Facile and stereoselective synthesis of (Z)-15-octadecenoic acid and (Z)-16-nonadecenoic acid: monounsaturated omega-3 fatty acids

Lipids. 2010 Feb;45(2):159-65. doi: 10.1007/s11745-009-3378-3.

Abstract

Facile syntheses of the monounsaturated omega-3 fatty acids, (Z)-15-octadecenoic acid and (Z)-16-nonadecenoic acid, are presented. Commercially available hydroxy fatty acids were esterified and oxidised, followed by the Wittig reaction to introduce the omega-3 olefinic bond; hydrolysis yielded the omega-3 fatty acids in high purity. An examination of different reaction conditions for the Wittig step found that THF as solvent and coupling temperatures of -78 degrees C gave optimal stereoselectivity, affording the omega-3 olefins in Z:E ratios >or= 97:3. The syntheses have overall yields of approximately 43%, and utilise straightforward, robust chemistry, that may be readily scaled up and reproduced. Also presented is a method for accurately determining the double bond geometry and isomeric purity of the fatty acid products using 1H-13C-HSQC NMR and GC-MS, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fatty Acids, Monounsaturated / chemical synthesis*
  • Fatty Acids, Omega-3 / chemical synthesis*
  • Nuclear Magnetic Resonance, Biomolecular
  • Oleic Acids / chemical synthesis*
  • Stereoisomerism

Substances

  • 15-octadecenoic acid
  • 16-nonadecenoic acid
  • Fatty Acids, Monounsaturated
  • Fatty Acids, Omega-3
  • Oleic Acids