20486-34-4

Basic information

• Product Name: 4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)phenyl beta-D-glucopyranoside
• CAS NO: 20486-34-4
• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.3775
• Mol File: 20486-34-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 763.3°C at 760 mmHg
• Flash Point: 271.5°C
• Density: 1.642g/cm³
• Vapor Pressure: 1.7E-24mmHg at 25°C
• Refractive Index: 1.717
• CAS DataBase Reference: 4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)phenyl beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)phenyl beta-D-glucopyranoside(20486-34-4)
• EPA Substance Registry System: 4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)phenyl beta-D-glucopyranoside(20486-34-4)

Safety Data

• Hazardous Substances Data: 20486-34-4(Hazardous Substances Data)

Upstream product

• 679398-82-4 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-L-glucopyranosyl)apigenin 
• 595564-89-9 7-O-tert-butyldimethylsilylapigenin 
• 679398-75-5 2-(4-hydroxyphenyl)-5-hydroxy-7-(tert-butyldimethylsiloxy)chroman-4-one 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 679398-83-5 4'-O-(2,3,4,6-tetra-O-acetyl-β-L-glucopyranosyl)apigenin 
• 133-89-1 UDP-glucose 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 162489-61-4 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranosyl fluoride 
• 679398-77-7 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 679398-80-2 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin 
• 679398-81-3 4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin 

Downstream Products

• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 

Relevant articles and documents

Functional Characterization and Protein Engineering of a Triterpene 3-/6-/2′-O-Glycosyltransferase Reveal a Conserved Residue Critical for the Regiospecificity

Engineering the function of triterpene glucosyltransferases (GTs) is challenging due to the large size of the sugar acceptors. In this work, we identified a multifunctional glycosyltransferase AmGT8 catalyzing triterpene 3-/6-/2′-O-glycosylation from the medicinal plant Astragalus membranaceus. To engineer its regiospecificity, a small mutant library was built based on semi-rational design. Variants A394F, A394D, and T131V were found to catalyze specific 6-O, 3-O, and 2′-O glycosylation, respectively. The origin of regioselectivity of AmGT8 and its A394F variant was studied by molecular dynamics and hydrogen deuterium exchange mass spectrometry. Residue 394 is highly conserved as A/G and is critical for the regiospecificity of the C- and O-GTs TcCGT1 and GuGT10/14. Finally, astragalosides III and IV were synthesized by mutants A394F, T131V and P192E. This work reports biocatalysts for saponin synthesis and gives new insights into protein engineering of regioselectivity in plant GTs.

Total synthesis of apigenin 7,4′-di-O-β-glucopyranoside, a component of blue flower pigment of Salvia patens, and seven chiral analogues

We have succeeded in the first total synthesis of apigenin 7,4′-di-O-β-D-glucopyranoside (1a), a component of blue pigment, protodelphin, from naringenin (2). Glycosylation of 2 according to Koenigs-Knorr reaction provided a monoglucoside 4a in 80% yield, and this was followed by DDQ oxidation to give apigenin 7-O-glucoside (12a). Further glycosylation of 4′-OH of 12a with 2,3,4,6-tetra-O-acetyl-α-D- glucopyranosyl fluoride (5a) was achieved using a Lewis acid-and-base promotion system (BF3·Et2O, 2,6-di-tert-butyl-4- methylpyridine, and 1,1,3,3-tetramethylguanidine) in 70% yield, and subsequent deprotection produced 1a. Synthesis of three other chiral isomers of 1a, with replacement of D-glucose at 7 and/or 4′-OH by L-glucose (1b-d), and four chiral isomers of apigenin 7-O-β-glucosides (6a,b) and 4′-O-β- glucosides (7a,b) also proved possible.