Ethyl erucate

Base Information

• Chemical Name: Ethyl erucate
• CAS No.: 37910-77-3
• Molecular Formula: C24H46O2
• Molecular Weight: 366.628
• Hs Code.: 2916190090
• European Community (EC) Number: 253-712-0
• UNII: O5A8YB1V2I
• DSSTox Substance ID: DTXSID801317743
• Nikkaji Number: J151.213G
• Wikidata: Q27158156
• Mol file: 37910-77-3.mol

Synonyms:Ethyl erucate;Erucic acid ethyl ester;37910-77-3;Ethyl (Z)-docos-13-enoate;ethyl docos-13-enoate;UNII-O5A8YB1V2I;O5A8YB1V2I;EINECS 253-712-0;13-Docosenoic acid, ethyl ester, (13Z)-;6045-37-0;cis-13-Docosenoic acid ethyl ester;ethyl (13Z)-docosenoate;MFCD00027405;ethyldocos-13-enoate;Ethyl cis-13-Docosenoate;SCHEMBL1109942;ethyl (13Z)-docos-13-enoate;CHEBI:84891;13-Docosenoic acid, ethyl ester;WFZQLUSOXHIVKL-QXMHVHEDSA-N;cis-13-Docosenoic Acidethyl ester;DTXSID801317743;Ethyl (13Z)-13-docosenoate #;Ethyl 13-docosenoate(ethyl erucate);AKOS015839765;HY-W099644;13-Docosenoic acid, ethyl ester, (Z)-;CS-0152286;D1014;Ethyl erucate, ~99% (capillary GC), liquid;Q27158156

Chemical Property of Ethyl erucate

Chemical Property:

• Vapor Pressure: 7.88E-08mmHg at 25°C
• Melting Point: 34 °C
• Refractive Index: 1.4530-1.4570
• Boiling Point: 233 °C / 8.5mmHg
• Flash Point: 82.9°C
• PSA: 26.30000
• Density: 0.87
• LogP: 8.14740
• Storage Temp.: −20°C
• XLogP3: 10.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 21
• Exact Mass: 366.349780706
• Heavy Atom Count: 26
• Complexity: 309

Purity/Quality:

99.9% ^*data from raw suppliers

Erucic Acid Ethyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCCCCCC(=O)OCC
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCCCCCC(=O)OCC
• Uses: Erucic Acid Ethyl Ester is the ethyl ester of Erucic acid (E649900) which is a long-chain alcohol that acts as an inhibitor of fatty acid oxidation in the heart. Erucic acid originates in rapeseed plants, and is the major fatty acid constituent of rapeseed plant oil extracts and canola oil.

Technology Process of Ethyl erucate

There total 5 articles about Ethyl erucate 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:

ethanol (64-17-5) + cis-13-docosenoic acid (112-86-7) → ethyl (13Z)-13-docosenoate (37910-77-3)

Guidance literature:

With sulfuric acid; Reflux;

Reference yield:

ethanol (64-17-5) → ethyl (13Z)-13-docosenoate (37910-77-3)

Guidance literature:

With sulfuric acid;

Reference yield:

docos-13-enoic acid-anhydride (871893-44-6) → cis-13-docosenoic acid (112-86-7) + ethyl (13Z)-13-docosenoate (37910-77-3)

Guidance literature:

erucic acid anhydride;

upstream raw materials:

pyridine

ethanol

docos-13-enoic acid-anhydride

cis-13-docosenoic acid

Downstream raw materials:

ethyl docosanoate

1,23-tricosane diol

Nervonic acid

methyl cis-tetracos-15-enate

Refernces

Epoxidation of Fatty Acid Esters with Aqueous Hydrogen Peroxide in the Presence of Molybdenum Oxide-Tributyltin Chloride on Charcoal Catalyst

10.1246/bcsj.59.3941

Yasushi Irol, Masami INouE, and Saburo Enomoro, investigate the epoxidation of fatty acid esters using 30% aqueous hydrogen peroxide in the presence of a molybdenum oxide-tributyltin chloride on charcoal catalyst in 2-propanol at 50°C. The study demonstrates that various fatty acid esters, including ethyl erucate and ethyl oleate, achieve good yields of 77% and 76%, respectively, while ethyl elaidate, a trans-form, yields only 40%. The epoxidation process selectively maintains the double bond configuration and is more effective for cis-forms due to steric effects. The study also explores the epoxidation of vegetable oils such as rapeseed oil, olive oil, soybean oil, cottonseed oil, corn oil, and linseed oil, with oxirane oxygen contents ranging from 3.5% to 5.3%. The results indicate that the presence of specific fatty acids, like erucic acid in rapeseed oil, significantly influences the epoxidation yield. The study concludes that the use of 30% aqueous hydrogen peroxide is a practical and safer alternative to organic peroxy acids for epoxidation, and the catalyst can be easily separated by filtration.