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:

98%,99%, ^*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
• General Description: Xanthurenic acid (XA) is a metabolite produced by the enzymatic action of 3-hydroxykynurenine transaminase (HKT) on 3-hydroxykynurenine, playing a significant role in mosquito physiology, particularly in Anopheles gambiae. It serves as a key intermediate in the kynurenine pathway and has been identified as a potential target for transmission-blocking strategies against malaria, as inhibiting its production could disrupt mosquito vector function. The development of assays to measure HKT activity and screen for inhibitors highlights its relevance in insecticide and drug discovery efforts.

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:

4,8-dihydroxyquinoline

N-<(4',8'-dihydroxy-2'-quinolyl)carbonyl>-(R)-glutamic acid di-n-pentylamide γ-benzyl ester

toluene-4-sulfonic acid 4-oxo-1,4-dihydro-quinolin-8-yl ester

4-methoxyquinolin-8-yl 4-methylbenzenesulfonate

Refernces

Study of Anopheles gambiae 3-hydroxykynurenine transaminase activity and inhibition by LC-MS/MS method

10.1016/j.jpba.2019.05.025

The study focuses on the activity and inhibition of Anopheles gambiae 3-hydroxykynurenine transaminase (Ag-HKT), an enzyme that metabolizes 3-hydroxykynurenine into xanthurenic acid, which is crucial for mosquito vector physiology and a potential target for transmission-blocking drugs and insecticides. The researchers developed and validated a new LC-MS/MS method to evaluate Ag-HKT activity and the potency of inhibitors. Chemicals used in the study included L-kynurenine (L-KYN), kynurenic acid (KA), xanthurenic acid (XA), 3-hydroxy-DL-kynurenine (D,L-3-HK), and pyridoxal 5′-phosphate (PLP) as key components of the enzymatic assay. Additionally, 4-(2-aminophenyl)-4-oxobutanoic acid (INI) and its derivative 4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid (3-OH-INI) were synthesized and tested as potential inhibitors of Ag-HKT. The purpose of these chemicals was to establish a method for quantifying the enzyme's activity and to identify and characterize compounds that could inhibit Ag-HKT, providing a basis for the development of new insecticides and malaria transmission-blocking drugs.