title: 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.
abstract: 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.
authors.affiliation: Photosensitive Materials Research Center, Toyo Gosei Co., Ltd.
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Shikichi
authors.forename: Shruti
authors.initials: S
authors.lastname: Shankar
authors.forename: Joanne Y
authors.initials: JY
authors.lastname: Yew
authors.forename: Kenji
authors.initials: K
authors.lastname: Mori
mesh_terms: D000818:Animals; D001681:Biological Assay; D060326:Chemistry Techniques, Synthetic; D004331:Drosophila melanogaster / Q000187:drug effects*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008297:Male; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D012726:Sexual Behavior, Animal / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: C587917:3-acetoxy-11,19-octacosadien-1-ol; D005231:Fatty Acids, Unsaturated; D005233:Fatty Alcohols; D010675:Pheromones