54675-30-8

Basic information

• Product Name: 1-Ethyl-4-hydroxy-2(1H)-quinolinone
• Synonyms: 1-Ethyl-4-hydroxy-2(1H)-quinolinone;1-ethyl-4-hydroxy-1,2-dihydroquinolin-2-one;1-Ethyl-4-hydroxy-1H-quinolin-2-one
• CAS NO: 54675-30-8
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Mol File: 54675-30-8.mol

Chemical Properties

• Melting Point: 255-264 °C(Solv: ethanol (64-17-5))
• Boiling Point: 307.6°C at 760 mmHg
• Flash Point: 139.8°C
• Appearance: /
• Density: 1.264g/cm³
• Vapor Pressure: 0.000311mmHg at 25°C
• Refractive Index: 1.62
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 1-Ethyl-4-hydroxy-2(1H)-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Ethyl-4-hydroxy-2(1H)-quinolinone(54675-30-8)
• EPA Substance Registry System: 1-Ethyl-4-hydroxy-2(1H)-quinolinone(54675-30-8)

Safety Data

• Hazardous Substances Data: 54675-30-8(Hazardous Substances Data)

Usage

Type

Synthetic derivative of quinoline

Applications

Pharmaceutical and cosmetic products

Properties

Antioxidant and antimicrobial

Activities

Antifungal, antibacterial, and antiviral

Uses

Topical creams, ointments, and lotions

Potential applications

Treatment of skin conditions, preservative in personal care products

Research status

Further research needed to understand potential health effects and safety profile

InChI:InChI=1/C11H11NO2/c1-2-12-9-6-4-3-5-8(9)10(13)7-11(12)14/h3-7,14H,2H2,1H3

Upstream product

• 66134-57-4 3-acetyl-1-ethyl-4-hydroxy-2(1Η)-quinolinone 
• 103-69-5 N-ethyl-N-phenylamine 
• 1663-67-8 malonoyl dichloride 
• 161185-28-0 6-ethyl-4-hydroxy-2,5-dioxo-5,6-dihydro-2H-pyrano[3,2-c]quinoline 
• 331963-41-8 C₁₉H₁₇N₃O₄ 
• 105-53-3 diethyl malonate 
• 405112-23-4 4-hydroxy-2-oxo-1-ethyl-1,2-dihydroquinoline-3-carboxylic acid 

Downstream Products

• 1005133-44-7 C₂₂H₂₀ClNO₃ 
• 1005133-40-3 C₂₂H₂₁NO₃ 
• 1005133-45-8 C₂₃H₂₂ClNO₃ 

Relevant articles and documents

4-Hydroxyquinol-2-ones. 87. Unusual synthesis of 1-R-4-hydroxy-1-oxo-1,2- dihydroquinoline-3-carboxylic acid pyridylamides

4-Chloro-2-oxo-1,2-dihydroquinoline-3-carboxylic acids and their esters react with aminopyridines in refluxing DMF to give the corresponding 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyridylamides. Their structures were proved by 1

Synthesis and colon anticancer activity of some novel thiazole/-2-quinolone derivatives

We direct for the synthesis of 1,6,7-trisubstituted-4-phenylthiazol-2(3H)-ylidene)hydrazono)methyl)quinolin-2-one derivatives by the reaction of corresponding thiosemicarbazone derived by 2-quinolone derivatives with 2-bromoacetophenones in presence of triethylamine at room temperature. The mechanism of the formed products was discussed. The structure of the obtained products was fully characterized using different spectral techniques including infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS) together with elemental analyses. The new synthesized compounds showed a moderate colon anticancer activity.

Synthesis of new quinolinones from 3-nitropyranoquinolinones

Alkaline hydrolysis of 3-nitropyranoquinolinones (6-alkyl-4-hydroxy-3-nitro-2H-pyrano[3,2-c]quinoline-2,5(6H)-diones) for different reaction times gave five products which were formed by the progressive degradation of the nitropyrano ring. Varying amounts of 3-nitroacetylquinolinones, quinolinones with side-chains of β- And β-ketoacids, quinolinone-3-carboxylic acids and 4-hydroxyquinolinones were isolated. With the aim of preparing new biologically active quinolone derivatives, the products of reaction of the 3-nitropyranoquinolinones with side-chains of α- And β-ketoacids with some nitrogen and carbon nucleophiles were also studied, some giving rise to annulated products.

Substituted quinolinones. Part 19. New and unexpected results from oxidation of 3-acetyl-1-alkyl- 4-hydroxyquinolin-2(1H)-ones using selenium dioxide

Oxidation of 3-acetyl-1-alkyl-4-hydroxyquinolin-2(1H)-ones using selenium dioxide under Riley conditions was described. The oxidation reaction produced a mixture of 2 unexpected α-keto acid and its dehydrated dimer derivatives. The oxidation reaction was studied under different reaction conditions in order to maximize the yields and optimize reaction conditions. Also, 1-alkyl-4-hydroxy-3-(2-nitroacetyl)quinolin-2(1H)-one and/or 3-acetyl-1-alkyl-4-diflouro-boryloxyquinolin-2(1H)-one derivatives were subjected to the same oxidation reaction giving rise improved reaction yields and selectivity in case of the boron-complex. Alkaline degradation of the dehydrated dimers led to formation of the 4-hydroxy-2-oxoquinoline-3-carboxylic acids while under the same conditions the α-keto acids underwent deoxalylation.

4-Hydroxy-2-quinolones. 149*. Synthesis, chemical transformations, and biological properties of β-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2- dihydro-quinoline-4-carboxylic acids

Two methods of preparation have been proposed and the synthesis has been effected of a large series of β-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1, 2-dihydroquinoline-3-carboxylic acids. The possibility of using various condensing agents for converting them into the corresponding 1,3,4-oxa-diazoloquinolines has been studied. Results are given of an investigation of the antitubercular activity of the synthesized compounds.

A convenient one-pot synthesis of pyrano[3,2-c]quinolin-2,5(6H)-dione and 2H,5H-pyrano[3,2-c]chromene-2,5-dione derivatives

The preparation of novel pyrano[3,2-c]quinolin-2,5(6H)-dione and 2H,5H-pyrano[3,2-c]chromene-2,5-dione derivatives starting from 4-hydroxyquinolin-2(1H)-ones and 4-hydroxy-2H-chromene-2-one with chlorocarbonyl ketenes is described. This method provides a new route to produce fused pyrano derivatives in good to excellent yields in a short experimental time. Georg Thieme Verlag Stuttgart.

Syntheses of 3-Acyl-4-hydroxy-2(1H)-quinolones

3-Acyl-4-hydroxy-2(1H)-quinolones 5 are obtained by hydrolytic ring opening and subsequent decarboxylation from the corresponding pyranoquinolin-2,5(6H)-diones 4, which in turn are easily obtained from 1:2 condensation of of anilines 1 with diethyl malonate 2a or 1:1 condensation of diethyl alkyl- or arylmalonates 2b-e with 4-hydroxy-2(1H)-quinolones 3.Nitropyranoquinolinediones 6 furnish after ringopening 3-nitroacetyl-4-hydroxy-2(1H)-quinolones 8.Pyranoquinolines 7 and 9 with acetyl- or aminosubstituents are hydrolyzed during basic ringopening to yield 5.

Anti-allergenic carbostyril derivatives

A class of 4-hydroxy-3-nitroearbostyril derivatives are useful in the inhibition of certain types of antigen antibody reactions.