Thiodiglycolic acid

150.148

150.15

204-663-9

483M3RG5GW

40469|28743

DTXSID1051432

Crystals from water|A white powder or crystals from ethyl acetate/benzene|Colorless crystals

29309070

99.9

0.1

Solid

1.352 (estimate)

129 °C

241.69°C (rough estimate)

181.8±23.7 °C

1.5500 (estimate)

H2O: 400g/l

-20ºC

1.01E-06mmHg at 25°C

LD50 orally in Rabbit: > 2000 mg/kg

Corrosive

III

8

UN 3261 8/PG 2

3

8

26-36/37/39-45

AJ6475000

C

Stable under normal temperatures and pressures.

P280-P305 + P351 + P338-P310

H314

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Danger|H314 (97.48%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 119 companies from 4 notifications to the ECHA C&L Inventory.

Combustible

LD50 Mouse ip 300 mg/kg

Thiodiglycolic acid's production and use as a detection agent of copper, lead, mercury, and silver(1) may result in its release to the environment through various waste streams(SRC). In soil, thiodiglycolic acid was shown to be a biodegradation product of thiodiglycol, a hydrolysis product of bis(2-chloroethyl) sulfide (mustard gas)(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a structure estimation method(2), indicates that thiodiglycolic acid is expected to have very high mobility in soil(SRC). Volatilization of thiodiglycolic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.4X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Thiodiglycolic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.5X10-5 mm Hg(SRC), determined from a fragment constant method(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a structure estimation method(2), indicates that thiodiglycolic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.4X10-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The estimated pKa of thiodiglycolic acid is 3.4(5), indicating that this compound will partially exist in the dissociated form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(6). According to a classification scheme(7), an estimated BCF of 3(SRC), from an estimated log Kow of -1.2(SRC) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Thiodiglycolic acid is stable to hydrolysis(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiodiglycolic acid, which has an estimated vapor pressure of 5.5X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase thiodiglycolic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 28 hrs(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase thiodiglycolic acid may be removed from the air by wet and dry deposition(SRC). Thiodiglycolic acid is stable to photolysis(4).

The rate constant for the vapor-phase reaction of thiodiglycolic acid with photochemically-produced hydroxyl radicals has been estimated as 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 28 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Thiodiglycolic acid is not expected to undergo hydrolysis in the environment(2); concentrations of 20 and 50 mg/l were tested at pHs of 4, 7, and 11 and resulted in 100% recovery of the thiodiglycolic acid after 48 and 96 hours(2). Also, thiodiglycolic acid does not directly photolyze(2). Initial concentrations of 50 and 20 mg/l thiodiglycolic acid were sunlight irradiated for 14 days with final concentrations reported at 49.4 and 19.5 mg/l, respectively; results for the dark controls were 49.2 and 19.8 mg/l, respectively(2).

An estimated BCF of 3 was calculated for thiodiglycolic acid(SRC), using an estimated log Kow of -1.2(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for thiodiglycolic acid can be estimated to be 12(SRC). According to a classification scheme(2), this estimated Koc value suggests that thiodiglycolic acid is expected to have very high mobility in soil. However, adsorption of thiodiglycolic acid was found to vary with soil type; observed maximum sorption capacities ranged from 19.9 mg/kg (53% sand, 14% silt, 33% clay, pH 8.5, 0.5% OM) to 427.4 mg/kg (43% sand, 21% silt, 36% clay, pH 4.7, 0.4% OM)(3). The estimated pKa of thiodiglycolic acid is 3.4(4), indicating that this compound will partially exist in the dissociated form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(5).

The Henry's Law constant for thiodiglycolic acid is estimated as 4.4X10-14 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that thiodiglycolic acid is expected to be essentially nonvolatile from water surfaces(2). Thiodiglycolic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.5X10-5 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to thiodiglycolic acid may occur through inhalation and dermal contact with this compound at workplaces where thiodiglycolic acid is produced or used. (SRC)

