Singlet oxygen oxidation of methyl linoleate: Isolation and characterization of the NaBH4‐reduced products

作者：Michaël Thomas, William A. Pryor · 发表于：Lipids · 年份：1980 · DOI：10.1007/bf02534228 · 被引用次数：81 · 研究领域：Free Radicals and Antioxidants、Eicosanoids and Hypertension Pharmacology、Metal-Catalyzed Oxygenation Mechanisms

Abstract The mixture of diene hydroperoxides from methylene blue‐sensitized oxidation of methyl linoleate was reduced with NaBH4 and the resulting alcohols were separated by high pressure liquid chromatography (HPLC). Four diene alcohols were isolated in approximately equal yields from adsorption and reversed phase HPLC; the isomers were identified as methyl esters of 9‐hydroxy‐10,12‐, 10‐hydroxy‐8,12‐, 12‐hydroxy‐9,13‐ and 13‐hydroxy‐9,11‐octadecadienoate. Formation of equal yields of both conjugated and nonconjugated diene alcohols from methyl linoleate is characteristic of singlet oxygen oxidations. The detection of the easily separated nonconjugated isomer methyl 10‐hydroxy‐trans‐8,cis‐12‐octadecadienoate from methyl linoleate is proposed as a test to probe the involvement of singlet oxygen in biological oxidations.