Methyl menthol derivative and cooling agent composition containing same

Patent metadata

Field	Value
Publication number	US-10494330-B2
Application number	US-201615559762-A
Country	US
Kind code	B2
Filing date	Mar 24, 2016
Priority date	Mar 25, 2015
Publication date	Dec 3, 2019
Grant date	Dec 3, 2019

Abstract

The purpose of the present invention is to provide a cooling agent composition containing a novel methyl menthol derivative having no undesirable feeling of stimulation, malodor, bitterness, or the like, it being possible to use the cooling agent composition as a cooling agent or sensory stimulation agent having exceptional persistence of a sense of coolness and refreshing feeling. The present invention pertains to a cooling agent composition containing a methyl menthol derivative represented by general formula (1A) or general formula (1B).

First claim

The invention claimed is:

1. A cooling agent composition, comprising a methyl menthol compound which is selected from the following group:

2. The cooling agent composition according to claim 1 , further comprising at least one cool feeling substance other than the methyl menthol compound.

3. The cooling agent composition according to claim 2 , wherein the cool feeling substance other than the methyl menthol compound is at least one cool feeling substance selected from the group consisting of:
one or more kinds of compounds selected from menthol, menthone, camphor, pulegol, isopulegol, cineole, cubenol, menthyl acetate, pulegyl acetate, isopulegyl acetate, menthyl salicylate, pulegyl salicylate, isopulegyl salicylate, 3-(1-menthoxy)propan-1,2-diol, 2-methyl-3-(1-menthoxy)propan-1,2-diol, 2-(1-menthoxy)ethan-1-ol, 3-(1-menthoxy)propan-1-ol, 4-(1-menthoxy)butan-1-ol, menthyl 3-hydroxybutanoate, menthyl glyoxylate, p-menthane-3,8-diol, 1-(2-hydroxy-4-methylcyclohexyl)ethanone, menthyl lactate, menthone glycerin ketal, menthyl-2-pyrrolidone-5-carboxylate, monomenthyl succinate, alkali metal salts of monomenthyl succinate, alkaline earth metal salts of monomenthyl succinate, monomenthyl glutarate, alkali metal salts of monomenthyl glutarate, alkaline earth metal salts of monomenthyl glutarate, N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine, p-menthane-3-carboxylic acid glycerol ester, menthol propylene glycol carbonate, menthol ethylene glycol carbonate, p-menthane-2,3-diol, 2-isopropyl-N,2,3-trimethylbutanamide, N-ethyl-p-menthane-3-carboxamide, ethyl 3-(p-menthane-3-carboxamide)acetate, N-(4-methoxyphenyl)-p-menthanecarboxamide, N-ethyl-2,2-diisopropylbutanamide, N-cyclopropyl-p-menthanecarboxamide, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, N-(2-pyridin-2-yl)-3-p-menthanecarboxamide, N-(2-hydroxyethyl)-2-isopropyl-2,3-dimethylbutanamide, N-(1,1-dimethyl-2-hydroxyethyl)-2,2-diethylbutanamide, cyclopropanecarboxylic acid (2-isopropyl-5-methylcyclohexyl)amide, N-ethyl-2,2-diisopropylbutanamide, N-[4-(2-amino-2-oxoethyl)phenyl]-p-menthanecarboxamide, 2-[(2-p-menthoxy)ethoxy]ethanol, 2,6-diethyl-5-isopropyl-2-methyltetrahydropyran, and trans-4-tert-butylcyclohexanol;
one or more sugar alcohols selected from the group consisting of xylitol, erythritol, dextrose, and sorbitol; and
one or more natural products selected from the group consisting of Japanese mint oil, peppermint oil, spearmint oil, and eucalyptus oil.

