<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:04:44 UTC</creation_date>
  <update_date>2025-11-18 22:25:09 UTC</update_date>
  <accession>FDB000858</accession>
  <name>2,6-Dimethoxy-1,4-benzoquinone</name>
  <description>Constituent of bark of Phyllostachys heterocycla variety pubescens (moso bamboo). 2,6-Dimethoxy-1,4-benzoquinone is found in green vegetables and common wheat.</description>
  <synonyms>
    <synonym>2, 6-Dimethoxy-1,4-benzoquinone</synonym>
    <synonym>2, 6-Dimethoxy-p-benzoquinone</synonym>
    <synonym>2, 6-Dimethoxyquinone</synonym>
    <synonym>2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy-</synonym>
    <synonym>2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy- (9CI)</synonym>
    <synonym>2,6-Dimethoxy-1,4-benzoquinone</synonym>
    <synonym>2,6-Dimethoxy-2,5-cyclohexadiene-1,4-dione</synonym>
    <synonym>2,6-Dimethoxy-p-benzoquinone</synonym>
    <synonym>2,6-Dimethoxy-p-quinone</synonym>
    <synonym>2,6-Dimethoxybenzo-1,4-quinone</synonym>
    <synonym>2,6-Dimethoxybenzoquinone</synonym>
    <synonym>2,6-Dimethoxyquinone</synonym>
    <synonym>2,6-dimethoxysemiquinone Anions</synonym>
    <synonym>2,6-Dimethoxysemiquinone radicals</synonym>
    <synonym>2,6-Dimetoxy-P-benzoquinone</synonym>
    <synonym>DIMETHOXYBENZOQUINONE,2,6-</synonym>
    <synonym>DMBQ</synonym>
    <synonym>ghl.PD_Mitscher_leg0.4</synonym>
    <synonym>p-Benzoquinone, 2,6-dimethoxy-</synonym>
  </synonyms>
  <chemical_formula>C8H8O4</chemical_formula>
  <average_molecular_weight>168.1467</average_molecular_weight>
  <monisotopic_moleculate_weight>168.042258744</monisotopic_moleculate_weight>
  <iupac_name>2,6-dimethoxycyclohexa-2,5-diene-1,4-dione</iupac_name>
  <traditional_iupac>2,6-dimethoxy-1,4-benzoquinone</traditional_iupac>
  <cas_registry_number>530-55-2</cas_registry_number>
  <smiles>COC1=CC(=O)C=C(OC)C1=O</smiles>
  <inchi>InChI=1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3</inchi>
  <inchikey>OLBNOBQOQZRLMP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.</description>
    <direct_parent>P-benzoquinones</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Vinylogous esters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>P-benzoquinone</substituent>
      <substituent>Vinylogous ester</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>benzoquinones</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.05e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 252°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2,6-dimethoxycyclohexa-2,5-diene-1,4-dione</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>168.1467</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>168.042258744</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC(=O)C=C(OC)C1=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C8H8O4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>OLBNOBQOQZRLMP-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>52.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>44.47</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>15.54</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>0</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>131377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>139111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>3579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>3580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2814508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2814509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2814510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2890932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2890933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2890934</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB29673</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id>KIA</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x00007f093c0d3990&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Common wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum aestivum</name_scientific>
      <ncbi_taxonomy_id>4565</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Green vegetables</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
