1,4-Anhydro-D-glucitol

1,4-Anhydro-D-glucitol, also known as 1,4-dideoxy-1,4-epoxy-D-glucitol, is a cyclic polyol derived from D-glucose by intramolecular dehydration of D-glucitol (sorbitol) between C-1 and C-4, forming an ether bridge. It retains several hydroxyl groups, making it highly water-soluble and non-reducing. Used as a bio-based platform chemical, it is a precursor of isosorbide and has applications in polymers, pharmaceuticals, osmoregulation, and cryoprotection. It serves as a valuable chiral building block for synthesizing complex molecules.

IUPAC Name 

• (3R,3aR,6R,6aR)-Hexahydrofuro[3,2-b]furan-3,6-diol

Appearance

•  White to off-white crystalline solid or powder

Source

• Synthetically derived via acidic dehydration of D-glucitol (sorbitol)
• Trace natural occurrences in plants and processed food products

Molecular Weight and Structure

• Molecular Weight: 164.16 g/mol
• Molecular Formula: C6H12O5
• Structure: Two fused five-membered tetrahydrofuran rings connected by an oxygen ether bridge with hydroxyl groups attached

Sugar Specificity

• Does not exhibit receptor-binding sugar specificity
• Used as chiral building block in synthesis

Biological Activity

• Investigated as osmotic diuretic and cryoprotectant
• Precursor to biologically important isosorbide

Purity and Microbial Contamination

• High purity required for chemical/pharmaceutical uses
• Purity confirmed by chromatography and NMR
• Microbial contamination controlled for pharmaceutical/food uses

Identity and Quality Control

• Confirmed by ^1H and ^13C NMR, mass spectrometry
• QC includes purity, impurities, water content (Karl Fischer), melting point, optical rotation

Shelf Life and Storage

• Stable for years if stored dry, protected from light, air
• Typically stored at room temperature or refrigerated

Application

• Precursor for isosorbide synthesis
• Cryoprotectant and osmotic diuretic candidate
• Chiral building block for pharmaceutical synthesis
• Polymer chemistry and sustainable bio-based materials

Citation 

• PubChem: https://pubchem.ncbi.nlm.nih.gov/compound/1_4-Anhydro-D-glucitol
• Sigma Aldrich: https://www.sigmaaldrich.com/US/en/product/aldrich/ph006861
• ChemicalBook: https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3466340.htm
• BenchChem: https://www.benchchem.com/product/b7795936