An oxylipin and arachidonic acid metabolite
Related Products
Enantiomer(s)
90043478R(9S)-EET
Isomer(s)
50351(±)8(9)-EET
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8S(9R)-EET

Item No. 9004345

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z)-7-[(2S,3R)-3-(2Z,5Z)-2,5-undecadien-1-yl-2-oxiranyl]-5-heptenoic acid
CAS Number
123931-39-5
Synonyms
  • 8S(9R)-epoxy-all-cis-5,11,14-Eicosatrienoic Acid
  • 8S(9R)-EpETrE
  • 8S(9R)-Epoxyeicosatrienoic Acid
  • 8S(9R)-epoxy-5(Z),11(Z),14(Z)-ETrE
  • FA 20:4;O
Molecular Formula
C20H32O3
Formula Weight
320.5
Purity
≥95%
Formulation (Request formulation change)
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=C\C[C@@H](O1)[C@@H]1C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,12-9-,13-10-/t18-,19+/m1/s1
InChi Key
DBWQSCSXHFNTMO-ZZMPYBMWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $316

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    50 µg

    $569

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    100 µg

    $1,010

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    500 µg

    $4,420

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    Product Description

    8S(9R)-EET is an oxylipin and a metabolite of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607).1 It is formed via oxidation of arachidonic acid by the cytochrome P450 (CYP) isoforms CYP1A1, CYP1A2, CYP2B1, and CYP2B2. 8S(9R)-EET induces relaxation of precontracted isolated dog epicardial arterioles (EC50 = 121 pM).2 Intrarenal infusion of 8S(9R)-EET (0.5, 1, or 2 µg/kg per minute) induces glomerular vasoconstriction and reduces the glomerular filtration rate in rats.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Capdevila, J.H., Karara, A., Waxman, D.J., et al. Cytochrome P-450 enzyme-specific control of the regio- and enantiofacial selectivity of the microsomal arachidonic acid epoxygenase. The Journal of Biological Chemisty 265(19), 10865-10871 (1990).

    2. 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).

    3. 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).