1824-94-8

Basic information

• Product Name: METHYL-BETA-D-GALACTOPYRANOSIDE
• Synonyms: METHYL-BETA-D-GALACTOPYRANOSIDE;METHYL BETA-D-GALACTOSIDE;METHYL BETA-D-GALACTOSIDE(1,5);METHYL B-D-GALACTOPYRANOSIDE;BETA-METHYL-D-GALACTOSIDE;1-O-METHYL-GALACTOSIDE;1-O-METHYL-BETA-D-GALACTOPYRANOSIDE;1-OME-BETA-D-GAL
• CAS NO: 1824-94-8
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.18
• EINECS: 217-361-7
• Product Categories: Sugars, Carbohydrates & Glucosides;13C & 2H Sugars;Biochemistry;Galactose;Glycosides;Sugars;Carbohydrates & Derivatives
• Mol File: 1824-94-8.mol
• Article Data: 125

Chemical Properties

• Melting Point: 172-180 °C
• Boiling Point: 250.62°C (rough estimate)
• Flash Point: 189.1 °C
• Appearance: White/Crystalline Powder
• Density: 1.47
• Vapor Pressure: 1.15E-07mmHg at 25°C
• Refractive Index: -16.5 ° (C=1.5, MeOH)
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 12.92±0.70(Predicted)
• Water Solubility: Soluble in water and methanol.
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 81569
• CAS DataBase Reference: METHYL-BETA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-BETA-D-GALACTOPYRANOSIDE(1824-94-8)
• EPA Substance Registry System: METHYL-BETA-D-GALACTOPYRANOSIDE(1824-94-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 1824-94-8(Hazardous Substances Data)

Usage

Description

METHYL-BETA-D-GALACTOPYRANOSIDE is a beta-D-galactopyranoside with a methyl substituent at the anomeric position. It is a white crystalline solid that serves as a weak substrate and an effective inducer of beta-D-galactosidase.

Uses

Used in Enzyme Induction:
METHYL-BETA-D-GALACTOPYRANOSIDE is used as an inducer for beta-D-galactosidase, an enzyme that plays a crucial role in the metabolism of lactose and other galactosides. Its ability to induce the enzyme makes it valuable in research and applications related to enzyme activity and regulation.
Used in Biochemical Research:
In the field of biochemical research, METHYL-BETA-D-GALACTOPYRANOSIDE is used as a weak substrate to study the activity and specificity of beta-D-galactosidase and related enzymes. This allows researchers to gain insights into enzyme mechanisms and develop potential therapeutic agents targeting these enzymes.
Used in Pharmaceutical Development:
METHYL-BETA-D-GALACTOPYRANOSIDE may also be utilized in the development of pharmaceuticals targeting beta-D-galactosidase or related enzymes. Its properties as a weak substrate and effective inducer can aid in the design and optimization of drugs for various therapeutic applications.
Used in Food Industry:
In the food industry, METHYL-BETA-D-GALACTOPYRANOSIDE can be used as a component in the development of lactose-free or reduced-lactose products. Its ability to induce beta-D-galactosidase activity can help in the breakdown of lactose, making it a valuable ingredient for individuals with lactose intolerance or those seeking lactose-reduced options.

InChI:InChI=1/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3?,4-,5+,6?,7+/m0/s1

Upstream product

• 59-23-4 D-Galactose 
• 92673-60-4 methyl β-D-galactoside 6-sulfate 
• 67-56-1 methanol 
• 10257-28-0 D-Galactose 
• 3150-25-2 3-nitrophenyl β-D-galactopyranoside 
• 73977-52-3 2,4-di-O-acetyl-β-methyl-D-galactopyranosideuronic acid γ-lactone 
• 92516-72-8 C₂₈H₂₅O₈⁽¹⁺⁾ 
• 92516-62-6 methyl 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-β-D-galactopyranoside 
• 123164-25-0 capsicastrine 
• 709-50-2 methyl beta-D-glucopyranoside 
• 2818-58-8 phenyl-β-D-galactopyranoside 
• 5019-23-8 methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 124-41-4 sodium methylate 
• 761-01-3 triethylamine sulfur trioxide 

