(2R,3S)-2,4',7-trihydroxyisoflavanone

Base Information

• Chemical Name: (2R,3S)-2,4',7-trihydroxyisoflavanone
• CAS No.: 131887-80-4
• Molecular Formula: C15H12O5
• Molecular Weight: 272.257
• DSSTox Substance ID: DTXSID001143009
• Metabolomics Workbench ID: 62769
• Wikidata: Q27132602
• Mol file: 131887-80-4.mol

Synonyms:(2R,3S)-2,4',7-trihydroxyisoflavanone;(2R,3S)-2,7-dihydroxy-3-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one;CHEBI:63325;DTXSID001143009;131887-80-4;Q27132602;(2R,3S)-2,7-dihydroxy-3-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one;(2R,3S)-2,3-Dihydro-2,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Chemical Property of (2R,3S)-2,4',7-trihydroxyisoflavanone

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 272.06847348
• Heavy Atom Count: 20
• Complexity: 363

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2C(OC3=C(C2=O)C=CC(=C3)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1[C@H]2[C@@H](OC3=C(C2=O)C=CC(=C3)O)O)O

Technology Process of (2R,3S)-2,4',7-trihydroxyisoflavanone

There total 2 articles about (2R,3S)-2,4',7-trihydroxyisoflavanone 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:

7,4'-dihydroxy-dihydroflavone (69097-97-8,41680-09-5) → daidzein (486-66-8) + (2R,3S)-2,7,4'-trihydroxyisoflavanone (131887-80-4)

Guidance literature:

With NADPH; at 30 ℃; for 0.75h; Mechanism; cytochrome P-450; other substrates, effect of detergents;

DOI:10.1016/S0040-4020(01)86489-9

Reference yield:

liquiritigenin (578-86-9,41680-09-5) → (2R,3S)-2,7,4'-trihydroxyisoflavanone (131887-80-4)

Guidance literature:

2-hydroxyisoflavanone synthase;

DOI:10.1016/j.phytochem.2006.09.010

Reference yield:

(2R,3S)-2,7,4'-trihydroxyisoflavanone (131887-80-4) → medicarpin (32383-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2-methoxyethanol / 2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase

2: 2-hydroxyisoflavanone dehydratase

With 2-methoxy-ethanol; 2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase; 2-hydroxyisoflavanone dehydratase;

DOI:10.1016/j.phytochem.2006.09.010

upstream raw materials:

7,4'-dihydroxy-dihydroflavone

liquiritigenin

Downstream raw materials:

2,7-dihydroxy-4'-methoxyisoflavanone

daidzein

medicarpin

7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on