19285-38-2

Basic information

• Product Name: 1-BROMO-2,3,4,6-TETRA-ACETYL-BETA-D-GALACTOSIDE
• Synonyms: ACETIC ACID (2R,3S,4S,5R,6S)-3,4,5-TRIACETOXY-6-BROMO-TETRAHYDRO-PYRAN-2-YLMETHYL ESTER;ACETOBROMO-BETA-D-GALACTOSE;1-BROMO-2,3,4,6-TETRA-ACETYL-BETA-D-GALACTOSIDE;1-Bromo-2,3,4,6-tetra-acetyl-D-galactoside;2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosylbromide;1-BROMO-2,3,4,6-TETRA-ACETYL-SS-D-GALACTOSIDE;1-BroMo-2,3,4,6-tetra-O-acetyl-^b-D-galactoside, 95%, stab. with 2% calciuM carbonate
• CAS NO: 19285-38-2
• Molecular Formula: C₁₄H₁₉BrO₉
• Molecular Weight: 411.2
• Product Categories: Sugars, Carbohydrates & Glucosides
• Mol File: 19285-38-2.mol
• Article Data: 114

Chemical Properties

• Boiling Point: 412.007 °C at 760 mmHg
• Flash Point: 202.975 °C
• Appearance: /
• Density: 1.49 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.503
• CAS DataBase Reference: 1-BROMO-2,3,4,6-TETRA-ACETYL-BETA-D-GALACTOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2,3,4,6-TETRA-ACETYL-BETA-D-GALACTOSIDE(19285-38-2)
• EPA Substance Registry System: 1-BROMO-2,3,4,6-TETRA-ACETYL-BETA-D-GALACTOSIDE(19285-38-2)

Safety Data

• Hazardous Substances Data: 19285-38-2(Hazardous Substances Data)

Usage

Chemical structure

A synthetic analog of lactose with a bromine atom at the first carbon and acetyl groups at the second, third, fourth, and sixth carbons.

Function

Acts as a substrate for beta-galactosidase enzyme assays.

Application

Commonly used in biochemical research for the detection and measurement of beta-galactosidase activity.

Detection method

Hydrolysis by beta-galactosidase results in the release of a yellow-colored product, allowing for easy measurement of enzyme activity.

Use in gene expression studies

Utilized to study gene expression, particularly in the context of the lac operon in Escherichia coli.

Use in cell biology

Helps in understanding the role of beta-galactosidase in cellular processes.

Use in enzyme kinetics

Provides insights into the kinetics of beta-galactosidase enzyme activity.

Use in bacterial growth and metabolism studies

Induces the lac operon in Escherichia coli, allowing researchers to study bacterial growth and metabolism.

Chromogenic and fluorogenic properties

The compound serves as both a chromogenic (color-producing) and fluorogenic (fluorescence-producing) substrate for beta-galactosidase.

Solubility

Typically soluble in organic solvents such as dimethyl sulfoxide (DMSO) or methanol, which allows for its use in various experimental setups.

InChI:InChI=1/C14H19BrO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11+,12+,13-,14-/m1/s1

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 67337-79-5 2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 7296-64-2 β-D-galactopyranoside 
• 108-24-7 acetic anhydride 
• 2280-44-6 D-Glucose 
• 506-96-7 Acetyl bromide 
• 530-26-7 D-Mannose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 10257-28-0 D-Galactose 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 
• 59-23-4 D-Galactose 
• 25878-60-8 D-galactose pentaacetate 

