Article

Journal of Chemical Ecology

, Volume 11, Issue 5, pp 643-648

First online:

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

  • B. R. LaurenceAffiliated withLondon School of Hygiene and Tropical Medicine
  • , K. MoriAffiliated withDepartment of Agricultural Chemistry, The University of Tokyo
  • , T. OtsukaAffiliated withDepartment of Agricultural Chemistry, The University of Tokyo
  • , J. A. PickettAffiliated withRothamsted Experimental Station
  • , L. J. WadhamsAffiliated withRothamsted Experimental Station

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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.

Key words

Mosquito Culex pipiens fatigans Diptera Culicidae oviposition attractant pheromone chiral chromatography acetoxyhexadecanolide