Thiosalicylic acid
| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name
2-Sulfanylbenzoic acid | |||
| Other names
2-Mercaptobenzoic acid (no longer recommended[1]) o-Thiosalicylic acid | |||
| Identifiers | |||
147-93-3  | |||
| 3D model (Jmol) | Interactive image Interactive image | ||
| 508507 | |||
| ChEBI | CHEBI:59124 | ||
| ChEMBL | ChEMBL119888 | ||
| ChemSpider | 5248 | ||
| ECHA InfoCard | 100.005.187 | ||
| EC Number | 205-704-3 | ||
| 3838 | |||
| KEGG | D08586  | ||
| MeSH | 2-Thiosalicylic+acid | ||
| PubChem | 5443 | ||
| RTECS number | DH3325000 | ||
| |||
| |||
| Properties | |||
| 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 | ||
| 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 | |||
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
- ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 697. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
The prefixes ‘mercapto’ (–SH), and ‘hydroseleno’ or selenyl (–SeH), etc. are no longer recommended.
- ↑ "A13401 Thiosalicylic acid, 98%". Alfa Aesar. Retrieved 2010-08-10.
- ↑ 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.
- ↑ C. F. H. Allen and D. D. MacKay (1943). "Thiosalicylic acid". Org. Synth.; Coll. Vol., 2, p. 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.
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