<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:37 UTC</creation_date>
  <update_date>2025-11-18 22:46:32 UTC</update_date>
  <accession>FDB003013</accession>
  <name>2-Dodecenal</name>
  <description>Cilantro is a delightful spice added to make tacos and guacamole delicious and enliven the taste and aroma of many Spanish/Mexican foods. However for some people cilantro tastes and smells like soap. A number of famous chefs abhor(ed) cilantro, including Julia Child, Ina Garten (aka Barefoot Contessa) and Top Chef Fabio Viviani. It turns out that the compound that gives Cilantro the pleasant citrus taste/smell is 2-dodecenal. If you have a mutation in an olafactory receptor, it can't distinguish between 2-dodecenal and 1-dodecenal. 1-dodecenal tastes and smells soapy. So for people who hate cilantro, 2-dodecenal looks and tastes like 1-dodecenal. [DW]. 2-Dodecenal is found in lemon.</description>
  <synonyms>
    <synonym>&amp;beta;-octyl acrolein</synonym>
    <synonym>Beta-octyl acrolein</synonym>
    <synonym>FEMA 2402</synonym>
  </synonyms>
  <chemical_formula>C12H22O</chemical_formula>
  <average_molecular_weight>182.3025</average_molecular_weight>
  <monisotopic_moleculate_weight>182.167065326</monisotopic_moleculate_weight>
  <iupac_name>(2E)-dodec-2-enal</iupac_name>
  <traditional_iupac>2-dodecenal</traditional_iupac>
  <cas_registry_number>4826-62-4</cas_registry_number>
  <smiles>CCCCCCCCC\C=C\C=O</smiles>
  <inchi>InChI=1S/C12H22O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h10-12H,2-9H2,1H3/b11-10+</inchi>
  <inchikey>SSNZFFBDIMUILS-ZHACJKMWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.</description>
    <direct_parent>Medium-chain aldehydes</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 acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Enals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated aldehyde</substituent>
      <substituent>Enal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain aldehyde</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Fatty aldehydes</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.79e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2E)-dodec-2-enal</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>182.3025</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>182.167065326</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CCCCCCCCC\C=C\C=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C12H22O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C12H22O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h10-12H,2-9H2,1H3/b11-10+</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>SSNZFFBDIMUILS-ZHACJKMWSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>17.07</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>58.85</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>24.03</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>9</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>165391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>4070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>4071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>117798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>117799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>117800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2748352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2748353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2748354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2934096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2934097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2934098</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB0031020</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>Lemon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus limon</name_scientific>
      <ncbi_taxonomy_id>2708</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>citrus</name>
    </flavor>
    <flavor>
      <name>fat</name>
    </flavor>
    <flavor>
      <name>fruity</name>
    </flavor>
    <flavor>
      <name>green</name>
    </flavor>
    <flavor>
      <name>herbal</name>
    </flavor>
    <flavor>
      <name>mandarin</name>
    </flavor>
    <flavor>
      <name>orange</name>
    </flavor>
    <flavor>
      <name>sweet</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
