Bergaptol

Base Information

• Chemical Name: Bergaptol
• CAS No.: 486-60-2
• Molecular Formula: C11H6 O4
• Molecular Weight: 202.166
• European Community (EC) Number: 803-802-6
• NSC Number: 341958
• UNII: KTC8ANI30F
• DSSTox Substance ID: DTXSID40197564
• Nikkaji Number: J12.566K
• Wikipedia: Bergaptol
• Wikidata: Q3638533
• Metabolomics Workbench ID: 42474
• ChEMBL ID: CHEMBL242711
• Mol file: 486-60-2.mol

Synonyms:4-Hydroxy-7H-furo(3,2-g)chromen-7-one;bergaptol

Chemical Property of Bergaptol

Chemical Property:

• Vapor Pressure: 0.000299mmHg at 25°C
• Melting Point: 287-290°C
• Boiling Point: 311.9°Cat760mmHg
• PKA: 6.80±0.20(Predicted)
• Flash Point: 142.4°C
• PSA: 63.58000
• Density: 1.526g/cm³
• LogP: 2.24480
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 202.02660867
• Heavy Atom Count: 15
• Complexity: 312

Purity/Quality:

≥98% ^*data from raw suppliers

Bergaptol ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)OC2=CC3=C(C=CO3)C(=C21)O
• Uses: A hydroxylated psoralen that acts as a potent inhibitors of debenzylation activity of CYP3A4 enzyme with an IC50 value of 24.92 and 42.93 μM, respectively. Recent studies suggest that it may have antiproliferative and anticancer properties.

Technology Process of Bergaptol

There total 15 articles about Bergaptol 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: 98.4%

bergapten (484-20-8) → bergaptol (486-60-2)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere; Cooling with ice;

Reference yield:

tortuosin (89787-38-2) → bergaptol (486-60-2) + 5-geranyloxypsoralen (23930-02-1)

Guidance literature:

With sulfuric acid; In ethanol; at 80 ℃; for 6h;

DOI:10.1007/BF00575164

Reference yield:

→ bergaptol (486-60-2)

Guidance literature:

With acetic acid; at 120 ℃;

upstream raw materials:

3,4,6-triacetoxy-2,3-dihydro-benzofuran

bergamottin

isoimperatorin

Notopterol

Downstream raw materials:

isoimperatorin

bergamottin

5-benzyloxypsoralen

oxypeucedanin hydrate

Refernces

• 1、 Schoenberg,Aziz. "-". . p. 2563. Retrieved 1955.
• 2、 -. "AChE/BACE1/GSK-3beta three-target inhibitor, preparation method thereof and application of AChE/BACE1/GSK-3beta three-target inhibitor in resisting Alzheimer disease". Paragraph 0060-0063. . Retrieved 2021/08/07.
• 3、 Marumoto, Shinsuke,Miyazawa, Mitsuo. "Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor". supporting information; experimental part. p. 784 - 788. Retrieved 2012/03/22.