An EPA-containing MAG amide analog
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Eicosapentaenoyl 1-propanol-2-amide

Item No. 17547

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxy-1-methylethyl)-5Z,8Z,11Z,14Z,17Z-eicosapentaenamide
CAS Number
1638355-66-4
Molecular Formula
C23H37NO2
Formula Weight
359.6
Purity
≥98%
Formulation (Request formulation change)
A 10 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
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(NC(CO)C)=O
InChi Code
InChI=1S/C23H37NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(26)24-22(2)21-25/h4-5,7-8,10-11,13-14,16-17,22,25H,3,6,9,12,15,18-21H2,1-2H3,(H,24,26)/b5-4-,8-7-,11-10-,14-13-,17-16-
InChi Key
XOYVLIGJHWVUFH-JEBPEJKESA-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

    $36

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    5 mg

    $153

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    10 mg

    $268

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    25 mg

    $587

    Add
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    Product Description

    Monoacylglycerols (MAGs) of ω-3 polyunsaturated fatty acids have diverse physiological and health effects.1,2,3 In particular, MAGs containing docosahexaenoic acid (Item No. 90310) or eicosapentaenoic acid (EPA; Item No. 90110) have anti-proliferative properties against colon and lung cancer cell lines.4 Eicosapentaenoyl 1-propanol-2-amide is an EPA-containing MAG amide analog that inhibits the growth of human lung carcinoma A549 cells, producing 98.4% growth inhibition when applied at 3 µM.5 It is an analog of eicosapentaenoyl ethanolamide (Item No. 10964), a natural N-acylethanolamide that impacts aging and inflammation.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hernández-Torres, G., Cipriano, M., Hedén, E., et al. A reversible and selective inhibitor of monoacylglycerol lipase ameliorates multiple sclerosis. Angew. Chem. Int. Ed. Engl. 53(50), 13765-13770 (2014).

    2. Douglass, J.D., Zhou, Y.X., Wu, A., et al. Global deletion of MGL in mice delays lipid absorption and alters energy homeostasis and diet-induced obesity. J. Lipid Res. 56(6), 1153-1171 (2015).

    3. Morin, C., Blier, P.U., and Fortin, S. Eicosapentaenoic acid and docosapentaenoic acid monoglycerides are more potent than docosahexaenoic acid monoglyceride to resolve inflammation in a rheumatoid arthritis model. Arthritis Res. Ther. 17(1), 142 (2015).

    4. Morin, C., Rousseau, É., and Fortin, S. Anti-proliferative effects of a new docosapentaenoic acid monoacylglyceride in colorectal carcinoma cells. Prostaglandins Leukot. Essent. Fatty Acids 89(4), 203-213 (2013).

    5. Tremblay, H., St-Georges, C., Legault, M.A., et al. One-pot synthesis of polyunsaturated fatty acid amides with anti-proliferative properties. Bioorg. Med. Chem. Lett. 24(24), 5635-5638 (2014).

    6. 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).

    7. 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).