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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:29:34 UTC
Update Date2020-02-26 21:43:20 UTC
HMDB IDHMDB0029306
Secondary Accession Numbers
  • HMDB29306
Metabolite Identification
Common Name4-Ethylphenol
Description4-Ethylphenol belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. 4-Ethylphenol is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Ethylphenol exists in all living species, ranging from bacteria to humans. 4-Ethylphenol is an alcohol, castoreum, and guaiacol tasting compound. Outside of the human body, 4-Ethylphenol has been detected, but not quantified in, several different foods, such as arabica coffee, beers, corns, milk (cow), and red raspberries. This could make 4-ethylphenol a potential biomarker for the consumption of these foods. Respiratory distress, cardiovascular collapse, shock, ventricular tachycardia, and coma in an adult. 4-Ethylphenol is a potentially toxic compound. Liver, lung, central nervous system and renal injury may also occur (T36). Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Monitor for respiratory distress in case of inhalation exposure. Systemic manifestations of toxicity may include nausea, vomiting, diarrhea, dyspnea, tachypnea, pallor, and profuse sweating (T36). Consider activated charcoal.
Structure
Data?1582753400
Synonyms
ValueSource
1-Ethyl-4-hydroxybenzeneChEBI
1-Hydroxy-4-ethylbenzeneChEBI
p-EthylphenolChEBI
Para-ethylphenolChEBI
ParaethylphenolChEBI
4-HydroxyphenylethaneHMDB
4-Ethylphenol, sodium saltHMDB
Chemical FormulaC8H10O
Average Molecular Weight122.1644
Monoisotopic Molecular Weight122.073164942
IUPAC Name4-ethylphenol
Traditional Nameethylphenol
CAS Registry Number123-07-9
SMILES
CCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3
InChI KeyHXDOZKJGKXYMEW-UHFFFAOYSA-N
Chemical 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.15 g/LALOGPS
logP2.54ALOGPS
logP2.63ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.32ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.68 m³·mol⁻¹ChemAxon
Polarizability13.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4900000000-45f09ef08787a27c168fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4900000000-49d46baa756331ae6778Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3900000000-8b361994c5f7ad64360eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4900000000-45f09ef08787a27c168fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4900000000-49d46baa756331ae6778Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3900000000-8b361994c5f7ad64360eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-7900000000-05a65f70c1492e66a757Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fu-7900000000-3dec7f128e63d8a41f56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-fdbf6912a7ccf149feefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-4b8b9fb03827c8f5a5a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdl-9200000000-89814f9e00f72af2063dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-97e83cc78ca8f67f1e46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-6c86b9784be37918b173Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9700000000-6d6b9f71e47253eb13d0Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-4900000000-7c02c635b2eaaec85941Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.221 +/- 0.119 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.414 +/- 0.247 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified19.555 +/- 18.35 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 707 details
BloodDetected and Quantified1.975 +/- 0.639 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.484 +/- 0.232 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.2 +/- 0.626 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.58 +/- 0.272 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.408 +/- 0.166 uMAdult (>18 years old)Male
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 707 details
UrineDetected and Quantified0.9 (0.6-1.2) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.409 +/- 0.174 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.854 +/- 0.209 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID707
FooDB IDFDB000358
KNApSAcK IDC00029528
Chemspider ID28982
KEGG Compound IDC13637
BioCyc IDCPD-10596
BiGG IDNot Available
Wikipedia Link4-Ethylphenol
METLIN IDNot Available
PubChem Compound31242
PDB IDETY
ChEBI ID49584
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Ethylphenol → 6-(4-ethylphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
4-Ethylphenol → 4-Ethylphenylsulfatedetails