3-Hydroxyanthranilic acid

Base Information

• Chemical Name: 3-Hydroxyanthranilic acid
• CAS No.: 548-93-6
• Molecular Formula: C7H7 N O3
• Molecular Weight: 153.137
• Hs Code.: 2922509090
• European Community (EC) Number: 208-962-5
• NSC Number: 522891
• UNII: 1UQB1BT4OT
• DSSTox Substance ID: DTXSID40203290
• Nikkaji Number: J1.608J
• Wikipedia: 3-Hydroxyanthranilic_acid
• Wikidata: Q2823213
• Metabolomics Workbench ID: 37817
• ChEMBL ID: CHEMBL445304
• Mol file: 548-93-6.mol

Synonyms:3 Hydroxyanthranilic Acid;3-Hydroxyanthranilic Acid;Acid, 3-Hydroxyanthranilic

Chemical Property of 3-Hydroxyanthranilic acid

Chemical Property:

• Vapor Pressure: 1.83E-19mmHg at 25°C
• Melting Point: 240 °C (dec.)(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 356.8°Cat760mmHg
• PKA: pK1: 2.5(+1);pK2: 5.192(0);pK3: 10.118(OH) (25°C)
• Flash Point: 169.6°C
• PSA: 83.55000
• Density: 1.491g/cm³
• LogP: 1.25380
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 153.042593085
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

98% ^*data from raw suppliers

3-Hydroxyanthranilic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-40
• Safety Statements: 22-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)O)N)C(=O)O
• Uses: 3-Hydroxyanthranilic Acid is one of the tryptophan’s metabolites along the kynurenine pathway. 3-Hydroxyanthranilic Acid has been shown to induce apoptosis in T cells.

Technology Process of 3-Hydroxyanthranilic acid

There total 20 articles about 3-Hydroxyanthranilic 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: 86.0%

2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-6-methoxyaniline (63478-14-8) → 3-hydroxyanthranilic acid (548-93-6)

Guidance literature:

With phosphorus; hydrogen iodide; at 100 ℃; for 14h;

DOI:10.1016/S0040-4039(00)85411-8

Reference yield: 36.0%

cinnabarinic acid (606-59-7) → (4R,4aS)-2-Amino-4,4a-dihydroxy-3-oxo-10-oxy-4,4a-dihydro-3H-phenoxazine-1,9-dicarboxylic acid (141861-80-5,141861-81-6) + (4S,4aS)-2-Amino-4,4a-dihydroxy-3-oxo-10-oxy-4,4a-dihydro-3H-phenoxazine-1,9-dicarboxylic acid (141861-80-5,141861-81-6) + 3-hydroxyanthranilic acid (548-93-6)

Guidance literature:

With dihydrogen peroxide; for 12h; Title compound not separated from byproducts; pH 7;

Reference yield:

3-methoxy-2-nitrobenzoic acid (4920-80-3) → 3-hydroxyanthranilic acid (548-93-6)

Guidance literature:

With phosphorus; hydrogen iodide;

upstream raw materials:

2-amino-3-methoxybenzoic acid

3-methoxy-2-nitrobenzoic acid

3-hydroxy-2-nitrobenzoic acid

3-methoxy-2-methylamino-benzoic acid

Downstream raw materials:

Sodium; 2-amino-3,6-dioxo-5-phenethylamino-cyclohexa-1,4-dienecarboxylate

methyl 6H,9H,7-amino 2,3-dihydro-6,9-dioxo benzo 1H-azepine-8-carboxylate

(Z)-3-benzylidene-3,4-dihydro-2-oxo-2H-1,4-benzoxazine-5-carboxylic acid

3,5'-diacetoxy-6'-diacetylamino-2,3'-imino-di-benzoic acid

Refernces

• 1、 Bahar, M. H.,Shringarpure, J. D.,Kulkarni, G. H.,Sabata, B. K.. "STRUCTURE AND SYNTHESIS OF ATALAPHYLLINE AND RELATED ALKALOIDS". . p. 2729 - 2732. Retrieved 1982.
• 2、 Fitzgerald, Deirdre H.,Muirhead, Karen M.,Botting, Nigel P.. "A comparative study on the inhibition of human and bacterial kynureninase by novel bicyclic kynurenine analogues". . p. 983 - 989. Retrieved 2007/10/03.