By means of stable isotope dilution assays (SIDA), 26 odor-active compounds, previously characterized by GC-olfactometry (GC-O), were quantitated in raw peanuts, and the concentrations of 38 odorants were determined in pan-roasted peanut meal. On the basis of the quantitative data and odor thresholds determined in vegetable oil, the odor activity values (OAVs) of the most important aroma compounds in raw as well as in pan-roasted peanut meal were calculated. 3-Isopropyl-2-methoxypyrazine, acetic acid, and 3-(methylthio)propanal showed the highest OAVs in raw peanuts, whereas methanethiol, 2,3-pentanedione, 3-(methylthio)propanal, and 2- and 3-methylbutanal as well as the intensely popcorn-like smelling 2-acetyl-1-pyrroline revealed the highest OAV in the pan-roasted peanut meal. Aroma recombination studies confirmed the importance, in particular, of methanethiol and of lipid degradation products in the characteristic aroma of the freshly roasted peanut material. To evaluate additive effects on the overall aroma, the concentrations of eight pyrazines, previously not detected by GC-O among the odor-active volatiles, were additionally quantitated in the pan-roasted peanut meal. A sensory experiment in which the eight pyrazines were added to the recombinate clearly revealed that these volatiles did not show an impact on the overall aroma. Finally, selected odorants were quantitated in commercial peanut products to confirm their important role in peanut aroma.
On the basis of the recent findings that "biogenic amines" can also be formed during thermal food processing from their parent amino acids in a Strecker-type reaction, the formation of 3-aminopropionamide, the biogenic amine of asparagine, was investigated in model systems as well as in thermally processed Gouda cheese. The results of model studies revealed that, besides acrylamide, 3-aminopropionamide was also formed in amounts of 0.1-0.4 mol % when asparagine was reacted in the presence of either glucose or 2-oxopropionic acid. Results of a second series of model experiments in which [(13)C(4)(15)N(2)]-asparagine ([(13)C(4)(15)N(2)]-Asn) and unlabeled 3-aminopropionamide were reacted together in the presence of glucose revealed a >12-fold higher efficacy of 3-aminopropionamide in acrylamide generation as compared to asparagine. Both [(13)C(3)(15)N(2)]-3-aminopropionamide and [(13)C(3)(15)N(1)]-acrylamide were formed during [(13)C(4)(15)N(2)]-Asn degradation in a ratio of about 1:4, supporting the idea that 3-aminopropionamide is a transient intermediate in acrylamide formation. In this study, 3-aminopropionamide was identified and quantified for the first time in foods, namely, in Gouda cheese. Although the fresh cheese contained low amounts of 3-aminopropionamide, its concentrations were much increased to approximately 1300 mug/kg after thermal processing. In isotope labeling studies, performed by administering to the cheese [(13)C(4)(15)N(2)]-Asn in a ratio of 1:2 as compared to the "natural" concentrations of asparagine, similar ratios of unlabeled/labeled 3-aminopropionamide and unlabeled/labeled acrylamide were determined. Thus, 3-aminopropionamide could be verified as a transient intermediate of acrylamide formation during food processing.
3-Aminopropionamide (3-APA) has recently been suggested as a transient intermediate in acrylamide (AA) formation during thermal degradation of asparagine initiated by reducing carbohydrates or aldehydes, respectively. 3-APA may also be formed in foods by an enzymatic decarboxylation of asparagine. Using a newly developed method to quantify 3-APA based on liquid chromatography/tandem mass spectrometry, it could be shown that the biogenic amine was present in several potato cultivars in different amounts. Further experiments indicated that 3-APA is formed during storage of intact potatoes (20 or 35 degrees C) or after crushing of the cells. The heating of 3-APA under aqueous or low water conditions at temperatures between 100 and 180 degrees C in model systems always generated more AA than in the same reaction of asparagine, thereby pointing to 3-APA as a very effective precursor of AA. While the highest yields measured were about 28 mol % in the presence of carbohydrates (170 degrees C; aqueous buffer), in the absence of carbohydrates, 3-APA was even converted by about 63 mol % into AA upon heating at 170 degrees C under aqueous conditions. Propanoic acid amides bearing an amino or hydroxy group in the alpha-position, such as 2-hydroxypropionamide and l-alaninamide, were ineffective in AA generation indicating that elimination occurs only from the beta-position.
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