(Z)-9-Tricosene

(Z)-9-Tricosene
Names
	Preferred IUPAC name (9Z)-Tricos-9-ene
	Other names (Z)-Tricos-9-ene; Muscalure
Identifiers
CAS Number	27519-02-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	4517167;
ECHA InfoCard	100.044.081
PubChem CID	5365075;
UNII	6BSP6HFW73 ;
CompTox Dashboard (EPA)	DTXSID0032653 ;
	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;
	SMILES C(=C\CCCCCCCCCCCCC)\CCCCCCCC;
Properties
Chemical formula	C23H46
Molar mass	322.621 g·mol−1
Density	0.806 g/mL
Melting point	−0.6 °C (30.9 °F; 272.5 K)
Boiling point	300 °C (572 °F; 573 K)
	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, 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.

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).

Safety

Products containing (Z)-9-tricosene are considered safe for humans, wildlife, and the environment.^[4]

References

^ ^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.

[Aldrich-1] "(Z)-9-Tricosene". Sigma-Aldrich.

[GibbsPomonis-2] 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.

[3] 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.

[epa-4] "(Z)-9-Tricosene (103201) Fact Sheet". United States Environmental Protection Agency.

[5] 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.

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