548-58-3

Basic information

• Product Name: 5,8-Dihydroxyflavone
• Synonyms: 5,8-Dihydroxyflavone;primetin;5,8-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one
• CAS NO: 548-58-3
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• Mol File: 548-58-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 230-231 °C
• Boiling Point: 497.4°Cat760mmHg
• Flash Point: 194.8°C
• Appearance: /
• Density: 1.443g/cm³
• Vapor Pressure: 1.62E-10mmHg at 25°C
• Refractive Index: 1.698
• PKA: 7.45±0.40(Predicted)
• CAS DataBase Reference: 5,8-Dihydroxyflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-Dihydroxyflavone(548-58-3)
• EPA Substance Registry System: 5,8-Dihydroxyflavone(548-58-3)

Safety Data

• Hazardous Substances Data: 548-58-3(Hazardous Substances Data)

Usage

Definition

ChEBI: A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 5 and 8.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 645, 1984 DOI: 10.1021/jo00178a013

InChI:InChI=1/C15H10O4/c16-10-6-7-11(17)15-14(10)12(18)8-13(19-15)9-4-2-1-3-5-9/h1-8,16-17H

Upstream product

• 491-78-1 5-Hydroxyflavone 
• 858801-68-0 8-hydroxy-5-methoxy-2-phenyl-chromen-4-one 
• 77298-64-7 8-hydroxyflavone 
• 110-86-1 pyridine 
• 699-83-2 2,6-dihydroxylacetophenone 
• 710337-68-1 3-benzoyl-8-hydroxy-2-phenyl-chromen-4-one 
• 50634-02-1 3-benzoyl-7-hydroxyflavone 
• 858801-66-8 8-benzoyloxy-5-methoxy-2-phenyl-chromen-4-one 
• 412022-08-3 3-acetyl-2-hydroxy-4-methoxy-benzaldehyde 
• 56358-73-7 1-(2,3-dihydroxy-6-methoxy-phenyl)-ethanone 
• 118021-63-9 1-(2-benzoyloxy-6-methoxy-phenyl)-ethanone 
• 42079-78-7 5-methoxyflavone 
• 13494-10-5 2',3'-dihydroxyacetophenone 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 

Downstream Products

• 67645-95-8 5-hydroxy-8-methoxy-2-phenyl-chromen-4-one 
• 111475-55-9 5,8-diacetoxy-2-phenyl-chromen-4-one 
• 6665-66-3 5,6-Dihydroxyflavone 
• 87953-83-1 5,8-Quinoflavone 
• 87953-84-2 6-chloro-5,8-dihydroxyflavone 
• 87953-85-3 C₂₉H₁₇ClO₆ 
• 89971-00-6 5,6,8-trihydroxy-2-phenyl-chromen-4-one 

Relevant articles and documents

Structure-activity relationships for α-glucosidase inhibition of baicalein, 5,6,7-trihydroxyflavone: The effect of A-ring substitution

In order to estimate the effects of the A-ring hydroxyl group of baicalein (5,6,7-trihydroxyflavone, 1) on rat intestinal α-glucosidase inhibition, flavone, monohydroxyflavones, dihydroxyflavones, and methylated derivatives of 5,6,7-trihydroxyflavone were used for the structure-activity relationship (SAR) study. The importance of the 6-hydroxyl group of baicalein was validated for an exertion of the activity. And also, the tested flavones which lacked a hydroxyl substituent on any of positions 5, 6, or 7, showed no activity. Hence, the 5,6,7-trihydroxyflavone structure was concluded to be crucial for the potent inhibitory activity. In addition, an introduction of electron-withdrawing or electron-donating groups at position 8 of baicalein led to a dramatic decrease for activity, except for 8-fluoro-5,6,7-trihydroxyflavone, which carried a less bulky substituent on position 8. Hence, this result suggested that a sterically bulky substituent on C-8 of baicalein was detrimental for the activity regardless of its electronic nature. Through examining the inhibitory mechanism of baicalein against rat intestinal α-glucosidase, it was suggested to be a mixed type inhibition.