(Z)-9-Tricosene Explained

(Z)-9-Tricosene, known as muscalure, is an insect pheromone found in dipteran flies such as the housefly. Females produce it to attract males to mate. It is used as a pesticide, as in Maxforce Quickbayt by Bayer, luring males to traps to prevent them from reproducing.

Biological functions

(Z)-9-Tricosene is a sex pheromone produced by female house flies (Musca domestica) to attract males. In bees, it is one of the communication pheromones released during the waggle dance.[1]

Uses

As a pesticide, (Z)-9-tricosene is used in fly paper and other traps to lure male flies, trap them, and prevent them from reproducing.[2]

Biosynthesis

(Z)-9-Tricosene is biosynthesized in house flies from nervonic acid.[3] The acid is converted into the acyl-CoA derivative and then reduced to the aldehyde (Z)-15-tetracosenal. Through a decarboxylation reaction, the aldehyde is converted to (Z)-9-tricosene. The process is mediated by a cytochrome P450 enzyme and requires oxygen (O) and nicotinamide adenine dinucleotide phosphate (NADPH).

Safety

Products containing (Z)-9-tricosene are considered safe for humans, wildlife, and the environment.[2]

Notes and References

  1. 10.1371/journal.pbio.0050228. 17713987. 2007. Thom . C.. Gilley . D.. Hooper . J.. Esch . H.. The scent of the waggle dance. 5. 9. e228. 1994260. PLOS Biology . free.
  2. Web site: (Z)-9-Tricosene (103201) Fact Sheet . United States Environmental Protection Agency.
  3. 7937826 . Unusual mechanism of hydrocarbon formation in the housefly: Cytochrome P450 converts aldehyde to the sex pheromone component (Z)-9-tricosene and CO2 . 1994 . Reed . JR . Vanderwel . D . Choi . S . Pomonis . JG . Reitz . RC . Blomquist . GJ . 91 . 21 . 10000–4 . 44945 . Proceedings of the National Academy of Sciences of the United States of America . 10.1073/pnas.91.21.10000. 1994PNAS...9110000R . free .