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.
Names | |
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Preferred IUPAC name
3-Sulfanylpropanoic acid | |
Other names
3-MPA; 3-Mercaptopropanoic acid; β-Mercaptopropionic acid | |
Identifiers | |
3D model (JSmol) |
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773807 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.216 |
EC Number |
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101294 | |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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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 |
Refractive index (nD) |
1.4911 at 21 °C |
Hazards | |
GHS labelling: | |
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).
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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
- Allylglycine
- Thiolactic acid (2-mercaptopropionic acid)
References
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