28541-83-5

Basic information

• Product Name: 4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE
• Synonyms: 7-HYDROXY-4-METHYLCUMARIN-ALPHA-D-MANNOPYRANOSID;4-MU-BETA-D-MAN;4-MU-ALPHA-D-MAN;4-MU-ALPHA-D-MANNOSIDE;4'-METHYLUMBELLIFERYL ALPHA-D-MANNOPYRANOSIDE;4-METHYLUMBELLIFERYL-ALPHA-D-MANNOPYRANOSIDE;4-METHYLUMBELLIFERYL-ALPHA-D-MANNOPYRANOSIDE HYDRATE;4-METHYLUMBELLIFERYL BETA-D-MANNOSIDE
• CAS NO: 28541-83-5
• Molecular Formula: C₁₆H₁₈O₈
• Molecular Weight: 338.31
• EINECS: 249-073-2
• Product Categories: Substrates;Fluorescent Labels and Indicators;Carbohydrates & Derivatives;Fluorescent Labels & Indicators;AlphabeticalSubstrates;FluorogenicEnzyme Substrates;Mannosidase, alpha-;Mannoside;Fluorescent Enzyme Substrates;Fluorescent Probes, Labels, Particles and Stains;Substrates by Enzyme;substrate
• Mol File: 28541-83-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 190 °C
• Boiling Point: 626.9 °C at 760 mmHg
• Flash Point: 233.9 °C
• Appearance: White Solid
• Density: 1.522 g/cm³
• Storage Temp.: 2-8°C
• Solubility: pyridine: 20 mg/mL, clear, faintly yellow
• Stability: Hygroscopic
• BRN: 1266648
• CAS DataBase Reference: 4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE(28541-83-5)
• EPA Substance Registry System: 4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE(28541-83-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 28541-83-5(Hazardous Substances Data)

Usage

Description

4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE, also known as 4-MU-beta-D-Mannopyranoside, is a synthetic compound that serves as a substrate for various enzymes, particularly glycosidases. It is a white solid with unique chemical properties that make it useful in various applications across different industries.

Uses

Used in Enzyme Assays:
4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE is used as a substrate for mannosidase and N-acetyl-α-D-glucosaminidase enzymes. It is particularly useful in enzyme assays, where it helps in the detection and quantification of these enzymes' activities. The hydrolysis of 4-MU-beta-D-Mannopyranoside by these enzymes releases 4-methylumbelliferone, a fluorescent compound that can be easily measured, allowing for the assessment of enzyme activity.
Used in Analytical Chemistry:
4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE is used as an analytical reagent for studying biomass degradation by fungi. Its ability to act as a substrate for mannosidase enzymes makes it a valuable tool in understanding the enzymatic processes involved in the breakdown of complex carbohydrates in biomass, which has significant implications for biofuel production and other industrial applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE is used as a research tool to study the inhibition and activity of glycosidase enzymes, which are often targeted in the development of drugs for various diseases, including lysosomal storage disorders and cancer. Its role in enzyme assays aids in the identification and optimization of potential drug candidates.
Used in Biotechnology:
In the biotechnology sector, 4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE is employed as a substrate for the study of enzyme kinetics, enzyme inhibition, and enzyme mechanism. Its use in these studies contributes to the development of biotechnological applications, such as the production of biofuels, bioplastics, and other bio-based materials derived from biomass.

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 5980-33-6 sodium 4-methylumbelliferonate 
• 28541-71-1 4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 

Relevant articles and documents

Based on 4 - methyl [...] synthesis method of a plurality of glycoside

The invention discloses a method for synthesizing various glucosides on a basis of 4-methylumbelliferone. According to the invention, a glycosyl donor peracetyl saccharide and a glycosyl acceptor 4-methylumbelliferone are subjected to a glycosylation reaction under room temperature or under heating with dichloromethane or 1,2-dichloroethane as a solvent and with the combined effect of Lewis acid boron trifluoride ethyl ether and organic alkali triethylamine or pyridine; and protecting groups are removed, such that various glucosides based on 4-methylumbelliferone can be obtained. The glucosides include 4-methylumbelliferone-beta-D-glucopyranosiduronide, 4-methylumbelliferone-beta-D-glucopyranoside, 4-methylumbelliferone-beta-D-xylopyranoside, 4-methylumbelliferone-beta-D-ribofuranoside, 4-methylumbelliferone-alpha-D-galactopyranoside, and 4-methylumbelliferone-alpha-D-mannopyranoside. The method is simple, and can produce a beta or alpha single-configuration target. A glycosylation reaction yield can reach 17-93%.

CARBONIC ANHYDRASE INHIBITORS WITH ANTIMETASTATIC ACTIVITY

Compositions for the treatment of cancer comprising coumarin and thiocoumarin derivatives of Formulas I- XII are disclosed. Said derivatives preferentially inhibit carbonic anhydrase IX and XII (which are associated with hypoxic and metastatic tumours) over inhibiting carbonic anhydrase I and II activity. The compositions therefore are suited for treatment of hypoxic or metastatic cancers due to this selective mechanism of action.

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

The present invention encompasses compounds and methods for treating urinary tract infections.