<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:57 UTC</creation_date>
  <update_date>2019-11-26 03:09:11 UTC</update_date>
  <accession>FDB013861</accession>
  <name>(S)-Limonene</name>
  <description>Constituent of pine needle oiland is) also present in ginger, nutmeg, pepper, mace, coriander and other herbs and spices. (S)-Limonene is found in many foods, some of which are fennel, caraway, cardamom, and herbs and spices.</description>
  <synonyms>
    <synonym>(-)-(4S)-Limonene</synonym>
    <synonym>(-)-(s)-limonene</synonym>
    <synonym>(-)-carvene</synonym>
    <synonym>(-)-Limonene</synonym>
    <synonym>(-)-p-Mentha-1,8-diene</synonym>
    <synonym>(4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene</synonym>
    <synonym>(4S)-1-methyl-4-isopropenylcyclohex-1-ene</synonym>
    <synonym>(4S)-4-isopropenyl-1-methylcyclohexene</synonym>
    <synonym>(4S)-limonene</synonym>
    <synonym>(s)-(-)-limonene</synonym>
    <synonym>(S)-(-)-p-mentha-1,8-diene</synonym>
    <synonym>(S)-1-methyl-4-(1-methylethenyl)cyclohexene</synonym>
    <synonym>(S)-4-Isopropenyl-1-methyl cyclohexene</synonym>
    <synonym>(S)-p-mentha-1,8-diene</synonym>
    <synonym>4-Isopropenyl-1-methyl-1-cyclohexene</synonym>
    <synonym>4alphaH-p-mentha-1,8-diene</synonym>
    <synonym>L-limonen</synonym>
    <synonym>L-limonene</synonym>
    <synonym>Limonene</synonym>
    <synonym>p-Mentha-1,8-diene, (S)-(-)-</synonym>
    <synonym>S-(-)-limonene</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>(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene</iupac_name>
  <traditional_iupac>α-limonene</traditional_iupac>
  <cas_registry_number>5989-54-8</cas_registry_number>
  <smiles>CC(=C)[C@@H]1CCC(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/t10-/m0/s1</inchi>
  <inchikey>XMGQYMWWDOXHJM-JTQLQIEISA-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>Cyclic monoterpenes</external_descriptor>
      <external_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>limonene</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Liquid</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>-90 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.22</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(4R)-1-methyl-4-(prop-1-en-2-yl)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>CC(=C)[C@@H]1CCC(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/t10-/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>XMGQYMWWDOXHJM-JTQLQIEISA-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::NmrTwoD</type>
      <spectrum_id>1931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>103753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>167667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3053483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3053484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3053485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3116352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3116353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3116354</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB03375</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>15383</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31731978&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31731770&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317315b8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317312e8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31731090&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31730eb0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31730ca8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31730a28&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Caraway</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Carum carvi</name_scientific>
      <ncbi_taxonomy_id>48032</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cardamom</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Elettaria cardamomum</name_scientific>
      <ncbi_taxonomy_id>105181</ncbi_taxonomy_id>
    </food>
    <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>Cherry tomato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum lycopersicum var. cerasiforme</name_scientific>
      <ncbi_taxonomy_id>195583</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common sage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Salvia officinalis</name_scientific>
      <ncbi_taxonomy_id>38868</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cornmint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha arvensis</name_scientific>
      <ncbi_taxonomy_id>292239</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cottonseed</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Gossypium</name_scientific>
      <ncbi_taxonomy_id>3633</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>Garden tomato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum lycopersicum</name_scientific>
      <ncbi_taxonomy_id>4081</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garden tomato (var.)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum lycopersicum var. lycopersicum</name_scientific>
      <ncbi_taxonomy_id>397755</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>Milk (Cow)</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Orange mint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha aquatica</name_scientific>
      <ncbi_taxonomy_id>190902</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>
    <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>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>
    <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>
  </foods>
  <flavors>
    <flavor>
      <name>camphoraceous</name>
    </flavor>
    <flavor>
      <name>herbal</name>
    </flavor>
    <flavor>
      <name>peppery</name>
    </flavor>
    <flavor>
      <name>pine</name>
    </flavor>
    <flavor>
      <name>terpene</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti acetylcholinesterase</name>
      <id>76</id>
      <definition>An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.</definition>
    </health_effect>
  </health_effects>
</compound>
