Differences in oxidation kinetics between conjugated and non-conjugated methyl linoleate

Lipids. 2007 Dec;42(12):1085-92. doi: 10.1007/s11745-007-3113-x. Epub 2007 Sep 25.

Abstract

The oxidation kinetics of conjugated methyl linoleate was compared with that of non-conjugated methyl linoleate under mild oxidation conditions (30 degrees C in the dark). Samples of methyl 9-cis,11-trans-linoleate, methyl 10-trans,12-cis linoleate and methyl 9-cis,12-cis linoleate were assayed separately and in mixtures. For comparative purposes, methyl alpha-linolenate and methyl oleate were also used. Two complementary analytical approaches were selected to monitor the progress of oxidation, (1) the traditional follow-up of residual substrate by gas liquid chromatography, and (2) an analytical procedure by high-performance size-exclusion chromatography (HPSEC) for direct measurement of the oxidation compounds formed. The HPSEC method enabled us to quantitate oxidized monomers, dimers and polymers concomitantly in a rapid and direct analysis. Results showed that conjugated methyl linoleate samples oxidized later than their non-conjugated counterparts, and showed a very different oxidation pattern. Thus, formation of oxidized monomers was negligible and the first and major compounds formed were polymerization products. Also, under the conditions used, non-conjugated and conjugated methyl linoleate samples in 1:1 mixtures led to decreased oxidation rate of non-conjugated methyl linoleate and increased oxidation rate of conjugated methyl linoleate. This study supports the view that oxidation kinetics of conjugated dienes differ substantially from that of methylene-interrupted dienes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, Gas
  • Chromatography, High Pressure Liquid
  • Kinetics
  • Linoleic Acids / chemistry*
  • Linoleic Acids, Conjugated / chemistry*
  • Oxidation-Reduction

Substances

  • Linoleic Acids
  • Linoleic Acids, Conjugated
  • methyl linoleate