing point depression agent. In addition to reducing the initial freezing point, a freezing point depression agent can also reduce the water activity of the flavoring concentrate formulation. Examples of freezing point depression agents include, but are not limited to, carbohydrates, oils, ethanol, polyols such as glycerol and combinations thereof. A nucleating agent represents an acceptable compound or agent for ingestion that can promote nucleation. The presence of a nucleating agent in the flavoring concentrate formulation can improve the mouthfeel of slush, and helps maintain the physical properties and performance of slush at freezing temperatures by increasing the number of required ice crystal centers. Examples of nucleating agents include, but are not limited to, calcium silicate, calcium carbonate, titanium dioxide and combinations thereof.

In one embodiment, the flavoring 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 water activity of the flavoring concentrate formulation is less than about 0.85. In another embodiment, the water activity of the flavoring concentrate formulation is less than about 0.80. In another embodiment, the water activity of the flavoring concentrate formulation is less than about 0.75.

In one embodiment, the concentration of the compound in the flavoring concentrate formulation is at least 2 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavoring concentrate formulation is at least 5 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavoring concentrate formulation is at least 10 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavoring concentrate formulation is at least 15 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavoring concentrate formulation is at least 20 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavoring concentrate formulation is at least 30 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavoring concentrate formulation is at least 40 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavoring concentrate formulation is at least 50 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavoring concentrate formulation is at least 60 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the present compound in the flavoring concentrate formulation is up to 100 times the concentration of the compound in the ready-to-use composition.

In some embodiments, flavoring agents can be used in many different physical forms well known in the art to provide an initial flavor burst and/or a prolonged flavor sensation. Without being limited thereto, these physical forms include free forms, such as spray-dried, powdered, beaded forms, encapsulated forms, and mixed forms thereof.

In some embodiments, the ingestible composition comprises a flavor modification compound and a bulking agent according to any of the above-mentioned embodiments. 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, ribose, mannitol, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, oligofructose, cellulose and cellulose derivatives, 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 because they provide good content uniformity without increasing significant calories.

In one embodiment, at least one extender may be an extender as described in US Pat. No. 8,993,027.

In one embodiment, at least one extender may be an extender as described in US Pat. No. 6,607,771.

In one embodiment, at least one extender may be an extender as described in US Pat. No. 6,932,982.

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

In some embodiments, the sweetener composition of any of the foregoing forms and embodiments thereof is encapsulated using typical methods for encapsulating flavor or fragrance compounds. Non-limiting examples of such technologies are described in 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 2007/0128234, and U.S. Patent Nos. 7,488,503, All prior patent publications and patents are incorporated herein by reference as if set forth in their entirety herein.

Non-animal protein materials and products made therefrom

Products intended to replace or substitute meat or dairy products generally rely on various non-animal-based materials, such as starch and protein derived from plants, algae, fungi, or combinations thereof, to simulate the texture and flavor of meat or dairy products. Non-limiting examples of non-animal-based proteins are plant proteins, such as 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. Due to the compositional differences between such plant-based materials and materials derived from animals, such as the lack of glutamic acid-containing proteins and glutathione, these products may lack the umami or rich taste that consumers traditionally associate with meat or dairy products, or may have a bitter taste that animal protein lacks.

Therefore, in some forms, the present disclosure provides a flavored product, which includes plant-based materials (such as plant-based starch, plant-based protein or a combination thereof) and zinc salts according to any of the embodiments described. In some further embodiments, the flavored product may include any of the above-mentioned feature combinations for the ingestible composition containing zinc salts. In some embodiments, the flavored product is a beverage, such as soy milk, almond milk, rice milk, oat milk, protein beverage, meal replacement beverage or other similar products. In some other embodiments, the flavored product is a meat substitute product, such as a plant-based chicken product (such as a plant-based chicken nugget), a plant-based beef product (such as a plant-based burger), etc. In some other embodiments, the flavored product is a protein powder, a meal replacement powder, a plant-based creamer for coffee or tea, etc. In some other embodiments, any such product includes additional ingredients and has additional features, such as those commonly used in the preparation and/or manufacture of such products. For example, according to the known technology of the relevant field, the flavor modification compound can be combined with other flavoring agents and taste modifiers, and can even be encapsulated in certain materials. The suitable concentration of the flavor modification compound is as described above.

In some embodiments, the flavored product comprises one or more plant-based proteins that impart a bitter taste, which 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, faba bean protein, sunflower protein, wheat protein, oat protein, barley protein, potato protein, and combinations thereof.

