The Formation of Furfural Compounds in Selected Saccharide- and Polysaccharide-based Pharmaceutical Excipients

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. © 2012 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 101:1811-1820, 2012