(Z)-9-Tricosene
-9-tricosene.svg.png){kind=small} | |
| Names | |
|---|---|
| IUPAC name
(9Z)-9-Tricosene | |
| Other names
Muscalure[1] | |
| Identifiers | |
| 27519-02-4 | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 4517167 |
| ECHA InfoCard | 100.044.081 |
| PubChem | 5365075 |
| |
| |
| Properties | |
| C23H46 | |
| Molar mass | 322.62 g·mol−1 |
| Density | 0.806 g/mL[2] |
| Boiling point | 300 °C (572 °F; 573 K)[2] |
| Except where otherwise noted, 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).
-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.
- 1 2 "(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. - 1 2 "(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" (PDF). Proceedings of the National Academy of Sciences of the United States of America. 91 (21): 10000–4. doi:10.1073/pnas.91.21.10000. PMC 44945. PMID 7937826.