You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2006-08-13 16:05:03 UTC
Update Date2017-09-25 16:46:30 UTC
HMDB IDHMDB0004284
Secondary Accession Numbers
  • HMDB04284
StatusDetected but not Quantified
Metabolite Identification
Common NameTyrosol
Description4-(2-hydroxyethyl)phenol is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 2-phenylethan-1-ol. It is generated by cyp2b6 enzyme via a p-hydroxylation-of-monosubstituted-benzene reaction. This p-hydroxylation-of-monosubstituted-benzene occurs in humans.
Structure
Thumb
Synonyms
ValueSource
4-HydroxybenzeneethanolChEBI
4-HydroxyphenylethanolChEBI
P-Hydroxyphenethyl alcoholChEBI
2-(4-Hydroxyphenyl)ethanolHMDB
2-(P-Hydroxyphenyl)ethanolHMDB
4-(2-Hydroxyethyl)phenolHMDB
4-Hydroxyphenethyl alcoholHMDB
4-Hydroxyphenylethyl alcoholHMDB
b-(4-Hydroxyphenyl)ethanolHMDB
b-(P-Hydroxyphenyl)ethanolHMDB
beta-(4-Hydroxyphenyl)ethanolHMDB
beta-(P-Hydroxyphenyl)ethanolHMDB
P-Hydroxyphenylethyl alcoholHMDB
P-ThyrosolHMDB
P-TyrosolHMDB
Para-hydroxyphenylethanolMeSH
P-HydroxyphenylethanolMeSH
N-TyrosolMeSH
Chemical FormulaC8H10O2
Average Molecular Weight138.1638
Monoisotopic Molecular Weight138.068079564
IUPAC Name4-(2-hydroxyethyl)phenol
Traditional Nametyrosol
CAS Registry Number501-94-0
SMILES
OCCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
InChI KeyYCCILVSKPBXVIP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as tyrosols. These are organic aromatic compounds containing a phenethyl alcohol moiety that carries a hydroxyl group at the 4-position of the benzene group.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
Direct ParentTyrosols
Alternative Parents
Substituents
  • Tyrosol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point90 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility25.3 mg/mLALOGPS
logP0.85ALOGPS
logP1.19ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)10.2ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.61 m3·mol-1ChemAxon
Polarizability14.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-004i-1920000000-4795e885578e89b76024View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-004i-0920000000-09ea62430af3397e5fbbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-004i-0900000000-b6e98d450debce3e52f5View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-004i-1920000000-4795e885578e89b76024View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-004i-0900000000-12207240533c46fdea75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0900000000-49e061bee76cb42ff710View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-f0aacb9c7e251e486554View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fml-9400000000-8e06cbec5e72d3855569View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-b7c90f6632ed711d170cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0900000000-676aa996456f5f0baa94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9800000000-6ea2f536e15d77c65310View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Urine
Tissue Location
  • Prostate
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 673 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 673 details
UrineDetected and Quantified0.0533 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.00200-0.942 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID673
Phenol Explorer Metabolite ID673
FoodDB IDFDB012695
KNApSAcK IDC00029515
Chemspider ID9964
KEGG Compound IDC06044
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTyrosol
NuGOwiki LinkHMDB0004284
METLIN ID7044
PubChem Compound10393
PDB IDNot Available
ChEBI ID1879
References
Synthesis ReferenceZheng, Hong; Gao, Wenfang; Ji, Xueshi; Zhang, Shoufang. Improved method for synthesis of Tyrosol. Zhongguo Yaowu Huaxue Zazhi (2002), 12(3), 166-167.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Quiles JL, Farquharson AJ, Simpson DK, Grant I, Wahle KW: Olive oil phenolics: effects on DNA oxidation and redox enzyme mRNA in prostate cells. Br J Nutr. 2002 Sep;88(3):225-34; discussion 223-4. [PubMed:12207832 ]
  2. Vissers MN, Zock PL, Roodenburg AJ, Leenen R, Katan MB: Olive oil phenols are absorbed in humans. J Nutr. 2002 Mar;132(3):409-17. [PubMed:11880564 ]
  3. Tsarbopoulos A, Gikas E, Papadopoulos N, Aligiannis N, Kafatos A: Simultaneous determination of oleuropein and its metabolites in plasma by high-performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Feb 25;785(1):157-64. [PubMed:12535848 ]
  4. Miles EA, Zoubouli P, Calder PC: Differential anti-inflammatory effects of phenolic compounds from extra virgin olive oil identified in human whole blood cultures. Nutrition. 2005 Mar;21(3):389-94. [PubMed:15797683 ]
  5. Visioli F, Galli C, Bornet F, Mattei A, Patelli R, Galli G, Caruso D: Olive oil phenolics are dose-dependently absorbed in humans. FEBS Lett. 2000 Feb 25;468(2-3):159-60. [PubMed:10692578 ]
  6. Covas MI, Miro-Casas E, Fito M, Farre-Albadalejo M, Gimeno E, Marrugat J, De La Torre R: Bioavailability of tyrosol, an antioxidant phenolic compound present in wine and olive oil, in humans. Drugs Exp Clin Res. 2003;29(5-6):203-6. [PubMed:15134375 ]