163041-87-0

Basic information

• Product Name: 3,8-Tetradecadien-1-ol, acetate, (3E,8Z)- (9CI)
• Synonyms: (3E,8Z)-tetradeca-3,8-dienyl acetate;E3, Z8-tetradecadienyl acetate;trans-3,cis-8-Tetradecadienyl acetate;(E,Z)-3,8-Tetradecadien-1-ol acetate;3,8-Tetradecadien-1-ol, acetate, (3E,8Z)- (9CI)
• CAS NO: 163041-87-0
• Molecular Formula: C16H28O2
• Molecular Weight: 252.39232
• EINECS: -0
• Mol File: 163041-87-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3,8-Tetradecadien-1-ol, acetate, (3E,8Z)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,8-Tetradecadien-1-ol, acetate, (3E,8Z)- (9CI)(163041-87-0)
• EPA Substance Registry System: 3,8-Tetradecadien-1-ol, acetate, (3E,8Z)- (9CI)(163041-87-0)

Safety Data

• Hazardous Substances Data: 163041-87-0(Hazardous Substances Data)

Usage

Description

3,8-Tetradecadien-1-ol, acetate, (3E,8Z)(9CI), also known as 3E,8Z-Tetradecadienyl Acetate, is a chemical compound that serves as a sex pheromone for the moth species S. absoluta, which belongs to the Lepidoptera order and Gelechiidae family. 3,8-Tetradecadien-1-ol, acetate, (3E,8Z)(9CI) is synthesized from cis-4-Decen-1-ol (D225630), which is also a reactant in the production of epoxyisoprostanes, known for their anti-inflammatory properties.

Uses

Used in Pheromone-based Pest Management:
3,8-Tetradecadien-1-ol, acetate, (3E,8Z)(9CI) is used as a sex pheromone for attracting and monitoring the population of S. absoluta moths. This application aids in pest management strategies by enabling farmers and researchers to track and control the spread of these pests, ultimately protecting crops and reducing the need for chemical pesticides.
Used in Chemical Synthesis:
In the chemical industry, 3,8-Tetradecadien-1-ol, acetate, (3E,8Z)(9CI) is used as a reactant in the synthesis of epoxyisoprostanes, which are compounds with anti-inflammatory properties. This application contributes to the development of new pharmaceuticals and therapeutic agents for treating various inflammatory conditions.

Upstream product

• 172960-51-9 (8Z)-1-(tetrahydropyran-2-yloxy)-8-tetradecen-3-yne 
• 150667-91-7 (4E)-1-(Tetrahydropyran-2-yloxy)-4-decene 
• 110-53-2 1-Bromopentane 
• 108-24-7 acetic anhydride 
• 185955-53-7 1-(methoxymethyloxy)pent-4-yne 
• 86301-86-2 (Z)-4-decenyl iodide 
• 69222-06-6 4-decyne-1-ol 
• 1455184-04-9 (E₃,Z₈)-3,8-tetradecadienyl methoxymethyl ether 
• 501665-82-3 5-hydroxy-(E₃)-3-pentenyl methoxymethyl ether 
• 86197-10-6 4-formyl-(E₃)-3-butenyl methoxymethyl ether 
• 501665-53-8 5-acetoxy-(E₃)-3-pentenyl methoxymethyl ether 
• 57074-37-0 (Z)-4-decen-1-ol 
• 177408-61-6 (8Z)-1-(Tetrahydropyran-2-yloxy)-8-tetradecen-3-yne 
• 172960-52-0 (8Z)-1-(Tetrahydropyran-2-yloxy)-8-tetradecen-3-yne 

Relevant articles and documents

Sex pheromone of tomato pest Scrobipalpuloides absoluta (Lepidoptera: Gelechiidae)

The sex attractant of Scrobipalpuloides absoluta females is a 90:10 mixture of (3E, 8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate and (3E,8Z)-3,8-tetradecadien-1-yl acetate. Tetradecadienyl acetates bearing 8Z, 11Z; 3E,8Z; and 3E, 11Z double bonds were synthesized by stereospecific procedures; the mass spectral and gas chromatographic properties of the 3E,8Z isomer were found to be congruent with those of the tetradecadienyl acetate from S. absoluta. In wind tunnel bioassays, a 10:1 mixture of synthetic (3E,8Z, 11Z)-3,8,11-tetradecatrien-1-yl acetate and (3E,8Z)-3,8-tetradecadien-1-yl acetate was highly attractive to S. absoluta males. Interestingly, the presence of (8Z.11Z)-8,11-tetradecadien-1-yl acetate (10%) inhibited the response to (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate completely.

An Improved and Convenient New Synthesis of the Pheromone Components of the Tomato Leafminer Tuta absoluta

A convenient new synthesis of the two pheromone components of the tomato pest Tuta absoluta in high overall yields and high stereoselectivity (30% yield, E,Z,Z 97% for the major compound and 23% yield, E,Z 99% for the minor component) is reported. The approaches compare favorably with others previously described.

Tetradecatrienyl and tetradecadienyl acetates and their use as sex attractants for tomato pests

The present invention is directed to compounds useful as moth attractants and to methods for controlling populations of the tomato moth Scrobipalpuloides absoluta with these compounds. The compounds are 3,8,11-tetradecatrienyl acetates, 3,8-tetradecadienyl acetates, 3,11-tetradecadienyl acetates, and 8,11-tetradecadienyl acetates. Preferred compounds are (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, (3E,8Z)-3,8-tetradecadienyl acetate, (3E,11Z)-3,11 -tetradecadienyl acetate, and (8Z,11Z)-8-11-tetradecadienyl acetate. The compounds can be used as an attractant in moth traps comprising, in addition to the compounds, a moth restraint. Alternatively, the compounds of the present invention can be combined with a biocontrol agent or an insecticide for use as a moth control composition. Synthesis of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate is described.