<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:06:25 UTC</creation_date>
  <update_date>2025-11-18 22:57:36 UTC</update_date>
  <accession>FDB004830</accession>
  <name>Azulene</name>
  <description>Azulene, also known as cyclopentacycloheptene or azulekeep, is a member of the class of compounds known as azulenes. Azulenes are polycyclic aromatic compounds containing the azulene skeleton, which consists of the cyclopentadiene ring fused to a cycloheptadiene ring. Azulene can be found in a number of food items such as anise, roman camomile, peppermint, and german camomile, which makes azulene a potential biomarker for the consumption of these food products. Azulene is a non-carcinogenic (not listed by IARC) potentially toxic compound. Azulene is an organic compound and an isomer of naphthalene. Whereas naphthalene is colourless, azulene is dark blue. Two terpenoids, vetivazulene (4,8-dimethyl-2-isopropylazulene) and guaiazulene (1,4-dimethyl-7-isopropylazulene), that feature the azulene skeleton are found in nature as constituents of pigments in mushrooms, guaiac wood oil, and some marine invertebrates . PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system (L10) (T3DB).</description>
  <synonyms>
    <synonym>Azotesin</synonym>
    <synonym>Azulekeep</synonym>
    <synonym>Azulen</synonym>
    <synonym>AZULENE, M.P. 99 C</synonym>
    <synonym>Azunamic</synonym>
    <synonym>Azusalen [as sodium sulfonate]</synonym>
    <synonym>Bicyclo(0.3.5)deca-1,3,5,7,9-pentaene</synonym>
    <synonym>Bicyclo(5.3.0)-1,3,5,7,9-decapentaene</synonym>
    <synonym>BICYCLO(5.3.0)-DECA-2,4,6,8,10-PENTAENE</synonym>
    <synonym>Bicyclo(5.3.0)decapentaene</synonym>
    <synonym>Bicyclo[5.3.0]-1,3,5,7,9-decapentaene</synonym>
    <synonym>Bicyclo[5.3.0]decapentaene</synonym>
    <synonym>Cyclopentacycloheptene</synonym>
  </synonyms>
  <chemical_formula>C10H8</chemical_formula>
  <average_molecular_weight>128.1705</average_molecular_weight>
  <monisotopic_moleculate_weight>128.062600256</monisotopic_moleculate_weight>
  <iupac_name>azulene</iupac_name>
  <traditional_iupac>azulene</traditional_iupac>
  <cas_registry_number>275-51-4</cas_registry_number>
  <smiles>C1=CC2=CC=CC=CC2=C1</smiles>
  <inchi>InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H</inchi>
  <inchikey>CUFNKYGDVFVPHO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as azulenes. These are polycyclic aromatic compounds containing the azulene skeleton, which consists of the cyclopentadiene ring fused to a cycloheptadiene ring.</description>
    <direct_parent>Azulenes</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Hydrocarbons</super_class>
    <class>Unsaturated hydrocarbons</class>
    <sub_class>Olefins</sub_class>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Aromatic hydrocarbons</alternative_parent>
      <alternative_parent>Polycyclic hydrocarbons</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Aromatic hydrocarbon</substituent>
      <substituent>Azulene</substituent>
      <substituent>Polycyclic hydrocarbon</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>azulenes</external_descriptor>
      <external_descriptor>mancude carbobicyclic parent</external_descriptor>
      <external_descriptor>ortho-fused bicyclic arene</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.13e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>99 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>azulene</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>128.1705</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>128.062600256</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>C1=CC2=CC=CC=CC2=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>CUFNKYGDVFVPHO-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>42.51</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>14.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>0</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::EiMs</type>
      <spectrum_id>1086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>114981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>129189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417634</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>31249</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Anise</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pimpinella anisum</name_scientific>
      <ncbi_taxonomy_id>271192</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Carrot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Daucus carota ssp. sativus</name_scientific>
      <ncbi_taxonomy_id>79200</ncbi_taxonomy_id>
    </food>
    <food>
      <name>German camomile</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Matricaria recutita</name_scientific>
      <ncbi_taxonomy_id>127986</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Peppermint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha X piperita</name_scientific>
      <ncbi_taxonomy_id>34256</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Roman camomile</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Chamaemelum nobile</name_scientific>
      <ncbi_taxonomy_id>99037</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet cherry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Prunus avium</name_scientific>
      <ncbi_taxonomy_id>42229</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Turmeric</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Curcuma longa</name_scientific>
      <ncbi_taxonomy_id>136217</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild carrot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Daucus carota</name_scientific>
      <ncbi_taxonomy_id>4039</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti bacterial</name>
      <id>145</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Anti histaminic</name>
      <id>331</id>
      <definition>Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.</definition>
    </health_effect>
    <health_effect>
      <name>Anti pyretic</name>
      <id>567</id>
      <definition>A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.</definition>
    </health_effect>
    <health_effect>
      <name>Anti septic</name>
      <id>603</id>
      <definition>A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.</definition>
    </health_effect>
    <health_effect>
      <name>Anti ulcer</name>
      <id>676</id>
      <definition>One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-allergic</name>
      <id>103</id>
      <definition>A drug used to treat allergic reactions.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-inflammatory</name>
      <id>370</id>
      <definition>A substance that reduces or suppresses inflammation.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-spasmodic</name>
      <id>619</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Hepatoregenerative</name>
      <id>982</id>
      <definition>Any compound that is able to prevent damage to the liver.</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>
