484-14-0

Basic information

• Product Name: osthenol
• Synonyms: 7-Hydroxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one;7-Hydroxy-8-isopentenyl-2H-1-benzopyran-2-one;7-Hydroxy-8-prenylcoumarin;NSC 625328
• CAS NO: 484-14-0
• Molecular Formula: C₁₄H₁₄O₃
• Molecular Weight: 230.26
• Mol File: 484-14-0.mol
• Article Data: 17

Chemical Properties

• Melting Point: 89-91 °C
• Boiling Point: 422.8°C at 760 mmHg
• Flash Point: 184.1°C
• Appearance: /
• Density: 1.203g/cm³
• Vapor Pressure: 9.53E-08mmHg at 25°C
• Refractive Index: 1.595
• PKA: 8.45±0.20(Predicted)
• CAS DataBase Reference: osthenol(CAS DataBase Reference)
• NIST Chemistry Reference: osthenol(484-14-0)
• EPA Substance Registry System: osthenol(484-14-0)

Safety Data

• Hazardous Substances Data: 484-14-0(Hazardous Substances Data)

Usage

General Description

Osthenol is a bioactive chemical compound found in Citrus plants, particularly in the essential oils of their fruits and leaves. It belongs to a group of organic compounds known as coumarins, which are responsible for the characteristic scent and flavor of citrus fruits. Osthenol has been studied for its potential health benefits, including its antimicrobial, anti-inflammatory, and antioxidant properties. Research has also suggested that osthenol may have potential as a therapeutic agent for various health conditions, including cancer, diabetes, and neurodegenerative diseases. Additionally, osthenol has been investigated for its insecticidal properties, with potential applications in agriculture and pest control. Overall, osthenol is a versatile chemical compound with a wide range of potential uses and health benefits.

InChI:InChI=1/C14H14O3/c1-9(2)3-6-11-12(15)7-4-10-5-8-13(16)17-14(10)11/h3-5,7-8,15H,6H2,1-2H3

Upstream product

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Downstream Products

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Relevant articles and documents

Selective Inhibitory Effect of Osthenol on Human Cytochrome 2C8

Osthenol is a furanocoumarin with anti-tumor, anti-inflammatory, and anti-viral activity. It is present in various citrus juices and fruits; however, its inhibitory effects on cytochrome P450 (CYP) enzyme activity, in the context of herb–drug interaction (HDI) prediction, have not been previously studied. In this study, osthenol was chemically synthesized in order to identify potential HDIs. Its inhibitory effect on eight CYP isoforms and the underlying mechanism of inhibition were investigated by using cocktail assays and liquid chromatography-tandem mass spectrometry in pooled human liver microsomes. The inhibitory effect of osthenol on CYP2C8-catalyzed paclitaxel hydroxylation was selective and dose-dependent, but not time-dependent. The IC50 value was 2.8 μM. Additionally, osthenol displayed mixed mode inhibition with a relatively low Ki value of 0.96 μM, which is indicative of the potential for HDIs with co-administered CYP2C8 substrates. To the best of our knowledge, this is the first report of selective inhibition of CYP2C8 by osthenol.

Design and synthesis of Osthole-based compounds as potential Nrf2 agonists

A total of 23 compounds based on Osthole skeleton were designed and synthesized. Their agonistic activity for Nrf2 were evaluated by Dual-luciferase Reporter Gene Assay. Most of the compounds showed better activities compared with Osthole, especially O15 and O21. And the median effective concerntration (EC50) values was calculated accordingly, both of which showed remarkable activity for Nrf2. The structure activity relationship study indicated that introduction of the structure of stilbene might be beneficial for enhancement of agonistic properties of Osthole, and the position of the substituent may have a greater effect on the activity than the electron-donating/withdrawing ability of the substituent. Mechanism of the action of selected compound O15 was investigated by molecular docking, cellular thermal shift assay and ubiquitination assay, which suggested the reason why O15 exhibited relatively stronger agonistic activity for Nrf2. Compound O15 and O21 both provided novel methods to investigate Osthole-based compounds as Nrf2 agonists.

PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

Synthesis of coumarin derivatives and their cytoprotective effects on t-BHP-induced oxidative damage in HepG2 cells

Coumarins are ubiquitous in higher plants and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of coumarin derivatives on tert-butyl hydroperoxide (t-BHP)-induced oxidative damage in human hepatoma HepG2 cells. A series of coumarin derivatives were prepared and assessed for their cytoprotective effects. Among these, a caffeoyl acid-conjugated dihydropyranocoumarin derivative, caffeoyllomatin, efficiently protected against cell damage elicited by t-BHP. Our findings suggest that caffeoyllomatin appears to be a potent cytoprotective agent.