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| ImageFile = (Z)-9-tricosene.svg | ImageFile = (Z)-9-tricosene.svg
| ImageSize = 250px | ImageSize = 250px
| IUPACName = (9''Z'')-9-Tricosene | PIN = (9''Z'')-Tricos-9-ene
| OtherNames = (''Z'')-Tricos-9-ene<br />Muscalure
| 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 = 27519-02-4
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | PubChem = 5365075
| UNII = 6BSP6HFW73
⚫ | ChemSpiderID = 4517167
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | SMILES = C(=C\CCCCCCCCCCCCC)\CCCCCCCC
⚫ | PubChem = 5365075
⚫ | 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-
⚫ | ChemSpiderID = 4517167
⚫ | InChIKey = IGOWHGRNPLFNDJ-ZPHPHTNEBA
⚫ | SMILES = C(=C\CCCCCCCCCCCCC)\CCCCCCCC
⚫ | 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-
⚫ | 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-
⚫ | StdInChIKey = IGOWHGRNPLFNDJ-ZPHPHTNESA-N
⚫ | 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-
⚫ | 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 = | MeltingPtC = -0.6
| MeltingPt_ref = <ref name="GibbsPomonis">{{cite journal | last1=Gibbs | first1=Allen | last2=Pomonis | first2=J.George | title=Physical properties of insect cuticular hydrocarbons: The effects of chain length, methyl-branching and unsaturation | journal=Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology | publisher=Elsevier BV | volume=112 | issue=2 | year=1995 | issn=1096-4959 | doi=10.1016/0305-0491(95)00081-x | pages=243–249}}</ref>
| 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 =
}} }}
}} }}


'''(''Z'')-9-Tricosene''' ('''muscalure''') is an insect ] used as a ]. '''(''Z'')-9-Tricosene''', known as '''muscalure''', is an insect ] found in ]n flies such as the ]. Females produce it to attract males to mate. It is used as a ], as in Maxforce Quickbayt by Bayer, luring males to traps to prevent them from reproducing.


==Biological functions== ==Biological functions==
(''Z'')-9-Tricosene is a ] produced by female ] (''Musca domestica'') to attract males. In bees, it is one of the communication pheromones released during the ].<ref>{{Cite doi/10.1371.2Fjournal.pbio.0050228}}</ref> (''Z'')-9-Tricosene is a ] produced by female ] (''Musca domestica'') to attract males. In bees, it is one of the communication pheromones released during the ].<ref>{{Cite journal| doi = 10.1371/journal.pbio.0050228| pmid = 17713987| year = 2007| last1 = Thom | first1 = C.| last2 = Gilley | first2 = D.| last3 = Hooper | first3 = J.| last4 = Esch | first4 = H.| title = The scent of the waggle dance| volume = 5| issue = 9| pages = e228| pmc = 1994260| journal = PLOS Biology | doi-access = free}}</ref>


==Uses== ==Uses==
Line 41: Line 45:


==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| bibcode = 1994PNAS...9110000R | doi-access = free }}</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).


:] (top)]]{{clear-left}} :] (top)]]{{clear-left}}

Latest revision as of 02:44, 28 November 2023

(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
UNII
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
Melting point −0.6 °C (30.9 °F; 272.5 K)
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. 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. ^ "(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.
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