<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:11:18 UTC</creation_date>
  <update_date>2019-11-26 03:10:11 UTC</update_date>
  <accession>FDB014503</accession>
  <name>Ascaridole</name>
  <description>Said to be the major constituent of oil of Peumus boldus (boldo)

Ascaridole is a natural organic compound classified as a bicyclic monoterpene that has an unusual bridging peroxide functional group. It is the primary constituent of the oil of Mexican Tea (Dysphania ambrosioides, formerly Chenopodium ambrosioides).; It is a colorless liquid that is soluble in most organic solvents. Like other low molecular weight organic peroxides, it is unstable and prone to explosion when heated or treated with organic acids. Ascaridole is found in cardamom, fruits, and lambsquarters.</description>
  <synonyms>
    <synonym>1-Isopropyl-4-methyl-2,3-dioxabicyclo(2.2.2)oct-5-ene</synonym>
    <synonym>1-Isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene</synonym>
    <synonym>1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]hept-2-ene</synonym>
    <synonym>1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo(2.2.2)oct-5-ene</synonym>
    <synonym>1-methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene</synonym>
    <synonym>1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene, 9CI</synonym>
    <synonym>1, 4-Epidioxy-p-menth-2-ene</synonym>
    <synonym>1, 4-Peroxy-p-menth-2-ene</synonym>
    <synonym>1,4-Epidioxy-2-p-menthene</synonym>
    <synonym>1,4-Epidioxy-p-menth-2-ene</synonym>
    <synonym>1,4-Peroxido-p-menthene-2</synonym>
    <synonym>1,4-Peroxy-p-menth-2-ene</synonym>
    <synonym>2,3-Dioxabicyclo(2.2.2)oct-5-ene, 1-isopropyl-4-methyl-</synonym>
    <synonym>2,3-Dioxabicyclo[2.2.2]oct-5-ene, 1-isopropyl-4-methyl-</synonym>
    <synonym>4-methyl-1-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene</synonym>
    <synonym>Ascapurin</synonym>
    <synonym>Ascaricum</synonym>
    <synonym>Ascaridiol</synonym>
    <synonym>Ascaridol</synonym>
    <synonym>Ascaridole (organic peroxide)</synonym>
    <synonym>Ascaridole (organic peroxide) [forbidden]</synonym>
    <synonym>Ascaridole epoxide</synonym>
    <synonym>Ascarisin</synonym>
    <synonym>Askaridol</synonym>
    <synonym>Cis-ascaridole</synonym>
    <synonym>Kebal II</synonym>
    <synonym>p-Menth-2-ene, 1,4-epidioxy-</synonym>
    <synonym>Uncinacina</synonym>
  </synonyms>
  <chemical_formula>C10H16O2</chemical_formula>
  <average_molecular_weight>168.2328</average_molecular_weight>
  <monisotopic_moleculate_weight>168.115029756</monisotopic_moleculate_weight>
  <iupac_name>1-methyl-4-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene</iupac_name>
  <traditional_iupac>ascaridole</traditional_iupac>
  <cas_registry_number>512-85-6</cas_registry_number>
  <smiles>CC(C)C12CCC(C)(OO1)C=C2</smiles>
  <inchi>InChI=1S/C10H16O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6,8H,5,7H2,1-3H3</inchi>
  <inchikey>MGYMHQJELJYRQS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,2-dioxanes. These are organic compounds containing 1,2-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 2.</description>
    <direct_parent>1,2-dioxanes</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Dioxanes</class>
    <sub_class>1,2-dioxanes</sub_class>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Dialkyl peroxides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Dialkyl peroxide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Ortho-dioxane</substituent>
      <substituent>Oxacycle</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Cyclic monoterpenes</external_descriptor>
      <external_descriptor>organic heterobicyclic compound</external_descriptor>
      <external_descriptor>organic peroxide</external_descriptor>
      <external_descriptor>p-menthane monoterpenoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Liquid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.28e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 3.3°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.64</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1-methyl-4-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>168.2328</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>168.115029756</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(C)C12CCC(C)(OO1)C=C2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H16O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H16O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6,8H,5,7H2,1-3H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>MGYMHQJELJYRQS-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>18.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>47.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>18.93</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</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>22750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>130722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>138456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3057799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3057800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3057801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3112544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3112545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3112546</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB35766</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>2866</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce3059c0a0&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Cardamom</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Elettaria cardamomum</name_scientific>
      <ncbi_taxonomy_id>105181</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Fruits</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Lambsquarters</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Chenopodium album</name_scientific>
      <ncbi_taxonomy_id>3559</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Analgesic</name>
      <id>56</id>
      <definition>An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.</definition>
    </health_effect>
    <health_effect>
      <name>Ancylostomicide</name>
      <id>59</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-flatulent</name>
      <id>283</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-helmintic</name>
      <id>72</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-malarial</name>
      <id>416</id>
      <definition>A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.</definition>
    </health_effect>
    <health_effect>
      <name>Carcinogenic</name>
      <id>762</id>
      <definition>A role played by a chemical compound which is known to  induce a process of carcinogenesis  by corrupting  normal cellular pathways, leading to the acquistion of tumoral capabilities.</definition>
    </health_effect>
    <health_effect>
      <name>Carminative</name>
      <id>774</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Fungicide</name>
      <id>940</id>
      <definition>A substance used to destroy fungal pests.</definition>
    </health_effect>
    <health_effect>
      <name>Nematicide</name>
      <id>1141</id>
      <definition>A substance used to destroy pests of the phylum Nematoda (roundworms).</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_effect>
      <name>Plasmodicide</name>
      <id>1233</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Sedative</name>
      <id>1311</id>
      <definition>A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.</definition>
    </health_effect>
    <health_effect>
      <name>Transdermal</name>
      <id>1374</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Trypanocide</name>
      <id>1384</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Vermifuge</name>
      <id>1422</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>
