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: 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
• InChI: 1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
• InChI key: JAZBEHYOTPTENJ-JLNKQSITSA-N
• Gene Information: human ... ALOX5(240) ; mouse ... ALOX5(11689) , Pparg(19016) ; rat ... ALOX5(25290)

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. It is obtained majorly from fish oil, seaweed, phytoplankton, and camelina. Being an Omega-3 fatty acid, it shows cis-trans conformations.

Application

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

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

Biochem/physiol Actions

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

5-Lipoxygenase inhibitor; reduces thromboxane A₂ production.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 200.1 °F - closed cup
• Flash Point(C): 93.4 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves