Eicosapentaenoic acid ethyl ester

Base Information

• Chemical Name: Eicosapentaenoic acid ethyl ester
• CAS No.: 86227-47-6
• Molecular Formula: C22H34 O2
• Molecular Weight: 330.511
• Hs Code.: 29161900
• European Community (EC) Number: 694-907-4
• Nikkaji Number: J391.913G,J208.497J
• Wikipedia: Ethyl_eicosapentaenoic_acid
• Mol file: 86227-47-6.mol

Synonyms:5,8,11,14,17-eicosapentaenoic acid, ethyl ester, (5Z,8Z,11Z,14Z,17Z)-;AMR-101;AMR101;eicosapentaenoic acid ethyl ester;Epadel;ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate;ethyl all-cis-5,8,11,14,17-icosapentaenoate;ethyl eicosapentaenoate;ethyl eicosapentaenoic acid;ethyl icosapentaenoate;ethyl-eicosapentaenoic acid;ethyl-EPA;icosapent ethyl;vascepa

Chemical Property of Eicosapentaenoic acid ethyl ester

Chemical Property:

• Vapor Pressure: 3.65E-07mmHg at 25°C
• Refractive Index: 1.4850 to 1.4890
• Boiling Point: 417°C at 760 mmHg
• Flash Point: 103.1°C
• PSA: 26.30000
• Density: 0,91 g/cm3
• LogP: 6.47120
• Storage Temp.: Refrigerator
• Water Solubility.: Insoluble in water
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 330.255880323
• Heavy Atom Count: 24
• Complexity: 425

Purity/Quality:

98%, ^*data from raw suppliers

cis-5- ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCC=CCC=CCCCC(=O)OCC
• Isomeric SMILES: CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)OCC
• Recent ClinicalTrials: Protective Effect of EPA on Cardiovascular Events
• Recent EU Clinical Trials: Effect of ?-3 polyunsaturated fatty acids on serum albumin concentration in patients with acute heart failure, hypoalbuminemia, and high inflammatory activity
• Uses: Eicosapentaenoic Acid Ethyl Ester is an important polyunsaturated fatty acid of the marine food chain that serves as a precursor for the prostaglandin-3 and thromboxane-3 families. It differs from arachidonic acid (the eicosatetraenoic acid that is a precursor for the prostaglandin and thromboxane-2 families) by the extra double bond between the third and fourth carbons from the “methyl end” of the molecule. Antilipemic. hypolipidemic

Technology Process of Eicosapentaenoic acid ethyl ester

There total 4 articles about Eicosapentaenoic acid ethyl ester 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: 63.0%

all cis-5,8,11,14,17-eicosapentaenoic acid (10417-94-4) + ethanol (64-17-5) → eicosapentaenoic acid ethyl ester (86227-47-6,84494-70-2)

Guidance literature:

at 37 ℃; for 24h; synthesis with lipase modified with palmitoyl group; Boc, lauroyl and Z groups used also;

Reference yield:

all cis-5,8,11,14,17-eicosapentaenoic acid (10417-94-4) + ethanol (64-17-5) + Diethyl carbonate (105-58-8,76619-83-5) → eicosapentaenoic acid ethyl ester (86227-47-6,84494-70-2)

Guidance literature:

With immobilized Candida antarctica Lipase B; In neat (no solvent); at 60 ℃; for 1h; Green chemistry; Enzymatic reaction;

DOI:10.1016/j.molcatb.2012.04.009

Reference yield:

all cis-5,8,11,14,17-eicosapentaenoic acid (10417-94-4) + ethanol (64-17-5) + orthoformic acid triethyl ester (122-51-0) → eicosapentaenoic acid ethyl ester (86227-47-6,84494-70-2)

Guidance literature:

With immobilized Candida antarctica Lipase B; In neat (no solvent); at 60 ℃; for 0.5h; Green chemistry; Enzymatic reaction;

DOI:10.1016/j.molcatb.2012.04.009

upstream raw materials:

all cis-5,8,11,14,17-eicosapentaenoic acid

ethanol

Diethyl carbonate

orthoformic acid triethyl ester

Downstream raw materials:

butanoic acid ethyl ester

triglyceride of eicosapentaenoic acid

all cis-5,8,11,14,17-eicosapentaenoic acid

(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaen-1-ol

Refernces

• 1、 -. "Compositions and methods of omega polyunsaturated fatty acids for the treatment of oral diseases". Page/Page column 2-3. . Retrieved 2011/05/05.
• 2、 Takahashi, Yoshinori,Tanaka, Kaori,Murakami, Mototake,Kawanari, Masami,Kawasaki, Yoshihiro,et al.. "Characteristics of Lipase Modified with Water-soluble Acylating Reagents and Its Esterification Ability". . p. 809 - 812. Retrieved 2007/10/02.