82854-32-8

Basic information

• Product Name: 2-(2,6-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one
• CAS NO: 82854-32-8
• Molecular Formula: C₁₅H₁₂O₇
• Molecular Weight: 304.25
• Mol File: 82854-32-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 713.4°C at 760 mmHg
• Flash Point: 273.7°C
• Density: 1.702g/cm³
• Vapor Pressure: 2.33E-21mmHg at 25°C
• Refractive Index: 1.762
• CAS DataBase Reference: 2-(2,6-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,6-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one(82854-32-8)
• EPA Substance Registry System: 2-(2,6-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one(82854-32-8)

Safety Data

• Hazardous Substances Data: 82854-32-8(Hazardous Substances Data)

Upstream product

• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 79834-12-1 2,6-bis((2-methoxyethoxy)methoxy)benzaldehyde 
• 387-46-2 2,6-dihydroxybenzaldehyde 
• 480-66-0 2,4,6-trihydroxyacetophenone 

Relevant articles and documents

Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure-activity relationship

To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells.