(Z)-9-Tricosene (original) (raw)

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(Z)-9-Tricosene
Names
Preferred IUPAC name (9_Z_)-Tricos-9-ene
Other names(Z)-Tricos-9-eneMuscalure
Identifiers
CAS Number 27519-02-4 checkY
3D model (JSmol) Interactive image
ChemSpider 4517167
ECHA InfoCard 100.044.081 Edit this at Wikidata
PubChem CID 5365075
UNII 6BSP6HFW73 checkY
CompTox Dashboard (EPA) DTXSID0032653 Edit this at Wikidata
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-NInChI=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[1]
Melting point −0.6 °C (30.9 °F; 272.5 K)[2]
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). 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

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(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]

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]

(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).

Biosynthesis of (Z)-9-tricosene (bottom) from nervonic acid (top)

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

  1. ^ a b "(Z)-9-Tricosene". Sigma-Aldrich.
  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.
  4. ^ a b "(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.