143390-87-8

Basic information

• Product Name: (E)-9-[[5-(3,3-Dimethyloxiranyl)-3-methyl-2-pentenyl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one
• Synonyms: (E)-9-[[5-(3,3-Dimethyloxiranyl)-3-methyl-2-pentenyl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one;6',7'-Epoxy,8-Geranylpsoralen
• CAS NO: 143390-87-8
• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.39638
• Mol File: 143390-87-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.210
• CAS DataBase Reference: (E)-9-[[5-(3,3-Dimethyloxiranyl)-3-methyl-2-pentenyl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-9-[[5-(3,3-Dimethyloxiranyl)-3-methyl-2-pentenyl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one(143390-87-8)
• EPA Substance Registry System: (E)-9-[[5-(3,3-Dimethyloxiranyl)-3-methyl-2-pentenyl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one(143390-87-8)

Safety Data

• Hazardous Substances Data: 143390-87-8(Hazardous Substances Data)

Usage

General Description

The chemical compound "(E)-9-[[5-(3,3-Dimethyloxiranyl)-3-methyl-2-pentenyl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one" is a complex organic molecule with a fused furan and benzopyran ring system. It contains a furan ring fused to a benzopyran ring, and has a pentenyl group and an oxiranyl group attached to it. The compound also contains a ketone functional group. This chemical structure gives it potential pharmaceutical or biological activity, as compounds with similar structures have been reported to exhibit anticancer, anti-inflammatory, and antioxidant properties. It is important for future research to determine the pharmacological potential and safety profile of this compound for potential drug development or other applications.

Upstream product

• 71612-25-4 8-geranyloxypsoralen 

Downstream Products

• 68123-30-8 Dihydro-8-hydroxypsoralen 
• 2009-24-7 8-hydroxypsoralen 

Relevant articles and documents

Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4

Furanocoumarins have been shown to inhibit CYP3A4 in vitro with varying degrees of potency [Pharmacogenetics 1997, 7, 391-396; Chem. Res. Toxicol. 1998, 11, 252-259; Drug Metab. Dispos. 1997, 25, 1228-1233; Br. J. Pharmacol. 2000, 130, 1369-1377]. In this study, we report the effects of a series of novel furanocoumarins based on the naturally occurring derivative 8-geranylepoxypsoralen which has been shown to be a more potent inhibitor of CYP3A4 than its 5-position-substituted counterpart bergamottin [Drug Metab. Dispos. 2000, 28, 766-771; Jpn. J. Pharmacol. 2000, 82, 122-129]. Compounds were designed, synthesised and tested for their ability to inhibit CYP3A4 activity in human liver microsomes using testosterone as the marker substrate. Both the saturated and unsaturated phenolic furanocoumarin derivatives were found to be inactive. However, the 8-alkyloxy-furanocoumarin analogues were shown to inhibit CYP3A4 activity in a dose dependent manner, with IC50 values ranging from 0.78 ± 0.11 to 3.93 ± 0.53 μM. The reduced furan derivative dihydro-8-geranyloxypsoralen showed a 4-fold decrease in inhibitory potency, suggesting that the furan moiety plays a role in the interaction between these compounds and CYP3A4.