198402-60-7

Basic information

• Product Name: 5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE
• Synonyms: RARECHEM AH BS 0010;MAGENTA(TM)-ALPHA-D-GAL;MAGENTA(TM)-ALPHA-D-GALACTOSIDE;5-BROMO-6-CHLORO-3-INDOLYL ALPHA-D-GALACTOPYRANOSIDE;5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE;5-Bromo-6-chloro-3-indolyla-D-galactopyranoside;Magenta-alpha-gal;5-Bromo-6-chloro-1H-indol-3-yl alpha-D-galactopyranoside
• CAS NO: 198402-60-7
• Molecular Formula: C14H15BrClNO6
• Molecular Weight: 408.63
• EINECS: 1533716-785-6
• Product Categories: substrate
• Mol File: 198402-60-7.mol

Chemical Properties

• Boiling Point: 674℃
• Flash Point: 361℃
• Appearance: /
• Density: 1.882
• Vapor Pressure: 4.44E-19mmHg at 25°C
• Refractive Index: 1.731
• CAS DataBase Reference: 5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE(198402-60-7)
• EPA Substance Registry System: 5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE(198402-60-7)

Safety Data

• Hazardous Substances Data: 198402-60-7(Hazardous Substances Data)

Usage

Uses

Used in Molecular Biology and Biochemistry Research:
5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE is used as a substrate for measuring the expression of the lac gene and monitoring the activity of beta-galactosidase. It is particularly useful in the study of gene expression and regulation, as well as in the analysis of enzymatic activity.
Used in Detection and Quantification of Beta-Galactosidase Activity:
In bacterial and mammalian cell cultures, 5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE is used as a substrate for the detection and quantification of beta-galactosidase activity. This allows researchers to assess the presence and activity of the enzyme in various biological samples.
Used in Enzyme Assays:
5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE is also employed in enzyme assays to evaluate the activity of beta-galactosidase. Its chromogenic properties make it an ideal substrate for colorimetric assays, providing a simple and reliable method for measuring enzymatic activity.

InChI:InChI=1/C14H15BrClNO6/c15-6-1-5-8(2-7(6)16)17-3-9(5)22-14-13(21)12(20)11(19)10(4-18)23-14/h1-3,10-14,17-21H,4H2/t10-,11-,12+,13-,14+/m0/s1

Upstream product

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• 910123-20-5 5-bromo-4-chloroisatoic anhydride 
• 50419-88-0 2-amino-5-bromo-4-chlorobenzene carboxylic acid 
• 1607828-44-3 N-acetyl-5-bromo-4-chloroanthranilic acid 
• 5900-55-0 N-(5-chloro-2-methylphenyl)acetamide 
• 1607828-43-2 N-(4-bromo-5-chloro-2-methylphenyl)-acetamide 

Relevant articles and documents

Synthesis of precipitating chromogenic/fluorogenic β-glucosidase/β-galactosidase substrates by a new method and their application in the visual detection of foodborne pathogenic bacteria

We developed a new efficient method for the synthesis of important indoxyl glycoside substrates for β-glucosidase and β-galactosidase by using 1-acetylindol-3-ones as intermediates. This method was used to synthesise novel precipitating fluorogenic substrates for β-glucosidase based on 2-(benzothiazol-2′-yl)-phenols. We also assessed the application of these substrates in the detection of foodborne pathogenic bacteria.

Synthesis method of glucoside based on indoxyl derivative and 2-(benzothiazol-2'-yl)phenol derivative

The invention discloses a synthesis method of glucoside based on an indoxyl derivative and a 2-(benzothiazol-2'-yl)phenol derivative. The general formula of a synthetic equation of the synthesis method is as shown in the description; the Ar-OH represents aromatic phenol or a ketonic compound thereof, and is used as a glycosyl receptor in a glycosylation reaction; the G-X represents halogenated sugar, and is used as a glycosyl donor in the glycosylation reaction. According to the synthesis method of the glucoside based on the indoxyl derivative and the 2-(benzothiazol-2'-yl)phenol derivative, a 1-acetylindolin-3-one derivative is selected and used as an intermediate; a novel synthesis method is researched and developed to prepare the glucoside based on the indoxyl derivative; a novel glycosidase fluorescence probe based on a BTP ((2-benzothiazol-2'-yl)phenyl) derivative is synthesized by applying the method; meanwhile, the application effects of the glucoside based on the indoxyl derivative and the glycosidase fluorescence probe are investigated. The glucoside based on the indoxyl derivative and the 2-(benzothiazol-2'-yl)phenol derivative can be used as glycosidase substrates, and is used for the positioning analytic detection and screening on the corresponding glycosidase, a microorganism using the corresponding glycosidase as a characteristic target, and the like.

Indoxylic acid esters as convenient intermediates towards indoxyl glycosides

Indoxylic acid methyl and allyl esters with varied halide-substitution patterns were obtained in excellent yields using a scalable route. Phase-transfer glycosylation of these key intermediates was carried out with various glycosyl halides. Subsequent mild silver-mediated decarboxylation followed by Zemplen deacetylation led to indoxyl glycosides in good overall yields. Indoxyl glycosides are well-established and widely used tools for enzyme screening and enzyme-activity monitoring. In the past, their synthesis has been difficult, so this new approach has led to a variety of useful structures. Indoxyl glycosides with varied halide-substitution patterns were synthesized using indoxylic acid esters as key intermediates. Glycosylation under phase-transfer conditions, ester cleavage, and mild decarboxylation led to the indoxyl glycosides in good yields. This approach enables access to a number of different indoxyl compounds. Copyright