Showing Compound Card for p-Ethylphenol (CDB005789)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-27 16:56:44 UTC
Updated at2021-01-04 18:49:20 UTC
CannabisDB IDCDB005789
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namep-Ethylphenol
Description4-Ethylphenol, 4-EP or p-Ethylphenol is an ethylated derivative of phenol. It 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 one of three structural isomers of ethylphenol wherein the ethyl group is substituted at three positions of phenol (the ortho, meta and para positions). 4-Ethylphenol is also classified as an alcohol. It exists as a white solid that is weakly soluble in water. It has a smoky, phenolic, guaiacol odor and a smoky, bacon or ham flavor. It is used in the cosmetic industry as a perfuming agent. 4-Ethylphenol exists in all living species, ranging from bacteria to plants to humans. 4-Ethylphenol has been detected, but not quantified in, several different plants, foods and beverages such as arabica coffee, wine, beers, cottage cheese, corn, cranberries, fish, pork, milk, wine and red raspberries. This could make 4-ethylphenol a potential biomarker for the consumption of these foods. 4-Ethylphenol is produced in wine and beer by the yeast Brettanomyces. In wines 4-EP is generally undesirable while in certain Belian beers, it can be desirable. 4-Ethylphenol at the concentration of 140 µg/L gives wines a barnyard, medicinal, or mousy aroma. In plants and yeast, 4-EP is produced from the precursor p-coumaric acid. This is converted to 4-vinylphenol via the enzyme cinnamate decarboxylase which is further reduced to 4-Ethylphenol by the enzyme vinyl phenol reductase. At high doses, 4-Ethylphenol is a potentially toxic compound. 4-Ethylphenol poisoning can lead to respiratory distress, cardiovascular collapse, shock, ventricular tachycardia, and coma. Liver, lung, central nervous system and renal injury may also occur. Systemic manifestations of toxicity may include nausea, vomiting, diarrhea, dyspnea, tachypnea, pallor, and profuse sweating. p-Ethylphenol is one of several phenolic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Ethyl-4-hydroxybenzeneChEBI
1-Hydroxy-4-ethylbenzeneChEBI
p-EthylphenolChEBI
Para-ethylphenolChEBI
ParaethylphenolChEBI
4-HydroxyphenylethaneHMDB
4-Ethylphenol, sodium saltMeSH, HMDB
Chemical FormulaC8H10O
Average Molecular Weight122.16
Monoisotopic Molecular Weight122.0732
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-4900000000-7c02c635b2eaaec859412014-09-20View Spectrum
GC-MSp-Ethylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-4900000000-45f09ef08787a27c168fSpectrum
GC-MSp-Ethylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-4900000000-49d46baa756331ae6778Spectrum
GC-MSp-Ethylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-3900000000-8b361994c5f7ad64360eSpectrum
GC-MSp-Ethylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-4900000000-45f09ef08787a27c168fSpectrum
GC-MSp-Ethylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-4900000000-49d46baa756331ae6778Spectrum
GC-MSp-Ethylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-3900000000-8b361994c5f7ad64360eSpectrum
Predicted GC-MSp-Ethylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-7900000000-05a65f70c1492e66a757Spectrum
Predicted GC-MSp-Ethylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fu-7900000000-3dec7f128e63d8a41f56Spectrum
Predicted GC-MSp-Ethylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-fdbf6912a7ccf149feef2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-4b8b9fb03827c8f5a5a62016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdl-9200000000-89814f9e00f72af2063d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-97e83cc78ca8f67f1e462016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-6c86b9784be37918b1732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9700000000-6d6b9f71e47253eb13d02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3900000000-ca25854e387486e0a9bb2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016v-9000000000-dfe72983f410cb801cc42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-9000000000-2db0d010ac93173dee862021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-99acd0a74fdc923b28382021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2900000000-7639744c151c0846bda62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-6817cd5ae49f30b5ca1a2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, benzene, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, benzene, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
Sulfotransferase 1A3SULT1A3P0DMM9 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029306
DrugBank IDNot Available
Phenol Explorer Compound ID707
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
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
Enzyme Details
2. Sulfotransferase 1A3
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