90-18-6

Usage

Uses

Used in Pharmaceutical Industry:
3,3',4',5,6,7-HEXAHYDROXYFLAVONE is used as a pharmaceutical agent for its potential therapeutic effects. Its multiple hydroxy groups allow it to interact with various biological targets, making it a promising candidate for the development of new drugs. It may have potential applications in treating various diseases, including cancer, inflammation, and cardiovascular disorders, due to its antioxidant, anti-inflammatory, and other bioactive properties.
Used in Cosmetic Industry:
In the cosmetic industry, 3,3',4',5,6,7-HEXAHYDROXYFLAVONE is used as an active ingredient for its skin-friendly properties. Its antioxidant and anti-inflammatory activities can help protect the skin from environmental stressors and promote skin health. It may be incorporated into skincare products, such as creams, lotions, and serums, to provide benefits like moisturization, skin brightening, and anti-aging effects.
Used in Food and Beverage Industry:
3,3',4',5,6,7-HEXAHYDROXYFLAVONE can be used in the food and beverage industry as a natural additive due to its potential health benefits. Its antioxidant properties can help protect food products from oxidation and extend their shelf life. Additionally, it may be used as a functional ingredient in beverages and supplements to provide consumers with health-promoting benefits.

InChI:InChI=1/C15H10O8/c16-6-2-1-5(3-7(6)17)15-14(22)13(21)10-9(23-15)4-8(18)11(19)12(10)20/h1-4,16-20,22H

Upstream product

• 489-35-0 gossypetin 
• 62506-94-9 2-(3,4-dimethoxy-phenyl)-5,7,8-trihydroxy-3-methoxy-chromen-4-one 
• 65602-55-3 2-(3,4-dimethoxy-phenyl)-3-hydroxy-5,6,7-trimethoxy-chromen-4-one 
• 72947-60-5 2-(3,4-dimethoxy-phenyl)-6-hydroxy-3,5,7-trimethoxy-chromen-4-one 
• 519-96-0 patuletin 
• 548-75-4 quercetagetin?7?O?β?D?glucoside 
• 10034-85-2 hydrogen iodide 
• 108-95-2 phenol 
• 14639-73-7 1-(3,6-dihydroxy-2,4-dimethoxy-phenyl)-2-methoxy-ethanone 
• 24824-54-2 3,4-dimethoxybenzoic anhydride 
• 114021-62-4 (E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one 
• 66074-98-4 5,6,7,3',4'-pentamethoxyflavanone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 520-18-3 kaempferol 

Downstream Products

• 23370-16-3 5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxychromen-4-one 
• 603-56-5 chrysoplenitin 
• 99-50-3 3,4-Dihydroxybenzoic acid 

Relevant academic research and scientific papers

Formation of UV-honey guides in Rudbeckia hirta

The UV-honey guides of Rudbeckia hirta were investigated by UV-photography, reflectance spectroscopy, LC-MS analysis and studies of the enzymes involved in the formation of the UV-absorbing flavonols present in the petals. It was shown for the first time

New thiophene and flavonoid from tagetes minuta leaves growing in saudi arabia

Phytochemical investigation of the methanolic extract of Tagetes minuta L. (Asteraceae) leaves resulted in the isolation and identification of two new compounds: 5-methyl-2,2',5',2'',5'',2''',5''',2''''-quinquethiophene (1) and quercetagetin-6-O-(6-Ocaffe

Regioselective hydroxylation of diverse flavonoids by an aromatic peroxygenase

Aromatic peroxygenases are extracellular fungal biocatalysts that selectively oxidize a variety of organic compounds. We found that the peroxygenase of the fungus Agrocybe aegerita (AaeAPO) catalyzes the H 2O2-dependent hydroxylation of diverse flavonoids. The reactions proceeded rapidly and regioselectively yielding preferentially monohydroxylated products, e.g., from flavanone, apigenin, luteolin, flavone as well as daidzein, quercetin, kaempferol, and genistein. In addition to hydroxylation, O-demethylation of fully methoxylated tangeretin was catalyzed by AaeAPO. The enzyme was merely lacking activity on the quercetin glycoside rutin, maybe due to sterical hindrance by the bulky sugar substituents. Mechanistic studies indicated the presence of epoxide intermediates during hydroxylation and incorporation of H2O2-derived oxygen into the reaction products. Our results raise the possibility that fungal peroxygenases may be useful for versatile, cost-effective, and scalable syntheses of flavonoid metabolites.

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

In the demethylation of 6-hydroxy-3,4',7-trimethoxy-5-(tosyloxy)flavone with anhydrous aluminum bromide, the 5-tosyloxyl group was eliminated with bromination to give 8-bromo-3,6,7-trihydroxy-4'-methoxyflavone as the main product. When anhydrous aluminum chloride was used in the demethylation of the acetate, the 5-tosyloxyl group was cleaved prior to the demethylation to give 5,6,7-trihydroxy-3,4'-dimethoxyflavone. Demethylation of 6-hydroxy-4',5,7-trimethoxy-3-(tosyloxy)flavone and its acetate with the bromide or chloride afforded the 5,6,7-trihydroxyflavone without the cleavage of the 3-tosyloxyl group, but was not suitable for the general synthesis of the 3,5,6,7-tetrahydroxyflavones because of the difficulty in removing the protecting group. Consequently, it was found that the direct demethylation of 3,6-dihydroxy-5,7-dimethoxyflavones with anhydrous aluminum chloride-sodium iodide in acetonitrile was the most useful general method for synthesizing 3,5,6,7-tetrahydroxyflavones. Additionally, the reported structures of two natural flavones were revised.

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.

FLAVONOID GLYCOSIDES OF ARTEMISIA MONOSPERMA AND A. HERBA-ALBA

Ten flavonoid glycosides were isolated and identified from Artemisia monosperma: vicenin-2, lucenin-2, acacetin 7-glucoside, acacetin 7-rutinoside, the 3-glucosides and 3-rutinosides of quercetin and patuletin, and the 5-glucosides of quercetin and isorhamnetin.From Artemisia herba-alba eight flavonoid glycosides were isolated and identified: isovitexin, vicenin-2, schaftoside, isoschaftoside and the 3-glucosides and 3-rutinosides of quercetin and patuletin.Key Word Index - Artemisia monosperma; A herba-alba; Compositae; flavone and flavonol glycosides.