thiosalicylic acid
benzoic acid, 2-mercapto-
Identification
| Name | thiosalicylic acid |
| IUPAC | 2-sulfanylbenzoic acid |
| CAS Number | 147-93-3 |
| EINECS | 205-704-3 |
| FDA UNII | CIP6LXN5XW |
| Molecular Formula | C7 H6 O2 S |
| Molecular Weight | 154.18822000 |
| MDL Number | MFCD00004836 |
| Nikkaji Number | J5.842D |
| Beilstein | 0508507 |
| XlogP3 | 2.40 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 168.50 °C. @ 760.00 mm Hg |
| Boiling Point | 298.60 °C. @ 760.00 mm Hg (est) |
| Flash Point | 274.00 °F. TCC ( 134.40 °C. ) (est) |
| logP (o/w) | 2.390 |
| Soluble in | water, 661.5 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | antioxidants |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 50 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | antioxidants |
| Recommendation for thiosalicylic acid usage levels up to | not for fragrance use. |
| Recommendation for thiosalicylic acid flavor usage levels up to | not for flavor use. |
American International Chemical, Inc.
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Potential Uses
Natural Occurrence
Synonyms
o-
benzoic acid thiol
benzoic acid, 2-mercapto-
benzoic acid, o-mercapto-
mercaptobenzoic acid
2-
mercaptobenzoic acid
4-
mercaptobenzoic acid
o-
mercaptobenzoic acid
salicylic acid, 2-thio-
2-
sulfanylbenzoic acid
o-
sulfhydrylbenzoic acid
2-
thiobenzoic acid
thiophenol-2-carboxylic acid
2-
thiosalicylic acid
o-
thiosalicylic acid
thiosalicylicacid
PubMed:
Ruthenium-catalyzed C-H activation of thioxanthones.
PubMed:
Ethylmercury and Hg(2+) induce the formation of neutrophil extracellular traps (NETs) by human neutrophil granulocytes.
PubMed:
PEG-farnesyl thiosalicylic acid telodendrimer micelles as an improved formulation for targeted delivery of paclitaxel.
PubMed:
In vitro study of thimerosal reactions in human whole blood and plasma surrogate samples.
PubMed:
[Chemical adsorption of thiosalicylic acid on silver surface investigated by surface-enhanced Raman scattering].
PubMed:
Influence of quantum dots on the aromaticity of thiosalicylic acid.
PubMed:
Simvastatin induces a central hypotensive effect via Ras-mediated signalling to cause eNOS up-regulation.
PubMed:
Supramolecular self-assembly of 1D and 3D heterometallic coordination polymers with triruthenium building blocks.
PubMed:
Intrathecal delivery of farnesyl thiosalicylic acid and GW 5074 attenuates hyperalgesia and allodynia in chronic constriction injury-induced neuropathic pain in rats.
PubMed:
Analgesic potential of intrathecal farnesyl thiosalicylic acid and GW 5074 in vincristine-induced neuropathic pain in rats.
PubMed:
Novel palladium(II) complexes containing a sulfur ligand: structure and biological activity on HeLa cells.
PubMed:
New 2-thioether-substituted apomorphines as potent and selective dopamine Dâ receptor agonists.
PubMed:
Iron-ligand coordination in tandem radical cyclizations: synthesis of benzo[b]thiophenes by a one-pot reaction of iron 1,3-diketone complexes with 2-thiosalicylic acids.
PubMed:
Synthesis and characterization of Au102(p-MBA)44 nanoparticles.
PubMed:
Enhanced stereoselectivity of a Cu(II) complex chiral auxiliary in the synthesis of Fmoc-L-γ-carboxyglutamic acid.
PubMed:
Luteolin and thiosalicylate inhibit HgCl(2) and thimerosal-induced VEGF release from human mast cells.
PubMed:
Ultraviolet treatment and biodegradation of dibenzothiophene: Identification and toxicity of products.
PubMed:
Low molecular weight thiols reduce thimerosal neurotoxicity in vitro: modulation by proteins.
PubMed:
Sensitization effect of thimerosal is mediated in vitro via reactive oxygen species and calcium signaling.
PubMed:
Responsiveness of human monocyte-derived dendritic cells to thimerosal and mercury derivatives.
