SML0384

Eicosapentaenoyl ethanolamide

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

• Synonym(e): (5Z,8Z,11Z,14Z,17Z)-N-(2-Hydroxyethyl)-5,8,11,14,17-eicosapentaenamide, EPEA
• Empirische Formel (Hill-System): C₂₂H₃₅NO₂
• CAS-Nummer: 109001-03-8
• Molekulargewicht: 345.52
• MDL-Nummer: MFCD22416528
• UNSPSC-Code: 51111800
• PubChem Substanz-ID: 329825384
• NACRES: NA.77

Eigenschaften

• Qualitätsniveau: 100
• Assay: ≥98% (HPLC)
• Form: solution
• Arzneimittelkontrolle: regulated under CDSA - not available from Sigma-Aldrich Canada
• Lagerbedingungen: protect from light; under inert gas
• Konzentration: 5 mg/mL in absolute ethanol
• Farbe: light yellow
• Lagertemp.: −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-
• InChIKey: OVKKNJPJQKTXIT-JLNKQSITSA-N

Beschreibung

Biochem./physiol. Wirkung

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.

Sonstige Hinweise

Light and air sensitive; store in a freezer.

Sicherheitshinweise

• Lagerklassenschlüssel: 10 - Combustible liquids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable