Thiosalicylic acid

Thiosalicylic acid

Names
IUPAC name 2-Mercaptobenzoic acid
Systematic IUPAC name 2-Sulfanylbenzoic acid[1]
Other names o-Thiosalicylic acid
Identifiers
CAS Number	147-93-3
Beilstein Reference	508507
ChEBI	CHEBI:59124
ChEMBL	ChEMBL119888
ChemSpider	5248
EC Number	205-704-3
Gmelin Reference	3838
Jmol interactive 3D	Image Image
KEGG	D08586
MeSH	2-Thiosalicylic+acid
PubChem	5443
RTECS number	DH3325000
InChI InChI=1S/C7H6O2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H,(H,8,9) Key: NBOMNTLFRHMDEZ-UHFFFAOYSA-N
SMILES OC(=O)C1=CC=CC=C1S SC1=C(C(O)=O)C=CC=C1
Properties
Chemical formula	C7H6O2S
Molar mass	154.18 g·mol^−1
Appearance	Leaf or needle shaped crystals
Density	1.49 g cm^−3[2]
Melting point	162 to 169 °C (324 to 336 °F; 435 to 442 K)
log P	2.39
Acidity (pKa)	3.501
Hazards
EU classification (DSD)	Xi
R-phrases	R36/37/38
S-phrases	S26
Related compounds
Related compounds	Salicylic acid Thiophenol
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

Thiosalicylic acid is an organosulfur compound containing carboxyl and sulfhydryl functional groups. Its molecular formula is C₆H₄(SH)(CO₂H). it is a yellow solid that is slightly soluble in water, ethanol and diethyl ether, and alkanes, but more soluble in DMSO.^[3]

Preparation and uses

Thiosalicylic acid is prepared from 2-aminobenzoic acid via diazotization.^[4]

Thiosalicylic acid is a precursor to the dyestuff thioindigo. Thiosalicylic acid is also used to make the vaccine preservative thiomersal.

Other aspects

It is a precursor to drug candidates for treatment of atherosclerosis and melanoma.^[5][6]

References

1. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5443&loc=ec_rcs
2. "A13401 Thiosalicylic acid, 98%". Alfa Aesar. Retrieved 2010-08-10.
3. Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. p. 3-324. ISBN 978-1-4200-9084-0.
4. C. F. H. Allen and D. D. MacKay (1943). "Thiosalicylic acid". Org. Synth.; Coll. Vol. 2, p. 580
5. Smalley, Keiran S.M; Tim G. Eisen (1 April 2002). "Farnesyl thiosalicylic acid inhibits the growth of melanoma cells through a combination of cytostatic and pro-apoptotic effects". International Journal of Cancer 98 (4): 514–522. doi:10.1002/ijc.10213.
6. George, Jacob; Arnon Afek; Pnina Keren; Itzhak Herz; Iris Goldberg; Roni Haklai; Yoel Kloog; Gad Keren (2002). "Functional Inhibition of Ras by S-trans,trans-Farnesyl Thiosalicylic Acid Attenuates Atherosclerosis in Apolipoprotein E Knockout Mice". Circulation 105: 2416–2422. doi:10.1161/01.CIR.0000016065.90068.96.