Acrolein in wine: importance of 3-hydroxypropionaldehyde and derivatives in production and detection.
Certain lactic acid bacteria strains belonging to the genus Lactobacillus have been implicated in the accumulation of 3-hydroxypropionaldehyde (3-HPA) during anaerobic glycerol fermentation. In aqueous solution 3-HPA undergoes reversible dimerization and hydration, resulting in an equilibrium state between different derivatives. Wine quality may be compromised by the presence of 3-HPA due to the potential for spontaneous conversion into acrolein under winemaking conditions. Acrolein is highly toxic and has been implicated in the development of bitterness in wine. Interconversion between 3-HPA derivatives and acrolein is a complex and highly dynamic process driven by hydration and dehydration reactions. Acrolein is furthermore highly reactive and its steady-state concentration in complex systems very low. As a result, analytical detection and quantification in solution is problematic. This paper reviews the biochemical and environmental conditions leading to accumulation of its precursor, 3-HPA. Recent advances in analytical detection are summarized, and the roles played by natural chemical derivatives are highlighted.
Bauer
Rolene
R
Institute for Microbial Biotechnology and Metagenomics, Department of Biotechnology, University of the Western Cape, Private Bag X17, Cape Town, South Africa. rbauer@uwc.ac.za
Cowan
Donald A
DA
Crouch
Andrew
A
D000171:Acrolein / Q000032:analysis* / Q000378:metabolism; D005285:Fermentation; D005985:Glyceraldehyde / Q000031:analogs & derivatives* / Q000032:analysis / Q000378:metabolism; D007778:Lactobacillus / Q000378:metabolism; D011407:Propane / Q000032:analysis* / Q000378:metabolism; D014920:Wine / Q000032:analysis* / Q000382:microbiology
C047158:3-hydroxypropionaldehyde; D005985:Glyceraldehyde; D000171:Acrolein; D011407:Propane