(Z)-9-Tricosene

{{#if:0.806 g/mL4623|! style="background: #F8EABA; text-align: center;" colspan="2" | Properties

(Z)-9-Tricosene
File:(Z)-9-tricosene.svg
IUPAC name (9Z)-9-Tricosene
Other names Muscalure
Identifiers
PubChem	5365075
ChemSpider	4517167
Jmol-3D images	Image 1
SMILES C(=C\CCCCCCCCCCCCC)\CCCCCCCC <p><p style="word-wrap: break-word;">
InChI InChI=1S/C23H46/c1-3-5-7-9-11-13-15-17-19-21-23-22-20-18-16-14-12-10-8-6-4-2/h17,19H,3-16,18,20-23H2,1-2H3/b19-17- Key: IGOWHGRNPLFNDJ-ZPHPHTNESA-N InChI=1/C23H46/c1-3-5-7-9-11-13-15-17-19-21-23-22-20-18-16-14-12-10-8-6-4-2/h17,19H,3-16,18,20-23H2,1-2H3/b19-17- Key: IGOWHGRNPLFNDJ-ZPHPHTNEBA
Molecular formula	C23H46
Molar mass	322.61 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.

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.

Biosynthesis

(Z)-9-Tricosene is biosynthesized in house flies from nervonic acid. 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).

File:(Z)-9-tricosene biosynthesis.svg

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.