67446-07-5

Basic information

• Product Name: Z-5-DECEN-1-YL ACETATE
• Synonyms: (z)-5-decenyl;(z)-5-decenylacetate;cis-5-decenylacetate;Z-5-DECEN-1-YL ACETATE;5-DECEN-1-OL,ACETATE,(Z)-;CIS-5-DECEN-1-YL ACETATE;(5Z)-1-Acetoxy-5-decene;(5Z)-5-Decen-1-ol acetate
• CAS NO: 67446-07-5
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.3
• EINECS: 266-693-9
• Mol File: 67446-07-5.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 210.5±0.0℃ (760 Torr)
• Flash Point: 62.2±0.0℃
• Appearance: /
• Density: 0.886±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.192mmHg at 25°C
• Refractive Index: 1.4425 (20℃)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Z-5-DECEN-1-YL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: Z-5-DECEN-1-YL ACETATE(67446-07-5)
• EPA Substance Registry System: Z-5-DECEN-1-YL ACETATE(67446-07-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 67446-07-5(Hazardous Substances Data)

Usage

Description

Z-5-Decen-1-yl Acetate, also known as (5Z)-Decenyl Acetate, is an organic compound that serves as an insect sex pheromone semiochemical. It is a key component found in the oil of Heracleum crenatifolium, a plant species known for its aromatic properties. Z-5-DECEN-1-YL ACETATE plays a crucial role in the communication and mating behavior of certain insects, making it a valuable tool in pest control and ecological studies.

Uses

Used in Pest Control Applications:
Z-5-Decen-1-yl Acetate is used as a pheromone lure in pest control strategies, specifically targeting insects that rely on this chemical for mating and communication. By mimicking the natural pheromones released by female insects, it attracts male insects, leading to their capture or disruption of mating patterns, thereby reducing the pest population.
Used in Ecological Research:
In ecological studies, Z-5-Decen-1-yl Acetate is utilized as a semiochemical marker to understand the mating and communication behaviors of various insect species. This knowledge aids in the development of more effective and environmentally friendly pest management techniques, as well as in the conservation of endangered species.
Used in Fragrance Industry:
Z-5-Decen-1-yl Acetate is also used in the fragrance industry due to its unique and pleasant aroma. It can be incorporated into perfumes, colognes, and other scented products to provide a distinct and appealing scent profile.
Used in Agricultural Applications:
In agriculture, Z-5-Decen-1-yl Acetate can be employed to protect crops from insect pests by disrupting their mating and communication processes. This approach can reduce the reliance on chemical pesticides, promoting sustainable and eco-friendly farming practices.
Used in Chemical Synthesis:
As an organic compound, Z-5-Decen-1-yl Acetate can be used as a starting material or intermediate in the synthesis of other complex organic molecules. This makes it valuable in the development of new pharmaceuticals, agrochemicals, and specialty chemicals.

Synthesis Reference(s)

Synthetic Communications, 20, p. 1339, 1990 DOI: 10.1080/00397919008052846

InChI:InChI=1/C12H22O2/c1-3-4-5-6-7-8-9-10-11-14-12(2)13/h6-7H,3-5,8-11H2,1-2H3/b7-6-

Upstream product

• 34009-04-6 phenyl pentyl sulfone 
• 51652-46-1 (Z)-1-(2-tetrahydropyranyloxy)-dec-5-ene 
• 592-41-6 1-hexene 
• 5048-26-0 5-hexenyl acetate 
• 256377-64-7 dec-5-en-1-ol 
• 108-24-7 acetic anhydride 
• 142-29-0 cyclopentene 
• 79837-87-9 (Z)-5-Decensaeure-methylester 
• 6026-86-4 methyl 4-formylbutanoate 
• 139269-63-9 Acetic acid 2-benzenesulfonyl-1-[4-(tetrahydro-pyran-2-yloxy)-butyl]-hexyl ester 
• 139269-64-0 2-((E)-6-Benzenesulfonyl-dec-5-enyloxy)-tetrahydro-pyran 
• 14194-86-6 5-(2-tetrahydropyranyloxy)pentanal 
• 117968-00-0 1-(1-butoxyethoxy)dec-5-yne 
• 16917-50-3 diethyl monoacetal of glutaconaldehyde 

Downstream Products

• 51652-47-2 (Z)-dec-5-en-1-ol 

Relevant articles and documents

Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**

The first continuous flow Z-selective olefin metathesis process is reported. Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. The designed continuous process permits various self-, cross- and macro-ring-closing-metathesis reactions, delivering products in high selectivity and short residence times. This technique is exemplified by direct application to the preparation of a range of pheromones and macrocyclic odorant molecules and culminates in a telescoped Z-selective cross-metathesis/ Dieckmann cyclisation sequence to access (Z)-Civetone, incorporating a serial array of continually stirred tank reactors.

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.

Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates

Compounds of the formula (I) wherein R2 is a branched or unbranched, saturated or ethylenically mono or di unsaturated aliphatic radical, Z is —CH2OH, —CH2OAc or —CHO, m is a whole positive integer of one or more, and Ac is an acetyl group are synthesized by a process wherein a 1-alken-3-yl alkylate, is reacted with a halo alkanol Grignard reagent.