N-(2-Hydroxyethyl)octadecanamide

Base Information

• Chemical Name: N-(2-Hydroxyethyl)octadecanamide
• CAS No.: 111-57-9
• Deprecated CAS: 8038-89-9
• Molecular Formula: C20H41NO2
• Molecular Weight: 327.551
• Hs Code.: 2924199090
• European Community (EC) Number: 203-883-2
• NSC Number: 52619,3377
• UNII: 03XV449Q24
• DSSTox Substance ID: DTXSID9042178
• Nikkaji Number: J115.317J
• Wikipedia: Stearoylethanolamide
• Wikidata: Q15427850
• Metabolomics Workbench ID: 4695
• ChEMBL ID: CHEMBL171447
• Mol file: 111-57-9.mol

Synonyms:N-(2-hydroxyethyl)stearoylamide;stearoylethanolamide

Chemical Property of N-(2-Hydroxyethyl)octadecanamide

Chemical Property:

• Vapor Pressure: 1.74E-11mmHg at 25°C
• Melting Point: 103-104 °C(Solv: ethanol (64-17-5))
• Refractive Index: 1.463
• Boiling Point: 486.034 °C at 760 mmHg
• PKA: 14.49±0.10(Predicted)
• Flash Point: 247.744 °C
• PSA: 49.33000
• Density: 0.905 g/cm³
• LogP: 5.74730
• Storage Temp.: −20°C
• Water Solubility.: 1mg/L at 20℃
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 18
• Exact Mass: 327.313729551
• Heavy Atom Count: 23
• Complexity: 244

Purity/Quality:

99.9% ^*data from raw suppliers

Stearoyl ethanolamide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)NCCO
• 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.

Technology Process of N-(2-Hydroxyethyl)octadecanamide

There total 13 articles about N-(2-Hydroxyethyl)octadecanamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

ethanolamine (141-43-5) + Stearoyl chloride (112-76-5) → N-stearoylethanolamine (111-57-9,8038-89-9)

Guidance literature:

In dichloromethane; for 1h;

DOI:10.1080/14756366.2021.1912035

Reference yield: 96.0%

ethanolamine (141-43-5) + stearic acid (57-11-4) → N-stearoylethanolamine (111-57-9,8038-89-9)

Guidance literature:

stearic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 0.5h;

ethanolamine; In dichloromethane; for 12h;

DOI:10.1055/s-0037-1611939

Reference yield: 95.4%

vinyl stearate (111-63-7,9003-95-6) + ethanolamine (141-43-5) → N-stearoylethanolamine (111-57-9,8038-89-9)

Guidance literature:

With sodium methylate; at 80 ℃; for 1h; Neat (no solvent);

DOI:10.1007/s11746-012-2017-y

upstream raw materials:

O-stearoylethanolamine

stearic acid ethyl ester

ethanolamine

stearic acid

Downstream raw materials:

2-heptadecyl-2-imidazoline

O-stearoylethanolamine

N-dodecanoylglycine

N-myristoylglycine

Refernces

• 1、 Ottria, Roberta,Casati, Silvana,Ciuffreda, Pierangela. "Optimized synthesis and characterization of N-acylethanolamines and O-acylethanolamines, important family of lipid-signalling molecules". . p. 705 - 711. Retrieved 2012.
• 2、 M?ki-Arvela, P?ivi,Zhu, Jeanne,Kumar, Narendra,Er?nen, Kari,Aho, Atte,Linden, Johan,Salonen, Jarno,Peurla, Markus,Mazur, Anton,Matveev, Vladimir,Murzin, Dmitry Yu.. "Solvent-free “green” amidation of stearic acid for synthesis of biologically active alkylamides over iron supported heterogeneous catalysts". . p. 350 - 358. Retrieved 2017.
• 3、 Kajita, Daisuke,Nakamura, Masaharu,Matsumoto, Yotaro,Ishikawa, Minoru,Hashimoto, Yuichi,Fujii, Shinya. "Design and synthesis of silicon-containing fatty acid amide derivatives as novel peroxisome proliferator-activated receptor (PPAR) agonists". . p. 3350 - 3354. Retrieved 2015.
• 4、 Jiang, Shaoliang,Gao, Jianrong,Han, Liang. "Synthesis and biological activity of N-acyl O-indolylalkyl ethanolamines". . p. 768 - 770. Retrieved 2011.
• 5、 Ghidini, Andrea,Scalvini, Laura,Palese, Francesca,Lodola, Alessio,Mor, Marco,Piomelli, Daniele. "Different roles for the acyl chain and the amine leaving group in the substrate selectivity of N-Acylethanolamine acid amidase". . p. 1411 - 1423. Retrieved 2021/07/17.
• 6、 Johansson, Silje J. R.,Johannessen, Tonje,Ellefsen, Christiane F.,Ristun, Mali S.,Antonsen, Simen,Hansen, Trond V.,Stenstrom, Yngve,Nolsoe, Jens M. J.. "A Convenient Protocol for the Synthesis of Fatty Acid Amides". supporting information. p. 213 - 217. Retrieved 2019/01/14.