27519-02-4

Basic information

• Product Name: cis-9-Tricosene
• Synonyms: FLYBAIT;CIS-9-TRICOSENE;9-TRICOSENE;(9Z)-9-Tricosene;(9Z)-Tricosene;(z)-9-tricosen;ai3-35349;ent35349
• CAS NO: 27519-02-4
• Molecular Formula: C₂₃H₄₆
• Molecular Weight: 322.61
• EINECS: 248-505-7
• Product Categories: Pharmaceutical Intermediates;pharmacetical;INSECT HORMONE
• Mol File: 27519-02-4.mol

Chemical Properties

• Melting Point: 0°C
• Boiling Point: 300 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear colourless to slightly yellow liquid
• Density: 0.806 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.16E-06mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• Storage Temp.: -20°C
• Water Solubility: Miscible with water and hexane. Immiscible with alcohol.
• Merck: 14,6309
• BRN: 1841622
• CAS DataBase Reference: cis-9-Tricosene(CAS DataBase Reference)
• NIST Chemistry Reference: cis-9-Tricosene(27519-02-4)
• EPA Substance Registry System: cis-9-Tricosene(27519-02-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-20/21
• Safety Statements: 24/25-36-26
• WGK Germany: 2
• RTECS: YD0807000
• TSCA: Yes
• Hazardous Substances Data: 27519-02-4(Hazardous Substances Data)

Usage

Uses

Used in Insect Control Applications:
cis-9-Tricosene is used as an insect attractant for controlling houseflies. It serves as a coactive ingredient in fly-bait products, helping to lure and trap these insects, thereby reducing their population and preventing the spread of diseases they may carry.
Used in Biochemical Research:
cis-9-Tricosene has potential applications in the field of biochemical research. Its unique properties and ability to attract houseflies make it a valuable molecule for studying insect behavior, pheromone communication, and the development of new pest control strategies.
Used in Agricultural Industry:
In the agricultural industry, cis-9-Tricosene is used as a pest control agent to manage housefly populations. By attracting and controlling these insects, it helps protect crops from damage and reduces the need for chemical pesticides, promoting sustainable farming practices.
Used in Environmental Management:
cis-9-Tricosene is also utilized in environmental management for controlling housefly populations in areas where they can become a nuisance or pose health risks. Its use in fly-bait products helps maintain a cleaner and healthier environment by reducing the presence of these insects in public spaces and residential areas.

Safety Profile

Moderately toxic by skin contact.When heated to decomposition it emits acrid smoke andirritating vapors.

Metabolic pathway

Muscalure is a long chain mono-unsaturated hydrocarbon and the 9,lO-double bond is a reactive site towards biologrcal and non-biological oxidative agents.

Degradation

Muscalure is stable to light and temperatures up to 50 °C for one year.

InChI:InChI=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+

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• 74088-20-3 1-bromo-(Z)-4-tridecene 

Downstream Products

• 35857-62-6 trans-9-tricosene 
• 124-19-6 nonan-1-al 
• 124-25-4 myristylaldehyde 

Relevant articles and documents

The synthesis of long chain dialkylalkynes, dialkyldiynes and their hydrogenation to monoenes and dienes

Long methylenic chain dialkylalkynes have been synthesised in high yield by an improved procedure. The methodology has been extended to nonconjugated diynes. Catalytic hydrogenation with a poisoned palladium catalyst affords cis-monoenes and cis, cis-dienes respectively. An improved synthesis of cis- 9-tricosene is described.

INSECT PHEROMONES AND THEIR ANALOGS. XIV. SYNTHESIS OF MUSCALURE - THE SEX PHEROMONE OF Musca domestica

A new route to the synthesis of tricos-9Z-one - the sex pheromone of the house fly - has been developed.

A stereospecific route to functionalized alkenes from tetrahydrofurfurylic acetates, synthesis of pheromones

Pure Z or E γ-iodoalkenes were prepared by a ring opening-elimination tandem reaction of erythro or threo secondary tetrahydrofurfurylic acetates with Me3SiCl/NaI. Applications to the synthesis of pheromones of Musca domestica and of Orgyia pseudotsugata are reported.

REGIOSELECTION IN THE ALKYLATION OF TRIMETHYLSILYLALLYL ANION- STEREOSELECTIVE SYNTHESIS OF DISUBSTITUTED ALKENES.

The regioselection in the alkylation of trimethylsilylallyl anion can be controlled by the use of Schlosser's base to give predominately γ-product with trans geometry at the double bond.Application of this approach to the synthesis of Z-9-tricosene and the Gypsy month sex pheromone is demonstrated.

