<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:22 UTC</creation_date>
  <update_date>2025-11-18 22:37:29 UTC</update_date>
  <accession>FDB002440</accession>
  <name>Tricin</name>
  <description>5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one, also known as 3',5'-O-dimethyltricetin or 5,7,4'-trihydroxy-3',5'-dimethoxy-flavone, is a member of the class of compounds known as 3'-o-methylated flavonoids. 3'-o-methylated flavonoids are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone. Thus, 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one can be synthesized from tricetin. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is also a parent compound for other transformation products, including but not limited to, tricin 7-O-glucoside, 4'-O-beta-glucosyl-7-O-(6-O-sinapoylglucosyl)tricin, and tricin 7-O-(6''-O-malonyl)-beta-D-glucopyranoside. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one can be found in barley, common wheat, oat, and rice, which makes 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one a potential biomarker for the consumption of these food products.</description>
  <synonyms>
    <synonym>5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-one, 9CI</synonym>
    <synonym>Phelipeone</synonym>
    <synonym>Phoelipeone</synonym>
    <synonym>Tricetin 3',5'-dimethyl ether</synonym>
    <synonym>Tricin</synonym>
  </synonyms>
  <chemical_formula>C17H14O7</chemical_formula>
  <average_molecular_weight>330.2889</average_molecular_weight>
  <monisotopic_moleculate_weight>330.073952802</monisotopic_moleculate_weight>
  <iupac_name>5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one</iupac_name>
  <traditional_iupac>tricin</traditional_iupac>
  <cas_registry_number>520-32-1</cas_registry_number>
  <smiles>COC1=CC(=CC(OC)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O1</smiles>
  <inchi>InChI=1S/C17H14O7/c1-22-14-3-8(4-15(23-2)17(14)21)12-7-11(20)16-10(19)5-9(18)6-13(16)24-12/h3-7,18-19,21H,1-2H3</inchi>
  <inchikey>HRGUSFBJBOKSML-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.</description>
    <direct_parent>3'-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>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>4'-hydroxyflavonoids</alternative_parent>
      <alternative_parent>5-hydroxyflavonoids</alternative_parent>
      <alternative_parent>7-hydroxyflavonoids</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>Methoxyphenols</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 acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>3p-methoxyflavonoid-skeleton</substituent>
      <substituent>4'-hydroxyflavonoid</substituent>
      <substituent>5-hydroxyflavonoid</substituent>
      <substituent>7-hydroxyflavonoid</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>Hydroxyflavonoid</substituent>
      <substituent>M-dimethoxybenzene</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyranone</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Flavones and Flavonols</external_descriptor>
      <external_descriptor>Flavones and Flavonols</external_descriptor>
      <external_descriptor>dimethoxyflavone</external_descriptor>
      <external_descriptor>flavones</external_descriptor>
      <external_descriptor>trihydroxyflavone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.96e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.39</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>6.57</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>330.2889</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>330.073952802</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC(=CC(OC)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C17H14O7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C17H14O7/c1-22-14-3-8(4-15(23-2)17(14)21)12-7-11(20)16-10(19)5-9(18)6-13(16)24-12/h3-7,18-19,21H,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>HRGUSFBJBOKSML-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>105.45</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>85.84</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>32.75</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::MsMs</type>
      <spectrum_id>108279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2782654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2782655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2782656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2926150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2926151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2926152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>50676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>159233</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>Amaranth</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Amaranthus</name_scientific>
      <ncbi_taxonomy_id>3564</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Annual wild rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zizania aquatica</name_scientific>
      <ncbi_taxonomy_id>75727</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Barley</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hordeum vulgare</name_scientific>
      <ncbi_taxonomy_id>4513</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Breakfast cereal</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Bulgur</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Cereals and cereal products</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Common buckwheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Fagopyrum esculentum</name_scientific>
      <ncbi_taxonomy_id>3617</ncbi_taxonomy_id>
    </food>
    <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>Corn</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
      <ncbi_taxonomy_id>4577</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Flour</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Hard wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum durum</name_scientific>
      <ncbi_taxonomy_id>4567</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Millet</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Panicum miliaceum</name_scientific>
      <ncbi_taxonomy_id>4540</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Oat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Avena sativa</name_scientific>
      <ncbi_taxonomy_id>4498</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Oriental wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum turanicum</name_scientific>
      <ncbi_taxonomy_id>376534</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Quinoa</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Chenopodium quinoa</name_scientific>
      <ncbi_taxonomy_id>63459</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Red rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryza rufipogon</name_scientific>
      <ncbi_taxonomy_id>4529</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryza sativa</name_scientific>
      <ncbi_taxonomy_id>4530</ncbi_taxonomy_id>
      <average_value>0.0066</average_value>
      <max_value>0.0066</max_value>
      <min_value>0.0066</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Rye</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Secale cereale</name_scientific>
      <ncbi_taxonomy_id>4550</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sorghum</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sorghum bicolor</name_scientific>
      <ncbi_taxonomy_id>4558</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Soy bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Glycine max</name_scientific>
      <ncbi_taxonomy_id>3847</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Spelt</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum spelta</name_scientific>
      <ncbi_taxonomy_id>58933</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Tartary buckwheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Fagopyrum tataricum</name_scientific>
      <ncbi_taxonomy_id>62330</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Teff</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Eragrostis tef</name_scientific>
      <ncbi_taxonomy_id>110835</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Triticale</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>X Triticosecale rimpaui</name_scientific>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum</name_scientific>
      <ncbi_taxonomy_id>4564</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zizania</name_scientific>
      <ncbi_taxonomy_id>15949</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Allelopathic</name>
      <id>42</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti cariogenic</name>
      <id>165</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti leukemic</name>
      <id>393</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-oxidant</name>
      <id>502</id>
      <definition>A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.</definition>
    </health_effect>
    <health_effect>
      <name>Antitumor</name>
      <id>672</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Catabolic</name>
      <id>780</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Cyclooxygenase inhibitor</name>
      <id>849</id>
      <definition>A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.</definition>
    </health_effect>
    <health_effect>
      <name>Estrogenic</name>
      <id>922</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Herbistat</name>
      <id>987</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Pesticide</name>
      <id>1210</id>
      <definition>Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.</definition>
    </health_effect>
  </health_effects>
</compound>
