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Photooxidation of (Z,E)-9,11-tetradecadienyl acetate, the main component of the sex pheromone of the female egyptian cotton leafworm (spodoptera littoralis)

✍ Scribed by Arnon Shani; Jacob T. Klug


Publisher
Elsevier Science
Year
1980
Tongue
French
Weight
157 KB
Volume
21
Category
Article
ISSN
0040-4039

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✦ Synopsis


Monoolefins and conjugated dienes are known to react with singlet oxygen to form allylic hydroperoxides in the first case and endoperoxides in the second one.' Most of the already known insect sex pheromones are long chain aliphatic alcohols, aldehydes, ketones or esters with one or two double bonds along the chain.* It is thus expected that oxidation will take place when these compounds are left in sunlight. The photooxidation of (Z,E)-9,12-tetradecadienyl acetate,3 and fatty acids,4 are examples of this type of chemical react?-vTty.


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(3E,8Z,11Z)-3,8,11-Tetradecatrienyl acet
✍ Athula B. Attygalle; Gulab N. Jham; AleΕ‘ SvatoΕ‘; Rosa T.S. Frighetto; Fernando A πŸ“‚ Article πŸ“… 1996 πŸ› Elsevier Science 🌐 English βš– 969 KB

The major sex attractant emitted by Scrobipalpuloides absoluta females is shown to be (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate by a novel strategy involving the random reduction of double bonds, followed by methylthiolation of the reduced products. Each female sex gland contains ca. 1-5 ng of