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New Developments in Physiological Cooling Agents

By: Mark Erman

Posted: September 24, 2007, from the October 2007 issue of P&F magazine.

The chemistry and uses of physiological cooling agents—or coolants—have been reviewed in relatively recent articles that cover literature published before 2005. Also, the Web site of Leffingwell & Associates (www.leffingwell.com) is frequently updated and continues to be a valuable source of information. The present article, warranted by rapid development in the chemistry and uses of cooling agents, will focus mostly on newer publications, patents and patent applications, with references to older sources when necessary. Current patent trends will be reviewed separately at the end of this article. 

According to classification suggested in the review “Progress in Physiological Cooling Agents,” commercially available cooling agents with FEMA GRAS status can be divided into two major families: menthoxy and Wilkinson Sword (WS) coolants. Menthoxy coolants include menthyl esters, menthyl ethers, menthone ketals and menthol analogs. WS coolants include p-menthane-3-carboxamides and acyclic carboxamides.

Other topics discussed:

Menthoxy Cooling Agents

• l-Menthyl lactate
• l-Monomenthyl succinate
• l-monomenthyl glutarate
• l-menthyl pyrrolidin-2-one-5-carboxylate
• l-menthyl ester of 4-(N,N-dimethylamino)-4-oxobutanoic acid
• menthyl 3-hydroxybutyrate
• 3-l-menthoxypropane-1,2-diol
• 2-l-menthoxyethanol
• l-menthone glycerol ketal
• p-menthane-3,8-diol
• l-isopulegol

WS Cooling Agents

• N-ethyl-p-menthane-3-carboxamide
• N-(ethoxycarbonylmethyl)-p-menthane-3-carboxamide
• N-(4-cyanomethylphenyl)-p-menthane carboxamide
• N-(4-aminocarbonylphenyl)-p-menthane
• derivative of D-alanine
• N-(3-p-menthanoyl) sulfadiazine
• 2-isopropyl-N,2,3-trimethylbutanamide
• N-(2-ethoxyethyl)-2,3-dimethyl-2-isopropylbutanamide
• N-(1-isopropyl-1-methylisobutyl)anisamide

This is only an excerpt of the full article that appeared in P&F Magazine, but you can purchase the full-text version.