Thiodiglycolic acid is excreted in urine.|The dose dependence of the urinary excretion of acrylonitrile (ACN) metabolites was studied after oral admin of [2,3-14C]ACN to male F-344 rats (0.09-28.8 mg/kg) and male B6C3F1 mice (0.09-10.0 mg/kg). Urine was the major route of excretion of ACN metabolites (77-104% of the dose), with <8% of the dose excreted in the feces. Five major components accounted for 75-100% of the total urinary radioactivity. Thiodiglycolic acid was derived from the epoxide metabolite of ACN.|1,2-Dichloroethane (DCE) is extensively metabolized and partially excreted in urine as thioether cmpds, which include thiodiglycolic acid (TDGA). In this study, we have compared the urinary excretion of TDGA and thioethers in the rat after admin of increasing doses of DCE. Male Sprague Dawley rats were given a single oral dose of labelled [14C]DCE (0.125-8.08 mmol/kg bw) and 24-hr urine samples were collected. The percentage of the administered radioactivity that was excreted in urine decreased with increasing dose of DCE and ranged between 63 and 7.4%. The amount of TDGA increased proportionally to the DCE dose up to 1.01 mmol DCE/kg bw and corresponded to 0.22 mmol TDGA/mmol DCE. Up to 0.25 mmol DCE/kg bw, the amount of thioethers recovered in urine was not significantly different as compared to the vehicle control group (11.8 +/- 0.6 mumol SH equiv./kg bw, n=10). From the 0.25-4.04 mmol DCE/kg bw dose, the amount of thioethers increased linearly with the dose of DCE and corresponded to 0.028 mmol SH equiv./mmol DCE. The ratio between urinary thioethers and TDGA increased with the DCE dose and reached 0.17 +/- 0.01 (n=5) at a dose of 8.08 mmol DCE/kg bw.

Thiodiglycolic acid (TdGA) is the major metabolite of vinyl chloride monomer (VCM) detected in human urine. Although urinary TdGA has been reported to be associated with ambient VCM exposure, the relationship between urinary TdGA and a low level of air VCM is not clear. Questionnaires were administered to 16 polyvinyl chloride manufacturing workers to obtain a detailed history of occupation and lifestyle. For each worker, personal air monitoring for VCM was performed and a time-weighted average for VCM exposure was calculated. The urinary TdGA levels at the end of a work shift, and at the commencement of the next shift, were also assessed for each worker. Urine analysis revealed that TdGA levels at the beginning of the next shift were higher than those at the end of that shift. Workers experiencing a VCM exposure >5 ppm in air revealed a urinary TdGA level significantly greater than those experiencing a VCM exposure of <5 ppm (P<0.05). The best fit of regression for urinary TdGA on air VCM was Y=1.06 + 0.57X for urine collected at the commencement of the following work shift, where X is the air VCM concn and Y is the urinary TdGA concn (r2=0.65, P<0.01). We conclude that the urinary TdGA level is best detected at the commencement of the next shift and that it can be used as an exposure marker for polyvinyl chloride workers when the air VCM level to which they are exposed is >5 ppm.|Strong correlation was found between vinyl chloride concentration at working places & the increased excretion of thiodiglycolic acid in 18 exposed workers.|Evaluation of occupational exposure to poly(vinyl chloride) in air, collected in resp area, were most reliable indexes of individual exposure. No correlation was found between urinary concentration of thiodiglycolic acid & poly(vinyl chloride) concentration in air inhaled.|Thiodiglycolic acid was identified by GC-MS measurements in urine of rats after ip injections of 2,2'-bis-(chloroethyl)-ether.|For more Metabolism/Metabolites (Complete) data for THIODIGLYCOLIC ACID (16 total), please visit the HSDB record page.

thiodiacetic acid

Acetic acid, 2,2'-thiobis-: ACTIVE|Thioglycolic acid is manufactured by the reaction of monochloracetic acid or its salts with alkali hydrosulfides ... in aqueous medium, under controlled conditons of pressure, temperature, pH, concentration, to give a higher yield of thioglycolate salt and minimize the formation of such by-products as thiodiglycolic and dithiodiglycolic acids. The reaction mixture is acidified to liberate thioglycolic acid, which is extracted from the aqueous solution into an organic solvent, such as an ether, and then purified by vacuum distillation.

The detection of thiodiglycolic acid in urine by gas chromatography is described. Procedure includes addition of internal STD (o-phthalic acid), ethyl acetate extraction, evaporation of solvent and silylation of TdGA with n-trimethylsilyl-diethylamine in pyridine (1:1).|Metabolites of vinyl chloride have been identified in the urine of rats and humans using GC-MS. As there is strong correlation between vinyl chloride exposure in humans and increased excretion of thiodiglycolic acid, this metabolite has been used for monitoring purposes.

Cosmetics -> Reducing