Thiosalicylic acid

From Wikipedia, the free encyclopedia
  (Redirected from Thiosalicylate)
Jump to: navigation, search
Thiosalicylic acid
Skeletal formula of thiosalicylic acid
Space-filling model of thiosalicylic acid
Names
Preferred IUPAC name
2-Sulfanylbenzoic acid
Other names
2-Mercaptobenzoic acid (no longer recommended[1])
o-Thiosalicylic acid
Identifiers
3D model (JSmol)
{{{Beilstein}}}
ChEBI
ChemSpider
ECHA InfoCard 100.005.187
EC Number 205-704-3
{{{Gmelin}}}
KEGG
MeSH [www.nlm.nih.gov/cgi/show_data.php?acc={{{MeSH}}} {{{MeSH}}}]
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
Irritant Xi
R-phrases (outdated) R36/37/38
S-phrases (outdated) S26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).
N verify (what is YesYN ?)
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[edit]

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[edit]

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

References[edit]

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 697. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001. The prefixes ‘mercapto’ (–SH), and ‘hydroseleno’ or selenyl (–SeH), etc. are no longer recommended. 
  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.