5-Carboxy-8-hydroxyquinoline

Base Information

• Chemical Name: 5-Carboxy-8-hydroxyquinoline
• CAS No.: 5852-78-8
• Molecular Formula: C10H7NO3
• Molecular Weight: 189.17
• Hs Code.: 2933499090
• Mol file: 5852-78-8.mol

Synonyms:8XQ;8-Hydroxy-chinolin-5-carbonsaeure;8-hydroxy-quinoline-5-carboxylic acid;UNII-JM015YQC1C;5-Carboxy-8-hydroxyquinoline;IOX1;8-Hydroxy-5-quinolinecarboxylic acid;

Chemical Property of 5-Carboxy-8-hydroxyquinoline

Chemical Property:

• Melting Point: 301 °C (decomp)
• Boiling Point: 464.5±30.0 °C(Predicted)
• PKA: 1.82±0.10(Predicted)
• PSA: 70.42000
• Density: 1.480±0.06 g/cm3(Predicted)
• LogP: 1.63860
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble10mg/mL, clear

Purity/Quality:

97% ^*data from raw suppliers

IOX 1 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Description: IOX 1 (5852-78-8) inhibits the JMJD family of 2-oxoglutarate-dependent histone demethylases. IC50 = 0.12, 0.07, 0.2, 0.3, 0.6, and 1 μM for JMJD3, JMJD1A, JMJD2A, JMJD2E, JMJD2C and UTX respectively.1?A broad spectrum 2-oxoglutarate oxygenase inhibitor, IOX 1 may be used to study hypoxic signaling.1?Cell permeable
• Uses: 5-Carboxy-8-hydroxyquinoline is an inhibitor of KDM2/7 histone demethylase. 5-Carboxy-8-hydroxyquinoline has also shown potential to be used as a regulator of plant growth. 8-Hydroxyquinoline-5-carboxylic Acid is an inhibitor of KDM2/7 histone demethylase. 8-Hydroxyquinoline-5-carboxylic acid has also shown potential to be used as a regulator of plant growth. IOX1 has been used:To eliminate viral latency in latent viruses in order to sensitize the viral infections to antiviral therapy.In histone lysine demethylase 4A (KDM4A) inhibition, to serve as a unique strategy to decrease hypoxia-inducible factors signalling.to restore oncogene-induced senescence in wild-type mouse embryo fibroblasts.

Technology Process of 5-Carboxy-8-hydroxyquinoline

There total 12 articles about 5-Carboxy-8-hydroxyquinoline 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: 52.0%

3-amino-4-hydroxybenzoic acid (1571-72-8) → 8-hydroxy-quinoline-5-carboxylic acid (5852-78-8)

Guidance literature:

With hydrogenchloride; acrolein; In water; at 100 ℃; for 2.5h; Reflux;

DOI:10.1002/cmdc.201300428

Reference yield: 49.0%

acrolein (107-02-8,25068-14-8) + 3-amino-4-hydroxybenzoic acid (1571-72-8) → 8-hydroxy-quinoline-5-carboxylic acid (5852-78-8)

Guidance literature:

With hydrogenchloride; In water; at 100 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jm301544x

Reference yield:

8-quinolinol (148-24-3,24804-14-6) → 8-hydroxy-quinoline-5-carboxylic acid (5852-78-8)

Guidance literature:

With tetrachloromethane; potassium hydroxide;

upstream raw materials:

8-quinolinol

8-hydroxyquinoline-5-carbonitrile

8-hydroxy-quinoline-5-carboxylic acid anilide

8-hydroxy-quinoline-5-carboxylic acid ethylamide

Downstream raw materials:

8-quinolinol

quinoline-8-methoxy-5-carboxylic acid

8-Ethoxy-chinolin-5-carbonsaeure

ethyl 8-hydroxyquinoline-5-carboxylate

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.

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