Journal of Chemical Ecology

, Volume 11, Issue 5, pp 643–648

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

  • B. R. Laurence
  • K. Mori
  • T. Otsuka
  • J. A. Pickett
  • L. J. Wadhams
Article

DOI: 10.1007/BF00988573

Cite this article as:
Laurence, B.R., Mori, K., Otsuka, T. et al. J Chem Ecol (1985) 11: 643. doi:10.1007/BF00988573

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.

Key words

MosquitoCulex pipiens fatigansDipteraCulicidaeovipositionattractantpheromonechiral chromatographyacetoxyhexadecanolide

Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • B. R. Laurence
    • 1
  • K. Mori
    • 2
  • T. Otsuka
    • 2
  • J. A. Pickett
    • 3
  • L. J. Wadhams
    • 3
  1. 1.London School of Hygiene and Tropical MedicineLondonUK
  2. 2.Department of Agricultural ChemistryThe University of TokyoTokyoJapan
  3. 3.Rothamsted Experimental StationHarpendenUK