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==Biosynthesis== ==Biosynthesis==
(''Z'')-9-Tricosene is ] in house flies from ].<ref>{{cite journal | pmid = 7937826 | url = http://www.pnas.org/content/91/21/10000.full.pdf | year = 1994 | last1 = Reed | first1 = JR | last2 = Vanderwel | first2 = D | last3 = Choi | first3 = S | last4 = Pomonis | first4 = JG | last5 = Reitz | first5 = RC | last6 = Blomquist | first6 = GJ | title = Unusual mechanism of hydrocarbon formation in the housefly: Cytochrome P450 converts aldehyde to the sex pheromone component (Z)-9-tricosene and CO2 | volume = 91 | issue = 21 | pages = 10000–4 | pmc = 44945 | journal = Proceedings of the National Academy of Sciences of the United States of America | doi=10.1073/pnas.91.21.10000}}</ref> The acid is converted into the ] ] and then reduced to the ] (''Z'')-15-tetracosenal. Through a ] reaction, the aldehyde is converted to (''Z'')-9-tricosene. The process is mediated by a ] enzyme and requires oxygen (O<sub>2</sub>) and ] (NADPH). (''Z'')-9-Tricosene is ] in house flies from ].<ref>{{cite journal | pmid = 7937826 | url = http://www.pnas.org/content/91/21/10000.full.pdf | year = 1994 | last1 = Reed | first1 = JR | last2 = Vanderwel | first2 = D | last3 = Choi | first3 = S | last4 = Pomonis | first4 = JG | last5 = Reitz | first5 = RC | last6 = Blomquist | first6 = GJ | title = Unusual mechanism of hydrocarbon formation in the housefly: Cytochrome P450 converts aldehyde to the sex pheromone component (Z)-9-tricosene and CO2 | volume = 91 | issue = 21 | pages = 10000–4 | pmc = 44945 | journal = Proceedings of the National Academy of Sciences of the United States of America | doi=10.1073/pnas.91.21.10000}}</ref> The acid is converted into the ] ] and then reduced to the ] (''Z'')-15-tetracosenal. Through a ] reaction, the aldehyde is converted to (''Z'')-9-tricosene. The process is mediated by a ] enzyme and requires oxygen (O{{sub|2}}) and ] (NADPH).


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Revision as of 21:44, 5 April 2019

(Z)-9-Tricosene
Names
Preferred IUPAC name (9Z)-Tricos-9-ene
Other names (Z)-Tricos-9-ene
Muscalure
Identifiers
CAS Number
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, 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.

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. ^ "(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. ^ "(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. doi:10.1073/pnas.91.21.10000. PMC 44945. PMID 7937826.
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