4. A sensory stimulant composition, comprising the cooling agent composition according to claim 1 .

5. The sensory stimulant composition according to claim 4 , further comprising at least one warm feeling substance.

6. The sensory stimulant composition according to claim 5 , wherein the warm feeling substance is at least one warm feeling substance selected from the group consisting of:
one or more compounds selected from the group consisting of vanillyl methyl ether, vanillyl ethyl ether, vanillyl propyl ether, vanillyl isopropyl ether, vanillyl butyl ether, vanillyl amyl ether, vanillyl isoamyl ether, vanillyl hexyl ether, isovanillyl methyl ether, isovanillyl ethyl ether, isovanillyl propyl ether, isovanillyl isopropyl ether, isovanillyl butyl ether, isovanillyl amyl ether, isovanillyl isoamyl ether, isovanillyl hexyl ether, ethyl vanillyl methyl ether, ethyl vanillyl ethyl ether, ethyl vanillyl propyl ether, ethyl vanillyl isopropyl ether, ethyl vanillyl butyl ether, ethyl vanillyl amyl ether, ethyl vanillyl isoamyl ether, ethyl vanillyl hexyl ether, vanillin propylene glycol acetal, isovanillin propylene glycol acetal, ethyl vanillin propylene glycol acetal, vanillyl butyl ether acetic acid ester, isovanillyl butyl ether acetic acid ester, ethyl vanillyl butyl ether acetic acid ester, 4-(1-menthoxymethyl)-2-(3′-methoxy-4′-hydroxyphenyl)-1,3-dioxolane, 4-(1-menthoxymethyl)-2-(3′-hydroxy-4′-methoxyphenyl)-1,3-dioxolane, 4-(1-menthoxymethyl)-2-(3′-ethoxy-4′-hydroxyphenyl)-1,3-dioxolane, capsaicin, dihydrocapsaicin, nordihydrocapsaicin, homodihydrocapsaicin, homocapsaicin, biscapsanthin, trishomocapsanthin, nornorcapsanthin, norcapsanthin, capsaicinol, vanillyl caprylamide (octylic acid vanillylamide), vanillyl pelargonamide (nonylic acid vanillylamide), vanillyl caproamide (decylic acid vanillylamide), vanillyl undecamide (undecylic acid vanillylamide), N-trans-feruloyltyramine, N-5-(4-hydroxy-3-methoxyphenyl)-2E,4E-pentadienoylpiperidine, N-trans-feruloylpiperidine, N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoylpiperidine, N-5-(4-hydroxyphenyl)-2E,4E-pentadienoylpiperidine, piperine, isopiperine, chavicine, isochavicine, piperamine, piperettine, piperolein B, retrofractamide A, pipercide, guineenside, piperiline, piperamide C5:1 (2E), piperamide C7:1 (6E), piperamide C7:2 (2E,6E), piperamide C9:1 (8E), piperamide C9:2 (2E,8E), piperamide C9:3 (2E,4E,8E), fagaramide, sanshool-I, sanshool-II, hydroxysanshool, sanshoamide, gingerol, shogaol, zingerone, methylgingerol, paradol, spilanthol, chavicine, polygodial (tadeonal), isopolygodial, dihydropolygodial, and tadeon; and
one or more natural products selected from the group consisting of capsicum oil, capsicum oleoresin, ginger oleoresin, jambu oleoresin ( Spilanthes oleracea extract), sansho ( Zanthoxylum piperitum ) extract, sanshoamide, black pepper extract, white pepper extract, and polygonum extract.

7. A flavor composition or a fragrance composition, comprising the sensory stimulant composition according to claim 4 .

8. A product, which is selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, and comprises the flavor composition or the fragrance composition according to claim 7 .

9. A product, which is selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, and comprises the flavor composition or the fragrance composition according to claim 7 in an amount of 0.00001 to 50 mass % based on the total weight of the product.

10. A flavor composition or a fragrance composition, comprising the sensory stimulant composition according to claim 4 in an amount of 0.00001 to 90 mass % based on the total weight of the flavor composition or the fragrance composition.

11. A product, which is selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, and comprises the sensory stimulant composition according to claim 4 .

12. A product, which is selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, and comprises the sensory stimulant composition according to claim 4 in an amount

Assignees

• Takasago Perfumery Co Ltd

Inventors

• Itoh Hisanori
• Hori Yoji
• Otsuka Masashi
• Matsumoto Takaji
• Sato Tomoharu

Classifications

• A23L2/00

  Non-alcoholic beverages; Dry compositions or concentrates therefor (soup concentrates A23L23/10); Preparation or treatment thereof (preparation of non-alcoholic beverages by removal of alcohol C12H3/00) · CPC title

• C09K3/00

  Materials not provided for elsewhere · CPC title

• C07D213/40

  Acylated substituent nitrogen atom · CPC title

• A61Q19/10

  Washing or bathing preparations · CPC title

• C07C233/58 Primary

  having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals · CPC title