Synthesis of Ethyl 5Z,9Z,12Z‐octadecatrienoate (ethyl pinolenate) and Methyl 12Z,15Z‐octadecadienoate
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- 11 March 2008
- journal article
- Published by Wiley in Journal of the American Oil Chemists' Society
- Vol. 85 (6) , 561-565
Abstract
Pinolenic acid (5Z,9Z,12Z‐octadecatrienoic acid, 1a), one of the most abundant trienoic fatty acids in nature, is very difficult to obtain in quantity in a pure state from the highly complex mixture of unsaturated tall oil fatty acids. For this reason its chemistry has been little studied when compared to linolenic or linoleic acids. A simple synthesis of esters of 1a and of 12Z,15Z‐octadecadienoic acid 3 using the one pot double Wittig procedure is described here. The products of double Wittig reactions were purified by argentation chromatography, and their structural purity was established by 1H‐, 13C‐NMR and 2D‐NMR spectroscopies.Keywords
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