3-Mercaptopropionic acid

3-Mercaptopropionic acid
Names
Preferred IUPAC name
3-Sulfanylpropanoic acid
Other names
3-MPA; 3-Mercaptopropanoic acid; β-Mercaptopropionic acid
Identifiers
3D model (JSmol)
773807
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.216 Edit this at Wikidata
EC Number
  • 203-537-0
101294
UNII
  • InChI=1S/C3H6O2S/c4-3(5)1-2-6/h6H,1-2H2,(H,4,5)
    Key: DKIDEFUBRARXTE-UHFFFAOYSA-N
  • C(CS)C(=O)O
Properties
C3H6O2S
Molar mass 106.14 g·mol−1
Density 1.218
Melting point 16.9 °C (62.4 °F; 290.0 K)
Boiling point 111 °C (232 °F; 384 K) at 15 mmHg
soluble
Solubility ether
benzene
alcohol
water
Acidity (pKa) 4.34
1.4911 at 21 °C
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H290, H301, H314, H332
P234, P260, P264, P270, P271, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P390, P404, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

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

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

See also

References

  1. ↑ "PubChem".
  2. ↑ 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.
  3. ↑ 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. Bibcode:2004JAChS.126.4943S. doi:10.1021/ja0315199. PMID 15080700.
  4. ↑ Hoyle, Charles E.; Bowman, Christopher N. (2010). "Thiol–Ene Click Chemistry". Angewandte Chemie International Edition. 49 (9): 1542–1543. Bibcode:2010ACIE...49.1540H. doi:10.1002/anie.200903924. PMID 20166107.