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Amino acid‐catalysed retroaldol condensation: the production of natural benzaldehyde and other flavour compounds
Author(s) -
Wolken Wout A. M.,
Tramper Johannes,
van der Werf Mariët J.
Publication year - 2004
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.1326
Subject(s) - chemistry , benzaldehyde , organic chemistry , condensation , amino acid , condensation reaction , catalysis , biochemistry , physics , thermodynamics
The amino acid‐catalysed retroaldol condensation previously described for citral has been extended to other α , β ‐unsaturated aldehydes. In the presence of glycine and an elevated pH, six other α , β ‐unsaturated aldehydes also underwent retroaldol condensation. Crotonaldehyde, as well as its proposed intermediate, aldol, were converted into acetaldehyde. Hexenal, decenal, methyl crotonaldehyde, farnesal and cinnamaldehyde were also converted into acetaldehyde plus butanal, octanal, acetone, geranyl acetone and benzaldehyde, respectively. Subsequently, the effects of temperature, pH, the buffer and substrate concentration on the conversion rate were studied, using the conversion of cinnamaldehyde into the important avour compound benzaldehyde as a model. Copyright © 2004 John Wiley & Sons, Ltd.