The shoulder gland secretions of captive males of the Indian flying fox (Pteropus giganteus), the little golden-mantled flying fox (P. pumilus), the island flying fox (P. hypomelanus), and the large flying fox (P. vampyrus) were examined by gas chromatography-mass spectrometry. Sixty-five compounds, including hydrocarbons, carboxylic acids, alcohols, aldehydes, ketones, esters, and amides, were identified among the four species. Many of these compounds, such as squalene, cholesterol, and C5-C16 straight- and branched-chain carboxylic acids, are typical of tetrapod epidermal products. Aldehydes, which were detected in all four Pteropus species, and some straight- and branched-chain ketones, which were detected in P. hypomelanus and P. pumilus, are known from other mammalian skin glands. Acetophenone, 4-acetoxyacetophenone, and 4-hydroxyacetophenone were observed in P. pumilus; the last compound comprised 37.1% of the total ion current. 2,3-Butanediol, a prominent component (5.2-19.3%) in the secretions of P. giganteus, P. hypomelanus, and P. pumilus, and C10 and C12 isopropyl esters and C10-C14 1-methylbutyl esters, observed in P. hypomelanus and P. vampyrus, have not previously been reported from vertebrates. alpha-Methyl-4-methoxybenzyl alcohol and dihydro-5-phenyl-2(3H)-furanone, from P. giganteus and P. pumilus, are new natural products. 1-Chloro-3-methyl-2-butene, another new natural product, and five C5 compounds exhibiting a similar isoprenoid structure were observed in P. giganteus. Striking contrasts were observed in the chemical profiles of the species we examined, with even general chemical classes differentially represented among them.