An oxylipin and a metabolite of arachidonic acid
Related Products
Enantiomer(s)
900434811S(12R)-EET
Isomer(s)
50511(±)11(12)-EET
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11R(12S)-EET

Item No. 9004344

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
10-[(2R,3S)-3-(2Z)-2-octen-1-yl-2-oxiranyl]-5Z,8Z-decadienoic acid
CAS Number
123931-38-4
Synonyms
  • 11R(12S)-EpETrE
  • 11R(12S)-Epoxy-all-cis-5,8,14-Eicosatrienoic Acid
  • 11R(12S)-Epoxyeicosatrienoic Acid
  • 11R(12S)-Epoxy-5(Z),8(Z),14(Z)-ETrE
  • FA 20:4;O
Molecular Formula
C20H32O3
Formula Weight
320.5
Purity
≥95%
Formulation
A 250 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Acetonitrile: Sparingly soluble: 1-10 mg/mlEthanol: Slightly soluble: 0.1-1 mg/ml
SMILES
CCCCC/C=C\C[C@H]1[C@H](O1)C/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+/m0/s1
InChi Key
DXOYQVHGIODESM-MFYAFOOZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $329

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    50 µg

    $625

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    100 µg

    $1,053

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    500 µg

    $4,934

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    Product Description

    11R(12S)-EET is an oxylipin and a metabolite of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607).1,2 It is selectively formed from arachidonic acid by the cytochrome P450 (CYP) isoform CYP2C23 and CYP2C24 over CYP2B2, as well as CYP2C8 over CYP2C9. 11R(12S)-EET (50 nM) activates large-conductance calcium-activated potassium channels (KCa1.1/BK) in isolated rat coronary small arterial smooth muscle cells and binds to isolated guinea pig monocytes in a competitive binding assay using [3H]14(15)-EET (Ki = 595.1 nM).3,4 It inhibits the epithelial sodium channel (ENaC) in a patch-clamp assay using isolated rat cortical collecting duct tubules when used at a concentration of 100 nM.5 11R(12S)-EET induces dilation of precontracted isolated canine epicardial arterioles (EC50 = 6.3 pM) and denuded porcine subepicardial arterioles (EC50 = 1.6 pM).3 It induces migration of human umbilical vein endothelial cells (HUVECs) when used at a concentration of 5 µM.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Daikh, B.E., Lasker, J.M., Raucy, J.L., et al. Regio- and stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C91. J. Pharmacol. Exp. Ther. 271(3), 1427-1433 (1994).

    3. Zhang, Y., Oltman, C.L., Lu, T., et al. EET homologs potently dilate coronary microvessels and activate BKCa channels. Am. J. Physiol. Heart Circ. Physiol. 280(6), H2430-H2440 (2001).

    4. Wong, P.Y.-K., Lai, P.-S., and Falck, J.R. Mechanism and signal transduction of 14 (R), 15 (S)-epoxyeicosatrienoic acid (14,15-EET) binding in guinea pig monocytes. Prostaglandins Other Lipid Mediat. 62(4), 321-333 (2000).

    5. 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).

    6. 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).