Gossypetin 3,8,3'-trimethyl ether

Base Information

• Chemical Name: Gossypetin 3,8,3'-trimethyl ether
• CAS No.: 14965-08-3
• Molecular Formula: C18H16 O8
• Molecular Weight: 360.32
• NSC Number: 618932
• UNII: RR3F75GKR3
• DSSTox Substance ID: DTXSID10933693
• Nikkaji Number: J94.560I
• Wikidata: Q82909522
• Metabolomics Workbench ID: 26328
• ChEMBL ID: CHEMBL1985918
• Mol file: 14965-08-3.mol

Synonyms:Gossypetin 3,8,3'-trimethyl ether;14965-08-3;RR3F75GKR3;5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,8-dimethoxychromen-4-one;5,7,4'-Trihydroxy-3,8,3'-trimethoxyflavone;Flavone, 4',5,7-trihydroxy-3,3',8-trimethoxy-;NSC 618932;NSC-618932;5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,8-dimethoxy-4H-1-benzopyran-4-one;NSC618932;UNII-RR3F75GKR3;MEGxp0_000612;CHEMBL1985918;DTXSID10933693;Gossypetin 3,3',8-trimethylether;LMPK12113245;AKOS040734292;NCI60_005668;3,3',8-Trimethoxy-4',5,7-trihydroxyflavone;4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,8-dimethoxy-;82784-42-7

Chemical Property of Gossypetin 3,8,3'-trimethyl ether

Chemical Property:

• Vapor Pressure: 2.5E-16mmHg at 25°C
• Boiling Point: 627.3°Cat760mmHg
• Flash Point: 230.4°C
• Density: 1.54g/cm³
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 360.08451746
• Heavy Atom Count: 26
• Complexity: 561

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)OC)OC)O

Technology Process of Gossypetin 3,8,3'-trimethyl ether

There total 6 articles about Gossypetin 3,8,3'-trimethyl ether 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: 59.0%

4′,7-dihydroxy-3,3′,5,8-tetramethoxyflavone (22109-96-2) → 5,7,4'-trihydroxy-3,8,3'-trimethoxyflavone (14965-08-3) + 3,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-5,8-dimethoxy-chromen-4-one (33554-57-3)

Guidance literature:

With aluminum tri-bromide; In acetonitrile; at 25 - 28 ℃; for 2h;

DOI:10.1021/jo00230a009

Reference yield:

2,4-dihydroxy-3,6,ω-trimethoxyacetophenone (42923-40-0) → 5,7,4'-trihydroxy-3,8,3'-trimethoxyflavone (14965-08-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) potassium 4-(benzyloxy)-3-methoxybenzoate, 2.) aq. KOH / 1.) 170 - 180 deg C, 8 h, 2.) methanol, acetone, water, reflux, 20 min

2: 91 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate

3: 59 percent / AlCl₃ / diethyl ether / 10 h / Heating

With potassium hydroxide; aluminium trichloride; potassium 4-(benzyloxy)-3-methoxybenzoate; hydrogen; palladium on activated charcoal; In methanol; diethyl ether; ethyl acetate;

DOI:10.1021/jo00230a009

Reference yield:

4-(benzyloxy)-3-methoxybenzoic anhydride (1592-47-8) → 5,7,4'-trihydroxy-3,8,3'-trimethoxyflavone (14965-08-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) potassium 4-(benzyloxy)-3-methoxybenzoate, 2.) aq. KOH / 1.) 170 - 180 deg C, 8 h, 2.) methanol, acetone, water, reflux, 20 min

2: 91 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate

3: 59 percent / AlCl₃ / diethyl ether / 10 h / Heating

With potassium hydroxide; aluminium trichloride; potassium 4-(benzyloxy)-3-methoxybenzoate; hydrogen; palladium on activated charcoal; In methanol; diethyl ether; ethyl acetate;

DOI:10.1021/jo00230a009

upstream raw materials:

7,4'-Diacetoxy-3,5,8,3'-tetramethoxy-flavon

4′,7-dihydroxy-3,3′,5,8-tetramethoxyflavone

2,4-dihydroxy-3,6,ω-trimethoxyacetophenone

4-(benzyloxy)-3-methoxybenzoic anhydride

Downstream raw materials:

4′,7-dihydroxy-3,3′,5,8-tetramethoxyflavone

7,4'-Diacetoxy-3,5,8,3'-tetramethoxy-flavon

4',5,7-Triacetoxy-3,3',8-trimethoxy-flavon

hexa-O-methylogossypetin

Refernces