Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C4H6O4S |
| Molecular Weight | 150.153 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC(S)C(O)=O
InChI
InChIKey=NJRXVEJTAYWCQJ-UHFFFAOYSA-N
InChI=1S/C4H6O4S/c5-3(6)1-2(9)4(7)8/h2,9H,1H2,(H,5,6)(H,7,8)
| Molecular Formula | C4H6O4S |
| Molecular Weight | 150.153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| 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 |
|---|---|---|
| Aurothiolates inhibit HIV-1 infectivity by gold(I) ligand exchange with a component of the virion surface. | 1993 Feb |
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| Electrochemical characterization of polyelectrolyte/gold nanoparticle multilayers self-assembled on gold electrodes. | 2005 Nov 24 |
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| Electrochemical study of interfacial composite nanostructures: polyelectrolyte/gold nanoparticle multilayers assembled on phospholipid/dextran sulfate monolayers at a liquid-liquid interface. | 2005 Nov 3 |
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| Determination of the size of water-soluble nanoparticles and quantum dots by field-flow fractionation. | 2006 Aug |
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| Selective gold-nanoparticle-based "turn-on" fluorescent sensors for detection of mercury(II) in aqueous solution. | 2006 Dec 15 |
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| Highly ordered superlattices from polydisperse Ag nanoparticles: a comparative study of fractionation and self-correction. | 2006 Dec 7 |
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| Kinetic stabilization of growing gold clusters by passivation with thiolates. | 2006 Jun 29 |
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| Monolayer behavior and Langmuir-Blodgett manipulation of CdS quantum dots. | 2006 May 18 |
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| 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 |
|
| Paraquat-induced oxidative stress and dysfunction of cellular redox systems including antioxidative defense enzymes glutathione peroxidase and thioredoxin reductase. | 2007 Apr |
|
| Luminescence and stability of aqueous thioalkyl acid capped CdSe/ZnS quantum dots correlated to ligand ionization. | 2007 Mar 12 |
|
| Adsorption of carboxylate-modified gold nanoparticles on an octadecylamine monolayer at the air/liquid interface. | 2007 Mar 13 |
|
| Fluorescence and interactions with thiol compounds of Nile Red-adsorbed gold nanoparticles. | 2007 Mar 15 |
|
| Sensitive determination of iron(III) by gold electrode modified with 2-mercaptosuccinic acid self-assembled monolayer. | 2007 Oct 10 |
|
| Preparation of gold nanoparticles in an aqueous medium using 2-mercaptosuccinic acid as both reduction and capping agent. | 2008 Apr |
|
| Antithrombogenic polynitrosated polyester/poly(methyl methacrylate) blend for the coating of blood-contacting surfaces. | 2008 Apr |
|
| catena-Poly[[tetra-aqua-(μ-4,4'-bipyridine-κN:N')zinc(II)] fumarate tetra-hydrate]. | 2008 Apr 16 |
|
| Identification of bismuth-thiolate-carboxylate clusters by electrospray ionization mass spectrometry. | 2008 Apr 7 |
|
| Assembly of CdS quantum dots onto mesoscopic TiO(2) films for quantum dot-sensitized solar cell applications. | 2008 Jan 30 |
|
| Oxidative alterations induced by D-aspartic acid in prepubertal rat testis in vitro: a mechanistic study. | 2008 Jul 1 |
|
| A unique family of stable and water-soluble S-nitrosothiol complexes. | 2008 Jun 2 |
|
| Imbalance between ROS production and elimination results in apoptosis induction in primary smooth chorion trophoblast cells prepared from human fetal membrane tissues. | 2008 Mar 12 |
|
| Synthesis and bio-imaging application of highly luminescent mercaptosuccinic acid-coated CdTe nanocrystals. | 2008 May 21 |
|
| Tanshinone IIA reduces macrophage death induced by hydrogen peroxide by upregulating glutathione peroxidase. | 2008 Oct 10 |
|
| Photoelectrochemical signal chain based on quantum dots on gold--sensitive to superoxide radicals in solution. | 2008 Oct 15 |
