A cytochrome P450 metabolite of AEA
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(±)8(9)-EET Ethanolamide

Item No. 10008597

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-(±)8(9)-epoxy-5Z,11Z,14Z-eicosatrienoic amide
Synonyms
  • (±)8,9-EET Ethanolamide
Molecular Formula
C22H37NO3
Formula Weight
363.5
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=C\C/C=C\C[C@H]1O[C@H]1C/C=C\CCCC(=O)NCCO
InChi Code
InChI=1S/C22H37NO3/c1-2-3-4-5-6-7-8-9-12-15-20-21(26-20)16-13-10-11-14-17-22(25)23-18-19-24/h6-7,9-10,12-13,20-21,24H,2-5,8,11,14-19H2,1H3,(H,23,25)/b7-6-,12-9-,13-10-/t20-,21+/m1/s1
InChi Key
BXHPMUQFGGSDAK-PDFUHZMOSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $98

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    50 µg

    $185

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    100 µg

    $347

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    Product Description

    (±)8(9)-EET ethanolamide is a CYP450 metabolite of AEA, although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism.1 Human liver microsomes metabolize AEA to 5,6-, 8,9-, 11,12-, and 14,15-EET ethanolamides in a time and protein concentration dependent manner.1 (±)8(9)-EET reduces glomerular filtration rate through cyclooxygenase dependent preglomerular vasoconstriction.2 The physiological actions of (±)8(9)-EET ethanolamide have not been examined.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Snider, N.T., Kornilov, A.M., Kent, U.M., et al. Anandamide metabolism by human liver and kidney microsomal cytochrome P450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J. Pharmacol. Exp. Ther. 321(2), 590-597 (2007).

    2. Katoh, T., Takahashi, K., Capdevila, J., et al. Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney. Am. J. Physiol. 261(4 Pt 2), F578-F586 (1991).