(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.
-9-tricosene.svg){kind=small}
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| Names | |
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| Preferred IUPAC name
(9Z)-Tricos-9-ene | |
| Other names
(Z)-Tricos-9-ene
Muscalure | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.044.081 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C23H46 | |
| Molar mass | 322.621 g·mol−1 |
| Density | 0.806 g/mL[1] |
| Melting point | −0.6 °C (30.9 °F; 272.5 K)[2] |
| Boiling point | 300 °C (572 °F; 573 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
editAs 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)
-9-tricosene_biosynthesis.svg)
Safety
editProducts containing (Z)-9-tricosene are considered safe for humans, wildlife, and the environment.[4]
References
edit- ^ a b "(Z)-9-Tricosene". Sigma-Aldrich.
- ^ Gibbs, Allen; Pomonis, J.George (1995). "Physical properties of insect cuticular hydrocarbons: The effects of chain length, methyl-branching and unsaturation". Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology. 112 (2). Elsevier BV: 243–249. doi:10.1016/0305-0491(95)00081-x. ISSN 1096-4959.
- ^ 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.
- ^ a b "(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. Bibcode:1994PNAS...9110000R. doi:10.1073/pnas.91.21.10000. PMC 44945. PMID 7937826.