The components of the essential oil of
Mentha gentilis L. “Haruyama mint (2
n=72)” known to distribute in Tokai area of Japan were investigated by means of column and gas chromatography, IR, MS and NMR spectrometry. As reported previously, this oil was shown to contain
d-1, 2-epoxymenthylacetate (piperitylacetateoxide).
In the present report, we intend to inform the identification of
d-1, 2-epoxymenthol which was isolated as a new terpenic compound from the same oil. Isolated compound was identical with that of authentic sample which was obtained as the hydrolysis product of natural 1, 2-epoxymenthylacetate. This compound was also converted to the acetate by the esterification. Furthermore, this compound could be confirmed in comparison with synthetic 1, 2-epoxymenthol which was prepared as the reduction product of
l-piperitoneoxide. From NMR spectra and optical rotation data of these products we conclude that the absolute configuration of natural epoxy alcohol is (+) 1, 2-epoxy-
cis-
p-menthol.
From the fact that
Mentha gentilis L. produces 1, 2-epoxymenthol we presume that this substance is an intermediate between piperitoneoxide and 1, 2-epoxymenthylacetate on the biosynthetic process
in vivo, although this compound may lack in the essential oil of
Mentha rotundifolia (L.).
View full abstract