(E)-11-Hexadecenyl acetate

Base Information

• Chemical Name: (E)-11-Hexadecenyl acetate
• CAS No.: 56218-72-5
• Molecular Formula: C18H34O2
• Molecular Weight: 282.467
• DSSTox Substance ID: DTXSID30860497
• Nikkaji Number: J1.015.708K,J718H
• Metabolomics Workbench ID: 3988
• Mol file: 56218-72-5.mol

Synonyms:56218-72-5;(E)-11-Hexadecenyl acetate;11E-Hexadecenyl acetate;[(E)-hexadec-11-enyl] acetate;E-11-hexadecenyl acetate;(E)-Hexadec-11-en-1-yl acetate;E-11-Hexadecen-1-ol acetate;(E)-11-Hexadecen-1-ol acetate;11-Hexadecen-1-ol, acetate, (E)-;(11E)-HEXADEC-11-EN-1-YL ACETATE;(11E)-Hexadecenyl Acetate;SCHEMBL434979;SCHEMBL834186;Z-11-HDA;(11E)-11-Hexadecenyl acetate;Acetic acid 11-hexadecenyl ester;DTXSID30860497;(E)-Hexadec-11-en-1-ylacetate;CHEBI:188019;(11E)-11-Hexadecenyl acetate #;LMFA07010343;AKOS015901480;BS-47224;E74911

Chemical Property of (E)-11-Hexadecenyl acetate

Chemical Property:

• Vapor Pressure: 4.93E-05mmHg at 25°C
• Refractive Index: 1.4476 (20℃)
• Boiling Point: 348.7±11.0℃ (760 Torr)
• Flash Point: 88.3±17.6℃
• PSA: 26.30000
• Density: 0.875±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 5.80680
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 282.255880323
• Heavy Atom Count: 20
• Complexity: 234

Purity/Quality:

98%,99%, ^*data from raw suppliers

(11E)-HexadecenylAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=CCCCCCCCCCCOC(=O)C
• Isomeric SMILES: CCCC/C=C/CCCCCCCCCCOC(=O)C
• Uses: (11E)-Hexadecenyl Acetate is a pheromone component.

Technology Process of (E)-11-Hexadecenyl acetate

There total 3 articles about (E)-11-Hexadecenyl 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:

1-hexene (592-41-6,25067-06-5) + (Z)-eicos-11-en-1-yl acetate (66731-37-1) → (Z)-11-hexadecen-1-yl acetate (34010-21-4) + (E)-11-hexadecen-1-yl acetate (56218-72-5)

Guidance literature:

1-hexene; (Z)-eicos-11-en-1-yl acetate; With triethylaluminum; In toluene; at 20 ℃; for 16h; Inert atmosphere; Glovebox;

With (T-4)-[2,6-bis(1-methylethyl)benzenaminato(2-)](6'-bromo-4',5'-diphenyl[1,1':2',1"-terphenyl]-3'-olato-κO)(2,5-dimethyl-1H-pyrrol-1-yl)(2-methyl-2-phenylpropylidene)molybdenum; In toluene; at 20 ℃; for 12h; Inert atmosphere; Glovebox;

Reference yield:

11-hexadecene-1-ol (113789-13-2) + acetic anhydride (108-24-7) → (Z)-11-hexadecen-1-yl acetate (34010-21-4) + (E)-11-hexadecen-1-yl acetate (56218-72-5)

Guidance literature:

With pyridine; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1271/bbb1961.44.257

Reference yield:

n-butyl magnesium bromide (693-03-8) + acetic anhydride (108-24-7) + (Z)-2-(8-phenylthiododec-11-enyloxy)tetrahydro-2H-pyran (98752-56-8) → (Z)-11-hexadecen-1-yl acetate (34010-21-4) + (E)-11-hexadecen-1-yl acetate (56218-72-5)

Guidance literature:

1,2-bis(diphenylphosphino)ethane nickel(II) chloride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) ether, 12 h, room temp., 2.) 80 deg C, 15 h;

upstream raw materials:

n-butyl magnesium bromide

acetic anhydride

(Z)-2-(8-phenylthiododec-11-enyloxy)tetrahydro-2H-pyran

11-hexadecene-1-ol

Downstream raw materials:

E-11-Hexadecenal

trans-11-hexadecen-1-ol

Refernces

• 1、 Fiandanese, Vito,Marchese, Giuseppe,Naso, Francesco,Ronzini, Ludovico. "A General Approach to the Synthesis of Mono-olefinic Insect Sex Pheromones of Z- or E-Configuration". . p. 1115 - 1120. Retrieved 2007/10/02.