N-(2-Hydroxyethyl)oleamid
ODA · OLEOYL ETHANOLAMIDE · OEA · N-(2-Hydroxyethyl)oleamide · N-Oleoylethanolamine · Oleoylethanolamide(OEA) · OLEAMIDE MEA · N-(Hydroxyethyl)oleamide
Identifikatoren & physikalische Daten
| CAS No. | 111-58-0 |
|---|---|
| Summenformel | C20H39NO2 |
| Durchschnittliche Molmasse | 325,5 g/mol |
| Monoisotopische Masse | 325,29807949 g/mol |
| SMILES | CCCCCCCC/C=C\CCCCCCCC(=O)NCCO |
| InChIKey | BOWVQLFMWHZBEF-KTKRTIGZSA-N |
| PubChem CID | 5283454 |
| ChEMBL | CHEMBL280065 |
| ChEBI | CHEBI:71466 |
| EC No. | 203-884-8 |
| DTXSID | DTXSID1044516 |
| Lokaler Name | N-(2-Hydroxyethyl)oleamid |
Chemische & physikalische Eigenschaften
| XLogP | 6,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 49,3 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 17 |
| Schwere Atome | 23 |
| Formalladung | 0 |
| Komplexität | 277 |
| Lipide | Fatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl ethanolamines (endocannabinoids) [FA0804] |
| Kosmetika | Cosmetic ingredients (Oleamide MEA) -> CIR (Cosmetic Ingredient Review)Personal care productAntistaticViscosity controllingFoam boosting |
| Physical Description | Other Solid |
| Collision Cross Section | 192.94 Ų [M+H]+ [CCS Type: TIMSMethod: single field calibrated] |
| Schmelzpunkt | 63-64 °C |
| Siedepunkt | 496.4±38.0 °C(Predicted) |
| Dichte | 0.915±0.06 g/cm3(Predicted) |
| Lagerbedingungen | -20°C |
| Löslichkeit | Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 35 mg/ml) |
| Aggregatzustand | White solid |
| pKa (Säurekonstante) | 14.49±0.10(Predicted) |
| Farbe | White |
| Stabilität | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. |
| Kosmetik-Inhaltsstoffe Funktionen | VISCOSITY CONTROLLINGANTISTATICSURFACTANT - FOAM BOOSTING |
| InChI | InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9- |
| InChIKey | BOWVQLFMWHZBEF-KTKRTIGZSA-N |
| SMILES | C(NCCO)(=O)CCCCCCC/C=C\CCCCCCCC |
| LogP (Verteilungskoeffizient) | 6.406 (est) |
| CAS Datenbank | 111-58-0(CAS DataBase Reference) |
| EPA chemische Informationen | 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- (111-58-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 205 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 9-Octadecenamide, N-(2-hydroxyethyl)-, (Z)-9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 11-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/197159-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Toxizitätsübersicht | The CIR Expert Panel concluded that the ethanolamides listed subsequently are safe in the present practices of use and concentration described in this safety assessment when formulated to be non-irritating. The Expert Panel cautioned that these ingredients should not be used in cosmetic products in which N-nitroso compounds may be formed...Oleamide MEA...Safe for use in cosmetics, with qualifications |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | IRRITANT |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Oleoyl ethanolamide (OEA) is an analog of the endocannabinoid AEA found in brain tissue and in chocolate. It is one of the long chain fatty acid ethanolamides that accumulates rapidly in infarcted tissue, but its biosynthesis is reduced in the intestine of rats following food deprivation. OEA is an endogenous, potent agonist for PPARα, exhibiting an EC50 value of 120 nM in a transactivation assay. Systemic administration of OEA suppresses food intake and reduces weight gain in rats (10 mg/kg intraperitoneally) and PPARα wild-type mice, but not in PPARα knockout mice. These data indicate that OEA regulates food intake by a PPARα-mediated mechanism.
Verwenden
N-Oleoyl Ethanolamide is an agonist of peroxisome proliferator-activated receptor-α (PPAR-α). N-Oleoyl Ethanolamide generates an intestinal signal that stimulates central dopamine activity establishing a link between caloric-homeostatic and hedonic-homeostatic controllers. Oleoyl Ethanolamide has been implicated as the molecular mechanism associated with gastric bypass success. N-Oleoyl Ethanolamide is a selective GPR55 agonist.