3-Mercaptopropionic acid - Misplaced Pages

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3-Mercaptopropionic acid
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
Density	1.218
Melting point	16.9 °C (62.4 °F; 290.0 K)
Boiling point	111 °C (232 °F; 384 K)
Solubility in water	soluble
Solubility	ether benzene alcohol water
Acidity (pK_a)	4.34
Refractive index (n_D)	1.4911 at 21 °C
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H290, H301, H314, H332
Precautionary statements	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 , 100 kPa). Infobox references

Chemical compound

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).

References

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. 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. doi:10.1002/anie.200903924. PMID 20166107.

GABATooltip γ-Aminobutyric acid metabolism and transport modulators

Transporter

GATTooltip GABA transporter	Inhibitors: 4-Aminovaleric acid β-Alanine Arecaidine CI-966 DABA Deramciclane (EGIS-3886, EGYT-3886) EF-1502 Gabaculine Guvacine Ibotenic acid Muscimol Nipecotic acid NNC 05-2090 NO-711 Riluzole SKF-89976A SNAP-5114 TACA Tiagabine
VIAATTooltip Vesicular inhibitory amino acid transporter	Inhibitors: β-Alanine Bafilomycin A1 Chicago sky blue 6B Evans blue GABA Glycine N-Butyric acid Nigericin Nipecotic acid Valinomycin Vigabatrin

Enzyme

GADTooltip Glutamate decarboxylase

Activators: 3-Methyl-GABA

GABA-TTooltip γ-Aminobutyrate aminotransferase

Inhibitors: 3-Hydrazinopropionic acid
DABA
γ-Acetylenic-GABA
AOAA
EOS
Gabaculine
Isoniazid
L-Cycloserine
Phenelzine
PEH
Rosmarinic acid (lemon balm)
Sodium valproate
Valnoctamide
Valproate pivoxil
Valproate semisodium (divalproex sodium)
Valproic acid
Valpromide
Vigabatrin

Activators: 3-Methyl-GABA

Other

Antivitamin B6	Ginkgotoxin

See also: Receptor/signaling modulators; GABA receptor modulators; GABA_A receptor positive modulators; Glutamate metabolism/transport modulators

Glutamate metabolism and transport modulators

Transporter

EAATsTooltip Excitatory amino acid transporters

vGluTsTooltip Vesicular glutamate transporters

Enzyme

GAHTooltip Glutamine aminohydrolase (glutaminase)	BPTES CB-839 DON
ASTTooltip Aspartate aminotransferase	2-Amino-3-butenoic acid AAOA AMB β-DL-Methylene-aspartate Hydrazinosuccinate
ALTTooltip Alanine aminotransferase	β-Chloro-L-alanine L-Cycloserine Propargylglycine
GDHTooltip Glutamate dehydrogenase	AAOA Bithionol Chloroquine EGCG GTP GW5074 Hexachlorophene Hydroxylamine Palmitoyl-CoA Pyridoxal phosphate
GSTooltip Glutamine synthetase	2-Aminoadipic acid JFD01307SC Methionine sulfoximine Phosphinothricin (glufosinate)
GADTooltip Glutamate decarboxylase	3-Mercaptopropionic acid AAOA L-Allylglycine Semicarbazide

See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Metabotropic glutamate receptor modulators • GABA metabolism and transport modulators

v t e Convulsants
GABA receptor antagonists	Bicuculline Bicyclic phosphates (TBPS, TBPO, IPTBO) BIDN Chlorophenylsilatrane Cicutoxin Cloflubicyne Coriamyrtin Dihydropicrotoxinin DMCM EBOB Endosulfan FG-7142 Fipronil Flurothyl Gabazine Oenanthotoxin Pentylenetetrazol Phenylsilatrane Picrotoxin p-CN-TBOB p-NCS-TBOB RDX TBOB Tetramethylenedisulfotetramine Thujone Trimethylolpropane phosphite Tutin
GABA synthesis inhibitors	3-Mercaptopropionic acid 4-Deoxypyridoxine Allylglycine Crimidine Decaborane Ginkgotoxin Isoniazid Pentaborane Thiocarbohydrazide Toxopyrimidine
Glycine receptor antagonists	Coriamyrtin Dendrobine Picrotoxin Strychnine Tutin
Glutamate receptor agonists	AMPA Domoic acid Kainic acid NMDA Quisqualic acid Tetrazolylglycine
Convulsant barbiturates	CHEB Diberal (DMBB) McN-481
Other	2,2,3,3-Tetrafluoropropyl trifluoromethyl ether Bromocamphor Camphor FAZ-4 Fluoroethyl fluoroacetate MC-2973 Methionine sulfoximine Methyl fluoroacetate Nitrocyclohexane Thebaine

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