Thioglycolic Acid

HCID 1133CAS 68-11-1

Grundinformationen

Standard-SMILES
O=C(O)CS
InChIKey
CWERGRDVMFNCDR-UHFFFAOYSA-N
Summenformel
C2H4O2S
Durchschnittliche Molmasse
92,12 g/mol
Monoisotopische Masse
91,99320037

Überblick

Thioglycolic acid appears as a colorless liquid with an unpleasant odor. Density 1.325 g / cm3. Used to make permanent wave solutions and depilatories. Corrosive to metals and tissue.

Namen und Bezeichner

Bevorzugter Name
Thioglycolic Acid
IUPAC
2-sulfanylacetic acid

Namen und Synonyme

mercaptoacetic acidthioglycolic acid68-11-12-Mercaptoacetic acid2-Thioglycolic acidThioglycollic acidAcetic acid, mercapto-Sulfanylacetic acidThiovanic acidMercaptoessigsaeureGlycolic acid, thio-USAF CB-35
Weitere Namen anzeigen
Acide thioglycoliqueGlycolic acid, 2-thio-Mercaptoethanoic acidKyselina thioglykolovaKyselina merkaptooctovaalpha-Mercaptoacetic acidDTXSID8026141NSC-1894

Datenbank-Bezeichner

CAS
68-11-1
PubChem CID
1133
DTXSID
DTXSID8026141
ChEMBL
CHEMBL116455
ChEBI
CHEBI:30065
UNII
7857H94KHM
EC Number
200-677-4
Nikkaji
J4.856I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,1
Polarare Oberfläche (TPSA)
38,3 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
1
Schwere Atome
5

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Sulfur Compounds

Corrosives

Cosmetics · 2 Einträge

Cosmetic ingredients (Thioglycolic Acid) -> CIR (Cosmetic Ingredient Review)

Hair waving or straightening; Reducing; Depilatory

SpringerMaterials PropertiesBoiling point
LogP · 3 Einträge

log Kow = 0.09

0.05

0.09

Odor · 4 Einträge

Strong, unpleasant odor

ODOR HAS CHARACTERISTIC OF SULFHYDRYL GROUPS

Strong, disagreeable odor characteristic of mercaptans [Note: Olfactory fatigue may occur after short exposures].

Pungent /Anhydrous/

Density · 6 Einträge

1.3253 at 68 °F (NTP, 1992) - Denser than water; will sink

1.3253 g/cu cm at 20 °C

Relative density (water = 1): 1.3

1.33

1.325 @25 °C

1.32

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P361+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301 (96.5%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P333+P317, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Acetic acid, mercapto-

Acetic acid, 2-mercapto- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetic acid, 2-mercapto- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 09-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2175

Thioglycolic acid: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Acetic acid, mercapto-: Human health tier II assessment
DOT LabelCorrosive
Fire Hazards · 3 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health Hazards · 2 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Hazards Summary · 1 Eintrag

Toxicological properties are similar to those of acetic acid. May cause skin irritation in professional hairdressers; Ammonium thioglycolate causes allergic contact dermatitis. Thioglycolic acid and its salts and esters can be irritating to the skin and eyes and repeated exposure can cause skin sensitization. [ACGIH] Corrosive to skin; [Quick CPC] A corrosive substance that can cause pulmonary edema; [ICSC] Danger of skin sensitization; [MAK]

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 Einträge

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Safe StorageSeparated from strong oxidants, strong bases, food and feedstuffs and combustible substances. Keep in a well-ventilated room.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

Toxikologische Informationen

Interactions · 1 Eintrag

Quantum dots (QDs) are a novel class of inorganic fluorophores which are gaining widespread recognition as a result of their exceptional photophysical properties and their applications as a biomarker and in molecular biomedical imaging. The aim of this study was to evaluate the in vivo genotoxicity in mice exposed to CdSe quantum dots of average size 5.0 +/- 0.2 nm and CdSe doped with 1% cobalt ions of similar size. The quantum dots are surface modified using mercaptoacetic acid (MAA) in order to be biocompatible and water-soluble. The MAA-QDs were given to the mice orally at doses of 500, 1000, and 2000 mg/kg by weight of MAA-QDs. Bone marrow and liver samples were collected after two and seven days of treatment. The results indicated that after two days of treatment, the high dose of doped MAA-QDs was significantly able to induce DNA damage, formation of micronuclei (MNs), and generation of DNA adduct (8-hydroxy-2-deoxyguanosine, 8-OHdG). However, increasing DNA damage and the frequency of MNs formation as well as the generation of DNA adducts were observed with both the undoped MAA-QDs (2000 mg/kg) and doped MAA-QDs (1000 and 2000 mg/kg) after seven days of treatment. The results of /this/ study indicate that exposure to high doses of pure MAA-QDs or MAA-QDs doped with cobalt has the potential to cause indirect in vivo genetic damage, which may be attributed to free radical-induced oxidative stress in mice. /CdSe quantum dots surface modified with mercaptoacetic acid/

