5,4'-Dihydroxy-3,6,7,8,3'-pentamethoxyflavone

Base Information

• Chemical Name: 5,4'-Dihydroxy-3,6,7,8,3'-pentamethoxyflavone
• CAS No.: 50439-47-9
• Molecular Formula: C₂₀H₂₀O₉
• Molecular Weight: 404.373
• Hs Code.: 2914509090
• NSC Number: 333051
• UNII: PYF99PJ2WQ
• DSSTox Substance ID: DTXSID60198477
• Nikkaji Number: J356.637D
• Wikidata: Q83071246
• Metabolomics Workbench ID: 26423
• ChEMBL ID: CHEMBL59220
• Mol file: 50439-47-9.mol

Synonyms:5,4'-dihydroxy-3,6,7,8,3'-pentamethoxyflavone;5,4'-diOH-3,6,7,8,3'-PMF

Chemical Property of 5,4'-Dihydroxy-3,6,7,8,3'-pentamethoxyflavone

Chemical Property:

• Vapor Pressure: 5.81E-18mmHg at 25°C
• Boiling Point: 658.8°C at 760 mmHg
• Flash Point: 234.8°C
• PSA: 116.82000
• Density: 1.44g/cm³
• LogP: 2.91420
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 404.11073221
• Heavy Atom Count: 29
• Complexity: 621

Purity/Quality:

99% ^*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=C(C(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)OC)O

Technology Process of 5,4'-Dihydroxy-3,6,7,8,3'-pentamethoxyflavone

There total 12 articles about 5,4'-Dihydroxy-3,6,7,8,3'-pentamethoxyflavone 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-(4-Benzyloxy-3-methoxy-phenyl)-5-hydroxy-3,6,7,8-tetramethoxy-chromen-4-one (173217-68-0) → 5,4′-dihydroxy-3,6,7,8,3′-pentamethoxyflavone (50439-47-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate;

DOI:10.1248/cpb.43.2054

Reference yield:

3-methoxy-4-benzyloxybenzoyl chloride (1486-52-8) → 5,4′-dihydroxy-3,6,7,8,3′-pentamethoxyflavone (50439-47-9)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / 2 h / 60 - 80 °C

2: KOH, pyridine / 2 h / 60 - 70 °C

3: H₂SO₄, AcOH / 1 h / 50 °C

4: 100 percent / N,N-diisopropylethylamine / CH₂Cl₂

5: 1.) dimethyldioxirane, 2.) TsOH / 1.) acetone, CH₂Cl₂, 0 deg C, 12 h, 2.) CH₂Cl₂, 0 deg C, 20 min

6: conc. HCl / acetic acid / 2 h / Ambient temperature

7: K₂CO₃ / acetone / Heating

8: AlBr₃ / acetonitrile / 0.67 h / 0 °C

9: H₂ / 10percent Pd/C / methanol; ethyl acetate

With pyridine; hydrogenchloride; potassium hydroxide; aluminum tri-bromide; sulfuric acid; hydrogen; 3,3-dimethyldioxirane; potassium carbonate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; ethyl acetate; acetone; acetonitrile;

DOI:10.1248/cpb.43.2054

Reference yield:

2',5'-dihydroxy-3',4',6'-trimethoxyacetophenone (55742-65-9) → 5,4′-dihydroxy-3,6,7,8,3′-pentamethoxyflavone (50439-47-9)

Guidance literature:

Multi-step reaction with 10 steps

1: N,N-diisopropylethylamine / CH₂Cl₂ / 4 h / Ambient temperature

2: pyridine / 2 h / 60 - 80 °C

3: KOH, pyridine / 2 h / 60 - 70 °C

4: H₂SO₄, AcOH / 1 h / 50 °C

5: 100 percent / N,N-diisopropylethylamine / CH₂Cl₂

6: 1.) dimethyldioxirane, 2.) TsOH / 1.) acetone, CH₂Cl₂, 0 deg C, 12 h, 2.) CH₂Cl₂, 0 deg C, 20 min

7: conc. HCl / acetic acid / 2 h / Ambient temperature

8: K₂CO₃ / acetone / Heating

9: AlBr₃ / acetonitrile / 0.67 h / 0 °C

10: H₂ / 10percent Pd/C / methanol; ethyl acetate

With pyridine; hydrogenchloride; potassium hydroxide; aluminum tri-bromide; sulfuric acid; hydrogen; 3,3-dimethyldioxirane; potassium carbonate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; ethyl acetate; acetone; acetonitrile;

DOI:10.1248/cpb.43.2054

upstream raw materials:

2-(4-Benzyloxy-3-methoxy-phenyl)-5-hydroxy-3,6,7,8-tetramethoxy-chromen-4-one

3-methoxy-4-benzyloxybenzoyl chloride

2',5'-dihydroxy-3',4',6'-trimethoxyacetophenone

1-(2-Hydroxy-3,4,6-trimethoxy-5-methoxymethoxy-phenyl)-ethanone

Refernces

• 1、 Rao,Nair,Pratap. "Induction of mutations by thioridazine hydrochloride, an active ingredient of Mellaril.". . p. 403 - 404. Retrieved 2007/10/08.