<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:08:07 UTC</creation_date>
  <update_date>2025-11-18 23:11:06 UTC</update_date>
  <accession>FDB008523</accession>
  <name>Nerylacetone</name>
  <description>Geranylacetone or (5Z)-6,10-Dimethylundeca-5,9-dien-2-one, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Geranylacetone is neutral compound with . a citrus, earthy, and fatty taste. Geranylacetone is found in highest concentrations in wild carrots, carrots, and tortilla and in lower concentrations in corns. Geranylacetone has also been detected in figs, lemon grass, garden tomato (var.), tortilla chips, and papaya. This could make geranylacetone a potential biomarker for the consumption of these foods. Geranylacetone is an industrial intermediate in the vitamin E synthesis (https://doi.org/10.1002%2F14356007.a26_205).</description>
  <synonyms>
    <synonym>(5Z)-6,10-Dimethyl-5,9-undecadien-2-one</synonym>
    <synonym>Allocor</synonym>
    <synonym>Cedilanid</synonym>
    <synonym>Ceglunat</synonym>
    <synonym>Ceglunate</synonym>
    <synonym>Celadigal</synonym>
    <synonym>Celanid</synonym>
    <synonym>Celanide</synonym>
    <synonym>Celanidum</synonym>
    <synonym>Cetosanol</synonym>
    <synonym>cis-Geranyl acetone</synonym>
    <synonym>Cis-geranylacetone</synonym>
    <synonym>Desacetyllanatoside</synonym>
    <synonym>Digilanid c</synonym>
    <synonym>Digilanide c</synonym>
    <synonym>Glycoside obtained from the leaves of digitalis lanata ehrh</synonym>
    <synonym>Isolanid</synonym>
    <synonym>Isolanide</synonym>
    <synonym>Lanatigen c</synonym>
    <synonym>Lanatosid c</synonym>
    <synonym>Lanatoside</synonym>
    <synonym>Lanatoside a</synonym>
    <synonym>Lanatoside c</synonym>
    <synonym>Lanatoside c [inn:ban:DCF:jan]</synonym>
    <synonym>Lanatosido c</synonym>
    <synonym>Lanatosidum c</synonym>
    <synonym>Lanimerck</synonym>
    <synonym>Lanocide-c</synonym>
    <synonym>Nerylacetone</synonym>
  </synonyms>
  <chemical_formula>C13H22O</chemical_formula>
  <average_molecular_weight>194.3132</average_molecular_weight>
  <monisotopic_moleculate_weight>194.167065326</monisotopic_moleculate_weight>
  <iupac_name>(5Z)-6,10-dimethylundeca-5,9-dien-2-one</iupac_name>
  <traditional_iupac>(5Z)-6,10-dimethylundeca-5,9-dien-2-one</traditional_iupac>
  <cas_registry_number>3879-26-3</cas_registry_number>
  <smiles>CC(C)=CCC\C(C)=C/CCC(C)=O</smiles>
  <inchi>InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9-</inchi>
  <inchikey>HNZUNIKWNYHEJJ-XFXZXTDPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.</description>
    <direct_parent>Acyclic 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 acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyclic monoterpenoid</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Hydrocarbons</external_descriptor>
      <external_descriptor>monoterpene ketone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>9.42e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.68</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>19.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-7.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(5Z)-6,10-dimethylundeca-5,9-dien-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>194.3132</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>194.167065326</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(C)=CCC\C(C)=C/CCC(C)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C13H22O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>HNZUNIKWNYHEJJ-XFXZXTDPSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>17.07</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>63.83</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>24.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>6</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::MsIr</type>
      <spectrum_id>4943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>4944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>168056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>126486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>126487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>126488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2785831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2785832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2785833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2922550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2922551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2922552</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB0031846</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>Lemon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus limon</name_scientific>
      <ncbi_taxonomy_id>2708</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet basil</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ocimum basilicum</name_scientific>
      <ncbi_taxonomy_id>39350</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>fatty</name>
    </flavor>
    <flavor>
      <name>metallic</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
