54560-53-1Relevant academic research and scientific papers
Stopped-flow and spectrophotometric study on radical scavenging by tea catechins and the model compounds
Senba, Yasushi,Nishishita, Tsukasa,Saito, Kieko,Yoshioka, Hiroe,Yoshioka, Hisashi
, p. 1369 - 1374 (1999)
Radical scavenging of four tea catechins, (-)-epicatechin (EC), (-)- epigallocatechin (EGC), (-)-epicatechin gallate (ECg) and (-)- eppigallocatechin gallate (EGCg), and the model compounds of their partial structure was examined against the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical using stopped-flow and spectrophotometric methods. The number of DPPH radicals scavenged by a polyphenol molecule was larger than that of phenolic hydroxyl groups, suggesting that hydrogens which bond directly to the aromatic ring can also participate in radical scavenging. A model for the scavenging reaction was proposed in which the reaction proceeded with successive dehydrogenation from a polyphenol molecule. Analysis of the second order reaction rate constants and the activation parameters between DPPH and polyphenol at the early stage of the reaction showed that the values depended on the number of phenolic hydroxyl groups and their mutual position. Contribution of the A ring of catechins to the rate constants was estimated to be far smaller than that from the B ring. In the EGCg molecule, the B ring and the gallate group were not independent, but acted as a single group for DPPH radical scavenging.
The chain-breaking antioxidant activity of phenolic compounds with different numbers of O-H groups as determined during the oxidation of styrene
Tikhonov, Ivan,Roginsky, Vitaly,Pliss, Evgeny
experimental part, p. 92 - 100 (2009/06/28)
The technique based on monitoring oxygen, consumption was applied to test 18 polyphenols (PP) and model phenolics as a chain-breaking antioxidant during the oxidation of styrene initiated by 2,2′-azobis(2,4- dimethylvaleronitril) at 37°C. The chain-breaking capability of PP was characterized by two parameters: the rate constant k1 for the reaction of antioxidants with the peroxy radical produced from styrene and the stoichiometric coefficient of inhibition, f, which shows how many kinetic chains are terminated by one molecule of PP. Rate constants k1 × 105 (in M-1 s-1) were found to be 10 (catechol), 27 (pyrogallol), 34 (3,6-di-tert-Bucatechol), 4.3 (protocatechic acid), 12 (gallic acid), 15 (caffeic acid), 1 increases when going from one to two and three adjacent O-H groups in a benzene ring (catechol and pyrogallol derivatives, respectively). At the same time, two O-H. groups in metaposition in a A-ring of flavonoids actually do not participate in the inhibition. For the majority of PP, f is near to 2 independent of the number of OH groups. The correlation of k1 with the structure of PP and the O-H bond dissociation enthalpy has been discussed.
O-H Bond dissociation enthalpies in hydroxyphenols. A time-resolved photoacoustic calorimetry and quantum chemistry study
Correia, Catarina F.,Guedes, Rita C.,Borges Dos Santos, Rui M.,Costa Cabral, Benedito J.,Martinho Simoes, Jose A.
, p. 2109 - 2118 (2007/10/03)
Time-resolved photoacoustic calorimetry (TR-PAC) was used to investigate the energetics of O-H bonds of phenol, catechol, pyrogallol, and phloroglucinol. Values of -27.1 ± 3.9, -44.1 ± 4.4 and -1.6 ± 3.8 kJ mol-1, respectively, were obtained fo
