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

(±)5-HEPE

Cayman Chemical Item Number 32200

(CAS 83952-40-3)

(±)5-HEPE (CAS 83952-40-3)

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Description

(±)5-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 5(S)-HEPE and 5(R)-HEPE. The biological activity of (±)5-HEPE is likely mediated by one of the individual isomers, most commonly the 5(S) isomer in mammalian systems. EPA can be metabolized to 5-HEPE in human and bovine neutrophils, and human eosinophils, which is further metabolized to 5-oxoEPE and LTB5.1,2,3 The 5-series metabolites of EPA, namely 5-HEPE, 5-oxoEPE, and LTB5, have significantly decreased biological effects compared to the arachidonic acid-derived metabolites.3

1 Powell, W.S., Gravel, S., and Gravelle, F. Formation of a 5-oxo metabolite of 5,8,11,14,17-eicosapentaenoic acid and its effects on human neutrophils and eosinophils. J Lipid Res 36 2590-2598 (1995).

2 Lee, T.H., Mencia-Huerta, J., Shih, C., et al. Effects of exogenous arachidonic, eicosapentaenoic, and docosahexaenoic acids on the generation of 5-lipoxygenase pathway products by ionophore-activated human neutrophils. J Clin Invest 74 1922-1933 (1984).

3 Taylor, S.M., Laegreid, W.W., Heidel, J.R., et al. EArachidonic and eicosapentaenoic acid metabolism in bovine neutrophils and platelets: Effect of calcium ionophore. J Leukoc Biol 42 253-262 (1987).

Formal Name (±)-​5-​hydroxy-​6E,​8Z,​11Z,​14Z,​17Z-​eicosapentaenoic acid
CAS Number 83952-40-3
Molecular Formula C20H30O3
Formula Weight 318.5
Formulation A solution in ethanol
Purity ≥97%
λmax 236 nm
ε 23
Stability 1 year
Storage -20°C
Shipping Wet ice 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(O)​CCCC(=O)​O

Background Reading

Powell, W.S., Gravel, S., and Gravelle, F. Formation of a 5-oxo metabolite of 5,8,11,14,17-eicosapentaenoic acid and its effects on human neutrophils and eosinophils. J Lipid Res 36 2590-2598 (1995).

Taylor, S.M., Laegreid, W.W., Heidel, J.R., et al. EArachidonic and eicosapentaenoic acid metabolism in bovine neutrophils and platelets: Effect of calcium ionophore. J Leukoc Biol 42 253-262 (1987).

Lee, T.H., Mencia-Huerta, J., Shih, C., et al. Effects of exogenous arachidonic, eicosapentaenoic, and docosahexaenoic acids on the generation of 5-lipoxygenase pathway products by ionophore-activated human neutrophils. J Clin Invest 74 1922-1933 (1984).
Size Price Quantity Subtotal
25 µg $41.00 $0.00
50 µg $78.00 $0.00
100 µg $148.00 $0.00
250 µg $328.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-02-09. 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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5(S)-HEPE
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Eicosapentaenoic Acid
HEPES Stock Solution (1 M)
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