109549-03-3

Basic information

• Product Name: 2(1H)-Quinolinone, 4-hydroxy-6,7-diMethoxy-1-Methyl-
• Synonyms: 2(1H)-Quinolinone, 4-hydroxy-6,7-diMethoxy-1-Methyl-
• CAS NO: 109549-03-3
• Molecular Formula: C12H13NO4
• Molecular Weight: 235.23592
• Mol File: 109549-03-3.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(1H)-Quinolinone, 4-hydroxy-6,7-diMethoxy-1-Methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Quinolinone, 4-hydroxy-6,7-diMethoxy-1-Methyl-(109549-03-3)
• EPA Substance Registry System: 2(1H)-Quinolinone, 4-hydroxy-6,7-diMethoxy-1-Methyl-(109549-03-3)

Safety Data

• Hazardous Substances Data: 109549-03-3(Hazardous Substances Data)

Usage

Type of compound

chemical compound, alkaloid

Occurrence

naturally occurring in various plant species

Pharmacological properties

potential antioxidant and anti-inflammatory effects

Potential use

treatment of neurodegenerative diseases and cancer

Chemical structure

quinoline ring system with a hydroxyl group, two methoxy groups, and a methyl group at position 1

Unique properties

given by the presence of functional groups (hydroxyl, methoxy, and methyl) attached to the quinoline ring system.

Upstream product

• 141-82-2 malonic acid 
• 35162-34-6 N-methyl-3,4-dimethoxyaniline 

Relevant articles and documents

4-Cyano-6,7-dimethoxycarbostyrils with solvent- and pH-independent high fluorescence quantum yields and emission maxima

Highly fluorescent and stable 6,7-dimethoxy-2-oxoquinoline-4-carbonitriles (11) were synthesized starting from appropriate 4-hydroxyquinolones 3 via reactive 4-chloroquinolones 8 by using toluenesulfinates as catalysts. In contrast to the well-described 4-trifluoromethyl-substituted analogues 18, N-substituted derivatives 11 fluoresce in water, polar, and apolar solvents in a narrow 430-440-nm window with almost constant quantum yield of 0.5. Equal excitation is possible in the broad double maximum between 385 and 410 nm yielding identical data between pH 1 and 11. These properties could lead to a broadly usable fluorescence standard. N-Alkylation with bromoacetate yields ester 13 in good yields. Reactive succinimidoyl (OSu) ester 15 was prepared by saponification to acid 14. With amino acids or peptides, linking to labeled derivatives 17 was achieved under mild conditions in slightly basic aqueous media. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.