(''Z'')-9-Tricosene, known as muscalure, is an insect

pheromone A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavio ...

found in

diptera Flies are insects of the order Diptera, the name being derived from the Greek δι- ''di-'' "two", and πτερόν ''pteron'' "wing". Insects of this order use only a single pair of wings to fly, the hindwings having evolved into advance ...

n flies such as the

housefly The housefly (''Musca domestica'') is a fly of the suborder Cyclorrhapha. It possibly originated in the Middle East, and Cosmopolitan distribution, spread around the world as a commensal of humans. Adults are gray to black, with four dark, lo ...

. Females produce it to attract males to mate. It is used as a

pesticide Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...

, 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 Waggle dance is a term used in beekeeping and ethology for a particular figure-eight dance of the honey bee. By performing this dance, successful foragers can share information about the direction and distance to patches of flowers yielding ne ...

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 Biosynthesis, i.e., chemical synthesis occurring in biological contexts, is a term most often referring to multi-step, enzyme- catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthesis) serve ...

in house flies from nervonic acid. The acid is converted into the

acyl-CoA Acyl-CoA is a group of coenzyme A, CoA-based coenzymes that metabolize carboxylic acids. Fatty acyl-CoA's are susceptible to beta oxidation, forming, ultimately, acetyl-CoA. The acetyl-CoA enters the citric acid cycle, eventually forming several e ...

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

and then reduced to the

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

(''Z'')-15-tetracosenal. Through a

decarboxylation Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is ...

reaction, the aldehyde is converted to (''Z'')-9-tricosene. The process is mediated by a

cytochrome P450 Cytochromes P450 (P450s or CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that mostly, but not exclusively, function as monooxygenases. However, they are not omnipresent; for examp ...

enzyme and requires oxygen (O) and

nicotinamide adenine dinucleotide phosphate Nicotinamide adenine dinucleotide phosphate, abbreviated NADP or, in older notation, TPN (triphosphopyridine nucleotide), is a Cofactor (biochemistry), cofactor used in anabolic reactions, such as the Calvin cycle and lipid and nucleic acid synt ...

(NADPH). :

Safety

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

References

{{DEFAULTSORT:Tricosene, (Z)-9- Insect pheromones Pesticides Alkenes Hydrocarbons