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Origin of bicyclic fatty acids in tall oil
Author(s) -
Hase Anneli,
Harva O.,
Pakkanen Tuula
Publication year - 1974
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/bf02639735
Subject(s) - bicyclic molecule , chemistry , organic chemistry , tall oil , fatty acid , distillation , diene , natural rubber
It was shown that two bicyclic fatty acids present in Finnish tall oil were formed from (5Z, 9Z, 12Z)‐5, 9, 12‐octadecatrienoic acid, pinolenic acid (I). Under the alkaline conditions of sulfate pulping, pinolenic acid forms conjugated isomers which undergo Diels‐Alder cyclization during the heating in the tall oil distillation. The cyclization products, here called cyclopinolenic acids, are bicyclic fatty acids and stereoisomers of 4‐(5‐pentyl‐3a, 4,5,7a‐tetrahydro‐4‐indanyl) butanoic acid (IV and V).