An epoxygenase metabolite of DHA
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(±)19(20)-DiHDPA

Item No. 10007001

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)19,20-dihydroxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid
Synonyms
  • 19(20)-DHDP
  • (±)19,20-DiHDoPE
Molecular Formula
C22H34O4
Formula Weight
362.5
Purity
≥98%
Formulation (Request formulation change)
A 500 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 0.25 mg/ml
SMILES
CC[C@@H](O)[C@@H](O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(O)=O
InChi Code
InChI=1S/C22H34O4/c1-2-20(23)21(24)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(25)26/h3-4,7-10,13-16,20-21,23-24H,2,5-6,11-12,17-19H2,1H3,(H,25,26)/b4-3-,9-7-,10-8-,15-13-,16-14-/t20-,21+/m1/s1
InChi Key
FFXKPSNQCPNORO-MWEXLPNRSA-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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    50 µg

    $94

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    100 µg

    $160

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    500 µg

    $655

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    1 mg

    $1,029

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    Product Description

    Docosahexaenoic acid (DHA; Item No. 90310) is an essential fatty acid and the most abundant ω-3 fatty acid in neural tissues, especially in the retina and brain.1 (±)19(20)-DiHDPA is one of the major metabolites produced when DHA is incubated with NADPH-supplemented rat liver microsomes.2 DHA is also slowly metabolized by monkey seminal vesicles to (±)19(20)-DiHDPA.3 The route of production likely proceeds through cytochrome P450-catalyzed epoxidation at the ω-3 double bond, followed by conversion to the vicinal diols by epoxide hydrolase.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Salem, N., Kim, H.Y., and Yergey, J.A. Docosahexaenoic acid: Membrane function and metabolism. Health effects of polyunsaturated fatty acids in seafoods 263-317 (1986).

    2. VanRollins, M., Baker, R.C., Sprecher, H., et al. Oxidation of docosahexaenoic acid by rat liver microsomes. The Journal of Biological Chemisty 259(9), 5776-5783 (1984).

    3. 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).

    Product Citations

    Walker, R.E., Savinova, O.V., Pedersen, T.L., et al. Effects of inflammation and soluble epoxide hydrolase inhibition on oxylipin composition of very low-density lipoproteins in isolated perfused rat livers. Physiol. Rep. 9(4), e14480 (2021).

    Brouwers, H., Jónasdóttir, H.S., Kuipers, M.E., et al. Anti-inflammatory and proresolving effects of the omega-6 polyunsaturated fatty acid adrenic acid. J. Immunol. 205(10), 2840-2849 (2020).