cis-Vaccenyl acetate as an aggregation pheromone inDrosophila melanogaster

Pentane extracts of matureDrosophila melanogaster males substantially increased the attractiveness of food odors to both males and females in a wind-tunnel olfactometer. Extracts of females caused no such increase. An active component of the extract was isolated and identified as (Z)-11-octadecenyl acetate (cis-vaccenyl acetate, cVA), and synthetic cVA was active in bioassay. Hydrolysis of the ester linkage or movement of the double bond to the 9 position destroyed the activity. Mature virgin males released cVA into their feeding vials, and amounts of synthetic CVA equal to that released per male caused significant bioassay responses. Females, which were known to receive cVA from males during copulation, were found to emit relatively large amounts of the ester into their feeding vials within 6 hr after mating. cVA had been demonstrated previously to be a close-range pheromone inD. melanogaster, discouraging males from courting other males or recently mated females; it now appears to have a longer-range function as well.