15462-45-0

Basic information

• Product Name: 3-HYDROXYQUINOLINE-2-CARBOXYLIC ACID
• Synonyms: 3-HYDROXYQUINOLINE-2-CARBOXYLIC ACID
• CAS NO: 15462-45-0
• Molecular Formula: C₁₀H₇NO₃
• Molecular Weight: 189.16748
• Mol File: 15462-45-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 187-190 °C (decomp)
• Boiling Point: 384.7 °C at 760 mmHg
• Flash Point: 186.5 °C
• Appearance: /
• Density: 1.48 g/cm³
• Vapor Pressure: 1.32E-06mmHg at 25°C
• Refractive Index: 1.73
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• PKA: 0.02±0.30(Predicted)
• CAS DataBase Reference: 3-HYDROXYQUINOLINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYQUINOLINE-2-CARBOXYLIC ACID(15462-45-0)
• EPA Substance Registry System: 3-HYDROXYQUINOLINE-2-CARBOXYLIC ACID(15462-45-0)

Safety Data

• Hazardous Substances Data: 15462-45-0(Hazardous Substances Data)

Usage

Description

3-Hydroxyquinoline-2-carboxylic Acid is an organic compound with the molecular formula C10H6NO4. It is a derivative of quinoline, featuring a hydroxyl group and a carboxylic acid group. 3-HYDROXYQUINOLINE-2-CARBOXYLIC ACID is known for its potential applications in various fields due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
3-Hydroxyquinoline-2-carboxylic Acid is used as an intermediate in the chromophore biosynthesis of quinomycin family antibiotics. These antibiotics are known for their potent antimicrobial and antitumor activities, making them valuable in the development of new drugs to combat resistant infections and cancer.
Used in Chemical Synthesis:
3-Hydroxyquinoline-2-carboxylic Acid is also utilized in the total synthesis of Echinomycin and its analogs. Echinomycin is a potent antitumor agent that has shown significant promise in the treatment of various types of cancer. The synthesis of these compounds is crucial for the development of novel therapeutic agents to improve patient outcomes and address the growing need for effective cancer treatments.

Synthesis Reference(s)

Tetrahedron, 61, p. 1407, 2005 DOI: 10.1016/j.tet.2004.12.011

InChI:InChI=1/C10H7NO3/c12-8-5-6-3-1-2-4-7(6)11-9(8)10(13)14/h1-5,12H,(H,13,14)

Upstream product

• 14370-68-4 ethyl 3-hydroxyquinoline-2-carboxylate 
• 62235-59-0 ethyl 3-amino-2-quinolinecarboxylate 
• 552-89-6 2-nitro-benzaldehyde 
• 2922-83-0 L-kynurenine 
• 33925-79-0 3-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylic acid 
• 110429-24-8 3-(benzyloxy)quinoline-2-carboxylic acid 
• 529-23-7 o-aminobenzaldehyde 
• 177202-79-8 3-(methoxymethoxy)quinoline 
• 580-18-7 3-hydroxyquinoline 
• 847547-93-7 3-(methoxymethoxy)-2-methylquinoline 
• 124-38-9 carbon dioxide 
• 171917-54-7 Methyl 3-(benzyloxy)quinoline-2-carboxylate 

Downstream Products

• 100940-65-6 sandramycin 

Relevant articles and documents

Synthesis and Antiproliferative Activity Evaluation of the Disulfide-Containing Cyclic Peptide Thiochondrilline C and Derivatives

Thiochondrilline C (4) was previously isolated from Verrucisispora sp. and reported to have moderate cytotoxicity against human lung adenocarcinoma cells. Herein, we report the synthesis of thiochondrilline C by N-terminal peptide extension, oxidative disulfide bond formation, and heterocycle installation as key steps. Antiproliferative activities for the prepared natural product and several derivatives against the NCI 60 cancer cell line panel are also described. Derivative 22 was identified as a moderately potent antiproliferative agent (50% growth inhibition (GI50) = 0.2-12.2 μM) with leukemia (average GI50 = 1.8 ± 0.1 μM) and colon (average GI50 = 2.4 ± 0.3 μM) cells being most sensitive.

A new approach to 3-hydroxyquinoline-2-carboxylic acid

Quinoline-2-carboxylic acid derivatives cap the N-terminal of several natural cyclic peptides with antitumoral activity. A new and convenient route for the preparation of 3-hydroxyquinoline-2-carboxylic acid is discussed. The preparation of the title compound is accomplished by a four-step procedure from 3-hydroxyquinoline via MOM protection of the hydroxyl group, followed by a 1,2-addition of methyllithium to the quinoline ring with concomitant oxidation, and, finally, a two-step oxidation procedure for the transformation of the methyl group to the carboxylic acid along with removal of the MOM group. Furthermore, different attempts to its preparation led to other interesting quinolines, such as 2-chloro-3-hydroxyquinoline-4-carboxylic acid and a protected 3,3′-dihydroxy-2,2′-biquinoline.