Cyclohexanol derivative, cool feeling and cool feeling composition containing the same, process for producing the derivative and intermediate therefor

• US 5,756,857 A
• Filed: 04/25/1995
• Issued: 05/26/1998
• Est. Priority Date: 10/29/1992
• Status: Expired due to Term

• Current Assignee: Hisamitsu Pharmaceutical Company Incorporated
• Original Assignee: Hisamitsu Pharmaceutical Company Incorporated
• Inventors: Kuribayashi, Mitsuru, Tanoue, Mitsuru, Nakagawa, Akira, Oda, Hideshi, Hirano, Munehiko
• Primary Examiner(s): Shaver, Paul F.
• Application Number:
  US08/433,375
• Time in Patent Office: 1,127 Days
• Field of Search: 568/579, 568/670, 424/49, 424/55, 424/65, 424/69, 424/715, 514/715, 514/844, 514/847, 514/848, 514/901
• US Class Current: 568/579
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 43/13 containing hydroxy or O-metal groups C07C43/11 takes precedence
• CPC Class Codes: C07C 43/188 Unsaturated ethers
• CPC Class Codes: C07C 43/196 containing hydroxy or O-metal groups

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.

Claims

1. 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.

2. A cool feeling composition comprising the cyclohexanol derivative defined in claim 1.

5. The composition according to claim 2 comprising said cyclohexanol derivative in the amount of 0.001-10% by weight.

3. 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.

6. The cyclohexanol derivative according to claim 3 wherein R is methyl.

4. 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.

7. 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.