<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:09 UTC</creation_date>
  <update_date>2025-11-18 23:19:39 UTC</update_date>
  <accession>FDB010503</accession>
  <name>4'-Hydroxyacetophenone</name>
  <description>4'-hydroxyacetophenone, also known as (4-hydroxyphenyl)ethan-1-one or 4-acetylphenol, is a member of the class of compounds known as alkyl-phenylketones. Alkyl-phenylketones are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4'-hydroxyacetophenone is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4'-hydroxyacetophenone is a mild, sweet, and balsam tasting compound found in sweet orange, which makes 4'-hydroxyacetophenone a potential biomarker for the consumption of this food product. </description>
  <synonyms>
    <synonym>1-(4-Hydroxyphenyl)ethanone, 9CI</synonym>
    <synonym>4-Acetylphenol</synonym>
    <synonym>4-Hydroxyacetophenone</synonym>
    <synonym>4-Hydroxyphenyl methyl ketone</synonym>
    <synonym>Ameliarol</synonym>
    <synonym>Ethanone, 1-(4-hydroxyphenyl)-</synonym>
    <synonym>Methyl p-hydroxyphenyl ketone</synonym>
    <synonym>p-Acetylphenol</synonym>
    <synonym>p-Hydroxyacetophenone</synonym>
    <synonym>p-Hydroxyphenyl methyl ketone</synonym>
    <synonym>p-Oxyacetophenone</synonym>
    <synonym>para-Hydroxyacetophenone</synonym>
    <synonym>Piceol</synonym>
  </synonyms>
  <chemical_formula>C8H8O2</chemical_formula>
  <average_molecular_weight>136.1479</average_molecular_weight>
  <monisotopic_moleculate_weight>136.0524295</monisotopic_moleculate_weight>
  <iupac_name>1-(4-hydroxyphenyl)ethan-1-one</iupac_name>
  <traditional_iupac>4-hydroxyacetophenone</traditional_iupac>
  <cas_registry_number>99-93-4</cas_registry_number>
  <smiles>CC(=O)C1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3</inchi>
  <inchikey>TXFPEBPIARQUIG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.</description>
    <direct_parent>Alkyl-phenylketones</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Acetophenones</alternative_parent>
      <alternative_parent>Aryl alkyl ketones</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Acetophenone</substituent>
      <substituent>Alkyl-phenylketone</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Phenol</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a methyl-ethyl-ketone</external_descriptor>
      <external_descriptor>an aromatic compound</external_descriptor>
      <external_descriptor>monohydroxyacetophenone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.02e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 109°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>7.79</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-6.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1-(4-hydroxyphenyl)ethan-1-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>136.1479</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>136.0524295</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(=O)C1=CC=C(O)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C8H8O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>TXFPEBPIARQUIG-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>38.44</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>14.03</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>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::MsMs</type>
      <spectrum_id>109545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>94182</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>28032</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Sweet orange</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus sinensis</name_scientific>
      <ncbi_taxonomy_id>2711</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>balsam</name>
    </flavor>
    <flavor>
      <name>hawthorn</name>
    </flavor>
    <flavor>
      <name>mild</name>
    </flavor>
    <flavor>
      <name>mimosa</name>
    </flavor>
    <flavor>
      <name>sweet</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