In some further embodiments similar to the above embodiments, algae or fungal proteins or starch are used instead. In some embodiments, these flavored products also include fiber to provide texture to the product. Suitable fibers for use include but are not limited to psyllium fiber, pea fiber, potato fiber, curdlan, soluble corn fiber (glucan and/or maltodextrin), citrus fiber, and combinations thereof. In such products, flavor-modifying compounds can be introduced in any suitable manner. In some embodiments, flavor-modifying compounds are incorporated into a flavoring emulsion, such as a water-in-oil emulsion, together with other flavor-imparting ingredients.

Non-meat protein materials and products made therefrom

Some non-meat animal proteins, such as protein in milk protein and bone broth, are commonly used in food and are also sold as the main ingredient of some protein powders. Such proteins may impart a bitter taste that may not be desirable to consumers. This is especially true for protein isolates, such as protein isolates of whey protein, collagen, casein, etc. Therefore, the present disclosure provides an ingestible composition comprising non-meat animal protein and a flavor modification compound. According to the embodiments set forth in the previous part of the present disclosure, the flavor modification composition may exist in any suitable combination. In some embodiments, the non-meat animal protein is bone protein, such as collagen derived from animal bones, such as cattle, pigs, donkeys, horses, chickens, ducks, goats, geese, rabbits, lambs, sheep, buffaloes, ostriches, camels, etc. In some embodiments, the non-meat animal protein is milk protein, such as whey protein, casein, or any combination thereof. Milk can be the milk of any suitable animal, such as cattle, donkeys, horses, sheep, buffaloes, camels, etc.

The flavor-modifying composition can also be included in certain food or beverage products that include animal milk or materials derived from animal milk. Such products include cheese, cheese spreads, yogurt, kefir, milk, processed dairy products, cottage cheese, sour cream, butter, and the like.

Blocking bitter taste in pharmaceutical APIs

Many pharmaceutical compounds have bitter taste, thus limiting their formulation and mode of administration. Therefore, in certain forms, the present disclosure provides pharmaceutical compositions comprising bitter pharmaceutical active ingredients and flavor-modifying compounds. 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, adhesives, etc., such as those described in Remington's Pharmaceutical Sciences. In some embodiments, the bitter pharmaceutical active ingredient is an ion channel inhibitor, such as a proton channel inhibitor. Other examples of bitter APIs whose bitterness is reduced by flavor 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, orphenium bromide, pirenzepine, prednisolone, ranitidine, tripidil, trimethoprim, and cetirizine.

Uses in oral care products

Oral care products generally contain ingredients that impart astringency or bitterness. These ingredients include menthol, menthol analogs, peppermint extracts, sodium bicarbonate, alkali metal peroxymonosulfate (potassium peroxymonosulfate), cetylpyridinium chloride, lauroyl amidopropyl 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 agent, dentifrice, etc. Such oral care products may include flavor-modifying compounds to block or mask the bitterness of such compounds.

Example

To further illustrate the present invention, the following examples are included. Of course, these examples should not be construed as specifically limiting the present invention. Variations of these embodiments within the scope of the claims are within the capabilities of those skilled in the art and are considered to fall within the scope of the present invention as described and claimed herein. The reader will recognize that a skilled artisan and a person skilled in the art having grasped this disclosure will be able to prepare and use the present invention without exhaustive examples.

Example 1 - Sample preparation, Zanthoxylum bungeanum oil extract and sanshool

Commercially available Zanthoxylum bungeanolide (R1) was used as the raw material for fractionation and sensory studies. The chemical composition of commercially available Zanthoxylum bungeanolide (R1) was analyzed by GCMS and U(H)PLC-HRMS, and the following compounds were found: hydroxy-α-sanshool, hydroxy-γ-sanshool, hydroxy-β-sanshool, hydroxy-ε-sanshool, bungeanool, iso-sanshool, γ-sanshool, linalyl acetate, trans-hydrated sabinene acetate, α-pinene acetate, cis-hydrated sabinene acetate, 4-pinene acetate, linalool, 4-pinene alcohol, 1,8-cineole, α-pinene acetate, 1,8-cineole ... alcohol, α-elemenol, limonene, sabinene, myrcene, trans-hydrated sabinene, cis-hydrated sabinene, γ-terpinene, α-thujene, trans-β-ocimene, α-caryophyllene, myrcene D, δ-cadinene, α-terpinene, β-caryophyllene, γ-cadinene, glyceryl dicaprylate monocaprate, glyceryl 1,2-dicaprylate, glyceryl (1- or 2-) caprylate caprylate, glyceryl tricaprylate, glyceryl 1,3-dicaprylate and glyceryl 1-caprylate 3-caprylate.

