Preliminary results on 13C NMR studies regarding the radical scavenging activities of ascorbic acid and dihydroxyfumaric acid using 1,1-Diphenyl-2-picrylhydrazyl
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542.06:547.475.2+547.462.3 (1)
Chimie practică de laborator. Chimie de preparare și experimentală (135)
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GORINCIOI, Elena, VICOL, Crina, BARBA, Alic, DUKA, Gh.. Preliminary results on 13C NMR studies regarding the radical scavenging activities of ascorbic acid and dihydroxyfumaric acid using 1,1-Diphenyl-2-picrylhydrazyl. In: Ecological and environmental chemistry : - 2022, Ed. 7, 3-4 martie 2022, Chișinău. Chisinau: Centrul Editorial-Poligrafic al USM, 2022, Ediția 7, Vol.1, p. 64. ISBN 978-9975-159-07-4.. 10.19261/eec.2022.v1
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Ecological and environmental chemistry
Ediția 7, Vol.1, 2022
Conferința "Ecological and environmental chemistry 2022"
7, Chișinău, Moldova, 3-4 martie 2022

Preliminary results on 13C NMR studies regarding the radical scavenging activities of ascorbic acid and dihydroxyfumaric acid using 1,1-Diphenyl-2-picrylhydrazyl

CZU: 542.06:547.475.2+547.462.3

Pag. 64-64

Gorincioi Elena12, Vicol Crina1, Barba Alic1, Duka Gh.1
 
1 Institute of Chemistry,
2 Tiraspol State University
 
Proiecte:
 
Disponibil în IBN: 3 martie 2022


Rezumat

Dihydroxyfumaric acid (DHF) is a natural compound discovered in 1890s as an oxidation product of tartaric acid [1]. In small quantities it is found in grapes, being involved in the metabolism of the fruits during the ripening period [2]. Due to the ene-diol moiety, DHF exhibit nucleophilic and electrophilic character which support the ‖glioxylate scenario‖ [3], where DHF serves as a source molecule for the formation of a variety of biogenic molecules [4]. On the other hand, it was demonstrated that DHF possesses strong antioxidant activity against the free radical DPPH in alcoholic solvents and in wine matrix [5], having the antiradical power similar to that of ascorbic acid (AA). In virtue of the high reactivity of DHF, in aerobic conditions and in acidic media, it easily decarboxylates to form glycolaldehyde [6]. In extending our recent 13C NMR investigations of radical scavenging activities of two wine antioxidants: AA and resveratrol [7], the current study was aimed at finding of some potentially synergic interactions between DHF and AA, since both compounds can be found in grapes. We have used the analytical approach reported by Sawai et al., which employed 13C NMR spectroscopy in determining the properties of different tea polyphenols to regenerate each other [8]. The interactions of DHF and AA with free radical 1,1-Diphenyl-2-picrylhydrazyl (DPPH) were studied in the mixture of deuterated solvents acetone-d6 –methanol-d4 in the NMR tube. Three approaches of performing the reactions were considered, including different sequence of mixing antioxidant(s) and DPPH. The results of the exploratory studies show that neither AA nor DHF can be regenerated from their oxidized forms, in the case of DHF the decarboxylation due to the acidic media being hypothesized.