| Identification | Back Directory | [Name]
STEAROYL ETHANOLAMIDE | [CAS]
111-57-9 | [Synonyms]
SEA
AM-1105
CERAMID
STEARAMIDE MEA
STEAROYL ETHANOLAMIDE
N-Stearoylethanolamide
Stearyl monoethanolamide
stearic monoethanolamide
STEARIC ACID ETHANOLAMIDE
Stearoylethanolamide(SEA)
Stearinsuremonoethanolamid
N-(octadecanoyl)ethanolamine
N-(2-hydroxyethyl)stearamide
STEARIC ACID MONOETHANOLAMIDE
n-(2-hydroxyethyl)-octadecanamid
Octadecanamide, N-(2-hydroxyethyl)-
Stearic acid-ethanolamine condensate
N-(2-Hydroxyethyl)stearic acid amide
Stearic acid monoethanolamide Tech. Grade | [EINECS(EC#)]
203-883-2 | [Molecular Formula]
C20H41NO2 | [MDL Number]
MFCD00045971 | [MOL File]
111-57-9.mol | [Molecular Weight]
327.55 |
| Chemical Properties | Back Directory | [Melting point ]
103-104 °C(Solv: ethanol (64-17-5)) | [Boiling point ]
486.0±28.0 °C(Predicted) | [density ]
0.904±0.06 g/cm3(Predicted) | [vapor pressure ]
0Pa at 20℃ | [storage temp. ]
−20°C
| [solubility ]
DMF: >2 mg/ml; DMSO: >100 μg/ml; Ethanol: >2 mg/ml; PBS pH 7.2: >100 μg/ml | [form ]
crystalline
| [pka]
14.49±0.10(Predicted) | [color ]
White to light yellow | [Water Solubility ]
1mg/L at 20℃ | [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]
4.46 at 20℃ | [EPA Substance Registry System]
N-(2-Hydroxyethyl)octadecanamide (111-57-9) |
| Hazard Information | Back Directory | [Uses]
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. | [Definition]
ChEBI: An N-(long-chain-acyl)ethanolamine that is the ethanolamide of octadecanoic acid. | [Preparation]
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.
 | [Flammability and Explosibility]
Nonflammable |
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