Methyl-liquiritigenin

Base Information

• Chemical Name: Methyl-liquiritigenin
• CAS No.: 32274-71-8
• Molecular Formula: C16H14O4
• Molecular Weight: 270.285
• DSSTox Substance ID: DTXSID80437613
• Nikkaji Number: J1.972.842K
• Wikidata: Q82253146
• Metabolomics Workbench ID: 27227
• ChEMBL ID: CHEMBL402970
• Mol file: 32274-71-8.mol

Synonyms:Methyl-liquiritigenin;32274-71-8;4'-hydroxy-7-methoxyflavanone;2-(4-hydroxyphenyl)-7-methoxychroman-4-one;2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one;7-O-Methyl-liquiritigenin;CHEMBL402970;7-Methylliquiritigenin;D0W3LM;7-Methoxy-4?-hydroxyflavanone;DTXSID80437613;CHEBI:168012;BDBM50374257;LMPK12140062;PD179943;XM161808;2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Chemical Property of Methyl-liquiritigenin

Chemical Property:

• PSA: 55.76000
• LogP: 3.10730
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 270.08920892
• Heavy Atom Count: 20
• Complexity: 348

Purity/Quality:

99% ^*data from raw suppliers

7-O-Methyl-liquiritigenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)C(=O)CC(O2)C3=CC=C(C=C3)O

Technology Process of Methyl-liquiritigenin

There total 21 articles about Methyl-liquiritigenin 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: 93.0%

7-Methoxy-2-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chroman-4-one → 7-Methylliquiritigenin (32274-71-8)

Guidance literature:

With acetate buffer; β-glucosidase; at 37 ℃; for 12h; pH=5.0;

DOI:10.1248/cpb.50.788

Reference yield: 67.0%

4,2'-dihydroxy-4'-methoxy-trans-chalcone (63529-06-6) → 7-Methylliquiritigenin (32274-71-8)

Guidance literature:

With sulfuric acid; In methanol; for 7h; Heating;

DOI:10.1023/A:1014490817731

Reference yield: 35.0%

1-(2-hydroxy-4-methoxyphenyl)ethanone (552-41-0) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → 7-Methylliquiritigenin (32274-71-8)

Guidance literature:

With piperidine; In benzene; Heating;

DOI:10.1016/j.bmcl.2006.08.126

upstream raw materials:

(R)-2-(4-β-D-glucopyranosyloxy-phenyl)-7-methoxy-chroman-4-one

4,2'-dihydroxy-4'-methoxy-trans-chalcone

(S)-2-(4-β-D-glucopyranosyloxy-phenyl)-7-methoxy-chroman-4-one

(E)‐3‐(4‐hydroxyphenyl)‐1‐(2,4‐dimethoxyphenyl)prop‐2‐en‐1‐one

Downstream raw materials:

4,4'-dimethoxystilbene

4-{4-[bis-(4-methoxy-phenyl)-methylene]-7-methoxy-chroman-2-yl}-phenol

1,1,2,2-tetrakis(4-methoxyphenyl)ethene

3,4'-Bis-benzyloxystilben

Refernces

• 1、 Gupta, Atul,Dwivedy, Anila,Keshri, Govind,Sharma, Ramesh,Balapure, Anil Kumar,Singh, Man Mohan,Ray, Suprabhat. "Rapid synthesis of 4-benzylidene and 4-[bis-(4-methoxyphenyl)-methylene-2-substituted phenyl-benzopyrans as potential selective estrogen receptor modulators (SERMs) using McMurry coupling reaction". . p. 6006 - 6012. Retrieved 2007/10/03.
• 2、 Pouget,Fagnere,Basly,Besson,Champavier,Habrioux,Chulia. "Synthesis and aromatase inhibitory activity of flavanones". . p. 286 - 291. Retrieved 2007/10/03.