Synthesis of Ethyl 5Z,9Z,12Z-octadecatrienoate (ethyl pinolenate) and Methyl 12Z,15Z-octadecadienoate

• Published in: Journal of the American Oil Chemists' Society Vol. 85; no. 6; pp. 561 - 565
• Main Authors: Kaltia, Seppo, Matikainen, Jorma, Ala-Peijari, Maija, Hase, Tapio
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Berlin/Heidelberg : Springer-Verlag 01-06-2008; Springer-Verlag; Springer; Springer Nature B.V
• Subjects: 12Z,15Z‐octadecadienoic acid; Agriculture; Aldehydes; Argentation chromatography; Biological and medical sciences; Biomaterials; Biotechnology; Chemistry; Chemistry and Materials Science; Chromatography; Esters; Fat industries; Fatty acids; Food industries; Food Science; Fundamental and applied biological sciences. Psychology; Industrial Chemistry/Chemical Engineering; Oils & fats; Original Paper; Pinolenic acid (5Z,9Z,12Z‐octadecatrienoic acid); Temperature; Vegetable oils; Wittig reaction; octadecatrienoic acid; Wittig reaction; 12; octadecadienoic acid; 15; 9; Argentation chromatography; Pinolenic acid; Oils and fats industry; Wittig reaction . Argentation chromatography; Pinolenic acid (5Z,9Z,12Z-octadecatrienoic acid) .12Z,15Z-octadecadienoic acid; Chromatography
• ISSN: 0003-021X; 1558-9331
• DOI: 10.1007/s11746-008-1226-x

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.