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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

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Lipids

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.

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Authors and Affiliations

  1. Department of Chemistry, Karolinska Institutet, S 104 01, Stockholm, Sweden

    Mats Hamberg & Birgitta Gotthammar

Authors
  1. Mats Hamberg
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  2. Birgitta Gotthammar
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Hamberg, M., Gotthammar, B. 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. Lipids 8, 737–744 (1973). https://doi.org/10.1007/BF02531842

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  • DOI: https://doi.org/10.1007/BF02531842

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