Flavonoid compound and application thereof

Abstract

The present disclosure relates to the field of flavour or perfume industry. The present invention relates to a liquid composition and, more specifically, to a liquid composition comprising a compound of formula (I) and / or a compound of formula (II), an oil comprising carvone and optionally a solvent. The present disclosure also relates to the use of said compositions in consumer products, such as flavored products and body care products.

Description

[0001] Cross - reference to related applications

[0002] This application claims priority to U.S. Provisional Application No. 63 / 381,254, filed on October 27, 2022, and European Application No. 23156674.6, filed on February 15, 2023, which are hereby incorporated by reference herein in their entirety as if fully set forth herein. Technical field

[0003] The present disclosure relates to the field of flavor or perfumery. More specifically, it relates to a liquid composition comprising a compound of formula (I) and / or a compound of formula (II), an oil containing carvone, and optionally a solvent. The present disclosure also relates to the use of said composition in consumer products such as flavored products and body care products. Background art

[0004] Throughout the animal kingdom, from simple metazoans to the most complex vertebrates, there are taste and sensory systems that can provide sensory information about the chemical composition of the external world. Such sensory information may include a cooling sensation as well as taste sensations such as sweetness.

[0005] Menthol modulates the TRPM8 receptor in a way that produces a cooling sensation in the oral cavity. This is why natural products containing menthol, such as mint extracts, tend to produce a cooling effect in the mouth. For the same reason, menthol is often used as an ingredient in non - extract dental flavorings where a cooling effect needs to be imparted. Even so, menthol can have a bitter or astringent taste, which some users may find objectionable.

[0006] Certain synthetic compounds, so - called cooling - enhancing compounds, can be used to enhance the cooling effect of menthol, thereby reducing the concentration of menthol while reducing the undesirable astringent or bitter taste. Due to the strength of these cooling - enhancing compounds, they are usually diluted in a solvent, especially a solvent approved for mucosal or skin consumer products. However, at room temperature and atmospheric pressure, such compounds are solids and have low solubility in the most common flavor and perfume solvents.

[0007] Sweetness is the most commonly perceived taste when consuming sugar - rich foods. Caloric sweeteners, such as sucrose and fructose, are typical examples of sweet substances. Caloric sweeteners are a key factor contributing to the prevalence of metabolic disorders and related diseases such as obesity, diabetes, and cardiovascular diseases. Despite the existence of various non - caloric and low - caloric alternatives, many consumers do not consider them to be suitable substitutes because their mere presence in food or beverages causes many such consumers to experience unpleasant off - flavors, including astringency, bitterness, metallic taste, and licorice taste.

[0008] As with cooling, flavor modifying compounds such as sweetness enhancing compounds can be used to provide an alternative approach to overcome some of the application challenges 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 smaller amounts of such caloric sweeteners in a variety of food or beverage products. However, like cooling enhancing compounds, some sweetness enhancing compounds are solids, have low solubility in the most common flavor and fragrance solvents, and are too strong to be used in undiluted form, making them difficult to handle and incorporate into consumer products.

[0009] Accordingly, there has been a continuing need for suitable solvents to dissolve the above types of sensory enhancing compounds in order to provide these compounds in a more convenient diluted form. SUMMARY OF THE INVENTION

[0010] The following aspects of the present disclosure are directed to solving one or more of the above problems.

[0011] In a first aspect, the present invention relates to a liquid composition comprising:

[0012] a) a compound of formula (I)

[0013]

[0014] or a salt thereof, wherein:

[0015] R 1 is a hydrogen atom, -OH or -O-R 1A ;

[0016] R 1A is a C 1-6 alkyl group which may be optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 1A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0017] R 2 is a hydrogen atom, -OH or -O-R 2A ;

[0018] R 2A is a C 1-6 alkyl group which may be optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy, or R 2A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0019] R 3 is -OH or -O-R 3A ;

[0020] R 3A is C 1-6 alkyl, which is optionally substituted one or more times by substituents selected from -OH and C 1-6 alkoxy; or R 3A is a glucuronyl moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0021] R 4 is a hydrogen atom, -OH or -O-R 4A ;

[0022] R 4A is C 1-6 alkyl, which is optionally substituted one or more times by substituents selected from -OH and C 1-6 alkoxy; or R 4A is a glucuronyl moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0023] R 5 is a hydrogen atom, -OH, -O-R 5A or -OC(O)-R 5B ;

[0024] R 5A is C 1-6 alkyl, which is optionally substituted one or more times by substituents selected from -OH and C 1-6 alkoxy; or R 5A is a glucuronyl moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0025] R 5B is -H or C 1-6 alkyl, which is optionally substituted one or more times by substituents selected from -OH and C 1-6 alkoxy;

[0026] R 6 and R 7 are independently selected from C 1-6 alkyl, -OH, C 1-6 alkoxy and -O-(C 1-6 alkylene)-O-(C 1-6 alkyl);

[0027] m is 0, 1 or 2; and

[0028] n is 0, 1, 2 or 3;

[0029] or

[0030] a compound of formula (II)

[0031]

[0032] or a salt thereof, wherein:

[0033] R 8 is a hydrogen atom, -OH or -O-R 8A ;

[0034] R 8A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 8A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0035] R 9 is a hydrogen atom, -OH or -O-R 9A ;

[0036] R 9A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy, or R 9A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0037] R 10 is -OH or -O-R 10A ;

[0038] R 10A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 10A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0039] R 11 is a hydrogen atom, -OH or -O-R11A ;

[0040] R 11A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 11A is a glucuronyl moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0041] R 12 is a hydrogen atom, -OH, -O-R 12A or -OC(O)-R 12B ;

[0042] R 12A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 12A is a glucuronyl moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0043] R 12B is -H or C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy;

[0044] R 13 and R 14 are independently selected from C 1-6 alkyl, -OH, C 1-6 alkoxy and -O-(C 1-6 alkylene)-O-(C 1-6 alkyl);

[0045] m' is 0, 1 or 2; and

[0046] n' is 0, 1, 2 or 3; or a combination thereof;

[0047] b) an oil containing carvone; and

[0048] c) an optionally used solvent.

[0049] In a second form, the present disclosure relates to a consumer product comprising the liquid composition described herein. Detailed embodiments

[0050] The following detailed description sets forth various forms and embodiments provided herein. This description should be read from the perspective of a person of ordinary skill in the relevant art. Accordingly, information well known to those of ordinary skill is not necessarily included. It will be apparent to those of ordinary skill that the various forms and embodiments provided herein may be combined in any manner without departing from the spirit of the disclosure.

[0051] Unless otherwise specified herein, the following terms and phrases have the indicated meanings. The disclosure may employ other terms and phrases not expressly defined herein. Such other terms and phrases have the meanings that would be understood by a person of ordinary skill in the context of the disclosure. In some cases, a term or phrase may be defined in either the singular or the plural. In such cases, it should be understood that unless expressly stated to the contrary, any term in the singular may include its plural form and vice versa. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this specification belongs.

[0052] As used herein, unless otherwise indicated, the terms “a,” “an,” or “the” each mean “one or more” or “at least one.”

[0053] Although the compositions and methods are described in terms of “comprising,” “containing,” or “including” various components or steps, the compositions and methods may also “consist essentially of” or “consist of” the various components, substances, and steps. As used herein, the term “consist essentially of” shall be interpreted to include the recited components, substances, or steps, as well as such additional components, substances, or steps that do not materially affect the basic and novel properties of the composition or method. In some embodiments, a composition “consisting essentially of the recited components or substances” according to an embodiment of the disclosure does not include any additional components or substances that alter the basic and novel properties of the composition.

[0054] It should be understood that any numerical range recited herein is intended to include all sub-ranges subsumed therein. For example, a range of “1 to 10” is intended to include all sub-ranges between the recited minimum value of 1 and the recited maximum value of 10; that is, having a minimum value equal to or greater than 1 and a maximum value equal to or less than 10. Since the disclosed numerical ranges are continuous, they include every value between the minimum and maximum values. Unless expressly stated otherwise, the various numerical ranges specified in this application are approximations.

[0055] As used herein, unless otherwise specified, the terms "about" or "approximately" refer to an acceptable error of a particular value as determined by one of ordinary skill in the art, which depends in part on how the value is measured or determined. In certain embodiments, the terms "about" or "approximately" refer to within 1, 2, 3, or 4 standard deviations. In certain embodiments, the terms "about" or "approximately" refer to within 50%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, or 0.05% of a given value or range.

[0056] Throughout this disclosure, various publications may be incorporated by reference. If any term in these publications incorporated by reference conflicts with the meaning of the terms of this disclosure, the meaning of the terms of this disclosure shall control, unless otherwise specified.

[0057] As used herein, "solvate" refers to a compound formed by the interaction of one or more solvent molecules with one or more compounds described herein. In some embodiments, the solvate is a pharmaceutically acceptable solvate, such as a hydrate.

[0058] As used herein, "C a to C b " or "C a-b " 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 from 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-.

[0059] As used herein, "halogen" or "halo" refers to any of the radioactively stable atoms in column 7 of the periodic table, such as fluorine, chlorine, bromine, or iodine. In some embodiments, "halogen" or "halo" refers to fluorine or chlorine.

[0060] 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 has 1 to 20 carbon atoms (when a numerical range such as "1 to 20" appears herein, it refers to each integer within the given range; for example, "1 to 20 carbon atoms" means that the alkyl can consist of 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc., up to and including 20 carbon atoms, although this definition also encompasses the occurrence of the term "alkyl" where no numerical range is specified). The alkyl can also be a medium-sized alkyl having 1 to 9 carbon atoms. The alkyl can also be a lower alkyl having 1 to 4 carbon atoms. The alkyl can be referred to as "C 1-4 alkyl" or a similar name. By way of example only, "C 1-4 alkyl" indicates the presence of 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl. Typical alkyls include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, etc. Unless otherwise indicated, the term "alkyl" refers to an unsubstituted group.

[0061] As used herein, "substituted alkyl" refers to an alkyl substituted with one or more substituents independently selected from the following groups: C 1 -C 6 alkenyl, C 1 -C 6 alkynyl, C 1 -C 6 heteroalkyl, C 3 -C 7 carbocyclic group (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, and C 1 -C 6 haloalkoxy), a 3- to 10-membered heterocyclic group (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, and C 1 -C 6 haloalkoxy), aryl (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C1 -C 6 haloalkyl and C 1 -C 6 (haloalkoxy), 5- to 10-membered heteroaryl (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 (haloalkoxy), halogen, cyano, hydroxy, C 1 -C 6 alkoxy, aryloxy (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 (haloalkoxy), C 3 -C 7 carbocyclooxy (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 (haloalkoxy), 3- to 10-membered heterocyclooxy (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 (haloalkoxy), 5- to 10-membered heteroaryloxy (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 (haloalkoxy), C 3 -C 7 -carbocyclo-C 1 -C 6 alkoxy (optionally substituted with halogen, C 1 -C6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 3- to 10-membered heterocyclic group-C 1 -C 6 -alkoxy (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), aryl(C 1 -C 6 )alkoxy (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 5- to 10-membered heteroaryl(C 1 -C 6 )alkoxy (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), hydrogen sulfide group (mercapto), halo(C 1 -C 6 )alkyl (e.g., -CF 3 )), halo(C 1 -C 6 )alkoxy (e.g., -OCF 3 ), C 1 -C 6 alkylthio, arylthio (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), C 3 -C7 A carbocyclic thio group (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), a 3- to 10-membered heterocyclic thio group (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), a 5- to 10-membered heteroaryl thio group (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), C 3 -C 7 -carbocyclic-C 1 -C 6 -alkylthio (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), a 3- to 10-membered heterocyclic-C 1 -C 6 alkylthio (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), an aryl (C 1 -C 6 ) alkylthio (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C6 Halogenoalkyl and C 1 -C 6 halogenoalkoxy), 5- to 10-membered heteroaryl (C 1 -C 6 )) alkylthio (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 halogenoalkyl and C 1 -C 6 halogenoalkoxy), amino, nitro, O-carbamoyl, N-carbamoyl, O-thiocarbamoyl, N-thiocarbamoyl, C-amide, N-amide, S-sulfonamide, N-sulfonamide, C-carboxy, O-carboxy, acyl, cyanato, isocyanato, thiocyanato, isothiocyanato, sulfinyl, sulfonyl, and oxo (=O).

[0062] As used herein, "alkoxy" refers to a group of the formula -OR, where R is alkyl as defined above, for example "C 1-9 alkoxy", including but not limited to methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), n-butoxy, isobutoxy, sec-butoxy, and tert-butoxy, etc.

[0063] As used herein, "alkylthio" refers to a group of the formula -SR, where R is alkyl as defined above, for example "C 1-9 alkylthio", etc., including but not limited to methylthio, ethylthio, n-propylthio, 1-methylethylthio (isopropylthio), n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, etc.

[0064] As used herein, "alkenyl" refers to a straight-chain or branched hydrocarbon chain containing one or more double bonds. In some embodiments, alkenyl has 2 to 20 carbon atoms, although this definition also encompasses occurrences of the term "alkenyl" where no numerical range is specified. Alkenyl can also be a medium-sized alkenyl having 2 to 9 carbon atoms. Alkenyl can also be a lower alkenyl having 2 to 4 carbon atoms. Alkenyl can be referred to as "C 2-4 alkenyl" or a similar name. By way of example only, "C 2-4"Alkenyl" means that there are 2 to 4 carbon atoms in the alkenyl chain, that is, the alkenyl chain is selected from the group consisting of: vinyl, prop-1-enyl, prop-2-enyl, prop-3-enyl, but-1-enyl, but-2-enyl, but-3-enyl, but-4-enyl, 1-methyl-prop-1-enyl, 2-methyl-prop-1-enyl, 1-ethyl-vinyl-1-enyl, 2-methyl-prop-3-enyl, buta-1,3-dienyl, buta-1,2-dienyl, and buta-1,2-dien-4-yl. Typical alkenyl groups include, but are not limited to, vinyl, propenyl, butenyl, pentenyl, and hexenyl, etc. Unless otherwise indicated, the term "alkenyl" refers to an unsubstituted group.

[0065] As used herein, "alkynyl" refers to a straight or branched hydrocarbon chain containing one or more triple bonds. In some embodiments, alkynyl has 2 to 20 carbon atoms, although this definition also encompasses occurrences of the term "alkynyl" where no numerical range is specified. Alkynyl can also be a medium-sized alkynyl having 2 to 9 carbon atoms. Alkynyl can also be a lower alkynyl having 2 to 4 carbon atoms. Alkynyl can be referred to as "C 2-4 alkynyl" or a similar name. By way of example only, "C 2-4 alkynyl" means that there are 2 to 4 carbon atoms in the alkynyl chain, that is, the alkynyl chain is selected from the group consisting of: ethynyl, prop-1-ynyl, prop-2-ynyl, but-1-ynyl, but-3-ynyl, but-4-ynyl, and 2-butynyl. Typical alkynyl groups include, but are not limited to, ethynyl, propynyl, butynyl, pentynyl, and hexynyl, etc. Unless otherwise indicated, the term "alkynyl" refers to an unsubstituted group.

[0066] As used herein, "heteroalkyl" refers to a straight or branched hydrocarbon chain containing one or more heteroatoms, i.e., elements other than carbon, in the main chain of the chain, and the heteroatoms include, but are not limited to, nitrogen, oxygen, and sulfur. In some embodiments, heteroalkyl has 1 to 20 carbon atoms, although this definition also encompasses occurrences of the term "heteroalkyl" where no numerical range is specified. Heteroalkyl can also be a medium-sized heteroalkyl having 1 to 9 carbon atoms. Heteroalkyl can also be a lower heteroalkyl having 1 to 4 carbon atoms. Heteroalkyl can be referred to as "C 1-4 heteroalkyl" or a similar name. Heteroalkyl can contain one or more heteroatoms. By way of example only, "C 1-4 heteroalkyl" means that there are one to four carbon atoms in the heteroalkyl chain and one or more additional heteroatoms in the main chain of the chain. Unless otherwise indicated, the term "heteroalkyl" refers to an unsubstituted group.

[0067] As used herein, "alkylene" refers to a fully saturated, branched or straight-chain diradical chemical group containing only carbon and hydrogen, which is attached to the remainder of the molecule through two attachment points (i.e., alkanediyl). In some embodiments, the alkylene has from 1 to 20 carbon atoms, although this definition also encompasses occurrences of the term alkylene where no numerical range is specified. The alkylene can also be a medium-sized alkylene having from 1 to 9 carbon atoms. The alkylene can also be a lower alkylene having from 1 to 4 carbon atoms. The alkylene can be referred to as "C 1-4 alkylene" or a similar name. By way of example only, "C 1-4 alkylene" indicates the presence of from 1 to 4 carbon atoms in the alkylene chain, i.e., the alkylene chain is selected from the group consisting of methylene, ethylene, ethane-1,1-diyl, propylene, propane-1,1-diyl, propane-2,2-diyl, 1-methyl-ethylene, butylene, butane-1,1-diyl, butane-2,2-diyl, 2-methyl-propane-1,1-diyl, 1-methyl-propylene, 2-methyl-propylene, 1,1-dimethyl-ethylene, 1,2-dimethyl-ethylene, and 1-ethyl-ethylene. Unless indicated to the contrary, the term "alkylene" refers to a group that is not further substituted.

[0068] As used herein, "alkenylene" refers to a straight-chain or branched-chain diradical chemical group containing only carbon and hydrogen and containing at least one carbon-carbon double bond, which carbon-carbon double bond is attached to the remainder of the molecule through two attachment points. In some embodiments, the alkenylene has from 2 to 20 carbon atoms, although this definition also encompasses occurrences of the term alkenylene where no numerical range is specified. The alkenylene can also be a medium-sized alkenylene having from 2 to 9 carbon atoms. The alkenylene can also be a lower alkenylene having from 2 to 4 carbon atoms. The alkenylene group can be referred to as "C 2-4 alkenylene" or a similar name. By way of example only, "C 2-4"Alkenylene" means having 2 to 4 carbon atoms in the alkenylene chain, i.e., the alkenylene chain is selected from the group consisting of: vinylene, ethene-1,1-diyl, propenylene, propene-1,1-diyl, prop-2-ene-1,1-diylidene, 1-methyl-vinylene, but-1-enylene, but-2-enylene, buta-1,3-dienyl, butene-1,1-diyl, buta-1,3-diene-1,1-diyl, but-2-ene-1,1-diyl, but-3-ene-1,1-diyl, 1-methyl-prop-2-ene-1,1-diyl, 2-methyl-prop-2-ene-1,1-diyl, 1-ethyl-vinylene, 1,2-dimethyl-vinylene, 1-methyl-propenylene, 2-methyl-propenylene, 3-methyl-propenylene, 2-methyl-propene-1,1-diyl and 2,2-dimethyl-ethene-1,1-diyl. Unless otherwise indicated, the term "alkenylene" refers to an unsubstituted group.

[0069] As used herein, "aromatic" refers to a ring or ring system having a conjugated π electron system and includes carbocyclic aromatic groups (such as phenyl) and heterocyclic aromatic groups (such as pyridine). The term includes monocyclic or fused polycyclic (i.e., rings sharing adjacent pairs of atoms) groups provided that the entire ring system is aromatic.

[0070] As used herein, "aryl" refers to an aromatic ring or ring system containing only carbon in the ring backbone (i.e., two or more fused rings sharing two adjacent carbon atoms). When aryl is a ring system, each ring in the system is aromatic. In some embodiments, aryl has 6 to 18 carbon atoms, although this definition also encompasses occurrences of the term "aryl" where no numerical range is specified. In some embodiments, aryl has 6 to 10 carbon atoms. Aryl may be referred to as "C 6-10 aryl", "C 6 -C 10 aryl" or similar names. Examples of aryl include, but are not limited to, phenyl, naphthyl, azulyl and anthryl. In some embodiments, the term "aryl" refers to phenyl. Unless otherwise indicated, the term "aryl" refers to an unsubstituted group.

