Cool-sensation imparter composition containing 2,2,6-trimethylcyclohexanecarboxylic acid derivative

Patent metadata

Field	Value
Publication number	US-11344488-B2
Application number	US-201816756015-A
Country	US
Kind code	B2
Filing date	Oct 16, 2018
Priority date	Oct 16, 2017
Publication date	May 31, 2022
Grant date	May 31, 2022

Abstract

A cooling agent composition contains a 2,2,6-trimethylcyclohexanecarboxylic acid derivative represented by the following general formula (1). The symbol * represents an asymmetric carbon atom. X represents NH, N(ZAr2), O or S, Z represents a single bond or an alkylene group having 1 to 3 carbon atoms which may have a substituent, Ar2 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent. Y each independently represents a methylene group which may have a substituent, and n represents an integer of 0 to 3. Ar1 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent.

First claim

The invention claimed is:

1. A cooling agent composition comprising a 2,2,6-trimethylcyclohexanecarboxylic acid derivative represented by the following general formula (1):

wherein the symbol * represents an asymmetric carbon atom,
X represents NH, N(ZAr 2 ), O or S, Z represents a single bond or an alkylene group having 1 to 3 carbon atoms which may have a substituent, Ar 2 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent,
Y each independently represents a methylene group which may have a substituent,
n represents an integer of 0 to 3, and
Ar 1 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent.

2. The cooling agent composition according to claim 1 , wherein X represents NH or N(ZAr 2 ) in the 2,2,6-trimethylcyclohexanecarboxylic acid derivative.

3. The cooling agent composition according to claim 1 , wherein X represents NH or N(ZAr 2 ) in the 2,2,6-trimethylcyclohexanecarboxylic acid derivative, and the 2,2,6-trimethylcyclohexanecarboxylic acid derivative is a (1R, 6S)-form.

4. The cooling agent composition according to claim 1 , wherein X represents NH or N(ZAr 2 ), n represents 0 or 2, and Z represents a single bond or an ethylene group which may have a substituent in the 2,2,6-trimethylcyclohexanecarboxylic acid derivative.

5. The cooling agent composition according to claim 1 , wherein X represents NH or N(ZAr 2 ), n represents 0 or 2, and Z represents a single bond or an ethylene group which may have a substituent in the 2,2,6-trimethylcyclohexanecarboxylic acid derivative, and the 2,2,6-trimethylcyclohexanecarboxylic acid derivative is a (1R, 6S)-form.

6. The cooling agent composition according to claim 1 , wherein X represents NH or N(ZAr 2 ), n represents 2, and Z represents an ethylene group which may have a substituent, in the 2,2,6-trimethylcyclohexanecarboxylic acid derivative.

7. The cooling agent composition according to claim 1 , wherein X represents NH or N(ZAr 2 ), n represents 2, and Z represents an ethylene group which may have a substituent in the 2,2,6-trimethylcyclohexanecarboxylic acid derivative, and the 2,2,6-trimethylcyclohexanecarboxylic acid derivative is a (1R, 6S)-form.

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

9. The sensory stimulant composition according to claim 8 , further comprising at least one kind of warming substance.

10. The sensory stimulant composition according to claim 9 , wherein the warming substance is at least one warming substance selected from the group consisting of:
one or more kinds of compounds selected from 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 acetate, isovanillyl butyl ether acetate, ethyl vanillyl butyl ether acetate, 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, bis-capsaicin, trishomocapsaicin, nornorcapsaicin, norcapsaicin, capsaicinol, vanillyl caprylamide (octylic acid vanillylamide), vanillyl pelargonamide (nonylic acid vanillylamide), vanillyl caproamide (decylic acid vanillylamide), vanillyl undecanamide (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 kinds of natural products selected from capsicum pepper oil, capsicum pepper oleoresin, ginger oleoresin, jambu oleoresin (extract from Spilanthes acmella L. var. oleracea Clarke), Japanese pepper extract, sanshoamide, black pepper extract, white pepper extract, and Polygonum extract.

11. The cooling agent composition according to claim 1 , further comprising at least one kind of cooling substance other than the 2,2,6-trimethylcyclohexanecarboxylic acid derivative.

12. The cooling agent composition according to claim 11 , wherein the cooling substance is at least one cooling 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, i sopulegyl salicylate, 3 -(1-menthoxy)propane- 1,2-diol, 2-methyl-3-(1-menthoxy)propane-1,2-diol, 2-(1-menthoxy)ethane-1-ol, 3-(1-menthoxy)propane-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, 3-(p-menthane-3-carboxamide) ethyl acetate, N-(4-methoxyphenyl)-p-menthane carboxamide, N-ethyl-2,2-diisopropylbutanamide, N-cyclopropyl-p-menthane carboxamide, N-(4-cyanomethylphenyl)-p -menthanecarboxamide, N-(2-pyridin-2-yl)-3-p-menthane carboxamide, 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 kinds of sugar alcohols selected from xylitol, erythritol, dextrose, and sorbitol; and
one or more kinds of natural products selected from Japanese mint oil, peppermint oil, spearmint oil, and eucalyptus oil.

13. A flavor or fragrance comp

Assignees

• Takasago Perfumery Co Ltd

Inventors

• Matsumoto Takaji
• Itoh Hisanori
• Sato Tomoharu
• Otsuka Masashi
• Harada Makoto

Classifications

• C11D3/3409

  Alkyl -, alkenyl -, cycloalkyl - or terpene sulfates or sulfonates · CPC title

• C07C233/59

  having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups · CPC title

• A61K8/498

  having 6-membered rings or their condensed derivatives, e.g. coumarin · CPC title

• A61K8/4986

  with sulfur as the only hetero atom · CPC title

• A61K8/46

  containing sulfur (A61K8/44 takes precedence) · CPC title