22248-13-1

Usage

Preparation

Preparation by reaction of dimethyl sulfate on 3,6- di-hydroxy-2-methoxyacetophenone with potassium carbonate in boiling benzene (67%).

Upstream product

• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 33539-20-7 6-methoxy-2,5-dihydroxyacetophenone 

Downstream Products

• 5653-53-2 6-hydroxy-2,3-dimethoxy-benzoic acid 
• 20046-00-8 1-(2-Hydroxy-5,6-dimethoxyphenyl)-3-(2,6-dimethoxyphenyl)-1,3-propandion 
• 2980-32-7 1,3,5,8-tetrahydroxyxanthone 
• 16266-96-9 5-hydroxy-6,2'-dimethoxyflavone 
• 16266-97-0 5,6,2'-trimethoxyflavone 
• 3749-31-3 5,6,2'-trimethoxyflavanone 
• 14813-19-5 2-(2,6-dimethoxyphenyl)-5.6-dimethoxy-4H-1-benzopyran-4-one 
• 20107-46-4 1-(2,6-Dimethoxyphenyl)-3-(2-hydroxy-5,6-dimethoxyphenyl)-2refH-propen-⁽¹⁾-on-⁽³⁾-ol-(1trans) 
• 95280-52-7 5,6-dimethoxyflavanone 

Relevant academic research and scientific papers

Biotransformation of isofraxetin-6-O-β-D-glucopyranoside by Angelica sinensis (Oliv.) Diels callus

Isofraxetin-6-O-β-D-glucopyranoside, identified from traditional medicinal herbal Xanthoceras sorbifolia Bunge, has been demonstrated to be a natural neuroinflammatory inhibitor. In order to obtain more derivatives with potential anti-neuroinflammatory effects, biotransformation was carried out. According to the characteristics of coumarin skeleton, suspension cultures of Angelica sinensis (Oliv.) Diels callus (A. sinensis callus) were employed because of the presence of diverse phenylpropanoids biosynthetic enzymes. As a result, 15 products were yielded from the suspension cultures, including a new coumarin: 8′-dehydroxymethyl cleomiscosin A (1), together with 14 known compounds. Their structures were elucidated by extensive spectroscopic analysis. Furthermore, the biotransformed pathways were discussed. Among them, compound 13 was transformed from isofraxetin-6-O-β-D-glucopyranoside, while compounds 1–6, 10–12, 14–15 were derived from the culture medium stimulated by the substrate. The biotransformation processes include hydroxylation, oxidation and esterification. Furthermore, their inhibitory effects on lipopolysaccharide (LPS)-activated nitric oxide (NO) production were evaluated in BV2 microglial cells. It is worth noting that, 1, 1′-methanediylbis(4-methoxybenzene) (3), obtucarbamates A (5), 2-nonyl-4-hydroxyquinoline N-oxide (10) and 1H-indole-3-carbaldehyde (11) exhibited significant inhibitory effect against neuroinflammation with IC50values at 1.22, 10.57, 1.02 and 0.76?μM respectively, much stronger than that of the positive control minocycline (IC5035.82?μM).

CHEMOTHERAPEUTIC FLAVONOIDS, AND SYNTHESES THEREOF

Substituted flavonoid compounds, and pharmaceutical formulations of flavonoid compounds are described. Also described are processes for preparing flavonid compounds, as are methods for treating cancer in mammals using the described flavonoid compounds or pharmaceutical formulations thereof.

Synthesis and cancer chemopreventive activity of zapotin, a natural product from Casimiroa edulis

An efficient method has been developed to synthesize zapotin (5,6,2′,6′-tetramethoxyflavone), a component of the edible fruit Casimiroa edulis, on a multigram scale. The synthesis utilizes a regioselective C-acylation of a dilithium dianion derived from a substituted o-hydroxyactophenone to afford a β-diketone intermediate that can be cyclized to zapotin in good overall yield, thus avoiding the inefficient Baker-Venkataraman rearrangement pathway. Zapotin was found to induce both cell differentiation and apoptosis with cultured human promyelocytic leukemia cells (HL-60 cells). In addition, the compound inhibits 12-O-tetrade-canoylphorbol 13-acetate (TPA)-induced ornithine decarboxylase (ODC) activity with human bladder carcinoma cells (T24 cells), and TPA-induced nuclear factor-kappa B (NF-κB) activity with human hepatocellular liver carcinoma cells (HepG2 cells). These data suggest that zapotin merits further investigation as a potential cancer chemopreventive agent.

Gastroprotective flavone/flavanone compounds with therapeutic effect on inflammatory bowel disease

PCT No. PCT/KR97/00144 Sec. 371 Date Jan. 14, 1999 Sec. 102(e) Date Jan. 14, 1999 PCT Filed Jul. 25, 1997 PCT Pub. No. WO98/04541 PCT Pub. Date Feb. 5, 1998The present invention relates to novel flavone/flavanone compounds or their pharmaceutically acceptable salts and process for preparation thereof for protecting gastrointestinal tracts against gastritis, ulcers and inflammatory bowel disease.

5-HYDROXY-6,2'-DIMETHOXYFLAVONE FROM PRIMULA DENTICULATA

A novel natural flavone, 5-hydroxy-6,2'-dimethoxyflavone, was isolated from the leaf exudate of Primula denticulata.Its structure was elucidated by spectral studies and confirmed by synthesis.This flavone shows unusual fragments in its mass spectrum which