[0071] As used herein, "aryloxy" and "arylthio" denote moieties of the formula RO- and RS-, respectively, where R is aryl as defined above, such as "C 6-10 aryloxy" or "C 6-10 arylthio" etc., including but not limited to phenoxy and phenylthio.

[0072] As used herein, "aralkyl" or "arylalkyl" refers to an aryl attached as a substituent via an alkylene, such as "C 7-14"Arylalkyl", etc., including but not limited to benzyl, 2-phenylethyl, 3-phenylpropyl, etc. In some embodiments, the alkylene is a lower alkylene (i.e., C 1-4 alkylene).

[0073] As used herein, "heteroaryl" refers to an aromatic ring or ring system (i.e., two or more fused rings sharing two adjacent atoms) that contains one or more heteroatoms, i.e., elements other than carbon (including but not limited to nitrogen, oxygen, and sulfur) in the ring skeleton. When heteroaryl is a ring system, each ring in the system is aromatic. In some embodiments, heteroaryl has 5 to 18 ring members (i.e., the number of atoms making up the ring skeleton, including carbon atoms and heteroatoms), although this definition also encompasses occurrences of the term "heteroaryl" where no numerical range is specified. In some embodiments, heteroaryl has 5 to 10 ring members or 5 to 7 ring members. Heteroaryl can be referred to as "5- to 7-membered heteroaryl", "5- to 10-membered heteroaryl", or similar designations. Examples of heteroaryl rings include but are not limited to furyl, thienyl, phthalazinyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, triazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquilinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indolyl, isoindolyl, and benzothienyl. Unless otherwise indicated, the term "heteroaryl" refers to an unsubstituted group.

[0074] As used herein, "heteroarylalkyl" or "heteroaryl-alkyl" refers to a heteroaryl attached as a substituent via an alkylene. Examples include but are not limited to 2-thienylmethyl, 3-thienylmethyl, furylmethyl, thienylethyl, pyrrolylalkyl, pyridylalkyl, isoxazolylalkyl, and imidazolylalkyl. In certain cases, the alkylene is a lower alkylene (i.e., C 1-4 alkylene).

[0075] As used herein, "carbocyclic group" refers to a non-aromatic ring or ring system that contains only carbon atoms in the ring system skeleton. When a carbocyclic group is a ring system, two or more rings can be fused, bridged, or spiro-linked together. A carbocyclic group can have any degree of saturation, provided that at least one ring in the ring system is not aromatic. Thus, carbocyclic groups include cycloalkyl, cycloalkenyl, and cycloalkynyl. In some embodiments, a carbocyclic group has 3 to 20 carbon atoms, although this definition also encompasses occurrences of the term "carbocyclic group" where no numerical range is specified. A carbocyclic group can also be a medium-sized carbocyclic group having 3 to 10 carbon atoms. A carbocyclic group can also be a carbocyclic group having 3 to 6 carbon atoms. Carbocyclic groups can be referred to as "C 3-6"carbocyclic group" or similar name. Examples of carbocyclic groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, 2,3-dihydroindene, bicyclo[2.2.2]octyl, adamantyl, and spiro[4.4]nonyl. Unless otherwise indicated, the term "carbocyclic group" refers to a group that is not further substituted.

[0076] As used herein, "(carbocyclic group)alkyl" refers to a carbocyclic group attached as a substituent via an alkylene group, such as "C 4-10 (carbocyclic group)alkyl", etc., including but not limited to cyclopropylmethyl, cyclobutylmethyl, cyclopropylethyl, cyclopropylbutyl, cyclobutylethyl, cyclopropylisopropyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, cyclohexylethyl, cycloheptylmethyl, and the like. In certain cases, the alkylene group is a lower alkylene group.

[0077] As used herein, "cycloalkyl" refers to a fully saturated carbocyclic ring or ring system according to any of the embodiments described above for carbocyclic groups. Examples include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0078] As used herein, "cycloalkenyl" refers to a carbocyclic ring or ring system having at least one double bond, wherein no ring in the ring system is aromatic, and according to any of the embodiments described above for carbocyclic groups. An example is cyclohexenyl.

[0079] As used herein, "heterocyclic group" refers to a non-aromatic ring or ring system that contains at least one heteroatom in the ring skeleton. Heterocyclic groups can be joined together in a fused, bridged, or spiro-linked fashion. Heterocyclic groups can have any degree of saturation provided that at least one ring in the ring system is not aromatic. Heteroatoms can be present in non-aromatic or aromatic rings of the ring system. In some embodiments, the heterocyclic group has from 3 to 20 ring members (i.e., the number of atoms making up the ring skeleton, including carbon atoms and heteroatoms), although this definition also encompasses occurrences of the term "heterocyclic group" where no numerical range is specified. The heterocyclic group can also be a medium-sized heterocyclic group having from 3 to 10 ring members. The heterocyclic group can also be a heterocyclic group having from 3 to 6 ring members. The heterocyclic group can be referred to as a "3- to 6-membered heterocyclic group" or a similar name. In a preferred six-membered monocyclic heterocyclic group, the heteroatoms are selected from one to up to three of O, N, or S, and in a preferred five-membered monocyclic heterocyclic group, the heteroatoms are selected from one or two heteroatoms selected from O, N, or S. Examples of heterocyclic rings include, but are not limited to, azepinyl, acridinyl, carbazolyl, cinnolinyl, dioxolanyl, imidazolinyl, imidazolidinyl, morpholinyl, oxiranyl, oxepanyl, thiepanyl, piperidinyl, piperazinyl, dioxopiperazinyl, pyrrolidinyl, pyrrolidonyl, pyrrolidionyl, 4-piperidonyl, pyrazolinyl, pyrazolidinyl, 1,3-dioxinyl, 1,3-dioxanyl, 1,4-dioxinyl, 1,4-dioxanyl, 1,3-oxathianyl, 1,4-oxathiinyl, 1,4-oxathianyl, 2H-1,2-oxazinyl, trioxanyl, hexahydro-1,3,5-triazinyl, 1,3-dioxolyl, 1,3-dioxolanyl, 1,3-dithiolyl, 1,3-dithiolanyl, isoxazolinyl, isoxazolidinyl, oxazolinyl, oxazolidinyl, oxazolidinone, thiazolinyl, thiazolidinyl, 1,3-oxathiolanyl, indolinyl, isoindolinyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothienyl, tetrahydrothiopyranyl, tetrahydro-1,4-thiazinyl, thiamorpholinyl, dihydrobenzofuranyl, benzimidazolidinyl, and tetrahydroquinoline.

[0080] As used herein, “(heterocyclic group)alkyl” refers to a heterocyclic group attached via an alkylene group as a substituent. Examples include, but are not limited to, imidazolinylmethyl and indolinylethyl.

[0081] “Acyl” refers to -C(=O)R, where R is hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein. Non-limiting examples include formyl, acetyl, propionyl, benzoyl, and acryloyl.

[0082] “O-carboxy” refers to the group “-OC(=O)R”, where R is selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein.

[0083] “C-carboxy” refers to the group “-C(=O)OR”, where R is selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein. Non-limiting examples include carboxy (i.e., -C(=O)OH).

[0084] The “cyano” group refers to the group “-CN”.

[0085] The “cyanate” group refers to the group “-OCN”.

[0086] The “isocyanate” group refers to the group “-NCO”.

[0087] The “thiocyanate” group refers to the group “-SCN”.

[0088] The “isothiocyanate” group refers to the group “-NCS”.

[0089] “Sulfinyl” refers to the group “-S(=O)R”, where R is selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein.

[0090] “Sulfonyl” means “-SO 2 R” group, where R is selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein.

[0091] “S-sulfamoyl” means “-SO 2 NR A R B ” group, where R A and R B are each independently selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein.

[0092] “N-sulfamoyl” means “-N(R A )SO 2 R B ” group, where R A and R B are each independently selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein.

[0093] “O-carbamoyl” means “-OC(=O)NR A R B ” group, where R A and R B are each independently selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein.

[0094] “N-carbamoyl” means “-N(R A )C(=O)OR B ” group, where R A and R B are each independently selected from hydrogen, C 1-6 alkyl, C2-6 Alkenyl, C 2-6 Alkynyl, C 3-7 Carbocyclic group, C 6-10 Aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein.

[0095] "O-thiocarbamoyl" means "-OC(=S)NR A R B " group, wherein R A and R B are each independently selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein.

[0096] "N-thiocarbamoyl" means "-N(R A )C(=S)OR B " group, wherein R A and R B are each independently selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein.

[0097] "C-amido" means "-C(=O)NR A R B " group, wherein R A and R B are each independently selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein.

[0098] "N-amido" means "-N(R A )C(=O)R B " group, wherein R A and R B are each independently selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10An aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein.

[0099] "Amino" means "-NR A R B " group, wherein R A and R B are each independently selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 carbocyclic group, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclic group, as defined herein. Non-limiting examples include a free amino group (i.e., -NH 2 ).

[0100] "Aminoalkyl" means an amino group linked via an alkylene group.

[0101] "Alkoxyalkyl" means an alkoxy group linked via an alkylene group, such as "C 2-8 alkoxyalkyl", etc.

[0102] As used herein, a "glucosyl moiety" is a monovalent moiety in which a hydroxyl group of glucose is replaced by a bond, functional group, or moiety that is linked to another atom. Unless otherwise specified, glucose can have any suitable stereochemistry. Thus, the term includes moieties having D-stereochemistry as well as moieties having L-stereochemistry. In addition, the term includes moieties having α-stereochemistry as well as moieties having β-stereochemistry. The carbon atoms of the glucosyl moiety follow the conventional numbering as shown below. This figure shows β-D-glucose, but applies in a similar manner to glucosyl moieties having α- and / or L-stereochemistry:

[0103]

[0104] As used herein, a "glucuronyl moiety" is a monovalent moiety in which a hydroxyl group of glucuronic acid is replaced by a bond, functional group, or moiety that is linked to another atom. Unless otherwise specified, glucuronic acid can have any suitable stereochemistry. Thus, the term includes moieties having D-stereochemistry as well as moieties having L-stereochemistry. In addition, the term includes moieties having α-stereochemistry as well as moieties having β-stereochemistry. The carbon atoms of the glucuronyl moiety follow the conventional numbering as shown below. This figure shows β-D-glucuronic acid, but applies in a similar manner to glucuronyl moieties having α- and / or L-stereochemistry:

[0105]

[0106] The term "C 1-6"Alkyl glucuronate moiety" means a glucuronate moiety (as defined in this paragraph) in which the carboxylic acid group of glucuronic acid has a C 1-6 alkyl group substituting for a hydrogen atom in the carboxylic acid group. In any of the following embodiments, the C 1-6 alkyl moiety can have any suitable value, such as methyl, ethyl, isopropyl, propyl, butyl, pentyl, etc. In some embodiments, the C 1-6 alkyl moiety is methyl. In some other embodiments, the C 1-6 alkyl moiety is ethyl.

[0107] As used herein, a substituted group is derived from an unsubstituted parent group in which one or more hydrogen atoms have been exchanged for another atom or group. Unless otherwise specified, when a group is considered to be "substituted with" or "substituted by", it means that the group is substituted with one or more substituents independently selected from C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkynyl, C 1 -C 6 heteroalkyl, C 3 -C 7 carbocyclic group (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), C 3 -C 7 -carbocyclic group-C 1 -C 6 -alkyl (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 3- to 10-membered heterocyclic group (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6(haloalkoxy), 3- to 10-membered heterocycle-C 1 -C 6 -alkyl (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), aryl (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), aryl(C 1 -C 6 )alkyl (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 5- to 10-membered heteroaryl (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 5- to 10-membered heteroaryl(C 1 -C 6 )alkyl (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), halogen, cyano, hydroxy, C 1 -C 6 alkoxy, C 1 -C 6 alkoxy(C 1 -C 6 )alkyl (i.e., ether), aryloxy (optionally substituted with halogen, C 1 -C6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), C 3 -C 7 carbon epoxy group (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 3- to 10-membered heteroepoxy group (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 5- to 10-membered heteroaryloxy group (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), C 3 -C 7 -carbocyclic group -C 1 -C 6 alkoxy (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 3- to 10-membered heterocyclic group -C 1 -C 6 -alkoxy (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6(haloalkoxy), aryl(C 1 -C 6 )alkoxy(optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 5- to 10-membered heteroaryl(C 1 -C 6 )alkoxy(optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), mercapto, halo(C 1 -C 6 )alkyl(e.g. -CF 3 ), halo(C 1 -C 6 )alkoxy(e.g. -OCF 3 ), C 1 -C 6 alkylthio, arylthio(optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), C 3 -C 7 carbocyclicthio(optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 3- to 10-membered heterocyclic-sulfanyl(optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C6 (haloalkoxy), 5- to 10-membered heteroaryl-thio (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), C 3 -C 7 -carbocyclic-C 1 -C 6 -alkylthio (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 3- to 10-membered heterocyclic-C 1 -C 6 alkylthio (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), aryl(C 1 -C 6 )alkylthio (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), 5- to 10-membered heteroaryl(C 1 -C 6 )alkylthio (optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy), amino, amino(C 1 -C 6)Alkyl, nitro, O-carbamoyl, N-carbamoyl, O-thiocarbamoyl, N-thiocarbamoyl, C-amido, N-amido, S-sulfonamido, N-sulfonamido, C-carboxy, O-carboxy, acyl, cyanate, isocyanate, thiocyanate, isothiocyanate, sulfinyl, sulfonyl, and oxo(=O). In cases where a group is described as "optionally substituted with", the group may be substituted with the above substituents.

[0108] It should be understood that, depending on the context, certain radical naming conventions may include monoradicals or diradicals. For example, when a substituent is required to have two attachment points to the rest of the molecule, it should be understood that the substituent is a diradical. For example, substituents of an alkyl group that are recognized as requiring two attachment points include diradicals such as -CH 2 -, -CH 2 CH 2 -, -CH 2 CH(CH 3 )CH 2 -, etc. Other radical naming conventions clearly indicate that the radical is a diradical, such as "alkylene" or "alkenylene". Whenever a substituent is described as a diradical (i.e., having two attachment points to the rest of the molecule), it should be understood that, unless otherwise specified, the substituent can be attached in any orientational configuration. Thus, for example, a substituent represented as -AE- or includes substituents in which A is attached at the leftmost attachment point of the molecule as well as cases where A is attached at the rightmost attachment point of the molecule.

[0109] As used herein, certain monovalent or polyvalent groups having only a single atom may be referred to by the name of the atom. For example, in certain cases, the substituent "-H" may be referred to as "hydrogen" or "hydrogen atom", or the substituent "-F" may be referred to as "fluorine" or "fluorine atom", while the linking group "-O-" may be referred to as "oxygen" or "oxygen atom".

[0110] The attachment points of a group are typically represented by a dash (-) or an asterisk (*). For example, groups such as *-CH 2 -CH 3 or -CH 2 -CH 3 all represent an ethyl group.

[0111] Chemical structures are typically shown in "skeletal" format, so carbon atoms are not explicitly shown and hydrogen atoms attached to carbon atoms are completely omitted. For example, the structure represents butane (i.e., n-butane). In addition, aromatic groups such as benzene are represented by showing one of the contributing resonance structures. For example, the structure represents toluene.

[0112] 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.

[0113] As used herein, "or" will 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 without B, or B may be present without A, or both A and B may be present. Further, for example, if A defines a class that can have multiple members (e.g., A 1 and A 2 ), one or more members of the class may be present simultaneously.

[0114] As used herein, "for example," "such as," "like," or "including" are intended to introduce examples that further illustrate a more general subject. Unless otherwise explicitly stated, providing such examples is merely to aid in understanding the embodiments shown in the present disclosure and is not meant to be limiting in any way. These phrases also do not indicate any kind of preference for the disclosed embodiments.

[0115] In a first aspect, the present invention relates to a liquid composition comprising:

[0116] a) a compound of formula (I)

[0117]

[0118] or a salt thereof, wherein:

[0119] R 1 is a hydrogen atom, -OH or -O-R 1A ;

[0120] R 1A is C 1-6 alkyl, optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 1A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0121] R 2 is a hydrogen atom, -OH or -O-R 2A ;

[0122] R 2A is C 1-6 alkyl, optionally substituted one or more times with substituents selected from -OH and C 1-6The substituent of the alkoxy group is substituted one or more times, or R 2A is a glucuronyl moiety, a furanosyl moiety, a pyranosyl moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanosyl moieties and pyranosyl moieties;

[0123] R 3 is -OH or -O-R 3A ;

[0124] R 3A is C 1-6 alkyl, which is optionally substituted one or more times by a substituent selected from -OH and C 1-6 alkoxy; or R 3A is a glucuronyl moiety, a furanosyl moiety, a pyranosyl moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanosyl moieties and pyranosyl moieties;

[0125] R 4 is a hydrogen atom, -OH or -O-R 4A ;

[0126] R 4A is C 1-6 alkyl, which is optionally substituted one or more times by a substituent selected from -OH and C 1-6 alkoxy; or R 4A is a glucuronyl moiety, a furanosyl moiety, a pyranosyl moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanosyl moieties and pyranosyl moieties;

[0127] R 5 is a hydrogen atom, -OH, -O-R 5A or -OC(O)-R 5B ;

[0128] R 5A is C 1-6 alkyl, which is optionally substituted one or more times by a substituent selected from -OH and C 1-6 alkoxy; or R 5A is a glucuronyl moiety, a furanosyl moiety, a pyranosyl moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanosyl moieties and pyranosyl moieties;

[0129] R 5B is -H or C 1-6 alkyl, which is optionally substituted one or more times by a substituent selected from -OH and C 1-6 alkoxy;

[0130] R 6 and R7 independently selected from C 1-6 alkyl, -OH, C 1-6 alkoxy, and -O-(C 1-6 alkylene)-O-(C 1-6 alkyl);

[0131] m is 0, 1, or 2; and

[0132] n is 0, 1, 2, or 3;

[0133] or

[0134] a compound of formula (II)

[0135]

[0136] or a salt thereof, wherein:

[0137] R 8 is a hydrogen atom, -OH, or -O-R 8A ;

[0138] R 8A is C 1-6 alkyl, which may optionally be substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 8A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety, or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0139] R 9 is a hydrogen atom, -OH, or -O-R 9A ;

[0140] R 9A is C 1-6 alkyl, which may optionally be substituted one or more times with substituents selected from -OH and C 1-6 alkoxy, or R 9A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety, or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties;

[0141] R 10 is -OH or -O-R 10A ;

[0142] R 10A is C 1-6 alkyl, which may optionally be substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 10Ais a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from a furanose moiety and a pyranose moiety;

[0143] R 11 is a hydrogen atom, -OH or -O-R 11A ;

[0144] R 11A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 11A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from a furanose moiety and a pyranose moiety;

[0145] R 12 is a hydrogen atom, -OH, -O-R 12A or -OC(O)-R 12B ;

[0146] R 12A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 12A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from a furanose moiety and a pyranose moiety;

[0147] R 12B is -H or C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy;

[0148] R 13 and R 14 are independently selected from C 1-6 alkyl, -OH, C 1-6 alkoxy and -O-(C 1-6 alkylene)-O-(C 1-6 alkyl);

[0149] m' is 0, 1 or 2; and

[0150] n' is 0, 1, 2 or 3; or a combination thereof;

[0151] b) an oil containing carvone; and

[0152] c) an optionally used solvent.

[0153] In some embodiments, the liquid composition comprises a compound of formula (I). The compound of formula (I) is a flavanone or flavanone derivative within the compound class of flavonoids. The compound of formula (I) can be used as a taste-modifying compound, such as a cooling-enhancing compound, a sweetness-enhancing compound, a bitterness-blocking compound, etc.

[0154] In one embodiment, R 5 is a hydrogen atom, -OH or -OC(O)-R 5B , typically where R 5B is C 1-6 alkyl, typically methyl.

