# US 2019/0169111 A1 · Warming sensation compounds

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- Number: US 2019/0169111 A1
- Document ID: US20190169111A1
- Status: Published application
- Kind: A1
- Application number: 16/314,920
- Filed: 2017-08-04
- Published: 2019-06-06
- Earliest claimed: 2016-08-04
- Assignees: Takasago International Corporation
- Applicants: Takasago International Corporation
- Inventors: Thalia S. Dickerson; Louis J. Lombardo; Michael E. Lankin; Jennifer B. Tartaglia
- Web page: https://patentgrep.com/patent/US20190169111A1

## CPC

- C07C 69/734: Ethers
- A23G 1/32: characterised by the composition {containing organic or inorganic compounds}
- A23G 1/42: containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins (containing dairy products A23G1/46)
- A23G 4/06: characterised by the composition {containing organic or inorganic compounds}
- A23G 4/12: containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins (containing dairy products A23G4/16)
- C07C 69/732: of unsaturated hydroxy carboxylic acids
- A23L 27/204: {Aromatic compounds}
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- A23V 2200/15: Flavour affecting agent
- A61K 8/37: Esters of carboxylic acids
- A61K 8/42: Amides
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A23G: COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

Novel compounds for use in flavor, fragrance, or topical compositions are provided. Specifically, the compounds of the presently disclosed subject matter provide effective and unexpected warming sensations. The composition can be incorporated into various consumer end products, including flavors, fragrances, and topical applications.

## Claims

### Claim 1

A compound represented by Formula (I):
wherein
R1 is a hydrogen atom, a methyl group, or an ethyl group;
R2, R3, R4, R5, and R6 are each independently a hydrogen atom, a linear or branched alkyl or alkenyl group from 1 to 5 carbons, an alkoxy group, a hydroxyl group, a substituted or unsubstituted phenyl group, or where R3 and R4 together are selected from a group consisting of —OCH2O—, —OCH2CH2—, —OCH2CH2O—, or —OCH2CH2CH2—;
X is group containing one to five linear or branched carbon atoms;
Y is represented by an oxygen atom or a group represented by (CH2)m where m is equal to 0 or 1;
provided that when:
R1 is a methyl group
X is a group containing from two to five linear or branched carbon atoms and
Y is a group represented by (CH2)m, then
R2, R3, R4, R5, and R6 are all not a hydrogen atom or a linear or branched alkyl or alkenyl group.

### Claim 2

A compound represented by Formula (II)
wherein
the dashed line represents a single or double bond,
R7 and R8 are each independently a hydrogen atom, a methyl group, or an ethyl group,
R9 is a linear or branched alkyl or alkenyl group containing 4 to 12 carbon atoms, provided that when R8 is a hydrogen atom that R9 is not chosen from the group represented by Formula (Z)
where n is an integer from 0 to 7 and A and B are each independently a hydrogen atom, a methyl group, or an ethyl group.

### Claim 3 (depends on 1)

A warming composition comprising one or more compounds according to claim 1.

### Claim 4 (depends on 3)

The warming composition of claim 3 comprising 2-Phenoxyethyl 2-(4-hydroxy-3-methoxyphenyl)acetate, (E)-3,7-Dimethylocta-2,6-dien-1-yl 2-(4-hydroxy-3-methoxyphenyl)acetate, or mixtures thereof.

### Claim 5 (depends on 3)

A warming composition according to claim 3, further comprising at least one additional warming agent.

