3-Mercaptopropionic acid (3-MPA) is an organosulfur compound with the formula HSCH2CH2CO2H. It is a bifunctional molecule, containing both carboxylic acid and thiol groups. It is a colorless oil. It is derived from the addition of hydrogen sulfide to acrylic acid.

Reactions and uses

It is competitive inhibitor of glutamate decarboxylase, and therefore acts as a convulsant. It has higher potency and faster onset of action compared to allylglycine.[1]

It is used to prepare hydrophilic gold nanoparticles, exploiting the affinity of gold for sulfur ligands.[2]

It is esterified with polyols to form thiol-based polymer cross-linking agents such as pentaerythritol-based pentaerythritol tetrakis(3-mercaptopropionate).[3]

See also

References

  1. ^ Horton, R. W; Meldrum, B. S (1973). "Seizures induced by allylglycine, 3-mercaptopropionic acid and 4-deoxypyridoxine in mice and photosensitive baboons, and different modes of inhibition of cerebral glutamic acid decarboxylase". British Journal of Pharmacology. 49 (1): 52–63. doi:10.1111/j.1476-5381.1973.tb08267.x. PMC 1776427. PMID 4207045.
  2. ^ Subramanian, Vaidyanathan; Wolf, Eduardo E.; Kamat, Prashant V. (2004). "Catalysis with TiO2/Gold Nanocomposites. Effect of Metal Particle Size on the Fermi Level Equilibration". Journal of the American Chemical Society. 126 (15): 4943–4950. doi:10.1021/ja0315199. PMID 15080700.
  3. ^ Hoyle, Charles E.; Bowman, Christopher N. (2010). "Thiol–Ene Click Chemistry". Angewandte Chemie International Edition. 49 (9): 1542–1543. doi:10.1002/anie.200903924. PMID 20166107.