Fraxinol

Base Information

• Chemical Name: Fraxinol
• CAS No.: 486-28-2
• Molecular Formula: C11H10O5
• Molecular Weight: 222.19
• UNII: U330651DTI
• DSSTox Substance ID: DTXSID30197558
• Nikkaji Number: J12.527J
• Wikidata: Q27290621
• Metabolomics Workbench ID: 143407
• ChEMBL ID: CHEMBL611349
• Mol file: 486-28-2.mol

Synonyms:Fraxinol;486-28-2;2H-1-Benzopyran-2-one, 6-hydroxy-5,7-dimethoxy-;6-hydroxy-5,7-dimethoxychromen-2-one;UNII-U330651DTI;U330651DTI;6-hydroxy-5,7-dimethoxy-chromen-2-one;6-hydroxy-5,7-dimethoxy-2H-chromen-2-one;CHEMBL611349;SCHEMBL7133703;6-Hydroxy-5,7-dimethoxycoumarin;DTXSID30197558;HY-N2372;MFCD08693526;AKOS000278009;5,7-DIMETHOXY-6-HYDROXYCOUMARIN;AC-34035;MS-23241;COUMARIN, 6-HYDROXY-5,7-DIMETHOXY-;CS-0022552;FT-0775685;Q27290621

Chemical Property of Fraxinol

Chemical Property:

• Vapor Pressure: 1.05E-08mmHg at 25°C
• Melting Point: 170-172oC
• Refractive Index: 1.587
• Boiling Point: 449.7 °C at 760 mmHg
• PKA: 8.95±0.20(Predicted)
• Flash Point: 182.1 °C
• PSA: 68.90000
• Density: 1.358 g/cm³
• LogP: 1.51580
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 222.05282342
• Heavy Atom Count: 16
• Complexity: 301

Purity/Quality:

99%, ^*data from raw suppliers

Fraxinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=C2C=CC(=O)OC2=C1)OC)O
• Description: Fraxinol is a coumarin originally isolated from Ash tree bark. It inhibits growth of GLC-4 small cell lung carcinoma and COLO 320 colorectal cancer cells (IC50s = 193 and 165 μM, respectively). Fraxinol potentiates barbiturate-induced sleep in rats and rabbits.

Technology Process of Fraxinol

There total 7 articles about Fraxinol 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: 61.0%

3,6-dihydroxy-2,4-dimethoxybenzaldehyde (105827-22-3) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → fraxinol (486-28-2,88140-33-4)

Guidance literature:

In various solvent(s); for 4h; Heating;

DOI:10.1016/j.tet.2008.02.059

Reference yield:

→ fraxinol (486-28-2,88140-33-4)

Guidance literature:

With sulfuric acid; dihydrogen peroxide; acetic acid;

DOI:10.1021/ja01625a055

Reference yield:

6-formyllimettin (88140-31-2) → fraxinol (486-28-2,88140-33-4)

Guidance literature:

With sulfuric acid; dihydrogen peroxide; In acetic acid;

DOI:10.1248/cpb.31.3330

upstream raw materials:

Limettin

acetyl fraxinol

6-formyllimettin

mandshurin

Downstream raw materials:

5,6,7-trimethoxycoumarin

Refernces

• 1、 Maes, Dominick,Riveiro, Maria Eugenia,Shayo, Carina,Davio, Carlos,Debenedetti, Silvia,De Kimpe, Norbert. "Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins". . p. 4438 - 4443. Retrieved 2008/09/21.
• 2、 Ishii,Kobayashi,Ishikawa. "Toddalenone: A new coumarin from Toddalia asiatica (T. Aculeata). Structural establishment based on the chemical conversion of limettin into toddalenone". . p. 3330 - 3333. Retrieved 2007/10/02.