Isothiocyanate

Isothiocyanates are chemical compounds derived from the volatile isothiocyanic (also Isorhodanwasserstoff, HN = C = S ) can be derived. Organic isothiocyanates are called according to their natural occurrence and mustard oils ( see also mustard oil glycosides ).

One differentiates salt-like inorganic compounds M NCS and covalent organic compounds of general structure RN = C = S, such as methyl isothiocyanate, allyl isothiocyanate and sulforaphane.

Organic isothiocyanates are highly reactive compounds which react rapidly with various nucleophiles. With amines are formed, for example, substituted thioureas. Volatile isothiocyanates have a pungent odor and are lachrymatory and toxic.

Applications

Isothiocyanates deliver in the reaction with alcohols thiourethanes. In biochemistry, isothiocyanates can be used as part of an Edman degradation, to decompose proteins and peptides step by step in its components, the amino acids and thus to determine the amino acid sequence (sequence of amino acids in the peptide or protein). (1'- Cyanoisoindolyl ) phenyl isothiocyanate used - in this case be, for example, phenylisothiocyanate ( PITC ), 4- N, N- Dimethylaminoazobenzen -4' - isothiocyanate ( DABITC ) and 4. Isothiocyanate may be used for labeling and cross-linking of proteins and peptides, such as fluorescein isothiocyanate (FITC ) in the fluorescent label.

Occurrence

In nature, they are chemically bound primarily as glucosinolates in cruciferous vegetables before, such as in mustard (see above), white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, bok choy, kohlrabi, in the rutabaga, the radish / radishes, rape, horseradish, rocket and cress in the garden and in the Great nasturtium from the family of nasturtiums, and call there after cleavage from the glucosinolates produce the pungent taste.

Physiological effects

In various animal models was shown that isothiocyanates are able to inhibit chemically -induced carcinogenesis, a number of carcinogens. Cancer- preventive properties of some cruciferous plants are returned to the isothiocyanates therein.