IDENTIFICATION AND BIOSYNTHESIS OF (E,E)-10,12-TETRADECADIENYL ACETATE IN SPODOPTERA-LITTORALIS FEMALE SEX-PHEROMONE GLAND

A minor component of the sex pheromone gland of the Egyptian cotton le afworm, Spodoptera littoralis, has been identified as (E,E)-10,12-tetr adecadienyl acetate. Structural elucidation has been carried out by is obutane-chemical ionization mass spectrometry of the fatty acyl biosyn thetic precursor-derived methyl ester. To assign the stereochemistry o f the double bonds, the four isomers of both 10,12-tetradecadienyl ace tates and methyl 10,12-tetradecadienoates have been synthesized and th eir gas chromatography retention times and mass spectra have been comp ared to those of the corresponding natural compounds. Mass-labeling ex periments showed that the (E,E)-10,12-tetradecadienoyl moiety is biosy nthetically derived from (Z)-11-tetradecenoic acid in the insect phero mone gland. (C) 1997 Elsevier Science Ltd.