6962-57-8

Usage

Preparation

Preparation by Fries rearrangement of 1,4-diacetoxy- 2,6-di-methoxybenzene with aluminium chloride in nitrobenzene at r.t.

InChI:InChI=1/C10H12O5/c1-5(11)8-6(12)4-7(14-2)9(13)10(8)15-3/h4,12-13H,1-3H3

Upstream product

• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 7702-17-2 4-(acetyloxy)-3,5-dimethoxyphenyl acetate 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 108-24-7 acetic anhydride 
• 15233-65-5 2,6-dimethoxy-1,4-hydroquinone 
• 530-55-2 2,6-dimethoxy-p-quinone 
• 5333-45-9 1,2,3,5-tetramethoxybenzene 
• 75-36-5 acetyl chloride 
• 77-78-1 dimethyl sulfate 
• 64-19-7 acetic acid 
• 21919-63-1 3-acetyl-4-hydroxy-2,6-dimethoxyphenyl acetate 
• 642-71-7 3,4,5-trimethoxyphenol 

Downstream Products

• 67197-57-3 5,6-dihydroxy-7-methoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 
• 18003-33-3 3',4',5,6,7-pentahydroxyflavone 
• 2306-27-6 sinensetin 
• 6951-57-1 6,4'-Dihydroxy-5,7-dimethoxy-flavanon-(4) 
• 10176-71-3 ladanein 
• 103777-33-9 1-(3-Butoxy-6-hydroxy-2,4-dimethoxy-phenyl)-ethanone 
• 103777-36-2 1-(6-Hydroxy-2,4-dimethoxy-3-octyloxy-phenyl)-ethanone 
• 103777-34-0 1-(6-Hydroxy-2,4-dimethoxy-3-pentyloxy-phenyl)-ethanone 
• 103777-35-1 1-[6-Hydroxy-2,4-dimethoxy-3-(3-methyl-butoxy)-phenyl]-ethanone 
• 103777-38-4 1-(3-Dodecyloxy-6-hydroxy-2,4-dimethoxy-phenyl)-ethanone 
• 103777-39-5 1-(6-Hydroxy-2,4-dimethoxy-3-tetradecyloxy-phenyl)-ethanone 
• 103777-40-8 1-(3-Hexadecyloxy-6-hydroxy-2,4-dimethoxy-phenyl)-ethanone 
• 103777-41-9 1-(6-Hydroxy-2,4-dimethoxy-3-octadecyloxy-phenyl)-ethanone 
• 98892-84-3 1-(3-Hexyloxy-6-hydroxy-2,4-dimethoxy-phenyl)-ethanone 

Relevant academic research and scientific papers

chromane derivatives, and pharmaceutical composition for preventing or treating neovascular eye disease or cancer containing the same as an active ingredient

The invention relates to compounds of formula 1 which are chroman derivatives. The present invention provides a pharmaceutical composition for treating diseases associated with cancer or neovascularization comprising a hydrate thereof, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof. Chemical Formula 1. In Chemical Formula 1 R, R represents a hydrogen atom. 1 R/R2 R/R3 R/R4 R/R5 R/R6 R/R7 As defined in the description of the invention.

A practical synthesis of the flavone, scutellarein

A practical and economical five-step synthesis of the flavone scutellarein has been achieved in 60% overall yield using the available and cheap 2,6-dimethoxy-1,4-benzoquinone as starting material. The reaction sequence involved reduction to the corresponding quinol, Friedel-Crafts acetylation, Claisen-Schmidt condensation with p-methoxybenzaldehyde, cyclisation and demethylation. The procedure is operationally simple and amenable to scale-up synthesis.

Method for preparing scutellarin

The invention relates to a method for preparing scutellarin. According to the method, the scutellarin can be efficiently prepared from 2,6-dimethoxy benzoquinone as a starting raw material through five reactions of reduction, Friedel-Crafts acetylation, Claisen condensation, dehydrogenation oxidation cyclization and demethylation. The starting raw material and a reagent are cheap and easily available, synthetic steps are few, the operation is simple and convenient, the production control is simple, the product yield is high, and the purity is high. The method is applicable to large-scale preparation and production application of the scutellarin.

Method for preparing baicalein

The invention discloses a method for preparing baicalein. According to the method, 2,6-dimethoxy-p-benzoquinone used as an initial raw material is subjected to reduction, Friedel-Crafts acetylation, claisen condensation, dehydrogenation oxidation cyclization and demethylation five reactions to obtain baicalein with high yield. The method uses low-price and easily-available initial raw material, reagent and the like, has few synthesizing steps, is easy and convenient to operate and easy for production control, has high product yield and high purity, and is suitable for large-scale preparation and production application of baicalein.

A practical and economical high-yielding, six-step sequence synthesis of a flavone: Application to the multigram-scale synthesis of ladanein

Herein we report a short and economic synthesis of the antiviral flavonoid lead ladanein (1). Ladanein is obtained from 2,6-dimethoxyquinone (11) in six steps with 51% overall yield. After a high-yielding reductive acetylation and Fries rearrangement, the

Flavone derivatives and their use

The present invention relates to flavone derivatives and to compositions containing one or more of these flavone derivatives. The present invention further relates to flavone derivatives or compositions for use in the treatment and/or prevention of a vira

FLAVONE DERIVATIVES AND THEIR USE

The present invention relates to flavone derivatives and to compositions containing one or more of these flavone derivatives. The present invention further relates to fiavone derivatives or compositions for use in the treatment and/or prevention of a vira

Preparation of two sets of 5,6,7-trioxygenated dihydroflavonol derivatives as free radical scavengers and neuronal cell protectors to oxidative damage

An unusual class of 5,6,7-trioxygenated dihydroflavonols (3a-e and 4a-j) were designed and prepared. Their antioxidative properties were assessed by examining their capacities in several in vitro models, including superoxide anion and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, rat liver homogenate lipid peroxidation inhibition, PC12 cells protection from oxidative damage, and xanthine oxidase inhibition. These dihydroflavonols displayed positive quenching abilities towards O2{radical dot} - and DPPH free radicals, in which the majority exhibited superior antioxidant properties to Vitamin C. cis-Configurated compound (±)-3e demonstrated remarkable inhibition to LPO with an IC50 value of 1.9 ± 0.3 μM, which was apparently stronger than that of quercetin (IC50 = 6.0 ± 0.4 μM). trans-Configurated dihydroflavonol (±)-4h exhibited significant protective effect on PC12 cells against oxidative damage with an EC50 value of 41.5 ± 5.3 μM, more effective compared to that of quercetin (EC50 = 81.8 ± 8.7 μM). The 6-OH-5,7-dimethoxy analogue (±)-3d showed significant inhibition of xanthine oxidase with an IC50 value of 16.0 ± 0.8 μM, which is superior to that of allopurinol (IC50 = 23.5 ± 2.0 μM). In addition to the hypothesized action mechanism of the bio-active compounds, 3D modeling was used to analyze the relationship between the minimized-energy structures and antioxidant activities.

Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3′,4′,5,6,7,8- heptamethoxyflavone, quercetin and its derivatives were synthesized.