1873-59-2

Basic information

• Product Name: 2-hydroxy-3-methyl-4-quinolone
• Synonyms: 2-hydroxy-3-methyl-1H-quinolin-4-one;2-hydroxy-3-methyl-4-quinolone;2(1H)-Quinolinone, 4-hydroxy-3-Methyl-;4-Hydroxy-3-methylquinolin-2(1H)-one;3-Methyl-2,4-quinolinediol
• CAS NO: 1873-59-2
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18396
• Mol File: 1873-59-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 309.153 °C at 760 mmHg
• Flash Point: 140.771 °C
• Appearance: /
• Density: 1.297 g/cm³
• Vapor Pressure: 0.000281mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-hydroxy-3-methyl-4-quinolone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-3-methyl-4-quinolone(1873-59-2)
• EPA Substance Registry System: 2-hydroxy-3-methyl-4-quinolone(1873-59-2)

Safety Data

• Hazardous Substances Data: 1873-59-2(Hazardous Substances Data)

Usage

General Description

2-hydroxy-3-methyl-4-quinolone is a chemical compound with a heterocyclic structure consisting of a quinolone ring with a hydroxyl group at the 2 position and a methyl group at the 3 position. It is a derivative of quinolone, which is a class of organic compounds with a bicyclic structure. This particular compound has been studied for its potential pharmaceutical properties, including its antibacterial and antifungal activities. It has also been investigated for its potential use as a chelating agent in metal complexation and as an antioxidant. Due to its unique structure and potential biological activities, 2-hydroxy-3-methyl-4-quinolone is of interest in the fields of medicinal chemistry and pharmaceutical research.

InChI:InChI=1/C10H9NO2/c1-6-9(12)7-4-2-3-5-8(7)11-10(6)13/h2-5H,1H3,(H2,11,12,13)

Upstream product

• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 1264-45-5 (2RS)-methylmalonyl-CoA 
• 15601-92-0 2-methyl-3-oxo-3-(phenylamino)propanoic acid 
• 6833-01-8 Methylmalonsaeure-dianilid 
• 62-53-3 aniline 
• 52629-26-2 ethyl 2-(N-phenylcarbamoyl)propanoate 
• 67-56-1 methanol 
• 773837-37-9 sodium cyanide 
• 144603-20-3 3-chloro-3-methylquinoline-2,4(1H,3H)-dione 
• 609-08-5 Diethyl methylmalonate 
• 1399323-75-1 1,2,3,4-tetrahydro-3-methyl-2,4-dioxoquinolin-3-yl thiocyanate 
• 529-89-5 4-hydroxy-3-formyl-1H-quinolin-2-one 
• 87-25-2 2-ethoxycarbonylaniline 
• 862255-44-5 2-carboethoxyanilide monoethyl ester of methylmalonic acid 

Downstream Products

• 14469-11-5 2-[(2-oxopropanoyl)amino]benzoic acid 
• 873399-47-4 (4-chloro-3-methyl-[2]quinolyl)-(4-chloro-phenyl)-amine 
• 523-64-8 flindersine 
• 56857-97-7 2,4-dichloro-3-methyl-quinoline 

Relevant articles and documents

Synthesis of intervenolin, an antitumor natural quinolone with unusual substituents

Synthesis of intervenolin, a natural quinolone discovered by screening for selective growth inhibitors of cancer cells cocultured with stromal cells over monocultured cells, was achieved. The synthesis utilized a thiocyanate- isothiocyanate rearrangement and Suzuki-Miyaura coupling to furnish the characteristic substituents, the iminodithiocarbonate moiety, and the geranyl side chain, respectively. In vivo studies showed that intervenolin inhibited tumor tissue growth in model mice.

One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline

3-Unsubstituted 4-hydroxy-2(1H)-quinolone (DHQ) derivatives were synthesized from aniline derivatives and diethyl malonate at low temperature using AlCl3 as catalyst and Eaton reagent as acidic environment. A reaction mechanism was proposed and elucidated. Different synthetic intermediates are specially prepared or purified and used to understand the reaction and validation mechanism.

4-Hydroxy-3-methyl-2(1h)-quinolone, originally discovered from a brassicaceae plant, produced by a soil bacterium of the genus burkholderia sp.: Determination of a preferred tautomer and antioxidant activity

4-Hydroxy-3-methyl-2(1H)-quinolone (1), a molecule known for a long time and recently discovered from a Brassicaceae plant Isatis tinctoria without providing sufficient evidence to support the structure, was isolated from a fermentation extract of Burkholderia sp. 3Y-MMP isolated from a soil by a Zn2+ enrichment culture. Detailed spectroscopic analyses by MS and NMR, combined with 13C chemical shift comparison with literature values of the related compounds and a synthetic preparation of 1, allowed its first full NMR characterization and identification of 2-quinolone but not 2-quinolinol (2) as the preferred tautomer for this heterocyclic system. While the metal-chelating activity was negligible, compound 1 at 10 μM, a concentration lower than that in liquid production cultures, quenched hydroxy radical-induced chemiluminescence emitted by luminol by 86percent. Because some Burkholderia species are pathogenic to plants and animals, the above result suggests that 1 is a potential antioxidant to counteract reactive oxygen species-based immune response in the host organisms.

Oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones into N-(α-ketoacyl)anthranilic acids Dedicated to Professor Slovenko Polanc on his 65th birthday

N-(α-Ketoacyl)anthranilic acids were prepared by oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones by using paraperiodic acid (H5IO6) or sodium periodate (NaIO4). The optimisation of the reaction conditions is