A racemic mixture of arachidonic acid metabolites
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(±)8(9)-DiHET

Item No. 51351

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)8,9-dihydroxy-5Z,11Z,14Z-eicosatrienoic acid
CAS Number
192461-96-4
Synonyms
  • (±)8,9-DiHETrE
Molecular Formula
C20H34O4
Formula Weight
338.5
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
O[C@H](C/C=C\C/C=C\CCCCC)[C@@H](C/C=C\CCCC(O)=O)O
InChi Code
InChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-9-12-15-18(21)19(22)16-13-10-11-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,12-9-,13-10-/t18-,19-/m1/s1
InChi Key
DCJBINATHQHPKO-CALMLMJYSA-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

    $112

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    50 µg

    $209

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    100 µg

    $395

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    250 µg

    $876

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    Product Description

    (±)8(9)-DiHET is an oxylipin and a racemic mixture of the arachidonic acid metabolites 8(S),9(R)-DiHET and 8(R),9(S)-DiHET.1 It is formed from arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) via an (±)8(9)-EET (Item No. 50351) intermediate by epoxide hydrolases. (±)8(9)-DiHET (1 µM) induces cAMP production in primary human coronary artery smooth muscle cells.2 Plasma levels of (±)8(9)-DiHET are increased in a mouse model of osteoarthritic pain induced by destabilization of the medial meniscus, an effect that can be reversed by the soluble epoxide hydrolase (sEH) inhibitor TPPU (Item No. 11120).3 Spinal cord levels of (±)8(9)-DiHET are also increased in a rat model of surgically-induced acute spinal cord injury (SCI).4

    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. Matsumoto, N., Singh, N., Lee, K.S., et al. The epoxy fatty acid pathway enhances cAMP in mammalian cells through multiple mechanisms. Prostaglandins Other Lipid Mediat. 162, 106662 (2022).

    3. Gowler, P.R.W., Turnbull, J., Shahtaheri, M., et al. Clinical and preclinical evidence for roles of soluble epoxide hydrolase in osteoarthritis knee pain. Arthritis Rheumatol. 74(4), 623-633 (2022).

    4. 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).

    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).