Product of non-enzymatic oxidation of EPA
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(±)5-HEPE

Item No. 32200

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)-5-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid
CAS Number
83952-40-3
Molecular Formula
C20H30O3
Formula Weight
318.5
Purity
≥97%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS pH 7.2: 0.8 mg/ml
λmax
236 nm
SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C=C/C(O)CCCC(=O)O
InChi Code
InChI=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
FTAGQROYQYQRHF-FCWZHQICSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $129

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    50 µg

    $245

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    100 µg

    $461

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    250 µg

    $1,025

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    Product 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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.M., 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).

    Product Citations

    Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).

    Dalli, J., Colas, R.A., Walker, M.E., et al. Lipid Mediator Metabolomics via LC-MS/MS Profiling and Analysis. Clinical Metabolomics 59-72 (2018).

    Aoyagi, R., Ikeda, K., Isobe, Y., et al. Comprehensive analyses of oxidized phospholipids using a measured MS/MS spectra library. J. Lipid. Res. 58(11), 2229-2237 (2017).