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3-Mercaptopropionic acid
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.
| Column 1 | Column 2 |
|---|---|
| Preferred IUPAC name | |
| 3-Sulfanylpropanoic acid | |
| Other names | |
| 3-MPA; 3-Mercaptopropanoic acid; β-Mercaptopropionic acid | |
| CAS Number | .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}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 | |
| 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 | etherbenzenealcoholwater |
| Acidity (pKa) | 4.34 |
| Refractive index (nD) | 1.4911 at 21 °C |
| 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.
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).
- Allylglycine
- Thiolactic acid (2-mercaptopropionic acid)
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