Formation, isolation and structure determination of methyl linolenate diperoxides

✍ Scribed by David T. Coxon; Keith R. Price; Henry W.-S. Chan

• Book ID: 103037019
• Publisher: Elsevier Science
• Year: 1981
• Tongue: English
• Weight: 596 KB
• Volume: 28
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(81)90022-0

✦ Synopsis

Autoxidation of methyl linolenate gives rise to isomeric mono-hydroperoxides by reaction with one mole of oxygen but further reaction with a second mole of oxygen readily occurs to produce an isomeric mixture of diperoxides. Autoxidation of individual pure methyl hydroperoxylinolenate isomers has been used as a method of obtaining less complex diperoxide mixtures which can be separated into their pure components by preparative high-pressure liquid chromatography (HPLC). The major diperoxide isomers arising from the autoxidation of pure 9R-and 13S-hydroperoxides of methyl linolenate have been isolated and characterised as isomeric epidioxyhydroperoxides of methyl linolenate. These same compounds have been identified as components of the more complex mixture of diperoxides produced during methyl linolenate autoxidation. The structures of the isolated diperoxides have been determined by physico-chemical methods and a mechanism for their formation is proposed.