Abstract:
:The chemical interaction of 2,3-butanedione with amino acids through Strecker reaction has been studied extensively. However, the formation of previously reported 4,5-dimethyl-1,2-benzoquinone from 2,3-butanedione/amino acid model systems has not been investigated in detail. In this study such model systems containing 2,3-butanedione were investigated under pyrolytic conditions using glycine, sodium glycinate and glycine hydrochloride as amino acids able to modulate acid/base catalytic activity of the reaction medium. The analysis of the data indicated that replacing glycine with its corresponding salts promoted significantly the generation of 2,3,6,7-tetramethylquinoxaline relative to tetramethylpyrazine, the indicator compound for the Strecker reaction. The origin of the 2,3,6,7-tetramethylquinoxaline was traced back to the formation of 4,5-dimethyl-1,2-benzoquinone through isotope labelling studies. Furthermore, these studies have also indicated the ability of glycine not only to catalyse the cyclocondensation of butanedione into 4,5-dimethyl-1,2-benzoquinone but also its conversion into 4,5-dimethyl-1,2-phenylenediamine through Strecker-type transformations. The trapping of 2,3-butanedione by this in situ generated 4,5-dimethyl-1,2-phenylenediamine gave rise to the observed 2,3,6,7-tetramethylquinoxaline.
journal_name
Food Chemjournal_title
Food chemistryauthors
Guerra PV,Yaylayan VAdoi
10.1016/j.foodchem.2013.05.111subject
Has Abstractpub_date
2013-12-15 00:00:00pages
4391-6issue
4eissn
0308-8146issn
1873-7072pii
S0308-8146(13)00713-9journal_volume
141pub_type
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