Target OrgansEyes, skin, respiratory system
Ecotoxicity ValuesLC50; Species: Pimephales promelas (Fathead Minnow); Conditions: freshwater, static, 17 °C, pH 7.0-7.3, alkalinity 50-70 mg/L CaCO3, dissolved oxygen 7-8 mg/L; Concentration: 30000 ug/L for 96 hr /formulated product/
Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.4(SRC), determined from a structure estimation method(2), indicates that mercaptoacetic acid is expected to have very high mobility in soil(SRC). The pKa of mercaptoacetic acid is 3.55(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Mercaptoacetic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.68X10-2 mm Hg at 25 °C(5). Utilizing the Japanese MITI test, 100% of the Theoretical BOD was reached in 4 weeks(6) indicating that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.4(SRC), determined from a structure estimation method(2), indicates that mercaptoacetic acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 3.55(3) indicates mercaptoacetic acid will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water and moist soil surfaces and bioconcentration are not expected to be an important environmental fate processes(SRC). Utilizing the Japanese MITI test, 100% of the Theoretical BOD was reached in 4 weeks(4) indicating that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), mercaptoacetic acid, which has a vapor pressure of 8.68X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase mercaptoacetic 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 10 hrs(SRC), calculated from its rate constant of 3.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Mercaptoacetic acid does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure Routes · 2 Einträge

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

Small quantities of Thioglycolic Acid, as cysteine-thioglycolic acid mixed disulfide, have been identified in human urine via high-voltage paper electrophoresis.

The metabolism and excretion of [(35)S]Thioglycolic Acid was evaluated in male Holtzman rats (weight 200-250 g) and in adult male New Zealand rabbits (weights not stated). The test substance (100 mg/kg) was administered to 12 rats via i.v. injection and to 10 rats via intraperitoneal (i.p.) injection. Also, 2 rats were each given 75 mg/kg via i.p. injection. Animals injected i.v. (12 rats) comprised 1 group, and those injected i.p. (12 rats) comprised the other. Urine samples were collected 24 hours after injection, after which the administered (35)S was excreted, and excretion percentages were determined. The mean urine sulfate content for i.v. dosed rats was 82.3% + 1.6% and for i.p. dosed rats was 90.6% + 1.8%. Most of the radioactivity was excreted in the form of neutral sulfate. Two rabbits were injected i.p. with 100 mg/kg of the test substance, and 1 rabbit was injected i.p. with 200 mg/kg. Urine samples were collected 24 hours after injection. The mean urine sulfur content of the 3 rabbits was 88% of the administered dose. As was true for rats, most of the radioactivity was excreted in the form of neutral sulfate. Additionally, Thioglycolic Acid (100-150 mg/kg, no radioactivity) was administered to a group of 7 rabbits via i.p. injection. Significant concentrations of dithioglycolate (average concentration 28%) were detected in the urine at 24 hr after injection. Only negligible concentrations of Thioglycolate were detected.

Absorption, Distribution and Excretion · 3 Einträge

radioactivity was greatest in the small intestine and kidneys of a rat that was injected i.v. with 50 mg/kg of [(35)S]Thioglycolic Acid. Residual 35S blood concentrations at 0.5 to 7 hours after injection did not exceed 5.3% in rats dosed with 100 mg/kg of [(35)S]Thioglycolic Acid. Most of the radioactivity was excreted in the urine in the form of neutral sulfate 24 hours after 100 mg/kg of [(35)S]Thioglycolic Acid was administered to groups of rats via i.v. and i.p. injection. Similar results were noted after rabbits received 100 and 200 mg/kg doses of [(35)S]Thioglycolic Acid. Significant concentrations of dithioglycolate were detected in the urine of rabbits 24 hours after Thioglycolic Acid (100-150 mg/kg) was injected i.p.

