<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2013-04-25 07:56:53 UTC</creation_date>
  <update_date>2026-05-14 19:08:36 UTC</update_date>
  <accession>T3D3900</accession>
  <common_name>2-Phenoxyethanol</common_name>
  <class>SmallMolecule</class>
  <description>2-Phenoxyethanol belongs to the phenol ethers, a class of benzenoids within the organic compounds. This exogenous liquid has the formula C8H10O2 and an average molecular weight of 138.17 g/mol. It acts on protein targets including Glutamate receptor ionotropic, NMDA 2A (GRIN2A) and ADP-ribosyl cyclase/cyclic ADP-ribose hydrolase 1 (CD38).

The compound serves numerous industrial roles as a preservative, biocide, antioxidant, fragrance, and additive (PMC10698095). It is further utilized as a solvent, solubility enhancer, plasticizer, film former, processing aid, flavouring and nutrient, and as an antiinfective agent and central nervous system depressant (PMC10698095). 2-Phenoxyethanol is released from 24 recorded sources, including drinking water, pesticides, and food contact materials. Other sources include building and construction materials such as ceilings, fencing, and tents, as well as household cleaning and consumer products like soap dispensers, bleaching agents, and pipe accessories. It is also found in electrical and electronic equipment, including antennas, discharge lamps, electric switches, adjustable resistors, and electrically stimulated smoking devices. Recorded exposure routes for the compound include oral, inhalation, and touch.</description>
  <categories>
    <category>Industrial/Workplace Toxin</category>
    <category>Pollutant</category>
    <category>Airborne Pollutant</category>
    <category>Food Toxin</category>
    <category>Synthetic Toxin</category>
  </categories>
  <types>
    <type>Organic Compound</type>
    <type>Solvent</type>
    <type>Pesticide</type>
    <type>Ether</type>
    <type>Pollutant</type>
    <type>Food Toxin</type>
    <type>Metabolite</type>
    <type>Preservative</type>
    <type>Dye</type>
    <type>Cosmetic Toxin</type>
    <type>Industrial/Workplace Toxin</type>
    <type>Synthetic Compound</type>
  </types>
  <synonyms>
    <synonym>1-Hydroxy-2-phenoxyethane</synonym>
    <synonym>2-Hydroxyethyl phenyl ether</synonym>
    <synonym>2-phenoxyethan-1-ol</synonym>
    <synonym>2-Phenoxyethanol, 9CI</synonym>
    <synonym>Dalpad A</synonym>
    <synonym>Ethanol, 2-phenoxy-</synonym>
    <synonym>ETHYLENE GLYCOL MONOPHENYL ETHER</synonym>
    <synonym>Ethylene glycol monophenyl ether</synonym>
    <synonym>Ethylene glycol phenyl ether</synonym>
    <synonym>Newpol EFP</synonym>
    <synonym>Phenoxetol</synonym>
    <synonym>Phenoxyethanol</synonym>
    <synonym>Phenylcellosolve</synonym>
    <synonym>Poly(oxy-1,2-ethanediyl), .alpha.-phenyl-.omega.-hydroxy-</synonym>
  </synonyms>
  <chemical_formula>C8H10O2</chemical_formula>
  <average_molecular_weight>138.166</average_molecular_weight>
  <monisotopic_moleculate_weight>138.068079562</monisotopic_moleculate_weight>
  <iupac_name>2-phenoxyethan-1-ol</iupac_name>
  <traditional_iupac>phenoxyethanol</traditional_iupac>
  <cas_registry_number>122-99-6</cas_registry_number>
  <smiles>C1=CC=C(C=C1)OCCO</smiles>
  <inchi>InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2</inchi>
  <inchikey>QCDWFXQBSFUVSP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenol ethers</class>
    <sub_class/>
    <direct_parent>Phenol ethers</direct_parent>
    <alternate_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>aromatic ether</descriptor>
      <descriptor>hydroxyether</descriptor>
      <descriptor>primary alcohol</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin>Exogenous</origin>
  <cellular_locations>
    <cellular_location>Cytoplasm</cellular_location>
    <cellular_location>Extracellular</cellular_location>
  </cellular_locations>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state>Liquid</state>
  <appearance>Colorless oily liquid.</appearance>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>11-13°C</value>
    </property>
    <property>
      <kind>boiling_point</kind>
      <value>245.2°C (473.4°F)</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.41e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-phenoxyethan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>138.166</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>138.068079562</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C1=CC=C(C=C1)OCCO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H10O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QCDWFXQBSFUVSP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>29.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.91</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>
  </predicted_properties>
  <route_of_exposure>Dermal (A15201); ingestion</route_of_exposure>
  <mechanism_of_toxicity>2-Phenoxyethanol is a glycol ether. Glycol ethers can produce toxicity following oxidation to the corresponding aldehyde and alkoxyacetic acid by alcohol dehydrogenase (ADH; EC 1.1.1.1) and aldehyde dehydrogenase (ALDH; EC 1.2.1.3), respectively. (A15201) 2-Phenoxyethanol causes reduction of NMDA-induced membrane currents, indicating a neurotoxic potential for 2-phenoxyethanol. (A15202)</mechanism_of_toxicity>
  <metabolism>Oxidized to the corresponding aldehyde and alkoxyacetic acid by alcohol dehydrogenase (ADH; EC 1.1.1.1) and aldehyde dehydrogenase (ALDH; EC 1.2.1.3), respectively. (A15201)</metabolism>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use_source>2-Phenoxyethanol is used in many applications such as cosmetics, vaccines and pharmaceuticals as a preservative. It is also used as a fixative for perfumes, an insect repellent, a topical antiseptic, a solvent for cellulose acetate, some dyes, inks, and resins, in preservatives, pharmaceuticals, and in organic synthesis.</use_source>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7227b7d180&gt;</health_effects>
  <symptoms>May cause vomiting and diarrhea.</symptoms>
  <treatment/>
  <drugbank_id>DB11304</drugbank_id>
  <hmdb_id>HMDB41607</hmdb_id>
  <pubchem_compound_id>31236</pubchem_compound_id>
  <chembl_id>CHEMBL1229846</chembl_id>
  <chemspider_id>13848467</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id>64275</chebi_id>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id>268</pdb_id>
  <wikipidia/>
  <general_references>
    <reference>
      <pubmed_id>15551062</pubmed_id>
    </reference>
    <reference>
      <pubmed_id>10207615</pubmed_id>
    </reference>
    <reference>
      <reference_text>Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman &amp; Hall/CRC.</reference_text>
    </reference>
  </general_references>
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          <units>uM</units>
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          <assay_source>BioSeek</assay_source>
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</compound>
