Quercetin-3-D-xyloside

Base Information

• Chemical Name: Quercetin-3-D-xyloside
• CAS No.: 549-32-6
• Molecular Formula: C20H18 O11
• Molecular Weight: 434.356
• DSSTox Substance ID: DTXSID10415782
• Mol file: 549-32-6.mol

Synonyms:quercetin-3-beta-D-xyloside;quercetin-3-O-beta-D-xylopyranoside;reynoutrin

Chemical Property of Quercetin-3-D-xyloside

Chemical Property:

• Vapor Pressure: 4.74E-29mmHg at 25°C
• Melting Point: 201-203℃
• Boiling Point: 828.1°C at 760 mmHg
• PKA: 6.17±0.40(Predicted)
• Flash Point: 296.3°C
• PSA: 190.28000
• Density: 1.86g/cm³
• LogP: 0.10020
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 434.08491139
• Heavy Atom Count: 31
• Complexity: 711

Purity/Quality:

98%Min ^*data from raw suppliers

Quercetin 3-O-β-D-xylopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@H](C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• Uses: Quercetin 3-O-β-xyloside is a glucoside of Quercetin (Q509500, Dihydrate) which is a flavonoid with anticancer activity. It is a mitochondrial ATPase and phosphodiesterase inhibitor. It Inhibits PI3-kinase activity and slightly inhibits PIP kinase activity. Quercetin has antiproliferative effects on cancer cell lines, reduces cancer cell growth via type II estrogen receptors, and arrests human leukemic T cells in late G1 phase of the cell cycle.

Technology Process of Quercetin-3-D-xyloside

There total 4 articles about Quercetin-3-D-xyloside 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:

2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one (357194-03-7) → avicularin (549-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / dimethylformamide

2: H₂ / Pd/C

3: MeONa; MeOH

With methanol; hydrogen; sodium methylate; potassium carbonate; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.05.061

Reference yield:

Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-3-yl ester (742062-21-1) → avicularin (549-32-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C

2: MeONa; MeOH

With methanol; hydrogen; sodium methylate; palladium on activated charcoal;

DOI:10.1016/j.bmcl.2004.05.061

Reference yield:

Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-3-yl ester → avicularin (549-32-6)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1016/j.bmcl.2004.05.061

upstream raw materials:

2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one

Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-3-yl ester

Downstream raw materials:

D-Xylose

quercetol

Refernces