Z-9-Tetradecenyl acetate

The ability of male moths to perceive mixtures of geometric isomers with extraordinary acuity was further documented in an investigation of the responses of males of the redbanded leaf-roller and two populations of the European cornborer to isomers of 11-tetradecenyl acetate (21). Redbanded leafroller males were essentially unresponsive to pure preparations of their reported sex pheromone, (Z)-11-tetradecenyl acetate, but were strongly attracted to lures containing up to 8% of the (E)-isomer. Similarly, European cornborer males from Iowa responded maximally when 4% of the (E)-isomer was added to the (Z)-isomer, whereas the New York population was attracted to an isomeric mixture containing about 4% of the (Z )-isomer. Enhanced attraction by a small proportion of the opposite geometric isomer was also demonstrated with males of the oriental fruit moth,... 

The redbanded leafroller moth uses a mixture of (E) and (Z) -11-tetradecenyl acetates as pheromone components. The pheromone gland of this insect also contains an acetyl Co A fatty alcohol acyl transferase (22.). This enzyme will acetylate 12, 14 and 16 carbon alcohols, and prefers the saturated alcohol to the Z monounsaturated derivative, and the Z to the E, in the approximate ratios of 5 3 1 for saturated, Z and E, respectively. 

In related work Chapman et al. (219) defined the conformation of Z-11-tetradecenyl acetate (49), the sex attractant of the European corn borer and the red banded leaf roller, in the pheromone chemore-ceptor system, of these two species. 

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