Linoleoyl ethanolamide

Base Information

• Chemical Name: Linoleoyl ethanolamide
• CAS No.: 68171-52-8
• Molecular Formula: C20H37 N O2
• Molecular Weight: 323.519
• European Community (EC) Number: 269-029-6
• UNII: 889DYX0816
• DSSTox Substance ID: DTXSID10887223
• Wikidata: Q27132980
• Pharos Ligand ID: 6NUBP7G29HSA
• Metabolomics Workbench ID: 4651
• ChEMBL ID: CHEMBL149859
• Mol file: 68171-52-8.mol

Synonyms:linoleoyl ethanolamide;linoleoylethanolamide

Chemical Property of Linoleoyl ethanolamide

Chemical Property:

• Appearance/Colour: ethanol solution
• Vapor Pressure: 4.73E-12mmHg at 25°C
• Melting Point: 38-40 °C
• Boiling Point: 499.1 ºC at 760 mmHg
• PKA: 14.49±0.10(Predicted)
• Flash Point: 255.6 ºC
• PSA: 49.33000
• Density: 0.926 g/cm³
• LogP: 5.29930
• Storage Temp.: −20°C
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 323.282429423
• Heavy Atom Count: 23
• Complexity: 311

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Linoleoylethanolamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): FXi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CCC=CCCCCCCCC(=O)NCCO
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO
• Uses: N-Linoleoylethanolamine reduces lipopolysaccharide-induced inflammation in macrophages and reduces inflammation in ameliorates 2,4-dinitrofluorobenzene-induced contact dermatitis. N-Linoleoylethanolamine inhibits NF-κB signaling and may be used as a therapeutic agent against contact dermatitis.Linoleoyl ethanolamide is an endocannabinoid detected in porcine brain.

Technology Process of Linoleoyl ethanolamide

There total 6 articles about Linoleoyl ethanolamide 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: 96.0%

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) + ethanolamine (141-43-5) → N-linoleoylethanolamine (68171-52-8)

Guidance literature:

linoleic 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: 90.0%

linoleyl chloride (7459-33-8) + ethanolamine (141-43-5) → N-linoleoylethanolamine (68171-52-8)

Guidance literature:

With pyridine;

DOI:10.1016/0040-4039(96)01802-3

Reference yield: 70.3%

cis-Octadecenoic acid (112-80-1,2027-47-6) + linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) + ethanolamine (141-43-5) → N-oleoylethanolamine (7545-20-2,111-58-0) + N-linoleoylethanolamine (68171-52-8)

Guidance literature:

With sodium methylate; In ethanol; hexane; for 3h; Solvent; Concentration; Time;

DOI:10.1007/s11746-015-2749-6

upstream raw materials:

linoleyl chloride

ethanolamine

linoleic acid

linoleic acid imidazolide

Refernces

• 1、 Tinto, Francesco,Archambault, Anne-Sophie,Dumais, élizabeth,Rakotoarivelo, Volatiana,Kostrzewa, Magdalena,Martin, Cyril,Plante, Pier-Luc,Desjardins, Yves,Simard, Mélissa,Pouliot, Roxane,De Petrocellis, Luciano,Ligresti, Alessia,Di Marzo, Vincenzo,Flamand, Nicolas. "Synthesis and molecular targets of N-13-hydroxy-octadienoyl-ethanolamine, a novel endogenous bioactive 15-lipoxygenase-derived metabolite of N-linoleoyl-ethanolamine found in the skin and saliva". . . Retrieved 2021.
• 2、 Wang, Xiaosan,Han, Zhengyang,Chen, Yang,Jin, Qingzhe,Wang, Xingguo. "Scalable synthesis of oleoyl ethanolamide by chemical amidation in a mixed solvent". . p. 125 - 131. Retrieved 2016/01/12.