The conversion of linoleic acid (13S)-hydroperoxide into (13R)-hydroxy-12-oxo-octadec-(9Z)-enoic acid and 9-hydroxy-12-oxo-octadec-(10E)-enoic acid by a flax enzyme. Isotopic evidence for allene epoxide intermediates

Abstract

Conversion of [9,10,12,13-²H₄]linoleic acid, via its 13-hydroperoxide, into the γ-ketol (9) by a flax enzyme, with loss of C-13-[²H], can only satisfactorily be explained by the intervention of an allene epoxide intermediate; α-ketol (2) formation involves a similar mechanism.