<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:30 UTC</creation_date>
  <update_date>2025-11-18 22:40:07 UTC</update_date>
  <accession>FDB002729</accession>
  <name>(Z)-Isoeugenol</name>
  <description>(z)-isoeugenol, also known as (Z)-2-methoxy-4-propenylphenol or cis-4-propenylguaiacol, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety (z)-isoeugenol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (z)-isoeugenol is a clove and spicy tasting compound found in cloves, which makes (z)-isoeugenol a potential biomarker for the consumption of this food product. </description>
  <synonyms>
    <synonym>(Z)-2-Methoxy-4-(prop-1-enyl)phenol</synonym>
    <synonym>(Z)-2-methoxy-4-propenylphenol</synonym>
    <synonym>(z)-isoeugenol</synonym>
    <synonym>2-Methoxy-4-[(1Z)-1-propenyl]phenol</synonym>
    <synonym>2-methoxy-4-[(1Z)-prop-1-en-1-yl]phenol</synonym>
    <synonym>4-(1-Propenyl)-2-methoxyphenol (cis-isoeugenol)</synonym>
    <synonym>cis-2-Methoxy-4-propenylphenol</synonym>
    <synonym>cis-4-Propenylguaiacol</synonym>
    <synonym>Cis-isoeugenol</synonym>
    <synonym>Isoeugenol (z)</synonym>
    <synonym>Isoeugenol cis-form</synonym>
    <synonym>Isoeugenol z</synonym>
    <synonym>Phenol, 2-methoxy-4-(1-propenyl)-, (Z)-</synonym>
    <synonym>Phenol, 2-methoxy-4-propenyl-, (Z)-</synonym>
    <synonym>Z-Isoeugenol</synonym>
  </synonyms>
  <chemical_formula>C10H12O2</chemical_formula>
  <average_molecular_weight>164.2011</average_molecular_weight>
  <monisotopic_moleculate_weight>164.083729628</monisotopic_moleculate_weight>
  <iupac_name>2-methoxy-4-[(1Z)-prop-1-en-1-yl]phenol</iupac_name>
  <traditional_iupac>cis-isoeugenol</traditional_iupac>
  <cas_registry_number>5912-86-7</cas_registry_number>
  <smiles>[H]\C(C)=C(/[H])C1=CC(OC)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3-</inchi>
  <inchikey>BJIOGJUNALELMI-ARJAWSKDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <direct_parent>Methoxyphenols</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>isoeugenol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>liquid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.36e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>-10 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.64</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>10.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-methoxy-4-[(1Z)-prop-1-en-1-yl]phenol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>164.2011</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>164.083729628</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H]\C(C)=C(/[H])C1=CC(OC)=C(O)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H12O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>BJIOGJUNALELMI-ARJAWSKDSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>29.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>49.86</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>17.92</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>1</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>98932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141812</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>50543</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Cloves</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Syzygium aromaticum</name_scientific>
      <ncbi_taxonomy_id>219868</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>clove</name>
    </flavor>
    <flavor>
      <name>spicy</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
