Isopimpinellin

Base Information

• Chemical Name: Isopimpinellin
• CAS No.: 482-27-9
• Molecular Formula: C₁₃H₁₀O₅
• Molecular Weight: 246.219
• Hs Code.: 2932202000
• European Community (EC) Number: 639-076-0
• NSC Number: 401288,217988
• UNII: 20GCF755G6
• DSSTox Substance ID: DTXSID30197457
• Nikkaji Number: J5.787H
• Wikipedia: Isopimpinellin
• Wikidata: Q6086206
• NCI Thesaurus Code: C63673
• Pharos Ligand ID: L1P87R94GCQJ
• Metabolomics Workbench ID: 46480
• ChEMBL ID: CHEMBL140796
• Mol file: 482-27-9.mol

Synonyms:5,8-dimethoxypsoralen;isopimpinellin

Chemical Property of Isopimpinellin

Chemical Property:

• Vapor Pressure: 3.05E-08mmHg at 25°C
• Melting Point: 150-151°C
• Boiling Point: 448.7°Cat760mmHg
• Flash Point: 225.1°C
• PSA: 61.81000
• Density: 1.352g/cm³
• LogP: 2.55640
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 246.05282342
• Heavy Atom Count: 18
• Complexity: 366

Purity/Quality:

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

Isopimpinellin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison by ingestion.
• Hazard Codes: T+
• Statements: 20/21/22-28
• Safety Statements: 22-36/37/39-45-36/37-28

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)OC
• Description: Psoralens are natural photoactivable compounds in plants and can cause phototoxic contact dermatitis. For example, Cachrys libanotis contains 5,8-dimethoxypsoralen.
• Uses: Antiviral, anti HIV antineoplastic, antifungal, insect antifeedant

Technology Process of Isopimpinellin

There total 8 articles about Isopimpinellin 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: 82.0%

5,8-dihydroxypsoralen (14348-23-3) + methyl iodide (74-88-4) → isopimpinellin (482-27-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 1h; Reflux; Inert atmosphere;

DOI:10.1016/j.bmc.2011.12.002

Reference yield:

9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one (298-81-7) → isopimpinellin (482-27-9)

Guidance literature:

Multi-step reaction with 3 steps

1: chromium (VI)-oxide; aqueous acetic acid

2: water; sulfur dioxide

3: acetone; potassium carbonate

With chromium(VI) oxide; sulfur dioxide; water; potassium carbonate; acetic acid; acetone;

DOI:10.1021/jo01086a020

Reference yield:

furo<3,2-g><1>benzopyran-4,7,9-trione (483-36-3) → isopimpinellin (482-27-9)

Guidance literature:

Multi-step reaction with 2 steps

1: water; sulfur dioxide

2: acetone; potassium carbonate

With sulfur dioxide; water; potassium carbonate; acetone;

DOI:10.1021/jo01086a020

upstream raw materials:

diazomethane

5,8-dihydroxypsoralen

5-methoxy-8-hydroxy psoralen

dimethyl sulfate

Downstream raw materials:

3-(6-Benzyloxy-4,7-dimethoxy-2,3-dihydro-benzofuran-5-yl)-propionic acid 3-methyl-but-2-enyl ester

4,6-Dihydroxy-2,5-dimethoxy-benzene-1,3-dicarbaldehyde

Refernces

• 1、 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.
• 2、 Abu Mustafa,El Bay,El Khrisy,Fayez. "Natural coumarins. XIV. Synthesis of some isoprenyl ethers of psoralene hydroquinone and related products". . p. 443 - 446. Retrieved 2007/10/08.