<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:26 UTC</creation_date>
  <update_date>2025-11-18 22:38:29 UTC</update_date>
  <accession>FDB002584</accession>
  <name>Chrysophanol</name>
  <description>Constituent of Rumex, Rheum subspecies Chrysophanol is found in dock, garden rhubarb, and sorrel.</description>
  <synonyms>
    <synonym>1,8-dihydroxy-3-methyl-9,10-anthracenedione</synonym>
    <synonym>1,8-Dihydroxy-3-methyl-9,10-anthracenedione, 9CI</synonym>
    <synonym>1,8-dihydroxy-3-methyl-9,10-anthraquinone</synonym>
    <synonym>1,8-Dihydroxy-3-methyl-anthraquinone</synonym>
    <synonym>1,8-dihydroxy-3-methylanthra-9,10-quinone</synonym>
    <synonym>1,8-Dihydroxy-3-methylanthraquinone</synonym>
    <synonym>2-Methyl-4,5-dihydroxyanthraquinone</synonym>
    <synonym>3-Methyl-1, 8-dihydroxyanthraquinone</synonym>
    <synonym>3-Methyl-1,8-dihydroxyanthraquinone</synonym>
    <synonym>3-Methylchrysazin</synonym>
    <synonym>4, 5-Dihydroxy-2-methylanthraquinone</synonym>
    <synonym>4,5-Dihydroxy-2-methylanthraquinone</synonym>
    <synonym>9,10-Anthracenedione, 1, 8-dihydroxy-3-methyl-</synonym>
    <synonym>9,10-Anthracenedione, 1,8-dihydroxy-3-methyl-</synonym>
    <synonym>9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- (9CI)</synonym>
    <synonym>Anthraquinone, 1,8-dihydroxy-3-methyl-</synonym>
    <synonym>Archinin</synonym>
    <synonym>C.I. Natural Yellow 23</synonym>
    <synonym>Chrysophanate</synonym>
    <synonym>Chrysophanic acid</synonym>
    <synonym>Chrysophanic acid (1,8-dihydroxy-3-methylanthraquinone)</synonym>
    <synonym>Chrysophanol</synonym>
    <synonym>Chrysophansaeure</synonym>
    <synonym>Crysophanic acid</synonym>
    <synonym>Crysophanol</synonym>
    <synonym>Rheic acid</synonym>
    <synonym>Rumicin</synonym>
    <synonym>Turkey rhubarb</synonym>
  </synonyms>
  <chemical_formula>C15H10O4</chemical_formula>
  <average_molecular_weight>254.2375</average_molecular_weight>
  <monisotopic_moleculate_weight>254.057908808</monisotopic_moleculate_weight>
  <iupac_name>1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione</iupac_name>
  <traditional_iupac>turkey rhubarb</traditional_iupac>
  <cas_registry_number>481-74-3</cas_registry_number>
  <smiles>CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O</smiles>
  <inchi>InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3</inchi>
  <inchikey>LQGUBLBATBMXHT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.</description>
    <direct_parent>Anthraquinones</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Anthracenes</class>
    <sub_class>Anthraquinones</sub_class>
    <molecular_framework>Aromatic homopolycyclic 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>Aryl ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>9,10-anthraquinone</substituent>
      <substituent>Anthraquinone</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Aryl ketone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Anthracenes and phenanthrenes</external_descriptor>
      <external_descriptor>Anthracenes and phenanthrenes</external_descriptor>
      <external_descriptor>Anthraquinone type</external_descriptor>
      <external_descriptor>a hydroxyanthraquinone</external_descriptor>
      <external_descriptor>hydroxyanthraquinones</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.25e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 200-201° (196°)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.14</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>254.2375</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>254.057908808</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C15H10O4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>LQGUBLBATBMXHT-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>74.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>70.15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>25.51</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>42075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>174941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2227237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2227490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2234350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2234572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2255394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2398134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2398135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2398136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2536787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2536788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2536789</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB30670</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>3687</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x00007f093c10bb60&gt;</reference>
    <reference>#&lt;Reference:0x00007f093c10b9a8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Dock</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rumex</name_scientific>
      <ncbi_taxonomy_id>3618</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garden rhubarb</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rheum rhabarbarum</name_scientific>
      <ncbi_taxonomy_id>3621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sorrel</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rumex acetosa</name_scientific>
      <ncbi_taxonomy_id>41241</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti bacterial</name>
      <id>145</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Anti septic</name>
      <id>603</id>
      <definition>A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-spasmodic</name>
      <id>619</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Calcium antagonist</name>
      <id>748</id>
      <definition>Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.</definition>
    </health_effect>
    <health_effect>
      <name>Candidicide</name>
      <id>756</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Cathartic</name>
      <id>784</id>
      <definition>Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic.</definition>
    </health_effect>
    <health_effect>
      <name>Fungicide</name>
      <id>940</id>
      <definition>A substance used to destroy fungal pests.</definition>
    </health_effect>
    <health_effect>
      <name>Hemostat</name>
      <id>976</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Keratitigenic</name>
      <id>1059</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Oculoirritant</name>
      <id>1172</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_effect>
      <name>Pigment</name>
      <id>1227</id>
      <definition>An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.</definition>
    </health_effect>
    <health_effect>
      <name>Purgative</name>
      <id>1275</id>
      <definition>An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.</definition>
    </health_effect>
    <health_effect>
      <name>Termitifuge</name>
      <id>1350</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>
