5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one

5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one is a synthetic organic compound belonging to the class of flavonoids. This compound is of interest in the field of medicinal chemistry due to its potential biological activities, including antioxidant and anti-inflammatory properties.

Chemical Structure and Properties

The chemical structure of 5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one is characterized by a chromene backbone, which is a bicyclic structure consisting of a benzene ring fused to a pyran ring. The presence of hydroxyl groups at the 5 and 7 positions, a methoxy group at the 6 position, and a phenoxyphenyl group at the 2 position contribute to its unique chemical properties.

Molecular Formula

The molecular formula of this compound is C₂₂H₁₆O₆.

Molecular Weight

The molecular weight of 5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one is approximately 376.36 g/mol.

Solubility

This compound is generally soluble in organic solvents such as dimethyl sulfoxide (DMSO) and ethanol, but it has limited solubility in water.

Synthesis

The synthesis of 5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one typically involves the condensation of appropriate phenolic precursors under acidic or basic conditions. The reaction may require the use of catalysts to facilitate the formation of the chromene ring.

Biological Activity

Research has indicated that 5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one exhibits several biological activities:

Antioxidant Activity

The compound has been shown to scavenge free radicals, thereby reducing oxidative stress in biological systems. This activity is attributed to the presence of hydroxyl groups, which can donate hydrogen atoms to neutralize reactive oxygen species.

Anti-inflammatory Activity

Studies suggest that this compound may inhibit the production of pro-inflammatory cytokines, making it a potential candidate for the treatment of inflammatory diseases.

Potential Applications

Due to its biological activities, 5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one is being investigated for its potential use in pharmaceuticals, particularly in the development of drugs aimed at treating conditions related to oxidative stress and inflammation.

Safety and Toxicology

As with many synthetic compounds, the safety profile of 5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one must be thoroughly evaluated. Preliminary studies suggest low toxicity, but further research is necessary to fully understand its effects in vivo.

Also see

• Flavonoid
• Antioxidant
• Inflammation
• Medicinal chemistry