An N-acylethanolamine signaling molecule
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Labeled Version(s)
9001835Eicosapentaenoyl Ethanolamide-d4
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Eicosapentaenoyl Ethanolamide

Item No. 10964

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-5Z,8Z,11Z,14Z,17Z-eicosapentaenamide
CAS Number
109001-03-8
Synonyms
  • EPEA
Molecular Formula
C22H35NO2
Formula Weight
345.5
Purity
≥98%
Formulation (Request formulation change)
A 50 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
SMILES
O=C(NCCO)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC
InChi Code
InChI=1S/C22H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h3-4,6-7,9-10,12-13,15-16,24H,2,5,8,11,14,17-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChi Key
OVKKNJPJQKTXIT-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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    5 mg

    $69

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    10 mg

    $127

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    50 mg

    $525

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    100 mg

    $918

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    Product Description

    Eicosapentaenoyl ethanolamide (EPEA) is an N-acylethanolamide that inhibits dietary-restriction-induced lifespan extension in wild type and TOR pathway mutant nematodes.1 Produced endogenously from eicosapentaenoic acid, EPEA serves as a metabolic signal that couples nutrient availability with growth and lifespan. 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).

    Product Citations

    Hartling, I., Cremonesi, A., Osuna, E., et al. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS. Clin. Chem. Lab. Med. 59(11), 1811-1823 (2021).