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  |
| PubChem | 5443 |
| ChemSpider | 5248 |
| EC number | 205-704-3 |
| KEGG | D08586  |
| MeSH | 2-Thiosalicylic+acid |
| ChEBI | CHEBI:59124 |
| ChEMBL | CHEMBL119888 |
| RTECS number | DH3325000 |
| Beilstein Reference | 508507 |
| Gmelin Reference | 3838 |
| Jmol-3D images | Image 1 Image 2 |
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| 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 to 169 °C; 324 to 336 °F; 435 to 442 K |
| log P | 2.39 |
| Acidity (pKa) | 3.501 |
| Hazards | |
| EU classification |  Xi |
| R-phrases | R36/37/38 |
| S-phrases | S26 |
| Related compounds | |
| Related compounds | Salicylic acid |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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.
Other aspects
It is a precursor to drug candidates for treatment of atherosclerosis and melanoma.[5][6]
References
- ↑ 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 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.
- ↑ 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.