Pheromones, 65. Identification of the volatile components of the mandibular gland secretion of the ant Manica rubida: Structure elucidation, synthesis, and absolute configuration of Manicone

By means of gas chromatography and mass spectrometry, Manicone, (4E)‐4,6‐dimethyl‐4‐octen‐3‐one (1), was identified as the main component of the mandibular gland secretion of the ant Manica rubida. In addition the presence of homomanicone (2), bishomomanicone (3), normanicone (7), and a few aliphatic aldehydes and ketones was also evident in the gland. Racemic 1, 2, and 7 and optically active dihydromanicone (4), were synthesized. The (S) configuration of 1 was determined by complexation gas chromatography, on a chiral phase, of 4 as well as of the hydrogenation products of racemic and natural 1.