3-Mercaptopropionic acid

3-Mercaptopropionic acid
	source ↗
Names
	Preferred IUPAC name 3-Sulfanylpropanoic acid
	Other names 3-MPA; 3-Mercaptopropanoic acid; β-Mercaptopropionic acid
Identifiers
CAS Number	107-96-0;
3D model (JSmol)	Interactive image;
Beilstein Reference	773807
ChEBI	CHEBI:44111;
ChEMBL	ChEMBL358697;
ChemSpider	6267;
ECHA InfoCard	100.003.216
EC Number	203-537-0;
Gmelin Reference	101294
PubChem CID	6514;
UNII	B03TJ3QU9M;
CompTox Dashboard (EPA)	DTXSID8026775 ;
	InChI InChI=1S/C3H6O2S/c4-3(5)1-2-6/h6H,1-2H2,(H,4,5) Key: DKIDEFUBRARXTE-UHFFFAOYSA-N;
	SMILES C(CS)C(=O)O;
Properties
Chemical formula	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
Solubility in water	soluble
Solubility	ether; benzene; alcohol; water
Acidity (pKa)	4.34
Refractive index (nD)	1.4911 at 21 °C
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H290, H301, H314, H332
Precautionary statements	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). Infobox references

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.²

It is used to prepare hydrophilic gold nanoparticles, exploiting the affinity of gold for sulfur ligands.³

It is esterified with polyols to form thiol-based polymer cross-linking agents such as pentaerythritol-based pentaerythritol tetrakis(3-mercaptopropionate).⁴

References

"PubChem".
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.
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.
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.

[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.

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Reactions and uses

See also

References