An epoxide metabolite and potent vasodilator
Related Products
Labeled Version(s)
10007975(±)11(12)-DiHET-d11
Parent Compound(s)
50511(±)11(12)-EET
Technical Support & Resources

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(±)11(12)-DiHET

Item No. 51511

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)11,12-dihydroxy-5Z,8Z,14Z-eicosatrienoic acid
Synonyms
  • (±)11,12-DiHETrE
Molecular Formula
C20H34O4
Formula Weight
338.5
Purity
≥95%
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@@H](O)[C@H](O)C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H34O4/c1-2-3-4-5-9-12-15-18(21)19(22)16-13-10-7-6-8-11-14-17-20(23)24/h6,8-10,12-13,18-19,21-22H,2-5,7,11,14-17H2,1H3,(H,23,24)/b8-6-,12-9-,13-10-/t18-,19-/m1/s1
InChi Key
LRPPQRCHCPFBPE-FYVRRLHDSA-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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    25 µg

    $118

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    50 µg

    $224

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    100 µg

    $424

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    Product Description

    Epoxide hydrolases convert the EETs into vicinal diols, with the concurrent loss of much of their biological activity.1 (±)11(12)-DiHET relaxes U-46619 (Item No. 16450)-contracted artery rings with approximately 70% of the magnitude of (±)11(12)-EET (Item No. 50511).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Fang, X., Kaduce, T.L., Weintraub, N.L., et al. Functional implications of a newly characterized pathway of 11,12-epoxyeicosatrienoic acid metabolism in arterial smooth muscle. Circ. Res. 79(4), 784-793 (1996).

    Product Citations

    Pang, Y., Liu, X., Zhao, C., et al. LC-MS/MS-based arachidonic acid metabolomics in acute spinal cord injury reveals the upregulation of 5-LOX and COX-2 products. Free Radic. Biol. Med. 193(Pt 1), 363-372 (2022).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).

    Lahvic, J.L., Ammerman, M., Li, P., et al. Specific oxylipins enhance vertebrate hematopoiesis via the receptor GPR132. PNAS 115(37), 9252-9257 (2018).

    Ding, Y., Frömel, T., Popp, R., et al. The biological actions of 11,12-epoxyeicosatrienoic acid in endothelial cells are specific to the R/S-enantiomer and require the Gs protein. J. Pharmacol. Exp. Ther. 350(1), 14-21 (2014).