<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:11:32 UTC</creation_date>
  <update_date>2019-11-26 03:10:56 UTC</update_date>
  <accession>FDB014918</accession>
  <name>(-)-cis-Carveol</name>
  <description>Constituent of Valencia orange oil (Citrus sinensis). Flavouring agent. (-)-cis-Carveol is found in citrus.</description>
  <synonyms>
    <synonym>(-)-(4R,6R)-cis-carveol</synonym>
    <synonym>(-)-cis-Carveol</synonym>
    <synonym>(-)-cis-P-Mentha-1,8-dien-6-ol</synonym>
    <synonym>(1R-cis)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-ol</synonym>
    <synonym>(1R-cis)-2-Methyl-5-isopropenyl-2-cyclohexen-1-ol</synonym>
    <synonym>(1R,5R)-(-)-cis-Carveol</synonym>
    <synonym>(1R)-cis-Carveol</synonym>
    <synonym>(4R,6R)-p-mentha-1,8-dien-6-ol</synonym>
    <synonym>2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, (1R-cis)-</synonym>
    <synonym>2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, (1R,5R)-</synonym>
    <synonym>2-Methyl-5-(1-methylethenyl)-(1R-cis)-2-cyclohexen-1-ol</synonym>
    <synonym>2-Methyl-5-(1-methylethenyl)-(1R,5R)-2-cyclohexen-1-ol</synonym>
    <synonym>Carveol, cis-(-)-</synonym>
    <synonym>Cis-(-)-carveol</synonym>
    <synonym>p-Mentha-1,8-dien-6-ol; (-)-cis-form</synonym>
  </synonyms>
  <chemical_formula>C10H16O</chemical_formula>
  <average_molecular_weight>152.2334</average_molecular_weight>
  <monisotopic_moleculate_weight>152.120115134</monisotopic_moleculate_weight>
  <iupac_name>(1R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol</iupac_name>
  <traditional_iupac>(-)-cis-carveol</traditional_iupac>
  <cas_registry_number>2102-59-2</cas_registry_number>
  <smiles>CC(=C)[C@@H]1CC=C(C)[C@H](O)C1</smiles>
  <inchi>InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3/t9-,10-/m1/s1</inchi>
  <inchikey>BAVONGHXFVOKBV-NXEZZACHSA-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>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocyclic monoterpenoids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic monoterpenoid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>P-menthane monoterpenoid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Cyclic monoterpenes</external_descriptor>
      <external_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>carveol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Liquid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.82e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 24-25°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>18.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-1.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(1R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol</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>CC(=C)[C@@H]1CC=C(C)[C@H](O)C1</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/h4,9-11H,1,5-6H2,2-3H3/t9-,10-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>BAVONGHXFVOKBV-NXEZZACHSA-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</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>18.39</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>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::EiMs</type>
      <spectrum_id>1751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>44716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>155898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>63618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>63619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>63620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>120588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>120589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>120590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2834289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2834290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2834291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2871866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2871867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2871868</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB36082</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>227</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce331e7330&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Citrus</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>spearmint</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
