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

Base Information

• Chemical Name: N-(4-nitrophenyl)icosa-5,8,11,14-tetraenamide
• CAS No.: 119520-58-0
• Molecular Formula: C26H36N2O3
• Molecular Weight: 424.583
• DSSTox Substance ID: DTXSID80693999
• Mol file: 119520-58-0.mol

Synonyms:DTXSID80693999;N-(4-nitrophenyl)icosa-5,8,11,14-tetraenamide

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

Chemical Property:

• PSA: 74.92000
• LogP: 8.27520
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 424.27259301
• Heavy Atom Count: 31
• Complexity: 594

Purity/Quality:

98%Min ^*data from raw suppliers

Arachidonoylp-Nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC1=CC=C(C=C1)[N+](=O)[O-]
• Description: Arachidonoyl p-nitroaniline (ApNA) is one of several nitroaniline fatty acid amides which can be used to measure fatty acid amide hydrolase (FAAH) activity. FAAH is a relatively unselective enzyme in that it accepts a variety of amide head groups other than the ethanolamine of its nominal endogenous substrate anandamide (AEA; ). It also will hydrolyze fatty acid amides with fewer carbons and fewer double bonds than arachidonate. (See also Decanoyl p-Nitroaniline - Catalog No. 90349). Exposure of ApNA to FAAH activity results in the release of the yellow colorimetric dye p-nitroaniline (ε = 13,500 at 382 nm). This offers the potential for fast and convenient measurements of FAAH activity using a 96-well plate spectrophotometer.
• Uses: Arachidonoyl p-Nitroaniline is a nitroaniline probe for FAAH activity.

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

There total 4 articles about N-(4-nitrophenyl)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: 35.0%

p-nitrophenyl isocyanide (1984-23-2) + (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid 2-thioxo-2H-pyridin-1-yl ester → 2-[((4Z,7Z,10Z,13Z)-Nonadeca-4,7,10,13-tetraenyl)sulfanyl]-pyridine (119541-44-5) + N-(p-nitrophenyl)-arachidonamide (119520-58-0)

Guidance literature:

In benzene; at 40 ℃; for 1h; Mechanism; Irradiation; ⁽¹³⁾C-labelling study;

DOI:10.1016/S0040-4020(01)85980-9

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → N-(p-nitrophenyl)-arachidonamide (119520-58-0)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride, DMF / benzene / Ambient temperature

2: tetrahydrofuran

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

DOI:10.1016/S0040-4020(01)85980-9

Reference yield:

(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid isobutyl ester (119520-63-7) → N-(p-nitrophenyl)-arachidonamide (119520-58-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 3 N aq. NaOH / ethanol / 12 h / Ambient temperature

2: oxalyl chloride, DMF / benzene / Ambient temperature

3: tetrahydrofuran

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

DOI:10.1016/S0040-4020(01)85980-9

upstream raw materials:

p-nitrophenyl isocyanide

4-nitro-aniline

arachidonoyl chloride

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

Downstream raw materials:

arachidonoyl chloride

cis-4,7,10,13-nonadecatetraenylphenylselenide

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

Refernces