<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:58 UTC</creation_date>
  <update_date>2025-11-18 22:54:08 UTC</update_date>
  <accession>FDB003846</accession>
  <name>D-(+)-dihydrocarvone</name>
  <description>(1r,4r)-dihydrocarvone, also known as (2r,5r)-2-methyl-5-isopropenylcyclohexanone, 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. Thus, (1r,4r)-dihydrocarvone is considered to be an isoprenoid lipid molecule (1r,4r)-dihydrocarvone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (1r,4r)-dihydrocarvone is a herbal and minty tasting compound found in spearmint, which makes (1r,4r)-dihydrocarvone a potential biomarker for the consumption of this food product. </description>
  <synonyms>
  </synonyms>
  <chemical_formula>C10H16O</chemical_formula>
  <average_molecular_weight>152.2334</average_molecular_weight>
  <monisotopic_moleculate_weight>152.120115134</monisotopic_moleculate_weight>
  <iupac_name>(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one</iupac_name>
  <traditional_iupac>(+)-dihydrocarvone</traditional_iupac>
  <cas_registry_number>5524-05-0</cas_registry_number>
  <smiles>C[C@@H]1CC[C@H](CC1=O)C(C)=C</smiles>
  <inchi>InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3/t8-,9-/m1/s1</inchi>
  <inchikey>AZOCECCLWFDTAP-RKDXNWHRSA-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 ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocyclic monoterpenoids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocyclic monoterpenoid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>P-menthane monoterpenoid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>dihydrocarvone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.61e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-7.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>152.2334</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>152.120115134</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>C[C@@H]1CC[C@H](CC1=O)C(C)=C</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H16O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3/t8-,9-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>AZOCECCLWFDTAP-RKDXNWHRSA-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>46.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>18.26</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</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::EiMs</type>
      <spectrum_id>1680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>99693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>99694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>99695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>164868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>164869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>164870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599509</spectrum_id>
    </spectrum>
  </spectra>
  <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>
      <average_value>104.65</average_value>
      <max_value>104.65</max_value>
      <min_value>104.65</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
