7137-97-5Relevant articles and documents
Characterization of initial reaction intermediates in heated model systems of glucose, glutathione, and aliphatic aldehydes
Wang, Tianze,Zhen, Dawei,Tan, Jia,Xie, Jianchun,Cheng, Jie,Zhao, Jian
, (2019/09/12)
To understand the effect of lipid degradation on Maillard formation of meaty flavors, initial reaction intermediates in model systems of glucose–glutathione with hexanal, (E)-2-heptenal, or (E,E)-2,4-decadienal were identified by HPLC–MS and by NMR. Besides Amadori compounds, hemiacetals and thiazolidines via addition of sulfhydryl to carbonyl or to the conjugated olefinic bond were found. Concentrations of all intermediates increased with reaction time while degradation of the intermediates with a glutathione moiety helped formation of thiazolidines with cysteinylglycine. The unsaturated aldehydes (E)-2-heptenal and (E,E)-2,4-decadienal exhibited high reactivity against glucose for glutathione, yielding higher levels of intermediate compounds than from glucose. Heating prepared intermediates reversibly released the original aldehydes, which caused various compounds formed by retro-aldol, oxidation, etc. to react with H2S and NH3. Among them, formation pathways including 3-nonen-2-one, 2-hexanoylfuran, and six dialkylthiophenes (e.g., 2-ethyl-5-(1-methylbutyl)thiophene) were proposed for the first time.
Behaviour of N-pyridylbenzamides versus benzanilides in the ortho-directed lithiation of masked aromatic carboxylic acids
Jozwiak, Andrzej,Brzezinski, Jacek Z.,Plotka, Mieczyslaw W.,Szczesniak, Aleksandra K.,Malinowski, Zbigniew,Epsztajn, Jan
, p. 3254 - 3261 (2007/10/03)
The reaction of N-pyridylbenzamides 1-3 with n-butyllithium or sec-butyllithium has been examined. The perfect selectivity that has been observed until now in the lithiation of anilides, a reaction used for ortho-functionalisation of masked aromatic carboxylic acids, has been broken; our results indicate that the pyridine ring at the position ortho to the directed metallation group is more susceptible to lithiation than the homoaromatic ring itself. This was proved in an intermolecular comparative study of benz-, picolin- and isonicotinanilides 14-16, and N-cumylbenzamide (17). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.