A new reaction of unsaturated fatty acid hydroperoxides: Formation of 11‐hydroxy‐12,13‐epoxy‐9‐octadecenoic acid from 13‐hydroperoxy‐9,11‐octadecadienoic acid

作者：Mats Hámberg, Birgitta Gotthammar · 发表于：Lipids · 年份：1973 · DOI：10.1007/bf02531842 · 被引用次数：115 · 研究领域：Eicosanoids and Hypertension Pharmacology、Organic Chemistry Cycloaddition Reactions、Free Radicals and Antioxidants

Abstract One of the main compounds formed from 13L‐hydroperoxy‐9cis,11trans‐octadecadienoic acid anaerobically at 100 C in aqueous ethanol was found to bethreo‐11‐hydroxy‐12,13‐epoxy‐9‐octadecenoic acid. The major part (ca. 90%) of this compound was formed from the fatty acid hydroperoxide in a reaction involvingcis‐addition to the Δ11 double bond of the proximally linked hydroperoxide oxygen and hydroxyl ion or hydroxyl radical from the solvent. A small part (ca. 10%) was formed bycis‐addition of the two hydroperoxide oxygens to the Δ11 double bond. 11‐Hydroxy‐12,13‐epoxy‐9‐octadecenoic acid and its isomer, tentatively identified as 11‐hydroxy‐9,10‐epoxy‐12‐octadecenoic acid, also were isolated from a sample of autoxidized linoleic acid.