A DHA metabolite
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19S(20R)-EpDPA

Item No. 28627

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
18-[(2S,3R)-3-ethyl-2-oxiranyl]-4Z,7Z,10Z,13Z,16Z-octadecapentaenoic acid
CAS Number
2460392-58-7
Synonyms
  • 19S,20R-EDP
  • 19S,20R-EpDPE
  • 19S,20R-epoxy DPA
  • 19S,20R-epoxy Docosapentaenoic Acid
Molecular Formula
C22H32O3
Formula Weight
344.5
Purity
≥90%
Formulation (Request formulation change)
A solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: Soluble
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

    $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

    19S(20R)-EpDPA is an oxylipin and a metabolite of docosahexaenoic acid (DHA; Item No. 90310).1,2 It is formed from DHA by various cytochrome P450 (CYP) isoforms in a stereoselective manner.2 Unlike 19R(20S)-EpDPA (Item No. 28628), 19S(20R)-EpDPA does not prevent calcium-induced increases in the spontaneous beating of isolated neonatal rat cardiomyocytes (NRCMs).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cinelli, M.A., Yang, J., Scharmen, A., et al. Enzymatic synthesis and chemical inversion provide both enantiomers of bioactive epoxydocosapentaenoic acids. J. Lipid Res. 59(11), 2237-2252 (2018).

    2. 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).

    3. Burke, J.E., and Dennis, E.A. Phospholipase A2 structure/function, mechanism, and signaling. J. Lipid Res. 50(Suppl), S237-S242 (2009).