Sex pheromone of the american cockroach,Periplaneta americana

The sex pheromone of the American cockroach,Periplaneta americana, consists of two compounds, which we have named periplanone-A and periplanone-B. The two compounds can be isolated from fecal material in a ratio of 1∶10, and periplanone-B can also be isolated from intestinal tracts. A total amount of 200 μg of periplanone-B has been isolated from both fecal material and alimentary tracts. By means of gas chromatography-mass spectrometry, hydrogenation, infrared analysis, and NMR analysis, we were able to identify periplanone-B as (1Z,5E)-1,10(14)-diepoxy-4(15),5-germacradien-9-one. The overall structure was confirmed by comparison with a synthetic, biologically active epimer of periplanone-B.