A racemic version of a CYP450 metabolite of arachidonic acid
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(±)8(9)-EET

Item No. 50351

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(8S,9R)-epoxy-5Z,11Z,14Z-eicosatrienoic acid
Synonyms
  • (±)8,9-EpETrE
Molecular Formula
C20H32O3
Formula Weight
320.5
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS pH 7.2: 1 mg/ml
SMILES
CCCCC/C=C\C/C=C\C[C@@H](O1)[C@@H]1C/C=C\CCCC(O)=O.CCCCC/C=C\C/C=C\C[C@H](O2)[C@H]2C/C=C\CCCC(O)=O
InChi Code
InChI=1S/2C20H32O3/c2*1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h2*6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b2*7-6-,12-9-,13-10-/t18-,19+;18-,19-/m01/s1
InChi Key
ZZPLWOIAXCLWSW-OMDRTMOCSA-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

    $43

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    50 µg

    $77

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    100 µg

    $129

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    500 µg

    $558

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    Product Description

    (±)8(9)-EET is a fully racemic version of the R/S enantiomeric forms biosynthesized from arachidonic acid (Item No. 90010).1,2 (±)8(9)-EET is a major cytochrome P450 (CYP450) metabolite in the renal cortex.3 It activates PPARα in HEK293 cells when used at a concentration of 1 µM but inhibits NF-κB activity induced by IL-1β in a PPARα-dependent and -independent fashion.4 It is also a substrate of COX-1 and COX-2, as measured by oxygen consumption and product formation assays when used at a concentration of 50 µM.5 (8S,9R)-EET (1 µg/kg), but not (8R,9S)-EET, reduces the glomerular filtration rate (GFR) through COX-dependent pre-glomerular vasoconstriction in rats.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chacos, N., Falck, J.R., Wixtrom, C., et al. Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. Biochem. Biophys. Res. Commun. 104(3), 916-922 (1982).

    2. Oliw, E.H., Guengerich, F.P., and Oates, J.A. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. The Journal of Biological Chemisty 257(7), 3771-3781 (1982).

    3. Zhang, J.Y., Prakash, C., Yamashita, K., et al. Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase. Biochem. Biophys. Res. Commun. 183(1), 138-143 (1992).

    4. Bystrom, J., Wray, J.A., Sugden, M.C., et al. Endogenous epoxygenases are modulators of monocyte/macrophage activity. PloS One 6(10), e26591 (2011).

    5. Rand, A.A., Barnych, B., Morisseau, C., et al. Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids. Proc. Natl. Acad. Sci. USA 114(17), 4370-4375 (2017).

    6. Katoh, T., Takahashi, K., Capdevila, J., et al. Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney. Am. J. Physiol. 261(4 Pt 2), F578-F586 (1991).

    Product Citations

    Isse, F.A., Helal, S., El-Sherbeni, A.A., et al. Quantification of epoxyeicosatrienoic acids enantiomers: The development of reliable and practical liquid chromatography mass spectrometry assay. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 1247, 124346 (2024).

    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).

    Kornilov, A., Kennedy, P.D., Aldrovandi, M., et al. Revising the structure of a new eicosanoid from human platelets to 8,9-11,12-diepoxy-13-hydroxy-eicosadienoic acid. The Journal of Biological Chemisty 294(23), 9225-9238 (2019).

    Levi-Rosenzvig, R., Beyer, A.M., Hockenberry, J., et al. 5,6-δ-DHTL, a stable metabolite of arachidonic acid, is a potential EDHF that mediates microvascular dilation. Free Rad. Biol. Med. 103, 87-94 (2017).