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 | C4H4O4S |
| Molecular Weight | 148.137 |
| Charge | -2 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H |
| Molecular Weight | 1.0079 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|
| Homology modeling and docking mechanism of the mercaptosuccinate and methotrexate to P. falciparum 1-Cys peroxiredoxin: a preliminary molecular study. | 2002 Aug |
|
| Modulation of somatodendritic dopamine release by endogenous H(2)O(2): susceptibility in substantia nigra but resistance in VTA. | 2002 Feb |
|
| Catalytic determination of Pb(II) in the presence of Cu(II). | 2002 Sep |
|
| Discovery and design of novel inhibitors of botulinus neurotoxin A: targeted 'hinge' peptide libraries. | 2003 Jan-Feb |
|
| Spontaneous DNA fragmentation in swim-up selected human spermatozoa during long term incubation. | 2003 Mar-Apr |
|
| The C2-like beta-barrel domain mediates the Ca2+-dependent resistance of 5-lipoxygenase activity against inhibition by glutathione peroxidase-1. | 2003 Oct 31 |
|
| Mechanistic information on the copper-catalysed autoxidation of mercaptosuccinic acid in aqueous solution. | 2004 Jan 21 |
|
| Effects of antirheumatic gold compounds on the conversion of xanthine dehydrogenase to oxidase in rabbit liver cytosol in vitro. | 2004 Jul 23 |
|
| Endogenous hydrogen peroxide regulates the excitability of midbrain dopamine neurons via ATP-sensitive potassium channels. | 2005 Apr 27 |
|
| Primary hepatocyte apoptosis is unlikely to relate to caspase-3 activity under sustained endogenous oxidative stress. | 2005 Feb |
|
| Size-selective separation of gold nanoparticles using isoelectric focusing electrophoresis (IEF). | 2005 Feb 14 |
|
| Electrochemical study of interfacial composite nanostructures: polyelectrolyte/gold nanoparticle multilayers assembled on phospholipid/dextran sulfate monolayers at a liquid-liquid interface. | 2005 Nov 3 |
|
| Selective gold-nanoparticle-based "turn-on" fluorescent sensors for detection of mercury(II) in aqueous solution. | 2006 Dec 15 |
|
| Highly ordered superlattices from polydisperse Ag nanoparticles: a comparative study of fractionation and self-correction. | 2006 Dec 7 |
|
| Kinetic stabilization of growing gold clusters by passivation with thiolates. | 2006 Jun 29 |
|
| Acute depletion of reduced glutathione causes extensive carbonylation of rat brain proteins. | 2006 Mar |
|
| Monolayer behavior and Langmuir-Blodgett manipulation of CdS quantum dots. | 2006 May 18 |
|
| 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 |
|
| Preparation of gold nanoparticles in an aqueous medium using 2-mercaptosuccinic acid as both reduction and capping agent. | 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 |
|
| catena-Poly[4,4'-bipyridinium [[diaqua-disulfatocadmium(II)]-μ-4,4'-bipyridine-κN:N'] dihydrate]. | 2009 Dec 12 |
|
| Synthesis of coumarin heterocyclic derivatives with antioxidant activity and in vitro cytotoxic activity against tumour cells. | 2009 Jun |
|
| 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 |
Patents
| Substance Class |
Chemical
Created
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admin
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Edited
Fri Dec 15 15:58:32 GMT 2023
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on
Fri Dec 15 15:58:32 GMT 2023
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| Record UNII |
01IZ7O54VH
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| Record Status |
Validated (UNII)
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