119249-30-8

Basic information

• Product Name: 7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin
• Synonyms: 7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin
• CAS NO: 119249-30-8
• Molecular Weight: 600.533
• Mol File: 119249-30-8.mol

Chemical Properties

• CAS DataBase Reference: 7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin(CAS DataBase Reference)
• NIST Chemistry Reference: 7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin(119249-30-8)
• EPA Substance Registry System: 7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin(119249-30-8)

Safety Data

• Hazardous Substances Data: 119249-30-8(Hazardous Substances Data)

Upstream product

• 31087-58-8 7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 23598-19-8 4'-O-benzylapigenin-7-O-β-D-tetra-O-acetylglucoside 
• 52309-82-7 4′-O-benzylapigenin 
• 10236-47-2 naringin 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 130999-29-0 Apigen-4'7-diyl-di(2,3,4,6-tetra-O-acetyl-β-D-glucopranoside) 
• 679398-72-2 7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4'-O-(2,3,4,6-tetra-O-acetyl-β-L-glucopyranosyl)apigenin 
• 578-74-5 apigenin 7-O-glucoside 

Relevant articles and documents

Semisynthesis of apigenin and acacetin-7-O-β-d-glycosides from naringin and their cytotoxic activities

Apigenin-7-O-β-d-glycosides 1-8 and acacetin-7-O-β-d-glycosides 9-16 were semisynthesized from 4′-O-benzyl apigenin 17 and acacetin 18 by glycosidation and deprotection with the corresponding α-acetylglycosyl bromide, respectively. Compounds 17 and 18 were prepared by iodination followed by base-induced elimination, 4′-O-benzylation, or 4′-O-methylation and acid hydrolysis using naringin as starting material which is readily available and cheap. Their cytotoxic potential against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480) was evaluated by standard MTT method. The results show that compounds 2, 9, and 19 exhibit moderate cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480, while compound 3 exhibits potent cytotoxicity against MCF-7 selectively. Among the synthesized target compounds, 3, 4, 7, 11, 12, 15, and 16 were new compounds, the natural product 8 was the first synthesized and the synthesis of natural products 5, 6, 13, and 14 was efficiently improved by the new synthetic routes.

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.

Chiral molecular recognition on formation of a metalloanthocyanin: A supramolecular metal complex pigment from blue flowers of salvia patens

Most blue flower color is the result of a metalloanthocyanin, a stoichiometric self-assembled supramolecular pigment consisting of six molecules of an anthocyanin, six molecules of an anthocyanin, six molecules of flavone, and two metal atoms. We have iso