Identification of Methyl Octanoate Derivatives from Autoxidized Methyl Linoleate by Mass Spectrometry, Nuclear Magnetic Resonance and Infra-red Spectroscopy

Abstract

FROM our investigations on the volatiles from the mild autoxidation of methyl linoleate, we have already reported the isolation and identification of methyl octanoate¹. Frankel et al.² postulated a mechanism for the decomposition of unsaturated hydroperoxy esters that predicts the formation not only of methyl octanoate but also of 8-formyl methyl octanoate, and 8-hydroxy methyl octanoate from 9-hydroperoxy methyl linoleate. Ellis³ also postulated the formation of semi-aldehydes from oxidation of unsaturated fatty acids. This communication reports further results on an extract of the autoxidized oil which show the presence of 8-formyl methyl octanoate and the formate of 8-hydroxy methyl octanoate (8-formoxy methyl octanoate).