E2011

cis-5,8,11,14,17-Eicosapentaenoic acid

from fish oil, ≥99% (GC), liquid, 5-Lipoxygenase inhibitor

• Synonym(s): EPA, Timnodonic acid
• Linear Formula: CH₃(CH₂CH=CH)₅(CH₂)₃CO₂H
• CAS Number: 10417-94-4
• Molecular Weight: 302.45
• Beilstein/REAXYS Number: 1714433
• MDL number: MFCD00065716
• UNSPSC Code: 12352211
• PubChem Substance ID: 24894450
• NACRES: NA.77

Properties

• Product Name: cis-5,8,11,14,17-Eicosapentaenoic acid, ≥99%
• biological source: fish oil
• assay: ≥99%
• form: liquid
• refractive index: n20/D 1.4977 (lit.)
• mp: −54-−53 °C (lit.)
• solubility: methanol: 50 mg/mL, clear, colorless
• density: 0.943 g/mL at 25 °C (lit.)
• Storage temp.: −20°C
• SMILES string: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O

Description

General description

Eicosapentaenoic acid is a polyunsaturated fatty acid (PUFAs) and is synthesized from linolenic acid. It is distributed in phospholipid bilayers of the cell membrane, synaptic membranes of the brain and retina.[1] It is obtained majorly from fish oil, seaweed, phytoplankton, and camelina.[2] Being an Omega-3 fatty acid, it shows cis-trans conformations.[3]

Application

cis-5,8,11,14,17-Eicosapentaenoic acid has been used:

• to test pharmacologic effect on steatosis in hepatocytes[4]
• as an analytical standard in Raman spectra measurements to characterize human breast cancer samples[5]
• in lipid peroxidation assay in mouse embryonic fibroblasts and in pre-treatment of cells for cell viability studies[6]

Biochem/physiol Actions

5-Lipoxygenase inhibitor; reduces thromboxane A₂ production.

Eicosapentaenoic acid (EPA) is essential for healthy living and alleviates obesity.[2] It decreases the triglyceride levels by modulating very-low-density lipoprotein(VLDL) levels.[7]

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: 200.1 °F - closed cup
• flash_point_c: 93.4 °C - closed cup
• ppe: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter