92873-06-8

Basic information

• Product Name: 5-methoxy-8-bromo-flavanone
• Synonyms: 5-methoxy-8-bromo-flavanone
• CAS NO: 92873-06-8
• Molecular Weight: 333.181
• Mol File: 92873-06-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-methoxy-8-bromo-flavanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methoxy-8-bromo-flavanone(92873-06-8)
• EPA Substance Registry System: 5-methoxy-8-bromo-flavanone(92873-06-8)

Safety Data

• Hazardous Substances Data: 92873-06-8(Hazardous Substances Data)

Upstream product

• 55947-36-9 5-methoxyflavanone 
• 16740-73-1 5-bromo-2-methoxyacetophenone 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Ecofriendly synthesis of halogenated flavonoids and evaluation of their antifungal activity

Brominated and chlorinated flavonoids belonging to different classes (flavanones, flavones and catechins) were prepared from the corresponding flavonoids by a simple and ecofriendly procedure based on the use of sodium halides, aqueous hydrogen peroxide and acetic acid. Pure samples of substrates and products were tested against Trichoderma koningii, Fusarium oxysporum and Cladosporium cladosporioides, common saprotrophic soil and seed fungi, potential pathogens for humans and their activity was expressed as linear mycelial growth inhibition (%). Among them, 8-chloro-5,7,3′,4′-tetramethoxyepicatechin 29, a novel catechin derivative, exhibited a remarkable effect against all tested fungi also at low concentrations.

Chalcones and flavonoids as anti-tuberculosis agents

A series of flavonoids, chalcones and chalcone-like compounds were evaluated for inhibitory activity against Mycobacterium tuberculosis H37Rv. Among them, eight compounds exhibited >90% inhibition on the growth of the bacteria at a concentration of 12.5 μg/mL. Chalcones 1-(2-hydroxyphenyl)-3-(3-chlorophenyl)-2-propen-1-one (22) and 1-(2-hydroxyphenyl)-3-(3-iodophenyl)-2-propen-1-one (37) demonstrated 90 and 92% inhibition, respectively. Chalcone-like compounds (heterocyclic ring-substituted 2-propen-1-one) 1-(4-fluorophenyl)-3-(pyridin-3-yl)-2-propen-1-one (48), 1-(3-hydroxyphenyl)-3-(phenanthren-9-yl)-2-propen-1-one (49), 1-(pyridin-3-yl)-3-(phenanthen-9-yl)-2-propen-1-one (50) and 1-(furan-2-yl)-3-phenyl-2-propen-1-one (51) exhibited 98, 97, 96 and 96% inhibition, respectively. The actual minimum inhibitory concentrations (MIC), defined as the lowest concentration inhibiting 99% of the inoculum, for 22, 37, 48, 49, 50 and 51 were 20.3, 31.5, 48.3, >35.7, 6.8 and 19.2, respectively. A hydrophobic substituent on one aromatic ring, and a hydrogen-bonding group on the other aromatic ring resulted in increased anti-TB activity of the chalcones and chalcone-like compounds. Flavones and flavanones are more geometrically constrained than the corresponding chalcone analogues. The decreased activity of the flavones with respect to the chalcones may be due to the confinement of the terminal aromatic rings to the same plane.