Thiomalic acid

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
Appearance white solid
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 or mercaptosuccinic acid is the organosulfur compound with the formula HO2CCH(SH)CH2CO2H. It 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. It is usually prepared by the addition of sulfur reagents (thiourea, hydrogen sulfide, etc.) to maleic anhydride. An enantioselective synthesis begins with aspartic acid via 2-bromosuccinic acid.

Uses

Thiomalic acid is a precursor to several medicinals in addition to the pesticide malathion.

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

References

  1. 1 2 Chen, Bang-Chi; Bednarz, Mark S.; Kocy, Octavian R.; Sundeen, Joseph E. (1998). "A new highly enantioselective synthesis of both (R)- and (S)-2-mercaptosuccinic acids". Tetrahedron: Asymmetry. 9 (10): 1641–1644. doi:10.1016/S0957-4166(98)00149-9.
  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.