(Z)-9-Tricosene

Insect pheromone (Z)-9-Tricosene (Z)-9-tricosene.svg 250px (9Z)-Tricos-9-ene (Z)-Tricos-9-eneMuscalure 27519-02-4 correct CAS 6BSP6HFW73 correct FDA 5365075 4517167 C(=C\CCCCCCCCCCCCC)\CCCCCCCC 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- IGOWHGRNPLFNDJ-ZPHPHTNEBA 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- IGOWHGRNPLFNDJ-ZPHPHTNESA-N 23 46 0.806 g/mL http://www.sigmaaldrich.com/catalog/product/ALDRICH/859885?lang=en (Z)-9-Tricosene Sigma-Aldrich -0.6 Gibbs Allen Pomonis J.George 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 Elsevier BV 112 2 1995 1096-4959 10.1016/0305-0491(95)00081-x 243–249 300 (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. 10.1371/journal.pbio.0050228 17713987 2007 Thom C. Gilley D. Hooper J. Esch H. The scent of the waggle dance 5 9 e228 1994260 PLOS Biology free 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. http://www.epa.gov/opp00001/biopesticides/ingredients/factsheets/factsheet_103201.htm https://web.archive.org/web/20160308012815/http://www.epa.gov/pesticides dead March 8, 2016 (Z)-9-Tricosene (103201) Fact Sheet United States Environmental Protection Agency Biosynthesis (Z)-9-Tricosene is biosynthesized in house flies from nervonic acid. 7937826 http://www.pnas.org/content/91/21/10000.full.pdf 1994 Reed JR Vanderwel D Choi S Pomonis JG Reitz RC Blomquist GJ Unusual mechanism of hydrocarbon formation in the housefly: Cytochrome P450 converts aldehyde to the sex pheromone component (Z)-9-tricosene and CO2 91 21 10000–4 44945 Proceedings of the National Academy of Sciences of the United States of America 10.1073/pnas.91.21.10000 1994PNAS...9110000R free 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). thumb|left|400px|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 Category:Insect pheromones Category:Pesticides Category:Alkenes Category:Hydrocarbons