Advances in Chemistry of Isothiocyanate-derived Colourants

K. Cejpek and J. Velíšek
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J. Velíšek: Department of Food Chemistry and Analysis, Institute of Chemical Technology in Prague, 66 28 Prague, Czech Republic

Czech Journal of Food Sciences, 2009, vol. 27, issue SpecialIssue1, S207-S210

Abstract: This study is focused on the reactions of isothiocyanates (ITCs) in the presence of amino compounds leading to coloured structures via substituted 2-thiohydantoins. A series of complementary experiments has been done and appropriate reaction conditions and structural prerequisites have been defined. Low-molecular colourants isolated and characterised from the model systems can be sorted into three groups. Yellow to red diastereomeric dehydrodimers of 2-thiohydantoin derivatives that contain an acidic methylene group are formed in mixtures consisted of ITCs and amino acids with α-methylene group in mild acidic to mild alkaline systems. The condensation products of the 2-thiohydantoins with reactive aromatic or heterocyclic carbaldehydes from the Maillard reaction, essential oils etc. comprise a heterogeneous group of mostly yellow colourants. Blue compounds of two types are structurally more complicated structures that arise from N-substituted amino acids and ITCs in alkaline media.

Keywords: isothiocyanates; amino acids; 2-thiohydantoins; carbaldehydes; colour; pigments (search for similar items in EconPapers)
Date: 2009
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Persistent link: https://EconPapers.repec.org/RePEc:caa:jnlcjf:v:27:y:2009:i:specialissue1:id:1092-cjfs

DOI: 10.17221/1092-CJFS

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