Downstream Products

• 18311-26-7 methyl 6-O-triphenylmethyl-β-D-galactopyranoside 
• 64952-14-3 (R)-3-hydroxy-2-((R)-1-methoxy-2-oxo-ethoxy)-propionaldehyde 
• 71117-36-7 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 20688-90-8 methyl 4,6-O-isopropylidene-β-D-galacytopyranoside 
• 2296-39-1 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-β-D-galactopyranoside 
• 114102-83-9 methyl β-D-galactopyranoside 6-(diphenyl phosphate) 
• 3162-96-7 methyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 100638-59-3 C₃₅H₃₀⁽²⁾H₈O₆ 
• 136113-05-8 (3aS,4R,6R,7R,7aR)-7-Hydroxy-4-hydroxymethyl-6-methoxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one 
• 136113-00-3 Carbonic acid benzyl ester (2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 51897-73-5 methyl 2,6-di-O-acetyl-3,4-O-benzylidene-β-D-galactopyranoside 
• 112968-15-7 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glalactopyranoside 
• 87591-35-3 Methyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-galactopyranoside 
• 67393-10-6 methyl 6-O-benzyl-β-D-galactopyranoside 

Relevant articles and documents

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Operationally simple and efficient workup procedure for TBAF-mediated desilylation: Application to halichondrin synthesis

An operationally simple and efficient workup method for tetrabutylammonium fluoride (TBAF)-mediated t-butyldimethylsilyl (TBS) deprotection has been developed. The procedure includes addition of a sulfonic acid resin and calcium carbonate, followed by filtration and evaporation. This method eliminates the tedious aqueous-phase extraction process to remove excess TBAF and materials derived from TBAF, thereby making the protocol highly amenable to multiple TBS deprotections. Its efficiency and usefulness were demonstrated by using the transformation of 1 a to 3a in the halichondrin synthesis.

Preliminary 1H NMR investigation of sialic acid transfer by the trans-sialidase from Trypanosoma cruzi

1H NMR spectroscopy has been used to investigate the transfer of sialic acid from sialic acid donor molecules to acceptor molecules using the trans-sialidase from Typanosoma cruzi. It is clearly demonstrated that NMR spectroscopy is an efficien

Catalytic Consequences of Experimantal Evolution. Part 1. Catalysis by the Wild-type Second β-Galactosidase (ebg0) of Escherichia coli: a Comparison with the lacZ Enzyme

β-D-Galactopyranose is the initial product of the hydrolysis of β-D-galactopyranosyl fluoride by ebg0 enzyme.Transfer to methanol of a β-D-galactopyranosyl residue from either m-nitrophenol or 3-bromopyridine is seven times more favourable than

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Calixanthomycin A: Asymmetric Total Synthesis and Structural Determination

We report the first asymmetric total synthesis and structural determination of calixanthomycin A. Taking advantage of a modular strategy, a concise approach was developed to assemble the hexacyclic skeleton with both enantiomers of the lactone A ring. Stereoselective glycosylation coupled the angular hexacyclic framework with a monosaccharide fragment to produce calixanthomycin A and its stereoisomers. This enable us to determine and assign the absolute configuration of C-25 (25S) and monosaccharide (derivative of l-glucose).

Structure of the unusual Sinorhizobium fredii HH103 lipopolysaccharide and its role in symbiosis

Rhizobia are soil bacteria that form important symbiotic associations with legumes, and rhizobial surface polysaccharides, such as K-antigen polysaccharide (KPS) and lipopolysaccharide (LPS), might be important for symbiosis. Previously, we obtained a mutant of Sinorhizobium fredii HH103, rkpA, that does not produce KPS, a homopolysaccharide of a pseudaminic acid derivative, but whose LPS electrophoretic profile was indistinguishable from that of the WT strain. We also previously demonstrated that the HH103 rkpLMNOPQ operon is responsible for 5-acetamido-3,5,7,9-tetradeoxy-7-(3-hydroxybutyramido)-L-glyc-ero-L-manno-nonulosonic acid [Pse5NAc7(3OHBu)] production and is involved in HH103 KPS and LPS biosynthesis and that an HH103 rkpM mutant cannot produce KPS and displays an altered LPS structure. Here, we analyzed the LPS structure of HH103 rkpA, focusing on the carbohydrate portion, and found that it contains a highly heterogeneous lipid A and a peculiar core oligosaccharide composed of an unusually high number of hexuronic acids containing b-configured Pse5NAc7(3OHBu). This pseudaminic acid derivative, in its a-configuration, was the only structural component of the S. fredii HH103 KPS and, to the best of our knowledge, has never been reported from any other rhizobial LPS. We also show that Pse5NAc7(3OHBu) is the complete or partial epitope for a mAb, NB6-228.22, that can recognize the HH103 LPS, but not those of most of the S. fredii strains tested here. We also show that the LPS from HH103 rkpM is identical to that of HH103 rkpA but devoid of any Pse5NAc7(3OHBu) residues. Notably, this rkpM mutant was severely impaired in symbiosis with its host, Macroptilium atropurpureum.