PubMed:
Synthesis and characterization of thiosalicylic acid stabilized gold nanoparticles.
PubMed:
Phase 1 first-in-human clinical study of S-trans,trans-farnesylthiosalicylic acid (salirasib) in patients with solid tumors.
PubMed:
Expression of metallothionein mRNAs on mouse cerebellum microglia cells by thimerosal and its metabolites.
PubMed:
Salirasib (farnesyl thiosalicylic acid) for brain tumor treatment: a convection-enhanced drug delivery study in rats.
PubMed:
Zinc ions cause the thimerosal-induced signal of fluorescent calcium probes in lymphocytes.
PubMed:
Preconcentration of lead with Amberlite XAD-2 and Amberlite XAD-7 based chelating resins for its determination by flame atomic absorption spectrometry.
PubMed:
Thimerosal and the relevance of patch-test reactions in children.
PubMed:
In vitro-refolding of a single-chain Fv fragment in the presence of heteroaromatic thiols.
PubMed:
Inhibitors of chronically active ras: potential for treatment of human malignancies.
PubMed:
Activation of TRPA1 by farnesyl thiosalicylic acid.
PubMed:
Evaluation of cytotoxicity attributed to thimerosal on murine and human kidney cells.
PubMed:
Cleavage of focal adhesion kinase is an early marker and modulator of oxidative stress-induced apoptosis.
PubMed:
Competing ligand exchange-solid phase extraction method for the determination of the complexation of dissolved inorganic mercury (II) in natural waters.
PubMed:
Effect of subinhibitory concentration of some established and experimental antifungal compounds on the germ tube formation in Candida albicans.
PubMed:
Field amplified sample injection-capillary electrophoresis-tandem mass spectrometry for the analysis of acrylamide in foodstuffs.
PubMed:
A Ras inhibitor tilts the balance between Rac and Rho and blocks phosphatidylinositol 3-kinase-dependent glioblastoma cell migration.
PubMed:
Quantitative description of the deactivation channels of the first excited singlet state of 2- and 4-thiosalicylic acids.
PubMed:
Using inhibitors of prenylation to block localization and transforming activity.
PubMed:
Thimerosal induces apoptosis and G2/M phase arrest in human leukemia cells.
PubMed:
Ras antagonist inhibits growth and chemosensitizes human epithelial ovarian cancer cells.
PubMed:
E2F1 identified by promoter and biochemical analysis as a central target of glioblastoma cell-cycle arrest in response to Ras inhibition.
PubMed:
Effect of arachidonic acid reacylation on leukotriene biosynthesis in human neutrophils stimulated with granulocyte-macrophage colony-stimulating factor and formyl-methionyl-leucyl-phenylalanine.
PubMed:
Thiosalicylic acid-functionalized silver nanoparticles synthesized in one-phase system.
PubMed:
Determination of mercury complexation in coastal and estuarine waters using competitive ligand exchange method.
PubMed:
Self-assembly of dialkyltin moieties and mercaptobenzoic acid into macrocyclic complexes with hydrophobic "pseudo-cage" or double-cavity structures: supramolecular infrastructures involving intermolecular C-H...S weak hydrogen bonds and pi-pi interactions.
PubMed:
Chelating sorbents based on silica gel and their application in atomic spectrometry.
PubMed:
One-pot synthesis of benzo[e]1,4-oxathiepin-5-ones under solvent-free condition via self-promoted thiolysis of 1,2-epoxides.
PubMed:
Hydrothermal synthesis and magnetic properties of novel Mn(II) and Zn(II) materials with thiolato-carboxylate donor ligand frameworks.
PubMed:
A new positron emission tomography imaging agent for the serotonin transporter: synthesis, pharmacological characterization, and kinetic analysis of [11C]2-[2-(dimethylaminomethyl)phenylthio]-5-fluoromethylphenylamine ([11C]AFM).
PubMed:
Using model complexes to augment and advance metalloproteinase inhibitor design.
PubMed:
Development of a direct-binding chloramphenicol sensor based on thiol or sulfide mediated self-assembled antibody monolayers.
