A racemic version of a CYP450 metabolite of arachidonic acid
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(±)5(6)-EET

Item No. 50211

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(5S,6R)-epoxy-8Z,11Z,14Z-eicosatrienoic acid
CAS Number
87173-80-6
Synonyms
  • (±)5,6-EpETrE
Molecular Formula
C20H32O3
Formula Weight
320.5
Purity
≥95% (mixture of free acid and lactone)
Formulation
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=C\C[C@@H](O1)[C@@H]1CCCC(O)=O.CCCCC/C=C\C/C=C\C/C=C\C[C@H](O2)[C@H]2CCCC(O)=O
InChi Code
InChI=1S/2C20H32O3/c2*1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h2*6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b2*7-6-,10-9-,13-12-/t18-,19+;18-,19-/m00/s1
InChi Key
AKCCLLJWTPCYDT-NLKRHHKJSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $50

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    50 µg

    $90

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    100 µg

    $156

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    500 µg

    $481

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    Product Description

    5(6)-EET is a fully racemic version of the enantiomeric forms biosynthesized from arachidonic acid (Item No. 90010) by cytochrome P450 enzymes.1,2 In solution, 5(6)-EET degrades into 5,6-DiHET and 5(6)-δ-lactone, which can be converted to 5(6)-DiHET and quantified by GC-MS.3 In neuroendocrine cells, such as the anterior pituitary and pancreatic islets, 5(6)-EET has been implicated in the mobilization of calcium and hormone secretion.4,5 5(6)-EET is an inhibitor of T-type voltage-gated calcium channels (Cav3) that inhibits isoforms Cav3.1, Cav3.2 (IC50 = 0.54 µM), and Cav3.3 and decreases nifedipine-resistant phenylephrine-induced vasoconstriction in isolated mouse mesenteric arteries via Cav3.2 blockade when used at a concentration of 3 µM.6 In addition, it is 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.7 (±)5(6)-EET is provided as a mixture of the free acid and lactone.

    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. Rashid, M., Manivet, P., Nishio, H., et al. Identification of the binding sites and selectivity of sarpogrelate, a novel 5-HT2 antagonist, to human 5-HT2A, 5-HT2B and 5-HT2C receptor subtypes by molecular modeling. Life Sci. 73(2), 193-207 (2003).

    4. Snyder, C., Lattanzio, F., Yadagiri, P., et al. 5,6-Epoxyeicosatrienoic acid mobilizes Ca2+ in anterior pituitary cells. Biochem. Biophys. Res. Commun. 139(3), 1188-1194 (1986).

    5. Falck, J.R., Manna, S., Moltz, J., et al. Epoxyeicosatrienoic acids stimulate glucagon and insulin release from isolated rat pancreatic islets. Biochem. Biophys. Res. Commun. 114(2), 743-749 (1983).

    6. Cazade, M., Bidaud, I., Hansen, P.B., et al. 5,6-EET potently inhibits T-type calcium channels: Implication in the regulation of the vascular tone. Pflugers Arch. 466(9), 1759-1768 (2014).

    7. 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).

    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).

    Cheng, D., Zinker, B.A., Luo, Y., et al. MGAT2 inhibitor decreases liver fibrosis and inflammation in murine NASH models and reduces body weight in human adults with obesity. Cell Metab. 34(11), 1732-1748 (2022).

    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).

    Fulton, D., Falck, J.R., McGiff, J.C., et al. A method for the determination of 5,6-EET using the lactone as an intermediate in the formation of the diol. J. Lipid Res. 39(8), 1713-1721 (1998).