<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:08:24 UTC</creation_date>
  <update_date>2025-11-18 23:15:05 UTC</update_date>
  <accession>FDB009075</accession>
  <name>Caprolactam</name>
  <description>Caprolactam, also known as aminocaproic lactam or hexahydro-2h-azepin-2-one, is a member of the class of compounds known as caprolactams. Caprolactams are cyclic amides of caproic acid. Caproic acid is the carboxylic acid derived from hexane with the general formula C5H11COOH. Caprolactam is soluble (in water) and a very weakly acidic compound (based on its pKa). Caprolactam is an amine, bitter, and spicy tasting compound found in sunflower, which makes caprolactam a potential biomarker for the consumption of this food product. Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH. This colourless solid is a lactam (a cyclic amide) of caproic acid. Global demand for this compound is approximately 5 million tons per year, and the vast majority is used to make Nylon 6 filament, fiber, and plastics .</description>
  <synonyms>
    <synonym>1-Aza-2-cycloheptanone</synonym>
    <synonym>1,6-Hexalactam</synonym>
    <synonym>1,6-Hexolactam</synonym>
    <synonym>2-Azacycloheptanone</synonym>
    <synonym>2-Azepanone</synonym>
    <synonym>2-Ketohexamethyleneimine</synonym>
    <synonym>2-Ketohexamethylenimine</synonym>
    <synonym>2-Oxohexamethyleneimine</synonym>
    <synonym>2-Oxohexamethylenimine</synonym>
    <synonym>2-Perhydroazepinone</synonym>
    <synonym>2H-Azepin-2-one, hexahydro-</synonym>
    <synonym>2H-Azepin-7-one, hexahydro-</synonym>
    <synonym>6-amino-hexanoic acid lactam</synonym>
    <synonym>6-Aminocaproic acid lactam</synonym>
    <synonym>6-Aminohexanoic acid cyclic lactam</synonym>
    <synonym>6-Aminohexanoic acid lactam</synonym>
    <synonym>6-Caprolactam</synonym>
    <synonym>6-Hexanelactam</synonym>
    <synonym>Akulon</synonym>
    <synonym>Alkamid</synonym>
    <synonym>Amilan cm 1001</synonym>
    <synonym>Aminocaproic lactam</synonym>
    <synonym>Aza-2-cycloheptanone</synonym>
    <synonym>azepan-2-one</synonym>
    <synonym>Bonamid</synonym>
    <synonym>Capran 77C</synonym>
    <synonym>Caprolactam</synonym>
    <synonym>Caprolactam monomer</synonym>
    <synonym>Caprolattame</synonym>
    <synonym>Caprolon v</synonym>
    <synonym>Capron</synonym>
    <synonym>Chemlon</synonym>
    <synonym>cis-Hexahydro-2-azepinone</synonym>
    <synonym>Cyclohexanone iso-oxime</synonym>
    <synonym>Danamid</synonym>
    <synonym>Durethan BK</synonym>
    <synonym>E-caprolactam</synonym>
    <synonym>E-caprolactum</synonym>
    <synonym>Epsilon-caprolactam</synonym>
    <synonym>Ertalon 6sa</synonym>
    <synonym>Extrom 6N</synonym>
    <synonym>Gamma-caprolactam</synonym>
    <synonym>Grilon</synonym>
    <synonym>Hexahydro-2-azepinone</synonym>
    <synonym>Hexahydro-2H-azepin-2-one</synonym>
    <synonym>Hexannic acid</synonym>
    <synonym>hexanoic acid-6-amino-lactam</synonym>
    <synonym>Hexanolactam</synonym>
    <synonym>Hexanone isoxime</synonym>
    <synonym>Itamid</synonym>
    <synonym>Kaprolit</synonym>
    <synonym>Kaprolon</synonym>
    <synonym>Kapromine</synonym>
    <synonym>Kapron</synonym>
    <synonym>Maranyl F 114</synonym>
    <synonym>Metamid</synonym>
    <synonym>Miramid H 2</synonym>
    <synonym>Nipro (I)</synonym>
    <synonym>Nylon A1035sf</synonym>
    <synonym>Omega-caprolactum</synonym>
    <synonym>Orgamid rmnocd</synonym>
    <synonym>Orgamide</synonym>
    <synonym>Perhydroazepin-2-one</synonym>
    <synonym>Plaskin 8200</synonym>
    <synonym>Plaskon 201</synonym>
    <synonym>Polyamide pk 4</synonym>
    <synonym>Relon p</synonym>
    <synonym>Renyl MV</synonym>
    <synonym>Sipas 60</synonym>
    <synonym>Spencer 401</synonym>
    <synonym>Spencer 601</synonym>
    <synonym>Steelon</synonym>
    <synonym>Stilon</synonym>
    <synonym>Stylon</synonym>
    <synonym>Tarlon x-a</synonym>
    <synonym>Tarlon XB</synonym>
    <synonym>Tarnamid T 2</synonym>
    <synonym>Tarnamid T 27</synonym>
    <synonym>TNK 2G5</synonym>
    <synonym>Torayca N 6</synonym>
    <synonym>U-caprolactam</synonym>
    <synonym>Ultramid BMK</synonym>
    <synonym>Vidlon</synonym>
    <synonym>Widlon</synonym>
    <synonym>Zytel 211</synonym>
  </synonyms>
  <chemical_formula>C6H11NO</chemical_formula>
  <average_molecular_weight>113.1576</average_molecular_weight>
  <monisotopic_moleculate_weight>113.084063979</monisotopic_moleculate_weight>
  <iupac_name>azepan-2-one</iupac_name>
  <traditional_iupac>caprolactam</traditional_iupac>
  <cas_registry_number>105-60-2</cas_registry_number>
  <smiles>O=C1CCCCCN1</smiles>
  <inchi>InChI=1S/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8)</inchi>
  <inchikey>JBKVHLHDHHXQEQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as caprolactams. These are cyclic amides of caproic acid. Caproic acid is the carboxylic acid derived from hexane with the general formula C5H11COOH.</description>
    <direct_parent>Caprolactams</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Lactams</class>
    <sub_class>Caprolactams</sub_class>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Azepanes</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azepane</substituent>
      <substituent>Caprolactam</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a lactam</external_descriptor>
      <external_descriptor>caprolactams</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.56e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>69.3 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>14.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-1.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>azepan-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>113.1576</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>113.084063979</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>O=C1CCCCCN1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C6H11NO</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>JBKVHLHDHHXQEQ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>29.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>31.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>12.47</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</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::EiMs</type>
      <spectrum_id>1434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>10583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>10584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>10585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>34015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>131211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>138945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136488</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3050069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3050070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3050071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3119887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3119888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3119889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3619</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69552</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>69553</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>69554</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>69555</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>69556</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69557</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69558</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69559</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69560</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69561</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69562</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69563</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69569</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69570</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>69571</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>28579</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Sunflower</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Helianthus annuus</name_scientific>
      <ncbi_taxonomy_id>4232</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>amine</name>
    </flavor>
    <flavor>
      <name>bitter</name>
    </flavor>
    <flavor>
      <name>spicy</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Allelochemic</name>
      <id>41</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Herbicide</name>
      <id>986</id>
      <definition>A substance used to destroy plant pests.</definition>
    </health_effect>
    <health_effect>
      <name>Pesticide</name>
      <id>1210</id>
      <definition>Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.</definition>
    </health_effect>
  </health_effects>
</compound>
