Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C4H4O4S.Na.H |
| Molecular Weight | 172.135 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H+].[Na+].[O-]C(=O)CC(S)C([O-])=O
InChI
InChIKey=WGIKUIATRROGSN-UHFFFAOYSA-M
InChI=1S/C4H6O4S.Na/c5-3(6)1-2(9)4(7)8;/h2,9H,1H2,(H,5,6)(H,7,8);/q;+1/p-1
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C4H5O4S |
| Molecular Weight | 149.145 |
| Charge | -1 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
A thiomalic acid or mercaptosuccinic acid is a dicarboxylic acid containing a thiol functional group. Mercaptosuccinic acid is used in the preparation of mercaptosuccinic acid diethyl ester by reaction with ethanol. It is also used as a brightening agent in metal plating. Further, it serves as an intermediate for the synthesis of corrosion inhibitors, soil fumigants, active pharmaceutical ingredients and electroplating agents. Mercaptosuccinic acid is widely used in the synthesis of various biologically active sulfur containing compounds such as the antileukemic spiro[indoline-3,2'-thiazolidine]-2,4'-diones, and the antimicrobial and antitubercular 4-thiazolidinones. It is also used as a building block in the synthesis of novel polyanionic inhibitors of human immunodeficiency virus and other viruses, and as a starting material in the synthesis of isocysteine, an important non-proteinogenic amino acid in a potent peptide inhibitor of stromelysin. In addition, sodium salt of the anionic Au(I) complex of 2-mercaptosuccinic acid is an effective antiarthritic drug.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Resveratrol attenuates apoptosis of pulmonary microvascular endothelial cells induced by high shear stress and proinflammatory factors. | 2011-09 |
|
| The gender-dependent difference of liver GSH antioxidant system in mice and its influence on isoline-induced liver injury. | 2011-02-04 |
|
| Ag(9) quantum cluster through a solid-state route. | 2010-11-24 |
|
| Cysteine protects freshly isolated cardiomyocytes against oxidative stress by stimulating glutathione peroxidase. | 2010-10 |
|
| Luminescent quantum clusters of gold in bulk by albumin-induced core etching of nanoparticles: metal ion sensing, metal-enhanced luminescence, and biolabeling. | 2010-09-03 |
|
| Fluorescent carbon dots capped with PEG200 and mercaptosuccinic acid. | 2010-09 |
|
| Poly[[μ(3)-chlorido-bis(μ(2)-thio-urea-κS)disilver(I)] nitrate]. | 2010-08-11 |
|
| An amperometric immunosensor based on a polyelectrolyte/gold magnetic nanoparticle supramolecular assembly--modified electrode for the determination of HIV p24 in serum. | 2010-07-23 |
|
| Antibacterial nitric oxide-releasing polyester for the coating of blood-contacting artificial materials. | 2010-07 |
|
| Gold nanoparticle membranes as large-area surface monolayers. | 2010-06-01 |
|
| Aqueous synthesis and fluorescence-imaging application of CdTe/ZnSe core/shell quantum dots with high stability and low cytotoxicity. | 2010-03 |
|
| Regulation of the protein-loading capacity of hydroxyapatite by mercaptosuccinic acid modification. | 2010-03 |
|
| Expression of tyrosine hydroxylase increases the resistance of human neuroblastoma cells to oxidative insults. | 2010-01 |
|
| catena-Poly[4,4'-bipyridinium [[diaqua-disulfatocadmium(II)]-μ-4,4'-bipyridine-κN:N'] dihydrate]. | 2009-12-12 |
|
| Electrochemical quartz crystal microbalance study of covalent tethering of carboxylated thiol to polyaniline for electrocatalyzed oxidation of ascorbic acid in neutral aqueous solution. | 2009-10-28 |
|
| H(2)O(2)-mediated modulation of cytosolic signaling and organelle function in rat hippocampus. | 2009-09 |
|
| Methylmercury neurotoxicity is associated with inhibition of the antioxidant enzyme glutathione peroxidase. | 2009-08-15 |
|
| Synthesis of coumarin heterocyclic derivatives with antioxidant activity and in vitro cytotoxic activity against tumour cells. | 2009-06 |
|
| Imaging pancreatic cancer using bioconjugated InP quantum dots. | 2009-03-24 |
|
| Synthesis and antihyperglycemic activity of 2-(substituted phenyl)-3-{[4-(1-naphthyl)-1,3-thiazol-2-yl] amino}-4-oxo-1,3-thiazolidin-5-ylacetic acid derivatives. | 2009-02-21 |
|
| Oxidative stress in stroke pathophysiology validation of hydrogen peroxide metabolism as a pharmacological target to afford neuroprotection. | 2009 |
