3-Mercaptopropionic acid

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3-Mercaptopropionic acid
3-Mercaptopropionic acid.svg
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)
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, P261, 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[edit]

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]

See also[edit]

References[edit]

  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.