About 40g of Zanthoxylum bungeanum oil (R1) was mixed with 360g of ethanol aqueous solution (53% w/w). The mixture was stirred (375rpm) 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 in a refrigerator overnight to 4°C. The oil phase was separated from the bottom aqueous phase. The aqueous phase was filtered through a 0.45μm PTFE membrane filter. About 16.0g of the oil phase and 358.0g of the ethanol extract aqueous solution (W2) were obtained. Both were refrigerated at 4°C until use.

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

The chemical components of the hydroalcoholic extract of Zanthoxylum bungeanum oil were analyzed by GCMS and U(H)PLC-HRMS, and the following compounds were identified: linalyl acetate, limonene, linalool, sabinene, 4-terpineol, α-terpineol acetate, myrcene (mycene), 1,8-cineole, trans-β-ocimene, myrcene D, α-terpineol, hydroxy-α-sanshool, hydroxy-β-sanshool, hydroxy-γ-sanshool, hydroxy-ε-sanshool; hydroxy-γ-isosanshool, hydroxy-γ-isosanshool I, sanshool, isosanshool, and sanshool. , γ-sanshool, 2',3'-dihydroxy-α-sanshool, tetrahydrocannabinol, 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-dodetetraenamide, (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-tetradecopentaenamide, (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-tetradecapentaenamide, N-(2-methylpropyl)-2,4,8,10-tetradecapentaenamide, 2,4,8,10-tetradecapentaenamide, N-(2-methylpropyl)-, (E,E,Z,Z)-, (2E,6E,8E,10E)-N-(2,3-dihydroxy-2-methylpropyl)-2,6,8,10-dodecapentaenamide, (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)-, dihydropiperidinol, (2E,4E)-N-(2 -methylpropyl)-8-oxo-2,4-tetradecadienamide; (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 -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-tetradecatetraenamide, and 2,4,9,11-tetradecatetraenamide, 8-hydroxy-N-(2-hydroxy-2-methylpropyl)-13-oxo, (2E,4E,9E,11E)-.

Sanshool standards hydroxy-β-sanshool (S3) and hydroxy-γ-sanshool (S2) were purchased from the market. The structure and purity were confirmed by NMR and LCHRMS analysis. Hydroxy-α-sanshool (S1) was isolated from the aqueous ethanol extract.

Then, 10.744g of dried extract of Zanthoxylum bungeanum oil extracted with aqueous ethanol was dissolved in 40mL of ethanol. The solution was then loaded onto the top of a flash column (80g, 150mL, ID3.12cm×H.19.5cm) filled with MCI gel (Mitsubishi Chemical Corp., CHP20). After adsorption, desorption was performed using 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 10mL/min. The fractions were characterized using the U(H)LC-HRMS C18 method. The fractions containing high-purity hydroxy-α-sanshool (>95%) were collected and dried, and the structure was confirmed by nuclear magnetic resonance analysis.

Example 2 - Sensory Analysis

The sensory properties (sweetness, licorice, sweet lingering aftertaste) of the samples with 0.2 or 5 ppm reference solution added were evaluated by a panel of 8 experts, with a score ranging from -5 to 5 (-5 indicates a strong masking effect, 5 indicates a strong enhancement effect, and 0 indicates the intensity of the reference aqueous solution containing 4% sucrose or 0.02% SG95). The results are shown in Table 2.

Table 2

In some embodiments of the present disclosure, the flavor modification composition provides many benefits, for example, the tested samples - pepper oil and sanshool extract - can significantly increase the sweetness intensity of solutions sweetened with sucrose or stevia extract. All tested samples - pepper oil and sanshool extract - can significantly mask the aftertaste of stevia extract.

An expert panel of 8 experts evaluated the sweetness characteristics of R1 added with various sweeteners at 50 ppm (0 means no sweetness, 10 means too strong sweetness). The dosage of sweeteners was designed according to their sweetness threshold in water. The results are shown in Table 3.

Table 3

In some embodiments of the present disclosure, the flavor modification composition provides many benefits. For example, the tested Zanthoxylum bungeanum oil (R1) can significantly enhance the sweetness of the compound solution, which includes solutions of naringenin, eriodictyol, homoeriodictyol, trilobatin, hesperidin dihydrochalcone 4'-O-glucoside, hesperidin dihydrochalcone, neohesperidin dihydrochalcone (NHDC), α-mogroside IV (2379350-24-8), mogroside V, rebaudioside A, malonyl rebaudioside A, rebaudioside E, malonyl rebaudioside E, and sweet leaf rubusoside.

