A non-enzymatic oxidation product of EPA that inhibits platelet aggregation
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(±)12-HEPE

Item No. 32540

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)-12-hydroxy-5Z,8Z,10E,14Z,17Z-eicosapentaenoic acid
CAS Number
81187-21-5
Molecular Formula
C20H30O3
Formula Weight
318.5
Purity
≥98%
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
237 nm
SMILES
CC/C=C\C/C=C\CC(O)\C=C\C=C\C/C=C\CCCC(=O)O
InChi Code
InChI=1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h3-4,7-11,13-14,17,19,21H,2,5-6,12,15-16,18H2,1H3,(H,22,23)/b4-3-,9-7-,11-8+,13-10-,17-14+
InChi Key
MCRJLMXYVFDXLS-CGNHZTSISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $129

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    50 µg

    $245

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    100 µg

    $460

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    250 µg

    $1,016

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    Product Description

    (±)12-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 12(S)-HEPE and 12(R)-HEPE. The biological activity of (±)12-HEPE is likely mediated by one of the individual isomers, most commonly the 12(S) isomer in mammalian systems. 12-HEPE inhibits platelet aggregation with the same potency as 12-HETE, exhibiting IC50 values of 24 and 25 µM, respectively.1 These compounds are also equipotent as inhibitors of U46619-induced contraction of rat aorta (IC50s = 8.6-8.8 µM).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Takenaga, M., Hirai, A., Terano, T., et al. Comparison of the in vitro effect of eicosapentaenoic acid (EPA)-derived lipoxygenase metabolites on human platelet function with those of arachidonic acid. Thromb. Res. 37, 373-384 (1986).

    2. Karanian, J.W., Kim, H.Y., and Salem, N., Jr. Inhibitory effects of n-6 and n-3 hydroxy fatty acids on thromboxane (U46619)-induced smooth muscle contraction. J. Pharmacol. Exp. Ther. 270(3), 1105-1109 (1994).

    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).

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

    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).

    Gouveia-Figueira, S., Karlsson, J., Deplano, A., et al. Characterisation of (R)-2-(2-fluorobiphenyl-4-yl)-N-(3-methylpyridin-2-yl)propanamide as a dual fatty acid amide hydrolase: Cyclooxygenase inhibitor. PLoS One 10(9), e0139212 (2015).