Zur photometrischen Bestimmung primärer Amine mit Ninhydrin

Häntzsch, S.; Prescher, K.

doi:10.1007/bf00513592

Cited by 5 publications

(3 citation statements)

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“…Strecker degradation of amino acids is one of the most important reactions leading to final aroma compounds in the Maillard reaction ( , ). However, the results obtained in this study suggest that amines can also be degraded in a similar way, in accordance with previous studies showing that ninhydrin reacts with amines via a Strecker type transamination reaction ( , ). According to the obtained results, amine degradation produced by epoxyalkenals depended on the pH, the temperature, the amount of epoxyalkenal, and, mainly, the amine involved.…”

Section: Discussionsupporting

confidence: 93%

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Amine Degradation by 4,5-Epoxy-2-decenal in Model Systems

Zamora

Gallardo

Hidalgo

2006

J. Agric. Food Chem.

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The reactions of 4,5-epoxy-2-decenal with octylamine, benzylamine, and 2-phenylglycine methyl ester were studied to investigate if amines may suffer a Strecker type degradation by epoxyalkenals analogously to amino acids. In addition to other reactions, the studied amines were converted into their corresponding Strecker aldehydes (octanal, benzaldehyde, and methyl 2-oxo-2-phenylacetate, respectively) to an extent that depended on the pH, the temperature, the amount of epoxyalkenal, and the amine involved. Each amine exhibited an optimum pH for the reaction, but the corresponding Strecker aldehydes were produced to a significant extent within a broad pH range. In addition, the temperature mostly influenced the reaction rate, which was increased between 6.5 and 9.5 times when the reaction was carried out at 60 degrees C than when it took place at 37 degrees C. Furthermore, Strecker aldehyde formation was linearly correlated with the amount of the epoxyalkenal present in the reaction mixture. Nevertheless, the reaction yield mostly depended on the amine involved. Thus, octylamine only produced trace amounts of octanal, benzylamine was converted into benzaldehyde with a yield of 4.3%, and 2-phenylglycine methyl ester was converted into methyl 2-oxo-2-phenylacetate with a reaction yield of 49%. All of these results suggest that suitable amines can be degraded by epoxyalkenals to their corresponding Strecker aldehydes to a significant extent.

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Section: Discussionsupporting

confidence: 93%

“…The GC-MS (relative intensity, ion structure) of tentatively assigned compound 14 was 285 (23, M + ), 228 (18, M +butyl), 226 (24, M + -CO2CH3), 168 (100), 156 (14), 149 (18), 136 (16), 121 (60), 91 (28), 80 (19), and 77 (15).…”

Section: Methodsmentioning

confidence: 99%

Amine Degradation by 4,5-Epoxy-2-decenal in Model Systems

Zamora

Gallardo

Hidalgo

2006

J. Agric. Food Chem.

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“…The reduction in the intensity of the color measured spectrophotometrically was used for quantitative results but the loss in color had to be compared to known concentrations of the same amine. Hantzsch and Prescher (97) reacted microgram amounts of primary amines with ninhydrin and determined their concentrations spectrophotometrically. Amano (8) proposed reaction of primary aromatic amines with naphthalene-2,3dicarboxyaldehyde in strongly acidic medium to yield fluorescent products which were the basis of a quantitative procedure.…”

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confidence: 99%