[0155] In another embodiment, R 1 is -OH or -O-R 1A , R 2 is -OH or -O-R 2A , R 3 is -OH or -O-R 3A , R 4 is -OH or -O-R 4A , m is 0, and n is 0.

[0156] Exemplary compounds of formula (I) suitable for use according to the present disclosure include, but are not limited to, hesperetin, naringenin, eriodyctiol, homoeriodyctiol, 7-O-methyleriodyctiol (sterubin), aromadendrin, aromadendrin-3-O-acetate, or any salt or glycoside thereof.

[0157] Other exemplary compounds of formula (I) suitable for use according to the present invention include, but are not limited to, naringin, hesperidin, (2R,3R)-3-acetoxy-5,7,4'-trihydroxyflavanone, (2R,3R)-3-acetoxy-5,7,3'-trihydroxy-4'-methoxyflavanone, 3-methoxy-5,3'-dihydroxy-4'-methoxyflavanone (racemic), nobiletin, polymethoxyflavones, mixed methoxy and hydroxyflavones, quercetin, 7-methylhesperetin (persicogenin), or any salt or glycoside thereof.

[0158] In one embodiment, the liquid composition comprises a compound of formula (II). The compound of formula (II) is a dihydrochalcone or dihydrochalcone derivative within the compound class of flavonoids. The compound of formula (II) can be used as a taste-modifying compound, such as a cooling-enhancing compound, a sweetness-enhancing compound, a bitterness-blocking compound, etc.

[0159] In one embodiment, R 12 is a hydrogen atom.

[0160] In another embodiment, R 8 is -OH or -O-R 8A , R 9 is -OH or -O-R 9A , R 10 is -OH or -O-R 10A , R 11 is -OH or -O-R 11A , m' is 0, and n' is 0.

[0161] Non-limiting examples of the compounds of formula (II) include, but are not limited to, naringin dihydrochalcone, hesperetin dihydrochalcone, hesperetin dihydrochalcone 4'-O-glucoside, neohesperidin dihydrochalcone, and phloretin.

[0162] Surprisingly, using an oil containing carvone and optionally a solvent, the compounds of formula (I) and / or formula (II) can be dissolved at high concentrations to provide a clear and homogeneous solution. The term "clear" means that, in the absence of a colorant or fluorescent agent, with deionized water as a reference, the transmittance of the solution for visible light (500 - 800 nm) at an optical path length of 1 cm is 100%. Thus, in one embodiment, the liquid composition is a clear and homogeneous solution.

[0163] In one embodiment, the clear and homogeneous solution is also stable. The term "stable" means that the liquid composition does not undergo phase separation and remains clear, without detectable signs of turbidity, cloudiness, or precipitation, at room temperature or within a specific temperature range (e.g., room temperature ± 10 - 20 °C, typically between 10 °C and 45 °C, more typically between 3 °C and 45 °C) and over a long period of time (typically at least several days, more typically at least several weeks, even more typically at least several months or longer).

[0164] The oil containing carvone can be any source of carvone known to those skilled in the art. Carvone (2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one) is a terpene compound that can be obtained by chemical synthesis or extracted from natural sources using known methods. Carvone has two enantiomeric forms: R-(-)-carvone (also known as levorotatory (L)-carvone) and S-(+)-carvone (also known as dextrorotatory (D)-carvone). The present disclosure contemplates racemic mixtures of carvone and the enantiomers of its resolved forms. The racemic mixture of carvone and the enantiomers of its resolved forms can be pure, i.e., pure or unmixed with other materials, or can be part of a mixture such as an extract. In one embodiment, the oil containing carvone is pure carvone, spearmint oil, caraway seed oil, or dill oil. Spearmint oil is commercially available as an extract of Mentha Spicata with a certain amount of carvone, for example, Mentha Spicata with 60% carvone and Mentha Spicata China with 80% carvone, etc. In some embodiments, the oil containing carvone is food grade.

[0165] In some embodiments, the optionally used solvent can include one or more solvents commonly used in the flavor or fragrance industry, provided that the one or more solvents do not have a negative impact on the transparency and uniformity of the liquid composition. In one embodiment, the optionally used solvent includes one or more solvents selected from the group consisting of 1-propanol (n-propanol), 2-propanol (isopropanol), ethanol, 1,2-propanediol (propylene glycol), triethyl citrate, triacetin, glycerol, 1,3-propanediol, ethyl lactate, and benzyl alcohol.

[0166] The weight ratio of the amount of the oil of carvone to the amount of the optionally used solvent (if present) is not particularly limited. However, in some embodiments, the weight ratio of the amount of the oil containing carvone to the amount of the optionally used solvent (if present) is from 1:99 to 99:1, typically from 10:90 to 90:10, more typically from 30:70 to 90:10. In some embodiments, the weight ratio of the amount of the oil containing carvone to the amount of the optionally used solvent (if present) is 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, or 90:10.

[0167] In one embodiment, the liquid composition comprises the carvone-containing oil and one or more solvents selected from the group consisting of 1-propanol (n-propanol), 2-propanol (isopropanol), ethanol, 1,2-propanediol, triethyl citrate, glyceryl triacetate, glycerol, 1,3-propanediol, ethyl lactate, and benzyl alcohol. In one embodiment, the liquid composition comprises the carvone-containing oil and two solvents selected from the group consisting of 1-propanol (n-propanol), 2-propanol (isopropanol), ethanol, 1,2-propanediol, triethyl citrate, glyceryl triacetate, glycerol, 1,3-propanediol, ethyl lactate, and benzyl alcohol.

[0168] As described herein, the compounds of formula (I) and / or formula (II) can be dissolved at high concentrations. In one embodiment, the amount of the compound of formula (I) and / or formula (II) present is at least 6%, typically at least 10%, more typically at least 15% by weight of the total weight of the composition. In some embodiments, the amount of the compound of formula (I) and / or formula (II) present is 6% to 50%, typically 10% to 40%, more typically 15% to 30% by weight of the total weight of the liquid composition.

[0169] In some embodiments, the amount of the compound of formula (I) and / or (II) present is at least 7%, at least 7.5%, at least 8%, at least 8.5%, at least 9%, at least 9.5%, at least 10%, at least 10.5% or at least 11% by weight relative to the total weight of the composition.

[0170] In some embodiments, the amount of the compound of formula (I) and / or (II) is from 7% to 50% by weight, typically from 7% to 40% by weight, more typically from 7% to 30% by weight, even more typically from 7% to 25% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is from 7.5% to 50% by weight, typically from 7.5% to 40% by weight, more typically from 7.5% to 30% by weight, even more typically from 7.5% to 25% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is from 8% to 50% by weight, typically from 8% to 40% by weight, more typically from 8% to 30% by weight, even more typically from 8% to 25% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is from 8.5% to 50% by weight, typically from 8.5% to 40% by weight, more typically from 8.5% to 30% by weight, even more typically from 8.5% to 25% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is from 9% to 50% by weight, typically from 9% to 40% by weight, more typically from 9% to 30% by weight, even more typically from 9% to 25% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is from 9.5% to 50% by weight, typically from 9.5% to 40% by weight, more typically from 9.5% to 30% by weight, even more typically from 9.5% to 25% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is from 10% to 50% by weight, typically from 10% to 40% by weight, more typically from 10% to 30% by weight, even more typically from 10% to 25% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is from 10.5% to 50% by weight, typically from 10.5% to 40% by weight, more typically from 10.5% to 30% by weight, even more typically from 10.5% to 25% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is from 11% to 50% by weight, typically from 11% to 40% by weight, more typically from 11% to 30% by weight, still more typically from 11% to 25% by weight of the total weight of the liquid composition.

[0171] In some embodiments, the amount of the compound of formula (I) and / or (II) is 7% to 25%, 7% to 24%, 7% to 23%, 7% to 22%, 7% to 21%, or 7% to 20% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is 7.5% to 25%, 7.5% to 24%, 7.5% to 23%, 7.5% to 22%, 7.5% to 21%, or 7.5% to 20% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is 8% to 25%, 8% to 24%, 8% to 23%, 8% to 22%, 8% to 21%, or 8% to 20% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is 8.5% to 25%, 8.5% to 24%, 8.5% to 23%, 8.5% to 22%, 8.5% to 21%, or 8.5% to 20% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is 9% to 25%, 9% to 24%, 9% to 23%, 9% to 22%, 9% to 21%, or 9% to 20% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is 9.5% to 25%, 9.5% to 24%, 9.5% to 23%, 9.5% to 22%, 9.5% to 21%, or 9.5% to 20% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is 10% to 25%, 10% to 24%, 10% to 23%, 10% to 22%, 10% to 21%, or 10% to 20% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is 10.5% to 25%, 10.5% to 24%, 10.5% to 23%, 10.5% to 22%, 10.5% to 21% or 10.5% to 20% by weight of the total weight of the liquid composition. In some embodiments, the amount of the compound of formula (I) and / or (II) is 11% to 25%, 11% to 24%, 11% to 23%, 11% to 22%, 11% to 21%, or 11% to 20% by weight of the total weight of the liquid composition.

[0172] In some embodiments, the amount of the compound of formula (I) and / or (II) is 7% to 11% by weight of the total weight of the liquid composition, typically 7% to 10%, more typically 7% to 9%.

[0173] In a second aspect, the present disclosure relates to a consumer product comprising the liquid composition described herein.

[0174] Consumer products may contain cooling compounds. "Cooling compounds" refer to compounds that modulate the TRPM8 receptor.

[0175] Exemplary cooling compounds include, but are not limited to, compounds selected from the group consisting of: (-)-menthol, N-ethyl-p-menthane-3-carboxamide, cubeb alcohol, isopulegol, 3-(L-menthoxy)propane-1,2-diol, cis / trans-p-menthane-3,8-diol, 3-(L-menthoxy)-2-methylpropane-1,2-diol, 2-[2-(p-menthan-3-yloxy)ethoxy]ethanol, menthoxyethanol, (1R,2R,4R)-1-(2-hydroxy-4-methylcyclohexyl)ethenone, (1R,2R,5R)-N-ethyl-5-methyl-2-(prop-1-en-2-yl)cyclohexanecarboxamide, N-(3-hydroxy-4-methoxyphenyl)-2-isopropyl-5,5-dimethylcyclohexanecarboxamide, N-[4-(cyanomethyl)phenyl]-2-isopropyl-5,5-dimethylcyclohexanecarboxamide, N-(2-hydroxy-2-phenylethyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide, L-menthyl lactate, (-)-menthyl glycol carbonate, (-)-menthone 1,2-glycerol ketal, D / L-menthone 1,2-glycerol ketal, (-)-menthyl 1-propylene glycol carbonate, (-)-menthyl 2-propylene glycol carbonate, D / L-menthyl 1-propylene glycol carbonate, D / L-menthyl 2-propylene glycol carbonate, (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide, menthyl ethylamide oxalate, (E)-3-benzo[1,3]dioxol-5-yl-N,N-diphenyl-2-propenamide, 3,4-methylenedioxycinnamic acid, N,N-diphenylamide, N,N-dimethyl(-)-menthyl succinimide, (1R,2S,5R)-N-(4-(carbamoylmethyl)phenyl)-menthylcarboxamide, (-)-menthyl pyrrolidonecarboxylate, L-desoxyephedrine p-menthane carboxamide, (1R,2S,5R)-N-(4-(cyanomethyl)phenyl)menthylcarboxamide, (1R,2S,5R)-N-(2-(pyridin-2-yl)ethyl)menthylcarboxamide, 6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]Decan-2-one, (1R,2R,4S)-dihydrodipenteneol, N-ethyl-p-menthane-3-carboxamide, 2-isopropyl-N,2,3-trimethylbutanamide, ethyl 3-(p-menthane-3-carboxamido)acetate, N-ethyl-2,2-diisopropylbutanamide, N-(1,1-dimethyl-2-hydroxyethyl)-2,2-dimethylbutanamide, N-cyclopropyl-5-methyl-2-isopropyl-cyclohexanecarboxamide, (-)-menthyl acetoacetate, (-)-menthyl succinate, (-)-menthyl (S)-3-hydroxybutyrate, (-)-menthyl glutarate, 1-[2-hydroxyphenyl]-4-[2-nitrophenyl]-1,2,3,6-tetrahydropyrimidin-2-one, di-(-)-menthyl glutarate, N-(2-hydroxyethyl)-2,3-dimethyl-2-isopropylbutanamide, and any combination thereof.

[0176] In some embodiments, the cooling compound can be the cooling compound described in WO 2021 / 074281. For example, (2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)(1,2,3-thiadiazol-5-yl)methanone, (2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)(thietan-3-yl)methanone, (2,2-dimethylcyclopropyl)(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)methanone, (2-ethoxycyclopropyl)(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)methanone, (2-methoxycyclopropyl)(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)methanone, (2-methylcyclopropyl)(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)methanone, (2S)-2-methyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, (5-methyltetrahydrofuran-3-yl)(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)methanone, (E)-1-(2-(5-(3,4-difluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbut-2-en-1-one, (E)-2-methyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)but-2-en-1-one, (E)-2-methyl-1-(2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)pent-3-en-1-one, (R)-2-(methylthio)-1-((R)-2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, (S)-2-(methylthio)-1-((R)-2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, (S)-2-(methylthio)-1-((S)-2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, (S)-2-methyl-1-((R)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, (tetrahydrofuran-3-yl)(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)methanone, 1-(2-(1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one,1-(2-(4-(2,3-dihydrobenzofuran-5-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(2,3-dihydrobenzofuran-6-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(2,5-dimethylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(2-chlorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(2-cyclopropyl-1,3-oxazol-5-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(2-fluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(2-hydroxyphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(3-((dimethylamino)methyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(3,5-difluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(3,5-dimethylisoxazol-4-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(3-chloro-4-methylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(3-methylfuran-2-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(4-((1,1-dioxothiomorpholino)methyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(4-(1-hydroxyethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(4-(difluoromethoxy)-3-fluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(4-(difluoromethyl)thiophen-3-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(4-(methylsulfonyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(4-(tert-butyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one1-(2-(4-(4-Cyclobutylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(4-Cyclopropyl-2-fluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(4-Fluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(4-Hydroxyphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(4-Isopropylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(4-Methyl-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(5-((Dimethylamino)methyl)thiophen-2-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(5-Methylfuran-2-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(5-Methylpyridin-3-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(6-Methylpyridin-3-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-(Benzo[b]thiophen-6-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-Methyl-5-phenyl-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(4-Phenyl-1H-imidazol-2-yl)piperidin-1-yl)-2-((trifluoromethyl)thio)ethan-1-one, 1-(2-(4-Phenyl-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 1-(2-(4-Phenyl-1H-imidazol-2-yl)piperidin-1-yl)hexa-3,5-dien-1-one, 1-(2-(4-Phenyl-1H-imidazol-2-yl)piperidin-1-yl)penta-4-en-1-one, 1-(2-(4-Phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 1-(2-(5-(2,3-Difluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(2,4-Difluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(2,5-Difluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one,1-(2-(5-(2-Fluoro-4-methoxyphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(2-Fluoro-4-methylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(2-Methoxypyrimidin-5-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(3-(Methylamino)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(3,4-Difluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(3,4-Difluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbut-3-en-1-one, 1-(2-(5-(3,4-Dimethoxyphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(3,4-Dimethylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(3-Fluoro-4-(methoxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(3-Fluoro-4-methylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(3-Fluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(3-Methoxyisothiazol-4-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(3-Methoxyphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-((Methylamino)methyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-(2-Methoxyethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-(Aminomethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-(Dimethylamino)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-(Hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-Acetylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one1-(2-(5-(4-Aminophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-chloro-3-fluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-chlorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-ethylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-fluorophenyl)-4H-1,2,4-triazol-3-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-methoxy-2-methylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-methoxyphenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(4-methyl-6-(methylthio)pyridin-3-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(5-(methoxymethyl)thiophen-3-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(6-methoxypyridin-3-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(benzo[d][1,3]dioxol-5-yl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 1-(2-(5-benzyl-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-(5-bromo-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 2-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-5-yl)benzonitrile, 2-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-carbonyl)cyclopropane-1-carbonitrile, 2-(5-methylfuran-2-yl)-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(allylthio)-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(dimethylamino)-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 2-(dimethylamino)-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one2-(ethylthio)-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(furan-2-yl)-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)ethan-1-one, 2-(furan-2-yl)-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(furan-3-yl)-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)ethan-1-one, 2-(furan-3-yl)-1-(2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylamino)-N-(4-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-5-yl)phenyl)acetamide, 2-(methylsulfinyl)-1-(2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylsulfonyl)-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)ethan-1-one, 2-(methylsulfonyl)-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(2-(p-tolyl)-2H-tetrazol-5-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(1-(trifluoromethyl)-1H-pyrazol-4-yl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(4-(morpholinomethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(5-(trifluoromethyl)furan-2-yl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(5-(trifluoromethyl)thiophen-2-yl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(5-methylthiophen-3-yl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(m-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(o-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(pyridin-3-yl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(pyridin-4-yl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one,2-(methylthio)-1-(2-(4-(pyrimidin-5-yl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(quinoxalin-6-yl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(thiophen-3-yl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)ethan-1-one, 2-(methylthio)-1-(2-(5-(2-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(2,3,4-trifluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(2,4,5-trifluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(4-propylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(4-vinylphenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(5-methylthiophen-2-yl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(p-tolyl)-1,3,4-oxadiazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)azepan-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(p-tolyl)-4H-1,2,4-triazol-3-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(p-tolyl)isoxazol-3-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(p-tolyl)oxazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-(p-tolyl)thiazol-2-yl)piperidin-1-yl)propan-1-one,2-(methylthio)-1-(2-(5-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-phenyl-1H-imidazol-2-yl)pyrrolidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-phenyl-4H-1,2,4-triazol-3-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(5-phenyloxazol-2-yl)piperidin-1-yl)propan-1-one, 2-(methylthio)-1-(4-(5-(p-tolyl)-1H-imidazol-2-yl)thiazolidin-3-yl)propan-1-one, 2,2,3-trimethyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)but-3-en-1-one, 2,2,3-trimethyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 2,2-dimethyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)but-3-en-1-one, 2,2-dimethyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 2,3-dimethoxy-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2,3-dimethyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 2,5-difluoro-4-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-4-yl)benzonitrile, 2-amino-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-cyclobutyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-cyclopentyl-2-ethoxy-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)ethan-1-one, 2-cyclopropyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)ethan-1-one, 2-cyclopropyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-cyclopropyl-2-methoxy-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)ethan-1-one, 2-ethoxy-1-(2-(5-(3-fluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-ethyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)but-2-en-1-one, 2-ethyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 2-fluoro-4-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-5-yl)benzonitrile2-Mercapto-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-methoxy-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 2-methoxy-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-methoxy-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-methyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 2-methyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-methyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)but-3-en-1-one, 2-methyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 2-methyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)butane-1,3-dione, 2-methyl-1-(2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)pentan-1-one, 2-methyl-1-(2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)prop-2-en-1-one, 2-methyl-1-(2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-methyl-2-(methylthio)-1-(2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-methyl-3-(methylthio)-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-methylene-1-(2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 3-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-4-yl)benzonitrile, 3,3,3-trifluoro-2-methyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 3,3,4,4,4-pentafluoro-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 3,3-difluoro-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 3-fluoro-4-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-5-yl)benzonitrile, 3-methyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)but-2-en-1-one, 3-methyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 4-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-4-yl)benzonitrile,4-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-5-yl)benzaldehyde, 4,4,4-trifluoro-2-methyl-1-(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, bicyclo[1.1.1]pent-1-yl(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)methanone, cyclobutyl(2-(5-(3-fluorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)methanone, cyclopentyl(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)methanone, cyclopropyl(2-(4-phenyl-1H-imidazol-2-yl)piperidin-1-yl)methanone, methyl 4-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-5-yl)benzoate, N-(2-hydroxyethyl)-4-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-4-yl)benzenesulfonamide, 2-(methylthio)-1-(2-(5-(3-nitrophenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, N-(4-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-4-yl)phenyl)methanesulfonamide, 2-(methylthio)-1-(2-(5-(4-nitrophenyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 1-(sec-butylsulfinyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-(sec-butylsulfonyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-(isopropylsulfinyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-(isopropylsulfonyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-((1-(methylthio)ethyl)sulfinyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-((1-(methylthio)ethyl)sulfonyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-((2-(methylthio)propan-2-yl)sulfinyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-((2-(methylthio)propan-2-yl)sulfonyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-(but-3-en-2-ylsulfinyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-(but-3-en-2-ylsulfonyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-(pent-3-en-2-ylsulfinyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-(pent-3-en-2-ylsulfonyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine1-((2-Methylbut-3-en-2-yl)sulfinyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-((2-Methylbut-3-en-2-yl)sulfonyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-(2-(5-(4-(Hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 2-(Methylsulfonyl)-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 1-(4-Hydroxy-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(5-Hydroxy-2-(5-p-tolyl-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(4-Hydroxy-2-(5-p-tolyl-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 1-(5-Hydroxy-2-(5-p-tolyl-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 1-(2-(5-(4-Hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylsulfonyl)propan-1-one, 1-(4-Hydroxy-2-(5-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylsulfonyl)propan-1-one, 1-(5-Hydroxy-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylsulfonyl)propan-1-one, 1-(2-Hydroxy-6-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-Hydroxy-6-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 1-(2-Hydroxy-6-(5-p-tolyl-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylsulfonyl)propan-1-one, 1-(3-Hydroxy-2-(5-p-tolyl-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(3-Hydroxy-2-(5-p-tolyl-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 1-(3-Hydroxy-2-(5-p-tolyl-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylsulfonyl)propan-1-one, 1-(2-(5-(4-(Hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylsulfinyl)propan-1-one, 1-(4-Hydroxy-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylsulfinyl)propan-1-one, 1-(5-Hydroxy-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylsulfinyl)propan-1-one1-(2-Hydroxy-6-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylsulfinyl)propan-1-one, 1-(3-Hydroxy-2-(5-p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylsulfinyl)propan-1-one, 1-(2-Hydroxy-6-(5-(4-hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(5-Hydroxy-2-(5-(4-hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(4-Hydroxy-2-(5-(4-hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(3-Hydroxy-2-(5-(4-(hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-(methylthio)propan-1-one, 1-(2-Hydroxy-6-(5-(4-(hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 1-(5-Hydroxy-2-(5-(4-(hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 1-(4-Hydroxy-2-(5-(4-(hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 1-(3-Hydroxy-2-(5-(4-(hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 4-(2-(1-(2-Methylbutanoyl)piperidin-2-yl)-1H-imidazol-5-yl)benzaldehyde, 4-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-5-yl)benzoic acid, 4-(2-(1-(2-Methylbutanoyl)piperidin-2-yl)-1H-imidazol-5-yl)benzoic acid, (2,2-Dimethylcyclopropyl)(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)methanone, 1-(2-(5-Bromo-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 1-(2-(5-(4-Chlorophenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 2-(4-(2-(1-(2-(methylthio)propanoyl)piperidin-2-yl)-1H-imidazol-5-yl)phenyl)acetonitrile, 2-(4-(2-(1-(2-Methylbutanoyl)piperidin-2-yl)-1H-imidazol-5-yl)phenyl)acetonitrile, 2-(4-(2-(1-(2-Methylbutanoyl)piperidin-2-yl)-1H-imidazol-5-yl)phenyl)acetonitrile, 2,3-Dimethyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one2-Methyl-1-(2-(5-(o-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 2-methyl-1-(2-(5-(m-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 1-(2-(5-(4-(hydroxymethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-2-methylbutan-1-one, 1-(isopropylsulfonyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 1-(sec-butylsulfonyl)-2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine, 2-methyl-1-(2-(5-(5-methylthiophen-2-yl)-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 2-(methylthio)-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperazin-1-yl)propan-1-one, 2-(methylthio)-1-(2-(4-(p-tolyl)oxazol-2-yl)piperidin-1-yl)propan-1-one, 2-methyl-1-(2-(4-(p-tolyl)oxazol-2-yl)piperidin-1-yl)butan-1-one, their derivatives (such as those described in WO 2022 / 170519), or any combination thereof.

