An antagonist of EDHF-mediated vasodilation
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14,15-EE-5(Z)-E

Item No. 10004946

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-13-[(2R,3S)-3-pentyloxiranyl]-5Z-tridecenoic acid
CAS Number
519038-92-7
Synonyms
  • 14,15-Epoxyeicosa-5(Z)-enoic Acid
Molecular Formula
C20H36O3
Formula Weight
324.5
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 0.5 mg/ml
SMILES
CCCCC[C@@H]1[C@@H](O1)CCCCCCC/C=C\CCCC(O)=O.CCCCC[C@H]2[C@H](O2)CCCCCCC/C=C\CCCC(O)=O
InChi Code
InChI=1S/2C20H36O3/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*7,9,18-19H,2-6,8,10-17H2,1H3,(H,21,22)/b2*9-7-/t18-,19+;18-,19-/m00/s1
InChi Key
SYAJXMQYQJYJEP-HYTOGOHYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $49

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    50 µg

    $93

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    100 µg

    $171

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    500 µg

    $748

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    Product Description

    Epoxyeicosatrienoic acids (EETs), such as 11(12)-EET and 14(15)-EET, are cytochrome P450 metabolites of arachidonic acid that have been identified as endothelium-derived hyperpolarizing factors with vasodilator activity.1 14,15-EE-5(Z)-E is a structural analog of 14,15-epoxyeicosatrienoic acids (14,15-EET) that antagonizes EET-induced relaxation of vascular smooth muscle.2 Relaxation of U46619-constricted bovine arteries by 14,15-EET could be inhibited approximately 80% by 14,15-EE-5(Z)-E at a concentration of 10 µM. 14,15-EE-5(Z)-E does not appear to antagonize nitric oxide- or iloprost-mediated vascular relaxation.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fleming, I. Cytochrome P450 epoxygenases as EDHF synthase(s). Pharmacol. Res. 49(6), 525-533 (2004).

    2. Gauthier, K.M., Deeter, C., Krishna, U.M., et al. 14,15-Epoxyeicosa-5(Z)-enoic acid: A selective epoxyeicosatrienoic acid antagonist that inhibits endothelium-dependent hyperpolarization and relaxation in coronary arteries. Circ. Res. 90(9), 1028-1036 (2002).