Synthesis of Menthol Glycinates and Their Potential as Cooling Agents

ACS Omega
Douglas A KlumppMichael R Stentzel

Abstract

A convenient method of synthesis has been developed for a new class of potential cooling agents, menthol glycinates. These compounds are prepared in two synthetic steps, starting from bromoacetyl bromide and (-)-menthol. The resulting brominated menthol ester readily undergoes substitution reactions with NH3 and 1° or 2° amines to provide menthol glycinates. For most of the prepared compounds, the two-step synthetic procedure requires no aqueous phase extractions.

References

Aug 1, 1994·The Journal of Pharmacy and Pharmacology·R Eccles
Feb 20, 2007·Current Topics in Medicinal Chemistry·Xuemei Peng, John L Neumeyer
Nov 6, 2013·Journal of Medicinal Chemistry·Amin Haghighat JahromiSteven C Zimmerman
Jul 26, 2017·ACS Medicinal Chemistry Letters·Tomohiro ShiraiAtsushi Ohuchi
Dec 9, 2017·Science·Ying YinSeok-Yong Lee

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Methods Mentioned

BETA
nuclear magnetic resonance
NMR

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