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Synthesis of Ethyl 5 Z ,9 Z ,12 Z ‐octadecatrienoate (ethyl pinolenate) and Methyl 12 Z ,15 Z ‐octadecadienoate
Author(s) -
Kaltia Seppo,
Matikainen Jorma,
AlaPeijari Maija,
Hase Tapio
Publication year - 2008
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-008-1226-x
Subject(s) - wittig reaction , chemistry , linoleic acid , organic chemistry , linolenic acid , double bond , fatty acid , unsaturated fatty acid , stereochemistry
Pinolenic acid (5 Z ,9 Z ,12 Z ‐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 12 Z ,15 Z ‐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 1 H‐, 13 C‐NMR and 2D‐NMR spectroscopies.