2-(3-Hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one

Base Information

• Chemical Name: 2-(3-Hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
• CAS No.: 112448-39-2
• Molecular Formula: C₂₀H₂₀O₈
• Molecular Weight: 388.374
• UNII: 96E9T839AP
• DSSTox Substance ID: DTXSID80150057
• Nikkaji Number: J546.513C
• Wikidata: Q83015982
• Metabolomics Workbench ID: 24561
• ChEMBL ID: CHEMBL225704
• Mol file: 112448-39-2.mol

Synonyms:3'-demethylnobiletin

Chemical Property of 2-(3-Hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one

Chemical Property:

• Vapor Pressure: 1.17E-15mmHg at 25°C
• Melting Point: 170-171 °C
• Boiling Point: 613.8°C at 760 mmHg
• PKA: 9.95±0.10(Predicted)
• Flash Point: 218.8°C
• PSA: 96.59000
• Density: 1.304g/cm³
• LogP: 3.20860
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 388.11581759
• Heavy Atom Count: 28
• Complexity: 579

Purity/Quality:

≥98% ^*data from raw suppliers

3-Hydroxy-5- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)O

Technology Process of 2-(3-Hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one

There total 14 articles about 2-(3-Hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxychromen-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: 84.0%

3'-benzyloxy-4',5,6,7,8-pentamethoxyflavone (29201-99-8) → 2-(3-hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one (112448-39-2)

Guidance literature:

With 20 % Pd(OH)2/C; hydrogen; In ethanol; ethyl acetate; under 760.051 Torr;

DOI:10.1016/j.bmcl.2011.05.121

Reference yield: 23.0%

2-hydroxy-3,4,5,6-tetramethoxyacetophenone (3162-28-5) + (1H-benzo[d][1,2,3]triazol-1-yl)(3-(benzyloxy)-4-methoxyphenyl)methanone → 2-(3-hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one (112448-39-2)

Guidance literature:

2-hydroxy-3,4,5,6-tetramethoxyacetophenone; (1H-benzo[d][1,2,3]triazol-1-yl)(3-(benzyloxy)-4-methoxyphenyl)methanone; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

With trifluoroacetic acid; In tetrahydrofuran; toluene; at 60 ℃; for 0.5h; Inert atmosphere;

With 10 wt% Pd(OH)2 on carbon; hydrogen; In tetrahydrofuran; ethanol; toluene; at 60 ℃; for 2h; Inert atmosphere;

DOI:10.3987/COM-13-S(S)107

Reference yield:

2-hydroxy-3,4,5,6-tetramethoxyacetophenone (3162-28-5) → 2-(3-hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one (112448-39-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 192 mg / KOH / ethanol / 20 °C

2: H₃PO₄ / ethanol / 16 h / Heating

3: 48 mg / 2,3-dichloro-5,6-dicyanobenzoquinone / dioxane / 8 h / Heating

4: 15 mg / hydrogen / Pd/C / methanol / 0.5 h / 2068.65 Torr

With potassium hydroxide; phosphoric acid; hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol;

DOI:10.1016/j.bmc.2007.03.021

upstream raw materials:

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

3'-benzyloxy-4',5,6,7,8-pentamethoxyflavanone

2-hydroxy-3,4,5,6-tetramethoxyacetophenone

3-benzyloxy-4-methoxybenzaldehyde

Downstream raw materials:

3',5-dihydroxy-4',6,7,8-tetramethoxyflavone