2'-O-Methylisoliquiritigenin

Base Information

• Chemical Name: 2'-O-Methylisoliquiritigenin
• CAS No.: 51828-10-5
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.285
• UNII: LHE9JFQ1U8
• Nikkaji Number: J641.664K,J2.786.905J
• Wikidata: Q27225760
• Metabolomics Workbench ID: 26574
• ChEMBL ID: CHEMBL253777
• Mol file: 51828-10-5.mol

Synonyms:4,4'-dihydroxy-2'-methoxychalcone;

Chemical Property of 2'-O-Methylisoliquiritigenin

Chemical Property:

• PSA: 66.76000
• LogP: 3.00250
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 270.08920892
• Heavy Atom Count: 20
• Complexity: 344

Purity/Quality:

≥98% ^*data from raw suppliers

2'-O-Methylisoliquiritigenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)O)C(=O)C=CC2=CC=C(C=C2)O
• Isomeric SMILES: COC1=C(C=CC(=C1)O)C(=O)/C=C/C2=CC=C(C=C2)O

Technology Process of 2'-O-Methylisoliquiritigenin

There total 13 articles about 2'-O-Methylisoliquiritigenin 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: 72.6%

1-(2-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone (288856-48-4) + 4-(tetrahydropyran-2-yloxy)benzaldehyde (74189-56-3) → 2'-methoxyisoliquiritigenin (51828-10-5,112408-67-0)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 ℃; for 96h;

DOI:10.5012/bkcs.2011.32.9.3459

Reference yield: 51.0%

4,4'-bis(benzyloxy)-2'-methoxychalcone → 2'-methoxyisoliquiritigenin (51828-10-5,112408-67-0)

Guidance literature:

With hydrogenchloride; In acetic acid; at 48 ℃; for 2h;

DOI:10.1016/S0031-9422(82)85049-8

Reference yield:

(E)‐3‐(4‐hydroxyphenyl)‐1‐(2,4‐dimethoxyphenyl)prop‐2‐en‐1‐one (23423-35-0) → isoliquirtigenin (961-29-5,13745-20-5) + 4,2'-dihydroxy-4'-methoxy-trans-chalcone (63529-06-6) + 2'-methoxyisoliquiritigenin (51828-10-5,112408-67-0) + 7,4'-dihydroxy-dihydroflavone (69097-97-8,41680-09-5)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide; for 3h; Further byproducts given; Heating;

DOI:10.1016/j.tetlet.2003.10.060

upstream raw materials:

1-(4-hydroxy-2-methoxy-phenyl)ethanone

4-hydroxy-benzaldehyde

isoliquirtigenin

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

Downstream raw materials:

metochalcone

Refernces

• 1、 Bianco, Armandodoriano,Cavarischia, Claudia,Farina, Angela,Guiso, Marcella,Marra, Carolina. "A new synthesis of flavonoids via Heck reaction". . p. 9107 - 9110. Retrieved 2007/10/03.
• 2、 Achenbach, Hans,Stoecker, Markus,Constenla, Manuel A.. "FLAVONOID AND OTHER CONSTITUENTS OF BAUHINIA MANCA". . p. 1835 - 1842. Retrieved 2007/10/02.