22980-57-0

Basic information

• Product Name: 5-methoxy-8,8-dimethyl-10-(2-methylbut-3-en-2-yl)-2H,8H-pyrano[3,2-g]chromen-2-one
• Synonyms: 10-(1,1-Dimethyl-allyl)-5-methoxy-8,8-dimethyl-8H-pyrano(3,2-g)chromen-2-one; 10-(1,1-Dimethyl-allyl)-5-methoxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-one; 2H,8H-Benzo[1,2-b:5,4-b']dipyran-2-one, 5-methoxy-8,8-dimethyl-10-(1,1-dimethyl-2-propenyl); Dentatin
• CAS NO: 22980-57-0
• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.3863
• Mol File: 22980-57-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 478.4°C at 760 mmHg
• Flash Point: 210.1°C
• Density: 1.129g/cm³
• Vapor Pressure: 2.57E-09mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: 5-methoxy-8,8-dimethyl-10-(2-methylbut-3-en-2-yl)-2H,8H-pyrano[3,2-g]chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methoxy-8,8-dimethyl-10-(2-methylbut-3-en-2-yl)-2H,8H-pyrano[3,2-g]chromen-2-one(22980-57-0)
• EPA Substance Registry System: 5-methoxy-8,8-dimethyl-10-(2-methylbut-3-en-2-yl)-2H,8H-pyrano[3,2-g]chromen-2-one(22980-57-0)

Safety Data

• Hazardous Substances Data: 22980-57-0(Hazardous Substances Data)

Upstream product

• 88223-86-3 5-acetoxy-6-(1,1-dimethylallyl)seselin 
• 74-88-4 methyl iodide 
• 88223-87-4 5-hydroxy-6-(1,1-dimethylallyl)seselin 

Relevant articles and documents

CLAISEN REARRANGEMENTS-XIII SYNHESIS OF THE NATURAL COUMARINS, NORDENTATIN, DENTATIN AND CLAUSARIN

The structure of the natural coumarin, clausarin 10 has been confirmed by an eight step synthesis from 5-hydroxyseselin 1 in 56percent overall yield.The efficient synthesis of its precursor, nordentatin 5 provides a convenient alternative synthetic route to dentatin 6.The revised structure 13 is suggested for clausenidinaric acid.

Anti-HBV and cytotoxic activities of pyranocoumarin derivatives

Four natural pyranocoumarins clausenidin (1), nordentatin (2), clausarin (3), and xanthoxyletin (4) were isolated from the medicinal plant Clausena excavata. Recently, we found that 1 and 2 suppressed hepatitis B virus surface antigen in HepA2 cells, and in addition, 1-3 showed cytotoxic activity against four human cancer cell lines (A549, MCF7, KB, and KB-VIN). To explore the SAR of 1-4, 17 pyranocoumarin analogues (5-21) were designed and synthesized. Among these analogues, 5 and 10 were the most potent against hepatitis B virus with EC50 values of 1.14 and 1.34 μM, respectively. The most interesting result in the cytotoxicity assay was the significant activity of 1, 5, and 6 against the multi-drug resistant cell line, KB-VIN, without activity against the KB cell line. These data suggest that these three compounds could be useful hits for developing MDR-inverse drugs.