A racemic version of a CYP450 metabolite of arachidonic acid
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(±)11(12)-EET

Item No. 50511

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-10-[(2R,3S)-3-(2Z)-2-octen-1-yl-2-oxiranyl]-5Z,8Z-decadienoic acid
CAS Number
87173-81-7
Synonyms
  • (±)11,12-EpETrE
Molecular Formula
C20H32O3
Formula Weight
320.5
Purity
≥95%
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@H]1O[C@H]1C/C=C\C/C=C\CCCC(=O)O
InChi Code
InChI=1S/C20H32O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h6,8-10,12-13,18-19H,2-5,7,11,14-17H2,1H3,(H,21,22)/b8-6-,12-9-,13-10-/t18-,19+/m1/s1
InChi Key
DXOYQVHGIODESM-LZXKBWHHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $65

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    50 µg

    $104

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    100 µg

    $195

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    500 µg

    $520

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    Product Description

    (±)11(12)-EET is a fully racemic version of the R/S enantiomeric forms biosynthesized from arachidonic acid (Item No. 90010) by cytochrome P450 enzymes.1,2,3 A higher proportion of 11R(12S)-EET (Item No. 9004344) is produced by the CYP450 isoforms CYP2C23 and CYP2C24 while CYP2B2 produces a higher proportion of 11S(12R)-EET (Item No. 9004348) 11(S),12(R)-EET.3 11(12)-EET has been shown, along with 8(9)-EET (Item No. 50351), to play a role in the recovery of depleted calcium pools in cultured smooth muscle cells.4 It also inhibits basolateral 18-pS potassium channels in the renal cortical collecting duct when used at a concentration of 100 nM.5 11(12)-EET (50 µg/kg per day) increases adhesion of isolated peripheral blood leukocytes in a chamber coated with P-selectin and ICAM-1 but does not affect choroidal neovascularization size following laser photocoagulation.6 It also has anti-inflammatory, angiogenic, and cardioprotective properties.7

    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. Capdevila, J.H., Falck, J.R., and Harris, R.C. Cytochrome P450 and arachidonic acid bioactivation: Molecular and functional properties of the arachidonate monooxygenase. J. Lipid Res. 41(2), 163-181 (2000).

    4. Graber, M.N., Alfonso, A., and Gill, D.L. Recovery of Ca2+ pools and growth in Ca2+ pool-depleted cells is mediated by specific epoxyeicosatrienoic acids derived from arachidonic acid. The Journal of Biological Chemisty 272(47), 29546-29553 (1997).

    5. Wang, Z., Wei, Y., Falck, J.R., et al. Arachidonic acid inhibits basolateral K channels in the cortical collecting duct via cytochrome P-450 epoxygenase-dependent metabolic pathways. Am. J. Physiol. Renal Physiol. 294(6), F1441-F1447 (2008).

    6. Hasegawa, E., Inafuku, S., Mulki, L., et al. Cytochrome P450 monooxygenase lipid metabolites are significant second messengers in the resolution of choroidal neovascularization. Proc. Natl. Acad. Sci. USA 114(36), E7545-E7553 (2017).

    7. Spector, A.A. Arachidonic acid cytochrome P450 epoxygenase pathway. J. Lipid Res. 50(Suppl), S52-S56 (2009).

    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).

    Lahvic, J.L., Ammerman, M., Li, P., et al. Specific oxylipins enhance vertebrate hematopoiesis via the receptor GPR132. PNAS 115(37), 9252-9257 (2018).

    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).

    Caires, R., Sierra-Valdez, F.J., Millet, J.R.M., et al. Omega-3 fatty acids modulate TRPV4 function through plasma membrane remodeling. Cell Reports 21, 245-258 (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).

    Sun, P., Lin, D.H., Yue, P., et al. High potassium intake enhances the inhibitory effect of 11,12-EET on ENaC. J. Am. Soc. Nephrol. 21(10), 1667-1677 (2010).