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E2011

Sigma-Aldrich

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

≥99%

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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

biological source

fish oil

Quality Level

200

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)

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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.

WGK

WGK 3

Flash Point(F)

200.1 °F

Flash Point(C)

93.4 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Che-Hsin Lee et al.
International journal of molecular sciences, 15(6), 10334-10349 (2014-06-12)
Recent studies have shown that free fatty acids are associated with chronic inflammation, which may be involved in vascular injury. The intake of eicosapentaenoic acid (EPA) can decrease cardiovascular disease risks, but the protective mechanisms of EPA on endothelial cells
Nutrition and traumatic brain injury: improving acute and subacute health outcomes in military personnel (2011)
Docosahexaenoic acid enhances methylmercury-induced endoplasmic reticulum stress and cell death and eicosapentaenoic acid potentially attenuates these effects in mouse embryonic fibroblasts
Takanezawa Y, et al.
Toxicology Letters, 306(15), 35-42 (2019)
Effect of eicosapentaenoic acid and docosahexaenoic acid on myogenesis and mitochondrial biosynthesis during murine skeletal muscle cell differentiation
Hsueh TY, et al.
Frontiers in nutrition, 5, 15-15 (2018)
Omega-3 fatty acids eicosapentaenoic acid and docosahexaenoic acid and their mechanisms of action on apolipoprotein B-containing lipoproteins in humans: a review
Oscarsson J and Hurt-Camejo E
Lipids in Health and Disease, 16(1), 149-149 (2017)
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