(5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide

Base Information

• Chemical Name: (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide
• CAS No.: 183718-77-6
• Deprecated CAS: 198022-70-7
• Molecular Formula: C₂₆H₃₇NO₂
• Molecular Weight: 395.585
• UNII: XVJ94H0U21
• DSSTox Substance ID: DTXSID60424985
• Nikkaji Number: J790.918G
• Wikipedia: AM404
• Wikidata: Q4652517
• Pharos Ligand ID: L1R4HC7Q8WMG
• ChEMBL ID: CHEMBL39878
• Mol file: 183718-77-6.mol

Synonyms:5,8,11,14-eicosatetraenamide, N-(4-hydroxyphenyl)-, (5Z,8Z,11Z,14Z)-;5,8,11,14-eicosatetraenamide, N-(4-hydroxyphenyl)-, (all-Z)-;AM 404;AM-404;AM404;N-(4-hydroxyphenyl)-eicosa-5,8,11,14-tetraenamide;N-(4-hydroxyphenyl)arachidonylamide

Chemical Property of (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide

Chemical Property:

• Vapor Pressure: 5.02E-14mmHg at 25°C
• Refractive Index: 1.555
• Boiling Point: 579.4 °C at 760 mmHg
• Flash Point: 304.2 °C
• PSA: 49.33000
• Density: 1.007 g/cm³
• LogP: 7.54940
• Storage Temp.: −20°C
• Solubility.: ethanol: 24 mg/mL Photosensitive solution.
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 395.282429423
• Heavy Atom Count: 29
• Complexity: 511

Purity/Quality:

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

AM 404 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 36/37/38-11
• Safety Statements: 7-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC1=CC=C(C=C1)O
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC1=CC=C(C=C1)O
• Uses: It is a metabolite of the well-known analgesic Paracetamol. ase (FAAH) in vivo. Potentiates the activity of endogenous anandamide by blocking its re-uptake into presynaptic membranes. AM404 selectively inhibits the carrier-mediated transport of anandamide without affecting anandamide hydrolysis.

Technology Process of (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide

There total 4 articles about (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide 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: 61.0%

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) + 4-amino-phenol (123-30-8) → AM 404 (183718-77-6)

Guidance literature:

all cis 5,8,11,14-eicosatetraenoic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 0.5h;

4-amino-phenol; In dichloromethane; for 12h;

DOI:10.1055/s-0037-1611939

Reference yield:

C23H36O4 + 4-amino-phenol (123-30-8) → AM 404 (183718-77-6)

Guidance literature:

In water; acetonitrile; at 0 ℃; for 24h;

DOI:10.1055/s-0037-1611893

Reference yield:

4-amino-phenol (123-30-8) + arachidonoyl chloride (57303-04-5) → AM 404 (183718-77-6)

Guidance literature:

In tetrahydrofuran; benzene; for 0.25h; Yield given; Ambient temperature;

DOI:10.1021/jm960152y

upstream raw materials:

4-amino-phenol

arachidonoyl chloride

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

Refernces

• 1、 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.
• 2、 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.