Cyclohexanol derivative, cool feeling and cool feeling composition containing the same, process for producing the derivative and intermediate therefor
AssigneeHisamitsu Pharmaceutical Co., Inc.
InventorsMitsuru Kuribayashi, Mitsuru Tanoue, Akira Nakagawa, Munehiko Hirano, Hideshi Oda
Life of this patent
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Abstract
A cyclohexanol derivative represented by the following general formula (1) and preferably the following general formula (1a): ##STR1## wherein R represents a linear or branched alkyl group having 1 to 5 carbon atoms. The above cyclohexanol derivative imparts satisfactory refrigeration to not only the mouth mucosa but also the skin. Moreover, it is practically odorless. A cool feeling and various cool feeling compositions which are practically odorless can be obtained from the cyclohexanol derivative.
Claims7
A cyclohexanol derivative represented by the following general formula:
- ##STR13## wherein R represents a linear or branched alkyl group having 1 to 5 carbon atoms.
A cyclohexanol derivative represented by the following general formula:
- ##STR14## wherein R represents a linear or branched alkyl group having 1 to 5 carbon atoms.
A process for producing a cyclohexanol derivative represented by the following general formula:
- ##STR15## wherein R represents a linear or branched alkyl group having 1 to 5 carbon atoms, which comprises reacting (-)-isopulegol represented by the following formula:
- ##STR16## with a benzyl halide in the presence of metallic sodium or sodium hydride to thereby form a compound represented by the following formula:
- ##STR17## hydroborating the compound (3a) to thereby obtain a compound represented by the following formula:
- ##STR18## alkylating the compound (4a) with an alkylating agent in the presence of a base to thereby form a compound represented by the following general formula:
- ##STR19## wherein R represents a linear or branched alkyl group having 1 to 5 carbon atoms, and
- catalytically hydrogenating the compound (5a) in the presence of a debenzylating agent.
A cool feeling composition comprising 0.001-10% by weight of a cyclohexanol derivative of formula ##STR20## wherein R is a linear or branched alkyl group having 1 to 5 carbon atoms.
Dependencies are inferred from the claim text.