[0177] In some embodiments, the cooling compound can be 2-methyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)butan-1-one, 2-(methylthio)-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2-methyl-2-(methylthio)-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)propan-1-one, 2,2-dimethyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)but-3-en-1-one, or a combination thereof.

[0178] In some embodiments, the cooling compound can be 1-isopropyl-3,3,5,7-tetramethyloctahydrobenzo[c]isoxazole, 5-(4-fluorophenyl)-1,3,3,5,7-pentamethyloctahydrobenzo[c]isoxazole (including (3aR,5R,7S,7aR)-5-(4-fluorophenyl)-1,3,3,5,7-pentamethyloctahydrobenzo[c]isoxazole, (3aR,5R,7R,7aR)-5-(4-fluorophenyl)-1,3,3,5,7-pentamethyloctahydrobenzo[c]isoxazole, (3aR,5R,7S,7aS)-5-(4-fluorophenyl)-1,3,3,5,7-pentamethyloctahydrobenzo[c]isoxazole, or any combination thereof.

[0179] Consumer products can include cooling enhancing compounds. As used herein, a "cooling enhancing compound" is capable of enhancing the cooling sensation provided by a consumer product containing a cooling compound, but can also provide a cooling sensation alone. Such cooling enhancing compounds include, but are not limited to, naturally derived compounds 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. Exemplary cooling enhancing compounds include, but are not limited to, compounds selected from the group consisting of: N-ethyl-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide; N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide; 2-(4-fluorophenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide; 2-(2-hydroxy-4-methylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide; 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide; 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiazol-5-ylmethyl)acetamide; 5-methoxy-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)benzofuran-2-carboxamide; 2-(4-ethylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide; (E / Z)-2-methyl-2-butenal; (E / Z)-2-isopropyl-5-methyl-2-hexenal; their derivatives such as those described in WO 2022 / 170519, and any combination thereof.

[0180] Consumer products can be flavored products, typically food products, beverage products, oral care products, or pharmaceutical products.

[0181] Flavored products can include sweeteners. As used herein, a "sweetener" refers to a compound or its ingestion-acceptable salt that can produce a perceptible sweet taste in a subject, such as a compound that activates the T1R2 / T1R3 receptor in vitro. Sweeteners can include low-calorie, zero-calorie, or high-intensity sweeteners. The term "high-intensity sweetener" refers to a sweetener that is sweeter than sucrose, such as at least 10 times sweeter, or at least 20 times sweeter, or at least 50 times sweeter, or at least 100 times sweeter, or at least 250 times sweeter, or at least 500 times sweeter, or at least 750 times sweeter, or at least 1000 times sweeter, or at least 2500 times sweeter, or at least 5000 times sweeter, or at least 7500 times sweeter, or at least 10000 times sweeter than sucrose. In this context, saying that a sweetener is x times sweeter than sucrose means that at a concentration relative to 1 / x of the weight of sucrose in an aqueous solution of the sweetener, it produces a sweetness equivalent to that of sucrose.

[0182] Examples of suitable sweeteners are set forth in more detail below. In some embodiments, the sweetener is sucralose, which refers to 1,6-dichloro-1,6-dideoxy-β-D-fructofuranosyl-4-chloro-4-deoxy-α-D-galactopyranoside. In some embodiments, the sweetener is sodium saccharin. Sodium saccharin can be present at any suitable concentration. In some embodiments, the concentration of sodium saccharin ranges from 10 ppm to 10,000 ppm, or 50 ppm to 5,000 ppm, or 100 ppm to 3,000 ppm.

[0183] In some embodiments, the sweetener may comprise glucosylated natural steviol glycosides. As used herein, the term "natural steviol glycoside" refers to steviol glycosides that occur naturally in the plant species Stevia rebaudiana, Stevia phlebophylla, or Rubus chingii. Such compounds are glycosides of the diterpene steviol. Some non-limiting examples include stevioside, rebaudioside A, rebaudioside C, dulcoside A, etc. As used herein, the term "glucosylated natural steviol glycoside" refers to a compound obtained by enzymatic glucosylation of a natural steviol glycoside to increase the degree of glucosylation. As used herein, the term "GSG" may be used interchangeably with "glucosylated natural steviol glycoside".

[0184] In embodiments where GSG is present, any suitable GSG can be used. Thus, the GSG can have any suitable degree of additional glucosylation, as well as a suitable type of glucosylation. In some embodiments, the GSG used in the coolness-modifying composition has a degree of glucosylation of at least 1.0, which means that at least one mole of glucose has been added enzymatically to the natural steviol glycoside per mole of the natural steviol glycoside. In some other embodiments, the GSG used in the coolness-modifying composition has a degree of glucosylation of at least 1.1, or at least 1.2, or at least 1.3, or at least 1.4, or at least 1.5, or at least 1.6, or at least 1.7, or at least 1.8, or at least 1.9, or at least 2.0, or at least 2.1, or at least 2.2, or at least 2.3, or at least 2.4, or at least 2.5. The glucosylation can be of any suitable type. For example, in some embodiments, the glucose added enzymatically to the natural steviol glycoside is α-glucose, β-glucose, or a combination thereof. In some embodiments, the glucose added enzymatically to the natural steviol glycoside is α-glucose. In some embodiments, the glucose added enzymatically to the natural steviol glycoside is β-glucose. In some embodiments, the glucose added enzymatically to the natural steviol glycoside is a combination of α-glucose and β-glucose. The glucose added by enzymatic glucosylation can be incorporated by any suitable linkage. Generally, the added glucose units are linked to other glucose units already present on the natural steviol glycoside. In some embodiments, the enzymatically added glucose units are added by a 1,6 bond, meaning that the glucose units are added by the 1-position of the added glucose unit and the 6-position of the glucose unit already present on the natural steviol glycoside. In some other embodiments, the enzymatically added glucose units are added by a 1,4 bond. In some other embodiments, the enzymatically added glucose units are added by a 1,2 bond.

[0185] In embodiments where GSG is present, the GSG can be present at any suitable concentration. In some embodiments, the GSG is present in a concentration range of 1 ppm to 100 ppm, or 1 ppm to 50 ppm, or 1 ppm to 30 ppm, or 1 ppm to 20 ppm, or 1 ppm to 10 ppm.

[0186] In some embodiments, the sweetener can include calorific sugars such as sucrose, glucose, fructose (e.g., in the form of high fructose corn syrup), or any combination thereof. In some embodiments, the sweetener includes one or more rebaudiosides (e.g., rebaudioside A, rebaudioside D, rebaudioside E, rebaudioside M, or any combination thereof). Generally, the concentration of rebaudioside (e.g., rebaudioside A) is about 20 to 50 times higher than the concentration of the above-mentioned sucralose. In some embodiments, the coolness modifying composition includes one or more high-intensity artificial sweeteners such as acesulfame potassium, aspartame, cyclamate, neotame, etc. When any such artificial high-intensity sweetener is present in the coolness modifying composition, their concentration will be substantially the same as the concentration described for the above-mentioned sucralose. In some other embodiments, the coolness modifying composition includes one or more low-calorie carbohydrates or sugar alcohols such as allulose, xylitol, erythritol, etc. In some other embodiments, the coolness modifying composition includes mogrosides, such as in the form of monk fruit juice or extract, or as mogroside III, mogroside IV, mogroside V, semenoside I, isomogroside V, mogroside IV E , isomogroside IV E , isomogroside IV, mogroside III E , 11-oxomogroside V, one or more of the 1,6-α isomers of semenoside I, and any combination thereof. Other mogroside compounds that can be used as sweeteners have been described in U.S. Patent Application Publication No. 2017 / 0119032.

[0187] The consumer products of the present disclosure (typically flavored products) may also contain various other sweeteners. Non-limiting examples include D-allulose, L-ribose, D-tagatose, L-glucose, L-fucose, L-arabinose, D-turanose, D-bacteriosucrose, isomaltitol, lactitol, mannitol, sorbitol, maltodextrin, saccharin, alitame, cyclamic acid, tagatose, maltose, galactose, mannose, lactose, D-tryptophan, glycine, maltitol, lactitol, isomaltitol, hydrogenated starch hydrolysates (HSH), chemically modified mogrosides (such as glucosylated mogrosides), carrelame and other guanidine-based sweeteners, honey, Jerusalem artichoke syrup, licorice root, monk fruit (fruit, powder or extract), lucuma (fruit, powder or extract), maple sap (including sap extracted from, for example, Acer saccharum, Acer nigrum, Acer rubrum, Acer saccharinum, Acer platanoides, Acer negundo, Acer macrophyllum, Acer grandidentatum, Acer glabrum, Acer mono), maple syrup, maple sugar, walnut sap (including sap extracted from, for example, Juglans cinerea, Juglans nigra, Juglans ailatifolia, Juglans regia), birch sap (including sap extracted from, for example, Betula papyrifera, Betula alleghaniensis, Betula lenta, Betula nigra, Betula populifolia, Betula pendula), sycamore sap (such as sap extracted from Platanus occidentalis), ironwood sap (such as sap extracted from Ostrya virginiana), unrefined sucrose (mascobado), molasses (such as blackstrap molasses for example), treacle sugar, monatin, monellin, cane sugarsugar) (also known as natural sugar, unrefined cane sugar or sucrose), palm sugar, panela (panocha), piloncillo, rapadura, raw sugar, rice syrup, sorghum, sorghum syrup, tapioca syrup (also known as tapioca starch syrup), thaumatin, yacon root, malt syrup, barley malt syrup, barley malt powder, beet sugar, cane sugar, crystallized fruit juice crystals, caramel, carbitol, carob syrup, castor sugar, hydrogenated starch hydrolates, hydrolyzed canned fruit juice, hydrolyzed starch, invert sugar, anethole, arabinogalactan, concentrated grape juice (arrope), syrup, P-4000, acesulfame potassium (also known as acesulfame-K or ace-K), alitame (also known as aclame), advantame, aspartame, baiyunosdie, neotame, benzamide derivatives, bernadame, canderel (aspartame alias), carrelame and other guanidine-based sweeteners, plant fiber, corn sugar, conjugated sugar, curculin, cyclamate, cyclocaryoside I, demerara, dextran, dextrin, diastatic maltmalt), dulcin, sucrol, valzin, dulcoside A, dulcoside B, emulin, enoxolone, maltodextrin, saccharin, estragole, ethyl maltol, glucin, gluconic acid, glucono delta-lactone, glucosamine, glucuronic acid, glycerol, glycine, glycyphillin, glycyrrhizin, enoxolone monoglucuronide, golden sugar, yellow sugar, golden syrup, granulated sugar, Gynostemma pentaphyllum, hernandulcin, isomerized liquid sugar, jallab, chicory root dietary fiber, kynurenine derivatives (including N'-formyl-kynurenine, N'-acetyl-kynurenine, 6-chloro-kynurenine), galactitol, litse, ligicane, lycasin, N-(4-cyanophenyl)-N-(2,3-methylenedioxybenzyl)guanidine acetic acid (lugduname), guanidine, falernum, mabinlin I, mabinlin II, maltol, crystalline maltitol (maltisorb), maltodextrin, maltotriol, mannosamine, miraculin, mizuame, mogrosides (including, for example, mogroside IV, mogroside V and neomogroside), mukurozioside, nano sugar, naringin dihydrochalcone, neohesperidin dihydrochalcone, nib sugar, black oligosaccharide, norbu, apricot syrup, osladin, pekmez, pentadin, periandrin I, perillaldehyde, perillartine, petphyllum, phenylalanine, phloisosideside I, phloridzin, phyllodulcin, polyglycitol syrup, polypodoside A, pterocaryoside A, pterocaryoside B, rebiana, refined syrup, rub syrup, rubusoside, selligueain A, shugr, gymnemic acid I, siraitia grosvenorii, soybean oligosaccharide, Splenda, SRIoximeV, steviol glycosides, steviolbiosides, stevioside, strogins 1, 2 and 4, sucronic acid, sucrononate, sugars, sodium (suosan), phloridzin, super aspartame, tetrasaccharides, threitol, treacle, trilobtain, tryptophan and derivatives (6-trifluoromethyl-tryptophan, 6-chloro-D-tryptophan), vanillose, heptitol, birch syrup, aspartame-acesulfame, assugrin, and combinations or blends of any two or more thereof.

[0188] In one particular embodiment, the consumer product (typically a flavored product) comprises a sweetener selected from the group consisting of sucrose, fructose, glucose, erythritol, sucralose, xylitol, and any combination thereof.

[0189] In some embodiments, the consumer product (typically a flavored product) may comprise 4-amino-5,6-dimethylthieno[2,3-d]pyrimidin-2(1H)-one or any suitable salt thereof. In some embodiments, the consumer products disclosed herein may comprise the hydrochloride salt of 4-amino-5,6-dimethylthieno[2,3-d]pyrimidin-2(1H)-one.

[0190] In some embodiments of any of the foregoing embodiments, the consumer product (typically a flavored product) may comprise a lactone. Any suitable lactone or combination of lactones may be used. In some embodiments, the lactone comprises a lactone ring having from 3 to 8 members in the ring, such as a 3-membered lactone ring, a 4-membered lactone ring, a 5-membered lactone ring, a 6-membered lactone ring, a 7-membered lactone ring, or an 8-membered lactone ring.

[0191] In some embodiments, the lactone comprises a 5-membered lactone ring having or not having an unsaturated bond (excluding the unsaturation in the oxo substituents on the ring), such as a carbon-carbon double bond. In some embodiments, the lactone comprises a 5-membered lactone ring having at least one unsaturated bond (e.g., one carbon-carbon double bond). Non-limiting examples of lactones comprising a 5-membered lactone ring having at least one unsaturated bond include angelica lactone α, angelica lactone β, mentholactone, 5,5-dimethyl-2(5H)-furanone, 5-ethyl-2(5H)-furanone, 5-pentyl-2(5H)-furanone, 5-hexyl-2(5H)-furanone, 5-pentyl-2(3H)-furanone, 4-methyl-3-pentyl-2(5H)-furanone, and 2(5H)-furanone. In some embodiments, the lactone comprises a 5-membered lactone ring having no unsaturated bonds. Non-limiting examples of such lactones include γ-butyrolactone, γ-valerolactone, γ-caprolactone, γ-enantholactone, γ-octalactone, γ-undecalactone, γ-decalactone, dihydrojasmone lactone, and dihydromenthollactone (3,6-dimethyl-hexahydro-2(3H)-benzofuranone). In some embodiments, the lactone is dihydromenthollactone.

[0192] In some embodiments, the lactone comprises a 6-membered lactone ring having or not having an unsaturated bond. In some embodiments, the lactone comprises a 6-membered lactone ring having at least one unsaturated bond. Non-limiting examples of lactones comprising a 6-membered lactone ring having at least one unsaturated bond include δ-2-decenolide, coumarin, and 6-methylcoumarin. In some other embodiments, the lactone comprises a 6-membered lactone ring having no unsaturated bonds. Non-limiting examples of lactones comprising a 6-membered lactone ring having no unsaturated bonds include δ-decalactone, δ-dodecalactone, and cyclohexyl lactone.

