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3-Mercaptopropionic acid

From Wikipedia, the free encyclopedia
3-Mercaptopropionic acid
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 InfoCard100.003.216Edit 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 mass106.14 g·mol−1
Density1.218
Melting point16.9 °C (62.4 °F; 290.0 K)
Boiling point111 °C (232 °F; 384 K) at 15 mmHg[1]
soluble
Solubilityether
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 theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

3-Mercaptopropionic acid (3-MPA) is anorganosulfur compound with the formula HSCH2CH2CO2H. It is abifunctional molecule, containing both carboxylic acid and thiol groups. It is a colorless oil. It is derived from the addition of hydrogen sulfide toacrylic acid.

Reactions and uses

[edit]

It is competitive inhibitor ofglutamate decarboxylase, and therefore acts as aconvulsant. It has higherpotency and fasteronset of action compared toallylglycine.[2]

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

It is esterified withpolyols to form thiol-basedpolymer cross-linking agents such aspentaerythritol-basedpentaerythritol tetrakis(3-mercaptopropionate).[4]

See also

[edit]

References

[edit]
  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.
GABATooltip γ-Aminobutyric acidmetabolism andtransportmodulators
Transporter
GATTooltip GABA transporter
VIAATTooltip Vesicular inhibitory amino acid transporter
Enzyme
GADTooltip Glutamate decarboxylase
GABA-TTooltip γ-Aminobutyrate aminotransferase
Other
Antivitamin B6
Transporter
EAATsTooltip Excitatory amino acid transporters
vGluTsTooltip Vesicular glutamate transporters
Enzyme
GAHTooltip Glutamine aminohydrolase (glutaminase)
ASTTooltip Aspartate aminotransferase
ALTTooltip Alanine aminotransferase
GDHTooltip Glutamate dehydrogenase
GSTooltip Glutamine synthetase
GADTooltip Glutamate decarboxylase
GABA receptor antagonists
GABA synthesis inhibitors
Glycine receptor antagonists
Glutamate receptor agonists
Convulsantbarbiturates
Other

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