Title: | Cinnamil- and Quinoxaline-Derivative Indicator Dyes for Detecting Volatile Amines in Fish Spoilage |
Address: | "Department of Food Science, University of Guelph, Guelph, ON N1G 2W1, Canada. xluo02@uoguelph.ca. Department of Food Science, University of Guelph, Guelph, ON N1G 2W1, Canada. llim@uoguelph.ca" |
DOI: | 10.3390/molecules24203673 |
ISSN/ISBN: | 1420-3049 (Electronic) 1420-3049 (Linking) |
Abstract: | "Colorimetric indicators are versatile for applications such as intelligent packaging. By interacting with food, package headspace, and/or the ambient environment, color change in these indicators can be useful for reflecting the actual quality and/or monitoring distribution history (e.g., time and temperature) of food products. In this study, indicator dyes based on cinnamil and quinoxaline derivatives were synthesized using aroma compounds commonly present in food: diacetyl, benzaldehyde, p-tolualdehyde and p-anisaldehyde. The identities of cinnamil and quinoxaline derivatives were confirmed by Fourier transform infrared (FT-IR) spectroscopy, mass spectrometry (MS), (1)H nuclear magnetic resonance (NMR) and (13)C NMR analyses. Photophysical evaluation showed that the orange-colored cinnamil derivatives in dimethylsulfoxide (DMSO) turned to dark brownish coloration when exposed to strong alkalis. The cinnamil and acid-doped quinoxaline derivatives were sensitive to volatile amines commonly present during the spoilage in seafood. Quinoxaline derivatives doped by strong organic acid were effective as pH indicators for volatile amine detection, with lower detection limits than cinnamil. However, cinnamil exhibited more diverse color profiles than the quinoxaline indicators when exposed to ammonia, trimethylamine, triethylamine, dimethylamine, piperidine and hydrazine. Preliminary tests of acid-doped quinoxaline derivatives on fresh fish demonstrated their potential as freshness indicators in intelligent packaging applications" |
Keywords: | Amines/chemistry/*isolation & purification Animals Benzaldehydes/chemistry Colorimetry Coloring Agents/*chemistry Diacetyl/chemistry Dimethyl Sulfoxide/chemistry Dimethylamines/chemistry Fishes Food/standards *Food Packaging Humans Hydrogen-Ion Concentrat; |
Notes: | "MedlineLuo, Xiaoyu Lim, Loong-Tak eng Switzerland 2019/10/17 Molecules. 2019 Oct 12; 24(20):3673. doi: 10.3390/molecules24203673" |