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
1973; Wiley; Volume: 8; Issue: 12 Linguagem: Inglês
10.1007/bf02531842
ISSN1558-9307
AutoresMats Hámberg, Birgitta Gotthammar,
Tópico(s)Free Radicals and Antioxidants
ResumoAbstract One of the main compounds formed from 13L‐hydroperoxy‐9 cis ,11 trans ‐octadecadienoic acid anaerobically at 100 C in aqueous ethanol was found to be threo ‐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 involving cis ‐addition to the Δ 11 double bond of the proximally linked hydroperoxide oxygen and hydroxyl ion or hydroxyl radical from the solvent. A small part (ca. 10%) was formed by cis ‐addition of the two hydroperoxide oxygens to the Δ 11 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.
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