ChemInform Abstract: Pheromones. Part 65. Identification of the Volatile Components of the Mandibular Gland Secretion of the Ant Manica rubida: Structure Elucidation, Synthesis, and Absolute Configuration of Manicone.

Abstract

ChemInform Abstract Manicone (Ia) is identified as the main component of the title species. In addition the presence of homomanicone (Ib), bishomomanicone (Ic), normanicone (Id), and a few aliphatic aldehydes and ketones is also found in the gland. Racemic (Ia), (Ib) and (Id) as well as optically active dihydromanicone (XI) are synthesized as outlined in the scheme. The (S)-configuration of (Ia) is determined by complexation gas chromatography, on a chiral phase, of (XI) as well as of the hydrogenation products of racemic and natural (Ia).

Comparative chemical analysis of army ant mandibular gland volatiles (Formicidae: Dorylinae)

“…This ion, the lack of a prominent m/z = 71, together with the base ion at m/z = 57 arising from the α-cleavage relative to the carbonyl C, indicated that the compounds are 4-methyl-3-ketones ( 5, 7, 9 ; see Table 1 for compound IDs). The identities of 4,6-dimethyl-3-ketones were evaluated based on mass spectrometric data provided by Fales et al (1980) , Bestmann et al (1988) and Bergmann et al (2001) . Consequently, we assigned the detected alcohols based on their M + −1 ion to an affiliated ketone that represented the oxidized form of a respective alcohol (see also Do Nascimento et al, 1997 ).…”