Jan 1, 1977

Autoxidation of methyl linoleate. Separation and analysis of isomeric mixtures of methyl linoleate hydroperoxides and methyl hydroxylinoleates

Lipids
H W Chan, G Levett

Abstract

The mixture of conjugated diene hyperperoxide isomers obtained from autoxidation of methyl linoleate was separated by high performance liquid chromatography (HPLC). Four major isomers were obtained from adsorption chromatography and identified as the 9 and 13 positional isomers having the trans-trans and cis-trans configurations. The latter geometrical isomers have the trans double bond adjacent to the hydroperoxide group. The hydroxy compounds (methyl hydroxylinoleates) obtained from the hydroperoxides by NaBH4 reduction were similarly separated but with improved resolution. This is the first instance of the complete separation of these compounds and provides a rapid method for their analysis. Unlike adsorption chromatography, reversed-phase chromatography separates the mixtures only according to the geometrical isomerism of the double bonds and not according to the position of the hydroxy or hydroperoxide function.

Mentioned in this Paper

In Vivo NMR Spectroscopy
Hydrogen Peroxide
Structure-Activity Relationship
Chromatography
Rapid Technique
Linoleic Acids
methyl linoleate
Spectrophotometry, Ultraviolet
High Pressure Liquid Chromatography Procedure
Peroxides

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