Cardamonin

Base Information

• Chemical Name: Cardamonin
• CAS No.: 19309-14-9
• Molecular Formula: C16H14O4
• Molecular Weight: 270.285
• Hs Code.: 29242990
• European Community (EC) Number: 663-565-8
• UNII: H8KP1OJ8JX
• DSSTox Substance ID: DTXSID201029726
• Nikkaji Number: J258.621E,J107.395H
• Wikipedia: Cardamomin
• Wikidata: Q5038242
• Pharos Ligand ID: 3SX8S4DJ2N17
• Metabolomics Workbench ID: 26721
• ChEMBL ID: CHEMBL378104
• Mol file: 19309-14-9.mol

Synonyms:2',4'-dihydroxy-6'-methoxychalcone;cardamomin;cardamonin

Chemical Property of Cardamonin

Chemical Property:

• Vapor Pressure: 5.2E-10mmHg at 25°C
• Melting Point: 199～200℃
• Refractive Index: 1.657
• Boiling Point: 484.468 °C at 760 mmHg
• PKA: 7.00±0.40(Predicted)
• Flash Point: 182.744 °C
• PSA: 66.76000
• Density: 1.283 g/cm³
• LogP: 3.00250
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 270.08920892
• Heavy Atom Count: 20
• Complexity: 346

Purity/Quality:

Cardamonin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 61-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1C(=O)C=CC2=CC=CC=C2)O)O
• Isomeric SMILES: COC1=CC(=CC(=C1C(=O)/C=C/C2=CC=CC=C2)O)O
• Description: Cardamonin (19309-14-9) inhibits NF-κB activation via inhibition of IκBα degradation and phosphorylation, IκB kinase activation and NF-κB nuclear translocation.1,2 Cardamonin displays anti-inflammatory activity in various models.3?Cell permeable.
• Uses: Cardamonin has been used as a glycogen synthase kinase 3 (GSK3) inhibitor to study its effects on β-catenin loss and gain-of-function in human preimplantation embryos.

Technology Process of Cardamonin

There total 19 articles about Cardamonin 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: 100.0%

(E)-1-(2-methoxy-4,6-bis(methoxymethoxy)phenyl)-3-phenylprop-2-en-1-one (1013662-04-8) → cardamomin (19309-14-9)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; dichloromethane; at 60 ℃;

DOI:10.1002/ejoc.201400104

Reference yield: 82.0%

C30H26O4 → cardamomin (19309-14-9)

Guidance literature:

With boron trichloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.2174/1570180817999200531162015

Reference yield: 72.0%

4,6-dihydroxy-2-methoxyacetophenone (3602-54-8) + benzaldehyde (100-52-7) → cardamomin (19309-14-9)

Guidance literature:

With thionyl chloride; In ethanol; at 0 - 20 ℃; for 4h;

DOI:10.1016/j.bioorg.2021.105043

upstream raw materials:

dimethyl sulfate

(+/-)-7-acetoxy-5-hydroxy-2-phenyl-chroman-4-one

benzaldehyde

pinocembrin

Downstream raw materials:

Uvangoletin

(E)-3-phenyl-1-(2, 4, 6-trimethoxyphenyl)prop-2-en-1-one

(2E,2'E)-1,1'-[methylenebis(2,4-dihydroxy-6-methoxy-3,1-phenylene)]bis(3-phenylprop-2-en-1-one)

Acetic acid 5-acetoxy-3-methoxy-2-(3-phenyl-propionyl)-phenyl ester

Refernces

• 1、 Yang, Junjie,Hu, Fanjie,Guo, Chengjun,Liang, Yuqing,Song, Haiying,Cheng, Kui. "Discovery of isoliquiritigenin analogues that reverse acute hepatitis by inhibiting macrophage polarization". . . Retrieved 2021/06/15.
• 2、 Thevenin, Marion,Mouray, Elisabeth,Grellier, Philippe,Dubois, Joelle. "Facile formation of methylenebis(chalcone)s through unprecedented methylenation reaction. Application to antiparasitic and natural product synthesis". . p. 2986 - 2992. Retrieved 2014/05/20.