N-(p-Amylcinnamoyl)anthranilic acid

Base Information

• Chemical Name: N-(p-Amylcinnamoyl)anthranilic acid
• CAS No.: 110683-10-8
• Molecular Formula: C21H23 N O3
• Molecular Weight: 337.419
• Hs Code.: 2924299090
• European Community (EC) Number: 662-753-7
• UNII: LCJ9M6AJ5F
• DSSTox Substance ID: DTXSID401166445
• Nikkaji Number: J829.752E
• Wikipedia: N-(p-Amylcinnamoyl)anthranilic_acid
• Wikidata: Q6951332
• Pharos Ligand ID: NPLP5QHGPJW5
• ChEMBL ID: CHEMBL173443
• Mol file: 110683-10-8.mol

Synonyms:4-ACAA;4-amylcinnamoylanthranilic acid;N-(p-amylcinnamoyl)anthranilic acid;p-amylcinnamoylanthranilic acid

Chemical Property of N-(p-Amylcinnamoyl)anthranilic acid

Chemical Property:

• Vapor Pressure: 1.61E-13mmHg at 25°C
• Melting Point: 172-174℃
• Boiling Point: 563.1°C at 760 mmHg
• PKA: 3.49±0.36(Predicted)
• Flash Point: 294.4°C
• PSA: 66.40000
• Density: 1.178g/cm³
• LogP: 4.84240
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 337.16779360
• Heavy Atom Count: 25
• Complexity: 452

Purity/Quality:

99%min ^*data from raw suppliers

N-(p-Amylcinnamoyl)anthranilic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC1=CC=C(C=C1)C=CC(=O)NC2=CC=CC=C2C(=O)O
• Isomeric SMILES: CCCCCC1=CC=C(C=C1)/C=C/C(=O)NC2=CC=CC=C2C(=O)O
• Uses: N-(p-amylcinnamoyl) Anthranilic acid (ACA) is a channel blocker that acts on several transient receptor potential (TRP) channels, including TRPM2, TRPM8, and TRPC6 (IC50 = 1.7, 3.8, and 2.3 μM, respectively). It is a weak inhibitor of TRPV1. ACA is also an inhibitor of phospholipase A2, blocking the release of arachidonic acid when given at 50 μM.

Technology Process of N-(p-Amylcinnamoyl)anthranilic acid

There total 4 articles about N-(p-Amylcinnamoyl)anthranilic acid 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:

4-pentylbenzaldehyde (6853-57-2) → ACA (110683-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: piperidine / pyridine / 4 h / 120 °C

2: 1.) oxalyl chloride, 2.) pyridine / 1.) room temperature, 30 min, 2.) CH₂Cl₂, ice-bath, 1 h; room temperature, 2 h

With piperidine; pyridine; oxalyl dichloride; In pyridine;

DOI:10.1021/jm00396a013

Reference yield:

trans-4-n-pentylcinnamic acid-N-(2-methoxycarbonyl-phenyl)-amide (99197-00-9) → ACA (110683-10-8)

Guidance literature:

With sodium hydroxide; In methanol;

Reference yield:

pentylbenzene (538-68-1) → ACA (110683-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / 80 °C

2: piperidine / pyridine / 4 h / 120 °C

3: 1.) oxalyl chloride, 2.) pyridine / 1.) room temperature, 30 min, 2.) CH₂Cl₂, ice-bath, 1 h; room temperature, 2 h

With piperidine; pyridine; oxalyl dichloride; In pyridine; trifluoroacetic acid;

DOI:10.1021/jm00396a013

upstream raw materials:

trans-β-(n-amyl)acrylic acid

anthranilic acid

4-pentylbenzaldehyde

pentylbenzene

Refernces

• 1、 Nakai,Konno,Kosuge,Sakuyama,Toda,Arai,Obata,Katsube,Miyamoto,Okegawa,Kawasaki. "New potent antagonists of leukotrienes C4 and D4. 1. Synthesis and structure-activity relationships". . p. 84 - 91. Retrieved 2007/10/02.