(Z)-9-Tricosene

Last updated
(Z)-9-Tricosene
(Z)-9-tricosene.svg
Names
Preferred IUPAC name
(9Z)-Tricos-9-ene
Other names
(Z)-Tricos-9-ene
Muscalure
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.081
PubChem CID
UNII
Properties
C23H46
Molar mass 322.621 g·mol−1
Density 0.806 g/mL [1]
Boiling point 300 °C (572 °F; 573 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

(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.

Contents

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. [2]

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. [3]

Biosynthesis

(Z)-9-Tricosene is biosynthesized in house flies from nervonic acid. [4] 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) (Z)-9-tricosene biosynthesis.svg
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. [3]

Related Research Articles

Pheromone Secreted or excreted chemical factor that triggers a social response in members of the same species

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 impact the behavior of the receiving individuals. There are alarm pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology. Pheromones are used from basic unicellular prokaryotes to complex multicellular eukaryotes. Their use among insects has been particularly well documented. In addition, some vertebrates, plants and ciliates communicate by using pheromones.

Pitcher plant Carnivorous plant

Pitcher plants are several different carnivorous plants which have modified leaves known as pitfall traps—a prey-trapping mechanism featuring a deep cavity filled with digestive liquid. The traps of what are considered to be "true" pitcher plants are formed by specialized leaves. The plants attract and drown their prey with nectar.

Drug metabolism Biochemical modification of drugs or foreign compounds by living organisms

Drug metabolism is the metabolic breakdown of drugs by living organisms, usually through specialized enzymatic systems. More generally, xenobiotic metabolism is the set of metabolic pathways that modify the chemical structure of xenobiotics, which are compounds foreign to an organism's normal biochemistry, such as any drug or poison. These pathways are a form of biotransformation present in all major groups of organisms and are considered to be of ancient origin. These reactions often act to detoxify poisonous compounds. The study of drug metabolism is called pharmacokinetics.

Indianmeal moth Species of moth

The Indianmeal moth, also spelled as Indian meal moth and Indian-meal moth, is a pyraloid moth of the family Pyralidae. Alternative common names are weevil moth, pantry moth, flour moth or grain moth. The almond moth and the raisin moth are commonly confused with the Indian-meal moth due to similar food sources and appearance. The species was named after being noted for feeding on Indian-meal or cornmeal and it does not occur natively in India as the usage Indian mealmoth would suggest. It is also not to be confused with the Mediterranean flour moth, another common pest of stored grains.

Cabbage looper Species of moth

The cabbage looper is a medium-sized moth in the family Noctuidae, a family commonly referred to as owlet moths. Its common name comes from its preferred host plants and distinctive crawling behavior. Cruciferous vegetables, such as cabbage, bok choy, and broccoli, are its main host plant; hence, the reference to cabbage in its common name. The larva is called a looper because it arches its back into a loop when it crawls.

Insect trap

Insect traps are used to monitor or directly reduce populations of insects or other arthropods, by trapping individuals and killing them. They typically use food, visual lures, chemical attractants and pheromones as bait and are installed so that they do not injure other animals or humans or result in residues in foods or feeds. Visual lures use light, bright colors and shapes to attract pests. Chemical attractants or pheromones may attract only a specific sex. Insect traps are sometimes used in pest management programs instead of pesticides but are more often used to look at seasonal and distributional patterns of pest occurrence. This information may then be used in other pest management approaches.

Bombykol chemical compound

Bombykol is a pheromone released by the female silkworm moth to attract mates. It is also the sex pheromone in the wild silk moth. Discovered by Adolf Butenandt in 1959, it was the first pheromone to be characterized chemically.

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CYP2C9 mammalian protein found in Homo sapiens

Cytochrome P450 2C9 is an enzyme that in humans is encoded by the CYP2C9 gene.

Diamondback moth Species of moth

The diamondback moth, sometimes called the cabbage moth, is a moth species of the family Plutellidae and genus Plutella. The small, grayish-brown moth sometimes has a cream-colored band that forms a diamond along its back. It's believed that the species may have originated in Europe, South Africa, or the Mediterranean region, but it has now spread worldwide.

Sex pheromones are pheromones released by an organism to attract an individual of the opposite sex, encourage them to mate with them, or perform some other function closely related with sexual reproduction. Sex pheromones specifically focus on indicating females for breeding, attracting the opposite sex, and conveying information on species, age, sex and genotype. Non-volatile pheromones, or cuticular contact pheromones, are more closely related to social insects as they are usually detected by direct contact with chemoreceptors on the antennae or feet of insects.

Lanosterol 14 alpha-demethylase protein-coding gene in the species Homo sapiens

Lanosterol 14α-demethylase (CYP51A1) is a cytochrome P450 enzyme that is involved in the conversion of lanosterol to 4,4-dimethylcholesta-8(9),14,24-trien-3β-ol. The cytochrome P450 isoenzymes are a conserved group of proteins that serve as key players in the metabolism of organic substances and the biosynthesis of important steroids, lipids, and vitamins in eukaryotes. As a member of this family, lanosterol 14α-demethylase is responsible for an essential step in the biosynthesis of sterols. In particular, this protein catalyzes the removal of the C-14α-methyl group from lanosterol. This demethylation step is regarded as the initial checkpoint in the transformation of lanosterol to other sterols that are widely used within the cell.

