Menthol

History and occurrence

Shimyama has asserted that menthol has been known in Japan for more than 2000 years, but in the west it was not isolated until 1771, by Gambius. (-)-Menthol (also called l-menthol or (1R,2S,5R)-menthol) occurs naturally in peppermint oil (along with a little menthone, the ester menthyl acetate and other compounds), obtained from various species of Mentha piperita L. Japanese menthol also contains a small percentage of the 1-epimer, (+)-neomenthol.

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Menthone: Menthone is a naturally occurring organic compound with a molecular formula C10H18O. l-Menthone (or (2S, 5R)-trans-2-isopropyl-5-methylcyclohexanone), shown at right, is the most abundant in nature of the four possible stereoisomers. Menthone is a monoterpene and a ketone. It is structurally rela...

Menthyl acetate: Menthyl acetate is a natural monoterpene which contributes to the smell and flavor of peppermint. It is the acetate ester of menthol. Menthyl acetate constitutes 3-5% of the volatile oil of mentha piperita....

Epimer: In chemistry, an epimer is a stereoisomer that has a different configuration at only one of several stereogenic centers....