cis -9 tricoses

Structural formula
General
Surname	Cis-9 tricoses
other names	Muscalur; Muscamon;
Molecular formula	C 23 H 46
Brief description	colorless liquid
External identifiers / databases
EC number	248-505-7
ECHA InfoCard	100,044,081
PubChem	5365075
Wikidata	Q135445
properties
Molar mass	322.61 g mol −1
Physical state	liquid
density	0.806 g cm −3
boiling point	300 ° C
Refractive index	1.453 (20 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 317
	P: 280-333 + 313
Toxicological data	> 23 g kg −1 ( LD 50 , rat , oral ) ; > 2 g kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

cis -9-tricosene is a chemical compound from the group of aliphatic unsaturated hydrocarbons .

Occurrence

Copulating houseflies

cis -9-Tricosen occurs naturally as a sex pheromone of the female housefly ( Musca domestica ). The compound has also been demonstrated in various other insects. In a mixture with the isomeric cis -7-tricosene, it forms a component of the female sex pheromone of the raven beetle Aleochara curtula .

Extraction and presentation

cis -9-tricosene can be obtained by reacting 1-decene with 1-tetradecene . It can also be obtained by reacting cis -1-bromo-9-octadecene with a Gilman reagent such as (C ₅ H ₁₁ ) ₂ CuLi. With a high degree of enantiomeric purity, it can be obtained through an instant ylide reaction. The biosynthesis in the housefly takes place from nervonic acid .

Biosynthesis of ( Z ) -9-tricosen from nervonic acid

properties

cis -9-Tricosen is a colorless, very difficult to ignite liquid.

use

cis -9-Tricosen can be used in bait to control the housefly.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on cis-9-tricoses in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b ^c data sheet (Z) -9-Tricosene, 97% from Sigma-Aldrich , accessed on April 18, 2015 ( PDF ).
↑ Entry on cis-tricos-9-ene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ ^a ^b entry on Muscalur. In: Römpp Online . Georg Thieme Verlag, accessed on April 18, 2015.
^ Royal Society Of Chemistry, C. Kemball: Catalysis . Royal Society of Chemistry, 1977, ISBN 978-0-85186-534-8 , pp. 280 ( limited preview in Google Book search).
^ Robert J. Ouellette, J. David Rawn: Organic Chemistry: Structure, Mechanism, and Synthesis . Elsevier, 2014, ISBN 978-0-12-801082-2 , pp. 571 ( limited preview in Google Book search).
↑ Alexander M. Moiseenkov, Bruno Schaub, Christian Margot, Manfred Schlosser: A new stereoselective synthesis of (Z) -9-tricosene, the sex attractant of the common housefly. In: Tetrahedron Letters. 26, 1985, p. 305, doi : 10.1016 / S0040-4039 (01) 80803-0 .
↑ JR Reed, D. Vanderwel, S. Choi, JG Pomonis, RC Reitz, GJ Blomquist: Unusual mechanism of hydrocarbon formation in the housefly: cytochrome P450 converts aldehyde to the sex pheromone component (Z) -9-tricosene and CO ₂ . In: Proceedings of the National Academy of Sciences. 91, 1994, p. 10000, doi : 10.1073 / pnas.91.21.10000 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on cis-9-tricoses in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[Sigma-2] ta sheet (Z) -9-Tricosene, 97% from Sigma-Aldrich , accessed on April 18, 2015 ( PDF ).

[CLP_100.044.081-3] Entry on cis-tricos-9-ene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[RömppOnline-4] try on Muscalur. In: Römpp Online . Georg Thieme Verlag, accessed on April 18, 2015.

[Royal_Society_Of_Chemistry,_C._Kemball-5] Royal Society Of Chemistry, C. Kemball: Catalysis . Royal Society of Chemistry, 1977, ISBN 978-0-85186-534-8 , pp. 280 ( limited preview in Google Book search).

[Robert_J._Ouellette,_J._David_Rawn-6] Robert J. Ouellette, J. David Rawn: Organic Chemistry: Structure, Mechanism, and Synthesis . Elsevier, 2014, ISBN 978-0-12-801082-2 , pp. 571 ( limited preview in Google Book search).

[DOI10.1016/S0040-4039(01)80803-0-7] Alexander M. Moiseenkov, Bruno Schaub, Christian Margot, Manfred Schlosser: A new stereoselective synthesis of (Z) -9-tricosene, the sex attractant of the common housefly. In: Tetrahedron Letters. 26, 1985, p. 305, doi : 10.1016 / S0040-4039 (01) 80803-0 .

[DOI10.1073/pnas.91.21.10000-8] JR Reed, D. Vanderwel, S. Choi, JG Pomonis, RC Reitz, GJ Blomquist: Unusual mechanism of hydrocarbon formation in the housefly: cytochrome P450 converts aldehyde to the sex pheromone component (Z) -9-tricosene and CO ₂ . In: Proceedings of the National Academy of Sciences. 91, 1994, p. 10000, doi : 10.1073 / pnas.91.21.10000 .