cis-9-Oxo-2-decenoic Acid: Synthesis and Evaluation as a Honey Bee Pheronione and Masking Agent

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Abstract
A new improved synthesis of the cis isomer of the honey bee, Apis mellifera L. (Hymenoptera: Apidae), queen substance, trans-9-oxo-2-decenoic acid, is described. The cis acid is somewhat active as an inhibitor of queen cell construction in honey bee colonies because small amounts are converted to the active trans isomer. Drone honey bees are not attracted to the cis acid. After prolonged exposure to sunlight, the cis isomer is photoisomerized to the active sex attractant, trans queen substance. The cis-9-oxo-2-decenoic acid does not mask ihc sex attractant activity of its geometric isomer during short-term exposures of lures containing 1:1 mixtures of both isomers.

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