Synthesis and Bioassay of the Eight Analogues of the CH503 Male Pheromone (3-Acetoxy-11,19-octacosadien-1-ol) of the Drosophila melanogaster Fruit Fly

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  • SHIKICHI Yasumasa
    Photosensitive Materials Research Center, Toyo Gosei Co., Ltd.
  • SHANKAR Shruti
    Temasek Life Sciences Laboratory, 1 Research Link, National University of Singapore Department of Biological Sciences, 14 Science Drive 4, National University of Singapore
  • YEW Joanne Y.
    Temasek Life Sciences Laboratory, 1 Research Link, National University of Singapore Department of Biological Sciences, 14 Science Drive 4, National University of Singapore
  • MORI Kenji
    Photosensitive Materials Research Center, Toyo Gosei Co., Ltd.

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  • Synthesis and Bioassay of the Eight Analogues of the CH503 Male Pheromone (3-Acetoxy-11,19-octacosadien-1-ol) of the <i>Drosophila melanogaster</i> Fruit Fly

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説明

Eight analogues of (3R,11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol), the anti-aphrodisiac pheromone of male Drosophila melanogaster, were synthesized for a bioassay. These were the enantiomers of 3-acetoxy-11,19-octacosadiyn-1-ol (1), 3-acetoxyoctacosan-1-ol (2), (Z)-3-acetoxy-11-octacosen-1-ol (3), and (Z)-3-acetoxy-19-octacosen-1-ol (4). None of them were pheromonally active, indicating that the two double bonds at C-11 and C-19 were necessary for bioactivity.

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