1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone

Base Information

• Chemical Name: 1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone
• CAS No.: 58115-20-1
• Molecular Formula: C18H20O7
• Molecular Weight: 348.3472
• DSSTox Substance ID: DTXSID20570957
• Mol file: 58115-20-1.mol

Synonyms:58115-20-1;1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone;1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxypropan-1-one;DTXSID20570957

Chemical Property of 1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone

Chemical Property:

• PSA: 105.45000
• LogP: 2.39740
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 348.12090297
• Heavy Atom Count: 25
• Complexity: 418

Purity/Quality:

97% ^*data from raw suppliers

1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone ^*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)C(=O)C(C2=CC=C(C=C2)O)C(OC)OC)O)O
• Uses: Intermediate in the synthesis of Glycitein (G635400)

Technology Process of 1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone

There total 5 articles about 1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone 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: 95.0%

2-(4-Benzyloxy-phenyl)-1-(2,4-bis-benzyloxy-5-methoxy-phenyl)-3,3-dimethoxy-propan-1-one (58115-19-8) → 1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone (58115-20-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; acetone;

Reference yield: 83.0%

C32H32O7 (741283-78-3) → 1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone (58115-20-1)

Guidance literature:

With hydrogen; 5%-palladium/activated carbon; In methanol; acetone; at 20 ℃; for 12h;

Reference yield:

2,4-Dibenzyloxy-5-methoxyacetophenone (7298-22-8) → 1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone (58115-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / 50percent aq. NaOH / ethanol / 1 h / Heating

2: 90 percent / Tl(NO₃)3*3H₂O / methanol / 1 h

3: 95 percent / H₂ / Pd/C / methanol; acetone

With sodium hydroxide; hydrogen; thallium(III) nitrate; palladium on activated charcoal; In methanol; ethanol; acetone;

upstream raw materials:

2-(4-Benzyloxy-phenyl)-1-(2,4-bis-benzyloxy-5-methoxy-phenyl)-3,3-dimethoxy-propan-1-one

2,4-Dibenzyloxy-5-methoxyacetophenone

C₃₂H₃₂O₇

Downstream raw materials:

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-(4-hydroxy-phenyl)-6-methoxy-4-oxo-4H-chromen-7-yloxy]-tetrahydro-pyran-3-yl ester

glycitin

glycitein

Refernces

• 1、 Nogradi, Mihaly,Szoellosy, Aron. "Synthesis of 4′,7-dihydroxy-6-methoxyisoflavone 7-O-β-D-glucopyranoside (glycitin)". . p. 1651 - 1652. Retrieved 2007/10/03.