(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone

Base Information

• Chemical Name: (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone
• CAS No.: 107585-77-3
• Molecular Formula: C16H14O5
• Molecular Weight: 286.284
• DSSTox Substance ID: DTXSID101143264
• Nikkaji Number: J911.659A
• Wikidata: Q104995592
• Metabolomics Workbench ID: 48204
• ChEMBL ID: CHEMBL4526219
• Mol file: 107585-77-3.mol

Synonyms:107585-77-3;4'-Demethyl-3,9-dihydroeucomin;(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone;4-Demethyl-3,9-dihydroeucomin;5,7-Dihydroxy-3-(4-hydroxybenzyl)chroman-4-one;5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-2,3-dihydrochromen-4-one;CHEMBL4526219;CHEBI:174735;DTXSID101143264;AKOS032961718;FS-10114;FT-0775865;3-(4-Hydroxybenzyl)-5,7-dihydroxychroman-4-one;5,7-dihydroxy-3-(4'-hydroxybenzyl)-4-chromanone;2,3-Dihydro-5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-4H-1-benzopyran-4-one;5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-3,4-dihydro-2H-1-benzopyran-4-one

Chemical Property of (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone

Chemical Property:

• PSA: 86.99000
• LogP: 2.23740
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 286.08412354
• Heavy Atom Count: 21
• Complexity: 377

Purity/Quality:

98%min ^*data from raw suppliers

4-Demethyl-3,9-dihydroeucomin ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(=O)C2=C(C=C(C=C2O1)O)O)CC3=CC=C(C=C3)O

Technology Process of (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone

There total 4 articles about (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 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:

5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-4H-chromen-4-one (101467-70-3) → 5,7-dihydroxy-3-(4′-hydroxybenzyl)chroman-4-one (107585-77-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr;

Reference yield:

3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on (60-82-2) → 5,7-dihydroxy-3-(4′-hydroxybenzyl)chroman-4-one (107585-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / BF₃*Et₂O, methanesulfonyl chloride / dimethylformamide / 2 h / 100 °C

2: H₂ / 10percent Pd/C / methanol / 760 Torr

With boron trifluoride diethyl etherate; hydrogen; methanesulfonyl chloride; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

Reference yield:

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on (480-41-1) → 5,7-dihydroxy-3-(4′-hydroxybenzyl)chroman-4-one (107585-77-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / sodium formate, formic acid / 10percent Pd/C / propan-2-ol / 4 h / Heating

2: 80 percent / BF₃*Et₂O, methanesulfonyl chloride / dimethylformamide / 2 h / 100 °C

3: H₂ / 10percent Pd/C / methanol / 760 Torr

With formic acid; boron trifluoride diethyl etherate; hydrogen; sodium formate; methanesulfonyl chloride; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-4H-chromen-4-one

3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

Refernces