The formation of furfural compounds in selected saccharide- and polysaccharide-based pharmaceutical excipients

J Pharm Sci. 2012 May;101(5):1811-20. doi: 10.1002/jps.23072. Epub 2012 Feb 8.

Abstract

The acid hydrolysis of various selected saccharide- and polysaccharide-based pharmaceutical excipients under acid hydrolysis and the formation of degradation compounds were studied. New degradation products formed from these excipients were discovered. Liquid chromatography-mass spectrometry and nuclear magnetic resonance techniques were employed to identify and fully characterize these unknown compounds. The degradation products were identified as [(5-formylfuran-2-yl)methoxy]acetic acid, 5-[(propan-2-yloxy)methyl]furan-2-carbaldehyde, along with the previously identified 5-(methoxymethyl)furan-2-carbaldehyde. On the basis of the identification of these degradation products, a reasonable mechanism for their formation can be proposed. Temperature and pH affect the hydrolysis rates of saccharides and polysaccharides, which in turn affects the rate of formation of furfural compounds.

Publication types

  • Validation Study

MeSH terms

  • Carbohydrates / chemistry*
  • Chromatography, High Pressure Liquid
  • Excipients*
  • Furaldehyde / chemical synthesis*
  • Hydrogen-Ion Concentration
  • Hydrolysis
  • Kinetics
  • Limit of Detection
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Pharmaceutical Preparations / chemistry*
  • Polysaccharides / chemistry*
  • Reproducibility of Results
  • Temperature

Substances

  • Carbohydrates
  • Excipients
  • Pharmaceutical Preparations
  • Polysaccharides
  • Furaldehyde