519-96-0

Basic information

• Product Name: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone
• Synonyms: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone;2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-1-benzopyran-4-one;3,5,7-Trihydroxy-6-methoxy-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one;6-Methoxyquercetin;Petuletin;2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxychromen-4-one
• CAS NO: 519-96-0
• Molecular Formula: C₁₆H₁₂O₈
• Molecular Weight: 332.26168
• EINECS: 208-280-8
• Mol File: 519-96-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 256 °C
• Boiling Point: 684.1°Cat760mmHg
• Flash Point: 258.8°C
• Appearance: /
• Density: 1.73g/cm³
• Vapor Pressure: 1.19E-19mmHg at 25°C
• Refractive Index: 1.772
• PKA: 6.29±0.40(Predicted)
• CAS DataBase Reference: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone(519-96-0)
• EPA Substance Registry System: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone(519-96-0)

Safety Data

• Hazardous Substances Data: 519-96-0(Hazardous Substances Data)

Usage

Description

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone, also known as Patuletin, is an antioxidant flavonoid belonging to the trimethoxyflavone class. It is characterized by its unique chemical structure, which includes a benzopyrone core with three hydroxyl groups at positions 3, 5, and 7, a methoxy group at position 6, and a dihydroxyphenyl group at position 2. This structure endows Patuletin with potent antioxidant and anti-inflammatory properties, making it a valuable compound for various applications.

Uses

Used in Pharmaceutical Applications:
Patuletin is used as a therapeutic agent for its antioxidant and anti-inflammatory properties. It has been shown to protect cells from oxidative stress and reduce inflammation, making it a promising candidate for the treatment of various diseases and conditions associated with oxidative stress and inflammation.
Used in Nutraceutical Applications:
Patuletin is used as an additive in the nutraceutical industry due to its antioxidant properties. It can be incorporated into dietary supplements and functional foods to enhance their health-promoting benefits and support overall well-being.
Used in Cosmetic Applications:
In the cosmetic industry, Patuletin is used as an active ingredient in skincare products for its antioxidant and anti-inflammatory effects. It can help 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:
Patuletin can be used as a natural preservative in the food and beverage industry due to its antioxidant properties. It can help extend the shelf life of products by preventing oxidation and rancidity, ensuring freshness and quality.
Used in Agricultural Applications:
In agriculture, Patuletin can be employed as a natural pesticide or growth promoter due to its antioxidant and anti-inflammatory properties. It can help protect plants from environmental stressors, enhance their growth, and improve crop yields.

InChI:InChI=1/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3

Upstream product

• 188927-61-9 7-Benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3,5-dihydroxy-6-methoxy-chromen-4-one 
• 19833-25-1 3,5,7,3′,4′-pentahydroxy-6-methoxyflavone 7-O-β-D-glucopyranoside 
• 19833-27-3 3,5,7,3',4'-pentahydroxy-6-methoxyflavone-3-O-β-D-glucopyranoside 
• 188927-56-2 Toluene-4-sulfonic acid 7-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-5-isopropoxy-6-methoxy-4-oxo-4H-chromen-3-yl ester 
• 188927-46-0 Toluene-4-sulfonic acid 7-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-5-hydroxy-6-methoxy-4-oxo-4H-chromen-3-yl ester 
• 1027843-57-7 3,4-Bis-benzyloxy-benzoic acid 2-acetyl-5-benzyloxy-3-isopropoxy-4-methoxy-phenyl ester 
• 188927-36-8 1-(4-Benzyloxy-6-hydroxy-2-isopropoxy-3-methoxy-phenyl)-3-(3,4-bis-benzyloxy-phenyl)-propane-1,3-dione 
• 188927-41-5 7-Benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-hydroxy-5-isopropoxy-6-methoxy-chromen-4-one 
• 188927-51-7 7-Benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-5-isopropoxy-6-methoxy-chromen-4-one 
• 188927-31-3 4-benzyloxy-6-hydroxy-3-methoxy-2-isopropoxyacetophenone 
• 7499-99-2 1-(2,4-dihydroxy-3,6-dimethoxy)phenylethanone 
• 3162-52-5 1-(4-benzyloxy-2-hydroxy-3,6-dimethoxy-phenyl)-ethanone 
• 3162-51-4 1-(2,4-Bis-benzyloxy-3,6-dimethoxy-phenyl)-ethanone 
• 188927-62-0 1-(4-Benzyloxy-2-isopropoxy-3,6-dimethoxy-phenyl)-ethanone 

Downstream Products

• 1251-84-9 3,5,6,7,3',4'-Hexamethoxyflavon 
• 90-18-6 quercetagetin 
• 67443-87-2 3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-6-methoxy-chromen-4-one 
• 1226784-84-4 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-(8-2H)-4H-1-benzopyran-4-one 
• 1067670-15-8 3,3',4',7-tetra-O-cinnamoylpatuletin 
• 479-90-3 artemetin 

Relevant articles and documents

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Flavanoids from the Rudbeckia Hirta L. Herb

Seven crystalline flavanoids: 6,7-dimethoxy-3,5,3',4'-tetrahydroxyflavone 3-O-rhamnoside 1; 3,5,6,7,3',4'-hexahydroxyflavone 7-O-glucoside (quecetagitrin) 2; 6-methoxy-3,5,7,3',4'-pentahydroxyflavone 7-O-glucoside (patulitrin) 3; 3,5,7,3',4'-pentahydroxyflavone 7-O-glucoside (quercimetrin) 4; 6,7-dimethoxy-3,5,3',4'-tetrahydroxyflavone 5; dimethoxy-3,5,4'-trihydroxyflavone 3-O-rhamnoside 6; and 6,7-dimethoxy-3,5,3',4'-tetrahydroxyflavone 3-O-glucoside 7; have been isolated from methanolic extract of the Rudbeckia hirta L. herb by column chromatography on cellulose and polyamide.These compounds were identified by using UV, 1H NMR, 13C NMR, EI-MS and FD-MS.Four compounds: 1, 4, 5, and 6 have been found for the first time in this plant.

FLAVONOL GLYCOSIDES IN LEAVES OF SPINACIA OLERACEA

Besides spinatoside (3,6-dimethoxy-5,7,3',4'-tetrahydroxyflavone 4'-O-β-D-glucopyranuronide), three new flavonol glycosides have now been isolated from the polar fractions of the methanolic extract of Spinacia oleracea.They have been identified as patuletin 3-O-β-D-glucopyranosyl-(1->6)-2)>-β-D-glucopyranoside, patuletin 3-O-β-gentiobioside and spinacetin 3-O-β-gentiobioside, respectively. Key Word Index - Spinacia oleracea; Chenopodiaceae; spinach; 6-methoxy-3,5,7,3',4'-pentahydroxyflavone 3-O-β-D-glucosyl-(1->6)-2)>-β-D-glucoside; 6-methoxy-3,5,7,3',4'-pentahydroxyflavone 3-O-β-gentiobioside; 6,3'-dimethoxy-3,5,7,4'-tetrahydroxyflavone 3-O-β-D-gentiobiside; spinatoside.