Ethyl β-D-glucopyranoside

Ethyl β-D-glucopyranoside is a synthetically produced glycoside of D-glucose, where the anomeric hydroxyl group is replaced by an ethyl group in the β-configuration. This compound is a white crystalline solid, prized in carbohydrate chemistry for its enhanced stability, resistance to mutarotation, and suitability as a non-reducing sugar derivative. It has a molecular formula of C8H16O6 and a molecular weight of 208.21 g/mol. The ethyl group at C1 restricts its reactivity, yet the β-D-glucopyranoside ring structure preserves selective recognition by carbohydrate-processing enzymes and proteins. It is usually synthesized by acid-catalyzed glycosylation of D-glucose with ethanol, followed by rigorous purification, ensuring high purity (≥98%) and absence of microbial contamination. Ethyl β-D-glucopyranoside is widely utilized as an intermediate in synthetic oligosaccharide pathways, a substrate or reference for enzyme assays, and a building block for glycomimetics and sugar-based functional materials. Identity is typically confirmed via NMR, MS, and HPLC, and each batch is quality-controlled with COA documentation. The compound’s shelf life is 1–2 years under dry, cool (2–8 °C), and light-protected storage. Applications include chemical synthesis, biochemical research, physiological studies, and carbohydrate-based pharmaceutical development.

IUPAC Name:

• Ethyl β-D-glucopyranoside

Appearance:

• White crystalline powder

Source:

• Synthesized from D-glucose via acid-catalyzed glycosylation with ethanol, followed by purification under sterile laboratory conditions

Molecular Weight and Structure:

• Molecular formula: C8H16O6
• Molecular weight: 208.21 g/mol
• Structure: β-D-glucopyranose ring with ethyl group substituting the anomeric hydroxyl; four free hydroxyl groups at C2, C3, C4, C6
  SMILES: CCOC1C(C(C(C(O1)O)O)O)O

Sugar Specificity:

• β-anomer of D-glucopyranoside; recognized by many β-glucosidases and carbohydrate-binding proteins

Biological Activity:

• Chemically stable, non-reducing sugar derivative; serves as a substrate analog in enzymatic activity assays and glycomimetic studies; limited direct pharmacological activity but used for bioactivity modeling

Purity and Microbial Contamination:

• Purity ≥98%, verified with NMR, MS, and HPLC; made under aseptic conditions to ensure negligible microbial contamination

Identity and Quality Control:

• Identity confirmed via NMR (1H/13C), mass spectrometry, HPLC; melting point and optical rotation ways for batch consistency; accompanied by COA and SDS

Shelf Life and Storage:

• Stable for 1–2 years when stored sealed, dry, and cool at 2–8 °C; protect from moisture and light exposure

Application:

• Used in synthetic oligosaccharide chemistry, as a control or substrate in enzyme assays, a scaffold for glycomimetic assembly, and to investigate carbohydrate recognition or metabolism in physiological studies

Key Characteristics:

• Ethyl β-D-glucopyranoside, non-reducing sugar
• CAS 453-20-3
• Molecular weight: 208.21 g/mol
• White crystalline, high-purity, chemically stable
• Selective for β-D-glucopyranosyl recognition sites
• Full quality documentation, batch identity verified
• Stable under proper laboratory conditions
• Used broadly in synthetic and biochemical carbohydrate research

Citations:

• ChemicalBook compound info
• TCIChemicals supplier info
• AnaxLab catalog
• Sigma-Aldrich synthetic reference
• PubChem chemistry data
• MedChemExpress carbohydrates
• Synthose glycosylation intermediates
• ScienceDirect carbohydrate chemistry
• Patent literature for ethyl glycosides
• Benchchem product