SML0384

Eicosapentaenoyl ethanolamide

5 mg/mL in absolute ethanol, ≥98% (HPLC)

• Synonym(s): (5Z,8Z,11Z,14Z,17Z)-N-(2-Hydroxyethyl)-5,8,11,14,17-eicosapentaenamide, EPEA
• Empirical Formula (Hill Notation): C₂₂H₃₅NO₂
• CAS Number: 109001-03-8
• Molecular Weight: 345.52
• MDL number: MFCD22416528
• UNSPSC Code: 51111800
• PubChem Substance ID: 329825384
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: solution
• drug control: regulated under CDSA - not available from Sigma-Aldrich Canada
• storage condition: protect from light; under inert gas
• concentration: 5 mg/mL in absolute ethanol
• color: light yellow
• storage temp.: −20°C
• SMILES string: CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO
• 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

Description

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.

Other Notes

Light and air sensitive; store in a freezer.

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable