Thiosalicylic acid

Thiosalicylic acid

IUPAC name 2-Mercaptobenzoic acid
Systematic name 2-Sulfanylbenzoic acid^[1]
Other names o-Thiosalicylic acid
Identifiers
CAS number	147-93-3^Y
PubChem	5443
ChemSpider	5248^Y
EC number	205-704-3
KEGG	D08586^N
MeSH	2-Thiosalicylic+acid
ChEBI	CHEBI:59124^Y
ChEMBL	CHEMBL119888^Y
RTECS number	DH3325000
Beilstein Reference	508507
Gmelin Reference	3838
Jmol-3D images	Image 1 Image 2
SMILES OC(=O)C1=CC=CC=C1S SC1=C(C(O)=O)C=CC=C1
InChI InChI=1S/C7H6O2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H,(H,8,9)^Y Key: NBOMNTLFRHMDEZ-UHFFFAOYSA-N^Y
Properties
Molecular formula	C₇H₆O₂S
Molar mass	154.19 g mol⁻¹
Appearance	Leaf or needle shaped crystals
Density	1.49 g cm^-3^[2]
Melting point	162-169 °C, 435-442 K, 324-336 °F
log P	2.39
Acidity (pK_a)	3.501
Hazards
EU classification	Xi
R-phrases	R36/37/38
S-phrases	S26
Related compounds
Related compounds	Salicylic acid Thiophenol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

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

^ http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5443&loc=ec_rcs
^ "A13401 Thiosalicylic acid, 98%". Alfa Aesar. Retrieved 2010-08-10.
^ Lide, David R. (2009). Handbook of Chemistry and Physics (90 ed.). Boca Raton, Florida: CRC Press. p. 3-324. ISBN 978-1-4200-9084-0.
^ C. F. H. Allen and D. D. MacKay (1943), "Thiosalicylic acid", Org. Synth. ; Coll. Vol. 2: 580
^ Smalley, Keiran S.M; Tim G. Eisen (1). "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. |accessdate= requires |url= (help)
^ 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. |accessdate= requires |url= (help)

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

This page is available in 3 languages