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thiosulfinate
In organosulfur chemistry, thiosulfinate is a functional group consisting of the linkage R-S(O)-S-R (R are organic substituents). Thiolsulfinates are also named as alkanethiosulfinic (or arenethiosulfinic) acid esters. They are the first member of a family of compounds containing an oxidized disulfide bond. Other members of this family include thiosulfonates, R-SO2-S-R, α-disulfoxides, R-S(O)-S(O)-R, sulfinyl sulfones, R-S(O)-SO2-R, and α-disulfones, R-SO2-SO2-R, all of which are known. The thiosulfinate group can occur in cyclic as well as acyclic structures.
==Occurrence==
A variety of acyclic and cyclic thiosulfinates are found in plants, or formed when the plants are cut or crushed. A well-known thiosulfinate is allicin, CH2=CHCH2S(O)SCH2CH=CH2, one of the active ingredients formed when garlic is crushed. Allicin was discovered in 1944 by Chester J. Cavallito and coworkers. 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. Crushing the roots of ''Petiveria alliacea'' affords the thiosulfinates ''S''-(2-hydroxyethyl) 2-hydroxyethane)thiosulfinate, ''S''-(2-hydroxylethyl) phenylmethanethiosulfinate, ''S''-benzyl 2-hydroxyethane)thiosulfinate and ''S''-benzyl phenylmethanethiosulfinate (petivericin; PhCH2S(O)SCH2Ph). Zeylanoxides are cyclic thiosulfinates containing the 1,2-dithiolane-1-oxide ring, isolated from the tropical weed ''Sphenoclea zeylanica''. These heterocyclic thiosulfinates are chiral at carbon as well as at sulfur. Asparagusic acid ''S''-oxide and brugierol are other natural 1,2-dithiolane-1-oxides occurring in ''Asparagus ocinalis'' and ''Brugiera conjugata'', respectively.
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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