Housefly Species of insect

The housefly 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 fly species found in houses. Adults are gray to black, with four dark, longitudinal lines on the thorax, slightly hairy bodies, and a single pair of membranous wings. They have red eyes, set farther apart in the slightly larger female.

Queen mandibular pheromone, or QMP, is a honey bee pheromone produced by the queen and fed to her attendants who share it with the rest of the colony that gives the colony the sense of belonging to the queen. Newly emerged queens produce very little QMP. By the sixth day they are producing enough to attract drones for mating. A laying queen makes twice that amount. Lack of QMP seems to attract robber bees. A study of foraging worker bees has suggested that foraging bees are not attracted to QMP.

20-Hydroxyeicosatetraenoic acid chemical compound

20-Hydroxyeicosatetraenoic acid, also known as 20-HETE or 20-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid, is an eicosanoid metabolite of arachidonic acid that has a wide range of effects on the vascular system including the regulation of vascular tone, blood flow to specific organs, sodium and fluid transport in the kidney, and vascular pathway remodeling. These vascular and kidney effects of 20-HETE have been shown to be responsible for regulating blood pressure and blood flow to specific organs in rodents; genetic and preclinical studies suggest that 20-HETE may similarly regulate blood pressure and contribute to the development of stroke and heart attacks. Additionally the loss of its production appears to be one cause of the human neurological disease, Hereditary spastic paraplegia. Preclinical studies also suggest that the overproduction of 20-HETE may contribute to the progression of certain human cancers, particularly those of the breast.

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Epoxide docosapentaenoic acids are metabolites of the 22-carbon straight-chain omega-3 fatty acid, docosahexaenoic acid (DHA). Cell types that express certain cytochrome P450 (CYP) epoxygenases metabolize polyunsaturated fatty acid's (PUFAs) by converting one of their double bonds to an epoxide. In the best known of these metabolic pathways, cellular CYP epoxygenases metabolize the 20-carbon straight-chain omega-6 fatty acid, arachidonic acid, to epoxyeicosatrienoic acids (EETs); another CYP epoxygenase pathway metabolizes the 20-carbon omega-3 fatty acid, eicosapentaenoic acid (EPA), to epoxyeicosatetraenoic acids (EEQs). CYP epoxygenases similarly convert various other PUFAs to epoxides These epoxide metabolites have a variety of activities. However, essentially all of them are rapidly converted to their corresponding, but in general far less active, Vicinal (chemistry) dihydroxy fatty acids by ubiquitous cellular Soluble epoxide hydrolase. Consequently, these epoxides, including EDPs, operate as short-lived signaling agents that regulate the function of their parent or nearby cells. The particular feature of EDPs distinguishing them from EETs is that they derive from omega-3 fatty acids and are suggested to be responsible for some of the beneficial effects attributed to omega-3 fatty acids and omega-3-rich foods such as fish oil.

Epoxyeicosatetraenoic acids are a set of biologically active epoxides that various cell types make by metabolizing the omega 3 fatty acid, eicosapentaenoic acid (EPA), with certain cytochrome P450 epoxygenases. These epoxygenases can metabolize EPA to as many as 10 epoxides that differ in the site and/or stereoisomer of the epoxide formed; however, the formed EEQs, while differing in potency, often have similar bioactivities and are commonly considered together.

Cytochrome P450 omega hydroxylases, also termed cytochrome P450 ω-hydroxylases, CYP450 omega hydroxylases, CYP450 ω-hydroxylases, CYP omega hydroxylase, CYP ω-hydroxylases, fatty acid omega hydroxylases, cytochrome P450 monooxygenases, and fatty acid monooxygenases, are a set of cytochrome P450-containing enzymes that catalyze the addition of a hydroxyl residue to a fatty acid substrate. The CYP omega hydroxylases are often referred to as monoxygenases; however, the monooxygenases are CYP450 enzymes that add a hydroxyl group to a wide range of xenobiotic and naturally occurring endobiotic substrates, most of which are not fatty acids. The CYP450 omega hydroxylases are accordingly better viewed as a subset of monooxygenases that have the ability to hydroxylate fatty acids. While once regarded as functioning mainly in the catabolism of dietary fatty acids, the omega oxygenases are now considered critical in the production or break-down of fatty acid-derived mediators which are made by cells and act within their cells of origin as autocrine signaling agents or on nearby cells as paracrine signaling agents to regulate various functions such as blood pressure control and inflammation.

Drosophila nigrospiracula is a fly species indigenous to the Sonoran Desert, spanning Arizona, California, and part of Sonora, Mexico. D. nigrospiracula share the Sonoran Desert with three other species of Drosophila: D. pachea, D. mettleri, and D. mojavensis. D. nigrospiracula do not exhibit sexual isolation between the other species. This fly breeds on the decomposing tissues of two species of cacti that are also endemic to the region: cardón (Pachycereus pringlei) and saguaro (Carnegiea gigantea).

References

  1. 1 2 "(Z)-9-Tricosene". Sigma-Aldrich.
  2. 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.
  3. 1 2 "(Z)-9-Tricosene (103201) Fact Sheet". United States Environmental Protection Agency.
  4. 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. doi:10.1073/pnas.91.21.10000. PMC   44945 . PMID   7937826.