Aroma properties of a homologous series of 2,3-epoxyalkanals and trans-4,5-epoxyalk-2-enals

Citation
A. Buettner et P. Schieberle, Aroma properties of a homologous series of 2,3-epoxyalkanals and trans-4,5-epoxyalk-2-enals, J AGR FOOD, 49(8), 2001, pp. 3881-3884
Citations number
18
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis
Journal title
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN journal
0021-8561 → ACNP
Volume
49
Issue
8
Year of publication
2001
Pages
3881 - 3884
Database
ISI
SICI code
0021-8561(200108)49:8<3881:APOAHS>2.0.ZU;2-5
Abstract
A few odor-active epoxyaldehydes, formed during lipid peroxidation, have re cently been reported as intense aroma compounds in foods. However, very lit tle is known about their flavor properties in general. Syntheses of homolog ous trans-2,3-epoxyalkanals (C-6-C-12) and trans-4,5-epoxy-(E)-2-alkenals ( C-7-C-12) followed by structural characterization using mass spectrometry ( MS/EI; MS/CI) and H-1 NMR measurements were performed. An evaluation of the ir odor qualities and odor thresholds by gas chromatography-olfactometry re vealed the following: within the trans-2,3-epoxyalkanals, the odor quality changed from grassy for the compounds with six and seven carbon atoms to ci trus-like or soapy for aldehydes with eight and more carbon atoms. The odor thresholds lay in the range of 3-15 ng/L (in air) and were nearly identica l within the series; however, a slight minimum was measured for trans-2,3-e poxyoctanal to trans-2,3-epoxydecanal. In the series of the trans-4,5-epoxy alk-(E)-2-enals the C-10 compound was characterized by the lowest odor thre shold of 0.6-2.5 pg/L of air. However, all trans-4,5-epoxy-alk-(E)-2-enals smelled intensely metallic.