A DHA epoxygenase metabolite
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(±)7(8)-EpDPA

Item No. 10465

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4Z)-rel-6-[(2R,3S)-3-(2Z,5Z,8Z,11Z)-2,5,8,11-tetradecatetraen-1-yl-2-oxiranyl]-4-hexenoic acid
CAS Number
895127-66-9
Synonyms
  • (±)7,8-EDP
  • (±)7,8-EpDPE
  • (±)7,8-epoxy DPA
  • (±)7,8-epoxy Docosapentaenoic Acid
Molecular Formula
C22H32O3
Formula Weight
344.5
Purity
≥95%
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=C\C/C=C\C/C=C\C/C=C\C[C@@H](O1)[C@@H]1C/C=C\CCC(O)=O.CC/C=C\C/C=C\C/C=C\C/C=C\C[C@H](O2)[C@H]2C/C=C\CCC(O)=O
InChi Code
InChI=1S/2C22H32O3/c2*1-2-3-4-5-6-7-8-9-10-11-12-14-17-20-21(25-20)18-15-13-16-19-22(23)24/h2*3-4,6-7,9-10,12-15,20-21H,2,5,8,11,16-19H2,1H3,(H,23,24)/b2*4-3-,7-6-,10-9-,14-12-,15-13-/t2*20-,21+/m10/s1
InChi Key
XZHMENODFVGTIY-BCJXQMLESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $46

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    50 µg

    $86

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    100 µg

    $160

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    500 µg

    $707

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    Product Description

    (±)7(8)-EpDPA is an epoxide derivative of DHA that is generated by the action of cytochrome P450 epoxygenases.1 It is naturally occurring in plasma and brain and spinal cord tissues and is increased following dietary supplementation with ω-3 fatty acids.2,3 (±)7(8)-EpDPA and other epoxy metabolites of DHA modulate receptor and channel activities to evoke diverse effects, such as promoting vasodilation, inhibiting angiogenesis, and decreasing inflammatory and neuropathic pain.3,4,5,6 (±)7(8)-EpDPA is a substrate of soluble epoxide hydrolase (KM = 15 µM), which converts it to the corresponding diol.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Spector, A.A., and Kim, H.Y. Cytochrome P450 epoxygenase pathway of polyunsaturated fatty acid metabolism. Biochim. Biophys. Acta 1851(4), 356-365 (2015).

    2. Fischer, R., Konkel, A., Mehling, H., et al. Dietary omega-3 fatty acids modulate the eicosanoid profile in man primarily via the CYP-epoxygenase pathway. J. Lipid Res. 55(6), 1150-1164 (2014).

    3. Morisseau, C., Inceoglu, B., Schmelzer, K., et al. Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids. J. Lipid Res. 51, 3481-3490 (2010).

    4. Zhang, G., Panigrahy, D., Mahakian, L.M., et al. Epoxy metabolites of docosahexaenoic acid (DHA) inhibit angiogenesis, tumor growth, and metastasis. Proc. Natl. Acad. Sci. USA 110(16), 6530-6535 (2013).

    5. Wang, R., Chai, Q., Lu, T., et al. Activation of vascular BK channels by docosahexaenoic acid is dependent on cytochrome P450 epoxygenase activity. Cardiovasc. Res. 90, 344-352 (2011).

    6. Sato, K., Chino, D., Nishioka, N., et al. Pharmacological evidence showing significant roles for potassium channels and CYP epoxygenase metabolites in the relaxant effects of docosahexaenoic acid on the rat aorta contracted with U46619. Biol. Pharm. Bull. 37(3), 394-403 (2014).