3-hydroxy-5,6,7,8,4′-pentamethoxyflavone

Base Information

• Chemical Name: 3-hydroxy-5,6,7,8,4′-pentamethoxyflavone
• CAS No.: 50461-91-1
• Molecular Formula: C₂₀H₂₀O₈
• Molecular Weight: 388.374
• Mol file: 50461-91-1.mol

Synonyms:3-hydroxy-5,6,7,8,4′-pentamethoxyflavone

Chemical Property of 3-hydroxy-5,6,7,8,4′-pentamethoxyflavone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-hydroxy-5,6,7,8,4′-pentamethoxyflavone

There total 14 articles about 3-hydroxy-5,6,7,8,4′-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: 67.0%

tangeritin (481-53-8) → 3-hydroxy-5,6,7,8,4′-pentamethoxyflavone (50461-91-1)

Guidance literature:

With potassium hydrogensulfate; sodium hydrogencarbonate; sodium carbonate; In dichloromethane; water; acetone; at 5 ℃; for 24h;

DOI:10.3184/174751914X13966139490181

Reference yield:

Toluene-4-sulfonic acid 5,6,7,8-tetramethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl ester (173217-41-9) → 3-hydroxy-5,6,7,8,4′-pentamethoxyflavone (50461-91-1)

Guidance literature:

With potassium carbonate; In methanol; for 2h; Heating;

DOI:10.1248/cpb.43.2054

Reference yield:

2',5'-dihydroxy-3',4',6'-trimethoxyacetophenone (55742-65-9) → 3-hydroxy-5,6,7,8,4′-pentamethoxyflavone (50461-91-1)

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: K₂CO₃ / acetone / Heating

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

9: K₂CO₃ / acetone / 0.25 h / Heating

10: K₂CO₃ / methanol / 2 h / Heating

With pyridine; hydrogenchloride; potassium hydroxide; sulfuric acid; 3,3-dimethyldioxirane; potassium carbonate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetic acid; acetone;

DOI:10.1248/cpb.43.2054

upstream raw materials:

Toluene-4-sulfonic acid 5,6,7,8-tetramethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl ester

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

6-hydroxy-4',5,7,8-tetramethoxyflavone

5,7,8-Trimethoxy-6-methoxymethoxy-2-(4-methoxy-phenyl)-chromen-4-one

Downstream raw materials:

3,5,6,7,8,4′-hexamethoxyflavone

5-hydroxy-3,6,7,8,4′-pentamethoxyflavone

Refernces

• 1、 Li, Yue,Cai, Shuanglian,He, Kailin,Wang, Qiuan. "Semisynthesis of polymethoxyflavonoids from naringin and hesperidin". . p. 287 - 290. Retrieved 2014/06/09.