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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:38705 ;
ChemSpider	6032 ;
ECHA InfoCard	100.000.670
EC Number	200-736-4;
PubChem CID	6268;
UNII	94239W5L4H ;
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) Key: NJRXVEJTAYWCQJ-UHFFFAOYSA-N ;
	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). verify (what is ?) Infobox references

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.^[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

^ "Thiomalic acid". Inxight Drugs. National Center for Advancing Translational Sciences.
^ 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.

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[1] "Thiomalic acid". Inxight Drugs. National Center for Advancing Translational Sciences.

[mech08-2] 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.

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