Icosapent

Base Information

• Chemical Name: Icosapent
• CAS No.: 10417-94-4
• Deprecated CAS: 25377-48-4
• Molecular Formula: C20H30O2
• Molecular Weight: 302.457
• Hs Code.: 29161900
• UNII: AAN7QOV9EA
• DSSTox Substance ID: DTXSID9041023
• Nikkaji Number: J343.473G
• Wikipedia: Eicosapentaenoic_acid
• Wikidata: Q409990
• NCI Thesaurus Code: C68434
• RXCUI: 90
• Metabolomics Workbench ID: 1099
• ChEMBL ID: CHEMBL460026
• Mol file: 10417-94-4.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 Icosapent

Chemical Property:

• Appearance/Colour: Smell slightly yellow transparent
• Vapor Pressure: 6.04E-09mmHg at 25°C
• Melting Point: -54--53 °C(lit.)
• Refractive Index: n20/D 1.4977(lit.)
• Boiling Point: 439.3 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 336 °C
• PSA: 37.30000
• Density: 0.941 g/cm³
• LogP: 5.99270
• Storage Temp.: −20°C
• Sensitive.: Air & Light Sensitive
• Solubility.: Soluble in methanol
• 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

EicosapentaenoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids,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 ClinicalTrials: Impact of Omega-3 Fatty Acid Oral Therapy on Healing of Chronic Venous Leg Ulcers in Older Adults
• Recent EU Clinical Trials: A randomised, double-blind, placebo-controlled study of eicosapentaenoic acid (EPA-FFA) gastro-resistant capsules to treat hospitalised subjects with confirmed SARS-CoV-2
• Description: EPA is an ω-3 fatty acid abundantly available in marine organisms. It is oxygenated by COX-1 and COX-2 at rates of about 5% and 30%, respectively, compared to arachidonic acid. EPA has been shown to offer protection against coronary heart disease, thrombosis, ischemic brain injury, scaly dermatitis, and some inflammatory diseases.
• Uses: 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. cis-5,8,11,14,17-Eicosapentaenoic acid has been used an analytical standard for the synthesis followed by investigation of pharmacological properties of aconitine-derived lipo-alkaloids. cis-5,8,11,14,17-Eicosapentaenoic acid has been used:to test pharmacologic effect on steatosis in hepatocytesas an analytical standard in Raman spectra measurements to characterize human breast cancer samplesin lipid peroxidation assay in mouse embryonic fibroblasts and in pre-treatment of cells for cell viability studies

Technology Process of Icosapent

There total 66 articles about Icosapent 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: 98.0%

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

Guidance literature:

With ethylenediaminetetraacetic acid; edetate disodium; In ethanol; water; at 60 - 65 ℃; for 2h;

DOI:10.1016/0040-4020(94)00983-2

Reference yield: 93.0%

(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester (2734-47-6) → all cis-5,8,11,14,17-eicosapentaenoic acid (10417-94-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1021/jo00125a065

Reference yield: 85.5%

5,8,11,14,17-eicosapentaynoic acid (5871-07-8) → all cis-5,8,11,14,17-eicosapentaenoic acid (10417-94-4)

Guidance literature:

With hydrogen; Lindlar's catalyst;

upstream raw materials:

(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester

(2S)-1-O-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-2-O-(6Z,9Z,12Z,15Z-octadecatetranoyl)-3-β-D-galactopyranosyl-sn-glycerol

eicosapentaenoic acid ethyl ester

5,8,11,14,17-eicosapentaynoic acid

Downstream raw materials:

triglyceride of eicosapentaenoic acid

(5Z,8Z,11Z,14Z,17Z)-2,3-dihydroxypropyl eicosa-5,8,11,14,17-pentaenoate

1,3-dieicosapentaenoylglycerol

eicosapentaenoic acid ethyl ester

Refernces

• 1、 Irimescu, Roxana,Yasui, Mamoru,Iwasaki, Yugo,Shimidzu, Nobuyoshi,Yamane, Tsuneo. "Enzymatic synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol". . p. 501 - 506. Retrieved 2000.
• 2、 Liu, Shaojun,Zhu, Yamin,Liu, Ning,Fan, Daming,Wang, Mingfu,Zhao, Yueliang. "Antioxidative Properties and Chemical Changes of Quercetin in Fish Oil: Quercetin Reacts with Free Fatty Acids to Form Its Ester Derivatives". . p. 1057 - 1067. Retrieved 2021.
• 3、 Haraldsson, Gudmundur G.,Halldorsson, Arnar,Kulas, Elin. "Chemoenzymatic synthesis of structured triacylglycerols containing eicosapentaenoic and docosahexaenoic acids". . p. 1139 - 1145. Retrieved 2000.
• 4、 Magnusson, Carlos D.,Gudmundsdottir, Anna V.,Haraldsson, Gudmundur G.. "Chemoenzymatic synthesis of a focused library of enantiopure structured 1-O-alkyl-2,3-diacyl-sn-glycerol type ether lipids". . p. 1821 - 1836. Retrieved 2011.
• 5、 -. "COMPOSITIONS AND METHODS FOR THE TREATMENT OF IRRITABLE BOWEL SYNDROME". Paragraph 00130; 00132. . Retrieved 2018/03/06.