Thiosalicylic acid explained

Thiosalicylic acid is an organosulfur compound containing carboxyl and sulfhydryl functional groups. Its molecular formula is ortho-. It is a yellow solid that is slightly soluble in water, ethanol and diethyl ether, and alkanes, but more soluble in DMSO.

Preparation

Thiosalicylic acid can be prepared from anthranilic acid via diazotization followed by the addition of sodium sulfide and then reduction with zinc.[1]

Uses

Thiosalicylic acid is a precursor to the dyestuff thioindigo. It is also used to make the vaccine preservative thiomersal. It is a precursor to drug candidates for treatment of atherosclerosis and melanoma.[2] [3] The preservative benzisothiazolinone is prepared from thiosalicylic acid.

Notes and References

  1. C. F. H. Allen . D. D. MacKay . Thiosalicylic acid. 1932. 12. 76. 10.15227/orgsyn.012.0076. Organic Syntheses.
  2. Smalley. Keiran S.M.. Tim G. Eisen . Farnesyl thiosalicylic acid inhibits the growth of melanoma cells through a combination of cytostatic and pro-apoptotic effects. International Journal of Cancer. 1 April 2002. 98. 4. 514–522. 10.1002/ijc.10213. 11920610. 11196111.
  3. George. Jacob. Arnon Afek. Arnon Afek. Pnina Keren . Itzhak Herz . Iris Goldberg . Roni Haklai . Yoel Kloog . Gad Keren . Functional Inhibition of Ras by S-trans,trans-Farnesyl Thiosalicylic Acid Attenuates Atherosclerosis in Apolipoprotein E Knockout Mice. Circulation. 2002. 105. 20. 2416–2422. 10.1161/01.CIR.0000016065.90068.96. 12021230. free.

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