Claims (22)

1. Use of a flavor-modifying composition for enhancing the sweet taste of an ingestible composition, wherein the flavor-modifying composition comprises one or more compounds of formula I: or a salt thereof, wherein: R ¹ is -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 ) ₂ ; and ^R2 is _C9 alkyl, _C11 alkyl, _C9 alkenyl or _C11 alkenyl, each of which is optionally substituted one or more times with hydroxy, oxo or a combination thereof. 2. The use according to claim 1, wherein ^R1 is _-CH2 -CH( _CH3 ) ₂ . 3. The use according to claim 1, wherein ^R1 is _-CH2 -C(= _CH2 ) _-CH3 . The use according to claim 1, wherein R ¹ is -CH ₂ -C(OH)(CH ₂ OH)(CH ₃ ). The use according to claim 1, wherein R ¹ is -CH ₂ -C(OH)(CH ₃ ) ₂ . 6. The use according to any one of claims 1 to 5, wherein ^R2 is a _C9 alkyl group, which is optionally substituted one or more times by hydroxyl, oxo or a combination thereof. 7. The method according to any one of claims 1 to 5, wherein ^R2 is a _C9 alkenyl group, which is optionally substituted one or more times by hydroxyl, oxo or a combination thereof. 8. The use according to any one of claims 1 to 5, wherein ^R2 is a _C11 alkyl group, which is optionally substituted one or more times by hydroxyl, oxo or a combination thereof. 9. The method according to any one of claims 1 to 5, wherein ^R2 is a _C11 alkenyl group, which is optionally substituted one or more times by hydroxyl, oxo or a combination thereof. 10. The use according to claim 1, wherein the flavor modification composition comprises one or more compounds selected from the group consisting of compounds 1 to 41, or edible acceptable salts thereof. 11. The use according to claim 1, wherein the flavor-modifying composition comprises hydroxy-α-sanshool. 12. The use according to claim 1, wherein the flavor-modifying composition comprises hydroxy-β-sanshool. 13. The use according to claim 1, wherein the flavor-modifying composition comprises hydroxy-γ-sanshool. 14. The use according to any one of claims 1 to 13, wherein the flavor modifying composition comprises Zanthoxylum bungeanum oil extract. 15. The use according to claim 14, wherein the extract is obtained by an extraction process comprising contacting Zanthoxylum bungeanum oil with an extraction medium, wherein the extraction medium comprises water, a water-miscible solvent, or a combination thereof. 16. Use according to claim 15, wherein the extraction medium comprises water and ethanol. 17. Use according to any one of claims 1 to 16, wherein the ingestible composition comprises a sweetener. 18. The use according to claim 17, wherein the sweetener is naringenin, eriodictyol, homoeriodictyol, trilobatin, hesperidin dihydrochalcone, hesperidin dihydrochalcone-4'-O-glucoside, neohesperidin dihydrochalcone, α-mogroside IV, mogroside V, rebaudioside A, malonyl rebaudioside A, malonyl rebaudioside E, rebaudioside E, rebaudioside M, rubusoside or any combination thereof. 19. The use according to claim 17, wherein the sweetener is a high intensity sweetener, such as acesulfame potassium, aspartame, neotame, cyclamate, saccharin, sucralose, steviol glycosides (such as rebaudioside A, rebaudioside B, rebaudioside M, rebaudioside D, or rebaudioside E), and mogrosides (such as mogroside III, mogroside IV, mogroside V, simonoside I, isomogroside V, mogroside IV _E , isomogroside IV, mogroside III _E , 11-oxomogroside V, or the 1,6-α isomer of simonoside I), or any combination thereof. 20. The use according to claim 18 or 19, wherein the concentration of the sweetener is below the sweetness threshold. 21. The use according to any one of claims 1 to 19, wherein the concentration of the sanshool compound used in the ingestible composition ranges from 0.001 ppm to 1000 ppm. 22. A method of enhancing the sweet taste of an ingestible composition, the method comprising introducing a flavor-modifying composition into the ingestible composition, wherein the flavor-modifying composition comprises one or more compounds of Formula I: or a salt thereof, wherein: R ¹ is -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 ) ₂ ; and ^R2 is _C9 alkyl, _C11 alkyl, _C9 alkenyl or _C11 alkenyl, each of which is optionally substituted one or more times with hydroxy, oxo or a combination thereof.