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(Z)-9-Tricosene

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(Z)-9-Tricosene
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 Edit this at Wikidata
UNII
  • 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
  • C(=C\CCCCCCCCCCCCC)\CCCCCCCC
Properties
C23H46
Molar mass 322.621 g·mol−1
Density 0.806 g/mL[1]
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).

(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.[2]

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.[3]

Biosynthesis

(Z)-9-Tricosene is biosynthesized in house flies from nervonic acid.[4] 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)

Safety

Products containing (Z)-9-tricosene are considered safe for humans, wildlife, and the environment.[3]

References

  1. ^ a b "(Z)-9-Tricosene". Sigma-Aldrich.
  2. ^ 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  3. ^ a b "(Z)-9-Tricosene (103201) Fact Sheet". United States Environmental Protection Agency.
  4. ^ 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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