Arachidonoyl Serinol

Base Information

• Chemical Name: Arachidonoyl Serinol
• CAS No.: 183718-70-9
• Molecular Formula: C₂₃H₃₉NO₃
• Molecular Weight: 377.568
• DSSTox Substance ID: DTXSID90694013
• Mol file: 183718-70-9.mol

Synonyms:Arachidonoyl Serinol;N-(1,3-dihydroxypropan-2-yl)icosa-5,8,11,14-tetraenamide;DTXSID90694013;CHEBI:183751

Chemical Property of Arachidonoyl Serinol

Chemical Property:

• Boiling Point: 569.9±50.0 °C(Predicted)
• PKA: 13.97±0.10(Predicted)
• PSA: 72.55000
• Density: 0.983±0.06 g/cm3(Predicted)
• LogP: 5.69520
• Solubility.: ≤10mg/ml in ethanol;10mg/ml in DMSO;10mg/ml in dimethyl formamide
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 17
• Exact Mass: 377.29299411
• Heavy Atom Count: 27
• Complexity: 449

Purity/Quality:

≥98% ^*data from raw suppliers

Arachidonoyl Serinol ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CO)CO

Technology Process of Arachidonoyl Serinol

There total 2 articles about Arachidonoyl Serinol 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: 89.0%

arachidonoyl chloride (57303-04-5) + serinol (534-03-2) → N-arachidonoyl serinol (183718-70-9)

Guidance literature:

With triethylamine; In methanol; at -20 - 20 ℃;

DOI:10.3390/molecules23071513

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → N-arachidonoyl serinol (183718-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2, DMF / benzene / 1 h / 0 - 5 °C

2: pyridine / CH₂Cl₂ / 0.25 h / Ambient temperature

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; benzene;

DOI:10.1021/jm960152y

Reference yield: 36.0%

3,4,5-tris(2-(tert-butoxycarbonylamino)ethoxy)benzoic acid (1208000-64-9) + N-arachidonoyl serinol (183718-70-9) → bis-O-[3,4,5-tris(2-N-boc-amino-1-ethoxy)benzoyl]-N-arachidonoyl serinol

Guidance literature:

3,4,5-tris(2-(tert-butoxycarbonylamino)ethoxy)benzoic acid; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 0.25h;

N-arachidonoyl serinol; In dichloromethane; N,N-dimethyl-formamide; at 30 ℃; for 24h;

DOI:10.3390/molecules23071513

upstream raw materials:

arachidonoyl chloride

serinol

all cis 5,8,11,14-eicosatetraenoic acid

Refernces

• 1、 Khanolkar, Atmaram D.,Abadji, Vasiliki,Lin, Sonyuan,Hill, W. Adam G.,Taha, Gihan,Abouzid, Khaled,Meng, Zhaoxing,Fan, Pusheng,Makriyannis, Alexandros. "Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand". . p. 4515 - 4519. Retrieved 2007/10/03.