Ethylthioacetic acid

Tirey et al. (1993) evaluated the degradation of phorate at three different temperatures. When oxidized at temperatures of 200, 250, and 275 °C, the following reaction products were identified by GC/MS ethanol, ethanethiol, methyl mercaptan, 1,2,4-trithiolane, 1,1-thiobisethane, 1,1 -(methylenebis(thio))bisethane, 1,3,5-trithiane, 0,0-diethyl-5-pentenyl phosphorodithioic acid, ethylthioacetic acid, diethyl disulfide, 2,2 -dithiobisethanol, ethyl-(1-methylpropyl) disulfide, sulfur dioxide, carbon monoxide, carbon dioxide, sulfuric acid, and phosphine. 

Triethylamine (1 g, 9.9 mmol) was added to a benzene solution of triphenylbismuth dibromide (1.2 g, 2 mmol) and ethylthioacetic acid (1.2 g, 5 mmol). After stirring for 1 h, the precipitated triethylamine hydrobromide was filtered off, and the filtrate was evaporated. The residue was recrystallized from acetonitrile to obtain the corresponding dicarboxylate (m.p. 119°C) [75JINC(37)2559]. 

The S atom of certain thioethers of cysteine and of related molecules were found to be oxidized in vivo to S04, e.g., iS-methyl-L-cysteine (68, 69), j8-hydroxyethylmethylsulfide, methyl- and ethylthioacetic acid (60). According to Binkley, the enzyme thionase cleaves /S-methyl-L-cysteine to methanethiol (61), which was shown to be oxidized to SO4 by Canellakis and Tarver (62). This may be a metabolic pathway for a variety of alky Ithiols of cysteine or thiolacetic acid. 

Brown and Scholefield (63) found that benzyl- and ethylthiopropionate, but not thiolacetate, are converted to benzyl mercaptan or ethanethiol, respectively. Guinea pig mitochrondia in vitro convert ethylthioacetic acid to the corresponding CoA derivative (64). 

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