β-D-Glucose pentaacetate

 β-D-Glucose pentaacetate

β-D-Glucose pentaacetate (CAS No. 604-69-3) is a derivative of glucose that has been fully acetylated, making it a valuable compound in various biochemical and pharmaceutical applications. It is characterized by its ability to enhance the solubility and stability of hydrophobic compounds.

Chemical Properties

• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34 g/mol
• Boiling Point: 434.8 °C at 760 mmHg
• Melting Point: 130.0 to 134.0 °C
• Flash Point: 188.1 °C
• Density: 1.274 g/cm³
• Appearance: White to beige powder
• Optical Rotation: +5° (c=1, CHCl₃)
• Refractivity: 4.5° (C=5, CHCl₃)
• Storage Conditions: Store at 2–8 °C for long-term stability (months).

Applications

β-D-Glucose pentaacetate is widely utilized in several fields:

1. Biochemical Research:
   • Serves as a tool for studying carbohydrate metabolism and enzyme activity, aiding in the understanding of metabolic pathways in living organisms.
2. Drug Development:
   • Used as an active pharmaceutical intermediate, particularly in the synthesis of prodrugs that enhance bioavailability and therapeutic efficacy.
3. Food Industry:
   • Employed as a food additive to modify sweetness and stability, beneficial for flavor enhancement in food products.
4. Analytical Chemistry:
   • Utilized in chromatography and mass spectrometry for the analysis of sugars and other carbohydrates, providing precise identification and quantification.
5. Cosmetic Formulations:
   • Incorporated into cosmetic products for its emollient properties, improving texture and moisture retention in skincare formulations.
6. Insulin Release Stimulation:
   • β-D-Glucose pentaacetate has been shown to stimulate insulin release in rat pancreatic islets, making it relevant for studies related to diabetes.

Safety and Regulatory Status

β-D-Glucose pentaacetate is generally regarded as safe when used in appropriate applications; however, it should be handled with care due to its chemical properties.

Conclusion

β-D-Glucose pentaacetate is a versatile compound with significant applications across biochemical research, pharmaceuticals, food science, analytical chemistry, and cosmetics. Its ability to enhance solubility and stability makes it an essential tool in various scientific fields, contributing to advancements in drug development and metabolic studies.

Citations:

1. https://www.chemimpex.com/products/27076
2. https://www.fishersci.com/shop/products/beta-d-glucose-pentaacetate-98-thermo-scientific/AAA1252618
3. https://pubs.rsc.org/en/content/articlelanding/2023/nj/d2nj04673c
4. https://www.ottokemi.com/carbohydrate-synthesis/604-69-3.aspx
5. https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/60c7409ebb8c1a3c913d9de9/original/imidazole-promoted-efficient-anomerization-of-b-d-glucose-pentaacetate-in-organic-solutions-and-solid-state.pdf
6. https://pubchem.ncbi.nlm.nih.gov/compound/beta-D-glucose-pentaacetate
7. https://www.sigmaaldrich.com/IN/en/product/aldrich/285943
8. https://www.allgreenchems.com/info/the-applications-of-b-d-glucose-pentaacetate-92573018.html