(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} | |
| Names | |
|---|---|
| Preferred IUPAC name (9Z)-Tricos-9-ene | |
| Other names (Z)-Tricos-9-ene Muscalure | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.044.081 |
PubChem CID | |
| 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). | |
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).
Biosynthesis of (Z)-9-tricosene (bottom) from nervonic acid (top)
-9-tricosene_biosynthesis.svg)
Safety
Products containing (Z)-9-tricosene are considered safe for humans, wildlife, and the environment.[4]