Isomeric monoethylenic fatty acids in herring oil.

Monoethylenic fatty acids from herring oil were concentrated by chromatography by chromatography on silver nitratesilicic acid columns. Examination of consecutive fractions by open tubular gas chromatography confirmed the preferential elution of longer chain length esters and of esters within one chain length with the double bond closer to the terminal methyl group. Isomeric monoethylenic fatty acids with double bonds in the positions closer to the carboxyl group than the approximate midpoint of the even-numbered fatty acid chains could not be adequately separated by gas chromatography and were determined by ozonolysis. The isomers observed are consistent with primary formation from saturated acids through the action of an enzyme specifically removing hydrogen atoms in positions Delta(9) and Delta(10) relative to the carboxyl group. Chain extension of particular monoethylenic isomers by two carbon atoms in the C(20) and longer chain lengths is apparently influenced by the position of the double bond.