100717-76-8

Basic information

• Product Name: 3-butyl-2-hydroxy-1-methylquinolin-4(1H)-one
• CAS NO: 100717-76-8
• Molecular Formula: C₁₄H₁₇NO₂
• Molecular Weight: 231.2903
• Mol File: 100717-76-8.mol

Chemical Properties

• Boiling Point: 346.5°C at 760 mmHg
• Flash Point: 163.3°C
• Density: 1.152g/cm³
• Vapor Pressure: 2.18E-05mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: 3-butyl-2-hydroxy-1-methylquinolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-butyl-2-hydroxy-1-methylquinolin-4(1H)-one(100717-76-8)
• EPA Substance Registry System: 3-butyl-2-hydroxy-1-methylquinolin-4(1H)-one(100717-76-8)

Safety Data

• Hazardous Substances Data: 100717-76-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
3-butyl-2-hydroxy-1-methylquinolin-4(1H)-one is used as a therapeutic agent for treating diseases related to mitochondrial dysfunction, such as cardiovascular disease and neurodegenerative disorders. Its antioxidant properties help protect cells from oxidative stress and prevent damage caused by free radicals, making it a promising candidate for improving mitochondrial function and overall health.
Used in Cosmetic Formulations:
In the cosmetic industry, 3-butyl-2-hydroxy-1-methylquinolin-4(1H)-one is used as an antioxidant and anti-aging ingredient. Its ability to neutralize free radicals and protect cells from oxidative damage contributes to its potential in reducing the signs of aging and promoting skin health.
Used in Nutraceutical Applications:
3-butyl-2-hydroxy-1-methylquinolin-4(1H)-one is used as a nutraceutical supplement to support overall health and well-being. Its antioxidant properties and potential to improve mitochondrial function make it a valuable addition to dietary supplements aimed at promoting cardiovascular health and cognitive function.
Used in Research Applications:
In the field of scientific research, 3-butyl-2-hydroxy-1-methylquinolin-4(1H)-one is used as a research tool to study the role of Coenzyme Q and its derivatives in cellular respiration, mitochondrial function, and the pathophysiology of various diseases. Its potential applications in drug development and therapeutic interventions make it an important compound for ongoing research in the biomedical sciences.

Upstream product

• 73281-62-6 3-butyryl-4-hydroxy-1-methyl-1H-quinolin-2-one 
• 773837-37-9 sodium cyanide 
• 601520-14-3 3-butyl-3-chloro-1-methyl-1H,3H-quinoline-2,4-dione 
• 1268819-00-6 3-butyl-1,2,3,4-tetrahydro-1-methyl-2,4-dioxoquinolin-3-yl butylcarbamate 
• 17999-54-1 2-n-butylmalonyl dichloride 
• 35472-56-1 N-methyl-anthranilic acid ethyl ester 
• 133-08-4 diethyl butylmalonate 
• 100-61-8 N-methylaniline 

Downstream Products

• 601520-14-3 3-butyl-3-chloro-1-methyl-1H,3H-quinoline-2,4-dione 
• 186766-14-3 3-butyl-3-hydroxy-1-methylquinoline-2,4(1H,3H)-dione 

Relevant articles and documents

A simple and effective method for the reduction of acyl substituted heterocyclic 1,3-dicarbonyl compounds to alkyl derivatives by zinc - acetic acid - hydrochloric acid

3-Acyl-4-hydroxy-2(1H)-quinolones (1a-k) were reduced in good yields (66-97%) to 3-alkyl-4-hydroxy-2(1H)-quinolinones (2a-k) using zinc powder (particle size 〈45 μm) in acetic acid/hydrochloric acid. This method could be transformed to 3-acetyl-4-hydroxy-

4-HYDROXY-2-QUINOLONES 19. A NEW SYNTHESIS OF 3-ALKYL-2-OXO-4-HYDROXYQUINOLINES

3-Alkyl-subtituted 2-oxo-4-hydroxyquinolines were obtained in high yields from N,N'-di-2-alkoxycarbonylanilides of alkylmalonic acids under conditions of the Dieckmann condensation.Some types of biological activity were found for the compounds synthesized.

