L-Glucose

L-Glucose

L-Glucose (CAS No. 921-60-8) is the enantiomer of the naturally abundant D-glucose, characterized as an aldohexose sugar with the molecular formula C6H12O6 and molecular weight of 180.16 g/mol.chemicalbook+1

Chemical Identity and Structure

• IUPAC Name: L-gluco-hexose, specifically the L-enantiomer of D-glucose.pubchem.ncbi.nlm.nih+1
• Synonyms: L-(-)-Glucose, Levoglucose, α-L-glucopyranose, laevo-glucose.tcichemicals+1
• Molecular Formula: C6H12O6.chemscene+1
• Molecular Weight: 180.16 g/mol.chemscene
• Structure: L-Glucose is the mirror image (enantiomer) of D-glucose, differing in the stereochemistry at every chiral center.wikipedia

Physical and Chemical Properties

• Appearance: White to almost white crystalline powder.tcichemicals
• Melting Point: 153–156 °C (literature).chemicalbook
• Boiling Point: Approx. 233 °C (estimated).chemicalbook
• Solubility: Soluble in water and alcohols; approximately 0.1 g/mL in water, clear and colorless solution.tcichemicals+1
• Optical Rotation: Approximately -52° (c = 5, H2O).chemicalbook+1
• Stability: Stable under recommended storage conditions; incompatible with strong oxidizers.chemicalbook

Biological and Functional Notes

• Metabolic Activity: L-Glucose is not metabolized by common cellular pathways since hexokinase cannot phosphorylate it, making it non-bioavailable as an energy source.wikipedia+1
• Rare Usage: It has experimental uses, including investigation of sugar transporters and bacterial L-glucose metabolism in rare bacteria with specific dehydrogenases.chemicalbook
• Applications: L-Glucose derivatives like L-glucose pentaacetate have therapeutic potential in type 2 diabetes; L-Glucose is also investigated as a colon cleansing agent for medical prep without altering fluid balance significantly.wikipedia

Storage and Handling

• Storage Conditions: Store in a cool, dark place, preferably below 15°C; some sources recommend 2-8°C; keep sealed to avoid hygroscopic moisture absorption.tcichemicals+1

Identification Numbers and References

L-Glucose is primarily used in research settings for biochemical studies and as a probe sugar due to its unique stereochemistry and lack of metabolic conversion in most organisms.wikipedia+2