thiodiglycolic acid
acetic acid, 2,2'-thiobis-
Identification
| Name | thiodiglycolic acid |
| IUPAC | 2-(carboxymethylsulfanyl)acetic acid |
| CAS Number | 123-93-3 |
| EINECS | 204-663-9 |
| FDA UNII | 483M3RG5GW |
| Molecular Formula | C4 H6 O4 S |
| Molecular Weight | 150.15362000 |
| MDL Number | MFCD00004359 |
| Nikkaji Number | J5.546H |
| Beilstein | 1764392 |
Regulatory
Physical Properties
| Appearance | white powder (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 129.00 °C. @ 760.00 mm Hg |
| Boiling Point | 377.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 359.00 °F. TCC ( 181.80 °C. ) (est) |
| logP (o/w) | -0.780 (est) |
| Soluble in | water, 4.00E+05 mg/L @ 25 °C (exp) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | antioxidants |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 300 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 thiodiglycolic acid usage levels up to | not for fragrance use. |
| Recommendation for thiodiglycolic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
acetic acid, 2, 2'-thiobis-
acetic acid, 2,2'-thiobis-
acetic acid, thiodi-
bis(
carboxymethyl)sulfide
2-(
carboxymethylsulfanyl)acetic acid
carboxymethylthio)acetic acid
2-(
carboxymethylthio)acetic acid
dicarboxydimethyl sulfide
dicarboxymethyl sulfide
mercaptodiacetic acid
2,2'-
sulfanediyldiacetic acid
2,2'-
thiobis[acetic acid]
2,2'-
thiobisacetic acid
thiodiacetic acid
2,2'-
thiodiacetic acid
2,2'-
thiodiethanoic acid
2,2-
thiodiglycolic acid
2,2'-
thiodiglycolic acid
thiodiglycollic acid
PubMed:
S-carboxymethyl-l-cysteine and it (R/S)-S-oxides in beagle dog plasma and hepatic cytosol.
PubMed:
Eight Zn(II) coordination networks based on flexible 1,4-di(1H-imidazol-1-yl)butane and different dicarboxylates: crystal structures, water clusters, and topologies.
PubMed:
Surface-activated chemical ionization-electrospray mass spectrometry in the analysis of urinary thiodiglycolic acid.
PubMed:
Toxicokinetics of bis(2-chloroethoxy)methane following intravenous administration and dermal application in male and female F344/N rats and B6C3F1 mice.
PubMed:
A comprehensive understanding of thioTEPA metabolism in the mouse using UPLC-ESI-QTOFMS-based metabolomics.
PubMed:
Comparative metabolism of cyclophosphamide and ifosfamide in the mouse using UPLC-ESI-QTOFMS-based metabolomics.
PubMed:
Surface functionalized nano-magnetic particles for wastewater treatment: adsorption and desorption of mercury.
PubMed:
Mouse recombinant phenylalanine monooxygenase and the S-oxygenation of thioether substrates.
PubMed:
Supplemented creatine induces changes in human metabolism of thiocompounds and one- and two-carbon units.
PubMed:
New insights into the biodegradation of thiodiglycol, the hydrolysis product of Yperite (sulfur mustard gas).
PubMed:
Human phenylalanine monooxygenase and thioether metabolism.
PubMed:
[14C]bis(2-chloroethoxy)methane: comparative absorption, distribution, metabolism and excretion in rats and mice.
PubMed:
Ion-pair solid-phase extraction and gas chromatography-mass spectrometric determination of acidic hydrolysis products of chemical warfare agents from aqueous samples.
PubMed:
Diagnostic significance of urinary thiodiglycolic acid as a possible tool for studying the role of vitamins B12 and folates in the metabolism of thiolic substances.
PubMed:
Thiodiglycolic acid and dermatological reactions following S-carboxymethyl-L-cysteine administration.
PubMed:
Nickel(II) complexes with different chromospheres containing macrocyclic ligands: spectroscopic and electrochemical studies.
PubMed:
Electronic, EPR, magnetic and mass spectral studies of mono and homo-binuclear Co(II) and Cu(II) complexes with a novel macrocyclic ligand.
PubMed:
Thiodiglycolic acid as a possible causative agent of fixed drug eruption provoked only after continuous administration of S-carboxymethyl-L-cysteine: case report and review of reported cases.
PubMed:
Spectroscopic, redox and biological activities of transition metal complexes with ons donor macrocyclic ligand derived from semicarbazide and thiodiglycolic acid.
PubMed:
DNA single strand breaks in peripheral lymphocytes associated with urinary thiodiglycolic acid levels in polyvinyl chloride workers.
PubMed:
Synthesis and efficiency of a new chemical fixation agent for stabilizing MSWI fly ash.
PubMed:
Cardiac damage in rodents after exposure to bis(2-chloroethoxy)methane.
PubMed:
Bis(2-chloroethoxy)methane-induced mitochondrial and myofibrillar damage: short-term time-course study.
