Synthesis of Menthol Glycinates and Their Potential as Cooling Agents

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...

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Published inACS omega Vol. 5; no. 8; pp. 4043 - 4049
Main Authors Klumpp, Douglas A, Sobel, Robert M, Kokkinidou, Smaro G, Osei-Badu, Brian, Liveris, Zachary, Klumpp, Rachel A, Stentzel, Michael R
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 03.03.2020
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Summary: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.
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ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.9b03624