Synthesis of Menthol Glycinates and Their Potential as Cooling Agents

Douglas A Klumpp; Robert M Sobel; Smaro G Kokkinidou; Brian Osei-Badu; Zachary Liveris; Rachel A Klumpp; Michael R Stentzel

doi:10.1021/acsomega.9b03624

Synthesis of Menthol Glycinates and Their Potential as Cooling Agents

ACS Omega. 2020 Feb 13;5(8):4043-4049. doi: 10.1021/acsomega.9b03624. eCollection 2020 Mar 3.

Authors

Douglas A Klumpp¹, Robert M Sobel², Smaro G Kokkinidou², Brian Osei-Badu¹, Zachary Liveris¹, Rachel A Klumpp³, Michael R Stentzel¹

Affiliations

¹ Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60178, United States.
² FONA International, Inc., 1900 Averill Rd, Geneva, Illinois 60134, United States.
³ Aurora Christian Schools, 2255 Sullivan Road, Aurora, Illinois 60506, United States.

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.