<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-19 04:17:25 UTC</creation_date>
  <update_date>2026-05-14 19:51:10 UTC</update_date>
  <accession/>
  <common_name>Mercaptoacetic acid</common_name>
  <class>SmallMolecule</class>
  <description>Mercaptoacetic acid is an organic compound with the formula C2H4O2S and an average molecular weight of 92.12 g/mol. Mercaptoacetic acid belongs to the carboxylic acids, a subclass of carboxylic acids and derivatives within the organic compounds.

In industrial applications, this compound serves as an antioxidant and a reducing agent. It is also utilized as a depilatory and for the purposes of hair straightening or waving.

The compound is identified in 29 recorded sources across various sectors. Within the category of electrical and electronic equipment, it is found in antennas, communication cables or conductors, contacts, cores yokes or armatures, and conductors or conductive bodies characterised by the conductive materials, among 12 other sources. In household cleaning and consumer products, it is present in soap detergents, bleaching agents, perfumes within detergents and soaps, pipe accessories, and cigar cigarettes, as well as two additional sources. Furthermore, it is associated with food, food processing and cookware, specifically in the processing of meats and fish, the preparation of vinegar, food preservation, and fermentation processes for beer.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>2-sulfanylacetic acid</synonym>
    <synonym>Acetic acid, mercapto-</synonym>
    <synonym>Thioglycolic acid</synonym>
  </synonyms>
  <chemical_formula>C2H4O2S</chemical_formula>
  <average_molecular_weight>92.117</average_molecular_weight>
  <monisotopic_moleculate_weight>91.993200062</monisotopic_moleculate_weight>
  <iupac_name>2-sulfanylacetic acid</iupac_name>
  <traditional_iupac>thioglycolic acid</traditional_iupac>
  <cas_registry_number>68-11-1</cas_registry_number>
  <smiles>OC(=O)CS</smiles>
  <inchi>InChI=1S/C2H4O2S/c3-2(4)1-5/h5H,1H2,(H,3,4)</inchi>
  <inchikey>CWERGRDVMFNCDR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Carboxylic acids</sub_class>
    <direct_parent>alpha-Mercaptocarboxylic acids</direct_parent>
    <alternate_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>2-mercaptocarboxylic acid</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organosulfur compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>sulfur-containing carboxylic acid</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>0.0032</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.26e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.0032</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-sulfanylacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>92.117</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>91.993200062</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H4O2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H4O2S/c3-2(4)1-5/h5H,1H2,(H,3,4)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CWERGRDVMFNCDR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>20.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7279912088&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB15429</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>1133</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>1101</chemspider_id>
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</compound>
