(Z)-9-Tricosene
| (Z)-9-Tricosene | ||
|---|---|---|
/-/(Z)-9-tricosene.svg.png){kind=small} | ||
| (9Z)-9-Tricosene | ||
| Other names Muscalure[1] | ||
| Identifiers | ||
| PubChem | 5365075 | |
| ChemSpider | 4517167 | |
| Jmol-3D images | Image 1 | |
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| 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
(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
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
(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).
/-/(Z)-9-tricosene_biosynthesis.svg.png)
Biosynthesis of (Z)-9-tricosene (bottom) from nervonic acid (top)
Safety
Products containing (Z)-9-tricosene are considered safe for humans, wildlife, and the environment.[4]
References
- ↑ "Muscalure". alanwood.net.
- ↑ 2.0 2.1 "(Z)-9-Tricosene". Sigma-Aldrich.
- ↑ 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.
- ↑ 4.0 4.1 "(Z)-9-Tricosene (103201) Fact Sheet". United States Environmental Protection Agency.
- ↑ 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.