Non-metal-requiring Catalyst Contained in Recovered Methyl Linolenate from an Autoxidizing Sample

Abstract

Non-metal-requiring catalysts in recovered methyl linolenate from an autoxidizing sample were unstable on contact with silicic acid and the activity varied widely with the way of recovery, countercurrent extraction and column chromatography under different conditions. After reduction with stannous chloride, a substance was found which was characteristically present in the products derived from the recovered methyl linolenate high in the catalytic activity. It was tentatively identified by MS, IR, OsO₄ oxidation-IO₄^- oxidation, and LiAlH₄ reduction-IO₄^- oxidation as methyl 9, 13-dihydroxy-10-epoxy-15-octadecenoate.