<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:12:46 UTC</creation_date>
  <update_date>2015-07-20 23:34:35 UTC</update_date>
  <accession>FDB016985</accession>
  <name>4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid</name>
  <description>Food dye; no longer permitted in the EU</description>
  <synonyms>
    <synonym>2',4'-Dihydroxyazobenzene-4-sulfonic acid</synonym>
    <synonym>4-((2,4-Dihydroxyphenyl)azo)benzenesulphonic acid</synonym>
    <synonym>4-((2,4-Dihydroxyphenyl)diazenyl)benzenesulfonic acid</synonym>
    <synonym>4-[(2,4-Dihydoxyphenyl)azo]-1-benzenesulfonic acid-</synonym>
    <synonym>C.I. 14270</synonym>
    <synonym>C.I. Acid orange 6</synonym>
    <synonym>C.I. Food yellow 8</synonym>
    <synonym>Chrysoine S</synonym>
    <synonym>E 103</synonym>
    <synonym>Resorcinol yellow</synonym>
    <synonym>Tropaeolin O</synonym>
  </synonyms>
  <chemical_formula>C12H10N2O5S</chemical_formula>
  <average_molecular_weight>294.283</average_molecular_weight>
  <monisotopic_moleculate_weight>294.03104213</monisotopic_moleculate_weight>
  <iupac_name>4-[2-(2,4-dihydroxyphenyl)diazen-1-yl]benzene-1-sulfonic acid</iupac_name>
  <traditional_iupac>4-[2-(2,4-dihydroxyphenyl)diazen-1-yl]benzenesulfonic acid</traditional_iupac>
  <cas_registry_number>2050-34-2</cas_registry_number>
  <smiles>OC1=CC(O)=C(C=C1)N=NC1=CC=C(C=C1)S(O)(=O)=O</smiles>
  <inchi>InChI=1S/C12H10N2O5S/c15-9-3-6-11(12(16)7-9)14-13-8-1-4-10(5-2-8)20(17,18)19/h1-7,15-16H,(H,17,18,19)</inchi>
  <inchikey>MHKGJUOEEHNBLE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.</description>
    <direct_parent>Azobenzenes</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azobenzenes</class>
    <sub_class/>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-sulfo,2-unsubstituted aromatic compounds</alternative_parent>
      <alternative_parent>Azo compounds</alternative_parent>
      <alternative_parent>Benzenesulfonic acids and derivatives</alternative_parent>
      <alternative_parent>Benzenesulfonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonic acids</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Resorcinols</alternative_parent>
      <alternative_parent>Sulfonyls</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>1-sulfo,2-unsubstituted aromatic compound</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Arylsulfonic acid or derivatives</substituent>
      <substituent>Azo compound</substituent>
      <substituent>Azobenzene</substituent>
      <substituent>Benzenesulfonate</substituent>
      <substituent>Benzenesulfonyl group</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Resorcinol</substituent>
      <substituent>Sulfonyl</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.53e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.89</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>-4.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.37</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4-[2-(2,4-dihydroxyphenyl)diazen-1-yl]benzene-1-sulfonic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>294.283</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>294.03104213</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC1=CC(O)=C(C=C1)N=NC1=CC=C(C=C1)S(O)(=O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C12H10N2O5S</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C12H10N2O5S/c15-9-3-6-11(12(16)7-9)14-13-8-1-4-10(5-2-8)20(17,18)19/h1-7,15-16H,(H,17,18,19)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>MHKGJUOEEHNBLE-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>119.55</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>74.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>28.11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>45567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>130813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>138547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>97875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>97876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>97877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>162678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>162679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>162680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2360855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2360856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2360857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2605508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2605509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2605510</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB37835</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce33344d18&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
