Process for making monomenthyl esters

A kind of technology of menthyl ester and menthol, applied in the field of monomenthyl ester of dicarboxylic acid, can solve problems such as high toxicity, unrealistic

Active Publication Date: 2009-03-18
利安德巴塞尔调味香料和芳香有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, this method is impractical as it requires a large excess of anhydride, pyridine solvent, and the highly toxic DMAP

Method used

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  • Process for making monomenthyl esters
  • Process for making monomenthyl esters
  • Process for making monomenthyl esters

Examples

Experimental program
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Embodiment Construction

[0013] The method of the present invention reacts menthol with a saturated cyclic anhydride. Menthol suitable for use may have any desired stereochemistry. With three chiral centers, menthol has eight possible stereoisomers. A menthol sample may have several different stereoisomers present. Examples include 1-menthol, d-menthol, d1-menthol (i.e. a racemic mixture of 1-menthol and d-menthol), neomenthol, isomenthol, and isomers of neoisomenthol, and their mixture. 1-menthol, d-menthol, dl-menthol and other isomers are commercially available. 1-Menthol (1) is particularly preferred since it provides a monomenthyl ester with excellent physiological cooling properties.

[0014]

[0015] Suitable anhydrides are saturated cyclic anhydrides. Preferably, the anhydride ring contains 2-4 methylene groups or substituted methylene groups. Examples include succinic anhydride, glutaric anhydride, adipic anhydride, methylsuccinic anhydride, 2-phenylglutaric anhydride, 3-methylglutar...

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Abstract

A process for making monomenthyl esters of dicarboxylic acids is disclosed. Menthol reacts with a saturated, cyclic anhydride in the presence of a base catalyst under conditions effective to produce a mixture of mono- and bis-menthyl esters in which the molar ratio of mono- to bis-menthyl esters is enhanced compared with the ratio of esters produced in a similar uncatalyzed process.

Description

technical field [0001] The present invention relates to monomenthyl esters of dicarboxylic acids which are useful as physiological coolants. Background technique [0002] Monomenthyl esters of dicarboxylic acids such as monomenthyl succinate (MMS), monomenthyl glutarate (MMG) and monomenthyl adipate (MMA) are physiological cooling agents used in fragrances, oral care and cosmetics. When prepared using 1-menthol as starting material, these half-esters have the structures shown below: [0003] [0004] The use of these compounds as flavorants or physiological coolants is described, for example, in U.S. Patents 5,725,865 (MMS) and 6,884,906 (MMA), and in Smith et al., Food Technology ( Food Tech. ) 55 (2001) 53 (MMG). Additionally, MMS and MMG have achieved FEMA GRAS (Generally Regarded as Safe) status. [0005] While monomenthyl esters are of undisputed value, little is known about how to prepare them efficiently. In one approach (see Rule et al., Journal of Chemistry ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/42C07C69/40C07C69/44
CPCC07C67/08C07C2101/14C07C2601/14C07C69/42C07C69/44C07C69/40
Inventor M·B·厄曼J·W·斯诺M·Y·勒彼德弗
Owner 利安德巴塞尔调味香料和芳香有限责任公司
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