54141-72-9

Basic information

• Product Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxy-6-methyl-oxa n-2-yl)oxy-chroman-4-one
• Synonyms: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxy-6-methyl-oxa n-2-yl)oxy-chroman-4-one;Nsc245342;Neoisoastilbin;(2S,3R)-3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one
• CAS NO: 54141-72-9
• Molecular Formula: C₂₁H₂₂O₁₁
• Molecular Weight: 450.39
• Mol File: 54141-72-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 168-169 °C
• Boiling Point: 801.1°Cat760mmHg
• Flash Point: 282.9°C
• Appearance: /
• Density: 1.74g/cm³
• Vapor Pressure: 4.42E-27mmHg at 25°C
• Refractive Index: 1.748
• PKA: 7.34±0.60(Predicted)
• CAS DataBase Reference: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxy-6-methyl-oxa n-2-yl)oxy-chroman-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxy-6-methyl-oxa n-2-yl)oxy-chroman-4-one(54141-72-9)
• EPA Substance Registry System: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxy-6-methyl-oxa n-2-yl)oxy-chroman-4-one(54141-72-9)

Safety Data

• Hazardous Substances Data: 54141-72-9(Hazardous Substances Data)

Usage

General Description

The chemical "2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxy-6-methyl-oxa n-2-yl)oxy-chroman-4-one" is a complex compound with a long name that includes various functional groups such as phenol, chroman, and oxan. It contains multiple hydroxyl groups, indicating its potential antioxidant properties. The presence of these functional groups also suggests potential biological activity, such as anti-inflammatory and anti-cancer properties. The compound's chemical structure indicates its potential as a natural product and could possibly be found in a variety of plant-based sources. Further research is needed to fully understand the pharmacological and biological activities of this chemical.

InChI:InChI=1/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3

Upstream product

• 29838-67-3 astilbin 
• 294203-78-4 (2R,3S,4S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-ol 
• 294203-76-2 (2R,3S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 294203-79-5 (2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one 
• 104495-20-7 2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride 
• 80152-99-4 1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose 

Downstream Products

• 122147-54-0 (2R)-2r-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3t-α-L-rhamnopyranosyloxy-chroman-4-one 
• 121707-94-6 (2R)-5,7-diacetoxy-2r-(3,4-diacetoxy-phenyl)-3t-(tri-O-acetyl-α-L-rhamnopyranosyloxy)-chroman-4-one 
• 29838-67-3 (2S,3R)-dihydroquercetin 3-O-α-L-rhamnoside 
• 480-18-2 (+/-)-taxifolin 
• 54081-47-9 Neoastilbin 
• 29838-67-3 (2R,3S)-dihydroquercetin 3-O-α-L-rhamnoside 
• 73-34-7 L-rhamnose 
• 6563-36-6 (+)-3',4',5,7-tetra-O-methyl-2,3-trans-dihydroquercetin 
• 215257-15-1 3,3',4',5,7-pentahydroxy flavanone 
• 480-18-2 taxifolin 

Relevant articles and documents

Cationic zirconocene- or hafnocene-based Lewis acids in organic synthesis: Glycoside-flavonoid analogy

Cationic metallocene species, generated from Cp2MCl2 and AgClO4 (M=Zr, Hf), were used for the glycosylation of catechin derivative 2, enabling a concise synthesis of a glycosyl flavonoid, astilbin (1). Further study revealed the efficiency of this Lewis acidic species for SN1-type activation of the C(4) position of catechin derivative 11, enabling selective substitution with various nucleophiles.

First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine

A synthetic route to a biologically active glycosyl flavonoid, astilbin (1), was developed. The tetra-benzyl ether 4, derived from (+)-catechin, was glycosylated with the L-rhamnosyl donor 10 by using Cp2HfCl2-AgClO4, and subsequent oxidation of the C(4)position of the flavan skeleton followed by deprotection gave 1. (C) 2000 Elsevier Science Ltd.