<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:08:43 UTC</creation_date>
  <update_date>2025-11-18 23:17:10 UTC</update_date>
  <accession>FDB009636</accession>
  <name>Isoborneol</name>
  <description>(-)-Isoborneol, also known as borneol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Borneol can be synthesized by reducing camphor by the Meerwein‚ÄìPonndorf‚ÄìVerley reaction, a reversible, inexpensive process. The isomer isoborneol can be produced in the kinetically controlled reduction of camphor with sodium borohydride, which is fast and irreversible. (-)-Isoborneol is neutral compound, a white crystalline solid with a balsamic camphoreous herbal woody odor and camphoreous minty herbal earthy woody flavor ( http://www.thegoodscentscompany.com/data/rw1002092.html#toorgano). Borneol or isoborneol is a naturally occurring organic compound found in the essential oil of many plants such as camphorweed, mugwort, beautyberry, Ngai camphor, aromatic ginger .</description>
  <synonyms>
    <synonym>(+/-)-isoborneol</synonym>
    <synonym>(±)-Isoborneol</synonym>
    <synonym>Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, exo-</synonym>
    <synonym>Borneol, exo-</synonym>
    <synonym>DL-isoborneol</synonym>
    <synonym>exo-1,7,7-Trimethylbicyclo(2.2.1)-2-heptanol</synonym>
    <synonym>exo-1,7,7-Trimethylbicyclo(2.2.1)heptan-2-ol</synonym>
    <synonym>exo-2-Bornanol</synonym>
    <synonym>exo-2-Camphanol</synonym>
    <synonym>exo-2-Hydroxy-1,7,7-trimethylnorbornane</synonym>
    <synonym>Exoborneol</synonym>
    <synonym>ISOBORNEOL</synonym>
    <synonym>Isoborneol, DL-</synonym>
    <synonym>Isobornyl alcohol</synonym>
  </synonyms>
  <chemical_formula>C10H18O</chemical_formula>
  <average_molecular_weight>154.2493</average_molecular_weight>
  <monisotopic_moleculate_weight>154.135765198</monisotopic_moleculate_weight>
  <iupac_name>(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol</iupac_name>
  <traditional_iupac>(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol</traditional_iupac>
  <cas_registry_number>124-76-5</cas_registry_number>
  <smiles>CC1(C)[C@@H]2CC[C@@]1(C)[C@H](O)C2</smiles>
  <inchi>InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1</inchi>
  <inchikey>DTGKSKDOIYIVQL-MRTMQBJTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.</description>
    <direct_parent>Bicyclic 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 homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Bicyclic monoterpenoid</substituent>
      <substituent>Bornane monoterpenoid</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.05e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 212° (sealed tube)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.99</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>-0.78</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>154.2493</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>154.135765198</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1(C)[C@@H]2CC[C@@]1(C)[C@H](O)C2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H18O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>DTGKSKDOIYIVQL-MRTMQBJTSA-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>45.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>18.43</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::CMs</type>
      <spectrum_id>11026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>44578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>103764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>162463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>90303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>90304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>90305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2809595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2809596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2809597</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB0035815</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>Blackberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rubus</name_scientific>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Common oregano</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Origanum vulgare</name_scientific>
      <ncbi_taxonomy_id>39352</ncbi_taxonomy_id>
      <average_value>0.25</average_value>
      <max_value>0.25</max_value>
      <min_value>0.25</min_value>
      <unit>mg/100 g</unit>
    </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>
      <average_value>39.2</average_value>
      <max_value>39.2</max_value>
      <min_value>39.2</min_value>
      <unit>mg/100 g</unit>
    </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>Evergreen blackberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rubus laciniatus</name_scientific>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Ginger</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zingiber officinale</name_scientific>
      <ncbi_taxonomy_id>94328</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rosemary</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rosmarinus officinalis</name_scientific>
      <ncbi_taxonomy_id>39367</ncbi_taxonomy_id>
      <average_value>5.1</average_value>
      <max_value>5.1</max_value>
      <min_value>5.1</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Turmeric</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Curcuma longa</name_scientific>
      <ncbi_taxonomy_id>136217</ncbi_taxonomy_id>
      <average_value>20.0</average_value>
      <max_value>20.0</max_value>
      <min_value>20.0</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>balsam</name>
    </flavor>
    <flavor>
      <name>camphor</name>
    </flavor>
    <flavor>
      <name>herbal</name>
    </flavor>
    <flavor>
      <name>must</name>
    </flavor>
    <flavor>
      <name>woody</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti-herpetic</name>
      <id>329</id>
      <definition>A substance that destroys or inhibits replication of viruses.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-viral</name>
      <id>689</id>
      <definition>A substance that destroys or inhibits replication of viruses.</definition>
    </health_effect>
    <health_effect>
      <name>Insectifuge</name>
      <id>1041</id>
      <definition>Strictly, a substance intended to kill members of the class Insecta.  In common usage, any substance used for preventing, destroying, repelling or controlling insects.</definition>
    </health_effect>
    <health_effect>
      <name>Motor stimulant</name>
      <id>1119</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Nematicide</name>
      <id>1141</id>
      <definition>A substance used to destroy pests of the phylum Nematoda (roundworms).</definition>
    </health_effect>
    <health_effect>
      <name>Pesticide</name>
      <id>1210</id>
      <definition>Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.</definition>
    </health_effect>
    <health_effect>
      <name>Sedative</name>
      <id>1311</id>
      <definition>A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.</definition>
    </health_effect>
  </health_effects>
</compound>
