Facile and Stereoselective Synthesis of (Z)-15-Octadecenoic Acid and (Z)-16-Nonadecenoic Acid: Monounsaturated Omega-3 Fatty Acids

Springer Berlin
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Journal Article
Lipids, 2010, 45 pp. 159 - 165
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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 esteri?ed and oxidised, followed by the Wittig reaction to introduce the omega-3 ole?nic 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 C gave optimal stereoselectivity, affording the omega-3 ole?ns in Z:E ratios C97:3. The syntheses have overall yields of *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 1 H13C-HSQC NMR and GCMS, respectively.
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