<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:51 UTC</creation_date>
  <update_date>2025-11-18 23:31:30 UTC</update_date>
  <accession>FDB011843</accession>
  <name>4-(4-Hydroxyphenyl)-2-butanone</name>
  <description>Isolated from raspberries (Rubus idaeus), rhubarb (Rheum subspecies), European cranberry (Vaccinium oxycoccus), blackberry, loganberry and redcurrants. Important flavour ingredient. 4-(4-Hydroxyphenyl)-2-butanone is found in fruits and red raspberry.</description>
  <synonyms>
    <synonym>(p-hydroxybenzyl)acetone</synonym>
    <synonym>1-(4-Hydroxyphenyl)-3-butanone</synonym>
    <synonym>1-(p-Hydroxyphenyl)-3-butanone</synonym>
    <synonym>2-Butanone, 4-(4-hydroxyphenyl)-</synonym>
    <synonym>2-Butanone, 4-(p-hydroxyphenyl)-</synonym>
    <synonym>4-(3-Oxobutyl)phenol</synonym>
    <synonym>4-(4-Hydroxyphenyl)butan-2-one</synonym>
    <synonym>4-(p-Hydroxyphenyl)-2-butanone</synonym>
    <synonym>4-Hydroxybenzylacetone</synonym>
    <synonym>Betuligenol</synonym>
    <synonym>FEMA 2588</synonym>
    <synonym>Frambinone</synonym>
    <synonym>Hydroxyphenylbutanone, p-</synonym>
    <synonym>Oxyphenalon</synonym>
    <synonym>P-hydroxybenzyl acetone</synonym>
    <synonym>p-hydroxyphenylbutan-2-one</synonym>
    <synonym>P-Hydroxyphenylbutanone</synonym>
    <synonym>Rasberry ketone</synonym>
    <synonym>Rasketone</synonym>
    <synonym>Raspberry ketone</synonym>
    <synonym>Rheosmin</synonym>
    <synonym>Rheosmine</synonym>
  </synonyms>
  <chemical_formula>C10H12O2</chemical_formula>
  <average_molecular_weight>164.2011</average_molecular_weight>
  <monisotopic_moleculate_weight>164.083729628</monisotopic_moleculate_weight>
  <iupac_name>4-(4-hydroxyphenyl)butan-2-one</iupac_name>
  <traditional_iupac>raspberry ketone</traditional_iupac>
  <cas_registry_number>5471-51-2</cas_registry_number>
  <smiles>CC(=O)CCC1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3</inchi>
  <inchikey>NJGBTKGETPDVIK-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>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a polyketide</external_descriptor>
      <external_descriptor>methyl ketone</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.02e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 82.5°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.08</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.51</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4-(4-hydroxyphenyl)butan-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>164.2011</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>164.083729628</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(=O)CCC1=CC=C(O)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H12O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>NJGBTKGETPDVIK-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>37.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>47.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>18.02</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</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::MsIr</type>
      <spectrum_id>6216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>43465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>101374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>137350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>145084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2246429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2247843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2248543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2249845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2250514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2251862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2690045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2690046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2690047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2989565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2989566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2989567</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB33723</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce33317458&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Fruits</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Red raspberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rubus idaeus</name_scientific>
      <ncbi_taxonomy_id>32247</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>berry</name>
    </flavor>
    <flavor>
      <name>floral</name>
    </flavor>
    <flavor>
      <name>jam</name>
    </flavor>
    <flavor>
      <name>raspberry</name>
    </flavor>
    <flavor>
      <name>ripe</name>
    </flavor>
    <flavor>
      <name>sweet</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
