티오디글리콜 산

Crystals from water

A white powder or crystals from ethyl acetate/benzene

Colorless crystals

Very soluble in ethanol, soluble in benzene

In water, 4X10+5 mg/l @ 25 deg

400 mg/mL at 25 °C

129 °C

129 °C

Colorless or white solid; [HSDB] Tan powder; [Alfa Aesar MSDS]

Solid

Danger

H314 (92.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 110 reports by companies from 5 notifications to the ECHA C&L Inventory.

Chemical: Acetic acid, 2,2'-thiobis-

REACH registered substance: Thiodi(acetic acid) (EC: 204-663-9)

2,2'-Thiodiacetic acid: Does not have an individual approval but may be used under an appropriate group standard

Emergency treatment: Thioglycolates; The highly alkaline thioglycolates cause both irritant and allergic contact dermatitis in hairdressers; [HSDB] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [Alfa Aesar MSDS] See Thioglycolic acid.

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.

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).

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).

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).

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).

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).

/LABORATORY ANIMALS: Acute Exposure/ Thiodiglycolic acid (50 mg/kg) administered to rats inhibited the carnitine-dependent oxidation of [1-14C]palmitic acid by 55%, but affected neither the oxidation of [1-14C]octanoic acid, which is carnitine-independent, nor the oxidation of [1, 4-14C]succinic acid, a marker of Kreb's cycle activity. Additionally, thiodiglycolic acid (30 microM) inhibited oxidation of palmitic acid but not palmitoyl-L-carnitine in isolated rat liver mitochondria, indicating that it either sequesters carnitine or inhibits carnitine palmitoyltransferase I. This study elucidates a specific mitochondrial dysfunction induced by thiodiglycolic acid which may contribute to the adverse effects associated with ifosfamide chemotherapy.

/ALTERNATIVE IN VITRO TESTS/ Our previous studies in mice indicated that the exposure to vinyl chloride (VC) produced a state of immunostimulation. The metabolism of VC was an important factor in this phenomenon. Two known metabolites of VC, namely thiodiglycolic acid and N-acetyl-S-(hydroxyethyl)-cysteine produced little or no effect when added to mouse splenic lymphocyte cultures in vitro but in vivo administration of thiodiglycolic acid produced apparent immune stimulation in mice.

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).

Thiodiglycolic acid's production and use as detection agent for copper, lead, mercury, and silver may result in its release to the environment through various waste streams. In soil experiments, thiodiglycolic acid was shown to be a biodegradation product of thiodiglycol which is a hydrolysis product of bis(2-chloroethyl) sulfide (mustard gas). If released to air, an estimated vapor pressure of 5.5X10-5 mm Hg at 25 °C indicates thiodiglycolic acid will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase thiodiglycolic acid will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 28 hrs. Particulate-phase thiodiglycolic acid will be removed from the atmosphere by wet and dry deposition. Thiodiglycolic acid is stable to photolysis. If released to soil, thiodiglycolic acid is expected to have very high mobility based upon an estimated Koc of 12. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 4.4X10-14 atm-cu m/mole. The estimated pKa of thiodiglycolic acid is 3.4, 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. If released into water, thiodiglycolic acid is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process as indicated by 100% recovery of test compound following testing at various pH values for 96 hrs. 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 (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.

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.

Used for detection of copper, lead, mercury, and silver; A major metabolite of vinyl chloride monomer and ifosfamide (anti-cancer drug) in human urine; [HSDB]

Detection of copper, lead, mercury, silver.

Analytical reagent

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.