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

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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.

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References

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Authors and Affiliations

  1. London School of Hygiene and Tropical Medicine, WCIE 7HT, London, UK

    B. R. Laurence

  2. Department of Agricultural Chemistry, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, 113, Tokyo, Japan

    K. Mori & T. Otsuka

  3. Rothamsted Experimental Station, AL5 2JQ, Harpenden, Herts., UK

    J. A. Pickett & L. J. Wadhams

Authors
  1. B. R. Laurence
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  2. K. Mori
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  3. T. Otsuka
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  4. J. A. Pickett
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  5. L. J. Wadhams
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Laurence, B.R., Mori, K., Otsuka, T. et al. Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide. J Chem Ecol 11, 643–648 (1985). https://doi.org/10.1007/BF00988573

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  • DOI: https://doi.org/10.1007/BF00988573

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