482-35-9

Basic information

• Product Name: ISOQUERCITRIN
• Synonyms: anosyloxy)-;glucosyl3-quercetin;hirsutrin;quercetin3-beta-glucoside;quercetin3-beta-o-glucoside;quercetin3-d-glucoside;quercetin3-monoglucoside;quercetol3-glucoside
• CAS NO: 482-35-9
• Molecular Formula: C₂₁H₂₀O₁₂
• Molecular Weight: 464.38
• EINECS: 244-488-5
• Product Categories: Antineoplastic
• Mol File: 482-35-9.mol
• Article Data: 40

Chemical Properties

• Melting Point: 230 °C
• Boiling Point: 872.6°Cat760mmHg
• Flash Point: 307.4°C
• Appearance: /
• Density: 1.87g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.803
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.17±0.40(Predicted)
• Stability: Hygroscopic
• BRN: 100989
• CAS DataBase Reference: ISOQUERCITRIN(CAS DataBase Reference)
• NIST Chemistry Reference: ISOQUERCITRIN(482-35-9)
• EPA Substance Registry System: ISOQUERCITRIN(482-35-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: LK8960000
• F: 10-23
• Hazardous Substances Data: 482-35-9(Hazardous Substances Data)

Usage

Chemical Properties

White to Light Yellow Powder

Uses

Different sources of media describe the Uses of 482-35-9 differently. You can refer to the following data:
1. Isoquercitrin was used as standard to compare the retention time of samples for identifying chromatographic peaks during flavonoid identification by Orbitrap UHPLC-MS/MS analysis.
2. Quercetin 3-β-D-glucoside has been used:as a dietary flavonoid supplement to check its binding capacity with human small ubiquitin-related modifier 1 (SUMO1) protein using surface plasmon resonance (SPR)as an inhibitor for Escherichia coli adenosine triphosphate (ATP) synthaseas an anti-aggregation agent to test its activity against β-amyloid, green fluorescent protein?(GFP), and chymotrypsinogen proteins

General Description

Produced and qualified by HWI pharma services GmbH.Exact content by quantitative NMR can be found on the certificate.

Biochem/physiol Actions

Quercetin 3-β-D-glucoside possesses strong antioxidant and anti-inflammatory activities. Being a potent oxygen-radical scavenger, it is a neuroprotective agent that improves Alzheimer′s disease (AD) condition in mice models. It has shown antiproliferative activity against colon, lung, and hepatocellular cell lines and MCF-7 human breast cancer cells in combination with apple extracts.

InChI:InChI=1/C21H20O12/c22-6-12(27)19-16(29)17(30)21(32-19)33-20-15(28)14-11(26)4-8(23)5-13(14)31-18(20)7-1-2-9(24)10(25)3-7/h1-5,12,16-17,19,21-27,29-30H,6H2/t12-,16-,17-,19-,21+/m1/s1

Upstream product

• 133-89-1 UDP-glucose 
• 117-39-5 quercetol 
• 153-18-4 rutin 
• 120221-14-9 (2-chloro-4-nitrophenyl)-β-D-glucopyranoside 
• 7431-83-6 5,7,3',4'-tetrahydroxyflavonol-3-O-[β-D-glucopyranosyl(1→6)]-β-D-glucopyranoside 
• 1332833-27-8 5,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-3-(β-D-glucopyranosyloxy)-4H-chromen-4-one 
• 1332833-26-7 C₅₇H₅₂O₁₆ 
• 116973-12-7 5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one 
• 124097-46-7 quercitin-3-O-β-D-glucoside-7-O-α-L-rhamnoside 
• 131021-81-3 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol 
• 78386-01-3 2-(3-acetoxy-4-(benzyloxy) phenyl)-7-(benzyloxy)-4-oxo-4H-chromene-3,5-diyl diacetate 
• 1064-06-8 3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one 
• 13459-13-7 7,4’-di-O-benzylquercetin 
• 6743-87-9 4',7-di-O-benzyl-3-O-(β-D-glucopyranosyl)quercetin 

Downstream Products

• 18705-98-1 3',4',5,7-tetra-O-acetylquercetin 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranoside) 
• 153874-66-9 6''-O-<2-(methoxycarbonyl)acetyl>isoquercitrin 
• 117-39-5 quercetol 
• 2280-44-6 D-Glucose 
• 492-61-5 β-D-glucose 
• 1139-97-5 2,3,4,6-tetra-O-methyl-D-glucopyranose 
• 855-97-0 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 
• 54542-51-7 quercetin 3-O-(6''-O-acetyl)-β-D-glucopyranoside 
• 743434-65-3 ((2R,3R,4S,5R,6S)-4-acetoxy-6-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl acetate 
• 959833-95-5 isoquercitrin 2'',3'',6''-triacetate 
• 50-99-7 D-glucose 
• 1237534-64-3 ((2R,3S,4S,5R,6S)-6-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl hexanoate 
• 1237535-18-0 ((2R,3S,4S,5R,6S)-6-{(2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl (Z)-octadec-9-enoate 
• 1237534-66-5 ((2R,3S,4S,5R,6S)-6-{(2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl octanoate 

Relevant articles and documents

Isolation and characterization of a glycosyltransferase with specific catalytic activity towards flavonoids from Tripterygium wilfordii

Flavonoids are important secondary metabolites that exist in many medicinal plants. Flavonoid glycosyltransferases can transfer sugar moieties to their parent rings, producing various flavonoid glycosides with significant pharmacological activities. Here, we report the molecular cloning of the O-glycosyltransferase TwUGT2 from Tripterygium wilfordii and its catalytic activity was explored by heterologous expression in E. coli. The results showed that TwUGT2 has specific glycosyltransferase activity towards C-3 and 7 hydroxyl groups of flavonoids, thereby converting quercetin and pinocembrin into isoquercitrin and pinocembrin 7-O-beta-D-glucoside, respectively. The identification of TwUGT2 will provide a useful molecular tool for synthetic biology and contribute to drug discovery. (Figure presented.).

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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.