Chemistry:Thiomalic acid

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
EC Number	200-736-4
PubChem CID	6268
UNII	94239W5L4H Y
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).
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Infobox references

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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 is an intermediate in the synthesis of corrosion inhibitors, soil fumigants, active pharmaceutical ingredients, and electroplating agents.

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

Thiomalic acid forms the backbone of the pesticide malathion.