<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 22:33:57 UTC</creation_date>
  <update_date>2026-03-31 21:37:44 UTC</update_date>
  <accession/>
  <common_name>trans-Caryophyllene oxide</common_name>
  <class>SmallMolecule</class>
  <description>trans-Caryophyllene oxide (C15H24O) is an organic compound with an average molecular weight of 220.35 g/mol. trans-Caryophyllene oxide belongs to the sesquiterpenoids, a subclass of prenol lipids within the organic compounds.

This compound is identified in or released from 19 recorded sources across several categories. Within household cleaning and consumer products, it is found in bleaching agents, cigar cigarettes, non electric simulated smoking devices, pipe accessories, and perfumes within detergents and soaps, among four additional sources. In the context of food, food processing and cookware, it is associated with the treatment of hops, the preparation of vinegar, the preparation of wort, and the preparation of wine or sparkling wine, as well as fermentation processes for beer. Additionally, the compound is present in electrical and electronic equipment, specifically in discharge lamps, electrically stimulated smoking devices, hybrid capacitors, and fixed capacitors and their manufacture. It is also recorded in building and construction materials, specifically fencing.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>Caryophyllene beta-oxide</synonym>
    <synonym>Epoxycaryophyllene</synonym>
  </synonyms>
  <chemical_formula>C15H24O</chemical_formula>
  <average_molecular_weight>220.3505</average_molecular_weight>
  <monisotopic_moleculate_weight>220.18271539</monisotopic_moleculate_weight>
  <iupac_name>4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecane</iupac_name>
  <traditional_iupac>caryophyllene oxide</traditional_iupac>
  <cas_registry_number>17627-43-9</cas_registry_number>
  <smiles>CC12CCC3C(CC3(C)C)C(=C)CCC1O2</smiles>
  <inchi>InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3</inchi>
  <inchikey>NVEQFIOZRFFVFW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Sesquiterpenoids</sub_class>
    <direct_parent>Sesquiterpenoids</direct_parent>
    <alternate_parents>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Epoxides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Caryophyllane sesquiterpenoid</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxirane</substituent>
      <substituent>Sesquiterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.96e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecane</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>220.3505</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>220.18271539</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC12CCC3C(CC3(C)C)C(=C)CCC1O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H24O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NVEQFIOZRFFVFW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>12.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>66.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.42</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>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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bf17b0a00&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id/>
  <hmdb_id/>
  <pubchem_compound_id>14350</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>13711</chemspider_id>
  <kegg_id/>
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  <biocyc_id/>
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  <wikipidia/>
  <general_references/>
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</compound>
