Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide

Laurence, B., Mori, K., Otsuka, T., Pickett, J. A. ORCID: https://orcid.org/0000-0002-8386-3770 and Wadhams, L. J. 1985. Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide. Journal of Chemical Ecology 11 (5) , pp. 643-648. 10.1007/BF00988573

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Abstract

6-Acetoxy-5-hexadecanolide (Ia) in the oviposition attractant pheromone released from egg apical droplets of the mosquitoCulex pipiens fatigans Wied. is shown to be the (−)-(5R,6S)- enantiomer. Identification was by chromatography of the 6-trifluoroacetoxy derivatives of the natural pheromone and of the synthetic (−)-(5R,6S)- (Ib) and (+)-(5S,6R)- (IIb) enantiomers on a capillary column having a chiral stationary phase comprising a derivative of (1S,3S)-chrysanthemic acid. The synthetic (−)-(5R,6S)- enantiomer (Ia) attracted oviposition of four fold more mosquito egg rafts than the control (P < 0.01) whereas for the (5S,6R)- enantiomer (IIa) there was no statistically significant oviposition attraction.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Publisher:	Springer
ISSN:	0098-0331
Date of Acceptance:	6 September 1984
Last Modified:	06 Feb 2026 11:45
URI:	https://orca.cardiff.ac.uk/id/eprint/184466

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