Xanthurenic acid

Base Information

• Chemical Name: Xanthurenic acid
• CAS No.: 59-00-7
• Molecular Formula: C10H7 N O4
• Molecular Weight: 205.17
• Hs Code.: 29334900
• European Community (EC) Number: 200-410-1
• NSC Number: 401570
• UNII: 58LAB1BG8J
• DSSTox Substance ID: DTXSID90207728
• Nikkaji Number: J8.600B
• Wikipedia: Xanthurenic_acid
• Wikidata: Q5961262
• Metabolomics Workbench ID: 37483
• ChEMBL ID: CHEMBL312535
• Mol file: 59-00-7.mol

Synonyms:8-hydroxykynurenic acid;gametocyte activating factor (GAF);xanthurenic acid

Chemical Property of Xanthurenic acid

Chemical Property:

• Appearance/Colour: ochre powder
• Vapor Pressure: 1.08E-07mmHg at 25°C
• Melting Point: 297-298 ºC
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 416.8°Cat760mmHg
• PKA: 1.20±0.30(Predicted)
• Flash Point: 205.8°C
• PSA: 90.65000
• Density: 1.569g/cm³
• LogP: 1.34420
• Storage Temp.: Store at RT
• Solubility.: DMSO (Slightly, Heated), Water (Slightly, Heated)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 205.03750770
• Heavy Atom Count: 15
• Complexity: 336

Purity/Quality:

99.5% ^*data from raw suppliers

Xanthurenic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)O)NC(=CC2=O)C(=O)O
• Uses: Excreted by pyridoxine-deficient animals after the ingestion of tryptophan. caspase activator, guanylyl cyclase stimulant Xanthurenic acid can be used as a substrate for the synthesis of: Silica-gel functionalized xanthurenic acid (4, 8-dihydroxyquinoline-2-carboxylic acid) as an adsorbent for metal ions.N, N′-bis-((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ethers as fluorescent sensors of magnesium in living cells via one-pot Mannich reaction.Poly-xanthurenic acid (poly-Xa) for biosensing applications.

Technology Process of Xanthurenic acid

There total 10 articles about Xanthurenic 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: 85.0%

methyl 4-hydroxy-8-methoxyquinoline-2-carboxylate (4008-46-2) → xanthurenic acid (59-00-7)

Guidance literature:

methyl 4-hydroxy-8-methoxyquinoline-2-carboxylate; With hydrogen bromide; In water; at 120 ℃; for 72h; Sealed tube; Inert atmosphere; Schlenk technique;

With sodium hydroxide; In water; pH=Ca.2.5;

DOI:10.1039/c8cy00158h

Reference yield:

3-hydroxykynurenine (484-78-6,606-14-4,2147-61-7,4043-91-8) → xanthurenic acid (59-00-7) + 2'-amino-3'-hydroxyacetophenone (4502-10-7)

Guidance literature:

With barium dihydroxide;

Reference yield:

8-methoxy-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid ethyl ester (55895-59-5) → xanthurenic acid (59-00-7)

Guidance literature:

With phosphoric acid; potassium iodide;

DOI:10.1021/jo01143a010 DOI:10.1515/bchm2.1954.297.1.247 DOI:10.1021/ja01151a522

upstream raw materials:

methyl 4-hydroxy-8-methoxyquinoline-2-carboxylate

8-methoxy-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid ethyl ester

3-hydroxykynurenine

4-hydroxy-2-methylquinoline

Downstream raw materials:

4-phenylquinolin-8-yl 4-methylbenzenesulfonate

4-bromoquinolin-8-yl 4-methylbenzenesulfonate

4-chloro-8-hydroxyquinoline

4-(1H-pyrazol-1-yl)quinolin-8-yl 4-methylbenzenesulfonate

Refernces

• 1、 Xiang, Wenjing,Li, Lin,Dai, Zengjin,Meng, Xianggao,Li, Renjie,Zhang, Jing,Peng, Tianyou. "TiO2 modified with a Ru(ii)-N′NN′ 8-hydroxyquinolyl complex for efficient gaseous photoreduction of CO2". . p. 2098 - 2103. Retrieved 2018/05/03.
• 2、 HEINRICH,VON HOLT. "Synthesis of xanthurenic acid.". . p. 247 - 248. Retrieved 2007/10/04.