Precursor for eicosapentaenoyl ethanolamide
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Glycerophospho-N-Eicosapentaenoyl Ethanolamine

Item No. 90001842

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3-dihydroxypropyl (2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)ethyl) hydrogen phosphate
Synonyms
  • GP-NEPEA
Molecular Formula
C25H42NO7P
Formula Weight
499.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
209 nm
SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCOP(O)(OCC(O)CO)=O)=O
InChi Code
InChI=1S/C25H42NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(29)26-20-21-32-34(30,31)33-23-24(28)22-27/h3-4,6-7,9-10,12-13,15-16,24,27-28H,2,5,8,11,14,17-23H2,1H3,(H,26,29)(H,30,31)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChi Key
ADEMPYKRVUNSKG-JLNKQSITSA-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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    1 mg

    $93

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    5 mg

    $406

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    10 mg

    $717

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    Product Description

    Glycerophospho-N-eicosapentaenoyl ethanolamine is the metabolic precursor of eicosapentaenoyl ethanolamide (EPEA; Item No. 10964). EPEA is an NAE that inhibits dietary-restriction-induced lifespan extension in wild type and TOR pathway mutant nematodes.1 EPEA also has anti-inflammatory properties, suppressing the expression of IL-6 and MCP-1 in 3T3-L1 adipocytes in response to lipopolysaccharide.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lucanic, M., Held, J.M., Vantipalli, M.C., et al. N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans. Nature 473(7346), 226-229 (2011).

    2. Balvers, M.G., Verhoeckx, K.C., Plastina, P., et al. Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties. Biochim. Biophys. Acta 1801(10), 1107-1114 (2010).