<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:08 UTC</creation_date>
  <update_date>2025-11-18 23:36:03 UTC</update_date>
  <accession>FDB012373</accession>
  <name>Chavicol</name>
  <description>Found in many essential oils, e.g. anise and Gardenia. It is used in perfumery and flavours.</description>
  <synonyms>
    <synonym>&amp;alpha;-propylene</synonym>
    <synonym>&amp;laquo;gamma&amp;raquo;-(p-hydroxyphenyl)-&amp;alpha;-propylene</synonym>
    <synonym>3-(p-Hydroxyphenyl)-1-propene</synonym>
    <synonym>4-(2-Propenyl)-phenol</synonym>
    <synonym>4-(2-Propenyl)phenol</synonym>
    <synonym>4-(Prop-2-enyl)-phenol</synonym>
    <synonym>4-Allylphenol</synonym>
    <synonym>alpha -Propylene</synonym>
    <synonym>Chavicol</synonym>
    <synonym>g-(P-Hydroxyphenyl)-a-propylene</synonym>
    <synonym>Gamma-(p-hydroxyphenyl)-alpha-propylene</synonym>
    <synonym>Laquo gammaraquo -(P-hydroxyphenyl)-alpha -propylene</synonym>
    <synonym>P-Allyl-phenol</synonym>
    <synonym>p-Allylphenol</synonym>
    <synonym>P-chavicol</synonym>
    <synonym>p-Hydroxyallylbenzene</synonym>
    <synonym>p-Hydroxyallylpropene</synonym>
    <synonym>Phenol, 4-(2-propenyl)-</synonym>
    <synonym>Phenol, 4-(2-propenyl)- (9CI)</synonym>
    <synonym>Phenol, p-allyl-</synonym>
    <synonym>Phenol, p-allyl- (8CI)</synonym>
    <synonym>γ-(P-hydroxyphenyl)-α-propylene</synonym>
  </synonyms>
  <chemical_formula>C9H10O</chemical_formula>
  <average_molecular_weight>134.1751</average_molecular_weight>
  <monisotopic_moleculate_weight>134.073164942</monisotopic_moleculate_weight>
  <iupac_name>4-(prop-2-en-1-yl)phenol</iupac_name>
  <traditional_iupac>chavicol</traditional_iupac>
  <cas_registry_number>501-92-8</cas_registry_number>
  <smiles>OC1=CC=C(CC=C)C=C1</smiles>
  <inchi>InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2</inchi>
  <inchikey>RGIBXDHONMXTLI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.</description>
    <direct_parent>1-hydroxy-2-unsubstituted benzenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-2-unsubstituted benzenoids</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Monolignols</external_descriptor>
      <external_descriptor>a phenol</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
      <external_descriptor>phenylpropanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Liquid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.46e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 16°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.77</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4-(prop-2-en-1-yl)phenol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>134.1751</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>134.073164942</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC1=CC=C(CC=C)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C9H10O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>RGIBXDHONMXTLI-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>20.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>42.33</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>14.95</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</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::CMs</type>
      <spectrum_id>20086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>43712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>148254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2781997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2781998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2781999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2927251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2927252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2927253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>124497</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB34107</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>50158</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce3235dd00&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Allspice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pimenta dioica</name_scientific>
      <ncbi_taxonomy_id>375272</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Chinese cinnamon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cinnamomum aromaticum</name_scientific>
      <ncbi_taxonomy_id>119260</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cloves</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Syzygium aromaticum</name_scientific>
      <ncbi_taxonomy_id>219868</ncbi_taxonomy_id>
      <average_value>48.75</average_value>
      <max_value>48.75</max_value>
      <min_value>48.75</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Fats and oils</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Ginger</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zingiber officinale</name_scientific>
      <ncbi_taxonomy_id>94328</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pineapple</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ananas comosus</name_scientific>
      <ncbi_taxonomy_id>4615</ncbi_taxonomy_id>
      <average_value>0.027</average_value>
      <max_value>0.027</max_value>
      <min_value>0.027</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Sweet basil</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ocimum basilicum</name_scientific>
      <ncbi_taxonomy_id>39350</ncbi_taxonomy_id>
      <average_value>0.3</average_value>
      <max_value>0.3</max_value>
      <min_value>0.3</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Sweet marjoram</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Origanum majorana</name_scientific>
      <ncbi_taxonomy_id>268884</ncbi_taxonomy_id>
      <average_value>46.45</average_value>
      <max_value>46.45</max_value>
      <min_value>46.45</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>medicinal</name>
    </flavor>
    <flavor>
      <name>medicine</name>
    </flavor>
    <flavor>
      <name>phenol</name>
    </flavor>
    <flavor>
      <name>phenolic</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <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_effects>
</compound>