[0193] In certain embodiments, the consumer product may comprise any additional ingredient or combination of ingredients commonly used in such products (e.g., flavored products), including but not limited to:

[0194] acids, including, for example, citric acid, phosphoric acid, ascorbic acid, sodium bisulfate, lactic acid, or tartaric acid;

[0195] bitter components, 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);

[0196] colorants, including, for example, caramel color, Red #40, Yellow #5, Yellow #6, Blue #1, Red #3, purple carrot, black carrot juice, purple sweet potato, vegetable juice, fruit juice, β-carotene, turmeric curcumin, or titanium dioxide;

[0197] Preservatives, including, for example, sodium benzoate, potassium benzoate, potassium sorbate, sodium metabisulfite, sorbic acid or benzoic acid;

[0198] Antioxidants, including, for example, ascorbic acid, calcium disodium EDTA, α-tocopherol, mixed tocopherols, rosemary extract, grape seed extract, resveratrol or sodium hexametaphosphate;

[0199] Vitamins or functional ingredients, including, for example, resveratrol, Co-Q10, ω3 fatty acids, theanine, choline chloride (citocoline), inositol, inulin (chicory root), taurine, ginseng extract, guarana extract, ginger extract, L-phenylalanine, L-carnitine, L-tartrate, D-glucuronolactone, inositol, bioflavonoids, echinacea, Ginkgo Biloba, yerba mate, linseed oil, Garcinia cambogia peel extract, white tea extract, ribose, milk thistle extract, grape seed extract, pyridoxine hydrochloride (vitamin B6), cyanocobalamin (vitamin B12), nicotinamide (vitamin B3), biotin, calcium lactate, calcium pantothenate (pantothenic acid), calcium phosphate, calcium carbonate, chromium chloride, chromium polynicotinate, copper sulfate, folic acid, ferric pyrophosphate, iron, magnesium lactate, magnesium carbonate, magnesium sulfate, monopotassium phosphate, monosodium phosphate, phosphorus, potassium iodide, potassium phosphate, riboflavin, sodium sulfate, sodium gluconate, sodium polyphosphate, sodium bicarbonate, thiamine mononitrate, vitamin D3, vitamin A palmitate, zinc gluconate, zinc lactate or zinc sulfate;

[0200] Clouding agents, including, for example, ester gum, brominated vegetable oil (BVO) or sucrose acetate isobutyrate (SAIB);

[0201] Buffers, including, for example, sodium citrate, potassium citrate or salts;

[0202] Flavors, such as natural flavors, natural flavors with other natural flavors (natural flavor WONF), natural and artificial flavors, artificial flavors; or

[0203] 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.

[0204] In some further embodiments, the consumer products (typically flavorized products) disclosed herein include one or more other umami or savory enhancing compounds. Such umami enhancing compounds include, but are not limited to, naturally derived compounds such as (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide (ericamide), 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.

[0205] In some further embodiments, the consumer products (typically flavorized products) disclosed herein may include one or more bitterness blocking compounds. Such bitterness blocking compounds include, but are not limited to, naturally derived compounds such as menthol or its analogs, or synthetic compounds such as any of the compounds described in U.S. Patent Nos. 8,076,491, 8,445,692, and 9,247,759.

[0206] In some further embodiments, the consumer products (typically flavorized products) disclosed herein may include one or more mouthfeel modifying compounds. Such mouthfeel modifying compounds include, but are not limited to, tannins, cellulosic materials, bamboo powder, and the like.

[0207] In some further embodiments, the consumer products (typically flavorized products) disclosed herein may include 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.

[0208] In certain embodiments, the consumer products (typically flavorized products) disclosed herein may include cyclosal. When cyclosal is present, its relative concentration is similar to that of the lactones described herein.

[0209] In some embodiments, a consumer product (typically a flavored product) contains one or more flavorings, or any other additives described in H. Mitchell, Sweeteners and Sugar Alternatives in Food Technology, Blackwell Publishing Ltd, 2006. As used herein, the term "flavoring" includes those flavors known to the person skilled in the art, such as natural and artificial flavors. These flavorings can be selected from synthetic flavor oils and flavor aromatics or oils from plants, leaves, flowers, fruits, etc., oleoresins and extracts, and combinations thereof. Non-limiting representative flavor oils include spearmint oil, cinnamon oil, wintergreen 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 cassia oil. Useful flavorings also include artificial, natural, and synthetic fruit flavors, such as vanilla, and citrus oils, including lemon, orange, lime, grapefruit, yuzu, 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 flavorings 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, carom 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, coriander flavors, sassafras flavors, savory flavors, Sichuan pepper flavors, perilla flavors, juniper flavors, ginger flavors, star anise flavors, horseradish flavors, thyme flavors, tarragon flavors, dill flavors, bell pepper flavors, nutmeg flavors, basil flavors, marjoram flavors, rosemary flavors, bay leaf flavors, and wasabi flavors; wine flavors, such as red wine flavors, whiskey flavors, brandy flavors, rum flavors, gin flavors, and liqueur flavors; flower flavors; and vegetable flavors, such as onion flavors, garlic flavors, cabbage flavors, carrot flavors, celery flavors, mushroom flavors, and tomato flavors.These flavoring agents can be used in liquid or solid form and can be used alone or in combination. Commonly used flavorings include mint, such as peppermint, menthol, spearmint, artificial vanilla, cinnamon derivatives, and various fruit flavorings, whether used alone or in combination. The flavoring agents can also provide breath freshening properties, especially mint flavoring agents when combined with cooling agents.

[0210] The flavoring agents can also provide breath freshening properties, especially mint flavoring agents when combined with cooling agents. These flavoring agents can be used in liquid or solid form and can be used alone or in combination. Other useful flavoring agents include aldehydes and esters, such as cinnamyl acetate, cinnamaldehyde, citral diethyl acetal, dihydrocarvyl acetate, eugenyl formate, p-methylanisole, and the like. Generally, any flavoring agent or food additive can be used, such as those described by the National Academy of Sciences in Chemicals Used in Food Processing, publication 1274, pages 63-258.

[0211] Other examples of aldehyde flavoring agents include, but are not limited to, acetaldehyde (apple), benzaldehyde (cherry, almond), anisaldehyde (licorice, anise), cinnamaldehyde (cinnamon), citral, i.e., α-citral (lemon, lime), neral, i.e., β-citral (lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotropin, i.e., piperonal (vanilla, cream), vanillin (vanilla, cream), α-amylcinnamaldehyde (spicy fruity flavor), butyraldehyde (butter, cheese), valeraldehyde (butter, cheese), citronellal (modified products, various types), decanal (citrus fruits), aldehyde C-8 (citrus fruits), aldehyde C-9 (citrus fruits), aldehyde C-12 (citrus fruits), 2-ethylbutyraldehyde (berries), hexenal, i.e., trans-2 (berries), tolualdehyde (cherry, almond), veratraldehyde (vanilla), 2,6-dimethyl-5-heptenal, i.e., melonal (melon), 2,6-dimethyloctanal (green fruits), and 2-dodecenal (citrus, tangerine), cherry, grape, strawberry shortcake, and mixtures thereof. This list of flavoring agents is merely exemplary and is not meant to generally limit the term "flavoring agent" or the scope of the general disclosure.

[0212] The flavored product can be any flavored product according to the forms and embodiments described below. In some embodiments, the flavored product is a beverage product, such as a fortified sparkling beverage, cola, lemon-lime flavored sparkling beverage, orange flavored sparkling beverage, grape flavored sparkling beverage, strawberry flavored sparkling beverage, pineapple flavored sparkling beverage, ginger ale, root beer, fruit juice, fruit flavored juice, fruit juice drink, nectar drink, vegetable juice, vegetable flavored juice, sports drink, energy drink, fortified water beverage, vitamin fortified water, near-water beverage, coconut water, tea beverage, coffee, cocoa beverage, milk component-containing beverage, cereal extract-containing beverage, and smoothie. In some other embodiments, the flavored product is a food product, such as a packaged food, canned food, meal replacement product, etc. In some embodiments, the flavored product is an oral care product, such as toothpaste, mouthwash, or a teeth whitening composition, such as the composition disclosed in U.S. Patent Application Publication No. 2019 / 0167545, which is incorporated herein by reference.

[0213] In embodiments where the flavored product is a beverage, the beverage can be selected from fortified sparkling beverages, cola, lemon-lime flavored sparkling beverages, orange flavored sparkling beverages, grape flavored sparkling beverages, strawberry flavored sparkling beverages, pineapple flavored sparkling beverages, ginger ale, root beer, fruit juices, fruit flavored juices, fruit juice drinks, nectar drinks, vegetable juices, vegetable flavored juices, sports drinks, energy drinks, fortified water beverages, vitamin fortified water, near-water beverages, coconut water, tea beverages, coffee, cocoa beverages, milk component-containing beverages, cereal extract-containing beverages, and smoothies. In some embodiments, the beverage can be a soft drink.

[0214] The flavored product can be in any suitable physical form. For example, in some embodiments, the flavored composition can be in solid form, such as a powder. In further such embodiments, the flavored product is tooth powder, such as tooth powder for whitening teeth, removing stains (such as tobacco stains), etc. In some other embodiments, the flavored product can be a paste or slurry, such as toothpaste. In some other embodiments, the flavored product can be in the form of a cream or gel, such as a tooth gel, skin cream, or tooth cream. In some other embodiments, the flavored product can be, for example, a liquid suspension or solution having an aqueous carrier. In some embodiments, the flavored product can be in the form of an emulsion, such as a microemulsion or nanoemulsion, in which surfactants, emulsifiers, etc. can be present. In some embodiments, the flavored product is a personal care product, such as a product for application to the skin, face, lips, gums, oral cavity, etc. Such personal products can be used for any suitable purpose, such as skin whitening, teeth whitening, etc.

[0215] In some embodiments, the flavored product is an oral care product. By "oral care product" is meant a personal care product or other product that is not intended to be intentionally swallowed for the purpose of systemic administration of a specific therapeutic agent during normal use, but rather is retained in the oral cavity for a sufficient period of time to contact substantially all tooth surfaces and / or oral tissues for oral activities. Oral care compositions can be in a variety of forms, including toothpaste, dentifrice, dental gels, subgingival gels, mouthwash, mousse, foam, oral sprays, lozenges, chewable tablets, chewing gum, or denture products. Oral care compositions can also be incorporated into strips or films for direct application or attachment to oral surfaces.

[0216] In some embodiments, the flavored product is a pharmaceutical product, such as a product designed to carry or deliver certain active pharmaceutical ingredients (APIs). Such APIs can be over-the-counter (OTC) drugs, such as acetaminophen, and other OTC cough and cold medications. In some embodiments, the API is a prescription-based drug.

[0217] In certain embodiments relating to any form and embodiment of the flavored product set forth herein, the flavored product is a non-naturally occurring product, such as a packaged food or beverage product.

[0218] Other non-limiting examples of food and beverage products or formulations include sweet coatings, icings or glazes for such products, or any entity included in: soups, dry-processed foods, beverages, ready-to-eat foods, canned or pickled foods, frozen-processed foods, refrigerated-processed foods, snack foods, baked goods, confectionery, dairy products, ice cream, meal replacements, pasta and noodles, and sauces, seasonings, flavorings, baby foods, and / or spreads.

[0219] Generally, soups are meant canned / pickled, dehydrated, instant, refrigerated, UHT, and frozen soups. For the purposes of this definition, a soup is a food product made from meat, poultry, fish, vegetables, grains, fruits, and other ingredients, cooked in a liquid, which may contain visible pieces of some or all of these ingredients. It may be clear (as a broth) or thick (as a chowder), smooth, pureed, or chunky, ready-to-eat, semi-concentrated, or concentrated, and can be served cold or hot, as a first course or main course or as a snack between meals (sipping beverage). Soups can be used as an ingredient for preparing other meal components, ranging from a broth (consommé) to a sauce (cream- or cheese-based soups).

[0220] Dehydrated and cooked food products generally refer to: (i) cooking aids such as powdered, granular, paste-like, and concentrated liquid products, including concentrated broth (bouillon), broth, and pressed blocks, tablets, or powdered or granular broth-like products sold separately as finished products or as ingredients in products, seasonings, and formulation mixtures (not technology-related); (ii) dietary solution products such as dehydrated soups and freeze-dried soups, including dehydrated soup mixtures, dehydrated instant soups, dehydrated ready-to-eat soups, dehydrated or self-heating preparations of ready-made dishes, meals, and single-serve main courses, including pasta, potatoes, and rice; (iii) dietary garnish products such as condiments, marinades, salad dressings, salad toppings, dips, coating mixes, batter mixes, shelf-stable sauces, barbecue sauces, liquid formulation mixtures, concentrates, sauce or sauce mixtures, including salad formulation mixtures, sold as finished products or as ingredients in products, whether dehydrated, liquid, or frozen.

[0221] Beverage products generally refer to beverages, beverage mixtures, and concentrates, including but not limited to carbonated and non-carbonated beverages, alcoholic and non-alcoholic beverages, ready-to-drink beverages, liquid concentrate blends for preparing beverages (such as soda water), and dry beverage precursor mixtures. Beverage products also include alcoholic beverages, soft drinks, sports drinks, isotonic drinks, and hot beverages. Alcoholic beverages include but are not limited to beer, cider / perry, FABs, wine, and spirits. Soft drinks include but are not limited to carbonated beverages such as cola and non-cola carbonated beverages; fruit juices such as fruit juice, nectar, fruit juice drinks, and fruit-flavored drinks; bottled water including soda water, spring water, and purified / table water; functional beverages which can be carbonated or non-carbonated, including sports drinks, energy drinks, or elixir drinks; concentrates such as ready-to-drink liquid and powder concentrates. Whether hot or cold, they include but are not limited to coffee or iced coffee such as fresh, instant, 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.

[0222] Snack (or appetizer) products generally refer to any food for 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, tortilla chips / 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.

[0223] Baked goods generally refer to any edible products that involve exposure to heat or excessive sunlight during the preparation process. Examples of baked goods include, but are not limited to, bread, buns, cookies, muffins, cereals, toaster pastries, pastries, waffles, tortillas, crackers, pies, bagels, egg tarts, quiches, cakes, any baked goods and any combination thereof. Other examples include, but are not limited to: packaged / industrial bread, bulk / artisanal bread, packaged / industrial cakes, bulk / artisanal cakes, cookies, chocolate-coated cookies, sandwich cookies, filled cookies, savory crackers and wafers, bread substitutes, breakfast cereals, ready-to-eat cereals, home breakfast cereals, corn flakes, muesli, other cereals, children's breakfast cereals, and hot cereals.

[0224] Ice cream generally refers to frozen desserts that contain cream, sugar, and flavorings. Examples of ice cream include, but are not limited to: impulse ice cream; family-sized ice cream; frozen yogurt and artisanal ice cream; ice cream based on soy, oats, legumes (such as adzuki beans and mung beans), and rice. Further examples of ice cream include, but are not limited to, single-serve dairy ice cream, single-serve water ice cream, multi-pack dairy ice cream, multi-pack water ice cream, family-sized dairy ice cream, ice cream desserts, bulk ice cream, and family-sized water ice cream.

[0225] Confectionery generally refers to any edible products that taste sweet. Examples of confectionery include, but are not limited to, hard candies, gelatin, chocolate candies, sugar confections, chewing gums, etc. and any combination products. Other examples include, but are not limited to: chocolate chips, chocolate bars (countlines), bagged chocolate bars (selflines) / soft bars (softlines), boxed assortments, standard boxed assortments, twist-wrapped mini chocolates, flavored chocolates, chocolates with toys, alfajores, other chocolate confections, mints, standard mints, strong mints, hard candies, soft lozenges, chewing gums, jelly candies and chew candies, toffees, caramels, and nougats, medicated candies, lollipops, licorice, other sugar confections.

[0226] Meal replacement foods generally refer to any foods that are designed to replace regular meals, especially for those who are concerned about health or fitness. Examples of meal replacements include, but are not limited to, weight loss products and rehabilitation products.

[0227] Ready-to-eat foods generally refer to any foods that can be eaten as a meal without extensive preparation or processing. Ready-to-eat foods include products for which manufacturers have added recipe "skills", so they have a high degree of ready-to-eat, completeness, and convenience. Examples of ready-to-eat foods include, but are not limited to, canned / pickled, frozen, dried, refrigerated ready-to-eat foods; dinner mixes; frozen pizzas; refrigerated pizzas; and pre-made salads.

[0228] Pasta and noodles include any pasta and / or noodles, including but not limited to canned, dried, and refrigerated / fresh pasta; and plain, instant, refrigerated, frozen, and snack noodles.

[0229] Canned / preserved foods include but are not limited to canned / preserved meat and meat products, fish / seafood, vegetables, tomatoes, beans, fruits, ready-to-eat foods, soups, pasta, and other canned / preserved foods.

[0230] Frozen processed foods include but are not limited to frozen processed red meat, processed poultry, processed fish / seafood, processed vegetables, meat substitutes, processed potatoes, baked products, desserts, ready-to-eat foods, pizza, soups, noodles, and other frozen foods.

[0231] Dry processed foods include but are not limited to rice, dessert mixes, dry ready-to-eat foods, dehydrated soups, instant soups, dry pasta, plain noodles, and instant noodles. Refrigerated processed foods include but are not limited to refrigerated processed meats, processed fish / seafood products, lunch boxes, fresh cut fruits, ready-to-eat foods, pizza, pre-made salads, soups, fresh pasta, and noodles.

[0232] Sauces, seasonings, and condiments include but are not limited to tomato ketchup and puree, broth / soup cubes, herbs and spices, monosodium glutamate (MSG), table sauces, soy-based sauces, pasta sauces, wet / cooking sauces, dry sauce / powder mixtures, tomato paste, mayonnaise, mustard, salad dressings, balsamic vinaigrette, dips, pickles, and other sauces, seasonings, and condiments.

[0233] Baby foods include but are not limited to milk- or soy-based formula; and ready-made, dried, and other baby foods.

[0234] Spreads include but are not limited to jams and jellies, honey, chocolate spreads, nut spreads, and yeast spreads.

[0235] Dairy products generally refer to edible products derived from the milk of mammals. Examples of dairy products include, but are not limited to, drinking milk products, cheeses, yogurts, and kefir, as well as other dairy products. Further examples of dairy products include, but are not limited to, fresh / pasteurized milk, whole fresh / pasteurized milk, semi-skimmed fresh / pasteurized milk, long-life / UHT milk, whole long-life / UHT milk, semi-skimmed long-life / UHT milk, skimmed long-life / UHT milk, goat milk, condensed milk / evaporated milk, plain condensed milk / evaporated milk, flavored, functional, and other condensed milks, flavored milk beverages, dairy-only flavored milk drinks, flavored milk drinks with fruit juice, soy milk, fermented milk beverages, coffee creamers, milk powder, flavored milk powder drinks, cream, cheese, processed cheese, spreadable cheese, non-spreadable processed cheese, unprocessed cheese, spreadable unprocessed cheese, hard cheese, packaged hard cheese, unpackaged hard cheese, plain / natural yogurt, flavored yogurt, fruit yogurt, probiotic yogurt, drinking yogurt, regular drinking yogurt, and probiotic drinking yogurt.

