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Bioinspired Synthesis and Physical-Chemical Properties of a New 10-Methylpyrano-4 '-hydroxyflavylium Chloride Salt

Title
Bioinspired Synthesis and Physical-Chemical Properties of a New 10-Methylpyrano-4 '-hydroxyflavylium Chloride Salt
Type
Article in International Scientific Journal
Year
2020
Authors
Gomes, V
(Author)
Other
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Guimaraes, M
(Author)
Other
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Goncalves, G
(Author)
Other
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Victor de Freitas
(Author)
FCUP
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Luis Cruz
(Author)
FCUP
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Journal
Title: SynlettImported from Authenticus Search for Journal Publications
Vol. 31
Pages: 334-338
ISSN: 0936-5214
Publisher: Thieme
Other information
Authenticus ID: P-00R-SS8
Abstract (EN): A novel bioinspired 10-methylpyranoflavylium dye was synthesized. The dye was fully characterized by LC-DAD/ESI-MS and NMR 1D and 2D techniques, and its equilibrium constants towards pH variations were determined by UV-vis titration. These studies revealed the presence of three species (a flavylium cation AH(+) , a neutral quinoidal base A, and an anionic quinoidal base A(-)) in the pH range 1-12, driven by the two pK(a)values of the dye: pK(a1)= 6.8 +/- 0.1 and pK(a2)= 10.8 +/- 0.1. The first deprotonation of the dye occurs within the pH range for spoilage of many packed-food products, making the dye an excellent candidate for use as a pH sensor for real-time monitoring of the quality and freshness of foods.
Language: English
Type (Professor's evaluation): Scientific
No. of pages: 5
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