Methyl α-D-rhamnopyranoside

Methyl α-D-rhamnopyranoside is a methylated glycoside of the deoxy sugar D-rhamnose, formed by replacement of the anomeric hydroxyl group with a methoxy group resulting in a stable α-glycosidic bond. It appears as a white to off-white crystalline powder and is predominantly synthesized by methylation of D-rhamnose. This compound is widely utilized as an intermediate in carbohydrate chemistry, synthetic glycoconjugate development, and biological research of rhamnose-containing molecules. Its structure is used to probe glycosylation mechanisms, enzyme substrate specificity, and for building complex oligosaccharides or saponin analogs important in bioactivity and drug research. Methyl α-D-rhamnopyranoside also serves as a standard for analytical methods in carbohydrate sciences and is used in antimicrobial and cytotoxicity studies for its ability to mimic or modify natural glycan structures, with reliably high purity and quality control standards for research and bioassays.

IUPAC Name

• (2R,3R,4R,5R,6S)-2-methoxy-6-methyloxane-3,4,5-triol
• Sometimes listed as methyl 6-deoxy-α-D-mannopyranoside

Appearance

• White to off-white crystalline solid or powder

Source

• Chemically synthesized via methylation of D-rhamnose
• May occur as a minor constituent in some plant and microbial glycosides

Molecular Weight and Structure

• Molecular formula: C7H14O5
• Molecular weight: 178.18 g/mol
• Structure: Six-membered pyranose ring, methyl group at anomeric carbon, methyl (instead of hydroxyl) at C6 (deoxy), stereochemistry defined by D-configuration
• SMILES: CO[C@H]1OC@HC@@HC@@H[C@@H]1O

Sugar Specificity

• A methylated derivative of D-rhamnose, part of the 6-deoxyhexose family
• Employed in synthesis and study of rhamnose-containing glycans

Biological Activity

• Used to explore mechanisms of glycosylation and enzyme recognition
• Studied for antimicrobial and cytotoxic properties as part of saponin and rhamnoside derivatives
• Shown to be valuable in developing cytotoxic and antifungal agents in medicinal chemistry

Purity and Microbial Contamination

• Commercially available at ≥98% purity (HPLC/GC)
• Microbial contamination minimized by chemical synthesis and stringent QC

Identity and Quality Control

• Verified by NMR, HPLC, GC, mass spectrometry, optical rotation
• Melting point ~106–108°C (may vary by batch and source)
• MSDS and Certificate of Analysis supplied with commercial batches

Shelf Life and Storage

• Store in cool, dry, and sealed containers, typically at room temperature or refrigerated (2–8°C)
• Stable for 1–3 years with proper storage; avoid exposure to moisture and light

Application

• Intermediate in glycan, saponin, and oligosaccharide synthesis
• Standard for analytical and biochemical research
• Used in studies of enzyme specificity, cell signaling, and carbohydrate-protein interactions
• Evaluated in antimicrobial and cytotoxicity assays
• Applied in quality control methods for carbohydrate-containing products

Key Characteristics

• Methylated α-glycoside of D-rhamnose
• CAS number 15814-59-2
• White to off-white crystalline powder, molecular weight 178.18 g/mol
• High purity (≥98%) verified by analytical techniques
• Stable under refrigerated or dry, ambient conditions
• Model compound for glycosylation, bioactivity, and analytical studies
• Utilized as a building block in synthetic and medicinal chemistry
• Verified identity by NMR, mass spectrometry, and COA
• Reliable shelf life and well-documented stability
• Recognized for antimicrobial, cytotoxicity, and enzyme assay relevance

Citation 

• A2BChem product data
• ChemicalBook datasheet
• PubChem structure and CAS
• ThermoFisher catalog/shelf life
• TCI catalog and purity standards
• ScienceDirect structure/analysis
• ACS Publications cytotoxic/biological studies
• NCBI antimicrobial review
• FSPublisher antimicrobial evaluation
• LookChem product/research