Thiosulfinate

In organosulfur chemistry, thiosulfinate is a functional group consisting of the linkage R-S(O)-S-R (R refers to organic substituents).

Thiosulfinates containing various combinations of the methyl, n-propyl, 1-propenyl, 2-propenyl, n-butyl, 1-butenyl and 2-butenyl groups are formed upon crushing different Allium as well as Brassica species.

[6][7] Zeylanoxides are cyclic thiosulfinates containing the 1,2-dithiolane-1-oxide ring, isolated from the tropical weed Sphenoclea zeylanica.

Allicin, S-benzyl phenylmethanethiosulfinate, and related thiosulfinates show radical-trapping antioxidant activity associated with easy formation of sulfenic acids[12] The acyclic thiosulfinates from Allium and Brassica species possess antimicrobial, antiparasitic, antitumor and cysteine protease inhibitory activity while the natural 1,2-dithiolane-1-oxides are growth inhibitors.

This thiosulfinate can be obtained in optical purity by catalytic asymmetric oxidation of di-tert-butyl disulfide with hydrogen peroxide.

[18] In a similar manner racemic methyl methanethiosulfinate (CH3S(O)SCH3) can be obtained by peracetic acid oxidation of dimethyl disulfide.