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  • E2011 - cis-5,8,11,14,17-Eicosapentaenoic acid

E2011 Sigma-Aldrich

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


Synonym: EPA, Timnodonic acid

  • CAS Number 10417-94-4

  • Linear Formula CH3(CH2CH=CH)5(CH2)3CO2H

  • Molecular Weight 302.45

  •  Beilstein/REAXYS Number 1714433

  •  MDL number MFCD00065716

  •  PubChem Substance ID 24894450

  •  NACRES NA.77



Related Categories Allium sativum (Garlic), Arachidonic Acid Cascade, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents,
Quality Level   200
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-
Gene Information   human ... ALOX5(240)
mouse ... ALOX5(11689), Pparg(19016)
rat ... ALOX5(25290)


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.


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


10, 25, 50, 100 mg in ampule

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 & Documentation

Safety Information

NONH for all modes of transport
WGK Germany 
Flash Point(F) 
200.1 °F - closed cup
Flash Point(C) 
93.4 °C - closed cup


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles


Discover Bioactive Small Molecules for Lipid Signaling Research

Within mammalian cells, a multitude of lipid compounds are found with a variety of cellular functions, including structural components of cell membranes and as second messengers in cell signaling pat...
Keywords: Absorption, Atomic absorption spectroscopy, Cancer, Cardiovascular, Cell signaling, Diabetes, Digestions, Diseases, Growth factors, Hormones, Inflammation, Lipid Metabolism, Lipid signaling, Metabolism

FAMLS Online Plate Map

FAMLS compounds are conveniently provided at 5µg per well, enough for multiple injections. These are high purity (>95%) compounds supplied in an economical, ready to use format. Compounds are arrange...
Keywords: Metabolites

Omega-3 Fatty Acids and Heart Disease

The potential for the prevention and treatment of cardiovascular disease through increased dietary intake of omega-3 (w-3) fish oils is not a recent scientific discovery. A historically important stu...
BioFiles 2007, 2.2, 14.
Keywords: Anti-inflammatory agents, Biochemistry, Cardiovascular, Clinical, Degradations, Esterifications, Immunology, Inflammation, Lipid Metabolism, Metabolism, Metabolites, Methods, Nutrition, Oxidations, Transcription

Peer-Reviewed Papers


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