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Record Information
Version3.6
Creation Date2006-08-13 16:05:03 UTC
Update Date2016-02-11 01:06:42 UTC
HMDB IDHMDB04284
Secondary Accession NumbersNone
Metabolite Identification
Common NameTyrosol
DescriptionTyrosol is a phenolic compound present in two of the traditional components of the Mediterranean diet: wine and virgin olive oil. The presence of tyrosol has been described in red and white wines. Tyrosol is also present in vermouth and beer. Tyrosol has been shown to be able to exert antioxidant activity in vitro studies. Oxidation of low-density lipoprotein (LDL) appears to occur predominantly in arterial intimae in microdomains sequestered from antioxidants of plasma. The antioxidant content of the LDL particle is critical for its protection. The ability of tyrosol to bind human LDL has been reported. The bioavailability of tyrosol in humans from virgin olive oil in its natural form has been demonstrated. Urinary tyrosol increases, reaching a peak at 0-4 h after virgin olive oil administration. Men and women show a different pattern of urinary excretion of tyrosol. Moreover, tyrosol is absorbed in a dose-dependent manner after sustained and moderate doses of virgin olive oil. Tyrosol from wine or virgin olive oil could exert beneficial effects on human health in vivo if its biological properties are confirmed. (PMID 15134375 ).
Structure
Thumb
Synonyms
ValueSource
4-HydroxybenzeneethanolChEBI
4-HydroxyphenylethanolChEBI
P-Hydroxyphenethyl alcoholChEBI
TyrosolChEBI
2-(4-Hydroxyphenyl)ethanolHMDB
2-(P-Hydroxyphenyl)ethanolHMDB
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
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 KeyInChIKey=YCCILVSKPBXVIP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentTyrosols
Alternative Parents
Substituents
  • Tyrosol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Urine
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 673
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 673
  • Not Applicable
details
Abnormal Concentrations
Not Available
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 LinkHMDB04284
Metagene LinkHMDB04284
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. [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. [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. [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. [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. [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. [15134375 ]