(S)-2-pentyl (R)-3-hydroxyhexanoate, a banana volatile and its olfactory recognition by the common fruit fly, Drosophila melanogaster.

ABSTRACT

The volatile organic compounds emitted from ripening bananas that elicit an antennal response from the common fruit fly, Drosophila melanogaster, were analyzed by a combination of gas chromatographic-electroantennographic detection, mass spectrometry, and (1)H NMR spectroscopy. These analyses revealed that the headspace of ripening bananas contains a number of EAD-active components including the new ester (S)-2-pentyl (R)-3-hydroxyhexanoate, the structural assignment of which was confirmed by chemical synthesis.