An internal standard for the quantification of (±)8(9)-EET
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Unlabeled Version(s)
50351(±)8(9)-EET
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(±)8(9)-EET-d11

Item No. 10009532

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(8S,9R)-epoxy-5Z,8Z,14Z-eicosatrienoic-16,16,17,17,18,18,19,19,20,20,20-d11 acid
Synonyms
  • (±)8,9-EET-d11
  • (±)8,9-EpETrE-d11
Molecular Formula
C20H21D11O3
Formula Weight
331.5
Purity
≥99% deuterated forms (d1-d11)
Formulation
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
[2H]C(C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])([2H])C([2H])([2H])/C=C\C/C=C\C[C@@H](O1)[C@@H]1C/C=C\CCCC(O)=O.[2H]C(C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])([2H])C([2H])([2H])/C=C\C/C=C\C[C@H](O2)[C@H]2C/C=C\CCCC(O)=O
InChi Code
InChI=1S/2C20H32O3/c2*1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h2*6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b2*7-6-,12-9-,13-10-/t2*18-,19+/m10/s1/i2*1D3,2D2,3D2,4D2,5D2
InChi Key
ZZPLWOIAXCLWSW-UOYLIILLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    10 µg

    $132

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    25 µg

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    50 µg

    $591

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    Product Description

    (±)8(9)-EET-d11 is intended for use as an internal standard for the quantification of (±)8(9)-EET (Item No. 50351) by GC- or LC-MS. (±)8(9)-EET is a racemic mixture of the R/S enantiomeric forms biosynthesized from arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607).1,2 (±)8(9)-EET is a major cytochrome P450 (CYP) metabolite in the renal cortex.3 It activates PPARα in HEK293 cells when used at a concentration of 1 µM but inhibits NF-κB activity induced by IL-1β in a PPARα-dependent and -independent fashion.4 It is also a substrate of COX-1 and COX-2, as measured by oxygen consumption and product formation assays when used at a concentration of 50 µM.5 (8S,9R)-EET (1 µg/kg), but not (8R,9S)-EET, reduces the glomerular filtration rate (GFR) through COX-dependent pre-glomerular vasoconstriction in rats.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chacos, N., Falck, J.R., Wixtrom, C., et al. Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. Biochem. Biophys. Res. Commun. 104(3), 916-922 (1982).

    2. Oliw, E.H., Guengerich, F.P., and Oates, J.A. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. The Journal of Biological Chemisty 257(7), 3771-3781 (1982).

    3. Zhang, J.Y., Prakash, C., Yamashita, K., et al. Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase. Biochem. Biophys. Res. Commun. 183(1), 138-143 (1992).

    4. Bystrom, J., Wray, J.A., Sugden, M.C., et al. Endogenous epoxygenases are modulators of monocyte/macrophage activity. PloS One 6(10), e26591 (2011).

    5. Rand, A.A., Barnych, B., Morisseau, C., et al. Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids. Proc. Natl. Acad. Sci. USA 114(17), 4370-4375 (2017).

    6. 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).