(Z)-9-Tricosene

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(Z)-9-Tricosene
(Z)-9-tricosene.svg
Identifiers
PubChem 5365075
ChemSpider 4517167
Jmol-3D images Image 1
Properties
Molecular formula C23H46
Molar mass 322.61 g mol−1
Density 0.806 g/mL[2]
Boiling point 300 °C (572 °F; 573 K)[2]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

(Z)-9-Tricosene (muscalure) is an insect pheromone used as a pesticide.

Biological functions[edit]

(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.[3]

Uses[edit]

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.[4]

Biosynthesis[edit]

(Z)-9-Tricosene is biosynthesized in house flies from nervonic acid.[5] 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 (O2) and nicotinamide adenine dinucleotide phosphate (NADPH).

Biosynthesis of (Z)-9-tricosene (bottom) from nervonic acid (top)

Safety[edit]

Products containing (Z)-9-tricosene are considered safe for humans, wildlife, and the environment.[4]

References[edit]

  1. ^ "Muscalure". alanwood.net. 
  2. ^ a b "(Z)-9-Tricosene". Sigma-Aldrich. 
  3. ^ Thom, C.; Gilley, D.; Hooper, J.; Esch, H. (2007). "The scent of the waggle dance". PLoS Biology 5 (9): e228. doi:10.1371/journal.pbio.0050228. PMC 1994260. PMID 17713987. 
  4. ^ a b "(Z)-9-Tricosene (103201) Fact Sheet". United States Environmental Protection Agency. 
  5. ^ Reed, JR; Vanderwel, D; Choi, S; Pomonis, JG; Reitz, RC; Blomquist, GJ (1994). "Unusual mechanism of hydrocarbon formation in the housefly: Cytochrome P450 converts aldehyde to the sex pheromone component (Z)-9-tricosene and CO2". Proceedings of the National Academy of Sciences of the United States of America 91 (21): 10000–4. PMC 44945. PMID 7937826.