| Identification | Back Directory | [Name]
Eicosapentaenoyl Ethanolamide | [CAS]
109001-03-8 | [Synonyms]
EPEA
Eicosapentaenoyl Ethanolamide
5(Z),8(Z),11(Z),14(Z),17(Z)-Eicosapentaenoyl Ethanolamide
N-(2-hydroxyethyl)-5(Z),8(Z),11(Z),14(Z),17(Z)-eicosapentaenamide
(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide
(5Z,8Z,11Z,14Z,17Z)-N-(2-Hydroxyethyl)-5,8,11,14,17-eicosapentaenamide
5,8,11,14,17-Eicosapentaenamide, N-(2-hydroxyethyl)-, (5Z,8Z,11Z,14Z,17Z)- | [Molecular Formula]
C22H35NO2 | [MDL Number]
MFCD22416528 | [MOL File]
109001-03-8.mol | [Molecular Weight]
345.52 |
| Chemical Properties | Back Directory | [Boiling point ]
522.5±50.0 °C(Predicted) | [density ]
0.951±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS (pH 7.2)(1:2): 0.3 mg/ml | [form ]
oil | [pka]
14.48±0.10(Predicted) | [color ]
colorless to yellow |
| Hazard Information | Back Directory | [Uses]
Eicosapentaenoyl Ethanolamide inhibits dietary-restriction-induced lifespan extension in wild type and TOR pathway mutant nematodes. | [Definition]
ChEBI: (5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine is an N-acylethanolamine 20:5 that is the ethanolamide of (5Z,8Z,11Z,14Z17Z)-eicosapentaenoic acid. It has a role as a PPARgamma agonist. It is an endocannabinoid and a N-acylethanolamine 20:5. It is functionally related to an all-cis-5,8,11,14,17-icosapentaenoic acid. | [Biological Activity]
Eicosapentaenoyl ethanolamide (EPEA) is a lipid mediator th at has been found to suppress lifespan extension resulting from dietary restriction in C. elegans and also to have antiproliferative and anti-inflammatory actions. In C. elegansit is believed to act as a metabolic signal th at couples nutrient availability with growth and lifespan. EPEA is a member of the N-acylethanolamines (NAEs)lipid-derived signaling molecules th at include the mammalian endocannabinoid arachidonoyl ethanolamide (AEA). In mammalsNAEs are believed to act primarily through cannabinoid receptorsalthough they can also interact with a variety of other targetsand EPEA has been shown to act as a CB1 and CB2 receptor agonist. HoweverC. elegans does not possess clear orthologues of the mammalian cannabinoid receptors which suggests th at there are unidentified NAE receptors in nematodes th at are possibly conserved mediators of NAE signaling. | [IC 50]
CB1; CB2 |
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