[0236] In some embodiments, the flavored products include one or more candies, chocolate candies, chocolate chips, chocolate bars (countlines), bagged chocolate bars (selflines) / soft bars (softlines), boxed assortments, standard boxed assortments, twist-wrapped mini chocolates, flavored chocolates, chocolates with toys, caramel milk filled cookies, other chocolate confections, mints, standard mints, strong mints, hard candies, soft lozenges, chewing gums, jelly candies and chewing candies, toffees, caramels and nougats, medicated candies, lollipops, licorice, other granulated sugar foods, breads, packaged / industrial breads, bulk / artisanal breads, pastries, cakes, packaged / industrial cakes, bulk / artisanal cakes, cookies, chocolate-coated cookies, sandwich cookies, filled cookies, savory crackers and wafers, bread substitutes, breakfast cereals, ready-to-eat cereals, family breakfast cereals, corn flakes, cereal mixes, other cereals, children's breakfast cereals, hot cereals, ice creams, ready-to-eat ice creams, single-serve dairy ice creams, single-serve water ice creams, multi-pack dairy ice creams, multi-pack water ice creams, family-size ice creams, family-size dairy ice creams, ice cream desserts, bulk ice creams, family-size water ice creams, frozen yogurts, artisanal ice creams, dairy products, milk, fresh / pasteurized milk, whole fresh / pasteurized milk, semi-skimmed fresh / pasteurized milk, long-life / UHT milk, whole long-life / UHT milk, semi-skimmed long-life / UHT milk, skimmed long-life / UHT milk, goat's milk, condensed milk / evaporated milk, plain condensed milk / evaporated milk, flavored, functional and other condensed milks, flavored milk beverages, dairy-only flavored milk drinks, flavored milk drinks with fruit juices, soy milk, yogurt drinks, fermented milk drinks, coffee creamers, milk powders, flavored milk powder drinks, creams, cheeses, processed cheeses, spreadable cheeses, non-spreadable processed cheeses, unprocessed cheeses, spreadable unprocessed cheeses, hard cheeses, packaged hard cheeses, unpackaged hard cheeses, yogurts, plain / natural yogurts, flavored yogurts, fruit yogurts, probiotic yogurts, drinking yogurts, regular drinking yogurts, probiotic drinking yogurts, frozen and shelf-stable desserts, dairy-based desserts, soy-based desserts, frozen desserts, fresh cheeses and quark cheeses, plain fresh cheeses and quark cheeses, flavored fresh cheeses and quark cheeses, savory fresh cheeses and quark cheeses, sweet and savory snacks, fruit snacks, potato chips / crisps, extruded snack foods, tortilla chips / corn chips, popcorn, pretzels, nuts, other sweet and savory snacks, snack bars, granola bars, breakfast bars, energy bars, fruit bars, other snack bars, meal replacements, weight loss products, recovery drinks, ready-to-eat foods, canned ready-to-eat foods, frozen ready-to-eat foods, dried ready-to-eat foods, frozen ready-to-eat meals, dinner mixes, frozen pizzas, refrigerated pizzas, soups, canned soups, dehydrated soups, instant soups, cold soups, hot soups, frozen soups, pastas, canned pastas, dried pastas, frozen / fresh pastas, noodles, plain noodles, instant noodles, cup / bowl instant noodles, bagged instant noodlesFrozen noodles, snack noodles, canned foods, canned meat and meat products, canned fish / seafood, canned vegetables, canned tomatoes, canned beans, canned fruits, 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 alternatives, frozen potatoes, oven-baked potato chips, other oven-baked potato products, non-oven frozen potatoes, frozen baked goods, frozen desserts, frozen ready-to-eat foods, frozen pizza, frozen soups, frozen noodles, other frozen foods, dried foods, dessert mixes, dried ready-to-eat foods, dehydrated soups, instant soups, dried pasta, plain noodles, instant noodles, cup / bowl instant noodles, bagged instant noodles, refrigerated foods, refrigerated processed meat, refrigerated fish / seafood products, refrigerated processed fish, refrigerated coated fish, refrigerated smoked fish, refrigerated lunch packs, refrigerated ready-to-eat foods, refrigerated pizza, refrigerated soups, refrigerated / fresh pasta, refrigerated noodles, oils and fats, olive oil, vegetable and seed oils, cooking fats, butter, margarine, spread oils and fats, functional spread oils and fats, sauces, seasonings and condiments, tomato paste and puree, broth / soup cubes, soup cubes, gravy granules, liquid soup bases and ingredients, herbs and spices, fermented sauces, soy-based sauces, pasta sauces, wet sauces, dry sauce / powder mixes, ketchup, mayonnaise, regular mayonnaise, mustard, salad dressings, regular salad dressings, low-fat salad dressings, balsamic vinaigrette, dips, pickles, other sauces, seasonings and condiments, baby foods, formula milk, standard formula milk, growing-up formula milk, toddler formula milk, hypoallergenic formula milk, prepared baby foods, dried baby foods, other baby foods, spreads, jams and preserves, honey, chocolate spreads, nut spreads and yeast spreads.、

[0237] Some embodiments provide chewable compositions that may or may not be swallowable. In some embodiments, the chewable composition can be gummy candies, chewing gums, sugar-free gummy candies, functional gummy candies, bubble gums, which individually or in combination contain the compounds disclosed and described herein.

[0238] In some embodiments of any of the foregoing embodiments, the liquid composition can be included in a body care product such as a product suitable for application to human hair or skin. Thus, the consumer products of the present disclosure can be body care products, typically beauty products, skin care products or hair care products.

[0239] In some embodiments, the body care product comprises one or more fragrances. In some embodiments, at least a portion of the fragrance may be encapsulated. Suitable fragrances include complex mixtures of fragrance compounds selected to provide any desired odor. In the context of the present disclosure, the term "fragrance" is used synonymously with "perfume". Fragrance compounds commonly used in the perfume art and suitable for the purposes of the present disclosure are more fully described in S. Arctander's PERFUME FLAVORS AND CHEMICALS, Vols. I and II (1969) and THE MERCK INDEX, 8th edition, Merck & Co., Inc., Rahway, N.J. The term "fragrance compound" encompasses both naturally occurring and synthetic materials known for use in perfumery, as well as animal oils. Fragrance compounds may also be any natural oil or extract, or chemical compound used in a fragrance composition. Natural oils and extracts are described in Guenther's THE ESSENTIAL OILS 1949 and may include extracts, pressings, collected exudates, and distillates from any of the following parts of suitable plants: roots, rhizomes, bulbs, corms, stems, bark, heartwood, leaves, flowers, seeds, and fruits. Examples of such extracts and distillates include citrus fruit oils such as oils of orange, mandarin, grapefruit, lime, or lemon, tree oils such as pine or cedar, herb oils such as peppermint, thyme, lavender, basil, rosemary, clove, or flower extracts such as oils of rose, jasmine, lily of the valley, or geranium.

[0240] Non-limiting examples of suitable fragrances include natural oils or natural-derived materials, as well as synthetic fragrances such as hydrocarbons, alcohols, aldehydes, ketones, esters, lactones, ethers, nitriles, and polyfunctional compounds. Non-limiting examples of natural oils include the following: basil (Ocimum basilicum) oil, bay (Pimento acris) oil, bee balm (Monarda didyma) oil, bergamot (Citrus aurantium bergamia) oil, cardamom (Elettaria cardamomum) oil, cedarwood (Cedrus atlantica) oil, chamomile (Anthemis nobilis) oil, cinnamon (Cinnamomum cassia) oil, citronella (Cymbopogon nardus) oil, clary sage (Salvia sclarea) oil, clove (Eugenia caryophyllus) oil, clove leaf (Eufenia caryophyllus) oil, cyperus (Cyperus esculentus) oil, cypress (Cupressus sempervirens) oil, lemon eucalyptus (Eucalyptus citriodora) oil, geranium (Geranium maculatum) oil, ginger (Zingiber officinale) oil, grapefruit (Citrus grandis) oil, hazelnut (Corylus avellana) nut oil, jasmine (Jasminum officinale) oil, juniper (Juniperus communis) oil, juniper tar (Juniperus oxycedrus tar), red cedar (Juniperus virginiana) oil, kiwi (Actinidia chinensis) water, lavandin (Lavandula hybrida) oil, lavender (Lavandula angustifolia) oil, lavender (Lavandula angustifolia) water, lemon (Citrus medica limonum) oil, lemongrass (Cymbopogon schoenanthus) oil, lime (Citrus aurantifolia) oil, linden (Tilia cordata) oil, linden (Tilia cordata) water, mandarin (Citrus nobilis,Oils of Citrus nobilis Lour., Myristica fragrans, Citrus aurantium dulcis flower oil, Citrus aurantium dulcis oil, Citrus aurantium dulcis water, Pogostemon cablin oil, Menthe piperita oil, Menthe piperita water, Rosmarinus officinalis oil, rose oil, Rosa damascena extract, Rosa multiflora extract, Aniba rosaeodora extract, Salvia officinalis oil, Santalum album oil, Menthe viridis oil, Melaleuca alternifolia oil and Cananga odorata oil. Some non-limiting examples of synthetic hydrocarbon fragrances include caryophyllene, β-farnesene, limonene, α-pinene and β-pinene. Some non-limiting examples of synthetic alcohol fragrances include bacdanol, citronellol, linalool, phenylethyl alcohol and α-terpineol. Some non-limiting examples of synthetic aldehyde fragrances include 2-methylundecanal, citral, hexyl cinnamic aldehyde, isocyclocitral, lily aldehyde and 10-undecenal. Some non-limiting examples of synthetic ketone fragrances include cashmeran, α-ionone, isocyclemone E, koavone, muscone and tonalide. Some non-limiting examples of synthetic ester fragrances include benzyl acetate, 4-tert-butylcyclohexyl acetate (cis and trans), cedryl acetate, tricyclodecenyl acetate (cyclacet), isobornyl acetate and α-terpinyl acetate (R = acetyl). Some non-limiting examples of synthetic lactone fragrances include coumarin, jasmine lactone, musk lactone and peach aldehyde. Some non-limiting examples of synthetic ether fragrances include ambroxan, anther and galaxolide. Some non-limiting examples of synthetic nitrile fragrances include cinnamyl nitrile and geranyl nitrile. Finally, some non-limiting examples of synthetic polyfunctional fragrances include amyl salicylate, isoeugenol, methyl dihydrojasmonate (hedione), heliotropine, Lyral and vanillin.,

[0241] In some embodiments, the body care composition may comprise one or more ingredients that provide active beneficial effects for hair or skin care, such as compounds having antioxidant activity. For example, in some embodiments, the body care product contains ascorbic acid, also known as vitamin C, which is an essential nutrient with antioxidant activity. In some embodiments, the body care composition contains vitamin E, which refers to eight structurally related antioxidant compounds that exhibit free radical scavenging activity. These compounds include four tocopherol compounds and four tocotrienol compounds. In some embodiments, the body care composition contains resveratrol, which is an antioxidant compound naturally present in grape skins. In some embodiments, the body care composition contains certain oligopeptides, such as acetyl hexapeptide-8 (also known as acetyl hexapeptide-3), which is a synthetic peptide that relaxes wrinkles. A variety of other such compounds may also be included, such as retinol, niacinamide, coenzyme Q10, and various polyphenols, such as flavonoids like catechins. The amounts of these active ingredients can be the same as the typical amounts in other body care products.

[0242] The body care compositions disclosed herein can be included or incorporated into any suitable type of vehicle and carrier. Generally, the vehicle or carrier will be a dermatologically acceptable vehicle or carrier. Non-limiting examples of the vehicle or carrier include water, glycerin, alcohols, oils, silicon-containing compounds, silicone compounds, and waxes. Variations and other suitable carriers will be apparent to those skilled in the art and are suitable for use in the body care compositions of the present disclosure. In certain embodiments, the concentrations and combinations of the compounds, ingredients, and reagents can be selected such that these combinations are chemically compatible and do not form complexes that precipitate from the finished body care product.

[0243] The body care compositions disclosed herein can be constructed or formulated in a variety of different forms. Non-limiting examples include emulsions (e.g., oil-in-water, water-in-oil-in-water, water-in-oil, water-in-silicone, silicone-in-water, oil-in-water-in-oil, silicone-in-water-in-oil emulsions, etc.), creams, lotions, solutions (e.g., aqueous or hydroalcoholic), anhydrous matrices (e.g., lipsticks and powders), gels, masks, scrubs, body butters, exfoliating creams, and ointments. Variations and other structures will be apparent to those skilled in the art and are suitable for use in the body care compositions of the present disclosure.

[0244] A variety of other ingredients can be used, such as ingredients commonly used in cosmetics, skin care products or hair care products. The CTFA INTERNATIONAL COSMETIC INGREDIENT DICTIONARY AND HANDBOOK (2004 and 2008) describes a variety of non-limiting ingredients that can be used in the compositions disclosed in the present invention. Examples of these ingredient categories include: fragrances (artificial and natural; such as gluconic acid, phenoxyethanol and triethanolamine), dye and pigment ingredients (such as Blue 1, Blue 1 Lake, Red 40, titanium dioxide, D&C Blue No. 4, D&C Green No. 5, D&C Orange No. 4, D&C Red No. 17, D&C Red No. 33, D&C Violet No. 2, D&C Yellow No. 10 and D&C Yellow No. 11), flavoring agents or fragrances (such as Stevia rebaudiana (stevia) extract and menthol), adsorbents, lubricants, solvents, humectants (including, for example, emollients, wetting agents, film formers, occlusives and agents that affect the skin's natural moisturizing mechanism), water-repellants, UV absorbers (physical and chemical absorbers, such as para-aminobenzoic acid (“PABA”) and corresponding PABA derivatives, titanium dioxide, zinc oxide, etc.), essential oils, vitamins (such as B, D, E and K), trace metals (such as zinc, calcium and selenium), anti-irritants (such as steroids and non-steroidal anti-inflammatory drugs), plant extracts (such as aloe vera, chamomile, cucumber extract, ginkgo biloba, ginseng and rosemary), anti-microbial agents, antioxidants (such as BHT and tocopherol), chelating agents (such as disodium EDTA and tetrasodium EDTA), preservatives (such as methylparaben and propylparaben), pH regulators (such as sodium hydroxide and citric acid), absorbents (such as starch octenyl succinate aluminum, kaolin, corn starch, oat starch, cyclodextrin, talc and zeolite), skin bleaching and brightening agents (such as hydroquinone and nicotinamide lactate), humectants (such as sorbitol, urea, methyl gluceth 20, saccharide isomerate and mannitol), exfoliants, waterproofing agents (such as magnesium hydroxide / aluminum hydroxide stearate), skin conditioners (such as aloe vera extract, allantoin, bisabolol, ceramides, dimethicone, hyaluronic acid, biosaccharide gum-1, ethylhexylglycerin, pentylene glycol, hydrogenated polydecene, octyldodecyl oleate and dipotassium glycyrrhizate). Further non-limiting examples of some of these ingredients are provided in the following subsections.

[0245] In some embodiments, the body care composition comprises one or more UV absorbers or reflectors. Suitable UV absorbers or reflectors include chemical and physical sunscreens. Non-limiting examples of chemical sunscreens include para-aminobenzoic acid (PABA), PABA esters (PABA glycerol esters, PABA pentyl dimethyl ester, and PABA octyl dimethyl ester), PABA butyl ester, PABA ethyl ester, PABA ethyl dihydroxypropyl ester, benzophenones (oxybenzone, sulisobenzone, benzophenone, and benzophenones 1 to 12), cinnamates / esters (octyl methoxycinnamate (oxtinoxate), isoamyl p-methoxycinnamate, octyl methoxycinnamate, cinoxate, methyl diisopropylcinnamate, DEA salt of methoxycinnamic acid, ethyl diisopropylcinnamate, glyceryl octanoate dimethoxycinnamate, and ethyl methoxycinnamate), cinnamic esters, salicylates / esters (homomenthyl salicylate, benzyl salicylate, ethylene glycol salicylate, isopropylbenzyl salicylate, etc.), anthranilates / esters, ethyl urocanate, homosalate, octisalate, dibenzoylmethane derivatives (such as avobenzone), octocrylene, octyl triazone, dioctyl triazone, digalloyl trioleate, glycerol aminobenzoate, 2-hydroxy-1,4-naphthoquinone (lawsone), and dihydroxyacetone, ethylhexyl triazone, dioctyl butylamidotriazone, benzylidene malonate polysiloxane, terephthalylidene dicamphor sulfonic acid, phenyl dibenzimidazole tetrasulfonic acid disodium, diethylamino hydroxybenzoyl benzoic acid hexyl ester, bis-diethylamino hydroxybenzoyl benzoate, bisbenzoxazolyl phenyl ethylhexyl iminotriazine, formyl triazole trisiloxane, methylene bisbenzotriazolyl tetramethylbutylphenol, and bis-ethylhexyloxyphenol methoxyphenyl triazine, 4-methylbenzylidene camphor, and isoamyl 4-methoxycinnamate. Non-limiting examples of physical sunscreens include kaolin, talc, petrolatum, and metal oxides (such as titanium dioxide and zinc oxide).

[0246] In some embodiments, the body care composition comprises one or more moisturizing agents. Non-limiting examples of moisturizing agents that can be used include amino acids, chondroitin sulfate, diglycerin, erythritol, fructose, glucose, glycerin, glycerin polymers, ethylene glycol, 1,2,6-hexanetriol, honey, hyaluronic acid, hydrogenated honey, hydrogenated starch hydrolysates, inositol, lactitol, maltitol, maltose, mannitol, natural moisturizing factor, PEG-15 butylene glycol, polyglyceryl sorbitol, salts of pyrrolidone carboxylic acid, potassium PCA, propylene glycol, sugar isomers, sodium glucuronate, sodium PCA, sorbitol, sucrose, trehalose, urea, and xylitol. Other non-limiting examples include acetylated lanolin, acetylated lanolin alcohol, alanine, algae extract, Aloe barbadensis, Aloe barbadensis extract, Aloe barbadensis gel, Althaea officinalis extract, Prunus armeniaca kernel oil, arginine, arginine aspartate / ester, Arnica montana extract, aspartic acid, Persea gratissima oil, barrier sphingolipids, butanol, beeswax, behenyl alcohol, β-sitosterol, Betula alba bark extract, Borago officinalis extract, Ruscus aculeatus extract, butylene glycol, Calendula officinalis extract, Calendula officinalis oil, Euphorbia cerifera wax, canola oil, caprylic / capric triglyceride, Elettaria cardamomum oil, Copernicia cerifera wax, Daucus carota sativa oil, Ricinus communis oil, ceramides, ozokerite, ceteth-5, ceteth-12, ceteth-20, cetearyl octanoate, ceteareth-20, ceteareth-24, cetyl acetate, cetyl octanoate, cetyl palmitate, Anthemis nobilis oil, cholesterol, cholesterol esters, cholesteryl hydroxystearate, citric acid, Salvia sclarea oil, Theobroma cacao butter, Theobroma cacao caprylate / caprate, Cocos nucifera oil, collagen, collagen amino acids, Zeamays) oil, fatty acids, decyl oleate, dimethicone copolyol, dimethiconol, dioctyl adipate, dioctyl succinate, dipentaerythritol hexa(caprylate / caprate), DNA, erythritol, ethoxydiglycol, ethyl linoleate, Eucalyptus globulus oil, Oenothera biennis oil, fatty acids, Geranium maculatum oil, glucosamine, glucosylglutamate, glutamic acid, glycereth-26, glycerin, glycerol, glyceryl distearate, glyceryl hydroxystearate, glyceryl laurate, glyceryl linoleate, glyceryl myristate, glyceryl oleate, glyceryl stearate, glyceryl stearate SE, glycine, ethylene glycol stearate, ethylene glycol stearate SE, glucosaminoglycan, Vitis vinifera seed oil, Corylus americana (American hazelnut) nut oil, Corylus avellana (European hazelnut) nut oil, hexylene glycol, hyaluronic acid, Carthamus tinctorius (safflower) oil blend, hydrogenated castor oil, hydrogenated coconut glycerides, hydrogenated coconut oil, hydrogenated lanolin, hydrogenated lecithin, hydrogenated palm glycerides, hydrogenated palm kernel oil, hydrogenated soybean oil, hydrogenated tallow glycerides, hydrogenated vegetable oil, hydrolyzed collagen, hydrolyzed elastin, hydrolyzed glucosaminoglycan, hydrolyzed keratin, hydrolyzed soy protein, hydroxylated lanolin, hydroxyproline, isocetyl stearate, isocetyl stearoyl stearate, isodecyl oleate, isopropyl isostearate, isopropyl lanolate, isopropyl myristate, isopropyl palmitate, isopropyl stearate, isostearamide DEA, isostearic acid, isostearyl lactate, isostearyl neopentanoate, Jasminum officinale oil, Buxus chinensis oil, kelp, Aleurites moluccana nut oil, lactamide MEA, laneth-16, laneth-10 acetate, lanolin, lanolin acid, lanolin alcohol, lanolin oil, lanolin wax, Lavandula angustifolia oil, lecithin, Citrus medica limonum oil, linoleic acid, linolenic acid, Macadamiaternifolia oil, maltitol, chamomillarecutita oil, methyl glucose sesquistearate, methylsilanol PCA, mineral oil, mink oil, mortierella oil, myristyl lactate, myristyl myristate, myristyl propionate, neopentyl glycol dicaprylate / dicaprate, octyldodecanol, octyldodecyl myristate, octyldodecyl stearoyl stearate, octyl hydroxystearate, octyl palmitate, octyl salicylate, octyl stearate, oleic acid, olive (Olea europaea) oil, orange (Citrus aurantiumdulcis) oil, palm (Elaeis guineensis) oil, palmitic acid, panthenol, panthenyl ethyl ether, paraffin, PCA, peach (Prunus persica) kernel oil, peanut (Arachis hypogaea) oil, PEG-8C12-18 esters, PEG-15 coconut alkylamine, PEG-150 distearate, PEG-60 glyceryl isostearate, PEG-5 glyceryl stearate, PEG-30 glyceryl stearate, PEG-7 hydrogenated castor oil, PEG-40 hydrogenated castor oil, PEG-60 hydrogenated castor oil, PEG-20 methyl glucose sesquistearate, PEG-40 sorbitan full oleate, PEG-5 soy sterol, PEG-10 soy sterol, PEG-2 stearate, PEG-8 stearate, PEG-20 stearate, PEG-32 stearate, PEG-40 stearate, PEG-50 stearate, PEG-100 stearate, PEG-150 stearate, pentadecalactone, peppermint (Mentha piperita oil, Petrolatum, phospholipids, plankton extract, polyamino acid polysaccharide condensate, polyglyceryl-3 diisostearate, polyquaternium-24, polysorbate 20, polysorbate 40, polysorbate 60, polysorbate 80, polysorbate 85, potassium myristate, potassium palmitate, propylene glycol, propylene glycol dicaprylate / dicaprate, propylene glycol dicaprylate, propylene glycol dipelargonate, propylene glycol laurate, propylene glycol stearate, propylene glycol stearate SE, PVP, pyridoxine dipalmitate, retinol, retinyl palmitate, rice (Oryza sativa) bran oil, RNA, rosemary (Rosmarinus officinalis) oil, rose oil, safflower (Carthamus tinctorius) oil, sage (Salvia officinalis) oil officinalis oil, sandalwood (Santalumalbum) oil, serine, serum albumin, sesame (Sesamumindicum) oil, shea butter (Butyrospermumparkii) oil, silk powder, sodium chondroitin sulfate, sodium hyaluronate, sodium lactate, sodium palmitate, sodium PCA, sodium polyglutamate, soluble collagen, sorbitan laurate, sorbitan oleate, sorbitan palmitate, sorbitan sesquioleate, sorbitan stearate, sorbitol, soybean (Glycine soja) oil, sphingolipid, squalane, squalene, stearamide MEA-stearate, stearic acid, stearoxy poly dimethyl siloxane, stearoxy trimethyl silane, stearyl alcohol, stearyl glycyrrhetinate, stearyl heptanoate, stearyl stearate, sunflower (Helianthus annuus) seed oil, sweet almond (Prunus amygdalus dulcis) oil, synthetic beeswax, tocopheryl acetate, tocopheryl linoleate, tribehenin, tridecyl neopentanoate, tridecyl stearate, triethanolamine, tristearin, urea, vegetable oil, water, wax, wheat (Triticum vulgare) germ oil and ylang (Cananga odorata) oil.

