Methyl b-D-lactopyranoside

Methyl β-D-lactopyranoside is a chemically synthesized methyl glycoside derivative of D-lactose comprising a β-D-glucopyranosyl unit glycosidically linked to a methyl group at the anomeric position. This compound appears as a white crystalline solid and is widely used in carbohydrate chemistry and glycobiology as a stable non-reducing sugar analog. With the methyl group capping the anomeric carbon, it offers greater chemical stability and resistance to mutarotation compared to free lactose, facilitating its use in glycosylation reactions and the synthesis of oligosaccharides and glycoconjugates. Its molecular formula is C8H16O6 with a molecular weight of approximately 208.21 g/mol. Synthesized via glycosylation reactions under controlled laboratory conditions, it is purified to high purity (≥98%) and free from microbial contamination. Methyl β-D-lactopyranoside is typically stored under refrigerated conditions to preserve stability and maintain shelf life of 1–2 years. It finds applications spanning biochemical assays, drug development, enzymatic substrate research, and molecular probe design.

IUPAC Name

• Methyl β-D-lactopyranoside

Appearance

• White crystalline powder

Source

• Produced via chemical glycosylation of lactose or its derivatives with methanol
• Synthesized and purified using established laboratory procedures to ensure chemical purity and safety

Molecular Weight and Structure

• Molecular formula: C8H16O6
• Molecular weight: 208.21 g/mol
• Structure: β-D-galactopyranosyl-β-D-glucopyranoside with a methyl group at the reducing-end anomeric carbon
• SMILES: CCOC1OC@@HC@HC@@H[C@H]1O[C@H]2OC@@HC@HC@@H[C@H]2O

Sugar Specificity

• Contains β-D-galactose and β-D-glucose units connected via β(1→4) glycosidic bond
• Methyl group at α-position stabilizes structure as a non-reducing sugar analog

Biological Activity

• Functional intermediate and substrate analog in enzymatic studies and glycomimetic research
• No direct pharmacological effect but important in biochemical assays to analyze sugar metabolism and enzyme activity

Purity and Microbial Contamination

• Purity typically ≥98%, confirmed by NMR and chromatographic analysis
• Manufactured under sterile conditions minimizing microbial contamination risk

Identity and Quality Control

• Confirmed by NMR (1H, 13C), MS, and HPLC purity profiles
• Supplied with Certificates of Analysis and Safety Data Sheets
• Melting point and optical rotation included as batch-specific quality controls

Shelf Life and Storage

• Store tightly sealed at 2–8 °C in a dry, dark environment
• Avoid exposure to moisture and heat to maintain stability
• Shelf life of 1–2 years under recommended conditions

Application

• Used in synthesis of glycosides, oligosaccharides, and glycoconjugates
• Important as a reference compound and substrate in enzymatic assays
• Employed in drug discovery, molecular probe development, and glycan structure-function studies

Key Characteristics

• Methylated β-D-lactopyranoside, non-reducing disaccharide analog
• CAS Number: 22047-81-0
• Molecular Weight: 208.21 g/mol
• White crystalline solid, stable with high purity
• Versatile in synthetic glycosylation and enzymology research
• Full analytical characterization and quality control documentation
• Maintains stability under refrigerated, moisture-free storage conditions

Citations

• CalpacLab product data
• AnaxLab chemical info
• PubChem molecular details
• Sigma-Aldrich glycoside references
• MedChemExpress biochemical reagents
• PMC biochemical studies
• Synthose glycosylation intermediates
• Patent literature on sugar derivatives
• Benchchem chemical catalog
• ScienceDirect glycobiology reviews