(3E,8Z,11Z)-Tetradeca-3,8,11-trienyl acetate

Base Information

• Chemical Name: (3E,8Z,11Z)-Tetradeca-3,8,11-trienyl acetate
• CAS No.: 163041-94-9
• Molecular Formula: C16H26O2
• Molecular Weight: 250.3764
• European Community (EC) Number: 682-695-6
• UNII: 6CQR9SPA87
• DSSTox Substance ID: DTXSID50700624
• Nikkaji Number: J699.698A
• Wikidata: Q27264506
• Metabolomics Workbench ID: 3951
• Mol file: 163041-94-9.mol

Synonyms:163041-94-9;(3E,8Z,11Z)-Tetradeca-3,8,11-trienyl acetate;(3E,8Z,11Z)-Tetradeca-3,8,11-trien-1-yl acetate;(3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate;[(3E,8Z,11Z)-tetradeca-3,8,11-trienyl] Acetate;Tetradeca-3,8,11-trienyl acetate, (3E,8Z,11Z)-;3E,8Z,11Z-Tetradecatrienyl acetate;UNII-6CQR9SPA87;6CQR9SPA87;(E,Z,Z)-3,8,11-Tetradecatrien-1-ol acetate;3,8,11-Tetradecatrien-1-ol, 1-acetate, (3E,8Z,11Z)-;SCHEMBL1301147;DTXSID50700624;CHEBI:180360;HWPJPNQEVWTZSJ-XBZOLNABSA-N;LMFA07010306;MFCD22581574;3E, 8Z, 11Z-Tetradecatrienyl acetate;(E,Z,Z)-3,8,11-Tetradecatrienyl acetate;CS-0447565;A848793;(3E,8Z,11Z)-3,8,11-Tetradecatrien-1-ol, acetate;(3E,8Z,11Z)-Tetradeca-3,8,11-trien-1-ylacetate;Q27264506;3,8,11-Tetradecatrien-1-ol, acetate, (3E,8Z,11Z)-

Chemical Property of (3E,8Z,11Z)-Tetradeca-3,8,11-trienyl acetate

Chemical Property:

• Boiling Point: 333.6±31.0 °C(Predicted)
• PSA: 26.30000
• Density: 0.903±0.06 g/cm3(Predicted)
• LogP: 4.92620
• Storage Temp.: Amber Vial, Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 11
• Exact Mass: 250.193280068
• Heavy Atom Count: 18
• Complexity: 275

Purity/Quality:

90% ^*data from raw suppliers

(3E,8Z,11Z)-Tetradeca-3,8,11-trienylAcetate(>75%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCCCC=CCCOC(=O)C
• Isomeric SMILES: CC/C=C\C/C=C\CCC/C=C/CCOC(=O)C
• Uses: (3E,8Z,11Z)-Tetradeca-3,8,11-trienyl Acetate is a compound found in the pheromones. It is a major sex pheromone component of the tomato pest.

Technology Process of (3E,8Z,11Z)-Tetradeca-3,8,11-trienyl acetate

There total 40 articles about (3E,8Z,11Z)-Tetradeca-3,8,11-trienyl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

acetic anhydride (108-24-7) + (E3,Z8,Z11)-3,8,11-tetradecatrienyl alcohol (166901-15-1) → (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate (163041-94-9)

Guidance literature:

With dmap; In toluene; at 50 - 70 ℃; for 1.5h;

Reference yield: 94.0%

acetyl chloride (75-36-5) + (E3,Z8,Z11)-3,8,11-tetradecatrienyl alcohol (166901-15-1) → (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate (163041-94-9)

Guidance literature:

With triethylamine; In diethyl ether;

DOI:10.1134/S107042801706001X

Reference yield:

AgNO3 -impregnated silica gel + (8Z,11Z)-8,11-tetradecadien-3-yn-1-ol (166901-14-0) → (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate (163041-94-9)

Guidance literature:

With pyridine; LiAlH₄; acetic anhydride; In diethylene glycol dimethyl ether; ethyl acetate;

upstream raw materials:

acetic anhydride

(E₃,Z₈,Z₁₁)-3,8,11-tetradecatrienyl alcohol

1-(tetrahydropyranyloxy)-4-pentyn

2-pent-2-ynyloxy-tetrahydro-pyran

Refernces

• 1、 Cabezas, Jorge A.. "A new and efficient synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex pheromone component of the tomato leafminer Tuta absoluta". . p. 407 - 410. Retrieved 2019.
• 2、 -. "Method for synthesizing master-tomato-moth pheromone". Paragraph 0020; 0022; 0029-0030. . Retrieved 2020/01/11.
• 3、 Puigmartí, Marc,Bosch, Ma Pilar,Guerrero, Angel. "An Improved and Convenient New Synthesis of the Pheromone Components of the Tomato Leafminer Tuta absoluta". . p. 961 - 968. Retrieved 2015/03/30.