<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2009-07-30 17:56:21 UTC</creation_date>
  <update_date>2026-03-31 19:26:03 UTC</update_date>
  <accession>T3D3201</accession>
  <common_name>4-Ethylphenol</common_name>
  <class>SmallMolecule</class>
  <description>4-Ethylphenol is a solid compound with the formula C8H10O and an average molecular weight of 122.16 g/mol. 4-Ethylphenol belongs to the 1-hydroxy-2-unsubstituted benzenoids, a subclass of phenols within the organic compounds. It is categorized as an exogenous benzenoid.

The compound serves various industrial roles as a fragrance, a flavouring and nutrient, a surface modifier, and as processing aids not otherwise specified. Biologically, it acts as a fungal xenobiotic metabolite. 4-Ethylphenol is recorded as being released from 24 sources. These include building and construction materials such as ceilings, as well as household cleaning and consumer products including tobacco product cases, cigar cigarettes, and bleaching agents. It is found in food, food processing and cookware, specifically in food contact materials, cellar tools, the preparation of vinegar, the preparation of wine or sparkling wine, and fermentation processes for beer. Additionally, it is released from electrical and electronic equipment, including antennas, adjustable resistors, auxiliary devices, coils, cores yokes or armatures, and eight other sources. It is also released in low-density polyethylene plastics.

Exposure to 4-Ethylphenol can occur through oral, inhalation, and touch routes. In terms of biological activity, the compound has two recorded protein targets: estrogen receptor beta (ESR2) and estrogen receptor (ESR1).</description>
  <categories>
    <category>Household Toxin</category>
    <category>Food Toxin</category>
    <category>Natural Toxin</category>
    <category>Fungal Toxin</category>
  </categories>
  <types>
    <type>Organic Compound</type>
    <type>Food Toxin</type>
    <type>Metabolite</type>
    <type>Fragrance Toxin</type>
    <type>Household Toxin</type>
    <type>Fungal Toxin</type>
    <type>Natural Compound</type>
  </types>
  <synonyms>
    <synonym>1-Ethyl-4-hydroxybenzene</synonym>
    <synonym>1-Hydroxy-4-ethylbenzene</synonym>
    <synonym>4-Hydroxyphenylethane</synonym>
    <synonym>P-ETHYLPHENOL</synonym>
    <synonym>p-Ethylphenol</synonym>
    <synonym>Phenol, ethyl-</synonym>
  </synonyms>
  <chemical_formula>C8H10O</chemical_formula>
  <average_molecular_weight>122.1644</average_molecular_weight>
  <monisotopic_moleculate_weight>122.073164942</monisotopic_moleculate_weight>
  <iupac_name>4-ethylphenol</iupac_name>
  <traditional_iupac>ethylphenol</traditional_iupac>
  <cas_registry_number>123-07-9</cas_registry_number>
  <smiles>CCC1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3</inchi>
  <inchikey>HXDOZKJGKXYMEW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-2-unsubstituted benzenoids</sub_class>
    <direct_parent>1-hydroxy-2-unsubstituted benzenoids</direct_parent>
    <alternate_parents>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternate_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>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>an aromatic compound</descriptor>
      <descriptor>phenols</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin>Exogenous</origin>
  <cellular_locations>
    <cellular_location>Membrane</cellular_location>
  </cellular_locations>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Metabolsim and Physiological Effects of 4-Ethylphenylsulfate</name>
      <smpdb_id>SMP0125541</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state>Solid</state>
  <appearance>White powder.</appearance>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>45.0°C</value>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.9 mg/mL at 25°C [YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)]</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.15e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-ethylphenol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>122.1644</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>122.073164942</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H10O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HXDOZKJGKXYMEW-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>37.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</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>
  </predicted_properties>
  <route_of_exposure>Dermal (T36) ; inhalation (T36) ; oral (T36)</route_of_exposure>
  <mechanism_of_toxicity>Metabolized to 1- and 2- phenylethanol (A622).</mechanism_of_toxicity>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity>No indication of carcinogenicity (not listed by IARC). (L135)</carcinogenicity>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bae766420&gt;</health_effects>
  <symptoms>Systemic manifestations of toxicity may include nausea, vomiting, diarrhea, dyspnea, tachypnea, pallor, and profuse sweating (T36).</symptoms>
  <treatment>Consider activated charcoal. Monitor for respiratory distress in case of inhalation exposure. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. (T36)</treatment>
  <drugbank_id/>
  <hmdb_id>HMDB29306</hmdb_id>
  <pubchem_compound_id>31242</pubchem_compound_id>
  <chembl_id>CHEMBL108475</chembl_id>
  <chemspider_id>28982</chemspider_id>
  <kegg_id>C13637</kegg_id>
  <uniprot_id/>
  <omim_id/>
  <chebi_id>49584</chebi_id>
  <biocyc_id>CPD-10489</biocyc_id>
  <ctd_id/>
  <stitch_id>Ethylphenol, para-</stitch_id>
  <actor_id>1886</actor_id>
  <pdb_id>ETY</pdb_id>
  <wikipidia>http://en.wikipedia.org/wiki/4-Ethylphenol</wikipidia>
  <general_references>
    <reference>
      <pubmed_id>11243491</pubmed_id>
    </reference>
    <reference>
      <reference_text>Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.</reference_text>
    </reference>
    <reference>
      <reference_text>Clayton GD and Clayton FE (eds) (1981-1982). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons.</reference_text>
    </reference>
    <reference>
      <reference_text>International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. : http://monographs.iarc.fr/index.php</reference_text>
    </reference>
    <reference>
      <reference_text>Wikipedia. 4-Ethylphenol. Last Updated 22 January 2009.: http://en.wikipedia.org/wiki/4-Ethylphenol</reference_text>
    </reference>
  </general_references>
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</compound>
