Epoxidation reactions of unsaturated fatty esters with potassium peroxomonosulfate

Lipids. 1998 Jun;33(6):633-7. doi: 10.1007/s11745-998-0250-6.

Abstract

Epoxidation of the double bond in methyl oleate, octadec-11E-en-9-ynoate, ricinoleate (12-hydroxy-octadec-9Z-enoate), iso-ricinoleate (9-hydroxy-octadec-12Z-enoate), and 12-oxo-octadec-9Z-enoate with potassium peroxomonosulfate (oxone, 2 KHSO5.KHSO4.K2SO4) in the presence of trifluoroacetone or methyl pyruvate gave the corresponding monoepoxy derivatives. Reaction of Oxone with methyl linoleate and octadeca-9Z,11E-dienoate furnished the corresponding diepoxystearate derivative. Methyl 9,12-dioxo-octadec-10Z-enoate was obtained when a C18 furanoid fatty ester (methyl 9,12-epoxy-9,11-octadecadienoate) was treated with Oxone. The yield of these reactions was very high (85-99%), and the epoxy derivatives were readily isolated by solvent extraction. The products were identified by spectroscopic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Epoxy Compounds / chemistry
  • Esterification
  • Fatty Acids, Unsaturated / chemistry*
  • Indicators and Reagents
  • Oxidants / chemistry*
  • Oxidation-Reduction
  • Sulfuric Acids / chemistry*

Substances

  • Epoxy Compounds
  • Fatty Acids, Unsaturated
  • Indicators and Reagents
  • Oxidants
  • Sulfuric Acids
  • potassium peroxymonosulfuric acid