<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:36:14 UTC</creation_date>
  <update_date>2026-05-14 19:31:02 UTC</update_date>
  <accession/>
  <common_name>Phenol red</common_name>
  <class>SmallMolecule</class>
  <description>Phenol red is an organic compound with the chemical formula C19H14O5S and an average molecular weight of 354.38 g/mol. Phenol red belongs to the benzofuranones, a subclass of benzofurans within the organic compounds. In industrial applications, the compound serves as an indicator and a pH regulating agent (PMC6722136).

The substance is associated with 25 recorded sources of release or presence. Within electrical and electronic equipment, it is found in antennas, amplifiers, discharge lamps, electric switches, conductors or conductive bodies characterised by the conductive materials, and nine additional sources. In the category of food, food processing and cookware, it is linked to the treatment of hops, food preservation, fermentation processes for beer, the preparation of vinegar, and the processing of meats. Furthermore, phenol red is found in household items such as key rings and various household cleaning and consumer products, including soap detergents, bleaching agents, pipe accessories, cigar cigarettes, and tobacco smoke filters.</description>
  <categories/>
  <types>
    <type>Phenolic Antioxidant</type>
  </types>
  <synonyms>
    <synonym>3,3-bis(4-hydroxyphenyl)-3H-2,1λ⁶-benzoxathiole-1,1-dione</synonym>
  </synonyms>
  <chemical_formula>C19H14O5S</chemical_formula>
  <average_molecular_weight>354.38</average_molecular_weight>
  <monisotopic_moleculate_weight>354.056194725</monisotopic_moleculate_weight>
  <iupac_name>3,3-bis(4-hydroxyphenyl)-3H-2,1λ⁶-benzoxathiole-1,1-dione</iupac_name>
  <traditional_iupac>phenol red</traditional_iupac>
  <cas_registry_number>143-74-8</cas_registry_number>
  <smiles>OC1=CC=C(C=C1)C1(OS(=O)(=O)C2=CC=CC=C12)C1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C19H14O5S/c20-15-9-5-13(6-10-15)19(14-7-11-16(21)12-8-14)17-3-1-2-4-18(17)25(22,23)24-19/h1-12,20-21H</inchi>
  <inchikey>BELBBZDIHDAJOR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Benzofurans</class>
    <sub_class>Benzofuranones</sub_class>
    <direct_parent>Benzofuranones</direct_parent>
    <alternate_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Benzoxathioles</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organosulfonic acid esters</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Phthalides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzofuranone</substituent>
      <substituent>Benzoxathiole</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organosulfonic acid ester</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phthalide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>2,1-benzoxathiole</descriptor>
      <descriptor>arenesulfonate ester</descriptor>
      <descriptor>phenols</descriptor>
      <descriptor>sultone</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>4.11</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.80e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3,3-bis(4-hydroxyphenyl)-3H-2,1λ⁶-benzoxathiole-1,1-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>354.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>354.056194725</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC1=CC=C(C=C1)C1(OS(=O)(=O)C2=CC=CC=C12)C1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H14O5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H14O5S/c20-15-9-5-13(6-10-15)19(14-7-11-16(21)12-8-14)17-3-1-2-4-18(17)25(22,23)24-19/h1-12,20-21H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BELBBZDIHDAJOR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>94.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
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  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bd00cc638&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB13212</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4766</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4602</chemspider_id>
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  <biocyc_id/>
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  <wikipidia/>
  <general_references/>
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</compound>
