A cytochrome P450 metabolite of arachidonic acid
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14S(15R)-EET methyl ester

Item No. 28631

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z,8Z,11Z)-13-[(2S,3R)-3-pentyloxiranyl]-5,8,11-tridecatrienoic acid, methyl ester
CAS Number
110901-52-5
Molecular Formula
C21H34O3
Formula Weight
334.5
Purity
≥95%
Formulation (Request formulation change)
A solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: Soluble
SMILES
COC(CCC/C=C\C/C=C\C/C=C\C[C@H](O1)[C@H]1CCCCC)=O
InChi Code
InChI=1S/C21H34O3/c1-3-4-13-16-19-20(24-19)17-14-11-9-7-5-6-8-10-12-15-18-21(22)23-2/h5,7-8,10-11,14,19-20H,3-4,6,9,12-13,15-18H2,1-2H3/b7-5-,10-8-,14-11-/t19-,20+/m1/s1
InChi Key
MQCWCUDQEBWUAM-AWVFLLPBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    10 µg

    $134

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    25 µg

    $316

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    50 µg

    $565

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    100 µg

    $926

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    Product Description

    14S(15R)-EET methyl ester is an oxylipin and a cytochrome P450 metabolite of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607).1 14S(15R)-EET methyl ester binds to isolated guinea pig monocytes with a Ki value of 612.5 nM in a competitive binding assay using [3H]14(15)-EET.2 It induces dilation of precontracted isolated canine epicardial arterioles (EC50 = 4 pM) and denuded porcine subepicardial arterioles (EC50 = 3 pM).3 Unlike 14R(15S)-EET, 14S(15R)-EET methyl ester does not inhibit COX in enzyme assays or isolated platelets.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. 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).

    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. Fitzpatrick, F.A., Ennis, M.D., Baze, M.E., et al. Inhibition of cyclooxygenase activity and platelet aggregation by epoxyeicosatrienoic acids. The Journal of Biological Chemisty 261(2), 15334-15338 (1986).