PubMed:
Diaquabis(1,10-phenanthroline-kappa(2)N,N')manganese(II) thiodiglycolate bis(1,10-phenanthroline-kappa(2)N,N')(thiodiglycolato-kappa(2)O,O')manganese(II) tridecahydrate.
PubMed:
Voltammetric determination of thiodiglycolic acid in urine.
PubMed:
[The bioutilization of thiodiglycol (a breakdown product of mustard gas): isolation of degraders and investigation of degradation conditions].
PubMed:
Urinary thiodiglycolic acid levels for vinyl chloride monomer-exposed polyvinyl chloride workers.
PubMed:
Insights into the mechanisms of ifosfamide encephalopathy: drug metabolites have agonistic effects on alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA)/kainate receptors and induce cellular acidification in mouse cortical neurons.
PubMed:
Biocatalytic transformation of [(2-Hydroxyethyl)thio]acetic acid and thiodiglycolic acid from thiodiglycol by Alcaligenes xylosoxydans ssp. xylosoxydans (SH91).
PubMed:
Diurnal variation in the metabolism of S-carboxymethyl-L-cysteine in humans.
PubMed:
Determination of thiodiglycolic acid in urine by capillary electrophoresis.
PubMed:
Increased urinary losses of carnitine during ifosfamide chemotherapy.
PubMed:
Thiomorpholine and morpholine oxidation by a cytochrome P450 in Mycobacterium aurum MO1. Evidence of the intermediates by in situ 1H NMR.
PubMed:
Thiodiglycolic acid is excreted by humans receiving ifosfamide and inhibits mitochondrial function in rats.
PubMed:
A 13C NMR study of 2-(13)C-chloroacetaldehyde, a metabolite of ifosfamide and cyclophosphamide, in the isolated perfused rabbit heart model. Initial observations on its cardiotoxicity and cardiac metabolism.
PubMed:
Urinary thiodiglycolic acid and thioether excretion in male rats dosed with 1,2-dichloroethane.
PubMed:
Dose-dependent urinary excretion of acrylonitrile metabolites by rats and mice.
PubMed:
Urinary metabolites of [1,2,3-13C]acrylonitrile in rats and mice detected by 13C nuclear magnetic resonance spectroscopy.
PubMed:
Evaluation of proposed sulphoxidation pathways of carbocysteine in man by HPLC quantification.
PubMed:
Identification of thiodiglycolic acid, thiodiglycolic acid sulfoxide, and (3-carboxymethylthio)lactic acid as major human biotransformation products of S-carboxymethyl-L-cysteine.
PubMed:
Ethylene dichloride: the influence of disulfiram or ethanol on oncogenicity, metabolism, and DNA covalent binding in rats.
PubMed:
[Determination of mercapturic acid in urine samples for the monitoring of occupational exposure to xenobiotics].
PubMed:
Urinary excretion of acrylonitrile and its metabolites in rats.
PubMed:
A comparison of technetium-99m-thiodiglycolic acid and iodine-123-hippuran in the evaluation of equivocal upper urinary tract obstruction.
PubMed:
[Study on the excretive regularity of thiodiglycolic acid in the urine of vinyl chloride exposed workers].
PubMed:
Searching for the ideal kidney agent.
PubMed:
Technetium thiodiglycollic acid (99mTc-TDG). A new radiopharmaceutical with the potential for the assessment of renal function.
PubMed:
Comparison of the impact of continuous and intermittent exposure to vinyl chloride, including phenobarbital effect.
PubMed:
Influence of exposure mode on vinyl chloride action.
PubMed:
99Tcm-TDG renography with deconvolution analysis: a comparative study with 99Tcm-DTPA and 123I-hippuran.
PubMed:
Sensitive flame-photometric-detector analysis of thiodiglycolic acid in urine as a biological monitor of vinyl chloride.
PubMed:
[Investigations on the correlation between vinyl chloride (VCM)-uptake and excretion of its metabolites by 15 VCM-exposed workers. II. Measurements of the urinary excretion of the vcm-metabolite thiodiglycolic acid ].
PubMed:
Metabolism of bis(2-chloroethyl)ether and bis(2-chloroisopropyl)ether in the rat.
PubMed:
Chromatographic determination of thiodiglycolic acid - a metabolite of vinyl chloride.
PubMed:
Immunotoxicologic studies with vinyl chloride in rabbits and mice.
PubMed:
Identification of S-(carboxymethyl)-L-cysteine and thiodiglycolic acid, urinary metabolites of 2,2'-bis-(chloroethyl)-ether in the rat.
PubMed:
Molecular mechanism of 1,1-dichloroethylene toxicity: excreted metabolites reveal different pathways of reactive intermediates.
PubMed:
An analytical method, using GC-MS, for the quantitative determination of urinary thiodiglycolic acid.
PubMed:
Thiodiglycolic acid: a major metabolite of bis(2-chloroethyl)ether.
PubMed:
Determination of thiodiglycolic acid in urine specimens of vinyl chloride exposed workers.
PubMed:
Double resonance studies of anions formed in irradiated succinic and thiodiglycolic acid.