2-(4-Hydroxyphenyl)-3,6,8-trimethoxy-5-hydroxy-4H-1-benzopyran-4-one

Base Information

• Chemical Name: 2-(4-Hydroxyphenyl)-3,6,8-trimethoxy-5-hydroxy-4H-1-benzopyran-4-one
• CAS No.: 112667-10-4
• Molecular Formula: C18H16 O7
• Molecular Weight: 344.321
• DSSTox Substance ID: DTXSID101159675
• Nikkaji Number: J620.486D
• Wikidata: Q105113326
• Mol file: 112667-10-4.mol

Synonyms:DTXSID101159675;4',5-Dihydroxy-3,6,8-trimethoxyflavone;2-(4-Hydroxyphenyl)-3,6,8-trimethoxy-5-hydroxy-4H-1-benzopyran-4-one;5-Hydroxy-2-(4-hydroxyphenyl)-3,6,8-trimethoxy-4H-1-benzopyran-4-one;5-Hydroxy-2-(4-hydroxyphenyl)-3,6,8-trimethoxy-4H-chromen-4-one #;112667-10-4

Chemical Property of 2-(4-Hydroxyphenyl)-3,6,8-trimethoxy-5-hydroxy-4H-1-benzopyran-4-one

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 344.08960285
• Heavy Atom Count: 25
• Complexity: 524

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C2C(=C1O)C(=O)C(=C(O2)C3=CC=C(C=C3)O)OC)OC

Technology Process of 2-(4-Hydroxyphenyl)-3,6,8-trimethoxy-5-hydroxy-4H-1-benzopyran-4-one

There total 2 articles about 2-(4-Hydroxyphenyl)-3,6,8-trimethoxy-5-hydroxy-4H-1-benzopyran-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: 80.0%

4'-benzyloxy-5-hydroxy-3,6,8-trimethoxyflavone (160206-84-8) → 5,4'-dihydroxy-3,6,8-trimethoxyflavone (112667-10-4)

Guidance literature:

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

DOI:10.1016/S0031-9422(00)89555-2

Reference yield:

2'-hydroxy-3',5',6'-trimethoxyacetophenone (72424-28-3) → 5,4'-dihydroxy-3,6,8-trimethoxyflavone (112667-10-4)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 1 h / 100 °C

2: 1.) KOH, 2.) conc. H₂SO₄ / 1) pyridine, 80 deg C, 1 h; 2) HOAc, 60 deg C, 10 min

3: 1.) dimethyldioxirane, 2.) TsOH / 1) acetone, Ch₂Cl₂, -20 - -10 deg C, 12 h; 2) CH₂Cl₂, 0 deg C, 40 - 50 min

4: 87 percent / K₂CO₃ / acetone

5: 83 percent / AlBr₃ / acetonitrile / 1 h / 0 °C

6: 80 percent / H₂ / Pd-C / methanol; ethyl acetate

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

DOI:10.1016/S0031-9422(00)89555-2

Reference yield:

acetic anhydride (108-24-7) + 5,4'-dihydroxy-3,6,8-trimethoxyflavone (112667-10-4) → Acetic acid 2-(4-acetoxy-phenyl)-3,6,8-trimethoxy-4-oxo-4H-chromen-5-yl ester (112667-13-7)

Guidance literature:

In pyridine; at 30 ℃; for 24h;

DOI:10.1016/S0040-4020(01)83467-0

upstream raw materials:

4'-benzyloxy-5-hydroxy-3,6,8-trimethoxyflavone

2'-hydroxy-3',5',6'-trimethoxyacetophenone

Downstream raw materials:

Acetic acid 2-(4-acetoxy-phenyl)-3,6,8-trimethoxy-4-oxo-4H-chromen-5-yl ester