<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:06:02 UTC</creation_date>
  <update_date>2025-11-18 22:54:39 UTC</update_date>
  <accession>FDB004002</accession>
  <name>trans-p-Mentha-2,8-dien-1-ol</name>
  <description>Trans-p-mentha-2,8-dien-1-ol 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. Trans-p-mentha-2,8-dien-1-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Trans-p-mentha-2,8-dien-1-ol is a fresh and minty tasting compound found in spearmint and wild celery, which makes trans-p-mentha-2,8-dien-1-ol a potential biomarker for the consumption of these food products. </description>
  <synonyms>
    <synonym>(E)-p-2,8-Menthadien-1-ol</synonym>
    <synonym>(E)-p-menth-2,8-dien-1-ol</synonym>
    <synonym>(E)-p-mentha-2,8-dien-1-ol</synonym>
    <synonym>1R,4R-p-Mentha-2,8-dien-1-ol</synonym>
    <synonym>2-Cyclohexen-1-ol, 1-methyl-4-(1-methylethenyl)-, trans-</synonym>
    <synonym>2-Cyclohexen-1-ol, 1-methyl-4-(1-methylethenyl), cis</synonym>
    <synonym>cis-2,8-Menthadien-1-ol</synonym>
    <synonym>cis-para-Mentha-2,8-dien-1-ol</synonym>
    <synonym>E-p-Mentha-2,8-dienol</synonym>
    <synonym>Mentha-2,8-dien-1-ol, trans-para</synonym>
    <synonym>menthadien-1-ol, (E)-p-2,8</synonym>
    <synonym>p-mentha-trans-2,8-dien-1-ol</synonym>
    <synonym>trans-1-Methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol</synonym>
    <synonym>trans-1-Methyl-4-(1-methylvinyl)cyclohex-2-en-1-ol</synonym>
    <synonym>trans-2,8-Menthadien-1-ol</synonym>
    <synonym>trans-2,8-p-mentha-dien-1-ol</synonym>
    <synonym>trans-Mentha-2,8-dien-1-ol</synonym>
    <synonym>Trans-p-2,8-Menthadien-1-ol</synonym>
    <synonym>trans-p-Menth-2,8-dien-1-ol</synonym>
    <synonym>trans-p-mentha-2,8-diene-1-ol</synonym>
    <synonym>trans-para-mentha-2,8-dien-1-ol</synonym>
  </synonyms>
  <chemical_formula>C10H16O</chemical_formula>
  <average_molecular_weight>152.237</average_molecular_weight>
  <monisotopic_moleculate_weight>152.120115135</monisotopic_moleculate_weight>
  <iupac_name>(1S,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol</iupac_name>
  <traditional_iupac>(1S,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol</traditional_iupac>
  <cas_registry_number>7212-40-0</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@](C)(O)C=C1)C(C)=C</smiles>
  <inchi>InChI=1S/C10H16O/c1-8(2)9-4-6-10(3,11)7-5-9/h4,6,9,11H,1,5,7H2,2-3H3/t9-,10-/m1/s1</inchi>
  <inchikey>MKPMHJQMNACGDI-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>Tertiary 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>Tertiary alcohol</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>9.70e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.03</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>18.25</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-1.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(1S,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>152.237</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>152.120115135</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@@]1(CC[C@](C)(O)C=C1)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/c1-8(2)9-4-6-10(3,11)7-5-9/h4,6,9,11H,1,5,7H2,2-3H3/t9-,10-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>MKPMHJQMNACGDI-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>48.35</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>18.09</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::MsMs</type>
      <spectrum_id>71496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>71497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>71498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>130185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>130186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>130187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599770</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>Spearmint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha spicata</name_scientific>
      <ncbi_taxonomy_id>29719</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild celery</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Apium graveolens</name_scientific>
      <ncbi_taxonomy_id>4045</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>fresh</name>
    </flavor>
    <flavor>
      <name>mint</name>
    </flavor>
    <flavor>
      <name>minty</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
