Synthesis of Ethyl 5 Z ,9 Z ,12 Z -octadecatrienoate (ethyl pinolenate) and Methyl 12 Z ,15 Z -octadecadienoate |
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| Authors: | Seppo Kaltia Jorma Matikainen Maija Ala-Peijari and Tapio Hase |
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| Affiliation: | (1) Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki, P.O. Box. 55, 00014 Helsinki, Finland |
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| 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.
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| Keywords: | Pinolenic acid (5Z 9Z 12Z-octadecatrienoic acid) 12Z 15Z-octadecadienoic acid Wittig reaction Argentation chromatography |
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