Avenanthramide C

Base Information

• Chemical Name: Avenanthramide C
• CAS No.: 116764-15-9
• Molecular Formula: C16H13NO6
• Molecular Weight: 315.282
• European Community (EC) Number: 806-389-0
• UNII: 5FRF61BOYU
• DSSTox Substance ID: DTXSID60151507
• Metabolomics Workbench ID: 48252
• Nikkaji Number: J1.233.877E,J1.868.466G
• Wikidata: Q27262004
• Mol file: 116764-15-9.mol

Synonyms:avenanthramide;avenanthramide 2C;avenanthramide-2C;avenanthramide-c;N-(3',4'-dihydroxycinnamoyl)-5-hydroxyanthranilic acid

Chemical Property of Avenanthramide C

Chemical Property:

• Melting Point: 248-250°C (dec.)
• Boiling Point: 702.3±60.0 °C(Predicted)
• PKA: 3.37±0.36(Predicted)
• PSA: 130.58000
• Density: 1.582±0.06 g/cm3(Predicted)
• LogP: 2.80300
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly, Heated)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 315.07428713
• Heavy Atom Count: 23
• Complexity: 466

Purity/Quality:

NLT 98% ^*data from raw suppliers

Avenanthramide C ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 3624543
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)NC2=C(C=C(C=C2)O)C(=O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1/C=C/C(=O)NC2=C(C=C(C=C2)O)C(=O)O)O)O
• Recent ClinicalTrials: Single and Multiple Ascending Oral Doses of Avenanthramide
• Uses: Avenanthramide C is an antioxidant and an anti-inflammatory agent. Avenanthramide reduces and attenuates proliferation of colonic cancer cells. Avenanthramide C inhibits chymotrypsin activity and moderately trypsin activity.

Technology Process of Avenanthramide C

There total 8 articles about Avenanthramide C 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: 61.0%

5-hydroxy-2-(2-carboxyacetyl)aminobenzoic acid + 3,4-dihydroxybenzaldehyde (139-85-5) → (E)-5-hydroxy-2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (116764-15-9)

Guidance literature:

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

Reference yield:

C20H17NO8 → (E)-5-hydroxy-2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (116764-15-9)

Guidance literature:

With pyrrolidine; In dichloromethane; for 1h;

DOI:10.1016/j.abb.2021.108857

Reference yield:

3,4-diacetoxybenzaldehyde (67727-64-4) + 2-amino-5-hydroxybenzoic acid (394-31-0) + acetic anhydride (108-24-7) → (E)-5-hydroxy-2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (116764-15-9)

Guidance literature:

2-amino-5-hydroxybenzoic acid; acetic anhydride; Heating;

3,4-diacetoxybenzaldehyde; With toluene-4-sulfonic acid; In toluene; Heating;

With sodium phosphate; Heating;

DOI:10.1021/jf020544f

upstream raw materials:

2-[(E)-2-(3,4-Dihydroxy-phenyl)-vinyl]-6-hydroxy-benzo[d][1,3]oxazin-4-one

caffeic acid

2-amino-5-hydroxybenzoic acid

3,4-diacetoxybenzaldehyde

Refernces

• 1、 -. "Synthetic method of oat alkaloids". Paragraph 0029. . Retrieved 2018/09/14.
• 2、 Bratt, Katarina,Sunnerheim, Kerstin,Bryngelsson, Susanne,Fagerlund, Amelie,Engman, Lars,Andersson, Rolf E.,Dimberg, Lena H.. "Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships". . p. 594 - 600. Retrieved 2007/10/03.