Dimethylfraxetin

Base Information

• Chemical Name: Dimethylfraxetin
• CAS No.: 6035-49-0
• Molecular Formula: C₁₂H₁₂O₅
• Molecular Weight: 236.224
• Hs Code.: 29322090
• DSSTox Substance ID: DTXSID00209112
• Nikkaji Number: J580.681J
• Wikidata: Q27164894
• Pharos Ligand ID: TBW54H4JQ48B
• Metabolomics Workbench ID: 74260
• ChEMBL ID: CHEMBL253551
• Mol file: 6035-49-0.mol

Synonyms:6,7,8-trimethoxycoumarin

Chemical Property of Dimethylfraxetin

Chemical Property:

• Vapor Pressure: 8.46E-07mmHg at 25°C
• Melting Point: 104-105°C
• Refractive Index: 1.545
• Boiling Point: 405.9 °C at 760 mmHg
• Flash Point: 183.3 °C
• PSA: 57.90000
• Density: 1.249 g/cm³
• LogP: 1.81880
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 236.06847348
• Heavy Atom Count: 17
• Complexity: 314

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Dimethylfraxetin ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 22-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=C2C(=C1)C=CC(=O)O2)OC)OC

Technology Process of Dimethylfraxetin

There total 18 articles about Dimethylfraxetin 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%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 6-hydroxy-7,8-dimethoxycoumarin (107078-01-3) → 6,7,8-trimethoxy-2H-chromen-2-one (6035-49-0)

Guidance literature:

In diethyl ether;

DOI:10.1021/np040027m

Reference yield: 86.9%

7,8-dihydroxy-6-methoxy-2H-1-benzopyran-2-one (574-84-5) + dimethyl sulfate (77-78-1) → 6,7,8-trimethoxy-2H-chromen-2-one (6035-49-0)

Guidance literature:

With potassium carbonate; In acetone; for 3h; Reflux;

DOI:10.3390/nu7031945

Reference yield: 81.0%

2-hydroxy-3,4,5-trimethoxybenzaldehyde (59481-63-9) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → 6,7,8-trimethoxy-2H-chromen-2-one (6035-49-0)

Guidance literature:

for 0.25h; Inert atmosphere; Reflux;

DOI:10.3390/molecules181215613

upstream raw materials:

diazomethane

6,7,8-trihydroxy-2H-1-benzopyran-2-one

isofraxidin

7,8-dihydroxy-6-methoxy-2H-1-benzopyran-2-one

Downstream raw materials:

2,3,4,5-tetramethoxybenzoic acid

Refernces

• 1、 Gu, Jian-Qiao,Graf, Tyler N.,Lee, Dongho,Chai, Hee-Byung,Mi, Qiuwen,Kardono, Leonardus B. S.,Setyowati, Fransisca M.,Ismail, Rachman,Riswan, Soedarsono,Farnsworth, Norman R.,Cordell, Geoffrey A.,Pezzuto, John M.,Swanson, Steven M.,Kroll, David J.,Falkinham III, Joseph O.,Wall, Monroe E.,Wani, Mansukh C.,Kinghorn, A. Douglas,Oberlies, Nicholas H.. "Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia". . p. 1156 - 1161. Retrieved 2004.
• 2、 Gao, Wenqing,Li, Qingyong,Chen, Jian,Wang, Zhichao,Hua, Changlong. "Total synthesis of six 3,4-unsubstituted coumarins". . p. 15613 - 15623. Retrieved 2014/01/17.