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Open AccessArticle

Cinnamil- and Quinoxaline-Derivative Indicator Dyes for Detecting Volatile Amines in Fish Spoilage

Department of Food Science, University of Guelph, Guelph, ON N1G 2W1, Canada
Author to whom correspondence should be addressed.
Academic Editor: Daniel Cozzolino
Molecules 2019, 24(20), 3673;
Received: 10 September 2019 / Revised: 6 October 2019 / Accepted: 11 October 2019 / Published: 12 October 2019
(This article belongs to the Special Issue Food Analytical Chemistry–Advance Instrumental Methods and Sensors)
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), 1H nuclear magnetic resonance (NMR) and 13C 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. View Full-Text
Keywords: cinnamil; quinoxaline; indicator dye; amine detection; intelligent packaging cinnamil; quinoxaline; indicator dye; amine detection; intelligent packaging
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Luo, X.; Lim, L.-T. Cinnamil- and Quinoxaline-Derivative Indicator Dyes for Detecting Volatile Amines in Fish Spoilage. Molecules 2019, 24, 3673.

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