3',6'-Dihydroxy-2',4,4'-trimethoxy-chalcone

Base Information

• Chemical Name: 3',6'-Dihydroxy-2',4,4'-trimethoxy-chalcone
• CAS No.: 93993-77-2
• Molecular Formula: C18H18O6
• Molecular Weight: 330.337
• NSC Number: 75340
• DSSTox Substance ID: DTXSID10418238
• Nikkaji Number: J2.029.929K,J2.790.397E
• Wikidata: Q27148469
• Mol file: 93993-77-2.mol

Synonyms:3',6'-Dihydroxy-2',4,4'-trimethoxy-chalcone;93993-77-2;(E)-1-(3,6-dihydroxy-2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one;1-(3,6-Dihydroxy-2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one;CHEBI:79421;DTXSID10418238;NSC75340;NSC-75340;3',6'-Dihydroxy-2',4,4'-trimethoxychalcone;Q27148469;(2E)-1-(3,6-dihydroxy-2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one;(E)-1-(2,4-Dimethoxy-3,6-dihydroxyphenyl)-3-(4-methoxyphenyl)-2-propene-1-one

Chemical Property of 3',6'-Dihydroxy-2',4,4'-trimethoxy-chalcone

Chemical Property:

• Vapor Pressure: 3.43E-14mmHg at 25°C
• Boiling Point: 583°C at 760 mmHg
• Flash Point: 213.3°C
• Density: 1.276g/cm³
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 330.11033829
• Heavy Atom Count: 24
• Complexity: 429

Purity/Quality:

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=C2O)OC)O)OC
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C/C(=O)C2=C(C(=C(C=C2O)OC)O)OC

Technology Process of 3',6'-Dihydroxy-2',4,4'-trimethoxy-chalcone

There total 5 articles about 3',6'-Dihydroxy-2',4,4'-trimethoxy-chalcone 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: 90.0%

3,6-dihydroxy-2,4-dimethoxyacetophenone (6962-57-8) + 4-methoxy-benzaldehyde (123-11-5) → 1-(3,6-dihydroxy-2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-propenone (93993-77-2)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.3184/174751917X14873588907765

Reference yield: 76.0%

2'-hydroxy-4,4',6'-trimethoxychalcone (3420-72-2,37951-13-6,64680-84-8) → 1-(2,5-dihydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)propenone (93993-77-2)

Guidance literature:

With 3,3-dimethyldioxirane; In dichloromethane; acetone; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.tet.2004.01.023

Reference yield:

2,6-dimethoxy-p-quinone (530-55-2,26547-64-8) → 1-(3,6-dihydroxy-2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-propenone (93993-77-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium dithionite / water / 20 °C

2: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 20 - 80 °C

3: potassium hydroxide / methanol / 72 h / 20 °C / Inert atmosphere

With sodium dithionite; boron trifluoride diethyl etherate; potassium hydroxide; In methanol; water; 1,2-dichloro-ethane; 2: |Friedel-Crafts Acylation / 3: |Claisen-Schmidt Condensation;

DOI:10.3184/174751917X14873588907765

upstream raw materials:

3,6-dihydroxy-2,4-dimethoxyacetophenone

4-methoxy-benzaldehyde

4-(acetyloxy)-3,5-dimethoxyphenyl acetate

2,6-dimethoxy-p-quinone

Downstream raw materials:

6-hydroxy-5,7-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-methoxyphenyl)propenone

tangeritin

5,8-dihydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone