A racemic version of a CYP450 pathway metabolite of arachidonic acid
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(±)5(6)-DiHET

Item No. 51211

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)5,6-dihydroxy-8Z,11Z,14Z-eicosatrienoic acid
CAS Number
213382-49-1
Synonyms
  • (±)5,6-DiHETrE
Molecular Formula
C20H34O4
Formula Weight
338.5
Purity
≥95%
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
CCCCC/C=C\C/C=C\C/C=C\C[C@@H](O)[C@H](O)CCCC(O)=O
InChi Code
InChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(21)19(22)16-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-/t18-,19-/m1/s1
InChi Key
GFNYAPAJUNPMGH-GMKBZGQBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $102

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    50 µg

    $192

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    100 µg

    $357

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    250 µg

    $791

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    Product Description

    5(6)-DiHET is a fully racemic version of the enantiomeric forms biosynthesized from 5(6)-EET (Item Nos. 50211 | 10007260) by epoxide hydrolases.1 5(6)-DiHET can be used to quantify 5(6)-EET due to the conversion of 5(6)-EET to 5(6)-δ-lactone in solution.2 5(6)-DiHET activates large-conductance calcium-activated potassium (KCa1.1/BK) channels in smooth muscle cells from rat small coronary arteries.3 It is a substrate for sheep seminal vesicle COX, producing 5,6-dihydroxy prostaglandin E1 and F1α metabolites in vitro.4 5(6)-DiHET levels decrease in plasma in a high-fat diet-induced rat model of hyperlipidemia.5

    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. Rashid, M., Manivet, P., Nishio, H., et al. Identification of the binding sites and selectivity of sarpogrelate, a novel 5-HT2 antagonist, to human 5-HT2A, 5-HT2B and 5-HT2C receptor subtypes by molecular modeling. Life Sci. 73(2), 193-207 (2003).

    3. Lu, T., Katakam, P.V.G., VanRollins, M., et al. Dihydroxyeicosatrienoic acids are potent activators of Ca2+-activated K+ channels in isolated rat coronary arterial myocytes. J. Physiol. 534(Pt 3), 651-667 (2001).

    4. Oliw, E.H. Biosynthesis of 5,6-dihydroxyprostaglandin E1 and F1α from 5,6-dihydroxyeicosatrienoic acid by ram seminal vesicles. Biochim. Biophys. Acta 795(2), 384-391 (1984).

    5. Miao, H., Zhao, Y.-H., Vaziri, N.D., et al. Lipidomics biomarkers of diet-induced hyperlipidemia and its treatment with Poria cocos. J. Agric. Food Chem. 64(4), 969-979 (2016).

    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).

    Fulton, D., Falck, J.R., McGiff, J.C., et al. A method for the determination of 5,6-EET using the lactone as an intermediate in the formation of the diol. J. Lipid Res. 39(8), 1713-1721 (1998).