Concerning the stability of benzyl alcohol: formation of benzaldehyde dibenzyl acetal under aerobic conditions

An impurity in benzyl alcohol was identified as benzaldehyde dibenzyl acetal (BDBA). The component BDBA is reversibly formed by the reaction of benzyl alcohol with benzaldehyde, an oxidative degradation product of benzyl alcohol. Whereas, BDBA is a known chemical entity, it is not typically controll...

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Bibliographic Details
Published in:Journal of pharmaceutical and biomedical analysis 2004-03, Vol.34 (5), p.957-962
Main Authors: Abend, Andreas M, Chung, Le, Bibart, Richard Todd, Brooks, Marvin, McCollum, David G
Format: Article
Language:English
Subjects:
Acetals - analysis
Acetals - chemistry
Acetals - metabolism
Aerobiosis - physiology
Analysis
Analytical, structural and metabolic biochemistry
Benzaldehyde dibenzyl acetal
Benzaldehydes - analysis
Benzaldehydes - chemistry
Benzaldehydes - metabolism
Benzyl alcohol
Benzyl Alcohol - analysis
Benzyl Alcohol - chemistry
Benzyl Alcohol - metabolism
Biological and medical sciences
Degradation product levels
Drug Contamination
Drug Stability
Excipients
Fundamental and applied biological sciences. Psychology
General pharmacology
Medical sciences
Pharmacology. Drug treatments
Reversed-phase chromatography
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Summary:An impurity in benzyl alcohol was identified as benzaldehyde dibenzyl acetal (BDBA). The component BDBA is reversibly formed by the reaction of benzyl alcohol with benzaldehyde, an oxidative degradation product of benzyl alcohol. Whereas, BDBA is a known chemical entity, it is not typically controlled in commercial benzyl alcohol since it cannot be formed in the absence of benzaldehyde, which is itself generally controlled. However, once commercial benzyl alcohol is exposed to the atmosphere, formation of BDBA is possible. The synthesis and characterization of BDBA is reported. The ability of BDBA to react with alcohols to form other types of acetals, and the impact of low levels of BDBA on the quantitative analysis of pharmaceutical products, are considered.
ISSN:0731-7085
1873-264X
DOI:10.1016/j.jpba.2003.11.007