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Revision as of 11:02, 9 August 2014 editRjwilmsi (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers932,094 editsm →Biosynthesis: Journal cites, Added 1 doi to a journal cite using AWB (10331)← Previous edit Revision as of 20:08, 23 February 2015 edit undoDePiep (talk | contribs)Extended confirmed users294,285 editsNo edit summaryNext edit →
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| OtherNames = Muscalure<ref>{{cite web | url = http://www.alanwood.net/pesticides/muscalure.html | title = Muscalure | publisher = alanwood.net}}</ref> | OtherNames = Muscalure<ref>{{cite web | url = http://www.alanwood.net/pesticides/muscalure.html | title = Muscalure | publisher = alanwood.net}}</ref>
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| CASNo = | CASNo =
| PubChem = 5365075 | PubChem = 5365075
| ChemSpiderID = 4517167 | ChemSpiderID = 4517167
| SMILES = C(=C\CCCCCCCCCCCCC)\CCCCCCCC | SMILES = C(=C\CCCCCCCCCCCCC)\CCCCCCCC
| 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- | 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-
| InChIKey = IGOWHGRNPLFNDJ-ZPHPHTNEBA | InChIKey = IGOWHGRNPLFNDJ-ZPHPHTNEBA
| StdInChI = 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- | StdInChI = 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-
| StdInChIKey = IGOWHGRNPLFNDJ-ZPHPHTNESA-N | StdInChIKey = IGOWHGRNPLFNDJ-ZPHPHTNESA-N
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C=23|H=46 | C=23|H=46
| Appearance = | Appearance =
| Density = 0.806 g/mL<ref name=Aldrich>{{cite web | url = http://www.sigmaaldrich.com/catalog/product/ALDRICH/859885?lang=en | title = (Z)-9-Tricosene | publisher = ]}}</ref> | Density = 0.806 g/mL<ref name=Aldrich>{{cite web | url = http://www.sigmaaldrich.com/catalog/product/ALDRICH/859885?lang=en | title = (Z)-9-Tricosene | publisher = ]}}</ref>
| MeltingPt = | MeltingPt =
| BoilingPtC = 300 | BoilingPtC = 300
| Boiling_ref = <ref name=Aldrich/> | BoilingPt_ref = <ref name=Aldrich/>
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| AutoignitionPt = | AutoignitionPt =
}} }}
}} }}

Revision as of 20:08, 23 February 2015

(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 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. "Muscalure". alanwood.net.
  2. ^ "(Z)-9-Tricosene". Sigma-Aldrich.
  3. Template:Cite doi/10.1371.2Fjournal.pbio.0050228
  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. doi:10.1073/pnas.91.21.10000. PMC 44945. PMID 7937826.
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