<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:00 UTC</creation_date>
  <update_date>2025-11-18 22:31:56 UTC</update_date>
  <accession>FDB001538</accession>
  <name>Tetramethoxyluteolin</name>
  <description>Tetramethoxyluteolin, also known as 3'4'57-tetramethoxyflavone or 3',4',5,7-tetramethyl-luteolin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, tetramethoxyluteolin is considered to be a flavonoid lipid molecule. Tetramethoxyluteolin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Tetramethoxyluteolin can be found in mandarin orange (clementine, tangerine), which makes tetramethoxyluteolin a potential biomarker for the consumption of this food product. </description>
  <synonyms>
    <synonym>2-(3,4-Dimethoxyphenyl)-5,7-dimethoxy-4H-1-benzopyran-4-one</synonym>
    <synonym>3',4',5,7-Tetramethoxyflavone</synonym>
    <synonym>3',4',5,7-Tetramethylluteolin</synonym>
    <synonym>5,7,3',4'-Tetramethoxyflavone</synonym>
    <synonym>5,7,3',4'-Tetramethylluteolin</synonym>
    <synonym>Anisopirol</synonym>
    <synonym>Luteolin 5,7,3',4'-tetramethyl ether</synonym>
    <synonym>Luteolin tetramethyl ether</synonym>
    <synonym>Luteolin tetramethylether</synonym>
    <synonym>Tetramethoxyluteolin</synonym>
  </synonyms>
  <chemical_formula>C19H18O6</chemical_formula>
  <average_molecular_weight>342.3426</average_molecular_weight>
  <monisotopic_moleculate_weight>342.110338308</monisotopic_moleculate_weight>
  <iupac_name>2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one</iupac_name>
  <traditional_iupac>2-(3,4-dimethoxyphenyl)-5,7-dimethoxychromen-4-one</traditional_iupac>
  <cas_registry_number>855-97-0</cas_registry_number>
  <smiles>COC1=CC2=C(C(=O)C=C(O2)C2=CC=C(OC)C(OC)=C2)C(OC)=C1</smiles>
  <inchi>InChI=1S/C19H18O6/c1-21-12-8-17(24-4)19-13(20)10-15(25-18(19)9-12)11-5-6-14(22-2)16(7-11)23-3/h5-10H,1-4H3</inchi>
  <inchikey>CLXVBVLQKLQNRQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.</description>
    <direct_parent>7-O-methylated flavonoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Flavonoids</class>
    <sub_class>O-methylated flavonoids</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>3'-O-methylated flavonoids</alternative_parent>
      <alternative_parent>4'-O-methylated flavonoids</alternative_parent>
      <alternative_parent>5-O-methylated flavonoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Chromones</alternative_parent>
      <alternative_parent>Dimethoxybenzenes</alternative_parent>
      <alternative_parent>Flavones</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Pyranones and derivatives</alternative_parent>
      <alternative_parent>Vinylogous esters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>3p-methoxyflavonoid-skeleton</substituent>
      <substituent>4p-methoxyflavonoid-skeleton</substituent>
      <substituent>5-methoxyflavonoid-skeleton</substituent>
      <substituent>7-methoxyflavonoid-skeleton</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Chromone</substituent>
      <substituent>Dimethoxybenzene</substituent>
      <substituent>Ether</substituent>
      <substituent>Flavone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>O-dimethoxybenzene</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyranone</substituent>
      <substituent>Vinylogous ester</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Flavones and Flavonols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.00e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.34</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>15.41</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>342.3426</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>342.110338308</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC2=C(C(=O)C=C(O2)C2=CC=C(OC)C(OC)=C2)C(OC)=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C19H18O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C19H18O6/c1-21-12-8-17(24-4)19-13(20)10-15(25-18(19)9-12)11-5-6-14(22-2)16(7-11)23-3/h5-10H,1-4H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>CLXVBVLQKLQNRQ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>63.22</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>92.82</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>36.05</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>6</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::MsMs</type>
      <spectrum_id>78126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>78127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>78128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>138393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>138394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>138395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3597706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3597707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3597708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3597709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3597710</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Mandarin orange (Clementine, Tangerine)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus reticulata</name_scientific>
      <ncbi_taxonomy_id>85571</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
