Structural Studies of Polar Dimers in Autoxidized Methyl Linoleate during the Initial Stages of Autoxidation

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Previous structural studies of less-polar dimers in autoxidized methyl linoleate (ML) have been extended to polar dimers. After isolation by successive silicic acid and gel permea tion chromatography, the dimeric fraction of linoleate was separated into two major fractions, A1 and A2, according to their polarities. The polar dimers (A1) were further fractionated by HPLCeither directly or after reduction with triphenyl phosphine on a micro silica column. Isolated sub fractions were characterized by UV, IR, GC-MSand FD-MS after suitable derivatizations. FD-MS of all these dimers showed a molecular ion peak which corresponds to 2×ML+ 6×O and the reduction of each sub fraction with stannous chloride gave equimolar amounts of 9 and 13-hydroxy octadecadienoate, and 9, 10, 13 and/or 9, 12, 1 3-trihydroxy octadecenoate. These results combined with others show that the A1 dimers are composed of isomeric mixtures containing a peroxide bridge linking a methyl octadecadienoate and a 9, 12 and/or 10, 13-dihydroperoxy octadecenoate across C-9 and/or 13 on each of them.
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