Thiosalicylic acid

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]

Thiosalicylic acid
Skeletal formula of thiosalicylic acid
Space-filling model of thiosalicylic acid
Names
Preferred IUPAC name
2-Sulfanylbenzoic acid[1]
Other names
2-Mercaptobenzoic acid
o-Thiosalicylic acid
ortho-Thiosalicylic acid
Identifiers
3D model (JSmol)
508507
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.187
EC Number
  • 205-704-3
3838
KEGG
MeSH 2-Thiosalicylic+acid
RTECS number
  • DH3325000
UNII
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
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R-phrases (outdated) R36/37/38
S-phrases (outdated) S26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 YN ?)
Infobox references

Preparation and uses

Thiosalicylic acid can be prepared from anthranilic acid via diazotization followed by the addition of sodium sulfide and then reduction with zinc.[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]

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References

  1. "Front Matter". 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.
  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". Organic Syntheses.; Collective Volume, 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. PMID 11920610.
  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 (20): 2416–2422. doi:10.1161/01.CIR.0000016065.90068.96.
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