3-[(Icosa-5,8,11,14-tetraenoyl)amino]phenolate

Base Information

• Chemical Name: 3-[(Icosa-5,8,11,14-tetraenoyl)amino]phenolate
• CAS No.: 183718-75-4
• Molecular Formula: C₂₆H₃₇NO₂
• Molecular Weight: 395.585
• DSSTox Substance ID: DTXSID70703036
• Mol file: 183718-75-4.mol

Synonyms:DTXSID70703036;3-[(Icosa-5,8,11,14-tetraenoyl)amino]phenolate

Chemical Property of 3-[(Icosa-5,8,11,14-tetraenoyl)amino]phenolate

Chemical Property:

• Boiling Point: 579.4±50.0 °C(Predicted)
• PKA: 9.57±0.10(Predicted)
• PSA: 49.33000
• Density: 1.007±0.06 g/cm3(Predicted)
• LogP: 7.54940
• Solubility.: ≤20mg/ml in DMSO;20mg/ml in dimethyl formamide
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 394.274604391
• Heavy Atom Count: 29
• Complexity: 519

Purity/Quality:

97% ^*data from raw suppliers

N-(3-Hydroxyphenyl)-ArachidonoylAmide ^*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)NC1=CC(=CC=C1)[O-]
• Description: N-(3-hydroxyphenyl)-Arachidonoyl amide (3-HPA) is an analog of AM404 (N-(4-hydroxyphenyl)-arachidonoyl amide), which is a selective inhibitor of carrier-mediated transport of arachidonoyl ethanolamide (AEA). 3-HPA is metabolized by both cyclooxygenase-1 (COX-1) and COX-2 and was found to selectively and irreversibly inhibit COX-2 with an IC50 value of 2 μM.
• Uses: N-(3-hydroxyphenyl)-Arachidonoyl amide is a selective, irreversible inhibitor of COX-2.

Technology Process of 3-[(Icosa-5,8,11,14-tetraenoyl)amino]phenolate

There total 2 articles about 3-[(Icosa-5,8,11,14-tetraenoyl)amino]phenolate 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:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (3-hydroxy-phenyl)-amide (183718-75-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: benzene; tetrahydrofuran / 0.25 h / Ambient temperature

With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; benzene;

DOI:10.1021/jm960152y

Reference yield:

arachidonoyl chloride (57303-04-5) + m-Hydroxyaniline (591-27-5) → (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (3-hydroxy-phenyl)-amide (183718-75-4)

Guidance literature:

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

DOI:10.1021/jm960152y

upstream raw materials:

arachidonoyl chloride

m-Hydroxyaniline

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

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