29266-96-4

Basic information

• Product Name: 8-HYDROXYQUINOLINE-BETA-D-GLUCOPYRANOSIDE
• Synonyms: 8-((beta-d-glucopyranosyl)oxy)-quinolin;8-((beta-d-glucopyranosyl)oxy)quinoline;8-hydroxyquinoline-beta-d-glucoside;8-HYDROXYQUINOLINE-BETA-D-GLUCOPYRANOSIDE;8-HYDROXYQUINOLINE-BETA-D-GLUCOSE;8-hydroxyquinoline B-D-glucopyranoside;8-hydroxyquinoline β-d-glucopyranoside;8-hydroxyquinoline glucoside
• CAS NO: 29266-96-4
• Molecular Formula: C₁₅H₁₇NO₆
• Molecular Weight: 307.3
• EINECS: 1533716-785-6
• Product Categories: Quinolines, Quinazolines and derivatives;carbohydrate
• Mol File: 29266-96-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 582.5 °C at 760 mmHg
• Flash Point: 306.1 °C
• Appearance: /
• Density: 1.507 g/cm³
• Vapor Pressure: 2.06E-14mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: −20°C
• PKA: 12.69±0.70(Predicted)
• CAS DataBase Reference: 8-HYDROXYQUINOLINE-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-HYDROXYQUINOLINE-BETA-D-GLUCOPYRANOSIDE(29266-96-4)
• EPA Substance Registry System: 8-HYDROXYQUINOLINE-BETA-D-GLUCOPYRANOSIDE(29266-96-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: VB8580000
• Hazardous Substances Data: 29266-96-4(Hazardous Substances Data)

Usage

General Description

8-Hydroxyquinoline-beta-D-glucopyranoside is a chemical compound that consists of a sugar molecule (beta-D-glucopyranoside) linked to an 8-hydroxyquinoline molecule. It is known for its antioxidant and antimicrobial properties, making it potentially useful in a wide range of applications, including pharmaceuticals, cosmetics, and food preservation. 8-HYDROXYQUINOLINE-BETA-D-GLUCOPYRANOSIDE has also been studied for its potential therapeutic effects, particularly in the treatment of various diseases and conditions, such as cancer, neurodegenerative disorders, and microbial infections. Additionally, 8-Hydroxyquinoline-beta-D-glucopyranoside has been investigated for its potential use in metal ion chelation therapy and as a fluorescent probe for metal ions.

InChI:InChI=1/C15H17NO6/c17-7-10-12(18)13(19)14(20)15(22-10)21-9-5-1-3-8-4-2-6-16-11(8)9/h1-6,10,12-15,17-20H,7H2/t10-,12-,13+,14-,15?/m1/s1

Upstream product

• 148-24-3 8-quinolinol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 2280-44-6 D-Glucose 

Downstream Products

• 148-24-3 8-quinolinol 
• 492-61-5 β-D-glucose 

Relevant articles and documents

Synthesis of 8-hydroxyquinoline glycoconjugates and preliminary assay of their β1,4-GalT inhibitory and anti-cancer properties

8-Hydroxyquinoline scaffold is a privileged structure used in designing a new active agents with therapeutic potential. Its connections with the sugar unit is formed to improve the pharmacokinetic properties. The broad spectrum of activity of quinoline derivatives, especially glycoconjugates, is often associated with the ability to chelate metal ions or with the ability to intercalate into DNA. Simple and effective methods of synthesis glycoconjugates of 8-hydroxyquinoline and 8-hydroxyquinaldine derivatives, containing an O-glycosidic bond or a 1,2,3-triazole linker in their structure, have been developed. The obtained glycoconjugates were tested for their ability to inhibit β-1,4-Galactosyltransferase, as well as inhibit cancer cell proliferation. It was found that used glycoconjugation strategy influenced both improvement of activity and improvement of the bioavailability of 8-HQ derivatives. Their activity depends on type of attached sugar, presence of protecting groups in sugar moiety and presence of a linker between sugar and quinolone aglycone.