159954-28-6

Basic information

• Product Name: 6-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE
• Synonyms: 6-Chloro-3-indolylb-D-glucopyranoside;6-Chloro-3-indolyl β-D-glucopyranoside ,98%;6-Chloro-3-indolyl-beta-D-glucopyranoside (Rose Glu);6-Chloro-3-indoxyl-beta-D-glucopyranoside Monohydrate;SALMON(TM)-BETA-D-GAL;SALMON(TM)-BETA-D-GALACTOSIDE;SALMON(TM)-BETA-D-GLC;SALMON(TM)-BETA-D-GLUCOSIDE
• CAS NO: 159954-28-6
• Molecular Formula: C14H16ClNO6
• Molecular Weight: 329.73
• EINECS: 1533716-785-6
• Product Categories: substrate
• Mol File: 159954-28-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 630.228 °C at 760 mmHg
• Flash Point: 334.95 °C
• Appearance: /
• Density: 1.641 g/cm³
• Vapor Pressure: 9.45E-17mmHg at 25°C
• Refractive Index: 1.717
• Storage Temp.: 2-8°C
• PKA: 12.84±0.70(Predicted)
• CAS DataBase Reference: 6-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE(159954-28-6)
• EPA Substance Registry System: 6-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE(159954-28-6)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• F: 8-10-21
• Hazardous Substances Data: 159954-28-6(Hazardous Substances Data)

Usage

Description

6-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE, also known as X-Gal, is a synthetic compound commonly used in molecular biology and microbiology. It is a derivative of the sugar galactose, with a chlorine atom at the 6th position and an indole group attached. X-Gal is known for its ability to produce a blue color when it interacts with specific enzymes, making it a useful tool for various applications.

Uses

Used in Molecular Biology:
6-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE is used as a chromogenic substrate for the detection of β-galactosidase activity. This application is particularly useful in molecular cloning, where the presence of the enzyme indicates successful gene expression or the presence of a specific bacterial strain.
Used in Microbiology:
In the field of microbiology, 6-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE is used as a selective agent for the identification of yeasts with β-glucosidase activity. This enzyme is responsible for breaking down the compound, resulting in a blue-colored product that can be easily observed and used for classification purposes.
Used in Biomedical Research:
6-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE is also employed in biomedical research as a marker for cell differentiation, apoptosis, and other cellular processes. Its ability to produce a visible color change upon interaction with specific enzymes makes it a valuable tool for tracking and analyzing cellular events in various experimental setups.
Used in Drug Delivery Systems:
Similar to gallotannin, 6-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE can be incorporated into drug delivery systems to improve the targeting and efficacy of therapeutic agents. Its unique properties may be utilized to enhance the delivery of drugs to specific cells or tissues, potentially improving treatment outcomes and reducing side effects.

InChI:InChI=1/C14H16ClNO6/c15-6-1-2-7-8(3-6)16-4-9(7)21-14-13(20)12(19)11(18)10(5-17)22-14/h1-4,10-14,16-20H,5H2/t10-,11-,12+,13-,14+/m1/s1

Upstream product

• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 3947-62-4 2,3,4,6-tetraacetylglucose 
• 604-68-2 α-D-glucopyranose peracetylate 

Relevant articles and documents

Substrate and preparation method and application thereof

The invention discloses a substrate namely alpha-D-glucoside for detecting activity of alpha-glucosidases, and further discloses a synthesis technology of the substrate. The synthesis technology comprises the steps of enabling a compound alpha-D-glucose and acetyl chloride to be subjected to a reaction, and performing purification to obtain alpha-D- pentacetylglucose; catalyzing the obtained substances with N,N-Dimethyl-1,3-diaminopropane, performing pickling, performing extraction, performing drying, and performing purifying to obtain 2,3,4,6-tetra-O-acetyl-alpha-D-acetyl-glucosamine; catalyzing the obtained substances in a dichloromethane solution, performing a reaction with trichloroacetonitrile, performing filtering, and performing purifying to obtain 2,3,4,6-tetra-O-acetyl-beta-D-glucosyl trichloroacetimidate; performing catalyzing on the obtained substances in a dichloromethane solution, performing a reaction with chromogen or fluorophore, performing extraction, merging organic phases, performing drying, performing concentrating, performing methanol redissolution, performing crystal nourishing at 4 DEG C, and performing filtering to obtain 2,3,4,6-tetra-O-acetyl-alpha-D-glucoside; and catalyzing the obtained substances in a methanolic solution, performing a reaction, then performing decoloring adsorption, performing filtering, and performing purifying. The synthesis technology of the substrate is simple and high in yield, the sensitivity of a reagent kit can be improved, the stability is good, and the specificity is high.