<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:11:05 UTC</creation_date>
  <update_date>2025-11-19 00:43:58 UTC</update_date>
  <accession>FDB014115</accession>
  <name>(±)-Limonene</name>
  <description>Constituent of many essential oils. (±)-Limonene is found in many foods, some of which are common oregano, nutmeg, herbs and spices, and summer savory.</description>
  <synonyms>
    <synonym>(+-)-(RS)-Limonene</synonym>
    <synonym>(+-)-Dipentene</synonym>
    <synonym>(+-)-Limonene</synonym>
    <synonym>(+/-)-P-mentha-1,8-diene homopolymer</synonym>
    <synonym>(±)-Dipentene</synonym>
    <synonym>(±)-Limonene</synonym>
    <synonym>(R/S)-Limonene</synonym>
    <synonym>Dipentene</synonym>
    <synonym>DL-Limonene</synonym>
  </synonyms>
  <chemical_formula>C10H16</chemical_formula>
  <average_molecular_weight>136.238</average_molecular_weight>
  <monisotopic_moleculate_weight>136.125200515</monisotopic_moleculate_weight>
  <iupac_name>1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene</iupac_name>
  <traditional_iupac>limonene, (+)-</traditional_iupac>
  <cas_registry_number>9003-73-0</cas_registry_number>
  <smiles>CC(=C)C1CCC(C)=CC1</smiles>
  <inchi>InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3</inchi>
  <inchikey>XMGQYMWWDOXHJM-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_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>Terpenoids</external_descriptor>
      <external_descriptor>a limonene</external_descriptor>
      <external_descriptor>monoterpene</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.57e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>&lt; 25 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.22</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>136.238</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>136.125200515</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(=C)C1CCC(C)=CC1</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/h4,10H,1,5-7H2,2-3H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>XMGQYMWWDOXHJM-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>46.48</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>17.55</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</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::EiMs</type>
      <spectrum_id>1903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>154389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>135963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>135964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>135965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2227987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3060091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3060092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3060093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3109701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3109702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3109703</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB32473</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:0x000055ce32cb3148&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Carrot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Daucus carota ssp. sativus</name_scientific>
      <ncbi_taxonomy_id>79200</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common oregano</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Origanum vulgare</name_scientific>
      <ncbi_taxonomy_id>39352</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Coriander</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Coriandrum sativum</name_scientific>
      <ncbi_taxonomy_id>4047</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cumin</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cuminum cyminum</name_scientific>
      <ncbi_taxonomy_id>52462</ncbi_taxonomy_id>
    </food>
    <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>
    <food>
      <name>Fennel</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Foeniculum vulgare</name_scientific>
      <ncbi_taxonomy_id>48038</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>Lemon grass</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cymbopogon citratus</name_scientific>
      <ncbi_taxonomy_id>66014</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mango</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mangifera indica</name_scientific>
      <ncbi_taxonomy_id>29780</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Nutmeg</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Myristica fragrans</name_scientific>
      <ncbi_taxonomy_id>51089</ncbi_taxonomy_id>
      <average_value>800.0</average_value>
      <max_value>800.0</max_value>
      <min_value>800.0</min_value>
      <unit>mg/100 g</unit>
    </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>
    <food>
      <name>Peppermint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha X piperita</name_scientific>
      <ncbi_taxonomy_id>34256</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pine nut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pinus</name_scientific>
      <ncbi_taxonomy_id>3337</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rosemary</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rosmarinus officinalis</name_scientific>
      <ncbi_taxonomy_id>39367</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Star anise</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Illicium verum</name_scientific>
      <ncbi_taxonomy_id>124778</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Summer savory</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Satureja hortensis</name_scientific>
      <ncbi_taxonomy_id>49987</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild carrot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Daucus carota</name_scientific>
      <ncbi_taxonomy_id>4039</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Winter savory</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Satureja montana</name_scientific>
      <ncbi_taxonomy_id>49988</ncbi_taxonomy_id>
      <average_value>171.5</average_value>
      <max_value>171.5</max_value>
      <min_value>171.5</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>camphor</name>
    </flavor>
    <flavor>
      <name>citrus</name>
    </flavor>
    <flavor>
      <name>herbal</name>
    </flavor>
    <flavor>
      <name>terpene</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Allergenic</name>
      <id>43</id>
      <definition>A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.</definition>
    </health_effect>
    <health_effect>
      <name>Anti bacterial</name>
      <id>145</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-viral</name>
      <id>689</id>
      <definition>A substance that destroys or inhibits replication of viruses.</definition>
    </health_effect>
    <health_effect>
      <name>Expectorant</name>
      <id>925</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Irritant</name>
      <id>1055</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Pesticide</name>
      <id>1210</id>
      <definition>Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.</definition>
    </health_effect>
    <health_effect>
      <name>Sedative</name>
      <id>1311</id>
      <definition>A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.</definition>
    </health_effect>
  </health_effects>
</compound>
