Abstract
AbstractMethyl 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 thecis 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 thetrans configuration of the carbon chains. Prolonged heat treatment of II yielded a third cyclic product, methyl 12‐oxo‐9(13),cis‐15‐phytodienoate (III).
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