Isoscopoletin

Base Information

• Chemical Name: Isoscopoletin
• CAS No.: 776-86-3
• Molecular Formula: C10H8O4
• Molecular Weight: 192.171
• Hs Code.: 29322090
• European Community (EC) Number: 212-282-4
• DSSTox Substance ID: DTXSID40228266
• Nikkaji Number: J12.486I
• Metabolomics Workbench ID: 74305
• ChEMBL ID: CHEMBL390320
• Mol file: 776-86-3.mol

Synonyms:6-hydroxy-7-methoxycoumarin;isoscopoletin

Chemical Property of Isoscopoletin

Chemical Property:

• Vapor Pressure: 2E-07mmHg at 25°C
• Melting Point: 206-208°C
• Refractive Index: 1.609
• Boiling Point: 413.5 °C at 760 mmHg
• PKA: 8.94±0.20(Predicted)
• Flash Point: 172.4 °C
• PSA: 59.67000
• Density: 1.377 g/cm³
• LogP: 1.50720
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 192.04225873
• Heavy Atom Count: 14
• Complexity: 261

Purity/Quality:

≥98% ^*data from raw suppliers

6-Hydroxy-7-methoxycoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C=CC(=O)OC2=C1)O

Technology Process of Isoscopoletin

There total 31 articles about Isoscopoletin 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: 96.5%

6-isopropoxy-7-methoxycoumarin (139386-30-4) → isoscopoletin (776-86-3)

Guidance literature:

With sulfuric acid; In acetic acid; for 2.5h; Heating;

DOI:10.1248/cpb.40.2614

Reference yield: 89.0%

methanol (67-56-1) + aesculetin (305-01-1) → isoscopoletin (776-86-3)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 10 - 20 ℃; for 0.75h; sonication;

DOI:10.1016/j.tetlet.2003.09.114

Reference yield: 79.0%

2,5-dihydroxy-4-methoxy-benzaldehyde (29865-97-2) + acetyl chloride (75-36-5) → isoscopoletin (776-86-3)

Guidance literature:

acetyl chloride; With sodium acetate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 0.166667h;

2,5-dihydroxy-4-methoxy-benzaldehyde; In N,N-dimethyl-formamide; at 180 ℃; for 2h;

upstream raw materials:

diazomethane

aesculetin

7-methoxycoumarin

6-acetoxy-7-methoxy-chromen-2-one

Downstream raw materials:

6-(3,3-dimethylallyloxy)-7-methoxycoumarin

Scoparone

aesculetin

6-geranyloxy-7-methoxycoumarin

Refernces

• 1、 Dikhtyarev, V. I.,Kovalev, V. N.,Komissarenko, N. F.. "HYDROXYCOUMARINS OF Phaseolus vulgaris". . p. 363 - 364. Retrieved 1983.
• 2、 -. "High-selectivity preparation method for 7-methoxy-6/8-hydroxy coumarin". Paragraph 0028; 0029; 0030. . Retrieved 2017/08/28.
• 3、 Khunnawutmanotham, Nisachon,Chimnoi, Nitirat,Saparpakorn, Patchreenart,Techasakul, Supanna. "Synthesis and anti-acetylcholinesterase activity of scopoletin derivatives". . p. 137 - 145. Retrieved 2016/03/09.