Model systems of methyl linoleate were studied to obtain proof of principle that multiple alternate pathways of lipid oxidation exist and compete with hydrogen abstraction to determine oxidation kinetics and product distributions. Conjugated dienes, hydroperoxides, carbonyls, and epoxides were measured daily for 20 days in open and closed systems as a function of temperature, oxygen, and solvent. Conjugated dienes (CD) dominated under all conditions. At 40 �C, epoxides and hydroperoxides were formed in equal concentrations at ~half the CD level; at 60 �C, all products accumulated at lower levels, and epoxides approached CD concentrations while hydroperoxides decreased. Aldehydes were found at only trace levels in both systems.  Results suggest that internal rearrangement to epoxides is more active than H abstraction to form hydroperoxides or scissions to form carbonyls in methyl linoleate.  Solvent proticity and oxygen had relatively minor effects on product levels but did not change the order CD> epoxides>hydroperoxides>carbonyls.

Evidence for multiple oxidation pathways from non-volatile products of methyl linoleate

246th National Meeting (2013)

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