|
| [Role of glycolysis and antioxidant enzymes in the toxicity of amyloid beta peptide Abeta25-35 to erythrocytes]. | 2008-12-09 |
|
| Photoelectrochemical signal chain based on quantum dots on gold--sensitive to superoxide radicals in solution. | 2008-10-15 |
|
| Tanshinone IIA reduces macrophage death induced by hydrogen peroxide by upregulating glutathione peroxidase. | 2008-10-10 |
|
| Synthesis of CdTe nanocrystals with mercaptosuccinic acid as stabilizer. | 2008-09 |
|
| AMPA receptor-dependent H2O2 generation in striatal medium spiny neurons but not dopamine axons: one source of a retrograde signal that can inhibit dopamine release. | 2008-09 |
|
| Oxidative alterations induced by D-aspartic acid in prepubertal rat testis in vitro: a mechanistic study. | 2008-07-01 |
|
| A unique family of stable and water-soluble S-nitrosothiol complexes. | 2008-06-02 |
|
| Synthesis and bio-imaging application of highly luminescent mercaptosuccinic acid-coated CdTe nanocrystals. | 2008-05-21 |
|
| catena-Poly[[tetra-aqua-(μ-4,4'-bipyridine-κN:N')zinc(II)] fumarate tetra-hydrate]. | 2008-04-16 |
|
| Identification of bismuth-thiolate-carboxylate clusters by electrospray ionization mass spectrometry. | 2008-04-07 |
|
| Preparation of gold nanoparticles in an aqueous medium using 2-mercaptosuccinic acid as both reduction and capping agent. | 2008-04 |
|
| Antithrombogenic polynitrosated polyester/poly(methyl methacrylate) blend for the coating of blood-contacting surfaces. | 2008-04 |
|
| Imbalance between ROS production and elimination results in apoptosis induction in primary smooth chorion trophoblast cells prepared from human fetal membrane tissues. | 2008-03-12 |
|
| Assembly of CdS quantum dots onto mesoscopic TiO(2) films for quantum dot-sensitized solar cell applications. | 2008-01-30 |
|
| Sensitive determination of iron(III) by gold electrode modified with 2-mercaptosuccinic acid self-assembled monolayer. | 2007-10-10 |
|
| Paraquat-induced oxidative stress and dysfunction of cellular redox systems including antioxidative defense enzymes glutathione peroxidase and thioredoxin reductase. | 2007-04 |
|
| Fluorescence and interactions with thiol compounds of Nile Red-adsorbed gold nanoparticles. | 2007-03-15 |
|
| Adsorption of carboxylate-modified gold nanoparticles on an octadecylamine monolayer at the air/liquid interface. | 2007-03-13 |
|
| Luminescence and stability of aqueous thioalkyl acid capped CdSe/ZnS quantum dots correlated to ligand ionization. | 2007-03-12 |
|
| Fluorescence intensity and intermittency as tools for following dopamine bioconjugate processing in living cells. | 2007 |
|
| Critical role of exposure time to endogenous oxidative stress in hepatocyte apoptosis. | 2007 |
|
| Selective gold-nanoparticle-based "turn-on" fluorescent sensors for detection of mercury(II) in aqueous solution. | 2006-12-15 |
|
| Highly ordered superlattices from polydisperse Ag nanoparticles: a comparative study of fractionation and self-correction. | 2006-12-07 |
|
| Determination of the size of water-soluble nanoparticles and quantum dots by field-flow fractionation. | 2006-08 |
|
| Kinetic stabilization of growing gold clusters by passivation with thiolates. | 2006-06-29 |
|
| Monolayer behavior and Langmuir-Blodgett manipulation of CdS quantum dots. | 2006-05-18 |
|
| Electrochemical characterization of polyelectrolyte/gold nanoparticle multilayers self-assembled on gold electrodes. | 2005-11-24 |
|
| Electrochemical study of interfacial composite nanostructures: polyelectrolyte/gold nanoparticle multilayers assembled on phospholipid/dextran sulfate monolayers at a liquid-liquid interface. | 2005-11-03 |
|
| Aurothiolates inhibit HIV-1 infectivity by gold(I) ligand exchange with a component of the virion surface. | 1993-02 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:15:06 GMT 2025
by
admin
on
Mon Mar 31 18:15:06 GMT 2025
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| Record UNII |
01IZ7O54VH
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| Record Status |
Validated (UNII)
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| Record Version |
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