59-00-7

Basic information

• Product Name: XANTHURENIC ACID
• Synonyms: 4,8-DIHYDROXYQUINOLINE-2;4,8-DIHYDROXYQUINOLINE-2-CARBOXYLIC ACID;4,8-DIHYDROXY-2-QUINOLINECARBOXYLIC ACID;4,8-DIHYDROXYQUINALDIC ACID;2-Quinolinecarboxylic acid, 4,8-dihydroxy-;XANTHURENIC ACID(RG);4,8-DIHYDROXYQUINOLINE-2-CARBOXYLIC ACID 96%;XANTHURENIC ACID extrapure
• CAS NO: 59-00-7
• Molecular Formula: C₁₀H₇NO₄
• Molecular Weight: 205.17
• EINECS: 200-410-1
• Product Categories: Quinolines, Quinazolines and derivatives;Hydroxyquinolines;Quinolines;Amines;Aromatics;Heterocycles;Building Blocks;C8 to C10;Chemical Synthesis;Heterocyclic Building Blocks;Inhibitors
• Mol File: 59-00-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 297-298 °C (dec.)(lit.)
• Boiling Point: 343.83°C (rough estimate)
• Flash Point: 205.8°C
• Appearance: Ochre/Powder
• Density: 1.3849 (rough estimate)
• Vapor Pressure: 1.08E-07mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: Store at RT
• Solubility: DMSO (Slightly, Heated), Water (Slightly, Heated)
• PKA: 1.20±0.30(Predicted)
• Merck: 14,10068
• BRN: 185954
• CAS DataBase Reference: XANTHURENIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: XANTHURENIC ACID(59-00-7)
• EPA Substance Registry System: XANTHURENIC ACID(59-00-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: UZ9275000
• Hazardous Substances Data: 59-00-7(Hazardous Substances Data)

Usage

Chemical Properties

ochre powder

Uses

Different sources of media describe the Uses of 59-00-7 differently. You can refer to the following data:
1. Excreted by pyridoxine-deficient animals after the ingestion of tryptophan.
2. caspase activator, guanylyl cyclase stimulant
3. 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.

Definition

ChEBI: A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8.

Purification Methods

It is precipitated by the addition of 2N formic acid to its solution in hot 2M ammonia (charcoal). The solid is filtered off, dried in a vacuum at ~80o in the dark. UV (H2O) has nm ( M-1cm-1): 243 (30,000) and 342 (6,500). The methyl ester has m 262o (from MeOH). It forms Cu2+, Zn2+, Fe2+ and Fe3+ salts. [Beilstein 22 III/IV 2513.]

InChI:InChI=1/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)

Upstream product

• 5934-38-3 4,8-dihydroxy-quinoline-2-carboxylic acid methyl ester 
• 607-67-0 4-hydroxy-2-methylquinoline 
• 484-78-6 3-hydroxykynurenine 
• 55895-59-5 8-methoxy-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid ethyl ester 
• 4008-46-2 methyl 4-hydroxy-8-methoxyquinoline-2-carboxylate 
• 90-04-0 2-methoxy-phenylamine 
• 7101-82-8 dimethyl 2-((2-methoxyphenyl)amino)but-2-enedioate 

Downstream Products

• 122668-06-8 N-<(4',8'-dihydroxy-2'-quinolyl)carbonyl>-(R)-glutamic acid di-n-pentylamide γ-benzyl ester 
• 1108187-56-9 4-phenylquinolin-8-yl 4-methylbenzenesulfonate 
• 1166262-04-9 4-bromoquinolin-8-yl 4-methylbenzenesulfonate 
• 57334-36-8 4-chloro-8-hydroxyquinoline 
• 1022094-19-4 4-(1H-pyrazol-1-yl)quinolin-8-yl 4-methylbenzenesulfonate 
• 1022094-18-3 (4-chloroquinolin-8-yl)-4-methylbenzenesulfonate 
• 1360172-44-6 C₁₆H₁₂N₂O₃ 
• 21638-90-4 methyl 8-hydroxyquinoline-2-carboxylate 
• 1571-30-8 8-hydroxy-quinoline-2-carboxylic acid 
• 927833-19-0 4-octyloxy-8-tosyloxyquinoline 
• 927833-21-4 4-benzyloxy-8-tosyloxyquinoline 
• 927833-18-9 4-butoxy-8-tosyloxyquinoline 
• 927833-20-3 4-isopropyloxy-8-tosyloxyquinoline 
• 927833-17-8 4-methoxyquinolin-8-yl 4-methylbenzenesulfonate 

Relevant articles and documents

Design, synthesis, and biological evaluation of novel arylcarboxamide derivatives as anti-tubercular agents

Our group has previously reported several indolecarboxamides exhibiting potent antitubercular activity. Herein, we rationally designed several arylcarboxamides based on our previously reported homology model and the recently published crystal structure of the mycobacterial membrane protein large 3 (MmpL3). Many analogues showed considerable anti-TB activity against drug-sensitive (DS) Mycobacterium tuberculosis (M. tb) strain. Naphthamide derivatives 13c and 13d were the most active compounds in our study (MIC: 6.55, 7.11 μM, respectively), showing comparable potency to the first line anti-tuberculosis (anti-TB) drug ethambutol (MIC: 4.89 μM). In addition to the naphthamide derivatives, we also identified the quinolone-2-carboxamides and 4-arylthiazole-2-carboxamides as potential MmpL3 inhibitors in which compounds 8i and 18b had MIC values of 9.97 and 9.82 μM, respectively. All four compounds retained their high activity against multidrug-resistant (MDR) and extensively drug-resistant (XDR) M. tb strains. It is worth noting that the two most active compounds 13c and 13d also exhibited the highest selective activity towards DS, MDR and XDR M. tb strains over mammalian cells [IC50 (Vero cells) ≥ 227 μM], indicating their potential lack of cytotoxicity. The four compounds were docked into the MmpL3 active site and were studied for their drug-likeness using Lipinski's rule of five.

KYNURENIC ACID AND XANTHURENIC ACID IN HABROBRACON JUGLANDIS ASHMEAD.

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