8-Hydroxyquinoline-2-carboxylic acid

Base Information

• Chemical Name: 8-Hydroxyquinoline-2-carboxylic acid
• CAS No.: 1571-30-8
• Molecular Formula: C10H7 N O3
• Molecular Weight: 189.17
• Hs Code.: 2933499090
• European Community (EC) Number: 626-995-7
• UNII: EBM66FCM33
• DSSTox Substance ID: DTXSID00166211
• Nikkaji Number: J36.504A
• Wikidata: Q27188565
• ChEMBL ID: CHEMBL1368601
• Mol file: 1571-30-8.mol

Synonyms:8-hydroxyquinaldic acid

Chemical Property of 8-Hydroxyquinoline-2-carboxylic acid

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 4.83E-08mmHg at 25°C
• Melting Point: 213-214℃
• Refractive Index: 1.5400 (estimate)
• Boiling Point: 426.7oC at 760 mmHg
• PKA: 1.32±0.30(Predicted)
• Flash Point: 211.9oC
• PSA: 70.42000
• Density: 1.3175 (rough estimate)
• LogP: 1.63860
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 189.042593085
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

97% ^*data from raw suppliers

8-Hydroxyquinoline-2-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)O)N=C(C=C2)C(=O)O
• Uses: 8-Hydroxy-2-quinolinecarboxylic acid may be used in the preparation of bis (8-hydroxyquinoline-2-carboxylato-Κ3N,O,O′) cobalt (II) trihydrate.

Technology Process of 8-Hydroxyquinoline-2-carboxylic acid

There total 19 articles about 8-Hydroxyquinoline-2-carboxylic 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: 100.0%

8-hydroxyquinoline-2-carbonitrile (6759-78-0) → 8-hydroxy-quinoline-2-carboxylic acid (1571-30-8)

Guidance literature:

With water; sodium hydroxide; for 6h; Reflux;

DOI:10.1002/adsc.201801185

Reference yield: 96.0%

2-formyl oxine (14510-06-6) → 8-hydroxy-quinoline-2-carboxylic acid (1571-30-8)

Guidance literature:

With formic acid; dihydrogen peroxide; at 20 ℃; for 8h;

DOI:10.1016/j.saa.2019.117678

Reference yield: 54.0%

2-methyl-8-quinolinol (826-81-3) → 8-hydroxy-quinoline-2-carboxylic acid (1571-30-8)

Guidance literature:

With selenium(IV) oxide; In pyridine; at 90 ℃; for 16h;

DOI:10.1016/j.molstruc.2012.08.009

upstream raw materials:

8-methoxyquinoline-2-carboxylic acid

4-Chlor-8-hydroxychinaldinsaeure

5-bromo-8-methoxy-quinoline-2-carboxylic acid

8-hydroxyquinoline-2-carbonitrile

Downstream raw materials:

methyl 8-hydroxyquinoline-2-carboxylate

rac-2-(benzyloxycarbonyl-amino)-3-[(8-trifluoromethanesulfonyloxy-quinoline-2-carbonyl)amino]propionic acid methyl ester

8-hydroxy-quinoline-2-carboxylic acid benzyl ester

C₁₇H₁₃ClN₂O₂

Refernces

Positional isomers of mannose-quinoline conjugates and their copper complexes: Exploring the biological activity

10.1039/c8nj00993g

This study aimed to develop novel 8-hydroxyquinoline (HQ) derivatives with improved pharmacological properties. Three positional isomers of mannose-HQ conjugates (ManHQ2, ManHQ5, and ManHQ7) ??and one glucose-HQ conjugate (GlcHQ7) were synthesized to explore the effects of sugar type and position on biological activity. ManHQ2 was synthesized using 8-hydroxyquinoline-2-carboxylic acid (HQ2) as the starting material. ManHQ5 was synthesized using 8-hydroxyquinoline-5-carboxylic acid (HQ5) as the starting material. ManHQ7 and GlcHQ7 were synthesized using 8-hydroxyquinoline-7-carboxylic acid (HQ7) as the starting material. 8-Hydroxyquinoline-2-carboxamide (CAHQ2) was used as a reference compound for antimicrobial activity testing. These compounds were characterized by nuclear magnetic resonance spectroscopy, electrospray ionization mass spectrometry (ESI-MS), and UV-visible spectroscopy. The study found that these conjugates exhibited significant antioxidant and antibacterial activities, with specific isomers showing significant antibacterial effects against Pseudomonas aeruginosa and Staphylococcus aureus. In addition, ManHQ2 exhibited antiproliferative activity against human tumor cells in the presence of copper (II) ions. The results suggest that these HQ mannose conjugates have the potential to be bioactive molecules and have increased biocompatibility, which can be further explored for their use as antibiotics and cancer treatments.