genistein-8-c-glucoside

Base Information

• Chemical Name: genistein-8-c-glucoside
• CAS No.: 66026-80-0
• Molecular Formula: C21H20O10
• Molecular Weight: 432.384
• Mol file: 66026-80-0.mol

Synonyms:(1S)-1, 5-Anhydro-1-[5, 7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol;

Chemical Property of genistein-8-c-glucoside

Chemical Property:

• Vapor Pressure: 8.68E-25mmHg at 25°C
• Refractive Index: 1.743
• Boiling Point: 767.7 °C at 760 mmHg
• Flash Point: 273.1 °C
• PSA: 181.05000
• Density: 1.686 g/cm³
• LogP: 0.09170

Purity/Quality:

99%, ^*data from raw suppliers

Genistein8-c-glucoside 99.40% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of genistein-8-c-glucoside

There total 8 articles about genistein-8-c-glucoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

5,7,4'-tri(benzyloxy)-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)isoflavone → 4′,7-dihydroxy-8β-D-glucose isoflavone (66026-80-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; ethyl acetate; at 20 ℃; for 2h; Reagent/catalyst;

Reference yield: 63.0%

7,4'-di(benzyloxy)-5-hydroxy-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)isoflavone → 4′,7-dihydroxy-8β-D-glucose isoflavone (66026-80-0)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2010.06.077

Reference yield:

(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 (898550-57-7) → 4′,7-dihydroxy-8β-D-glucose isoflavone (66026-80-0)

Guidance literature:

(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; With thallium(III) nitrate; In methanol; at 40 ℃; for 23h;

With hydrogenchloride; In 1,4-dioxane; methanol; for 20h; Heating;

With hydrogen; palladium dihydroxide; In methanol; ethyl acetate; at 20 ℃; for 5h;

DOI:10.1016/j.carres.2006.03.038

upstream raw materials:

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

(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

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

4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone

Downstream raw materials:

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Refernces

• 1、 -. "NEW C-GLYCOSYLPOLYPHENOL ANTIDIABETIC AGENTS, EFFECT ON GLUCOSE TOLERANCE AND INTERACTION WITH BETA-AMYLOID. THERAPEUTIC APPLICATIONS OF THE SYNTHESIZED AGENT(S) AND OF GENISTA TENERA ETHYL ACETATE EXTRACTS CONTAINING SOME OF THOSE AGENTS". Paragraph 0077; 0096. . Retrieved 2015/02/19.
• 2、 Sato, Shingo,Hiroe, Kaoru,Kumazawa, Toshihiro,Jun-ichi, Onodera. "Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-β-d-glucopyranosides". . p. 1091 - 1095. Retrieved 2007/10/03.