<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-06-03 09:43:01 UTC</creation_date>
  <update_date>2026-05-14 19:41:03 UTC</update_date>
  <accession/>
  <common_name>DL-menthol</common_name>
  <class>SmallMolecule</class>
  <description>DL-menthol (C10H20O) is a compound with an average molecular weight of 156.27 g/mol. DL-menthol belongs to the monoterpenoids, a subclass of prenol lipids within the organic compounds. Industrially, it is utilized as a fragrance, an additive (PMC9357114), and as a flavouring and nutrient (PMC12159706, PMC8776015). Biologically, it acts as an antioxidant (PMC12159706, PMC8776015) and an analgesic (PMC7609673). Due to its analgesic properties, it is used as a treatment for arthritis (PMC7609673).

The compound is found in or released from 37 recorded sources. These include drinking water and water supply (Drinking water), building and construction (Fencing, Stairs And Ramps), and household items such as medals, badges, and watch chains. It is also associated with food, food processing, and cookware, specifically including food contact materials, food preservation, the preparation of vinegar, molasses and treatment of molasses, and fermentation processes for beer. Additionally, it is found in electrical and electronic equipment, including electrodes, fixed capacitors and their manufacture, electric switches, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. Household cleaning and consumer products such as bleaching agents, ash trays, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and 8 more are also recorded sources. Recorded exposure routes include touch, oral, and inhalation, with literature support provided for inhalation (PMC9498982).</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C10H20O</chemical_formula>
  <average_molecular_weight>156.2652</average_molecular_weight>
  <monisotopic_moleculate_weight>156.151415262</monisotopic_moleculate_weight>
  <iupac_name>5-methyl-2-(propan-2-yl)cyclohexan-1-ol</iupac_name>
  <traditional_iupac>menthol natural</traditional_iupac>
  <cas_registry_number>89-78-1</cas_registry_number>
  <smiles>CC(C)C1CCC(C)CC1O</smiles>
  <inchi>InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3</inchi>
  <inchikey>NOOLISFMXDJSKH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Monoterpenoids</sub_class>
    <direct_parent>Menthane monoterpenoids</direct_parent>
    <alternate_parents>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocyclic monoterpenoids</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclohexanol</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>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>a monoterpenol</descriptor>
      <descriptor>p-menthane monoterpenoid</descriptor>
      <descriptor>secondary alcohol</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2.66</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.58e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-methyl-2-(propan-2-yl)cyclohexan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>156.2652</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>156.151415262</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C1CCC(C)CC1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H20O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NOOLISFMXDJSKH-UHFFFAOYSA-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>47.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.69</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f726c486058&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB14123</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>1254</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>15803</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
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  <stitch_id/>
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  <pdb_id/>
  <wikipidia/>
  <general_references/>
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</compound>
