<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:15:12 UTC</creation_date>
  <update_date>2025-11-19 02:33:23 UTC</update_date>
  <accession>FDB020713</accession>
  <name>Glycyrrhetic acid</name>
  <description>Aglycone from licorice (Glycyrrhiza glabra)

Glycyrrhetinic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice. It is used in flavoring and it masks the bitter taste of drugs like aloe and quinine. Glycyrrhetic acid is found in tea and herbs and spices.</description>
  <synonyms>
    <synonym>&amp;alpha;-Glycyrrhetinic acid</synonym>
    <synonym>18-beta-Glycyrrhetic acid</synonym>
    <synonym>18&amp;beta;-Glycyrrhetic acid</synonym>
    <synonym>18&amp;beta;-Glycyrrhetinic acid</synonym>
    <synonym>18&amp;beta;-Glycyrrhtinic acid</synonym>
    <synonym>18b-Glycyrrhetic acid</synonym>
    <synonym>18b-Glycyrrhetinic acid</synonym>
    <synonym>18b-Glycyrrhtinic acid</synonym>
    <synonym>18beta-Glycyrrhetic acid</synonym>
    <synonym>18beta-Glycyrrhetinic acid</synonym>
    <synonym>3-Glycyrrhetinic acid</synonym>
    <synonym>3-Hydroxy-11-oxoolean-12-en-29-Oate</synonym>
    <synonym>3-Hydroxy-11-oxoolean-12-en-29-Oic acid</synonym>
    <synonym>3-Hydroxy-11-oxoolean-12-en-29-Oic acid (acd/name 4.0)</synonym>
    <synonym>3b-Hydroxy-11-oxo-olean-12-en-30-Oate</synonym>
    <synonym>3b-Hydroxy-11-oxo-olean-12-en-30-Oic acid</synonym>
    <synonym>3b-Hydroxy-11-oxoolean-12-en-30-Oate</synonym>
    <synonym>3b-Hydroxy-11-oxoolean-12-en-30-Oic acid</synonym>
    <synonym>3beta-Hydroxy-11-oxo-18beta,20beta-olean-12-en-29-oic acid</synonym>
    <synonym>a-Glycyrrhetinic acid</synonym>
    <synonym>alpha-Glycyrrhetinic acid</synonym>
    <synonym>b-Glycyrrhetic acid</synonym>
    <synonym>beta-Glycyrrhetic acid</synonym>
    <synonym>Biogastrone acid</synonym>
    <synonym>Biosone</synonym>
    <synonym>Enoxolone</synonym>
    <synonym>Glycyrrhetic acid</synonym>
    <synonym>Glycyrrhetin</synonym>
    <synonym>Glycyrrhetinate</synonym>
    <synonym>Glycyrrhetinic acid</synonym>
    <synonym>Glycyrrhitinic acid</synonym>
    <synonym>Rhetinic acid</synonym>
    <synonym>Uralenic acid</synonym>
  </synonyms>
  <chemical_formula>C30H46O4</chemical_formula>
  <average_molecular_weight>470.694</average_molecular_weight>
  <monisotopic_moleculate_weight>470.339609961</monisotopic_moleculate_weight>
  <iupac_name>(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid</iupac_name>
  <traditional_iupac>jintan</traditional_iupac>
  <cas_registry_number>471-53-4</cas_registry_number>
  <smiles>[H][C@@]12C[C@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O</smiles>
  <inchi>InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1</inchi>
  <inchikey>MPDGHEJMBKOTSU-YKLVYJNSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <direct_parent>Triterpenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Oleanane triterpenoids</external_descriptor>
      <external_descriptor>Oleananes</external_descriptor>
      <external_descriptor>cyclic terpene ketone</external_descriptor>
      <external_descriptor>hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>pentacyclic triterpenoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.72e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 300-304°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>6.03</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.44</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.84</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>470.694</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>470.339609961</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@@]12C[C@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C30H46O4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>MPDGHEJMBKOTSU-YKLVYJNSSA-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>134.27</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>55.17</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</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>-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>109131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436526</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB11628</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>30853</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Black tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Green tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Herbal tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Red tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Tea</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Camellia sinensis</name_scientific>
      <ncbi_taxonomy_id>4442</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
