2',4-Dihydroxy-4',6'-dimethoxychalcone

Base Information

• Chemical Name: 2',4-Dihydroxy-4',6'-dimethoxychalcone
• CAS No.: 37308-75-1
• Molecular Formula: C17H16O5
• Molecular Weight: 300.311
• UNII: 5LE8KTR6G2
• DSSTox Substance ID: DTXSID60958437
• Nikkaji Number: J17.571D,J647.134J
• Wikipedia: Flavokavain_C
• Wikidata: Q5458168
• Metabolomics Workbench ID: 26796
• ChEMBL ID: CHEMBL251958
• Mol file: 37308-75-1.mol

Synonyms:flavokawain C

Chemical Property of 2',4-Dihydroxy-4',6'-dimethoxychalcone

Chemical Property:

• Melting Point: 179-182 °C
• Boiling Point: 556.0±50.0 °C(Predicted)
• PKA: 6.91±0.40(Predicted)
• PSA: 75.99000
• Density: 1.279±0.06 g/cm3(Predicted)
• LogP: 3.01110
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 300.09977361
• Heavy Atom Count: 22
• Complexity: 387

Purity/Quality:

≥98% ^*data from raw suppliers

Flavokawain C ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C(=C1)OC)C(=O)C=CC2=CC=C(C=C2)O)O
• Isomeric SMILES: COC1=CC(=C(C(=C1)OC)C(=O)/C=C/C2=CC=C(C=C2)O)O
• Uses: Flavokawain C?is a?chalcone found in the kava plant. Studies showed that?Flavokawain C can inhibit cell cycle and promote apoptosis in HCT 116 cells. In addition, natural chalcones have been?implicated as lead compounds for developing dual inhibitors against?Histone deacetylase enzymes (HDACs) and NF-κB. Flavokawain C is a related compound Flavokawain A (F371020).

Technology Process of 2',4-Dihydroxy-4',6'-dimethoxychalcone

There total 8 articles about 2',4-Dihydroxy-4',6'-dimethoxychalcone 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: 83.0%

2’,4’-dimethoxy-6’-hydroxy-4-O-benzylchalcone (19158-99-7) → flavokawain C (37308-75-1)

Guidance literature:

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

DOI:10.2174/1570180817999200531162015

Reference yield: 70.0%

2’,4’-dimethoxy-6’-hydroxy-4-O-methoxymethylchalcone (77184-69-1) → flavokawain C (37308-75-1)

Guidance literature:

With hydrogenchloride; In methanol; water; for 0.25h; Reflux;

DOI:10.1021/np800188b

Reference yield: 51.0%

2-hydroxy-4,6-dimethoxyacetophenone (90-24-4) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → flavokawain C (37308-75-1)

Guidance literature:

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

4-hydroxy-benzaldehyde; In methanol; Inert atmosphere;

DOI:10.1016/j.ejmech.2020.112216

upstream raw materials:

helichrysetin

methyl iodide

2’,4’-dimethoxy-6’-hydroxy-4-O-methoxymethylchalcone

2-hydroxy-4,6-dimethoxyacetophenone

Downstream raw materials:

2-(4-hydroxyphenyl)-5,7-dimethoxychroman-4-one

3-(4-hydroxyphenyl)-5,7-dimethoxychromen-4-one