### Claim 6 (depends on 5)

A warming composition according to claim 5, wherein the at least one warming agent is selected from the group consisting of vanillyl ethyl ether, vanillyl propyl ether, vanillin propylene glycol acetal, ethyl vanillin propylene glycol acetal, capsaicin, gingerol, vanillyl butyl ether, 4-(1-menthoxy-methyl)-2-phenyl-1,3-dioxolane, 4-(1-menthoxy-methyl)-2-(3′,4′-dihydroxy-phenyl)-1,3-dioxolane, 4-(1-menthoxy-methyl)-2-(2′-hydroxy-3′-methoxy-phenyl)-1,3-dioxolane, 4-(1-menthoxy-methyl)-2-(4′-methoxyphenyl)-1,3-dioxolane, 4-(1-menthoxy-methyl)-2-(3′,4′-methylenedioxy-phenyl)-1,3-dioxolane, black pepper extract, cinnamaldehyde, piperine, hot pepper oil, red pepper oleoresin, capsicum oleoresin, ginger oleoresin, nonyl acid vanillylamide, 4-(1-menthoxy-methyl)-2-(3′-methoxy-4′-hydroxyphenyl)-1,3-dioxolane, vanillin-1,2-hexylene glycol acetal, vanillin-1,2-butylene glycol acetal, vanillin-1-butoxyglycerol acetal, ethyl vanillin, ethyl vanillyl alcohol (3-ethoxy-4-hydroxybenzyl alcohol), ethyl homovanillate, vanillyl isopropyl ether, and all stereoisomers and mixtures thereof.

### Claim 7 (depends on 3)

A warming composition according to claim 3, wherein the warming composition is formulated as a flavor, fragrance or topical composition.

### Claim 8 (depends on 3)

A flavor or fragrance composition comprising the warming composition according to claim 3.

### Claim 9 (depends on 8)

The flavor or fragrance composition of claim 8, further comprising at least one non-warming trigeminal stimulating agent.

### Claim 10 (depends on 9)

The flavor or fragrance composition of claim 9, wherein the non-warming trigeminal stimulating compound is selected from the group consisting of menthol, menthone, camphor, pulegol, isopulegol, cineole, 2-isopropyl-N-2,3-trimethylbutyramide, N-ethyl-2-isopropyl-5-methylcyclohexane carboxamide, ethyl 3-(p-menthane-3-carboxamido)acetate, N-(4-methoxyphenyl)-p-menthanecarboxamide, N-ethyl-2,2-diisopropylbutanamide, N-cyclopropyl-5-methyl-2-isopropylcyclohexanecarboxamide, N-(1,1-dimethyl-2-hydroxyethyl)-2,2-diethylbutanamide, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, N-(2-(Pyridin-2-yl)ethyl)-3-p-menthanecarboxamide, N-(2-hydroxyethyl)-2-isopropyl-2,3-dimethylbutanamide, cyclopropanecarboxylic acid (2-isopropyl-5-methyl-cyclohexyl)-amide, N-[4-(2-Amino-2-oxoethyl)phenyl]-p-menthanecarboxamide, menthyl pyrrolidone carboxylate, cubebol, icilin, 1-(2-hydroxy-4-methylcyclohexyl)ethanone, N-(4-(cyanomethyl)phenyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide, 2-isopropyl-5-methylcyclohexyl 4-(dimethylamino)-4-oxobutanoate, N-benzo[1,3] dioxol-5-yl-3-p-menthanecarboxamide, N-benzooxazol-4-yl-3-p-menthanecarboxamide, N-4-([1,2,4]triazol-1-yl)-phenyl-3-p-menthanecarboxamide, N-4-(pyrazol-1-yl)-phenyl-3-p-menthanecarboxamide, N-(1-isopropyl-1,2-dimethylpropyl)-1,3-benzodioxole-5-carboxamide, N-(1-methyl-1-isopropylbutyl)benzamide, fenchyl-N,N-diemethylsuccinamide, fenchyl monosuccinate, ethyl fenchyl malonate, bornyl monosuccinate, isobornyl monosuccinate, menthyl 3-oxobutyrate, menthyl 3-oxopentanoate, 3-1-menthoxypropane-1,2-diol, 3-1-menthoxy-2-methylpropane-1,2-diol, p-menthane-3,8-diol, 2-1-menthoxyethan-1-ol, 3-1-menthoxypropan-1-ol, 4-1-menthoxybutan-1-ol, menthyl 3-hydroxybutyrate, 6-isopropyl-9-methyl-1,4-dioxaspiro-(4,5)-decane-2-methanol, 2-[(2-p-menthoxy)ethoxy]ethanol, menthyl succinate, menthyl glutarate, dimenthyl succinate, dimenthyl glutarate, menthyl lactate, menthone glycerin ketal, mint oil, peppermint oil, spearmint oil, eucalyptus oil, spilanthol, sanshool, hydroxy y-sanshool, hydroxy-sanshool, sanshool-I, sanshool II, sanshoamide, Japanese pepper extract, chavicine, echinacea extract, northern prickly ash extract, Nepalese spice timur extract, 4-(1-menthoxymethyl)-2-phenyl-1, 3-dioxolane, N-isobutyldeca-(2,4)-dienamide, N-cyclopropyl-(2E,6Z)-nonadienamide, N-ethyl-(2E,6Z)-nonadienamide, jambu oleoresin, allyl-isothiocyanate, 4-hydroxybenzyl isothiocyanate, mustard oil, wasabi extract, elemol, elimicin, lime oxide, elemi oil, ocimene quintoxide, 2-isopropenyl-5-methyl-5-vinyltetrahydrofuran, and all stereoisomers and mixtures thereof.

