(±)5-HEPE

Cayman Chemical Item Number 32200

(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
InCHI Code
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​1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)​17-15-18-20(22)​23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)​/b4-3-,7-6-,10-9-,13-12-,16-14+
InCHI Key
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FTAGQROYQYQRHF-FCWZHQICSA-N

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(±)5-HEPE is available in the following screening library:

Size Price Quantity Subtotal
25 µg $45.00 $0.00
50 µg $86.00 $0.00
100 µg $162.00 $0.00
250 µg $360.00 $0.00
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Related Products

5(6)-EpETE methyl ester
5(S)-HEPE
5(S)-HpEPE
Eicosapentaenoic Acid
HEPES Stock Solution (1 M)
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Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

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Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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Ann Arbor, Michigan 48108 USA

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