<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:12:09 UTC</creation_date>
  <update_date>2019-11-26 03:12:30 UTC</update_date>
  <accession>FDB015965</accession>
  <name>gamma-Terpineol</name>
  <description>Isolated from carrot oils, from the cinnamon tree (Cinnamomum zeylanicum) and Scotch pine (Pinus sylvestris)

Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. gamma-Terpineol is found in many foods, some of which are common thyme, wild celery, ceylon cinnamon, and root vegetables.</description>
  <synonyms>
    <synonym>1-Methyl-4-(1-methylethylidene)cyclohexan-1-ol</synonym>
    <synonym>1-Methyl-4-(1-methylethylidene)cyclohexanol, 9CI</synonym>
    <synonym>4-Isopropylidene-1-methylcyclohexanol</synonym>
    <synonym>g-Terpineol</synonym>
    <synonym>gamma-Terpineol</synonym>
  </synonyms>
  <chemical_formula>C10H18O</chemical_formula>
  <average_molecular_weight>154.253</average_molecular_weight>
  <monisotopic_moleculate_weight>154.1357652</monisotopic_moleculate_weight>
  <iupac_name>1-methyl-4-(propan-2-ylidene)cyclohexan-1-ol</iupac_name>
  <traditional_iupac>1-methyl-4-(propan-2-ylidene)cyclohexan-1-ol</traditional_iupac>
  <cas_registry_number>586-81-2</cas_registry_number>
  <smiles>CC(C)=C1CCC(C)(O)CC1</smiles>
  <inchi>InChI=1S/C10H18O/c1-8(2)9-4-6-10(3,11)7-5-9/h11H,4-7H2,1-3H3</inchi>
  <inchikey>NNRLDGQZIVUQTE-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>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocyclic monoterpenoids</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic monoterpenoid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>P-menthane monoterpenoid</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>p-menthane monoterpenoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.68e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 68-70°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>19.04</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1-methyl-4-(propan-2-ylidene)cyclohexan-1-ol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>154.253</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>154.1357652</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(C)=C1CCC(C)(O)CC1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H18O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H18O/c1-8(2)9-4-6-10(3,11)7-5-9/h11H,4-7H2,1-3H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>NNRLDGQZIVUQTE-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>20.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>48.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>18.93</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</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::MsIr</type>
      <spectrum_id>7338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>7339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>7340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>45166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>103768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>154837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2328096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2328097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2328098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2634934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2634935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2634936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138089</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB36993</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:0x000055ce3290d8e0&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>Ceylon cinnamon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cinnamomum verum</name_scientific>
      <ncbi_taxonomy_id>128608</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cheese</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Common thyme</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Thymus vulgaris</name_scientific>
      <ncbi_taxonomy_id>49992</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Root vegetables</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Wild celery</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Apium graveolens</name_scientific>
      <ncbi_taxonomy_id>4045</ncbi_taxonomy_id>
      <average_value>9.1</average_value>
      <max_value>9.1</max_value>
      <min_value>9.1</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>lilac</name>
    </flavor>
    <flavor>
      <name>terpineol</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
