(S)-2-pentyl (R)-3-hydroxyhexanoate, a banana volatile and its olfactory recognition by the common fruit fly, Drosophila melanogaster.
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.
Mowat
Jeffrey
J
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada.
Gries
Regine
R
Khaskin
Grigori
G
Gries
Gerhard
G
Britton
Robert
R
D000818:Animals; D002208:Caproates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004331:Drosophila melanogaster / Q000187:drug effects / Q000502:physiology*; D015394:Molecular Structure; D028521:Musa / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009833:Olfactory Pathways / Q000502:physiology*; D013237:Stereoisomerism; D055549:Volatile Organic Compounds / Q000494:pharmacology*
C540701:(S)-2-pentyl (R)-3-hydroxyhexanoate; D002208:Caproates; D055549:Volatile Organic Compounds