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Thiosalicylic acid

o-Thiosalicylic acid ortho-Thiosalicylic acid

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.

Applications

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. The preservative benzisothiazolinone is prepared from thiosalicylic acid.

Thiosalicylic acid is an excellent ligand, able to coordinate a very wide range of metals.

References

References

  1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. "A13401 Thiosalicylic acid, 98%". [[Alfa Aesar]].
  3. {{CRC90
  4. C. F. H. Allen. (1932). "Thiosalicylic acid". Organic Syntheses.
  5. Smalley, Keiran S.M.. (1 April 2002). "Farnesyl thiosalicylic acid inhibits the growth of melanoma cells through a combination of cytostatic and pro-apoptotic effects". International Journal of Cancer.
  6. George, Jacob. (2002). "Functional Inhibition of Ras by S-trans,trans-Farnesyl Thiosalicylic Acid Attenuates Atherosclerosis in Apolipoprotein E Knockout Mice". Circulation.
  7. (April 2016). "Coordination chemistry of the thiosalicylate ligand". Coordination Chemistry Reviews.
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