<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:07:55 UTC</creation_date>
  <update_date>2025-11-18 23:06:54 UTC</update_date>
  <accession>FDB008103</accession>
  <name>2-Hydroxy-3-methyl-2-cyclopenten-1-one</name>
  <description>2-hydroxy-3-methyl-2-cyclopenten-1-one, also known as cyclotene, is a member of the class of compounds known as cyclic ketones. Cyclic ketones are organic compounds containing a ketone that is conjugated to a cyclic moiety. 2-hydroxy-3-methyl-2-cyclopenten-1-one is soluble (in water) and a very weakly acidic compound (based on its pKa). 2-hydroxy-3-methyl-2-cyclopenten-1-one is a caramel, maple, and maple syrup tasting compound and can be found in a number of food items such as pepper (c. annuum), green bell pepper, red bell pepper, and yellow bell pepper, which makes 2-hydroxy-3-methyl-2-cyclopenten-1-one a potential biomarker for the consumption of these food products. </description>
  <synonyms>
    <synonym>2-Cyclopenten-1-one, 2-hydroxy-3-methyl-</synonym>
    <synonym>2-Hydroxy-1-methylcyclopenten-3-one</synonym>
    <synonym>2-Hydroxy-3-methyl-2-cyclopenten-1-one</synonym>
    <synonym>2-Hydroxy-3-methyl-2-cyclopenten-1-one (Cyclotene)</synonym>
    <synonym>2-hydroxy-3-methyl-2-cyclopenten1-one (cycloten)</synonym>
    <synonym>2-Hydroxy-3-methyl-2-cyclopentene-1-one(cyclotene)</synonym>
    <synonym>2-hydroxy-3-methyl-2-cyclopentenone</synonym>
    <synonym>2-Hydroxy-3-methylcyclopent-2-en-1-one</synonym>
    <synonym>2-Hydroxy-3-methylcyclopent-2-enone</synonym>
    <synonym>2-Hydroxy-3-methylcyclopentenone</synonym>
    <synonym>3-Methyl-1,2-cyclopentanedione (cyclotene)</synonym>
    <synonym>3-Methyl-2-cyclopentene-2-ol-1-one</synonym>
    <synonym>3-Methyl-2-hydroxy-2-cyclopentenone</synonym>
    <synonym>3-Methylcyclopent-2-en-2-ol-1-one</synonym>
    <synonym>3-Methylcyclopentane-1,2-dione hydrate</synonym>
    <synonym>Corylon</synonym>
    <synonym>Cycloten</synonym>
    <synonym>Cyclotene (ordorant)</synonym>
    <synonym>Maple lactone</synonym>
  </synonyms>
  <chemical_formula>C6H8O2</chemical_formula>
  <average_molecular_weight>112.1265</average_molecular_weight>
  <monisotopic_moleculate_weight>112.0524295</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-3-methylcyclopent-2-en-1-one</iupac_name>
  <traditional_iupac>cyclotene</traditional_iupac>
  <cas_registry_number>80-71-7</cas_registry_number>
  <smiles>CC1=C(O)C(=O)CC1</smiles>
  <inchi>InChI=1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3</inchi>
  <inchikey>CFAKWWQIUFSQFU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.</description>
    <direct_parent>Cyclic ketones</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Enols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Enol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.98e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>106.5 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.77</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.34</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-hydroxy-3-methylcyclopent-2-en-1-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>112.1265</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>112.0524295</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1=C(O)C(=O)CC1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C6H8O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>CFAKWWQIUFSQFU-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>37.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>30.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>11.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</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>2952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>53934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>53935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>53936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3604685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3604686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3604687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3604688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3604689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3604690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336837</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>Green bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Orange bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Red bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Yellow bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>caramel</name>
    </flavor>
    <flavor>
      <name>maple</name>
    </flavor>
    <flavor>
      <name>maple syrup</name>
    </flavor>
    <flavor>
      <name>smoky</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
