Thiomalic acid

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
CAS Number	70-49-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:38705 Y
ChemSpider	6032 Y
ECHA InfoCard	100.000.670
EC Number	200-736-4
PubChem CID	6268
UNII	94239W5L4H Y
CompTox Dashboard (EPA)	DTXSID20861615
InChI InChI=1S/C4H6O4S/c5-3(6)1-2(9)4(7)8/h2,9H,1H2,(H,5,6)(H,7,8) Y Key: NJRXVEJTAYWCQJ-UHFFFAOYSA-N Y
SMILES C(C(C(=O)O)S)C(=O)O
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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.