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(Z)-9-Tricosene

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(Z)-9-Tricosene
Names
IUPAC name (9Z)-9-Tricosene
Other names Muscalure
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.081 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
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
Density 0.806 g/mL
Boiling point 300 °C (572 °F; 573 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

(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 a communication pheromone 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).

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.

References

  1. "Muscalure". alanwood.net.
  2. ^ "(Z)-9-Tricosene". Sigma-Aldrich.
  3. ^ "(Z)-9-Tricosene (103201) Fact Sheet". United States Environmental Protection Agency.
  4. . PMID 7937826 http://www.pnas.org/content/91/21/10000.full.pdf. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
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