Thiomalic acid

(Redirected from Thiomalate)

Thiomalic acid or mercaptosuccinic acid is a dicarboxylic acid containing a thiol functional group. As suggested by its name, it contains a thiol group (SH) in place of the hydroxy group (OH) in malic acid. Salts and esters are known as thiomalates.

Thiomalic acid

D-Thiomalic acid
Names
Preferred IUPAC name
2-Sulfanylbutanedioic acid
Other names
2-Mercaptosuccinic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.670 Edit this at Wikidata
EC Number
  • 200-736-4
UNII
  • InChI=1S/C4H6O4S/c5-3(6)1-2(9)4(7)8/h2,9H,1H2,(H,5,6)(H,7,8) checkY
    Key: NJRXVEJTAYWCQJ-UHFFFAOYSA-N checkY
  • C(C(C(=O)O)S)C(=O)O
Properties
C4H6O4S
Molar mass 150.15 g·mol−1
Melting point 151 to 154 °C (304 to 309 °F; 424 to 427 K)
Related compounds
Other anions
Thiomalate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thiomalic acid is an intermediate in the synthesis of corrosion inhibitors, soil fumigants, active pharmaceutical ingredients, and electroplating agents.[1]

The sodium and gold salt of thiomalic acid, sodium aurothiomalate, is used as a pharmaceutical drug for the treatment of rheumatoid arthritis.[2]

Thiomalic acid forms the backbone of the pesticide malathion.

References

edit
  1. ^ "Thiomalic acid". Inxight Drugs. National Center for Advancing Translational Sciences.
  2. ^ Kean WF, Kean IR (June 2008). "Clinical pharmacology of gold". Inflammopharmacology. 16 (3): 112–25. doi:10.1007/s10787-007-0021-x. PMID 18523733. S2CID 808858.