4-METHYLESCULETIN

Base Information

• Chemical Name: 4-METHYLESCULETIN
• CAS No.: 529-84-0
• Molecular Formula: C10H8 O4
• Molecular Weight: 192.171
• Hs Code.: 2932209090
• European Community (EC) Number: 208-470-0
• NSC Number: 688807,11828
• UNII: 132H8N0A91
• DSSTox Substance ID: DTXSID6060187
• Nikkaji Number: J11.701C
• Wikidata: Q27251461
• Metabolomics Workbench ID: 74231
• ChEMBL ID: CHEMBL313244
• Mol file: 529-84-0.mol

Synonyms:Coumarin,6,7-dihydroxy-4-methyl- (7CI,8CI); Esculetin, 4-methyl- (6CI);4-Methyl-6,7-dihydroxycoumarin; 4-Methylaesculetin; 4-Methylesculetin;4-Methylesculetol; 6,7-Dihydroxy-4-methylcoumarin; Methylesculetin; NSC 11828;NSC 688807

Chemical Property of 4-METHYLESCULETIN

Chemical Property:

• Appearance/Colour: Yellow needle crystal
• Vapor Pressure: 6.46E-09mmHg at 25°C
• Melting Point: 274-276 °C(lit.)
• Refractive Index: 1.4440 (estimate)
• Boiling Point: 455.5 °C at 760 mmHg
• PKA: 8.72(at 25℃)
• Flash Point: 190.7 °C
• PSA: 70.67000
• Density: 1.456 g/cm³
• LogP: 1.51260
• Storage Temp.: 2-8°C
• Solubility.: DMF: soluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 192.04225873
• Heavy Atom Count: 14
• Complexity: 284

Purity/Quality:

99% ^*data from raw suppliers

6,7-Dihydroxy-4-methylcoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=CC(=C(C=C12)O)O
• Uses: 6,7-Dihydroxy-4-methylcoumarin is suitable as a pH-indicator.

Technology Process of 4-METHYLESCULETIN

There total 26 articles about 4-METHYLESCULETIN 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: 97.0%

1,2,4-Trihydroxybenzene (533-73-3) + ethyl acetoacetate (141-97-9) → 6,7-dihydroxy-4-methylcoumarin (529-84-0)

Guidance literature:

With trifluoroacetic acid; at 100 ℃; for 0.5h; regioselective reaction; Microwave irradiation;

DOI:10.1002/chem.201201039

Reference yield: 90.0%

1,2,4-triacetoxybenzene (613-03-6) + ethyl acetoacetate (141-97-9) → 6,7-dihydroxy-4-methylcoumarin (529-84-0)

Guidance literature:

In water; at 80 ℃; for 0.5h;

DOI:10.1002/ejoc.201901894

Reference yield: 82.0%

4-Oxo-pentanoic acid 4-methyl-2-oxo-7-(4-oxo-pentanoyloxy)-2H-chromen-6-yl ester (116577-51-6) → 6,7-dihydroxy-4-methylcoumarin (529-84-0)

Guidance literature:

With sodium metabisulfite; sodium thiosulfate; In tetrahydrofuran; water; for 0.5h; Product distribution; Ambient temperature; deprotection;

DOI:10.1246/cl.1988.585

upstream raw materials:

4-methyleneoxetan-2-one

1,2,4-Trihydroxybenzene

7-hydroxy-4-methyl-chromen-2-one

6-hydroxy-7-methoxyl-4-methylcoumarin

Downstream raw materials:

4-methyl-6,7-bis-(2-sulfo-benzoyloxy)-coumarin

7-benzyloxy-6-hydroxy-4-methyl-coumarin

6,7-bis-(2-diethylamino-ethoxy)-4-methyl-coumarin

6-hydroxy-4-methyl-7-(toluene-4-sulfonyloxy)-coumarin

Refernces

• 1、 Castro, María Eugenia,Durand-Niconoff, J. Sergio,Fernández-Pomares, Cynthia,Guerrero, Tomás,Juárez-Aguilar, Enrique,Melendez, Francisco J.,Montoya-Hernández, Eva Luz,Olivares-Romero, José L.,Ortiz-Blanco, Erik,Sosa-Ortiz, Gabriela,Tovar-Miranda, Ricardo. "Mannich bases of hydroxycoumarins: Synthesis, DFT/QTAIM computational study and assessment of biological activity". . p. 31260 - 31271. Retrieved 2021/11/30.
• 2、 álvarez, José María,Jorge, Zacarías D.,Massanet, Guillermo M.. "Study of the Oxidative Cleavage Proposed in the Biogenesis of Transtaganolides/Basiliolides: Pyran-2-one Aromaticity-Mediated Regioselective Control and Biogenetic Implications". supporting information. . Retrieved 2020/03/05.