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

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

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

• 188927-56-2 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 
• 188927-62-0 1-(4-Benzyloxy-2-isopropoxy-3,6-dimethoxy-phenyl)-ethanone 
• 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 
• 188927-61-9 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 

Downstream Products

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

Relevant articles and documents

Chromatographic profiles and identification of new phenolic components of Ginkgo biloba leaves and selected products

Ginkgo biloba leaves and their extracts are one of the most widely used herbal products and/or dietary supplements in the world. A systematic study of the phenolic compounds is necessary to establish quality parameters. A modified LC-DAD-ESI/MS method was used to obtain chromatographic profiles for the flavonoids and terpene lactones of Ginkgo biloba leaves. The method was used to identify 45 glycosylated flavonols and flavones, 3 flavonol aglycones, catechin, 10 biflavones, a dihydroxybenzoic acid, and 4 terpene lactones in an aqueous methanol extract of the leaves. The extracted G. biloba leaf products contained the same flavonoids as the raw leaves except for the lack of biflavones. The detected glycosylated flavonol contents were equal to or more than 0.0008% of the dry plant material. This is the first report of the presence of more than 20 of these flavonoids in G. biloba.

Studies of the selective O-alkylation and dealkylation of flavonoids. XXII. A convenient method for synthesizing 3,5,7-trihydroxy-6-methoxyflavones

The demethylation of 3,4-dioxygenated 6-methoxy-2- isopropoxyacetophenones was studied and it was found that 4-benzyloxy-6- hydroxy-3-methoxy-2-isopropoxyacetophenone was easily obtained from 4- benzyloxy-3,6-dimethoxy-2-isopropoxyacetophenone by selective demethylation with anhydrous aluminum bromide-sodium iodide in acetonitrile. The acetophenone was converted into 7-benzyloxy-3-hydroxy-6-methoxy-5- isopropoxyflavones by cyclization followed by oxidation with dimethyldioxirane. The isopropoxy group in the flavones was selectively cleaved with anhydrous aluminum chloride via the corresponding tosylates to give 7-benzyloxy-3,5-dihydroxy-6-methoxyflavones, which were converted into the desired 3,5,7-trihydroxy-6-methoxyflavones by hydrogenolysis. The process was suitable as a general method for synthesizing 3,5,7-trihydroxy-6- methoxyflavones and five flavones were synthesized. We also examined the 13C-NMR spectra of twelve kinds of 3,5,6,7-tetraoxygenated 4'- methoxyflavones and revised the proposed structure of a natural flavone.

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.

OMBUIN 3-SULPHATE FROM FLAVERIA CHLORAEFOLIA

Key Word Index-Flaveria chloraefolia; Compositae; ombuin 3-sulphate; flavonol sulphate.Abstract-One novel flavonoid sulphate ester and two known non-sulphated flavonoids were isolated from the leaves of Flaveria chloraefolia.The novel sulphated conjugate is 7,4'-dimethylquercetin (ombuin) 3-sulphate, and the known compounds are 6-methoxyquercetin and its 3-glucoside.The structure of ombuin 3-sulphate was established by UV spectroscopy, acid hydrolysis followed by EIMS of the aglycone, as well as enzymatic synthesis.

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.

FLAVONOID GLYCOSIDES OF KALANCHOE SPATHULATA

Key Word Index - Kalanchoe spathulata; Crassulaceae; flavonoids; quercetin 3-O-glucoside-7-O-rhamnoside; kaempferol 3-O-rhamnoside; patuletin 3,7-di-O-rhamnoside. A new glycoside, patuletin 3,7-O-rhamnoside, together with patuletin, quercetin, quercetin 3-O-glucoside-7-O-rhamnoside, kaempferol and kaempferol 3-O-rhamnoside were identified from leaves and flowers of Kalanchoe spathulata.