A 30% to 40% dilution of a 25.0% solution (330 mg/kg) of [(35)S]Thioglycolic Acid applied to dorsal skin of rabbits was excreted within 5 hours.

The distribution of radioactivity in Holtzman rats (weights 200-250 g) and in an adult New Zealand rabbit (weight not stated) after i.v. injection of [(35)S]Thioglycolic Acid were investigated. One rat was injected i.v. with 50 mg/kg of the test substance and killed 1 hour later. Radioactivity was greatest in the small intestine and kidneys, less in the liver and stomach, and least in the brain, heart, lungs, spleen, testes, muscle, skin, and bone. The greatest content of 35S, 0.66% of the total administered, was detected in the feces. The authors suggested that this observation may have been due to contamination of the feces with urine missed during the rinsing of urine residue from the cage after collection. The distribution of (35)S in whole blood was evaluated in 6 rats injected i.v. with 100 mg/kg of the test substance and bled during periods of up to 7 hours. Residual (35)S blood concentrations during 0.5 to 7 hours after injection did not exceed 5.3% in any of the 6 animals. The distribution of [(35)S]Thioglycolic Acid in the blood was further investigated in the New Zealand rabbit, with emphasis on binding to the following serum protein fractions: a1-, a2-, b-, and g-globulins and albumin. The test substance (70 mg/kg) was injected i.v. Most of the radioactivity was bound to albumin. The extent of this uptake amounted to 0.14% at 20 minutes after injection and had diminished to 0.016% at 3 hours. The small amount of radioactivity detected in albumin might have been due to isotopic exchange.

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: Thioglycolic Acid

Used to manufacture drugs, permanent wave solutions, and other chemicals; Concentrations are up to 11% in hair products and 5% in depilatories; [ACGIH]

Dressing Hair [Category: Other]

Carbonyl condensation catalyst

Used as a raw material in the manufacture of fine and specialty chemicals in the pharmaceutical and agricultural sectors.

Sensitive reagent for iron, molybdenum, silver, tin ... Used in the manufacture of thioglycolates.

Impurities · 1 Eintrag

Cosmetic grade Thioglycolic Acid consists of Thioglycolic Acid (78% minimum), iron (0.02 ppm maximum), and monochloroacetic acid (0.05% maximum). The following are listed in the CTFA Specification for Thioglycolic Acid: dithiodiglycolic acid (2.0% maximum), sulfated ash (0.05% maximum), arsenic (3 ppm maximum), copper (1 ppm maximum), and lead (20 ppm maximum). /Other sources/ reported that Thioglycolic Acid was pure at 99%. Water content was <0.3% and dithiodiglycolic acid, thioglycolides, and monochloroacetic acid were reported as <0.4%, <0.3%, and <100 ppm, respectively.

U.S. Production · 6 Einträge

2023: 2,500,000 - <4,000,000 lb

(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Acetic acid, mercapto- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#4151]

For more U.S. Production (Complete) data for MERCAPTOACETIC ACID (6 total), please visit the HSDB record page.

Consumer UsesCorrosion inhibitor
Industry UsesAnti-scaling agent
Methods of Manufacturing · 3 Einträge

Industrially, mercaptoacetic acid is produced from chloroacetic acid or its salts and sodium or potassium hydrogen sulfide. Thiodiglycolic acid, dithiodiglycolic acid, and glycolic acid may be formed as side products. The mercaptoacetic acid is isolated from the acidified reaction mixture by extraction with organic solvents (ethers, alcohols, or chlorinated hydrocarbons) and purified by distillation. Both batch and continuous processes have been described in the patent literature as well as processes that operate under a partial pressure of hydrogen sulfide or carbon dioxide.

Prepd by the action of sodium sulfhydrate on sodium chloroacetate; by electrolysis of dithioglycollic acid (from sodium sulfide and sodium chloroacetate).

According to the Cosmetic, Toiletry, and Fragrance Association (CTFA), Thioglycolic Acid may be prepared via the reaction of sodium or potassium chloracetate with alkali metal hydrosulfide in aqueous medium. The reaction mixture is acidified and purified by organic extraction and vacuum distillation.

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