### Claim 11 (depends on 10)

The flavor or fragrance composition of claim 10, wherein the non-warming trigeminal stimulating compound is selected from the group consisting of menthol, menthone, camphor, pulegol, isopulegol, 2-isopropyl-N-2,3-trimethylbutyramide, N-ethyl-2-isopropyl-5-methylcyclohexane carboxamide, ethyl 3-(p-menthane-3-carboxamido)acetate, 1-(2-hydroxy-4-methylcyclohexyl)ethanone, N-(4-(cyanomethyl)phenyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide, menthyl 3-oxobutyrate, menthyl 3-oxopentanoate, 3-1-menthoxypropane-1,2-diol, 3-1-menthoxy-2-methylpropane-1,2-diol, p-menthane-3,8-diol, 2-1-menthoxyethan-1-ol, 3-1-menthoxypropan-1-ol, 4-1-menthoxybutan-1-ol, menthyl 3-hydroxybutyrate, menthyl succinate, menthyl glutarate, dimenthyl succinate, dimenthyl glutarate, menthyl lactate, menthone glycerin ketal, mint oil, peppermint oil, spearmint oil, eucalyptus oil, spilanthol, Japanese pepper extract, chavicine, echinacea extract, northern prickly ash extract, Nepalese spice timur extract, 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane, N-isobutyldeca-(2,4)-dienamide, N-ethyl-(2E,6Z)-nonadienamide, jambu oleoresin, allyl-isothiocyanate, mustard oil, wasabi extract, elemol, elimicin, lime oxide, elemi oil, and all stereoisomers and mixtures thereof.

### Claim 12 (depends on 3)

A topical composition comprising the warming composition according to claim 3.

### Claim 13 (depends on 12)

The topical composition of claim 12, further comprising at least one non-warming trigeminal stimulating agent.

### Claim 14 (depends on 3)

A consumer product comprising: (a) a warming composition according to claim 3; and (b) a consumer product base.

### Claim 15 (depends on 8)

A consumer product comprising: (a) at least one flavor or fragrance composition according to claim 8; and (b) a consumer product base.

### Claim 16 (depends on 1)

A method to improve, enhance or modify the taste or odor properties of a flavor or fragrance composition by adding to said composition an effective quantity of one or more of the compounds according to claim 1.

### Claim 17 (depends on 16)

The method of claim 16, wherein the compound of Formula (I) is effective to produce a warming sensation after contact with the skin or mucous membrane of an individual.

### Claim 18 (depends on 2)

A warming composition comprising one or more compounds according to claim 2.

### Claim 19 (depends on 2)

A method to improve, enhance or modify the taste or odor properties of a flavor or fragrance composition by adding to said composition an effective quantity of one or more of the compounds according to claim 2.

### Claim 20 (depends on 19)

The method of claim 19, wherein the compound of Formula (II) is effective to produce a warming sensation after contact with the skin or mucous membrane of an individual.