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N-(2-Hydroxyethyl)stearamid
SEA · CERAMID · N-(2-hydroxyethyl)stearamide · STEARAMIDE MEA · STEARIC ACID MONOETHANOLAMIDE · N-Stearoylethanolamide · AM-1105 · Stearoyl ethanolamide
Identifikatoren & physikalische Daten
| CAS No. | 111-57-9 |
|---|---|
| Summenformel | C20H41NO2 |
| Durchschnittliche Molmasse | 327,5 g/mol |
| Monoisotopische Masse | 327,31372955 g/mol |
| SMILES | CCCCCCCCCCCCCCCCCC(=O)NCCO |
| InChIKey | OTGQIQQTPXJQRG-UHFFFAOYSA-N |
| PubChem CID | 27902 |
| ChEMBL | CHEMBL171447 |
| ChEBI | CHEBI:85299 |
| EC No. | 203-883-2 |
| DTXSID | DTXSID9042178 |
| Lokaler Name | N-(2-Hydroxyethyl)stearamid |
Chemische & physikalische Eigenschaften
| XLogP | 7,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 49,3 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 18 |
| Schwere Atome | 23 |
| Formalladung | 0 |
| Komplexität | 244 |
| Schmelzpunkt | 98.5 °C103-104 °C(Solv: ethanol (64-17-5)) |
| Physical Description | Large CrystalsOther SolidDry Powder |
| Kovats Retention Index | 2347.1 |
| Collision Cross Section | 198.93 Ų [M+H]+ [CCS Type: TIMSMethod: single field calibrated] |
| Siedepunkt | 486.0±28.0 °C(Predicted) |
| Dichte | 0.904±0.06 g/cm3(Predicted) |
| Dampfdruck | 0Pa at 20℃ |
| Lagerbedingungen | −20°C |
| Löslichkeit | DMF: >2 mg/mlDMSO: >100 μg/mlEthanol: >2 mg/mlPBS pH 7.2: >100 μg/ml1mg/L at 20℃ |
| Aggregatzustand | crystalline |
| pKa (Säurekonstante) | 14.49±0.10(Predicted) |
| Farbe | White to light yellow |
| Kosmetik-Inhaltsstoffe Funktionen | VISCOSITY CONTROLLINGSURFACTANT - FOAM BOOSTINGANTISTATIC |
| InChI | InChI=1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23) |
| InChIKey | OTGQIQQTPXJQRG-UHFFFAOYSA-N |
| SMILES | C(NCCO)(=O)CCCCCCCCCCCCCCCCC |
| LogP (Verteilungskoeffizient) | 4.46 at 20℃ |
| EPA chemische Informationen | N-(2-Hydroxyethyl)octadecanamide (111-57-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 4.3% (12 of 281) of reports.DangerH315 (88.3%): Causes skin irritation [Warning Skin corrosion/irritation]H318 (95.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H411 (37.4%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]H412 (50.2%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P264, P264+P265, P273, P280, P302+P352, P305+P354+P338, P317, P321, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 281 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 12 of 281 reports by companies.There are 5 notifications provided by 269 of 281 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: Octadecanamide, N-(2-hydroxyethyl)-Octadecanamide, N-(2-hydroxyethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Octadecanamide, N-(2-hydroxyethyl)- 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: 17-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14395Status: Active Update: 07-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/32501Octadecanamide, N-(2-hydroxyethyl)-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (88.3%)Eye Dam. 1 (95.7%)Aquatic Chronic 2 (37.4%)Aquatic Chronic 3 (50.2%) |
| 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...Stearamide MEASafe for use in cosmetics, with qualifications |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Sicherheitshinweise (S) | 22-24/25 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
Stearoyl Ethanolamide is a prolific fatty acid ethanolamide produced by PLD hydrolysis of membrane phospholipids. Stearoyl Ethanolamide is also used for studying the effect on endocannabinoid signalling and BBB integrity in systemic inflammation.
Herstellung & Synthese
synthetische
In the stirred state, fatty acids (1.0 mmol, 1.0 equiv) were added to CH2Cl2 (5 mL), followed by CDI (0.178 g, 1.1 mmol, 1.1 equiv). After 30 min, the amine (1.1 mmol, 1.1equiv.)was added. Added CH2Cl2 (25ml) and saturated NH4Cl aqueous solution after 12 h. HCl was added to the mixture to adjusted pH=2. After the organic phase was separated, the aqueous layer was further extracted with CH2Cl2 (3 × 10 mL). The organic phase was collected and placed on Na2SO4 to dried, and filtered. Finally, the product (STEAROYL ETHANOLAMIDE) was obtained by vacuum concentration.