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Thermal alteration of a cyclic fatty acid produced by a flaxseed extract
Author(s) -
Vick Brady A.,
Zimmerman Don C.,
Weisleder David
Publication year - 1979
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02533899
Subject(s) - chemistry , fatty acid , ring (chemistry) , linum , clinical chemistry , cyclopentenone , carbon chain , stereochemistry , organic chemistry , biochemistry , biology , botany
Methyl 8‐[2‐( cis ‐pent‐2′‐enyl)‐3‐oxo‐ cis ‐cyclopent‐4‐enyl] octanoate (I) is the methyl ester of a cyclic fatty acid synthesized enzymically from an incubation of linolenic acid with an extract of flaxseed ( Linum usitatissimum L.). A proposed trivial name for I is methyl 12‐oxo‐ cis ‐10, 15‐phytodienoate (12‐oxo‐PDA). The evidence presented indicated that compound I has the cis configuration of the carbon chains with respect to the cyclopentenone ring. Treatment with acid, base, or heat isomerized I to a second product (II) that has the trans configuration of the carbon chains. Prolonged heat treatment of II yielded a third cyclic product, methyl 12‐oxo‐9(13), cis ‐15‐phytodienoate (III).