Downstream Products

• 96553-99-0 5-benzylidene-3-(tetra-O-acetyl-ξ-D-glucopyranosyl)-2-thioxo-thiazolidin-4-one 
• 97074-54-9 5-(4-methoxy-benzylidene)-3-(tetra-O-acetyl-ξ-D-glucopyranosyl)-2-thioxo-thiazolidin-4-one 
• 79258-27-8 methyl 3,4-O-endo-(2-nitrobenzylidene)-2-O-(tetra-O-acetyl-β-D-glucopyranosyl)-α-L-fucopyranoside 
• 79258-27-8 methyl 3,4-O-exo-(2-nitrobenzylidene)-2-O-(tetra-O-acetyl-β-D-glucopyranosyl)-α-L-fucopyranoside 
• 915-05-9 stigmast-5-en-3-yl acetate 
• 25694-37-5 di-β-sitosteryl ether 
• 66252-73-1 β-sitosteryl bromide 
• 79897-80-6 24-(R)-ethylcholesta-3,5-diene 
• 66252-74-2 β-sitosteryl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 4282-00-2 stigmast-5-en-3β-yl-(tetra-O-acetyl-β-D-glucopyranoside) 
• 146763-96-4 trans-dihydroperillyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 604-35-3 Cholesteryl acetate 
• 516-91-6 (3S,8S,9S,10R,13R,14S,17R)-3-Bromo-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene 
• 6907-84-2 (3β)-cholest-5-en-3-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Relevant articles and documents

Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity

Tacrine is a known Acetylcholinesterase (AChE) inhibitors having hepatotoxicity as main liability associated with it. The present study aims to reduce its hepatotoxicity by synthesizing tacrine linked triazole glycoconjugates via Huisgen's [3 + 2] cycloaddition of anomeric azides and terminal acetylenes derived from tacrine. A series of triazole based glycoconjugates containing both acetylated (A-1 to A-7) and free sugar hydroxyl groups (A-8 to A-14) at the amino position of tacrine were synthesized in good yield taking aid from molecular docking studies and evaluated for their in vitro AChE inhibition activity as well as hepatotoxicity. All the hybrids were found to be non-toxic on HePG2 cell line at 200 μM (100 % cell viability) as compared to tacrine (35 % cell viability) after 24 h of incubation period. Enzyme kinetic studies carried out for one of the potent hybrids in the series A-1 (IC50 0.4 μM) revealed its mixed inhibition approach. Thus, compound A-1 can be used as principle template to further explore the mechanism of action of different targets involved in Alzheimer's disease (AD) which stands as an adequate chemical probe to be launched in an AD drug discovery program.

Synthesis of malformin-A1, C, a glycan, and an aglycon analog: Potential scaffolds for targeted cancer therapy

Improvement in therapeutic efficacy while reducing chemotherapeutic side effects remains a vital objective in synthetic design for cancer treatment. In keeping with the ethos of therapeutic development and inspired by the Warburg effect for augmenting biological activities of the malformin family of cyclic-peptide natural products, specifically anti-tumor activity, a β-glucoside of malformin C has been designed and synthesized utilizing precise glycosylation and solution phase peptide synthesis. We optimized several glycosylation procedures utilizing different donors and acceptors. The overarching goal of this study was to ensure a targeted delivery of a glyco-malformin C analog through the coupling of D-glucose moiety; selective transport via glucose transporters (GLUTs) into tumor cells, followed by hydrolysis in the tumor microenvironment releasing the active malformin C a glycon analog. Furthermore, total synthesis of malformin C was carried out with overall improved strategies avoiding unwanted side reactions thus increasing easier purification. We also report on an improved solid phase peptide synthesis protocol for malformin A1.

Synthesis and antimicrobial studies of novel n-glycosyl hydrazino carbothioamide

In view of applications of N-glycosylated compounds in medicinal chemistry and in many other ways, herein the synthesis of novel N-glycosyl hydrazino carbothioamides is reported. New N-glycosyl hydrazino carbothioamides were synthesized by the condensation of per-O-acetyl glycosyl isothiocyanate with different aromatic hydrazides. The newly synthesized compounds were characterized by using the IR, 1H NMR and mass spectral studies. Antimicrobial evaluation of the synthesized N-glycosyl hydrazino carbothioamide was also examined. Antimicrobial activities of the synthesized compound were evaluated against bacteria E. coli, P. aeruginosa, S. aureus, S. pyogenus and fungi C. albicans, A. niger and A. clavatus. All the N-glycosyl hydrazino carbothioamides exhibit promising antimicrobial activity.