308366-15-6

Basic information

• Product Name: daidzein-7-O-α-D-glucopyranosyl-(1-> 4)-O-β-D-glucopyranoside
• Synonyms: daidzein-7-O-α-D-glucopyranosyl-(1-> 4)-O-β-D-glucopyranoside
• CAS NO: 308366-15-6
• Molecular Weight: 578.527
• Mol File: 308366-15-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: daidzein-7-O-α-D-glucopyranosyl-(1-> 4)-O-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: daidzein-7-O-α-D-glucopyranosyl-(1-> 4)-O-β-D-glucopyranoside(308366-15-6)
• EPA Substance Registry System: daidzein-7-O-α-D-glucopyranosyl-(1-> 4)-O-β-D-glucopyranoside(308366-15-6)

Safety Data

• Hazardous Substances Data: 308366-15-6(Hazardous Substances Data)

Upstream product

• 552-66-9 daidzin 
• 316790-20-2 (1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane 
• 9005-25-8 starch 

Relevant articles and documents

Boronic-Acid-Catalyzed Regioselective and 1,2- cis -Stereoselective Glycosylation of Unprotected Sugar Acceptors via SNi-Type Mechanism

Regio- and 1,2-cis-stereoselective chemical glycosylation of unprotected glycosyl acceptors has been in great demand for the efficient synthesis of natural glycosides. However, simultaneously regulating these selectivities has been a longstanding problem in synthetic organic chemistry. In nature, glycosyl transferases catalyze regioselective 1,2-cis-glycosylations via the SNi mechanism, yet no useful chemical glycosylations based on this mechanism have been developed. In this paper, we report a highly regio- and 1,2-cis-stereoselective SNi-type glycosylation of 1,2-anhydro donors and unprotected sugar acceptors using p-nitrophenylboronic acid (10e) as a catalyst in the presence of water under mild conditions. Highly controlled regio- and 1,2-cis-stereoselectivities were achieved via the combination of boron-mediated carbohydrate recognition and the SNi-type mechanism. Mechanistic studies using the KIEs and DFT calculations were consistent with a highly dissociative concerted SNi mechanism. This glycosylation method was applied successfully to the direct glycosylation of unprotected natural glycosides and the efficient synthesis of a complex oligosaccharide with minimal protecting groups.

Synthesis of β-maltooligosaccharides of glycitein and daidzein and their anti-oxidant and anti-allergic activities

The production of β-maltooligosaccharides of glycitein and daidzein using Lactobacillus delbrueckii and cyclodextrin glucanotransferase (CGTase) as biocatalysts was investigated. The cells of L. delbrueckii glucosylated glycitein and daidzein to give their corresponding 4′- and 7-O-β-glucosides. The β-glucosides of glycitein and daidzein were converted into the corresponding β-maltooligosides by CGTase. The 7-O-β- glucosides of glycitein and daidzein and 7-O-β-maltoside of glycitein showed inhibitory effects on IgE antibody production. On the other hand, β-glucosides of glycitein and daidzein exerted 2,2-diphenyl-1- picrylhydrazyl (DPPH) free-radical scavenging activity and supeoxide-radical scavenging activity.