<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:54 UTC</creation_date>
  <update_date>2025-11-18 23:32:13 UTC</update_date>
  <accession>FDB011933</accession>
  <name>Piperic acid</name>
  <description>obtained from black pepper (Piper nigrum), from Minthostachys verticillata, peppermint (Mentha piperita) and others. Piperic acid is found in herbs and spices and pepper (spice).</description>
  <synonyms>
    <synonym>2,4-Pentadienoic acid, 5-(1, 3-benzodioxol-5-yl)-</synonym>
    <synonym>2,4-Pentadienoic acid, 5-(1,3-benzodioxol-5-yl)-</synonym>
    <synonym>2,4-Pentadienoic acid, 5-(1,3-benzodioxol-5-yl)- (9CI)</synonym>
    <synonym>5-(1,3-Benzenedioxol-5-yl)-2,4-pentadienoic acid, 9CI</synonym>
    <synonym>5-(1,3-benzodioxol-5-yl)-2,4-pentadienoic acid</synonym>
    <synonym>5-(1,3-Benzodioxol-5-yl)penta-2,4-dienoic acid</synonym>
    <synonym>Piperic acid</synonym>
    <synonym>Piperic acid (8CI)</synonym>
    <synonym>Piperic acid, 8CI</synonym>
    <synonym>Piperinic acid</synonym>
    <synonym>Piperonic acid</synonym>
  </synonyms>
  <chemical_formula>C12H10O4</chemical_formula>
  <average_molecular_weight>218.2054</average_molecular_weight>
  <monisotopic_moleculate_weight>218.057908808</monisotopic_moleculate_weight>
  <iupac_name>(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid</iupac_name>
  <traditional_iupac>(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid</traditional_iupac>
  <cas_registry_number>5285-18-7</cas_registry_number>
  <smiles>OC(=O)\C=C\C=C/C1=CC2=C(OCO2)C=C1</smiles>
  <inchi>InChI=1S/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1-,4-2+</inchi>
  <inchikey>RHBGITBPARBDPH-HSFFGMMNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.</description>
    <direct_parent>Benzodioxoles</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Benzodioxoles</class>
    <sub_class/>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heterocyclic fatty acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzodioxole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Heterocyclic fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Styrene</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.13e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>215 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.29</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>3.82</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>218.2054</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>218.057908808</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC(=O)\C=C\C=C/C1=CC2=C(OCO2)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C12H10O4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1-,4-2+</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>RHBGITBPARBDPH-HSFFGMMNSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>55.76</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>59.15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>21.47</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>1</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::CMs</type>
      <spectrum_id>12699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>43499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>174746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2813732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2813733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2813734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2891640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2891641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2891642</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB33779</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32b9ecd0&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Pepper (Spice)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Piper nigrum</name_scientific>
      <ncbi_taxonomy_id>13216</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
