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Molecules 2015, 20(6), 10582-10593; doi:10.3390/molecules200610582

ŸKinetics of the Reaction of Pyrogallol Red, a Polyphenolic Dye, with Nitrous Acid: Role of Ÿ•NO and •NO2

1
Facultad de Química y Biología, Universidad de Santiago de Chile, Santiago 8320000, Chile
2
Departamento de Farmacia, Facultad de Química, Pontificia Universidad Católica de Chile, Santiago 7820436, Chile
3
Laboratorio de Fisicoquímica Biológica, Facultad de Ciencias and Center for Free Radical and Biomedical Research, Universidad de la República, Montevideo 11400, Uruguay
4
Cedenna, Universidad de Santiago de Chile, Santiago 8320000, Chile
*
Author to whom correspondence should be addressed.
Academic Editor: Claudio Battilocchio
Received: 7 April 2015 / Revised: 24 May 2015 / Accepted: 26 May 2015 / Published: 8 June 2015
(This article belongs to the Section Metabolites)
View Full-Text   |   Download PDF [853 KB, uploaded 8 June 2015]   |  

Abstract

In the present work we studied the reaction under gastric conditions of pyrogallol red (PGR), a polyphenolic dye, with nitrous acid (HONO). PGR has been used as a model polyphenol due to its strong UV-visible absorption and its high reactivity towards reactive species (radicals and non-radicals, RS). The reaction was followed by UV-visible spectroscopy and high performance liquid chromatography (HPLC). A clear decrease of the PGR absorbance at 465 nm was observed, evidencing an efficient bleaching of PGR by HONO. In the initial stages of the reaction, each HONO molecule nearly consumed 2.6 PGR molecules while, at long reaction times, ca. 7.0 dye molecules were consumed per each reacted HONO. This result is interpreted in terms of HONO recycling. During the PGR-HONO reaction, nitric oxide was generated in the micromolar range. In addition, the rate of PGR consumption induced by HONO was almost totally abated by argon bubbling, emphasising the role that critical volatile intermediates, such as ŸNO and/or nitrogen dioxide (ŸNO2), play in the bleaching of this phenolic compound. View Full-Text
Keywords: kinetics; nitrous acid; nitric oxide; nitrogen dioxide; pyrogallol red; phenols kinetics; nitrous acid; nitric oxide; nitrogen dioxide; pyrogallol red; phenols
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Hugo, E.; Reyes, J.; Montupil, E.; Bridi, R.; Lissi, E.; Denicola, A.; Rubio, M.A.; López-Alarcón, C. ŸKinetics of the Reaction of Pyrogallol Red, a Polyphenolic Dye, with Nitrous Acid: Role of Ÿ•NO and •NO2. Molecules 2015, 20, 10582-10593.

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