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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Eicosapentaenoic Acid ethyl ester

Cayman Chemical Item Number 10008884

EPA-EE; EPA ethyl ester (CAS 86227-47-6)

Eicosapentaenoic Acid ethyl ester (CAS 86227-47-6)

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Description

Fish oils in the diet have anti-inflammatory and cardiovascular benefits due to an abundance of ω-3 polyunsaturated fatty acids (PUFAs), including eicosapentaenoic acid (EPA).1 EPA ethyl ester (EPA-EE) is a stabilized ethyl ester form of this ω-3 C20:5 PUFA. EPA competitively inhibits the metabolism of (ω-6) arachidonic acid by cyclooxygenase enzymes,2 suggesting that EPA-EE may also directly modulate the actions of enzymes involved in fatty acid metabolism. In addition, dietary EPA-EE in rats increases fatty acid β-oxidation enzyme levels,3,4 indicating that EPA-EE may alter the expression of genes related to fatty acid metabolism. Consistent with this concept, dietary supplementation with EPA-EE in rats also down-regulates lipogenic genes, and decreases plasma cholesterol and triglyceride levels.5 Also, in rats fed a high-fat diet, supplementation with EPA-EE blocks induced insulin resistance and corrects changes in adiponectin levels and TNF-α expression.6

1 von Schacky, C. A review of omega-3 ethyl esters for cardiovascular prevention and treatment of increased blood triglyceride levels. Vasc Health Risk Manag 2(3) 251-262 (2006).

2 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. J Biol Chem 282(31) 22254-22266 (2007).

3 Hong, D.D., Takahashi, Y., Kushiro, M., et al. Divergent effects of eicosapentaenoic and docosahexaenoic acid ethyl esters, and fish oil on hepatic fatty acid oxidation in the rat. Biochim Biophys Acta 1635 29-36 (2003).

4 Arachchige, P.G., Takahashi, Y., and Ide, T. Dietary sesamin and docosahexaenoic and eicosapentaenoic acids synergistically increase the gene expression of enzymes involved in hepatic peroxisomal fatty acid oxidation in rats. Metab Clin Exp 55 381-390 (2006).

5 Pérez-Echarri, N., Pérez-Matute, P., Marcos-Gómez, B., et al. Down-regulation in muscle and liver lipogenic genes: EPA ethyl ester treatment in lean and overweight (high-fat-fed) rats. J Nutr Biochem (2008).

6 Pérez-Matute, P., Pérez-Echarri, N., Martínez, J.A., et al. Eicosapentaenoic acid actions on adiposity and insulin resistance in control and high-fat-fed rats: Role of apoptosis, adiponectin and tumor necrosis factor-a. Br J Nutr 97 389-398 (2007).

Synonyms
  • EPA-EE
  • EPA ethyl ester
Formal Name 5Z,​8Z,​11Z,​14Z,​17Z-​eicosapentaenoic acid,​ ethyl ester
CAS Number 86227-47-6
Molecular Formula C22H34O2
Formula Weight 330.5
Formulation A solution in ethanol
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(OCC)​=O

Background Reading

Pérez-Matute, P., Pérez-Echarri, N., Martínez, J.A., et al. Eicosapentaenoic acid actions on adiposity and insulin resistance in control and high-fat-fed rats: Role of apoptosis, adiponectin and tumor necrosis factor-a. Br J Nutr 97 389-398 (2007).

Hong, D.D., Takahashi, Y., Kushiro, M., et al. Divergent effects of eicosapentaenoic and docosahexaenoic acid ethyl esters, and fish oil on hepatic fatty acid oxidation in the rat. Biochim Biophys Acta 1635 29-36 (2003).

Pérez-Echarri, N., Pérez-Matute, P., Marcos-Gómez, B., et al. Down-regulation in muscle and liver lipogenic genes: EPA ethyl ester treatment in lean and overweight (high-fat-fed) rats. J Nutr Biochem (2008).

Arachchige, P.G., Takahashi, Y., and Ide, T. Dietary sesamin and docosahexaenoic and eicosapentaenoic acids synergistically increase the gene expression of enzymes involved in hepatic peroxisomal fatty acid oxidation in rats. Metab Clin Exp 55 381-390 (2006).

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. J Biol Chem 282(31) 22254-22266 (2007).

von Schacky, C. A review of omega-3 ethyl esters for cardiovascular prevention and treatment of increased blood triglyceride levels. Vasc Health Risk Manag 2(3) 251-262 (2006).

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Size Price Quantity Subtotal
10 mg $12.00 $0.00
50 mg $54.00 $0.00
100 mg $96.00 $0.00
500 mg $420.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-02-12. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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