D-Rhamnose

D-Rhamnose is a naturally occurring deoxy sugar, chemically classified as a 6-deoxyhexose, structurally similar to D-mannose but lacking a hydroxyl group at the sixth carbon. It appears as a white crystalline powder and is widely found in nature, especially in bacterial and plant cell wall polysaccharides, as well as in some glycoproteins. D-Rhamnose plays crucial roles in bacterial pathogenesis, plant cell wall integrity, and as a microbial antigen in immunology. Its unique structural properties contribute to its involvement in cell signaling and recognition processes. D-Rhamnose is widely utilized in biochemistry and microbiology research to study bacterial glycans, develop vaccines, and investigate carbohydrate-protein interactions. It is commercially available at high purity for research applications in synthetic chemistry, glycoscience, and biomedical fields.​

IUPAC Name

• (2S,3S,4R,5R)-2,3,4,5-tetrahydroxyhexanal​

Appearance

• White crystalline powder​

Source

• Naturally sourced from bacterial, plant polysaccharides, and synthesized chemically for research​

Molecular Weight and Structure

• Molecular formula: C6H12O5
• Molecular weight: 164.16 g/mol​
• Structure: Deoxyhexose sugar featuring an aldehyde group in the open-chain form, with a six-carbon backbone missing a hydroxyl group at C6​
• SMILES: CC@@HC@HC@HC@@HC=O​

Sugar Specificity

• 6-deoxy sugar specific to rhamnose biosynthetic pathways; found in glycosylated bacterial cell wall components and plant polysaccharides​

Biological Activity

• Constituent of bacterial lipopolysaccharides and extracellular polysaccharides, playing roles in immune evasion and virulence
• Involved in plant cell wall structure and signaling
• Important for host-pathogen interactions and bacterial biofilm formation​

Purity and Microbial Contamination

• Purity typically ≥97-99% by chromatographic analysis for laboratory use
• Microbial contamination generally negligible for chemical-grade preparations​

Identity and Quality Control

• Confirmed by NMR, GC, HPLC, optical rotation, and melting point analysis
• Melting point: 120-160 °C (varies by source)
• Optical rotation: α-type around -8.6 to +8.2 °, β-type +38.4 to +8.9 ° (depending on conformation, in water)​

Shelf Life and Storage

• Recommended storage at 2–8 °C in dry, dark conditions
• Stable for up to 3-5 years depending on packaging and storage environment
• Protect from moisture and light exposure​

Application

• Used in glycoscience research to study bacterial and plant polysaccharides
• A key reagent for immunology studies on bacterial antigens and biofilm formation
• Utilized in synthetic carbohydrate chemistry for glycomimetic and vaccine development
• Employed in cell biology to investigate glycosylation-related cellular functions​

Key Characteristics

• Naturally occurring 6-deoxyhexose sugar involved in bacterial and plant glycans
• CAS number 634-74-2
• White crystalline powder with molecular weight 164.16 g/mol
• High-purity reagent for biochemical and pharmaceutical research
• Important in immunology and microbiology for its role in bacterial virulence
• Stable under refrigerated conditions for extended storage
• Well-characterized physical and chemical properties including specific optical rotation
• Widely used in glycobiology, synthetic carbohydrate chemistry, and vaccine research

Citation 

• Sigma-Aldrich D-Rhamnose product information​
• PubChem D-Rhamnose molecular data​
• ChemicalBook D-Rhamnose specifications​
• CAS Common Chemistry reference​
• PMC article on fucose biological functions​
• BioRxiv research on rhamnose biosynthesis​
• ASM journals on rhamnose exopolysaccharides​
• Bio-Rad quality control for rhamnose tests​
• SRL Chemicals D-Rhamnose data sheet​
• Himedia Labs product specification and storage​