(Z)-3-hexenyl (R)-3-hydroxybutanoate: a male specific compound in three North American decorator wasps Eucerceris rubripes, E. conata and E. tricolor.

The males of the decorator wasps Eucerceris have been observed to display abdomen-dragging behavior on plants surrounding their nest. It is thought that this applies a territorial-marking sex pheromone that serves to alert females to the males' territory for courtship and mating. The extracts of three species E. rubripes, E. conata, and E. tricolor have been analyzed by GC-MS. The gas chromatograms revealed the presence, in large quantities, of one common volatile compound in the male head extracts. By analogy with the closely related bee wolves Philanthus, we believe the pheromone is produced in the mandibular glands. Utilizing mass spectrometry, microreactions, FT-IR, and 1H and 13C NMR spectroscopy the structure of the pheromone was proposed to be (Z)-3-hexenyl 3-hydroxybutanoate, which was confirmed by synthesis. The absolute configuration of the chiral center was determined to be R for the three species by preparing the Mosher esters of the insect samples and comparing their GC retention times with a synthetic sample of known absolute configuration. In addition 2- and 3-hexenoic acid and some aromatic compounds were also found in varying quantities in both males and females along with hydrocarbons and fatty acids, although no species-specific profiles emerged.