66026-80-0

Basic information

• Product Name: genistein-8-c-glucoside
• Synonyms: genistein-8-c-glucoside
• CAS NO: 66026-80-0
• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.3775
• Mol File: 66026-80-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 767.7 °C at 760 mmHg
• Flash Point: 273.1 °C
• Appearance: /
• Density: 1.686 g/cm³
• Vapor Pressure: 8.68E-25mmHg at 25°C
• Refractive Index: 1.743
• CAS DataBase Reference: genistein-8-c-glucoside(CAS DataBase Reference)
• NIST Chemistry Reference: genistein-8-c-glucoside(66026-80-0)
• EPA Substance Registry System: genistein-8-c-glucoside(66026-80-0)

Safety Data

• Hazardous Substances Data: 66026-80-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H20O10/c22-6-13-17(27)18(28)19(29)21(31-13)15-12(25)5-11(24)14-16(26)10(7-30-20(14)15)8-1-3-9(23)4-2-8/h1-5,7,13,17-19,21-25,27-29H,6H2/t13-,17-,18+,19-,21+/m1/s1

Upstream product

• 1333163-46-4 genistein 7-O-xylosyl-8-C-glucoside 
• 898550-56-6 4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone 
• 169566-46-5 1-(4,6-bis(benzyloxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)ethanone 
• 898550-57-7 (2E)-1-[2-acetoxy-4,6-dibenzyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)]phenyl-3-(4-benzyloxyphenyl)prop-2-en-1-one 
• 147899-33-0 Malonic acid mono-{(2R,3S,4R,5R,6S)-6-[5,7-dihydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl} ester 

Downstream Products

• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 

Relevant articles and documents

A new isoflavone glycoside from the aerial parts of Retama sphaerocarpa

sphaerocarpa. Its structure was elucidated by spectroscopic methods.

Glucose uptake enhancing activity of puerarin and the role of C-glucoside suggested from activity of related compounds

Chemical treatment of diabetes mellitus is widely studied and controlling of blood glucose level is the main course of therapy. In type 2 diabetes mellitus, insulin resistance is the major problem. An isoflavone C-glucoside, puerarin (1), is known to enhance glucose uptake into the insulin sensitive cell and is thought to be a candidate for treatment of diabetes mellitus. We synthesized 1 and several derivatives to apply for the structure-activity relationship study. The result against 3T3-L1 adipocyte indicated that the C-glucoside part of 1 is unconcerned in its activity when tested in vitro and the main structure responsible for its activity was the isoflavone moiety.

Isoflavone glucosides exist as their 6''-O-malonyl esters in Pueraria lobata and its cell suspension cultures

Methanol extracts prepared by mild and careful procedure from cultured cells of P. lobata were analyzed by reverse phase high performance liquid chromatography (HPLC) to reveal that most of the isoflavone 7-O-glucosides daidzin(1) and genistin(2), and 8-C-glucoside puerarin(3), exiost as their 6''-O-malonyl esters. The presence of malonyl esters of 1, 2 and 3 was also detected in the fresh roots and stems of P. lobata.