Origin of bicyclic fatty acids in tall oil |
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Authors: | Anneli Hase O Harva Tuula Pakkanen |
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Affiliation: | (1) Laboratory of Industrial Chemistry, Helsinki University of Technology, Otaniemi, Finland |
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Abstract: | 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). |
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