679398-81-3

Basic information

• Product Name: 4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin
• Synonyms: 4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin
• CAS NO: 679398-81-3
• Molecular Weight: 600.533
• Mol File: 679398-81-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin(679398-81-3)
• EPA Substance Registry System: 4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin(679398-81-3)

Safety Data

• Hazardous Substances Data: 679398-81-3(Hazardous Substances Data)

Upstream product

• 679398-80-2 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin 
• 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 
• 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 
• 679398-78-8 4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin 

Downstream Products

• 20486-34-4 apigenin-4'-O-β-D-glucopyranoside 

Relevant articles and documents

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.