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Amino acid-catalyzed conversion of citral : cis-trans isomerization and its conversion into 6-methyl-5-hepten-2-one and acetaldehyde

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Author: Wolken, W.A.M. · Have, R. ten · Werf, M.J. van der
Institution: Centraal Instituut voor Voedingsonderzoek TNO
Source:Journal of Agricultural and Food Chemistry, 11, 48, 5401-5405
Identifier: 41739
doi: doi:10.1021/jf0007378
Keywords: Nutrition · Videoconferencing · Internet · Data Conferencing · H.320


Under alkaline conditions, amino acids or proteins catalyze the deacetylation of citral, a major aroma component, resulting in methylheptenone and acetaldehyde formation. 3-Hydroxycitronellal is an intermediate in this reaction. Amino acids also catalyze the cis-trans isomerization of the pure isomers of citral, geranial, and neral. Most likely the amino acids are involved in stabilizing intermediates of the isomerization and deacetylation reaction of citral. On the basis of the findings presented, some consequences for the application of citral, or its isomers, in food are discussed. Chemicals/CAS: Acetaldehyde, 75-07-0; Amino Acids; citral, 5392-40-5; Ketones; methylheptenone, 110-93-0; Monoterpenes; Proteins; Terpenes