EPA Chemical Properties

Melting point:

−54-−53 °C(lit.)

Boiling point:

439℃

Density 

0.943 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4977(lit.)

Flash point:

93 °C

storage temp. 

-20°C

solubility 

Soluble in methanol

form 

liquid

pka

4.75±0.10(Predicted)

color 

Colorless to pale yellow

Sensitive 

Air & Light Sensitive

Merck 

14,3531

BRN 

1714433

Stability:

Stable for 1 year as supplied (unopened). After opening, EPA must be stored under inert gas at -80°C. Solutions in DMSO or ethanol should also be stored under inert gas and may be kept at -80°C for up to 2 months.

InChIKey

RRGOKSYVAZDNKR-ARJAWSKDSA-N

LogP

6.232 (est)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8/PG 3

WGK Germany 

3

F 

8-10-23

HazardClass 

8

HS Code 

29161900

MSDS

• Language:English Provider:SigmaAldrich

EPA Usage And Synthesis

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.

Chemical Properties

Colorless Oil

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.

Uses

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.

Uses

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

Definition

ChEBI: An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.

brand name

Decabid (Lilly).

General Description

Eicosapentaenoic acid (cis-5,8,11,14,17), also known as EPA, is a long-chain omega-3 fatty acid. Studies suggests that EPA as well as other fatty acids can serve as biomarkers for cardiovascular disease, and nutritional and metabolic disorders. This certified solution standard is suitable for use as starting material in the preparation of linearity standards, calibrators, or controls in mass spectrometry-based EPA testing applications such as assessment of cardiovascular?disease risk and fatty acid deficiency, and detection and quantification of EPA in nutraceuticals and dietary supplements.

Biochem/physiol Actions

5-Lipoxygenase inhibitor; reduces thromboxane A2 production.

References

1) Lee et al. (1985), Effect of dietary enrichment with eicosapentaenoic and docosahexaenoic acids on in vitro neutrophil and monocyte leukotriene generation and neutrophil function; N. Engl. J. Med., 312 1217 2) Nicholson et al. (2013), The role of marine n-3 fatty acids in improving cardiovascular health: a review; Food Funct., 4 357

EPA(10417-94-4)Related Product Information

• Docosahexaenoic Acid
• DOCOSAHEXAENOIC ACID METHYL ESTER
• CIS-4,7,10,13,16,19-DOCOSAHEXAENOIC ACID METHYL ESTER
• CIS-4,7,10,13,16,19-DOCOSAHEXAENOIC ACID ETHYL ESTER
• 5(Z),8(Z),11(Z),14(Z),17(Z),20(Z)-TRICOSAHEXAENOIC ACID
• CIS-5,8,11,14,17-EICOSAPENTAENOIC ACID METHYL ESTER
• EPA
• EPA
• Cholesteryl Eicosapentaenoate
• ALL CIS 5-8-11-14-17 EPA ETHYL ESTER,ALL CIS-5,8,11,14,17-EICOSAPENTAENOIC ACID ETHYL ESTER,CIS-5,8,11,14,17-EICOSAPENTAENOIC ACID ETHYL ESTER
• EPA
• 1-O-HEXADECYL-2-EICOSAPENTAENOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
• eicosapentaenoic acid ethyl ester
• 12S-HYDROXY-5Z,8Z,10E,14Z,17Z-EICOSAPENTAENOIC ACID
• [5S,12R]-DIHYDROXY-[6Z,8E,10E,14Z,17Z]-EICOSAPENTAENOIC ACID
• (+/-)-5-HYDROXY-6E,8Z,11Z,14Z,17Z-EICOSAPENTAENOIC ACID,5-hydroxy-6,8,11,14,17-eicosapentaenoic acid,5-hydroxy-6,8,11,14,17-eicosapentaenoic acid
• 11R-HYDROXY-5Z,8Z,12E,14Z,17Z-EICOSAPENTAENOIC ACID
• Eicosapentaenoic Acid-d5