[0247] In some embodiments, the body care product may comprise one or more antioxidants, for example, in addition to or in combination with those disclosed above. For example, in some embodiments, one or more of these additional antioxidants may be used in combination with ascorbic acid, vitamin E, or a combination thereof. Non-limiting examples of antioxidants that may be used include acetylcysteine, ascorbic acid derivatives such as ascorbic acid polypeptides, ascorbyl dipalmitate, ascorbyl methylsilanol pectinate, ascorbyl palmitate, ascorbyl stearate, BHA, BHT, tert-butylhydroquinone, cysteine, cysteine HCl, dipentylhydroquinone, ditert-butylhydroquinone, dicetyl thiodipropionate, dioleyl tocopherylmethylsilanol, disodium ascorbyl sulfate, distearyl thiodipropionate, di(tridecyl) thiodipropionate, dodecyl gallate, erythorbic acid, ascorbyl esters, ethyl ferulate, ferulic acid, gallate esters, hydroquinone, isooctyl thioglycolate, kojic acid, magnesium ascorbate, magnesium ascorbyl phosphate, methylsilanol ascorbate, natural plant antioxidants such as green tea or grape seed extract, nordihydroguaiaretic acid, octyl gallate, phenylthioglycolic acid, potassium ascorbyl tocopheryl phosphate, potassium sulfite, propyl gallate, quinone, rosmarinic acid, sodium ascorbate, sodium bisulfite, sodium erythorbate, sodium metabisulfite, sodium sulfite, superoxide dismutase, sodium thioglycolate, sorbitol furfural, thiodiglycol, thiodiglycolamide, thiodiglycolic acid, thioglycolic acid, thiolactic acid, thiosalicylic acid, tocopheryl polyethylene glycol-5, tocopheryl polyethylene glycol-10, tocopheryl polyethylene glycol-12, tocopheryl polyethylene glycol-18, tocopheryl polyethylene glycol-50, tocophersolan, tocopheryl acetate, tocopheryl linoleate, tocopheryl nicotinate, tocopheryl succinate, and tris(nonylphenyl) phosphite.

[0248] In some embodiments, the body care composition comprises one or more structurants. In certain embodiments, the structurant helps to provide rheological properties to the composition that contribute to stability. In some embodiments, the structurant may also act as an emulsifier or surfactant. Non-limiting examples of structurants include stearic acid, palmitic acid, stearyl alcohol, cetyl alcohol, behenyl alcohol, stearic acid, palmitic acid, polyethylene glycol ethers of stearyl alcohol having an average of about 1 to about 21 ethylene oxide units, polyethylene glycol ethers of cetyl alcohol having an average of about 1 to about 5 ethylene oxide units, and mixtures thereof.

[0249] In some embodiments, the body care composition comprises one or more emulsifiers. Emulsifiers can reduce the interfacial tension between phases and improve the formulation and stability of the emulsion. Emulsifiers can be nonionic, cationic, anionic, and zwitterionic emulsifiers. Non-limiting examples include esters of glycerol, esters of propylene glycol, fatty acid esters of polyethylene glycol, fatty acid esters of polypropylene glycol, esters of sorbitol, esters of sorbitan, carboxylic acid copolymers, esters and ethers of glucose, ethoxylated ethers, ethoxylated alcohols, alkyl phosphates, polyoxyethylene fatty ether phosphates, fatty acid amides, acyl lactates, soaps, TEA stearate, DEA oleth-3 phosphate, polyethylene glycol 20 sorbitan monolaurate (polysorbate 20), polyethylene glycol 5 soy sterol, steareth-2, steareth-20, steareth-21, ceteth-20, cetearyl glucoside, cetearyl alcohol, C12-13 pareth-3, PPG-2 methyl glucose ether distearate, PPG-5-ceteth-20, bis-PEG / PPG-20 / 20 dimethicone, ceteth-10, polysorbate 80, cetyl phosphate, potassium cetyl phosphate, diethanolamine cetyl phosphate, polysorbate 60, glyceryl stearate, PEG-100 stearate, arachidyl alcohol, arachidyl glucoside, and mixtures thereof.

[0250] In some embodiments, the body care composition comprises one or more silicone-containing compounds. Non-limiting examples of silicone-containing compounds include any member of the family of polymeric products whose molecular backbone consists of alternating silicon and oxygen atoms and side groups attached to the silicon atoms. By varying the -Si-O- chain length, side groups, and crosslinking, silicones can be synthesized into a variety of materials. Their consistency can vary from liquid to gel to solid. Silicone-containing compounds suitable for use in the body care compositions disclosed herein include, but are not limited to, those commonly known to those of ordinary skill in the art. Non-limiting examples include silicone oils (e.g., volatile and non-volatile oils), gels, and solids. In certain embodiments, the silicone-containing compound includes a silicone oil, such as a polyorganosiloxane. Non-limiting examples of polyorganosiloxanes include polydimethylsiloxane, cyclomethicone, polyorganosiloxane-11, phenyltrimethicone, trimethylsilylaminopoly(dimethylsiloxane), stearoxytrimethylsilane, or mixtures of these materials with other silicone materials in any given ratio to achieve the desired consistency and application properties according to the intended application (e.g., for a particular area such as skin, hair, or eyes). "Volatile silicone oils" include silicone oils having a low heat of vaporization, such as less than about 50 calories / gram of silicone oil. Non-limiting examples of volatile silicone oils include cyclomethicone; low-viscosity polydimethylsiloxane, such as polydimethylsiloxane having a viscosity of about 50 cst or less. Other non-limiting volatile silicone oils that can be used in the context of the present invention include those available from manufacturers such as Dow Corning, General Electric, and SWS Silicones.

[0251] In some embodiments, the body care composition comprises one or more exfoliants. Exfoliants comprise ingredients that remove dead skin cells from the outer surface of the skin. These agents can act mechanically, chemically, or otherwise. Non-limiting examples of mechanical exfoliants include abrasives such as pumice, silica, cloth, paper, shells, beads, solid crystals, solid polymers, and the like. Non-limiting examples of chemical exfoliants include acid and enzyme exfoliants. Acids that can be used as exfoliants include, but are not limited to, glycolic acid, lactic acid, citric acid, alpha-hydroxy acids, beta-hydroxy acids, and the like. Other exfoliants known to those skilled in the art can also be considered for use in the context of the body care compositions disclosed herein.

[0252] In some embodiments, the body care composition comprises one or more essential oils. Essential oils include oils extracted from herbs, flowers, trees, and other plants. Such oils typically exist as tiny droplets between plant cells and can be extracted by several methods known to those skilled in the art, such as steam distillation, enfleurage (e.g., by using fat extraction), maceration, solvent extraction, or mechanical pressing. When oils of these types are exposed to air, they tend to evaporate (e.g., volatile oils). Essential oils are generally insoluble in water but soluble in ethanol, ether, fixed oils (vegetable), and other organic solvents. Essential oils are typically named after the plant from which they are extracted. Non-limiting examples of essential oils that can be used in the body care compositions of the present disclosure include sesame oil, macadamia nut oil, tea tree oil, evening primrose oil, Spanish sage oil, Spanish rosemary oil, coriander oil, thyme oil, pimento oil, rose oil, anise oil, balsam oil, bergamot oil, rosewood oil, cedarwood oil, chamomile oil, sage oil, clary sage oil, clove oil, cypress oil, eucalyptus oil, aniseed oil, sea fennel oil, frankincense oil, geranium oil, ginger oil, grapefruit oil, jasmine oil, juniper oil, lavender oil, lemon oil, lemongrass oil, lime oil, mandarin oil, marjoram oil, myrrh oil, neroli oil, orange oil, patchouli oil, pepper oil, black pepper oil, petitgrain oil, pine oil, rose otto oil, rosemary oil, sandalwood oil, spearmint oil, valerian oil, vetiver oil, wintergreen oil, and ylang-ylang. Other essential oils known to those skilled in the art are also considered useful in the context of the present invention.

[0253] In some embodiments, the body care composition comprises one or more thickening agents. Thickening agents, including thickeners or gelling agents, include substances that increase the viscosity of the composition. Thickeners include those that increase the viscosity of the composition while substantially not modifying the efficacy of the active ingredients within the composition. Thickeners can also increase the stability of the composition. Commonly used thickeners include hydrogenated polyisobutene, glyceryl trihydroxystearate, acryloyldimethyltauramide / vp copolymer, or combinations thereof. Other non-limiting examples of additional thickeners that can be used include carboxylic acid polymers, crosslinked polyacrylate polymers, polyacrylamide polymers, polysaccharides, and gums. Examples of carboxylic acid polymers include crosslinked compounds containing one or more monomers derived from acrylic acid, substituted acrylic acids, and salts and esters of these acrylic and substituted acrylic acids, wherein the crosslinking agent contains two or more carbon-carbon double bonds and is derived from a polyol. Examples of commercially available carboxylic acid polymers include carbomers, which are homopolymers of acrylic acid crosslinked with allyl ethers of sucrose or pentaerythritol. Non-limiting examples of crosslinked polyacrylate polymers include cationic and non-ionic polymers. Non-limiting examples are described in U.S. Patent Nos. 5,100,660; 4,849,484; 4,835,206; 4,628,078; 4,599,379. Non-limiting examples of polyacrylamide polymers (including non-ionic polyacrylamide polymers, including substituted branched or unbranched polymers) include polyacrylamide, isoparaffin, and laureth-7, multi-block copolymers of acrylamide and substituted acrylamides with acrylic acid and substituted acrylic acids. Non-limiting examples of polysaccharides include cellulose, carboxymethylhydroxyethyl cellulose, cellulose acetate propionate, hydroxyethyl cellulose, hydroxyethyl ethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, methyl hydroxyethyl cellulose, microcrystalline cellulose, sodium carboxymethyl cellulose, and mixtures thereof. Another example is alkyl-substituted cellulose, where the hydroxyl groups of the cellulose polymer are hydroxyalkylated (e.g., hydroxyethylated or hydroxypropylated) to form hydroxyalkylated cellulose, and then further modified with a C 10 -C 30 linear or branched alkyl via an ether bond. Typically these polymers are C 10 -C 30Ethers of linear or branched alcohols with hydroxyalkyl celluloses. Other useful polysaccharides include scleroglucans, which contain a linear chain of (1 to 3)-linked glucose units, where every third unit has a (1 to 6)-linked glucose. Non-limiting examples of gums that can be used include acacia gum, agar, alginate, alginic acid, ammonium alginate, amylopectin, calcium alginate, calcium carrageenan, carnitine, carrageenan, dextrin, gelatin, gellan gum, guar gum, guar gum hydroxypropyltrimonium chloride, lithium montmorillonite, hyaluronic acid, hydrated silica, hydroxypropyl chitosan, hydroxypropyl guar gum, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, scleroglucan, sodium carboxymethyl dextran, sodium carrageenan, tragacanth gum, xanthan gum, and mixtures thereof.

[0254] In some embodiments, the body care composition comprises one or more preservatives. Non-limiting examples of preservatives that can be used in the context of the present invention include quaternary ammonium preservatives such as polyquaternium-1 and benzalkonium halides (e.g., benzalkonium chloride and benzalkonium bromide), parabens (e.g., methylparaben and propylparaben), phenoxyethanol, benzyl alcohol, chlorobutanol, phenol, sorbic acid, thimerosal, or combinations thereof.

[0255] In some embodiments, the body care composition comprises one or more emollients. Non-limiting examples of suitable emollients include the following: (a) organosilicon oils and their modified products, such as linear and cyclic polydimethylsiloxanes; amino, alkyl, alkylaryl, and aryl organosilicon oils; (b) fats and oils, including natural fats and oils, such as jojoba oil, soybean oil, sunflower oil, rice bran oil, avocado oil, almond oil, olive oil, sesame oil, persic oil, castor oil, coconut oil, mink oil; cocoa butter; beef tallow, lard; hydrogenated oils obtained by hydrogenating the above oils; and synthetic monoglycerides, diglycerides, and triglycerides, such as glyceryl myristate and glyceryl 2-ethylhexanoate; (c) waxes, such as carnauba wax, cetyl wax, beeswax, lanolin and its derivatives; (d) hydrophobic plant extracts; (e) hydrocarbons, such as liquid paraffin, petrolatum, microcrystalline wax, ozokerite, squalene, pristane, and mineral oil; (f) higher fatty acids, such as lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid, lanolinic acid, isostearic acid, arachidonic acid, and polyunsaturated fatty acids (PUFA); (g) higher alcohols, such as lauryl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, cholesterol, and 2-hexyldecanol; (h) esters, such as cetyl octanoate, myristyl lactate, cetyl lactate, isopropyl myristate, myristyl myristate, isopropyl palmitate, isopropyl adipate, butyl stearate, decyl oleate, cholesteryl isostearate, glyceryl monostearate, glyceryl distearate, glyceryl tristearate, alkyl lactate, alkyl citrate, and alkyl tartrate; (i) essential oils and their extracts, such as oils of the genus Mentha, jasmine oil, camphor oil, white cedar oil, bitter orange peel oil, ryu oil, turpentine oil, cinnamon oil, bergamot oil, satsuma mandarin oil, calamus oil, pine oil, lavender oil, laurel oil, clove oil, hiba oil, eucalyptus oil, lemon oil, starflower oil, thyme oil, peppermint oil, rose oil, sage oil, sesame oil, ginger oil, basil oil, juniper oil, lemongrass oil, rosemary oil, rosewood oil, avocado oil, grape oil, grape seed oil, myrrh oil, cucumber oil, watercress oil, calendula oil, elderflower oil, geranium oil, linden flower oil, amaranth oil, seaweed oil, ginkgo oil, ginseng oil, carrot oil, guarana oil, tea tree oil, jojoba oil, comfrey oil, oatmeal oil, cocoa oil, neroli oil, vanilla oil, green tea oil, penny royal oil, aloe oil, menthol, eucalyptol, eugenol, citral, citronella oil, borneol, linalool, geraniol, evening primrose oil, camphor oil, thymol, spirantol oil, penene oil, limonene oil, and terpene oils; (j) lipids, such as cholesterol, ceramides, sucrose esters, and pseudoceramides;(k) Vitamins, minerals and skin nutrients, such as vitamins A, E and K; vitamin alkyl esters, including vitamin C alkyl esters; magnesium, calcium and milk; (l) Sunscreen agents, such as octyl methoxycinnamate and butyl methoxydibenzoylmethane; (l) Phospholipids; (m) Polyhydric alcohols, such as glycerol, propylene glycol, etc.; and polyols, such as polyethylene glycol; (n) Anti-aging compounds, such as alpha-hydroxy acids, beta-hydroxy acids; and (o) Mixtures of any of the foregoing components, etc.;

[0256] In some embodiments, the body care composition comprises one or more thickeners. Non-limiting examples of suitable thickeners include aliphatic hydrocarbon resins, aromatic-modified aliphatic hydrocarbon resins, hydrogenated polycyclopentadiene resins, polycyclopentadiene resins, rosin, rosin esters, gum rosin, gum rosin esters, tall oil rosin, tall oil rosin esters, polyterpenes, aromatic-modified polyterpenes, terpene phenolic resins, aromatic-modified hydrogenated polycyclopentadiene resins, hydrogenated aliphatic resins, hydrogenated aliphatic aromatic resins, hydrogenated terpenes and modified terpenes, hydrogenated abietic acid, hydrogenated rosin esters, polyisoprene, partially or fully hydrogenated polyisoprene, polybutadiene, partially or fully hydrogenated polybutadiene, etc. The thickener can be fully or partially hydrogenated. The thickener can also be non-polar, and non-polar means that the thickener is substantially free of monomers having polar groups. In some embodiments, there are no polar groups. In some embodiments, the polar groups are present in an amount of at most about 5 wt%, preferably at most about 2 wt%, more preferably at most about 0.5 wt%.

[0257] In some embodiments, the body care composition comprises one or more colorants, such as pigments or dyes. Examples of suitable pigments include, but are not limited to, inorganic pigments, organic pigments, lakes, pearlescent pigments, iridescent or optically variable pigments, and mixtures thereof. The term "pigment" should be understood to mean inorganic or organic, white or colored particles. Within the scope of the present invention, the pigments can be surface-treated as appropriate, but are not limited to treatments such as silicone, perfluorinated compounds, lecithin and amino acids.

[0258] In some embodiments, the body care composition comprises one or more surfactants. Surfactants that can be used as the surfactant component in the compositions disclosed herein include nonionic, anionic, cationic and amphoteric (zwitterionic) surfactants and can be used in combination with each other.

[0259] In some embodiments, the body care composition comprises one or more pH regulators. pH regulators include inorganic and organic acids and bases, particularly ammonia water, citric acid, phosphoric acid, acetic acid, sodium hydroxide, lactic acid, levulinic acid, glycolic acid, tartaric acid, malic acid, pyrrolidonecarboxylic acid (PCA), succinic acid, citric acid, glutamic acid, 2-amino-2-methyl-1-propanol (AMP) and triethanolamine (TEA).

