Cerasidin

Base Information

• Chemical Name: Cerasidin
• CAS No.: 64200-22-2
• Molecular Formula: C₁₉H₂₀O₆
• Molecular Weight: 344.364
• ChEMBL ID: CHEMBL3393847
• DSSTox Substance ID: DTXSID50554760
• Metabolomics Workbench ID: 26761
• Nikkaji Number: J754.135J
• Wikidata: Q76423548
• Mol file: 64200-22-2.mol

Synonyms:Cerasidin;64200-22-2;(E)-3-(2,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one;2'-HYDROXY-2,4,4',6'-TETRAMETHOXYCHALCONE;CHEMBL3393847;SCHEMBL10849424;DTXSID50554760;CHEBI:193472;IAUDUEQNUVKNBT-SOFGYWHQSA-N;LMPK12120285;(2E)-3-(2,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one;CS-0454503;AR-683/43306439;2'-Hydroxy-2,4,4',6'-tetramethoxychalcone, AldrichCPR;3-(2,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-2-propen-1-one;2-Propen-1-one, 3-(2,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-

Chemical Property of Cerasidin

Chemical Property:

• PSA: 74.22000
• LogP: 3.32270
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 344.12598835
• Heavy Atom Count: 25
• Complexity: 451

Purity/Quality:

98% ^*data from raw suppliers

Cerasidin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)C=CC(=O)C2=C(C=C(C=C2OC)OC)O)OC
• Isomeric SMILES: COC1=CC(=C(C=C1)/C=C/C(=O)C2=C(C=C(C=C2OC)OC)O)OC
• Uses: Cerasidin has the general structure of chalcones (aromatic ketone and enone), and are important biological compounds. Due to this, Cerasidin has been used for cytotoxic studies, and studies involving α7 acetylcholine nicotine receptors as a possible positive allosteric modulators with other chalcone structures.

Technology Process of Cerasidin

There total 4 articles about Cerasidin 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: 68.0%

2-hydroxy-4,6-dimethoxyacetophenone (90-24-4) + 2,4-Dimethoxybenzaldehyde (613-45-6) → (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one (64200-22-2,76583-07-8)

Guidance literature:

2-hydroxy-4,6-dimethoxyacetophenone; With sodium hydroxide; In methanol; at 0 ℃; for 0.5h; Inert atmosphere;

2,4-Dimethoxybenzaldehyde; In methanol; Inert atmosphere;

DOI:10.1016/j.ejmech.2020.112216

Reference yield:

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) → (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one (64200-22-2,76583-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / acetone / 60 °C

1.2: 1 h / 60 °C

2.1: sodium hydroxide / methanol / 0.5 h / 0 °C / Inert atmosphere

2.2: Inert atmosphere

With potassium carbonate; sodium hydroxide; In methanol; acetone;

DOI:10.1016/j.ejmech.2020.112216

Reference yield:

3,5-dihydroxyphenol (108-73-6) → (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one (64200-22-2,76583-07-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: boron trifluoride diethyl etherate / 50 °C / Inert atmosphere

2.1: potassium carbonate / acetone / 60 °C

2.2: 1 h / 60 °C

3.1: sodium hydroxide / methanol / 0.5 h / 0 °C / Inert atmosphere

3.2: Inert atmosphere

With boron trifluoride diethyl etherate; potassium carbonate; sodium hydroxide; In methanol; acetone;

DOI:10.1016/j.ejmech.2020.112216

upstream raw materials:

2-hydroxy-4,6-dimethoxyacetophenone

2,4-Dimethoxybenzaldehyde

3,5-dihydroxyphenol

2,4,6-trihydroxyacetophenone

Downstream raw materials:

(E)-1-(3-bromo-2-hydroxyl-4,6-dimethoxyphenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one

2-(2,4-dimethoxy-benzylidene)-4,6-dimethoxy-benzofuran-3-one

2-(2,4-dimethoxy-phenyl)-5,7-dimethoxy-chroman-4-one

2-(2,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-chromen-4-one