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. 1985 May;11(5):643-8.
doi: 10.1007/BF00988573.

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

B R Laurence  1 , K Mori, T Otsuka, J A Pickett, L J Wadhams
Affiliations

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

B R Laurence et al. J Chem Ecol. 1985 May.

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.

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