An EPA metabolite
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20-HEPE

Item No. 19322

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
20-hydroxy-5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acid
CAS Number
116477-57-7
Molecular Formula
C20H30O3
Formula Weight
318.5
Purity
≥95%
Formulation
A 100 µg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: miscibleDMSO: miscibleEthanol: misciblePBS (pH 7.2): 0.8 mg/ml
SMILES
OCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H30O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12-13,15,21H,2,5,8,11,14,16-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-,15-13-
InChi Key
PPMOWWAALQWWLJ-NUKMUHRASA-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

    $286

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    50 µg

    $544

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    100 µg

    $1,030

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    Product Description

    20-HEPE is a metabolite of eicosapentaenoic acid (EPA; Item Nos. 90110 | 21908 | 90110.1) that is formed via ω-oxidation of EPA by cytochrome P450 (CYP) ω-oxidases, including human CYP4F3B.1 It activates peroxisome proliferator-activated receptor α (PPARα) in COS-7 cells expressing a luciferase reporter when used at a concentration of 10 μM. 20-HEPE also activates murine transient receptor potential vanilloid receptor 1 (mTRPV1) in vitro but lacks antinociceptive activity in rats.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Harmon, S.D., Fang, X., Kaduce, T.L., et al. Oxygenation of ω-3 fatty acids by human cytochrome P450 4F3B: Effect on 20-hydroxyeicosatetraenoic acid production. Prostaglandins Leukot. Essent. Fatty Acids 75(3), 169-177 (2006).

    2. Hwang, S.H., Wagner, H., Xu, J., et al. Chemical synthesis and biological evaluation of ω-hydroxy polyunsaturated fatty acids. Bioorg. Med. Chem. Lett. 27(3), 620-625 (2017).