A NEW STEREOSELECTIVE SYNTHESIS OF (Z)-9-TRICOSENE, THE SEX ATTRACTANT OF THE COMMON HOUSEFLY

"Muscalure" (9-tricosene) was prepared very readily by an instant-ylid reaction in a highly cis-selective manner although it was found difficult to assess the (Z/E)-ratio with accuracy.

Cobalt-Catalyzed Decarboxylative Methylation and Ethylation of Aliphatic N-(Acyloxy)phthalimides with Organoaluminum Reagents

A cobalt-catalyzed decarboxylative methylation of aliphatic redox-active esters [ N-(acyloxy)phthalimides; RAEs] with trimethylaluminum under mild conditions was developed, providing a method for transforming a carboxylate group into a methyl group without redox fluctuation. Primary and secondary RAEs were both amenable substrates, whereas a tertiary RAE delivered an elimination product. Triethylaluminum was also used to deliver a decarboxylative ethylation product.

Stereoselective Alkyne Hydrogenation by using a Simple Iron Catalyst

The stereoselective hydrogenation of alkynes constitutes one of the key approaches for the construction of stereodefined alkenes. The majority of conventional methods utilize noble and toxic metal catalysts. This study concerns a simple catalyst comprised of the commercial chemicals iron(II) acetylacetonate and diisobutylaluminum hydride, which enables the Z-selective semihydrogenation of alkynes under near ambient conditions (1–3 bar H2, 30 °C, 5 mol % [Fe]). Neither an elaborate catalyst preparation nor addition of ligands is required. Mechanistic studies (kinetic poisoning, X-ray absorption spectroscopy, TEM) strongly indicate the operation of small iron clusters and particle catalysts.

Practical and scalable synthesis of (Z)-9-Tricosene, the housefly sex pheromone

A practical and scalable synthesis of (Z)-9-tricosene, the sex pheromone of the housefly, has been achieved by the addition of one-carbon unit from the readily available (Z)-erucic acid. The synthesis is composed of three consecutive steps, lithium aluminium hydride reduction of erucic acid, tosylation of the resulting alcohol, and copper-catalyzed Kumada- type cross-coupling of the tosylate with methylmagnesium bromide as the key step. This approach is quite straightforward and capable of scale-up synthesis.

Close-range attraction in Lygocoris pabulinus (L.)

Males of the green capsid bug, Lygocoris pabulinus, exhibit a specific courtship behavior, i.e., a vibration of the abdomen. When both live and dead females were offered to males, this vibration behavior was elicited in most of the males tested. When females were dissected into separate body parts, heads, wings, and legs elicited equal responses, while thorax plus abdomen elicited a much lower response. When separate body parts were extracted, the leg extracts elicited significantly stronger responses than any other extract. This suggests that female L. pabulinus legs are either the source of a close-range sex pheromone or that pheromone is accumulated on the legs due to grooming behavior. The leg extracts contained several hydrocarbons such as n-alkenes, n-alkanes, and some methylalkanes. Female extracts contained more (Z)-9-pentacosene and male extracts contained more (Z)-9-heptacosene. Substrates on which females had walked elicited similar responses as female legs, indicating that the pheromone is deposited on the substrate. This enlarges the functional range of low-volatility compounds, which are thought to function only when sexes are in close vicinity or in contact.

Synthesis of sub-units of marine polycyclic ethers by ring-closing metathesis and hydroboration of enol ethers

A novel syntheses of Z-5-dezenol, Z-5-decenyl acetate, Z-7-dodecenol, Z- 7-dodecenyl acetate, Z-9-tricosene, Z-7,8-epoxy-methyloctadecane which are sex pheromone components of Lepidoptera and Diptera orders, have been realized via stereoselective cometathesis of 1,5-cyclooctadiene with ethylene in the presence of MoCls/SiO2-SnMe4 as a key reaction. The male cometathesis product, 1,Z-5,9-decatriene, has been converted into pheromone components monocloned above by regioselective partial hydroboration or hydrozirconation with help of 9-BBN and Cp2ZrHCl, correspondingly. The protonolysis of the obtained zirconosene derivative gave 1,Z-5-decadiene. Hydroboration-oxidation or hydroboration-C2-homologation of the latter but to Z-5- or Z-7 monoene pheromone components. Hydroboration-iodination of terminal double bond in 1,Z-5,9-decatriene, and further cross-coupling of the obtained iodine derivative with convenient lithium cuprates resulted in Z-9- tricosene, the main sex pheromone component of House Fly (Musca Domestica), or in 2-methyl-Z-7-octadecene, the presence of Gypsy Moth (Lymantria Dispar) sex attractant.