PubMed:
Effect of taxol and okadaic acid on microtubule dynamics in thimerosal-arrested primary mouse oocytes: a confocal study.
PubMed:
Antimycobacterial and antifungal isosters of salicylamides.
PubMed:
The thiol reagent, thimerosal, irreversibly inhibits meiosis reinitiation in mouse oocyte when applied during a very early and narrow temporal window: a pharmacological analysis.
PubMed:
Farnesyl transferase inhibitor SCH66336 is cytostatic, pro-apoptotic and enhances chemosensitivity to cisplatin in melanoma cells.
PubMed:
Farnesyl thiosalicylic acid chemosensitizes human melanoma in vivo.
PubMed:
Superoxide dismutase activity and electrochemical study of the binuclear [Cu(TSA)2py]2 complex.
PubMed:
Biochemical and molecular basis of thimerosal-induced apoptosis in T cells: a major role of mitochondrial pathway.
PubMed:
Functional inhibition of Ras by S-trans,trans-farnesyl thiosalicylic acid attenuates atherosclerosis in apolipoprotein E knockout mice.
PubMed:
Farnesyl thiosalicylic acid inhibits the growth of melanoma cells through a combination of cytostatic and pro-apoptotic effects.
PubMed:
Piroxicam-induced photodermatitis. Cross-reactivity among oxicams. A case report.
PubMed:
Thimerosal in the detection of clinically relevant allergic contact reactions.
PubMed:
Simultaneous determination of reduced and oxidized glutathione in peripheral blood mononuclear cells by liquid chromatography-electrospray mass spectrometry.
PubMed:
Thiosalicylic acid-immobilized Amberlite XAD-2: metal sorption behaviour and applications in estimation of metal ions by flame atomic absorption spectrometry.
PubMed:
Unprecedented stabilization of cobalt(II) in a tetrahedral S2O2 environment: the use of a redox-noninnocent ligand.
PubMed:
A novel Ras antagonist regulates both oncogenic Ras and the tumor suppressor p53 in colon cancer cells.
PubMed:
S-H...S hydrogen-bond chain in thiosalicylic acid
PubMed:
NO-Donors, part 3: nitrooxyacylated thiosalicylates and salicylates - synthesis and biological activities(#).
PubMed:
In situ infrared spectroscopic analysis of the adsorption of aromatic carboxylic acids to TiO2, ZrO2, Al2O3, and Ta2O5 from aqueous solutions.
PubMed:
Targeting of K-Ras 4B by S-trans,trans-farnesyl thiosalicylic acid.
PubMed:
Thimerosal: a versatile sulfhydryl reagent, calcium mobilizer, and cell function-modulating agent.
PubMed:
Mechanisms of drug-induced allergic contact dermatitis.
PubMed:
Thimerosal positivities: patch testing to methylmercury chloride in subjects sensitive to ethylmercury chloride.
PubMed:
Thimerosal positivities: the rôle of SH groups and divalent ions.
PubMed:
Thimerosal positivities: the role of organomercury alkyl compounds.
PubMed:
Stringent structural requirements for anti-Ras activity of S-prenyl analogues.
PubMed:
Improved analytical procedure for the measurement of captopril in human plasma by gas chromatography--mass spectrometry and its application to pharmacokinetic studies.
PubMed:
The effect of thimerosal on neutrophil migration: a comparison with the effect on calcium mobilization and CD11b expression.
PubMed:
Hypersensitivity to thimerosal: the sensitizing moiety.
PubMed:
Effect of thimerosal and other sulfhydryl reagents on calcium permeability in thymus lymphocytes.
PubMed:
Thimerosal induces toxic reaction in non-sensitized animals.
PubMed:
Induction of the alkylation-inducible aidB gene of Escherichia coli by cytoplasmic acidification and N-ethylmaleimide.
PubMed:
Evaluation of the capability of different chromatographic systems for the monitoring of thimerosal and its degradation products by high-performance liquid chromatography with amperometric detection.
PubMed:
Vascular and anti-platelet actions of 1,2- and 1,3-glyceryl dinitrate.
PubMed:
Ethylmercuric chloride: the responsible agent in thimerosal hypersensitivity.
PubMed:
Sulfhydryl group donors potentiate the hypotensive effect of acetylcholine in rats.
