Abstract:
:The epithionitriles, 1-cyano-2,3-epithiopropane, in particular, and 1-cyano-3,4-epithiobutane, are important, but yet underestimated glucosinolate hydrolysis products that are released instead of the cancer preventative isothiocyanates in Brassica vegetables, such as cabbage, broccoli, or pak choi. Here, we characterized the reactivity of 1-cyano-2,3-epithiopropane under aqueous heat treatment conditions and compared our findings to those of the related epithionitriles 1-cyano-3,4-epithiobutane and 1-cyano-4,5-epithiopentane. In contrast to the other epithionitriles, 1-cyano-2,3-epithiopropane is highly reactive. As a result, 2-aminothiophene and dimeric 1,4-dithiane-2,5-diacetonitrile were identified as main products and a reaction mechanism is proposed. Formation of 2-aminothiophene was also observed in cooked white cabbage samples. Moreover, three novel compounds were identified as derivatives of the related epithionitriles. The results imply that apart from isothiocyanates, process-derived compounds should be considered in regards to cancer preventative Brassica vegetable related bioactivity.
journal_name
Food Chemjournal_title
Food chemistryauthors
Hanschen FS,Kaufmann M,Kupke F,Hackl T,Kroh LW,Rohn S,Schreiner Mdoi
10.1016/j.foodchem.2017.10.124subject
Has Abstractpub_date
2018-04-15 00:00:00pages
564-569eissn
0308-8146issn
1873-7072pii
S0308-8146(17)31771-5journal_volume
245pub_type
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