Reptilian chemistry: characterization of dianeackerone, a secretory product from a crocodile

The major volatile component in the paracloacal glandular secretion of the adult African dwarf crocodile (Osteolaemus tetraspis) was isolated and characterized as a 19-carbon aromatic ketone, dianeackerone (3,7-diethyl-9-phenyl-2-nonanone). This ketone is absent from the secretion of immatures. Careful examination of dianeackerone samples isolated from individual adults revealed that this ketone occurs as both the (3S, 7S) and (3S, 7R) stereoisomers, with different individuals presenting strikingly different ratios of the isomeric forms. Our initial suspicion that the stereoisomeric dianeackerones might be indicators of gender proved untenable, leaving the role of these glandular constituents a challenge for future study.