(''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 advanced ...

n flies such as the

housefly The housefly (''Musca domestica'') is a fly of the suborder Cyclorrhapha. It is believed to have evolved in the Cenozoic Era, possibly in the Middle East, and has spread all over the world as a commensal of humans. It is the most common fl ...

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

pesticide Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampri ...

, as in Maxforce Quickbayt by Bayer, luring males to traps to prevent them from reproducing.

Biological functions

(''Z'')-9-Tricosene is a

sex pheromone Sex pheromones are pheromones released by an organism to attract an individual of the same species, encourage them to mate with them, or perform some other function closely related with sexual reproduction. Sex pheromones specifically focus on ind ...

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 nect ...

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 is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. ...

in house flies from

nervonic acid Nervonic acid (24:1, n−9) is a fatty acid. It is a monounsaturated analog of lignoceric acid (24:0). It is also known as selacholeic acid and ''cis''-15-tetracosenoic acid. Its name derives from the Latin word ''wikt:nervus, nervus'', meaning ...

. The acid is converted into the

acyl-CoA Acyl-CoA is a group of coenzymes that metabolize fatty acids. Acyl-CoA's are susceptible to beta oxidation, forming, ultimately, acetyl-CoA. The acetyl-CoA enters the citric acid cycle, eventually forming several equivalents of ATP. In this way ...

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...

and then reduced to the

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...

(''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 t ...

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

cytochrome P450 Cytochromes P450 (CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are ...

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 synth ...

(NADPH). : (Z)-9-tricosene biosynthesis

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