6665-66-3

Basic information

• Product Name: 5,6-DIHYDROXYFLAVONE
• Synonyms: 4H-1-benzopyran-4-one, 5,6-dihydroxy-2-phenyl-; 5,6-Dihydroxy-2-phenyl-4H-chromen-4-one
• CAS NO: 6665-66-3
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• Product Categories: Di-substituted Flavones
• Mol File: 6665-66-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 189-190 °C
• Boiling Point: 494.399°C at 760 mmHg
• Flash Point: 193.53°C
• Appearance: /
• Density: 1.443g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.699
• PKA: 6.55±0.40(Predicted)
• CAS DataBase Reference: 5,6-DIHYDROXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIHYDROXYFLAVONE(6665-66-3)
• EPA Substance Registry System: 5,6-DIHYDROXYFLAVONE(6665-66-3)

Safety Data

• Hazardous Substances Data: 6665-66-3(Hazardous Substances Data)

Usage

Description

5,6-Dihydroxyflavone is a naturally occurring flavonoid compound found in various plants, such as mosses, peaches, and cherry tomatoes. It is known for its antioxidant and anti-inflammatory properties, and is being studied for its potential neuroprotective and cognitive-enhancing effects. Research has shown that 5,6-dihydroxyflavone can promote the growth and survival of neurons, making it a potential candidate for the treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's. Additionally, it has been found to have anti-cancer properties, with studies showing its ability to inhibit the growth of cancer cells in various types of cancer. 5,6-Dihydroxyflavone is also being investigated for its potential role in the treatment of anxiety and depression, as it has been shown to have anxiolytic and antidepressant effects in animal studies. Overall, 5,6-dihydroxyflavone is a promising compound with a wide range of potential therapeutic applications.

Uses

Used in Pharmaceutical Industry:
5,6-Dihydroxyflavone is used as a neuroprotective agent for its potential to promote the growth and survival of neurons, making it a candidate for the treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's.
Used in Oncology:
5,6-Dihydroxyflavone is used as an anti-cancer agent for its ability to inhibit the growth of cancer cells in various types of cancer.
Used in Mental Health:
5,6-Dihydroxyflavone is used as an anxiolytic and antidepressant agent for its potential role in the treatment of anxiety and depression, as demonstrated in animal studies.

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

Upstream product

• 548-58-3 primetin 
• 118021-60-6 6-hydroxy-5-methoxy-2-phenyl-4H-chromen-4-one 
• 858801-68-0 8-hydroxy-5-methoxy-2-phenyl-chromen-4-one 
• 408336-74-3 5,8-dimethoxy-2-phenyl-chromen-4-one 
• 532-32-1 sodium benzoate 
• 33539-20-7 6-methoxy-2,5-dihydroxyacetophenone 
• 93-97-0 benzoic acid anhydride 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 67645-95-8 5-hydroxy-8-methoxy-2-phenyl-chromen-4-one 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 491-78-1 5-Hydroxyflavone 
• 699-83-2 2,6-dihydroxylacetophenone 

Downstream Products

• 6665-77-6 5,6-diacetoxy-2-phenyl-chromen-4-one 
• 85395-95-5 5-hydroxy-6-methoxy-2-phenyl-4H-chromen-4-one 
• 33554-48-2 5,6-dimethoxyflavone 
• 118021-60-6 6-hydroxy-5-methoxy-2-phenyl-4H-chromen-4-one 
• 26505-96-4 5,7-di-O-methyl-8-iodochrysin 

Relevant articles and documents

Role of some food-grade synthesized flavonoids on the control of ochratoxin a in aspergillus carbonarius

Ochratoxin A (OTA) is a mycotoxin with a serious impact on human health. In Mediterranean countries, the black Aspergilli group, in particular Aspergillus carbonarius, causes the highest OTA contamination. Here we describe the synthesis of three polyphenolic flavonoids: 5-hydroxy-6,7-dimethoxy-flavone (MOS), 5,6-dihydroxy-7-methoxy-flavone (NEG), and 5,6 dihydroxy-flavone (DHF), as well as their effect on the prevention of OTA biosynthesis and lipoxygenase (LOX) activity in A. carbonarius cultured in a conducive liquid medium. The best control effect on OTA biosynthesis was achieved using NEG and DHF. In fungal cultures treated with these compounds at 5, 25, and 50 μg/mL, OTA biosynthesis significantly decreased throughout the 8-day experiment. NEG and DHF appear to have an inhibiting effect also on the activity of LOX, whereas MOS, which did not significantly inhibit OTA production, had no effect on LOX activity. The presence of free hydroxyls in catecholic position in the molecule appears to be a determining factor for significantly inhibiting OTA biosynthesis. However, the presence of a methoxy group in C-7 in NEG could slightly lower the molecule’s reactivity increasing OTA inhibition by this molecule at 5 μg/mL. Polyphenolic flavonoids present in edible plants may be easily synthesized and used to control OTA biosynthesis.

Selective and efficient oxidative modifications of flavonoids with 2-iodoxybenzoic acid (IBX)

2-Iodoxybenzoic acid (IBX), a mild and efficient hypervalent iodine oxidant, has been utilised in different reaction conditions to perform several efficient oxidative modifications of flavonoids. Fine-tuning of the reaction conditions allowed remarkably selective modifications of these compounds. At room temperature, IBX proved to be an excellent reagent for a highly regioselective aromatic hydroxylation of monohydroxylated flavanones and flavones, generating the corresponding catecholic derivatives showing high antioxidant activity. At 90 °C, IBX efficiently dehydrogenated a large panel of methoxylated flavanones to their corresponding flavones exhibiting anticancer activity. IBX polystyrene has also been utilised to increase the recovery of highly polar compounds. Following the first oxidation, the reagent was recovered and reused in several runs without loss of efficiency and selectivity. The first example of an application of IBX polystyrene in a dehydrogenation reaction has been described.

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.