An epoxide metabolite of DHA
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(±)19(20)-EpDPA

Item No. 10175

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(19S,20R)-epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid
Synonyms
  • (±)19,20 EDP
  • (±)19,20-epoxy Docosapentaenoic Acid
  • (±)19,20-epoxy DPA
  • (±)19,20-EpDPE
Molecular Formula
C22H32O3
Formula Weight
344.5
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
CC[C@@H]1[C@@H](O1)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(O)=O
InChi Code
InChI=1S/C22H32O3/c1-2-20-21(25-20)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(23)24/h3-4,7-10,13-16,20-21H,2,5-6,11-12,17-19H2,1H3,(H,23,24)/b4-3-,9-7-,10-8-,15-13-,16-14-/t20-,21+/m1/s1
InChi Key
OSXOPUBJJDUAOJ-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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    25 µg

    $50

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    50 µg

    $95

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    100 µg

    $179

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    500 µg

    $743

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    Product Description

    (±)-19(20)-EpDPA is an epoxide metabolite of docosahexaenoic acid (DHA; Item Nos. 90310 | 17950).1 It is formed from DHA by various cytochrome P450 (CYP) isoforms. In vivo, (±)-19(20)-EpDPA (100 ng/animal, i.p.) suppresses hepatic crown-like structure (hCLS) formation and liver fibrosis in wild-type, but not GPR120-deficient, mice in a model of non-alcoholic steatohepatitis (NASH) induced by high-fat diet and carbon tetrachloride (CCl4).2 Intraplantar administration of (±)-19(20)-EpDPA induces acute mechanical hyperalgesia in mice, an effect that can be blocked by the transient receptor potential ankyrin 1 (TRPA1) inhibitor A-967079 (Item No. 15207).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lucas, D., Goulitquer, S., Marienhagen, J., et al. Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450. J. Lipid Res. 51(5), 1125-1133 (2010).

    2. Aoki, H., Isobe, Y., Yoshida, M., et al. Enzymatically-epoxidized docosahexaenoic acid, 19,20-EpDPE, suppresses hepatic crown-like structure formation and nonalcoholic steatohepatitis fibrosis through GPR120. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1868(3), 159275 (2023).

    3. Sun, L., Zhang, J., Niu, C., et al. CYP1B1-derived epoxides modulate the TRPA1 channel in chronic pain. Acta Pharm. Sinica B 1-14 (2022).

    Product Citations

    Woodman, J.W., Cinelli, M.A., Scharmen-Burgdolf, A., et al. Enzymatic synthesis of epoxidized metabolites of docosahexaenoic, eicosapentaenoic, and arachidonic acids. J. Vis. Exp. 148, 10.3791/59770 (2019).

    McDougle, D.R., Watson, J.E., Abdeen, A.A., et al. Anti-inflammatory ω-3 endocannabinoid epoxides. Proc. Natl. Acad. Sci. USA 114(30), E6034-E6043 (2017).

    Caires, R., Sierra-Valdez, F.J., Millet, J.R.M., et al. Omega-3 fatty acids modulate TRPV4 function through plasma membrane remodeling. Cell Reports 21, 245-258 (2017).

    Deng, B.-Q., Luo, Y., Kang, X., et al. Epoxide metabolites of arachidonate and docosahexaenoate function conversely in acute kidney injury involved in GSK3β signaling. Proc. Natl. Acad. Sci. USA 114(47), 12608-12613 (2017).

    Aoyagi, R., Ikeda, K., Isobe, Y., et al. Comprehensive analyses of oxidized phospholipids using a measured MS/MS spectra library. J. Lipid. Res. 58(11), 2229-2237 (2017).