<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:59 UTC</creation_date>
  <update_date>2025-11-18 22:54:11 UTC</update_date>
  <accession>FDB003863</accession>
  <name>p-Mentha-2,4(8)-diene</name>
  <description>P-mentha-2,4(8)-diene is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-mentha-2,4(8)-diene can be found in dill, which makes P-mentha-2,4(8)-diene a potential biomarker for the consumption of this food product. P-mentha-2,4(8)-diene can be found primarily in saliva. </description>
  <synonyms>
    <synonym>2,4(8)-p-Menthadiene</synonym>
    <synonym>3-Isopropylidene-6-methyl-cyclohexene</synonym>
    <synonym>3-Methyl-6-(1-methylethylidene)-1-cyclohexene</synonym>
    <synonym>3-Methyl-6-(1-methylethylidene)-cyclohexene</synonym>
    <synonym>3-Methyl-6-(1-methylethylidene)cyclohexene</synonym>
    <synonym>Cyclohexene, 3-methyl-6-(1-methylethylidene)-</synonym>
    <synonym>Isoterpinolene</synonym>
    <synonym>p-2,4(8)-Menthadiene</synonym>
    <synonym>p-Mentha-2,4(8)-diene</synonym>
    <synonym>para-mentha-2,4(8)-diene</synonym>
  </synonyms>
  <chemical_formula>C10H16</chemical_formula>
  <average_molecular_weight>136.234</average_molecular_weight>
  <monisotopic_moleculate_weight>136.125200512</monisotopic_moleculate_weight>
  <iupac_name>3-methyl-6-(propan-2-ylidene)cyclohex-1-ene</iupac_name>
  <traditional_iupac>3-methyl-6-(propan-2-ylidene)cyclohex-1-ene</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC1CCC(C=C1)=C(C)C</smiles>
  <inchi>InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,9H,5,7H2,1-3H3</inchi>
  <inchikey>CIPXOBMYVWRNLL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.</description>
    <direct_parent>Menthane monoterpenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Monoterpenoids</sub_class>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Branched unsaturated hydrocarbons</alternative_parent>
      <alternative_parent>Cycloalkenes</alternative_parent>
      <alternative_parent>Monocyclic monoterpenoids</alternative_parent>
      <alternative_parent>Unsaturated aliphatic hydrocarbons</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Branched unsaturated hydrocarbon</substituent>
      <substituent>Cyclic olefin</substituent>
      <substituent>Cycloalkene</substituent>
      <substituent>Hydrocarbon</substituent>
      <substituent>Monocyclic monoterpenoid</substituent>
      <substituent>Olefin</substituent>
      <substituent>P-menthane monoterpenoid</substituent>
      <substituent>Unsaturated aliphatic hydrocarbon</substituent>
      <substituent>Unsaturated hydrocarbon</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.39e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>3-methyl-6-(propan-2-ylidene)cyclohex-1-ene</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>136.234</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>136.125200512</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1CCC(C=C1)=C(C)C</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,9H,5,7H2,1-3H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>CIPXOBMYVWRNLL-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>47.55</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>17.58</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>0</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>33423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>174412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>75162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>75163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>75164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>134748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>134749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>134750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2694669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2694670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2694671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2987447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2987448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2987449</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB0061938</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Dill</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anethum graveolens</name_scientific>
      <ncbi_taxonomy_id>40922</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
