39028-59-6

Basic information

• Product Name: 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-3',4',5,7-tetrahydroxyflavonol
• Synonyms: 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-3',4',5,7-tetrahydroxyflavonol
• CAS NO: 39028-59-6
• Molecular Weight: 632.532
• Mol File: 39028-59-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-3',4',5,7-tetrahydroxyflavonol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-3',4',5,7-tetrahydroxyflavonol(39028-59-6)
• EPA Substance Registry System: 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-3',4',5,7-tetrahydroxyflavonol(39028-59-6)

Safety Data

• Hazardous Substances Data: 39028-59-6(Hazardous Substances Data)

Upstream product

• 116973-12-7 5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 183067-65-4 7-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3,5-dihydroxy-4H-chromen-4-one 
• 1332833-26-7 C₅₇H₅₂O₁₆ 
• 153-18-4 rutin 
• 357194-03-7 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one 
• 117-39-5 quercetol 
• 477244-18-1 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-5,7-dihydroxy-4H-chromen-4-one 

Downstream Products

• 131021-81-3 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol 
• 482-35-9 isoquercetin 

Relevant articles and documents

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK

In order to understand the effect of structure-activity relationships on melanogenesis using B16 melanoma cells, 19 quercetin derivatives were synthesized. Among the synthesized compounds, 3-O-methylquercetin (11) and 3′,4′,7-O-trimethylquercetin (14) increased melanin content more potently than the positive control theophylline, while exhibiting low cytotoxicity. Compound 11 exhibited less melanogenesis-stimulating activity than compound 14. However, 11 increased the expression of tyrosinase and tyrosinase-related protein 1 (TRP-1) to a greater extent than 14, thereby suggesting that melanogenesis in melanoma cells does not depend solely on the expression of the enzymes catalyzing melanin biosynthesis. Furthermore, 14 also stimulated the expression of the microphthalmia-associated transcription factor (MITF) and p-p38 mitogen activated protein kinase (MAPK), while they were not increased by 11. These results suggest that 11 may enhance the expression of tyrosinase and TRP-1 by regulating the proteasomal degradation of melanogenic enzymes and/or by activating other transcriptional factors regulating enzyme expression.

Design, synthesis, and biological evaluation of a novel series of quercetin diacylglucosides as potent anti-MRSA and anti-VRE agents

A series of novel quercetin diacylglucosides were designed and first synthesized by Steglich esterification on the basis of MRSA strains inhibiting natural compound A. The in vitro inhibition of different multi-drug resistant bacterial strains and Escherichia coli DNA gyrase B was investigated. In the series, compound 10h was up to 128-fold more potent against vancomycin-resistant enterococci and more effective than A, which represents a promising new candidate as a potent anti-MRSA and anti-VRE agent.