Eicosapentaenoic Acid

Base Information

• Chemical Name: Eicosapentaenoic Acid
• CAS No.: 1553-41-9
• Deprecated CAS: 78957-30-9
• Molecular Formula: C20H30O2
• Molecular Weight: 302.457
• Nikkaji Number: J322.535F,J986.596I
• Wikipedia: Eicosapentaenoic_acid
• NCI Thesaurus Code: C67080
• RXCUI: 90
• ChEMBL ID: CHEMBL4802124
• Mol file: 1553-41-9.mol

Synonyms:5,8,11,14,17-Eicosapentaenoic Acid;5,8,11,14,17-Icosapentaenoic Acid;Acid, Eicosapentanoic;Eicosapentaenoic Acid;eicosapentanoic acid;Icosapent;omega 3 Eicosapentaenoic Acid;omega-3-Eicosapentaenoic Acid;Timnodonic Acid

Chemical Property of Eicosapentaenoic Acid

Chemical Property:

• Vapor Pressure: 4.36E-10mmHg at 25°C
• Refractive Index: 1.512
• Boiling Point: 439.3 °C at 760 mmHg
• Flash Point: 336 °C
• PSA: 37.30000
• Density: 0.941 g/cm³
• LogP: 5.99270
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 13
• Exact Mass: 302.224580195
• Heavy Atom Count: 22
• Complexity: 398

Purity/Quality:

99%, ^*data from raw suppliers

EICOSAPENTAENOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Fatty Acids and Fats
• Canonical SMILES: CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O
• Isomeric SMILES: CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)O
• Recent EU Clinical Trials: CLINICAL, RANDOMIZED, DOUBLE LIND CLINICAL TRIAL TO STUDY THE EFFECT OF PARENTERAL SUPPLEMENTATION WITH FISH OIL EMULSION IN THE NUTRITIONAL SUPPORT IN ESOPHAGECTOMIZED PATIENTS
• Uses: Eicosapentaenoic acid is an important polyunsaturated fatty acid (omega-3) of the marine food chain that serves as a precursor for the prostaglandin-3 and thromboxane-3 families. Its therapeutic use is as an antihyperlipoproteinemic.

Technology Process of Eicosapentaenoic Acid

There total 1 articles about Eicosapentaenoic Acid 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:

arachidonic acid (506-32-1,236743-58-1) → 5,8,11,14,17-eicosapentaenoic acid (1553-41-9)

Guidance literature:

With Saccharomyces cerevisiae IFO10150 expressing Saccharomyces kluyveri ω3 fatty acid desaturase Sk-FAD3; In water; at 30 ℃;

DOI:10.1271/bbb.80361

Reference yield: 68.0%

phorbol (17673-25-5) + 5,8,11,14,17-eicosapentaenoic acid (1553-41-9) → phorbol 12,13,20-trieicosapentaenoate

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmcl.2021.128319

Reference yield: 60.0%

phorbol (17673-25-5) + 5,8,11,14,17-eicosapentaenoic acid (1553-41-9) → phorbol 13,20-dieicosapentaenoate

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmcl.2021.128319

upstream raw materials:

arachidonic acid

Downstream raw materials:

eicosa-5,8,11,14,17-pentaenoic acid

docosahexaenoic acid ethyl ester

C₃₆H₄₇N₃O₇

5,8,11,14,17-eicosapentaenoyl chloride

Refernces