6563-36-6

Basic information

• Product Name: 5,7,3',4'-Taxifolin tetramethyl ether
• Synonyms: (2R,3R)-2-(3,4-Dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-2,3-dihydro-4H-1-benzopyran-4-one;(2R,3R)-3-Hydroxy-3',4',5,7-tetramethoxyflavanone;5,7,3',4'-Taxifolin tetramethyl ether
• CAS NO: 6563-36-6
• Molecular Formula: C₁₉H₂₀O₇
• Molecular Weight: 360.36
• Mol File: 6563-36-6.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,7,3',4'-Taxifolin tetramethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7,3',4'-Taxifolin tetramethyl ether(6563-36-6)
• EPA Substance Registry System: 5,7,3',4'-Taxifolin tetramethyl ether(6563-36-6)

Safety Data

• Hazardous Substances Data: 6563-36-6(Hazardous Substances Data)

Upstream product

• 77-78-1 dimethyl sulfate 
• 480-18-2 taxifolin 
• 51079-25-5 (2R,3S)-(+)-catechin 3',4',5,7-tetramethyl ether 
• 154-23-4 catechin 
• 186581-53-3 diazomethane 
• 27297-45-6 (2R,3R)-(+)-dihydroquercetin-3-β-D-glucopyranoside 
• 29838-67-3 astilbin 

Downstream Products

• 14613-67-3 2r-(3,4-Dimethoxy-phenyl)-5,7-dimethoxy-chroman-3t,4ξ-diol 
• 737758-21-3 3',4',5,7-tetramethyldihydroquercetin-3-yl neopentylene phosphite 
• 14613-67-3 (2R^*,3S^*,4S^*)-5,7,3',4'-tetramethoxyflavan-3,4-diol 
• 14613-67-3 (2R^*,3S^*,4R^*)-5,7,3',4'-tetramethoxyflavan-3,4-diol 
• 35499-74-2 3’,4’,5,7-tetra-O-methyl-4β-hydroxycatechin 
• 87303-89-7 (+)-(2R,3S,4R)-3,4-dihydroxy-5,7,3',4'-tetramethoxyflavan 
• 855-97-0 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 
• 74628-43-6 (2S)-5,7,3',4'-tetramethoxyflavanone 
• 25121-65-7 (+/-)-3t-Acetoxy-2r-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chroman 
• 1244-78-6 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone 
• 18207-63-1 2-hydroxy-4,6-dimethoxy-2-veratryl-benzofuran-3-one 
• 94757-83-2 2-(3,4-dimethoxy-benzyl)-2,4,6-trimethoxy-benzofuran-3-one 
• 13650-85-6 (+/-)-taxifolin 3-acetyl-5,7,3',4'-tetramethyl ether 
• 13650-85-6 (2R,3R)-3-O-acetyl-5,7,3',4'-tetra-O-methyltaxifolin 

Relevant articles and documents

3-O-carbamoyl-5,7,20-O-trimethylsilybins: Synthesis and preliminary antiproliferative evaluation

To search for novel androgen receptor (AR) modulators for the potential treatment of castration-resistant prostate cancer (CRPC), naturally occurring silibinin was sought after as a lead compound because it possesses a moderate potency towards AR-positive prostate cancer cells and its chemical scaffold is dissimilar to all currently marketed AR antagonists. On the basis of the structure–activity relationships that we have explored, this study aims to incorporate carbamoyl groups to the alcoholic hydroxyl groups of silibinin to improve its capability in selectively suppressing AR-positive prostate cancer cell proliferation together with water solubility. To this end, a feasible approach was developed to regioselectively introduce a carbamoyl group to the secondary alcoholic hydroxyl group at C-3 without causing the undesired oxidation at C2–C3, providing an avenue for achieving 3-O-carbamoyl-5,7,20-O-trimethylsilybins. The application of the synthetic method can be extended to the synthesis of 3-O-carbamoyl-3′,4′,5,7-O-tetramethyltaxifolins. The antiproliferative potency of 5,7,20-O-trimethylsilybin and its nine 3-carbamoyl derivatives were assessed in an AR-positive LNCaP prostate cancer cell line and two AR-null prostate cancer cell lines (PC-3 and DU145). Our preliminary bioassay data imply that 5,7,20-O-trimethylsilybin and four 3-O-carbamoyl-5,7,20-O-trimethylsilybins emerge as very promising lead compounds due to the fact that they can selectively suppress AR-positive LNCaP cell proliferation. The IC50 values of these five 5,7,20-O-trimethylsilybins against the LNCaP cells fall into the range of 0.11–0.83 μM, which exhibit up to 660 times greater in vitro antiproliferative potency than silibinin. Our findings suggest that carbamoylated 5,7,20-O-trimethylsilybins could serve as a natural product-based scaffold for new antiandrogens for lethal castration-resistant prostate cancer.

Chemoselective C-4 aerobic oxidation of catechin derivatives catalyzed by the trametes villosa laccase/1-hydroxybenzotriazole system: Synthetic and mechanistic aspects

Catechin derivatives were oxidized in air in the presence of the Trametes villosa laccase/1-hydroxybenzotriazole (HBT) system in buffered water/1,4-dioxane as reactionmedium. The oxidation products, flavan- 3,4-diols and the corresponding C-4 ketones, are

Stereoselective oxidation at C-4 of flavans by the endophytic fungus Diaporthe sp. isolated from a tea plant

The microbial transformation of five flavans (1-5) by endophytic fungi isolated from the tea plant Camellia sinensis was investigated. It was found that the endophytic filamentous fungus Diaporthe sp. oxidized stereoselectively at C-4 position of (+)-catechin (1) and (-)-epicatechin (2) to give the correspondent 3,4-cis-dihydroxyflavan derivatives (6, 10), respectively. (-)-Epicatechin 3-O-gallate (3) and (-)-epigallocatechin 3-O-gallate (4) were also oxidized by the fungus into 3,4-dihydroxyflavan derivatives (10, 12) via (-)-epicatechin (2) and (-)-epigallocatechin (11), respectively. Meanwhile, (-)-gallocatechin 3-O-gallate (5), (-)-catechin (ent-1) and (+)-epicatechin (ent-2), which possess a 2S-phenyl substitution, resisted the biotransformation.