<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:36:10 UTC</creation_date>
  <update_date>2026-05-14 19:07:55 UTC</update_date>
  <accession/>
  <common_name>2,2'-Dihydroxy-4-methoxybenzophenone</common_name>
  <class>SmallMolecule</class>
  <description>2,2'-Dihydroxy-4-methoxybenzophenone belongs to the benzophenones, a subclass of benzene and substituted derivatives within the organic compounds. This benzenoid compound has the chemical formula C14H12O4 and an average molecular weight of 244.25 g/mol. Industrially, it is utilized as a UV stabilizer.

The compound is found in or released from 18 recorded sources. Within electrical and electronic equipment, it is associated with antennas, auxiliary devices, communication cables or conductors, discharge lamps, and conductors or conductive bodies characterized by the conductive materials, among five other sources. It is present in household cleaning and consumer products, including soap detergents, perfumes within detergents and soaps, cigar cigarettes, tobacco smoke filters, and non-electric simulated smoking devices. Additionally, it is found in household items such as credit card holders and in food preservation and food contact materials. Recorded exposure routes for this substance include oral, inhalation, and touch. Regarding its biological activity, 2,2'-Dihydroxy-4-methoxybenzophenone has one recorded protein target, acting as a binder of sex hormone-binding globulin (SHBG).</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>2,2'-Dihydroxy-4-methoxybenzophenone (BP-8)</synonym>
  </synonyms>
  <chemical_formula>C14H12O4</chemical_formula>
  <average_molecular_weight>244.246</average_molecular_weight>
  <monisotopic_moleculate_weight>244.073558866</monisotopic_moleculate_weight>
  <iupac_name>2-(2-hydroxybenzoyl)-5-methoxyphenol</iupac_name>
  <traditional_iupac>dioxybenzone</traditional_iupac>
  <cas_registry_number>131-53-3</cas_registry_number>
  <smiles>COC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C1O</smiles>
  <inchi>InChI=1S/C14H12O4/c1-18-9-6-7-11(13(16)8-9)14(17)10-4-2-3-5-12(10)15/h2-8,15-16H,1H3</inchi>
  <inchikey>MEZZCSHVIGVWFI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzophenones</sub_class>
    <direct_parent>Benzophenones</direct_parent>
    <alternate_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aryl-phenylketones</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Diphenylmethanes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl ketone</substituent>
      <substituent>Aryl-phenylketone</substituent>
      <substituent>Benzophenone</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Diphenylmethane</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>benzophenones</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Dioxybenzone Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0144637</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>3.97</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.48e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>6.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(2-hydroxybenzoyl)-5-methoxyphenol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>244.246</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>244.073558866</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H12O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H12O4/c1-18-9-6-7-11(13(16)8-9)14(17)10-4-2-3-5-12(10)15/h2-8,15-16H,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MEZZCSHVIGVWFI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
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  <use_source/>
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  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7227bc8ea0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB11221</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>8569</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>8251</chemspider_id>
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</compound>
