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.
ZENTIVA, a.s. Praha, 102 37 Prague 10, Czech Republic. michal.dousa@seznam.cz
Michal
M
Douša
Petr
P
Gibala
Jiří
J
Břicháč
Jaroslav
J
Havlíček
D002241:Carbohydrates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005079:Excipients; D005662:Furaldehyde / Q000138:chemical synthesis*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007700:Kinetics; D057230:Limit of Detection; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D004364:Pharmaceutical Preparations / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry*; D015203:Reproducibility of Results; D013696:Temperature
D002241:Carbohydrates; D005079:Excipients; D004364:Pharmaceutical Preparations; D011134:Polysaccharides; D005662:Furaldehyde