Synonym: (5Z,8Z,11Z,14Z,17Z)-N-(2-Hydroxyethyl)-5,8,11,14,17-eicosapentaenamide; EPEA
CAS Number: 109001-03-8
Empirical Formula (Hill Notation): C22H35NO2
Molecular Weight: 345.52
MDL Number: MFCD22416528
Linear Formula: C22H35NO2
Product Type: Chemical
| assay |
≥98% (HPLC) |
| color |
light yellow |
| concentration |
5 mg/mL in absolute ethanol |
| drug control |
regulated under CDSA - not available from Sigma-Aldrich Canada |
| form |
solution |
| 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 |
| Quality Level |
100  |
| SMILES string |
CCC=C/CC=C/CC=C/CC=C/CC=C/CCCC(=O)NCCO |
| storage condition |
protect from light |
| |
under inert gas |
| storage temp. |
−20°C |
| Biochem/physiol Actions: |
Eicosapentaenoyl ethanolamide (EPEA) is a lipid mediator that 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. elegans, it is believed to act as a metabolic signal that couples nutrient availability with growth and lifespan. EPEA is a member of the N-acylethanolamines (NAEs), lipid-derived signaling molecules that include the mammalian endocannabinoid arachidonoyl ethanolamide (AEA). In mammals, NAEs are believed to act primarily through cannabinoid receptors, although they can also interact with a variety of other targets, and EPEA has been shown to act as a CB1 and CB2 receptor agonist. However, C. elegans does not possess clear orthologues of the mammalian cannabinoid receptors which suggests that there are unidentified NAE receptors in nematodes that are possibly conserved mediators of NAE signaling. |
| Biochem/physiol Actions: |
Eicosapentaenoyl ethanolamide (EPEA) is a lipid mediator; suppresses lifespan extension; anti proliferative and anti-inflammatory. |
| Other Notes: |
Light and air sensitive; store in a freezer. |
| Packaging: |
5, 25 mg in glass bottle |
| RIDADR |
NONH for all modes of transport |
| WGK Germany |
WGK 3 |
| Flash Point(F) |
Not applicable |
| Flash Point(C) |
Not applicable |
| Purity |
≥98% (HPLC) |
| Storage Temp. |
−20°C |
| UNSPSC |
51111800 |
