<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:54 UTC</creation_date>
  <update_date>2025-11-19 00:35:40 UTC</update_date>
  <accession>FDB013795</accession>
  <name>1,2-Epoxy-p-menth-8-ene</name>
  <description>Isolated from oil of Cymbopogon subspecies, orange (Citrus sinensis), Japanese pepper tree (Zanthoxylum piperitum) and others. 1,2-Epoxy-p-menth-8-ene is found in spearmint, citrus, and herbs and spices.</description>
  <synonyms>
    <synonym>1-Methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane, 9CI</synonym>
    <synonym>1-Methyl-4-(1-methylvinyl)-7-oxabicyclo(4.1.0)heptane</synonym>
    <synonym>1-Methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane</synonym>
    <synonym>1,2-Epoxylimonene</synonym>
    <synonym>4-Isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptane</synonym>
    <synonym>Limonene 1,2-epoxide</synonym>
    <synonym>Limonene 1,2-oxide</synonym>
    <synonym>Limonene epoxide</synonym>
    <synonym>Limonene monoxide</synonym>
    <synonym>Limonene oxide</synonym>
    <synonym>Limonene-1,2-epoxide</synonym>
  </synonyms>
  <chemical_formula>C10H16O</chemical_formula>
  <average_molecular_weight>152.2334</average_molecular_weight>
  <monisotopic_moleculate_weight>152.120115134</monisotopic_moleculate_weight>
  <iupac_name>1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane</iupac_name>
  <traditional_iupac>limonene 1,2-epoxide</traditional_iupac>
  <cas_registry_number>1195-92-2</cas_registry_number>
  <smiles>CC(=C)C1CCC2(C)OC2C1</smiles>
  <inchi>InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3</inchi>
  <inchikey>CCEFMUBVSUDRLG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.</description>
    <direct_parent>Oxepanes</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Oxepanes</class>
    <sub_class/>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Epoxides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxepane</substituent>
      <substituent>Oxirane</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a 4S-limonene-1,2-epoxide</external_descriptor>
      <external_descriptor>epoxide</external_descriptor>
      <external_descriptor>limonene monoterpenoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.51e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>152.2334</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>152.120115134</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(=C)C1CCC2(C)OC2C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H16O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>CCEFMUBVSUDRLG-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>12.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>45.24</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>18.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</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>18289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>101714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>131106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>138840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2407922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2407923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2407924</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2531574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2531575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2531576</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB35158</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>16431</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31d3f770&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Citrus</name>
      <food_type>Unknown</food_type>
      <category>generic</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>Spearmint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha spicata</name_scientific>
      <ncbi_taxonomy_id>29719</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>fruit</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