|
| Synthesis of CdTe nanocrystals with mercaptosuccinic acid as stabilizer. | 2008 Sep |
|
| 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 Sep |
|
| [Role of glycolysis and antioxidant enzymes in the toxicity of amyloid beta peptide Abeta25-35 to erythrocytes]. | 2008 Sep-Oct |
|
| Oxidative stress in stroke pathophysiology validation of hydrogen peroxide metabolism as a pharmacological target to afford neuroprotection. | 2009 |
|
| Methylmercury neurotoxicity is associated with inhibition of the antioxidant enzyme glutathione peroxidase. | 2009 Aug 15 |
|
| catena-Poly[4,4'-bipyridinium [[diaqua-disulfatocadmium(II)]-μ-4,4'-bipyridine-κN:N'] dihydrate]. | 2009 Dec 12 |
|
| 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 Jan-Feb |
|
| Synthesis of coumarin heterocyclic derivatives with antioxidant activity and in vitro cytotoxic activity against tumour cells. | 2009 Jun |
|
| Imaging pancreatic cancer using bioconjugated InP quantum dots. | 2009 Mar 24 |
|
| Electrochemical quartz crystal microbalance study of covalent tethering of carboxylated thiol to polyaniline for electrocatalyzed oxidation of ascorbic acid in neutral aqueous solution. | 2009 Oct 28 |
|
| H(2)O(2)-mediated modulation of cytosolic signaling and organelle function in rat hippocampus. | 2009 Sep |
|
| Poly[[μ(3)-chlorido-bis(μ(2)-thio-urea-κS)disilver(I)] nitrate]. | 2010 Aug 11 |
|
| Expression of tyrosine hydroxylase increases the resistance of human neuroblastoma cells to oxidative insults. | 2010 Jan |
|
| Antibacterial nitric oxide-releasing polyester for the coating of blood-contacting artificial materials. | 2010 Jul |
|
| An amperometric immunosensor based on a polyelectrolyte/gold magnetic nanoparticle supramolecular assembly--modified electrode for the determination of HIV p24 in serum. | 2010 Jul 23 |
|
| Gold nanoparticle membranes as large-area surface monolayers. | 2010 Jun 1 |
|
| Aqueous synthesis and fluorescence-imaging application of CdTe/ZnSe core/shell quantum dots with high stability and low cytotoxicity. | 2010 Mar |
|
| Regulation of the protein-loading capacity of hydroxyapatite by mercaptosuccinic acid modification. | 2010 Mar |
|
| Ag(9) quantum cluster through a solid-state route. | 2010 Nov 24 |
|
| Cysteine protects freshly isolated cardiomyocytes against oxidative stress by stimulating glutathione peroxidase. | 2010 Oct |
|
| Fluorescent carbon dots capped with PEG200 and mercaptosuccinic acid. | 2010 Sep |
|
| Luminescent quantum clusters of gold in bulk by albumin-induced core etching of nanoparticles: metal ion sensing, metal-enhanced luminescence, and biolabeling. | 2010 Sep 3 |
|
| The gender-dependent difference of liver GSH antioxidant system in mice and its influence on isoline-induced liver injury. | 2011 Feb 4 |
|
| Resveratrol attenuates apoptosis of pulmonary microvascular endothelial cells induced by high shear stress and proinflammatory factors. | 2011 Sep |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 01:39:11 GMT 2023
by
admin
on
Sat Dec 16 01:39:11 GMT 2023
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| Record UNII |
94239W5L4H
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| Record Status |
Validated (UNII)
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200-736-4
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THIOMALIC ACID
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C046062
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94239W5L4H
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100000177360
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m10766
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70-49-5
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6268
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DTXSID20861615
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38705
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7302
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PARENT -> IMPURITY |
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ACTIVE MOIETY |
