Guaijaverin

Base Information

• Chemical Name: Guaijaverin
• CAS No.: 22255-13-6
• Molecular Formula: C₂₀H₁₈O₁₁
• Molecular Weight: 434.356
• European Community (EC) Number: 250-156-0
• DSSTox Substance ID: DTXSID60176795
• Nikkaji Number: J94.528E
• Wikipedia: Guaijaverin
• Metabolomics Workbench ID: 136576
• ChEMBL ID: CHEMBL464507
• Mol file: 22255-13-6.mol

Synonyms:guajavarin;quercetin 3-O-alpha-L-arabinoside

Chemical Property of Guaijaverin

Chemical Property:

• Melting Point: 237-239 °C
• Boiling Point: 828.061 °C at 760 mmHg
• PKA: 6.17±0.40(Predicted)
• Flash Point: 296.325 °C
• PSA: 190.28000
• Density: 1.863 g/cm³
• LogP: 0.10020
• Storage Temp.: room temp
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• 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:

99% ^*data from raw suppliers

Quercetin 3-O-alpha-L-Arabinopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• Uses: Quercetin 3-O-α-L-Arabinopyranoside is a derivative of Quercetin (Q509500), 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 Guaijaverin

There total 4 articles about Guaijaverin 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:

quercetol (117-39-5,74893-81-5) + C14H22N2O16P2 (21401-20-7,30329-30-7,38-57-3,97905-92-5,7164-64-9) → quercetin 3-O-L-arabinopyranoside (6743-88-0,22255-13-6,72581-59-0,94131-44-9)

Guidance literature:

With 3-O-glycosyltransferase from Scutellaria baicalensis; In aq. buffer; at 45 ℃; for 1h; pH=9; regiospecific reaction; Enzymatic reaction;

DOI:10.1021/acs.orglett.9b00524

Reference yield:

2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one (357194-03-7) → guaijaverin (6743-88-0,22255-13-6,72581-59-0,94131-44-9)

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,5S)-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 (742062-22-2) → guaijaverin (6743-88-0,22255-13-6,72581-59-0,94131-44-9)

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

upstream raw materials:

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

Acetic acid (2S,3R,4S,5S)-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

quercetol

C₁₄H₂₂N₂O₁₆P₂

Downstream raw materials:

D-Arabinose

quercetol

L-(+)-arabinose

2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone