Preparation, analysis and toxicity characterisation of the redox metabolites of the azo food dye tartrazine

Ruth Pay, Abigail V. Sharrock, Riley Elder, Alaigne Marie, Joe Bracegirdle, Dan Torres, Niall Malone, Jan Vorster, Libusha Kelly, Ali Ryan, P. David Josephy, Emma Allen-Vercoe, David F. Ackerley, Robert A. Keyzers, Joanne E. Harvey*

*Corresponding author for this work

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Abstract

Tartrazine (E102, FD&C Yellow 5) is a vibrant yellow azo dye added to many processed foods. The safety of this ubiquitous chemical has not been fully elucidated, and it has been linked to allergic reactions and ADHD in some individuals. In our study, bacterial species isolated from human stool decolourised tartrazine and, upon exposure to air, a purple compound formed. Tartrazine is known to undergo reduction in the gut to sulfanilic acid and 4-amino-3-carboxy-5-hydroxy-1-(4-sulfophenyl)pyrazole (SCAP). These metabolites and their derivatives are relevant to the toxicology of tartrazine. The toxicity of sulfanilic acid has been studied before, but the oxidative instability of SCAP has previously prevented full characterisation. We have verified the chemical identity of SCAP and confirmed that the purple-coloured oxidation derivative is 4-(3-carboxy-5-hydroxy-1-(4-sulfophenyl)-1H-pyrazol-4-yl)imino-5-oxo-1-(4-sulfophenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid (purpurazoic acid, PPA), as proposed by Westöö in 1965. A yellow derivative of SCAP is proposed to be the hydrolysed oxidation product, 4,5-dioxo-1-(4-sulfophenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid. Both SCAP and PPA are moderately toxic to human cells (IC50 89 and 78 μM against HEK-293, respectively), but had no apparent effect on Escherichia coli and Bacillus subtilis bacteria. These results prompt further analyses of the toxicology of tartrazine and its derivatives.
Original languageEnglish
Article number114193
Number of pages9
JournalFood and Chemical Toxicology
Volume182
Early online date18 Nov 2023
DOIs
Publication statusPublished - 1 Dec 2023

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