An ω-3 fatty acid
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Eicosapentaenoic Acid

Item No. 90110

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acid
CAS Number
10417-94-4
Synonyms
  • EPA
  • FA 20:5
  • Timnodonic Acid
Molecular Formula
C20H30O2
Formula Weight
302.5
Purity
≥98%
Formulation (Request formulation change)
A 250 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.15 M Tris-HCl pH 8.5: 1 mg/mlDMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS pH 7.2: <100 µg/ml
SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChi Code
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
Side Chain Carbon Sum
20:5
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    50 mg

    $42

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    100 mg

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    250 mg

    $189

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    500 mg

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    Product 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.1 EPA has been shown to offer protection against coronary heart disease, thrombosis, ischemic brain injury, scaly dermatitis, and some inflammatory diseases.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wada, M., DeLong, C.J., Hong, Y.H., et al. Enzymes and receptors of prostaglandin pathways with arachidonic acid-derived versus eicosapentaenoic acid-derived substrates and products. The Journal of Biological Chemisty 282(31), 22254-22266 (2007).

    2. Yerram, N.R., Moore, S.A., and Spector, A.A. Eicosapentaenoic acid metabolism in brain microvessel endothelium: Effect on prostaglandin formation. J. Lipid Res. 30(11), 1747-1757 (1989).

    3. Takeuchi, H., Inoue, J., Yoshida, M., et al. Dietary effects of n-3 eicosapentaenoic acid on essential fatty acid-deficiency symptoms of rats. Agric. Biol. Chem. 53(12), 3225-3232 (1989).

    Product Citations

    Zhang, L.J., Salekeen, R., Soto-Palma, C., et al. Article polyunsaturated lipid senolytics exploit a ferroptotic vulnerability in senescent cells. Cell Press Blue 1(1), 100004 (2026).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. FASEB J. 35(6), e21666 (2021).

    Roberts, L.M., Schwarz, B., Speranza, E., et al. Pulmonary infection induces persistent, pathogen-specific lipidomic changes influencing trained immunity. iScience 24(9), 103025 (2021).

    Zou, Y., Li, H., Graham, E.T., et al. Cytochrome P450 oxidoreductase contributes to phospholipid peroxidation in ferroptosis. Nat. Chem. Biol. 16(3), 302-309 (2020).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites. medRxiv (2020).

    Abraham, E., Kostina, A., Volmert, B., et al. A retinoic acid: YAP1 signaling axis controls atrial lineage commitment. Cell Rep. 44(5), 115687 (2025).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).

    Lahvic, J.L., Ammerman, M., Li, P., et al. Specific oxylipins enhance vertebrate hematopoiesis via the receptor GPR132. PNAS 115(37), 9252-9257 (2018).

    Archambault, A.-S., Turcotte, C., Martin, C., et al. Comparison of eight 15-lipoxygenase (LO) inhibitors on the biosynthesis of 15-LO metabolites by human neutrophils and eosinophils. PLoS One 13(8), e0202424 (2018).

    Gao, B., Han, Y.-H., Wang, L., et al. Eicosapentaenoic acid attenuates dexamethasome-induced apoptosis by inducing adaptive autophagy via GPR120 in murine bone marrow-derived mesenchymal stem cells. Cell Death Dis. 7, e2235 (2016).

    Yamamoto, T., Matsui, H., Yamaji, K., et al. Narrow-spectrum inhibitors targeting an alternative menaquinone biosynthetic pathway of Helicobacter pylori. J. Infect. Chemother. 22(9), 587-595 (2016).

    Huang, C.B., and Ebersole, J.L. A novel bioactivity of omega-3 polyunsaturated fatty acids and their ester derivatives. Mol. Oral Microbiol. 25(1), 75-80 (2010).

    Lucas, D., Goulitquer, S., Marienhagen, J., et al. Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450. J. Lipid Res. 51(5), 1125-1133 (2010).

    Yuan, C., Sidhu, R.S., Kuklev, D.V., et al. Cyclooxygenase allosterism, fatty acid-mediated cross-talk between monomers of cyclooxygenase homodimers. The Journal of Biological Chemisty 284(15), 10046-10055 (2009).