(E)-2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid

Base Information

• Chemical Name: (E)-2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid
• CAS No.: 122520-79-0
• Molecular Formula: C10H7NO4
• Molecular Weight: 205.17
• Nikkaji Number: J2.033.333B,J377.772C
• ChEMBL ID: CHEMBL73820
• Mol file: 122520-79-0.mol

Synonyms:AG 30;AG-30

Chemical Property of (E)-2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid

Chemical Property:

• Vapor Pressure: 1.8E-09mmHg at 25°C
• Melting Point: 240 °C
• Refractive Index: 1.717
• Boiling Point: 465.6 °C at 760 mmHg
• PKA: 0.81±0.10(Predicted)
• Flash Point: 235.4 °C
• PSA: 101.55000
• Density: 1.559 g/cm³
• LogP: 1.08938
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 205.03750770
• Heavy Atom Count: 15
• Complexity: 328

Purity/Quality:

98%Min ^*data from raw suppliers

TyrphostinAG30 98.60% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=C(C#N)C(=O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1/C=C(\C#N)/C(=O)O)O)O

Technology Process of (E)-2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid

There total 6 articles about (E)-2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic 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: 94.0%

cyanoacetic acid (372-09-8) + 3,4-dihydroxybenzaldehyde (139-85-5) → AG 30 (122520-79-0)

Guidance literature:

With piperidine; In N,N-dimethyl-formamide; at 90 ℃; for 0.5h; Microwave irradiation;

DOI:10.1016/j.bioorg.2022.105624

Reference yield: 90.0%

(E)-tert-butyl-2-cyano-3-(3,4-dihydroxyphenyl)acrylate → AG 30 (122520-79-0)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 1h;

DOI:10.1016/j.ejmech.2014.01.049

Reference yield: 71.0%

ethyl α-cyano-β-(3,4-dihydroxyphenyl)acrylate (132464-92-7) → AG 30 (122520-79-0)

Guidance literature:

With sodium hydroxide; for 0.166667h; Ambient temperature;

DOI:10.1002/jps.2600800503

upstream raw materials:

ethyl α-cyano-β-(3,4-dihydroxyphenyl)acrylate

cyanoacetic acid

3,4-dihydroxybenzaldehyde

Refernces

• 1、 -. "Cinnamic acid derivative with aldose reductase inhibitory activity as well as preparation method and application thereof". Paragraph 0076; 0079. . Retrieved 2017/09/01.
• 2、 Rodrigues, Nuno,Bennis, Khalil,Vivier, Delphine,Pereira, Vanessa,Chatelain, Franck C.,Chapuy, Eric,Deokar, Hemantkumar,Busserolles, Jér?me,Lesage, Florian,Eschalier, Alain,Ducki, Sylvie. "Synthesis and structure-activity relationship study of substituted caffeate esters as antinociceptive agents modulating the TREK-1 channel". supporting information. p. 391 - 402. Retrieved 2014/03/21.