80366-15-0

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2-(2,6-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihy droxy-, (2R,3R)-
• Synonyms: 4H-1-Benzopyran-4-one, 2-(2,6-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihy droxy-, (2R,3R)-;2',3,5,6',7-Pentahydroxyflavane;2',3,5,6',7-Pentahydroxyflavanone;(2R,3R)-2',3,5,6',7-Pentahydroxyflavanone;3,5,7,2',6'-Pentahydroxyflavanone;Ganhuangemin;trans-5,7,2',6'-Tetrahydroxyflavanonol;2',6'-Dihydroxypinobanksin
• CAS NO: 80366-15-0
• Molecular Formula: C₁₅H₁₂O₇
• Molecular Weight: 304.2516
• Mol File: 80366-15-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 713.4°Cat760mmHg
• Flash Point: 273.8°C
• Appearance: /
• Density: 1.702g/cm³
• Vapor Pressure: 2.33E-21mmHg at 25°C
• Refractive Index: 1.762
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2-(2,6-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihy droxy-, (2R,3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2-(2,6-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihy droxy-, (2R,3R)-(80366-15-0)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2-(2,6-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihy droxy-, (2R,3R)-(80366-15-0)

Safety Data

• Hazardous Substances Data: 80366-15-0(Hazardous Substances Data)

Usage

Description

4H-1-Benzopyran-4-one, 2-(2,6-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-, also known as 3,5,7,2'',6''-Pentahydroxyflavanone, is a flavonoid compound isolated from Scutellaria rehderiana. It is characterized by its unique chemical structure, featuring a benzopyran-4-one core with multiple hydroxyl groups. 4H-1-Benzopyran-4-one, 2-(2,6-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihy droxy-, (2R,3R)exhibits potent antioxidant activity, making it a valuable compound for various applications.

Uses

Used in Pharmaceutical Industry:
4H-1-Benzopyran-4-one, 2-(2,6-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)is used as a pharmaceutical agent for its antioxidant properties. Its ability to neutralize free radicals and protect cells from oxidative damage makes it a promising candidate for the development of drugs targeting various diseases associated with oxidative stress, such as neurodegenerative disorders, cardiovascular diseases, and cancer.
Used in Nutraceutical Industry:
In the nutraceutical industry, 4H-1-Benzopyran-4-one, 2-(2,6-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)is used as a dietary supplement to promote overall health and well-being. Its antioxidant activity can help support the immune system, enhance cognitive function, and improve skin health by combating the signs of aging caused by oxidative stress.
Used in Cosmetic Industry:
4H-1-Benzopyran-4-one, 2-(2,6-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)is used as an active ingredient in cosmetic products for its antioxidant and anti-aging properties. It can be incorporated into skincare formulations to protect the skin from environmental stressors, reduce the appearance of fine lines and wrinkles, and promote a more youthful and radiant complexion.
Used in Food and Beverage Industry:
In the food and beverage industry, 4H-1-Benzopyran-4-one, 2-(2,6-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)is used as a natural preservative and antioxidant to extend the shelf life of products and maintain their quality. Its ability to neutralize free radicals can help prevent the oxidation of fats and oils, thus preserving the taste, texture, and nutritional value of food products.

InChI:InChI=1/C15H12O7/c16-6-4-9(19)12-10(5-6)22-15(14(21)13(12)20)11-7(17)2-1-3-8(11)18/h1-5,14-19,21H/t14-,15+/m0/s1

Upstream product

• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 82854-32-8 5,7,3,2′,6′-pentahydroxy flavanone 
• 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.