An epoxygenase metabolite of EPA
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(±)17(18)-DiHETE

Item No. 10006999

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)17,18-dihydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
Synonyms
  • (±)17,18-dihydroxy-eicosa-5,8,11,14-Tetraenoic Acid
Molecular Formula
C20H32O4
Formula Weight
336.5
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): .5 mg/ml
SMILES
CC[C@@H](O)[C@H](O)C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H32O4/c1-2-18(21)19(22)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-20(23)24/h3,5-6,8-9,11-12,14,18-19,21-22H,2,4,7,10,13,15-17H2,1H3,(H,23,24)/b5-3-,8-6-,11-9-,14-12-/t18-,19-/m1/s1
InChi Key
XYDVGNAQQFWZEF-VXNZHGHESA-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

    $116

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    50 µg

    $215

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    100 µg

    $406

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    Product Description

    (±)17(18)-DiHETE is one of the major metabolites produced when eicosapentaenoic acid (EPA) is incubated with various rat tissue homogenates or cynomolgus monkey seminal vesicles.1,2,3,4 The route of production of (±)17(18)-DiHETE likely proceeds through cytochrome P450-catalyzed epoxidation at the ω-3 double bond followed by conversion to the vicinal diols by epoxide hydrolase. EPA is also metabolized preferentially by Gaeumannomyces graminis to (±)17(18)-DiHETE.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. VanRollins, M., Frade, P.D., and Carretero, O.A. Oxidation of 5,8,11,14,17-eicosapentaenoic acid by hepatic and renal microsomes. Biochim. Biophys. Acta 996, 133-149 (1988).

    2. Yamane, M., Abe, A., and Yamane, S. High-performance liquid chromatography-thermospray mass spectrometry of epoxy polyunsaturated fatty acids and epoxyhydroxy polyunsaturated fatty acids from an incubation mixture of rat tissue homogenate. J. Chromatogr. 652(2), 123-136 (1994).

    3. Oliw, E.H. Biosynthesis of 18(RD)-hydroxyeicosatetraenoic acid from arachidonic acid by microsomes of monkey seminal vesicles. Some properties of a novel fatty acid w 3-hydroxylase and w 3-epoxygenase. The Journal of Biological Chemisty 264(30), 17845-17853 (1989).

    4. Oliw, E.H., and Sprecher, H.W. Metabolism of polyunsaturated (n-3) fatty acids by monkey seminal vesicles: Isolation and biosynthesis of omega-3 epoxides. Biochim. Biophys. Acta 1086(3), 287-294 (1991).

    5. Brodowsky, I.D., and Oliw, E.H. Metabolism of 18:2(n-3), 20:4(n-6), and 2-:5(n-3) by the fungus Gaeumannomyces graminis: Identification of metabolites formed by 8-hydroxylation and by w2 and w3 oxygenation. Biochim. Biophys. Acta 1124, 59-65 (1992).