<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:13:47 UTC</creation_date>
  <update_date>2025-11-19 02:12:10 UTC</update_date>
  <accession>FDB018550</accession>
  <name>(4S,8S)-8,9-Dihydroxy-p-menth-1(6)-en-2-one</name>
  <description>Constituent of fruit of Carum carvi (caraway). (4S,8S)-8,9-Dihydroxy-p-menth-1(6)-en-2-one is found in herbs and spices.</description>
  <synonyms>
  </synonyms>
  <chemical_formula>C10H16O3</chemical_formula>
  <average_molecular_weight>184.235</average_molecular_weight>
  <monisotopic_moleculate_weight>184.109944375</monisotopic_moleculate_weight>
  <iupac_name>5-(1,2-dihydroxypropan-2-yl)-2-methylcyclohex-2-en-1-one</iupac_name>
  <traditional_iupac>5-(1,2-dihydroxypropan-2-yl)-2-methylcyclohex-2-en-1-one</traditional_iupac>
  <cas_registry_number>402593-42-4</cas_registry_number>
  <smiles>CC1=CCC(CC1=O)C(C)(O)CO</smiles>
  <inchi>InChI=1S/C10H16O3/c1-7-3-4-8(5-9(7)12)10(2,13)6-11/h3,8,11,13H,4-6H2,1-2H3</inchi>
  <inchikey>AOKPDATZUBLDMG-UHFFFAOYSA-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>1,2-diols</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocyclic monoterpenoids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocyclic monoterpenoid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>P-menthane monoterpenoid</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.97e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>13.85</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5-(1,2-dihydroxypropan-2-yl)-2-methylcyclohex-2-en-1-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>184.235</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>184.109944375</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1=CCC(CC1=O)C(C)(O)CO</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H16O3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H16O3/c1-7-3-4-8(5-9(7)12)10(2,13)6-11/h3,8,11,13H,4-6H2,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>AOKPDATZUBLDMG-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>57.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>50.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>20.13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</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>5717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>46231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>162335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2840265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2840266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2840267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2869383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2869384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2869385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>30881</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB39052</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce3245e8a8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
