5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

Base Information

• Chemical Name: 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• CAS No.: 301-16-6
• Molecular Formula: C22H22 O11
• Molecular Weight: 462.41
• NSC Number: 167408
• DSSTox Substance ID: DTXSID90952509
• Wikidata: Q105367643
• Mol file: 301-16-6.mol

Synonyms:Scoparin;NSC-167408;DTXSID90952509;NSC167408;4H-1-Benzopyran-4-one,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-;1,5-Anhydro-1-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-1-benzopyran-8-yl]hexitol

Chemical Property of 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

Chemical Property:

• Vapor Pressure: 9.99E-26mmHg at 25°C
• Melting Point: 253°
• Boiling Point: 781.6°Cat760mmHg
• PKA: 6.24±0.40(Predicted)
• Flash Point: 273.9°C
• PSA: 190.28000
• Density: 1.649g/cm³
• LogP: 0.10030
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 462.11621151
• Heavy Atom Count: 33
• Complexity: 744

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)O)O

Technology Process of 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

There total 4 articles about 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one 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: 53.0%

C16H14O7 + UDP-glucose → 3'-methoxy-5,7,4'-trihydroxyflavone 6-C-β-D-glucopyranoside (20013-23-4) + chrysoeriol 8-C-glucoside (301-16-6)

Guidance literature:

With recombinant Oryza sativa C-glycosyltransferase; In ethanol; at 30 ℃; pH=7.5; Enzymatic reaction;

DOI:10.1016/j.phytochem.2016.02.013

Reference yield:

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone (18065-05-9) → 3'-methoxy-5,7,4'-trihydroxyflavone 6-C-β-D-glucopyranoside (20013-23-4) + chrysoeriol 8-C-glucoside (301-16-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / Reflux

2: potassium hydroxide / pyridine / 1 h / 85 °C / Inert atmosphere

3: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran

4: recombinant Oryza sativa C-glycosyltransferase / ethanol / 30 °C / pH 7.5 / Enzymatic reaction

With dmap; palladium 10% on activated carbon; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; 2: |Baker-Venkataraman Rearrangement;

DOI:10.1016/j.phytochem.2016.02.013

Reference yield:

C30H26O7 → 3'-methoxy-5,7,4'-trihydroxyflavone 6-C-β-D-glucopyranoside (20013-23-4) + chrysoeriol 8-C-glucoside (301-16-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide / pyridine / 1 h / 85 °C / Inert atmosphere

2: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran

3: recombinant Oryza sativa C-glycosyltransferase / ethanol / 30 °C / pH 7.5 / Enzymatic reaction

With palladium 10% on activated carbon; hydrogen; potassium hydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; 1: |Baker-Venkataraman Rearrangement;

DOI:10.1016/j.phytochem.2016.02.013

upstream raw materials:

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

Downstream raw materials:

2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-8-(tetra-O-methyl-β-D-glucopyranosyl)-chromen-4-one

Refernces