Reaction of Tertiary 2-Chloroketones with Cyanide Ions: Application to 3-Chloroquinolinediones

3-Chloroquinoline-2,4-diones react with cyanide ions in dimethyl formamide to give 3-cyanoquinoline-2,4-diones in small yields due to the strong hindrance of the substituent at the C-3 atom. Good yields can be achieved if the substituent at this position

Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

In this study, a 50-membered library of substituted 4-hydroxyquinolin-2(1H)-ones and two closely related analogues was designed, scored in-silico for drug likeness and subsequently synthesized. Thirteen derivatives, all sharing a common 3-phenyl substituent showed minimal inhibitory concentrations against Mycobacterium tuberculosis H37Ra below 10 μM and against Mycobacterium bovis AN5A below 15 μM but were inactive against faster growing mycobacterial species. None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as the most promising member of the library with a MIC of 3.2 μM and a CC50 against MRC-5 of 67.4 μM.

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

Modified riemschneider reaction of 3-thiocyanatoquinolinediones

The Riemschneider reaction of 3-thiocyanatoquinoline-2,4(1H,3H)-diones with conc. H2SO4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C(3) afforded mainly [1,3]thiazolo[5,4-c]quinoline-2,4- diones and 1,9b-dihydro-9b-hydroxythiazolo[5,4-c]quinoline-2,4-diones. In the case of the 3-Bu derivatives of the starting compounds, C-debutylation was also observed. If a Bn group is present at C(3), rapid C-debenzylation of the starting thiocyanates occurred, yielding [1,3]oxathiolo[4,5-c]quinoline-2,4- diones, and mixtures of mono-, di-, and trisulfides derived from 4-hydroxy-3-sulfanylquinoline-2-ones. The reaction mechanism of all of the transformations is discussed. All new compounds were characterized by IR, 1H- and 13C-NMR, and EI and ESI mass spectra, and in some cases, 15N-NMR spectra were also used to characterize new compounds. Copyright

Reaction of 3-hydroxyquinoline-2,4-diones with isocyanates and thermally induced transformation of the reaction products

3-Hydroxyquinoline-2,4-diones 1 react with isocyanates to give novel 1,2,3,4-tetrahydro-2,4-dioxoquinolin-3-yl (alkyl/aryl)carbamates 2 and/or 1,9b-dihydro-9b-hydroxyoxazolo[5,4-c]quinoline-2,4(3aH,5H)-diones 3. Both of these compounds are converted, by boiling in cyclohexylbenzene solution in the presence of Ph3P or 4-(dimethylamino)pyridine, to give 3-(acyloxy)-1,3-dihydro-2H-indol-2-ones 8. All compounds were characterized by IR, and 1H- and 13C-NMR spectroscopy, as well as by EI mass spectrometry. Copyright

Novel tandem hydration/cyclodehydration of α-thiocyanatoketones to 2-oxo-3-thiazolines. Application, to thiazolo[5,4-c]quinoline-2}4(3aH,5H)-dione synthesis

Novel tandem hydration of α-thiocyanatoketones to thiocarbamates followed by in situ cyclodehydration to fused 2-oxo-3-thiazolines is described. The reaction is applied to the synthesis of [1,3]-thiazolo[5,4-c]quinoline-2, 4(3aH,5H)-diones (4). Concentrated sulfuric acid was found to be critical for the reaction as both corresponding 2,3-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanates (2) and S-(2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamates (3) rapidly hydrolyze in the presence of water to 4-hydroxyquinolin-2(1H)-ones (1).

Halogenation Reactions in Position 3 of Quinoline-2,4-dione Systems by Electrophilic Substitution and Halogen Exchange

3-Substituted 4-hydroxy-2(1H)-quinolones 3, 5, 7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones 9 or 10.Reactions of 3, 5, 7 with chloroform gives the dichloromethyl quinolinediones 11.Halogen exchange leads from the chloro quinolinediones 10 to fluoro quinolinedones 12 and to azido quinolinediones 13.Similarly the dichloro quinolinediones 10an reacts to the difluoro quinolinedione 14, which is reduced to the 3-fluoro-4-hydroxyquinolone 16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione 15.Keywords.Fluorination; 4-Hydroxy-2(1H)-quinolones, 3-alkyl/3-aryl/3-fluoro; 1-Hydroxy-benzoquinolizine-3-ones, 2-alkyl/3-aryl; Quinoline-2,4(1H,3H)-diones, 3-azido-3-alkyl/3-aryl, 3-bromo-3-alkyl/3-aryl, 3-chloro-3-alkyl/3-aryl, 3-fluoro-3-alkyl/3-aryl, 3-dichloromethyl-3-alkyl/3-aryl, 3-chloro-3-fluoro.