[0260] In some embodiments, the body care composition comprises one or more reducing agents. Suitable reducing agents include, but are not limited to, thiourea, thiosulfates, sulfites, bisulfites, metabisulfites, salts of borohydrides and hypophosphites (such as sodium salts), ascorbic acid and its salts, esters and derivatives (such as ascorbyl palmitate and ascorbyl polypeptides), and tocopherols and their salts, esters and derivatives (such as tocopheryl acetate). Other well-known reducing agents can also be used, such as those listed in the INCI handbook.

[0261] In some embodiments, the body care composition comprises one or more foaming agents. Foaming agents include, for example, sodium lauryl sulfate, sodium lauroyl sarcosinate, sodium alkyl sulfosuccinate, sodium coconut monoglyceride sulfonate, sodium α-olefin sulfonate, N-acyl amino acid salts such as N-acyl glutamate salts, 2-alkyl-N-carboxymethyl-N-hydroxyethyl imidazoline betaine, maltitol fatty acid esters, sucrose fatty acid esters, polyglycerol fatty acid esters, fatty acid diethanolamides, polyoxyethylene sorbitan monostearate, polyoxyethylene hydrogenated castor oil, and polyoxyethylene fatty acid esters. These foaming agents can be used alone or in combination of two or more.

[0262] In some embodiments, the body care composition comprises one or more tanning agents. Suitable tanning agents include, but are not limited to, α-hydroxy aldehydes and ketones, glyceraldehyde and related aldoses, various indoles, imidazoles and their derivatives, and various approved pigmenting agents. Other suitable tanning agents include, but are not limited to, methylglyoxal, glyceraldehyde, erythrulose, alloxan, 2,3-dihydroxy succinaldehyde, 2,3-dimethoxy succinaldehyde, 2-amino-3-hydroxy-succinaldehyde, and 2-benzylamino-3-hydroxy succinaldehyde.

[0263] In some embodiments, the body care composition comprises one or more astringents. Suitable astringents include, but are not limited to, aluminum citrate, aluminum lactate, birch extract, coffee extract, evening primrose extract, grape extract, henna extract, ivy extract, lemon extract, witch hazel extract, ammonium alum and potassium alum, aluminum triphosphate, aluminum glycinate and aluminum phenolsulfate, alcloxa, aldioxa, aluminum stearate, aluminum sulfate and aluminum citrate, sodium aluminum phosphate, sodium alum, sodium aluminum chlorohydroxy lactate, calcium lactate, calcium chloride, calcium sulfate hydrate, sodium aluminum lactate, zinc acetate, zinc chloride, zinc sulfate, zinc lactate, zinc zeolite, zinc phenolsulfonate, and combinations thereof.

[0264] In some embodiments, the body care composition comprises one or more antiseptics. Suitable antiseptics include, but are not limited to, methyl, ethyl, propyl or butyl parabens, phenoxyethanol, o-phenylphenol, dehydroacetic acid or its salts, p-cresol, m-cresol, o-chloro-m-xylenol, peppermint oil, Echinacea, bloodroot, cayenne, tea tree oil, wild bergamot, chaparral, stinging nettle, laurel, myrrh, garcinia bark, toothache tree, calendula, chamomile, mupirocin, neomycin sulfate, bacitracin, polymyxin B, 1-ofloxacin, tetracyclines (chlortetracycline hydrochloride, oxytetracycline hydrochloride and tetrachcycline hydrochloride) hydrochoride), clindamycin phosphate, gentamicin sulfate, benzalkonium chloride, benzethonium chloride, hexylresorcinol, methylbenzethonium chloride, phenol, quaternary ammonium compounds, triclocarban, triclosan, and tea tree oil.

[0265] In some embodiments, the body care composition comprises one or more deodorants or antiperspirants. Suitable antiperspirants and deodorants include, but are not limited to, zinc salts such as zinc sulfate and zinc chloride, glycinates such as aluminum zirconium glycinate, aluminum chlorohydrate, aluminum zirconium tetrachloride hydrate, zinc carbonate, o-phenylphenol, and quaternary ammonium compounds such as dimethylbenzylammonium chloride and hexamethonium chloride.

[0266] In some embodiments, the body care composition comprises one or more lightening agents. Examples of lightening agents include, but are not limited to, hydroquinone, kojic acid, licorice or its derivatives, ascorbic acid or its derivatives, arbutin, bearberry extract, Glycyrrhiza glabra and its derivatives, Chlorella vulgaris extract, Perilla extract, coconut extract, and / or other decolorizing agents.

[0267] In some embodiments, the body care composition comprises one or more biocides. Examples of biocides include, but are not limited to, triclosan, 3,4,4'-trichlorocarbanilide (triclocarban); 3,4,4'-trifluoromethyl-4,4'-dichlorocarbanilide (chlorofluorocarban); 5-chloro-2-methyl-4-isothiazolin-3-one; iodopropynyl butylcarbamate; 8-hydroxyquinoline; 8-hydroxyquinoline citrate; 8-hydroxyquinoline sulfate; 4-chloro-3,5-dimethylphenol (chloroxylenol); 2-bromo-2-nitropropane-1,3-diol; diazolidinyl urea; butoconazole; nystatin; terconazole; nitrofurantoin; phenazopyridine; acyclovir; clortrimazole; chloroxylenol; chlorhexidine; miconazole; terconazole; butylparaben; ethylparaben; methylparaben; methylchloroisothiazolinone; methylisothiazolinone; a mixture of 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin and 3-iodo-2-propynyl butylcarbamate; hydroxyquinoline; EDTA (ethylenediaminetetraacetic acid); EDTA tetrasodium; parabens; alkylpyridinium compounds; cocoyl phosphatidyl PG-dimonium chloride; chlorhexidine gluconate; chlorhexidine digluconate; chlorhexidine acetate; chlorhexidine hydroxyethylsulfate; chlorhexidine hydrochloride; benzalkonium chloride; benzethonium chloride; polyhexamethylene biguanide; and mixtures thereof.

[0268] Other ingredients commonly used in body care compositions such as skin care or hair care products may also be included.

[0269] In some embodiments, the body care product is a shampoo, body wash, soap, exfoliating scrub, moisturizer, facial serum, antiperspirant, deodorant, body lotion, body oil, sunscreen, or bronzer.

[0270] In some embodiments, the body care product is a personal care or beauty product. Personal care and beauty products include products that can be applied to the skin, hair, and nails, and can be leave-on products or rinse-off products. In the context of the present disclosure, "rinse-off" means that the intended use of the product includes application to the skin and / or hair, followed by rinsing off or wiping away the product from the skin or hair within seconds to minutes of the application step. Personal care and beauty products include powders, creams, emulsions, lotions, gels, and oils for application to the skin (face, hands, feet, etc.), coloring bases (liquids and pastes), and liquid-impregnated tissues; products for applying and removing makeup on the face and eyes; hair care products, including hair tints and hair bleaches; products for perming, straightening, styling, and setting hair; shaving products, including creams, foam mousses, and hair removal products; sunless tanning products and products for tanning without sunlight; deodorant and antiperspirant products.

[0271] In some embodiments, the personal care or beauty product is selected from the group consisting of: shaving aids, shampoos, hair care products, leave-on skin care products, skin cleansing or washing products (e.g., rinse-off skin cleansing or washing products), wet wipes, and body sprays, deodorants or antiperspirants. Shaving aids specifically include foams, gels, creams, and soap bars (see, for example, U.S. Patent Nos. 7,069,658; 6,944,952; 6,594,904; 6,182,365; 6,185,822; 6,298,558; and 5,113,585). Shampoos and hair conditioners specifically include 2-in-1 shampoos and shampoos formulated for dry or oily hair, or shampoos containing additives such as antidandruff agents. Hair care products can be rinse-off or leave-on hair care products, and also include hair tonics, hair bleaches, hair colorants, setting and styling products. See, for example, U.S. Patent Nos. 6,162,423; 5,968,286; 5,935,561; 5,932,203; 5,837,661; 5,776,443; 5,756,436; 5,661,118; 5,618,523. Leave-on skin care products include eaux de toilette, eau de parfum, cologne, wet wipes, body sprays, deodorants, and antiperspirants. Skin washing products specifically include beauty and hygiene soap bars, shower gels, liquid soaps, bath liquids, exfoliating gels and pastes (see, for example, U.S. Patent Nos. 3,697,644; 4,065,398; 4,387,040). Wet wipes specifically include skin cleansing wipes, baby wipes, makeup removing wipes, and skin freshening wipes (see, for example, U.S. Patent No. 4,775,582; WO 02 / 07701; WO 2007 / 069214; and WO 95 / 16474). Body sprays, deodorants, and antiperspirants specifically include stick forms, liquid roll-on applicators, and pressurized sprays.

[0272] The compositions and consumer products according to the present disclosure will be further illustrated by the following non-limiting examples.

[0273] Examples

[0274] Unless otherwise indicated, the percentages (%) and ratios indicated in the examples are weight percentages and weight ratios.

[0275] Example 1. Solvent Comparison

[0276] Several solvents and solvent blends were prepared, and then a measured amount of naringenin was added and mechanically stirred. The dissolution of each mixture was then visually observed. The results are summarized in Table 1 below. All samples were stored in the dark at room temperature and re-evaluated for stability after three months.

[0277] Table 1.

[0278]

[0279] ×: Dissolved

[0280] ○: Partially dissolved, precipitate observed

[0281] #: Not dissolved

[0282] *: Reprecipitation

[0283] Example 2. Exemplary Compositions

[0284] The following Tables 2 and 3 show exemplary compositions according to some forms of the present invention.

[0285] Table 2.

[0286]

[0287] Table 3.

[0288]

[0289] Example 3. Solubility of Naringenin at 25 °C

[0290] Naringenin was mixed with different solvents and solvent mixtures and then transferred to an 8 mL vial equipped with an overhead stirrer. The samples were placed in a Crystalline PV instrument (Technobis, Netherlands). The heating step was carried out at a heating rate of +0.1 °C / min under mechanical stirring, and the samples were monitored by tracking the transparency of the LED beam passing through the vial. When naringenin was completely dissolved in the solvent, complete (100%) transparency was achieved. On the other hand, when the measured transparency value was below 100%, the dissolution process was still incomplete. Once the signal reached 100% transparency, the dissolution process was complete, and the corresponding temperature was regarded as the dissolution temperature.

[0291] For each solvent or solvent mixture, the relationship between the measured solubility and temperature was fitted to an exponential function. The solubility at 25 °C was obtained by extrapolating or interpolating this exponential function.

[0292] Table 4.

[0293]

[0294] Example 4. Solubility of Phloretin at 25 °C

[0295] The solubility of phloretin at 25 °C was determined using the same method as in Example 3.

[0296] Table 5.

[0297]

[0298] Example 5. Stability of Naringenin Solution

[0299] Naringenin was mixed with different solvents and heated until the product was completely dissolved. Subsequently, the samples were cooled to room temperature and stored for three months.

[0300]

[0301] ×: Dissolved

[0302] *: Reprecipitated

[0303] The disclosed subject matter has been described with reference to the specific details of particular embodiments. These details should not be regarded as limiting the scope of the disclosed subject matter unless such details are included in the appended claims.

[0304] Accordingly, the exemplary embodiments described herein are well suited to attaining the above - mentioned objects and advantages, as well as those inherent therein. The specific embodiments disclosed above are merely illustrative, as the exemplary embodiments described herein may be modified and practiced in different but equivalent manners, which will be apparent to those of ordinary skill in the art who have benefited from the teachings herein. Additionally, the details of the construction or design shown herein have no limitations other than those described in the following claims. Thus, it is evident that the specific illustrative embodiments disclosed above may be altered, combined, or modified, and all such variations are considered to be within the scope and spirit of the exemplary embodiments described herein. The exemplary embodiments disclosed herein may be appropriately practiced without the presence of any element not specifically disclosed herein and / or any optional element disclosed herein.

Claims

1. A liquid composition comprising: a) A compound of formula (I) or a salt thereof, wherein: R 1 is a hydrogen atom, -OH or -O-R 1A ; R 1A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 1A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties; R 2 is a hydrogen atom, -OH or -O-R 2A ; R 2A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy, or R 2A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties; R 3 is -OH or -O-R 3A ; R 3A is C 1-6 alkyl, which may optionally be substituted one or more times by substituents selected from -OH and C 1-6 alkoxy; or R 3A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties; R 4 is a hydrogen atom, -OH or -O-R 4A ; R 4A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 4A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties; R 5 is a hydrogen atom, -OH, -O-R 5A or -OC(O)-R 5B ; R 5A is C 1-6 alkyl, which may optionally be substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 5A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties; R 5B is -H or C 1-6 alkyl, which is optionally substituted one or more times by substituents selected from -OH and C 1-6 alkoxy; R 6 and R 7 are independently selected from C 1-6 alkyl, -OH, C 1-6 alkoxy, and -O-(C 1-6 alkylene)-O-(C 1-6 alkyl); m is 0, 1 or 2; and n is 0, 1, 2 or 3; or A compound of formula (II) or a salt thereof, wherein: R 8 is a hydrogen atom, -OH or -O-R 8A ; R 8A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 8A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties; R 9 is a hydrogen atom, -OH or -O-R 9A ; R 9A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy, or R 9A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties; R 10 is -OH or -O-R 10A ; R 10A is C 1-6 alkyl, which may optionally be substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 10A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties; R 11 is a hydrogen atom, -OH or -O-R 11A ; R 11A is C 1-6 alkyl, which is optionally substituted one or more times by substituents selected from -OH and C 1-6 alkoxy; or R 11A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties; R 12 is a hydrogen atom, -OH, -O-R 12A or -OC(O)-R 12B ; R 12A is C 1-6 alkyl, which is optionally substituted one or more times with substituents selected from -OH and C 1-6 alkoxy; or R 12A is a glucuronic acid moiety, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to five sugar moieties, which are linked by glycosidic bonds and are independently selected from furanose moieties and pyranose moieties; R 12B is -H or C 1-6 alkyl, which is optionally substituted one or more times by substituents selected from -OH and C 1-6 alkoxy; R 13 and R 14 are independently selected from C 1-6 alkyl, -OH, C 1-6 alkoxy, and -O-(C 1-6 alkylene)-O-(C 1-6 alkyl); m' is 0, 1 or 2; and n' is 0, 1, 2 or 3; or a combination thereof; b) An oil containing carvone; and c) An optionally used solvent; wherein, based on the total weight of the composition, the amount of the compound of formula (I) and / or (II) is at least 7% by weight.

2. The liquid composition according to claim 1, wherein the composition is a clear and homogeneous solution.

3. The liquid composition according to claim 1 or 2, wherein the liquid composition contains a compound of formula (I).

4. The liquid composition according to claim 3, wherein R 5 is a hydrogen atom or -OC(O)-R 5B , typically wherein R 5B is C 1-6 alkyl.

5. The liquid composition according to claim 4, wherein R 1 is -OH or -O-R 1A , R 2 is -OH or -O-R 2A , R 3 is -OH or -O-R 3A , R 4 is -OH or -O-R 4A , m is 0, and n is 0.

6. The liquid composition according to claim 1 or 2, wherein the liquid composition contains a compound of formula (II).

7. The liquid composition according to claim 6, wherein R 12 is a hydrogen atom.

8. The liquid composition according to claim 7, wherein R 8 is -OH or -O-R 8A , R 9 is -OH or -O-R 9A , R 10 is -OH or -O-R 10A , R 11 is -OH or -O-R 11A , m' is 0, and n' is 0.

9. The liquid composition according to any one of claims 1 to 8, wherein the oil containing carvone is pure carvone, spearmint oil, caraway seed oil or dill oil.

10. The liquid composition according to any one of claims 1 to 9, wherein the composition contains a solvent selected from the group consisting of 1-propanol, 2-propanol, ethanol, 1,2-propanediol, triethyl citrate, glyceryl triacetate, glycerol, 1,3-propanediol, ethyl lactate and benzyl alcohol.

11. A consumer product comprising the liquid composition according to any one of claims 1 to 10.

12. The consumer product according to claim 11, further comprising at least one cooling compound, typically wherein the at least one cooling compound is selected from the group consisting of: (-)-menthol, N-ethyl-p-menthan-3-carboxamide, cubebol, isopulegol, 3-(L-menthoxy)propane-1,2-diol, cis / trans-p-menthane-3,8-diol, 3-(L-menthoxy)-2-methylpropane-1,2-diol, 2-[2-(p-menthan-3-yloxy)ethoxy]ethanol, menthoxyethanol, (1R,2R,4R)-1-(2-hydroxy-4-methylcyclohexyl)ethenone, (1R,2R,5R)-N-ethyl-5-methyl-2-(prop-1-en-2-yl)cyclohexanecarboxamide, N-(3-hydroxy-4-methoxyphenyl)-2-isopropyl-5,5-dimethylcyclohexanecarboxamide, N-[4-(cyanomethyl)phenyl]-2-isopropyl-5,5-dimethylcyclohexanecarboxamide, N-(2-hydroxy-2-phenylethyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide, L-menthyl lactate, (-)-menthyl glycol carbonate, (-)-menthone 1,2-glycerol ketal, D / L-menthone 1,2-glycerol ketal, (-)-menthyl 1-propylene glycol carbonate, (-)-menthyl 2-propylene glycol carbonate, D / L-menthyl 1-propylene glycol carbonate, D / L-menthyl 2-propylene glycol carbonate, (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide, menthyl ethylamide oxalate, (E)-3-benzo[1,3]dioxol-5-yl-N,N-diphenyl-2-propenamide, 3,4-methylenedioxycinnamic acid, N,N-diphenylamide, N,N-dimethyl(-)-menthyl succinimide, (1R,2S,5R)-N-(4-(carbamoylmethyl)phenyl)-menthylcarboxamide, (-)-menthyl pyrrolidonecarboxylate, L-norephedrine p-menthanecarboxamide, (1R,2S,5R)-N-(4-(cyanomethyl)phenyl)menthylcarboxamide, (1R,2S,5R)-N-(2-(pyridin-2-yl)ethyl)menthylcarboxamide, 6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]Decan-2-one, (1R,2R,4S)-dihydroumbellulol, N-ethyl-p-menthane-3-carboxamide, 2-isopropyl-N,2,3-trimethylbutanamide, ethyl 3-(p-menthane-3-carboxamido)acetate, N-ethyl-2,2-diisopropylbutanamide, N-(1,1-dimethyl-2-hydroxyethyl)-2,2-dimethylbutanamide, N-cyclopropyl-5-methyl-2-isopropyl-cyclohexanecarboxamide, (-)-menthyl acetoacetate, (-)-menthyl succinate, (-)-menthyl (S)-3-hydroxybutyrate, (-)-menthyl glutarate, 1-[2-hydroxyphenyl]-4-[2-nitrophenyl]-1,2,3,6-tetrahydropyrimidin-2-one, di-(-)-menthyl glutarate, N-(2-hydroxyethyl)-2,3-dimethyl-2-isopropylbutanamide, and any combination thereof.

13. The consumer product according to claim 11 or 12, which further comprises at least one cooling enhancing compound, typically wherein the at least one cooling enhancing compound is selected from the group consisting of: N-ethyl-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide; N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide; 2-(4-fluorophenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide; 2-(2-hydroxy-4-methylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide; 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide; 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiazol-5-ylmethyl)-acetamide; 5-methoxy-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)benzofuran-2-carboxamide; 2-(4-ethylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide; (E / Z)-2-methyl-2-butenal; (E / Z)-2-isopropyl-5-methyl-2-hexenal; and any combination thereof.

14. The consumer product according to any one of claims 11 to 13, which further comprises a sweetener.

15. The consumer product according to any one of claims 11 to 14, wherein the consumer product is a flavored product, typically a food product, a beverage product, an oral care product or a pharmaceutical product; or a body care product, typically a cosmetic, a skin care product or a hair care product.

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