An arachidonic acid metabolite
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(±)14(15)-EET

Item No. 50651

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(14S,15R)-epoxy-5Z,8Z,11Z-eicosatrienoic acid
CAS Number
197508-62-6
Synonyms
  • (±)14,15-EET
  • (±)14,15-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@@H]1[C@@H](O1)C/C=C\C/C=C\C/C=C\CCCC(O)=O.CCCCC[C@H]2[C@H](O2)C/C=C\C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/2C20H32O3/c2*1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h2*4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b2*6-4-,9-7-,13-10-/t18-,19+;18-,19-/m00/s1
InChi Key
ZSUOIKQUEGJWDL-PNXVNNSZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $61

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    50 µg

    $116

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    100 µg

    $218

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    500 µg

    $600

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    Product Description

    (±)14(15)-EET is a metabolite of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) that is formed via epoxidation of arachidonic acid by cytochrome P450.1,2 It prevents increases in leukotriene B4 (LTB4; Item No. 20110), ICAM-1, and chemokine (C-C motif) ligand 1 (CCL2) induced by oxidized LDL in primary rat pulmonary artery endothelial cells (RPAECs) when used at a concentration of 1 μM.3 (±)14(15)-EET induces dilation of preconstricted isolated canine coronary arterioles (EC50 = 0.2 pM).4 It reduces myocardial infarct size as a percentage of the area at risk in a canine model of ischemia-reperfusion injury induced by left anterior descending coronary artery (LAD) occlusion when administered at a dose of 0.128 mg/kg prior to occlusion or reperfusion.5

    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. Jiang, J.-X., Zhang, S.-J., Xiong, Y.-K., et al. EETs attenuate ox-LDL-induced LTB4 production and activity by inhibiting p38 MAPK phosphorylation and 5-LO/BLT1 receptor expression in rat pulmonary arterial endothelial cells. PLoS One 10(6), e0128278 (2015).

    4. Oltman, C.L., Weintraub, N.L., VanRollins, M., et al. Epoxyeicosatrienoic acids and dihydroxyeicosatrienoic acids are potent vasodilators in the canine coronary microcirculation. Circ. Res. 83(9), 932-939 (1998).

    5. Nithipatikom, K., Moore, J.M., Isbell, M.A., et al. Epoxyeicosatrienoic acids in cardioprotection: Ischemic versus reperfusion injury. Am. J. Physiol. Heart Circ. Physiol. 291(2), H537-H542 (2006).

    Product Citations

    Bracken, O.V., Jalali, P., Glanville, J.R.W., et al. Epoxy-oxylipins direct monocyte fate in inflammatory resolution in humans. Nat. Commun. 17(1), 431 (2026).

    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).

    Pang, Y., Liu, X., Zhao, C., et al. LC-MS/MS-based arachidonic acid metabolomics in acute spinal cord injury reveals the upregulation of 5-LOX and COX-2 products. Free Radic. Biol. Med. 193(Pt 1), 363-372 (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).

    Deng, B.-Q., Luo, Y., Kang, X., et al. Epoxide metabolites of arachidonate and docosahexaenoate function conversely in acute kidney injury involved in GSK3β signaling. Proc. Natl. Acad. Sci. USA 114(47), 12608-12613 (2017).

    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).

    Ding, Y., Frömel, T., Popp, R., et al. The biological actions of 11,12-epoxyeicosatrienoic acid in endothelial cells are specific to the R/S-enantiomer and require the Gs protein. J. Pharmacol. Exp. Ther. 350(1), 14-21 (2014).

    Morisseau, C., and Hammock, B.D. Measurement of soluble epoxide hydrolase (sEH) activity. Curr. Protoc. Toxicol. 4.23.2(Suppl. 33), (2007).

    Bernstrom, K., Kayganich, K., Murphy, R.C., et al. Incorporation and distribution of epoxyeicosatrienoic acids into cellular phospholipids. The Journal of Biological Chemisty 267(6), 3686-3690 (1992).