Sulfuretin

Base Information

• Chemical Name: Sulfuretin
• CAS No.: 120-05-8
• Molecular Formula: C₁₅H₁₀O₅
• Molecular Weight: 270.241
• European Community (EC) Number: 204-366-4
• UNII: M6410VY6MI
• ChEMBL ID: CHEMBL490355
• DSSTox Substance ID: DTXSID30877681
• Metabolomics Workbench ID: 53457
• Nikkaji Number: J248.702K,J796.878G
• Wikidata: Q27108357
• Mol file: 120-05-8.mol

Synonyms:3',4',6'-trihydroxyaurone;aurone sulfuretin;sulfuretin

Chemical Property of Sulfuretin

Chemical Property:

• Vapor Pressure: 2.79E-14mmHg at 25°C
• Melting Point: 295°C
• Boiling Point: 585 °C at 760 mmHg
• Flash Point: 228.8 °C
• PSA: 86.99000
• Density: 1.597 g/cm³
• LogP: 2.41960
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 270.05282342
• Heavy Atom Count: 20
• Complexity: 419

Purity/Quality:

98%,99%, ^*data from raw suppliers

Sulfuretin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=C2C(=O)C3=C(O2)C=C(C=C3)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1/C=C\2/C(=O)C3=C(O2)C=C(C=C3)O)O)O

Technology Process of Sulfuretin

There total 11 articles about Sulfuretin 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: 95.0%

(Z)-2-(3,4-dimethoxybenzylidene)-6-methoxybenzofuran-3(2H)-one (36685-46-8) → sulfuretin (100433-06-5,120-05-8)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃;

DOI:10.1002/asia.201403032

Reference yield: 85.0%

6-hydroxybenzofuran-3-one (6272-26-0) + 3,4-dihydroxybenzaldehyde (139-85-5) → sulfuretin (100433-06-5,120-05-8)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 3h; Reflux;

DOI:10.1016/j.bmcl.2016.10.072

Reference yield: 80.0%

methyl 6-hydroxybenzofuran-3(2H)-one (113739-06-3) + 3,4-dihydroxybenzaldehyde (139-85-5) → sulfuretin (100433-06-5,120-05-8)

Guidance literature:

With hydrogenchloride; In ethanol; at 0 - 60 ℃;

DOI:10.1039/c5ra06648d

upstream raw materials:

6-hydroxybenzofuran-3-one

3,4-dihydroxybenzaldehyde

sulphuretin 3'-O-β-glucopyranoside

(Z)-2-(3,4-dimethoxybenzylidene)-6-methoxybenzofuran-3(2H)-one

Downstream raw materials:

6-acetoxy-2-((Z)-3,4-diacetoxy-benzylidene)-benzofuran-3-one

2-(3,4-dihydroxybenzyl)-6-hydroxybenzofuran-3(2H)-one

Refernces

• 1、 Bdzhola, V. G.,Bilokin, Y. V.,Borysenko, I. P.,Lukashov, S. S.,Protopopov, M. V.,Prykhod'ko, A. O.,Starosyla, S. A.,Vdovin, V. S.,Yarmoluk, S. M.. "Flavone inspired discovery of benzylidenebenzofuran-3(2H)-ones (aurones) as potent inhibitors of human protein kinase CK2". supporting information. . Retrieved 2020/07/21.
• 2、 Venkateswarlu, Somepalli,Murty, Gandrotu Narasimha,Satyanarayana, Meka. ""On water" synthesis of aurones: First synthesis of 4,5,3',4',5'-pentamethoxy-6-hydroxyaurone from Smilax riparia". . p. 303 - 314. Retrieved 2017/06/19.