D-Gentiobiose

D-Gentiobiose

D-Gentiobiose (CAS No. 554-91-6) is a naturally occurring disaccharide made up of two D-glucose units joined by a β(1→6) glycosidic bond.nmpharmtech+2

Chemical Identity and Structure

• IUPAC Name: 6-O-β-D-Glucopyranosyl-D-glucose (beta-D-gluco-hexopyranosyl-(1→6)-beta-D-gluco-hexopyranose)pubchem.ncbi.nlm.nih+1
• Synonyms: β-Gentiobiose, Amygdalose, 6-(β-D-glucosido)-D-glucosedrugfuture+1
• Molecular Formula: C₁₂H₂₂O₁₁mycocentral+2
• Molecular Weight: 342.30 g/molchemicalbook+2
• Structure: Two D-glucose residues linked through a β(1→6) bondwikipedia+1
• SMILES: C(C1C(C(C(C(O1)OCC2C(C(C(C(O2)O)O)O)O)O)O)O)Omycocentral
• InChIKey: AYRXSINWFIIFAE-XUYRYHIXNA-Nchemicalbook

Physical and Chemical Properties

• Appearance: White to off-white crystalline powderwikipedia+1
• Melting Point: 195-197 °C (decomposes)chemicalbook
• Solubility: Sparingly soluble in water, soluble in hot methanolwikipedia+1
• Optical Activity: [α]D +21.4 → +8.7 (alpha); –11 → +9.6 (beta)chemicalbook
• Taste: Bitter; serves as a natural bittering agent in flavor sciencedrugfuture+1
• Hygroscopicity: Very hygroscopicdrugfuture

Biochemical and Industrial Significance

• Occurrence: Found in some natural products (such as crocin in saffron) and produced during starch hydrolysis or caramelization of glucose.wikipedia
• Production: Can be prepared enzymatically from D-glucose, or via partial hydrolysis of gentianose or other β-glucans.drugfuture+1
• Applications:

• • Used in biochemical research as a model compound for glycosylation and binding studies.nmpharmtech

  • Has roles in food, pharmaceutical, and cosmetic industries as a functional sweetener, raw material, and flavor modifier.nmpharmtech

  • Sometimes considered an undesirable byproduct (imparting bitterness) in glucose syrup and caramel manufacture.wikipedia

Storage and Handling

• Storage: Best stored sealed, in a dry environment at 2–8 °C.chemicalbook
• Stability: Stable when protected from moisture.chemicalbook

Regulatory and Identification Numbers

D-Gentiobiose is recognized for its biochemical utility, unique glycosidic linkage, and functional role in flavor and sugar chemistry research.nmpharmtech+2