PubMed:
Phytogrowth-inhibitory activities of sulfur-containing compounds. II. The inhibitory activities of thiosalicylic acid and dihydro-2(3H)-thiophenone-related compounds on plant growth.
PubMed:
[Cutaneous sensitivity to mercury and its compounds].
PubMed:
HPLC analysis of thimerosal and its degradation products in ophthalmic solutions with electrochemical detection.
PubMed:
Photosensitivity to piroxicam: absence of cross-reaction with tenoxicam.
PubMed:
Thiol adducts of ethacrynic acid increase outflow facility in enucleated calf eyes.
PubMed:
Conversion of nitroglycerin to nitric oxide in microsomes of the bovine coronary artery smooth muscle is not primarily mediated by glutathione-S-transferases.
PubMed:
Biochemical and pharmacological interactions between nitroglycerin and thiols. Effects of thiol structure on nitric oxide generation and tolerance reversal.
PubMed:
Simultaneous analysis of flunixin, naproxen, ethacrynic acid, indomethacin, phenylbutazone, mefenamic acid and thiosalicylic acid in plasma and urine by high-performance liquid chromatography and gas chromatography-mass spectrometry.
PubMed:
Sensitivity to thimerosal and photosensitivity to piroxicam.
PubMed:
Minimum eliciting patch test concentration of thimerosal.
PubMed:
Piroxicam-induced photosensitivity and contact sensitivity to thiosalicylic acid.
PubMed:
Clinical evidence of cross-sensitivity between thiosalicylic acid, a contact allergen, and piroxicam, a photoallergen.
PubMed:
Theoretical studies of the mechanism of the action of the neurohypophyseal hormones. I. Molecular electrostatic potential (MEP) and molecular electrostatic field (MEF) maps of some vasopressin analogues.
PubMed:
Molecular mechanics calculations on deaminooxytocin and on deamino-arginine-vasopressin and its analogues.
PubMed:
Sulfasalazine and 5-aminosalicylic acid inhibit contractile leukotriene formation.
PubMed:
Stimulation of coronary guanylate cyclase by nicorandil (SG-75) as a mechanism of its vasodilating action.
PubMed:
Evidence for thimerosal induced cytoprotection on rat stomach.
PubMed:
Decomposition of thimerosal in aqueous solution and its determination by high-performance liquid chromatography.
PubMed:
Thiopurine methyltransferase. Aromatic thiol substrates and inhibition by benzoic acid derivatives.
PubMed:
The effects of thiosalicylic and hydroxyethylethylenediaminetriacetic acids on the absorption and excretion of 54Mn and 65Zn in the duodenally dosed sheep.
PubMed:
Effect of various compounds on the reaction of tris-(2-chloroethyl)amine with ribonucleic acid in vitro and on its toxicity in mice.
PubMed:
Chelate-forming resins prepared by modification of anion-exchange resins.
PubMed:
New evaluation of potential methylmercury scavengers.
PubMed:
Merthiolate hypersensitivity and vaccination.
PubMed:
[S-Acyl derivatives of thiosalicylamides with antifungal activity. III].
PubMed:
Vanadium(V) as an oxidant for thiol compounds.
PubMed:
Influence of zinc-ligand mixtures on serum zinc levels in rats.
PubMed:
Synthesis, spectral properties, and antibacterial activity of synthetic precursors of macrocyclic oxa- and thia-substituted benzolactones and benzoketones.
PubMed:
Thiol adducts of ethacrynic acid: a correlation of the rate of liberation of ethacrynic acid with the onset and magnitude of the diuretic response.
PubMed:
[STUDIES ON ANTIBILHARZIAL DRUGS. I. SYNTHESIS OF THIOSALICYLIC ACID DERIVATIVES].
PubMed:
[DETERMINATION OF FLUOROSTAN WITH THIOSALICYLIC ACID].
PubMed:
Stimulation of brain respiration by thiosalicylic acid.
PubMed:
Sensitizing component in thiosalicylic acid.
PubMed:
[Synthesis of various derivatives of 2-mercaptobenzoic acid (thiosalicylic acid) from S-beta-D-glucopyranoside. VI. Phenolglycosides].