Avenanthramide B

Base Information

• Chemical Name: Avenanthramide B
• CAS No.: 108605-69-2
• Molecular Formula: C17H15 N O6
• Molecular Weight: 329.309
• European Community (EC) Number: 806-392-7
• UNII: F8BQ5730IL
• DSSTox Substance ID: DTXSID50148603
• Nikkaji Number: J704.945E,J940.002H
• Wikidata: Q27277808
• Metabolomics Workbench ID: 48251
• Mol file: 108605-69-2.mol

Synonyms:5-Hydroxy-2-(((2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoyl)amino)benzoic acid;avenanthramide 2f;avenanthramide B;Benzoic acid, 5-hydroxy-2-(((2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl)amino)-;N-(4'-hydroxy-3'-methoxy-(E)-cinnamoyl)-5-hydroxyanthranilic acid;N-feruloyl-5-hydroxyanthranilic acid

Chemical Property of Avenanthramide B

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 329.08993720
• Heavy Atom Count: 24
• Complexity: 480

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)NC2=C(C=C(C=C2)O)C(=O)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)NC2=C(C=C(C=C2)O)C(=O)O)O

Technology Process of Avenanthramide B

There total 6 articles about Avenanthramide B 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: 92.3%

C19H17NO7 → (E)-5-hydroxy-2-[[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (108605-69-2)

Guidance literature:

With sodium hydroxide; for 0.5h; pH=4.5;

Reference yield: 68.0%

5-hydroxy-2-(2-carboxyacetyl)aminobenzoic acid + vanillin (121-33-5,8014-42-4) → (E)-5-hydroxy-2-[[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (108605-69-2)

Guidance literature:

With pyridine; 3-amino propanoic acid; at 90 ℃; for 24h;

Reference yield:

2-amino-5-hydroxybenzoic acid (394-31-0) → (E)-5-hydroxy-2-[[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (108605-69-2)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 4 h / Reflux

2: pyridine; 3-amino propanoic acid / 1.83 h / 115 °C

With pyridine; 3-amino propanoic acid; In toluene;

DOI:10.1021/acs.jafc.6b04995

upstream raw materials:

vanillin acetate

2-amino-5-hydroxybenzoic acid

acetic anhydride

vanillin