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2-(4-Hydroxyphenyl)ethanol (FDB012695)

Record Information
Version1.0
Creation date2010-04-08 22:10:18 UTC
Update date2020-04-21 18:02:29 UTC
Primary IDFDB012695
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-(4-Hydroxyphenyl)ethanol
DescriptionIsolated from peanuts Tyrosol is a phenolic antioxidant present in a variety of natural sources. The principal source in the human diet is olive oil. Tyrosol is a derivative of phenethyl alcohol; Tyrosol 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). 2-(4-Hydroxyphenyl)ethanol is found in many foods, some of which are great horned owl, shiitake, japanese pumpkin, and black crowberry.
CAS Number501-94-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility25.3 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.61 m³·mol⁻¹ChemAxon
Polarizability14.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H10O2
IUPAC name4-(2-hydroxyethyl)phenol
InChI IdentifierInChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
InChI KeyYCCILVSKPBXVIP-UHFFFAOYSA-N
Isomeric SMILESOCCC1=CC=C(O)C=C1
Average Molecular Weight138.1638
Monoisotopic Molecular Weight138.068079564
Classification
Description 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
ClassPhenols
Sub ClassTyrosols and derivatives
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
Foods

Fats and oils:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 69.55%; H 7.29%; O 23.16%DFC
Melting PointMp 85-86°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS2-(4-Hydroxyphenyl)ethanol, 2 TMS, GC-MS Spectrumsplash10-004i-1920000000-4795e885578e89b76024Spectrum
GC-MS2-(4-Hydroxyphenyl)ethanol, non-derivatized, GC-MS Spectrumsplash10-004i-0920000000-09ea62430af3397e5fbbSpectrum
GC-MS2-(4-Hydroxyphenyl)ethanol, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-b6e98d450debce3e52f5Spectrum
GC-MS2-(4-Hydroxyphenyl)ethanol, non-derivatized, GC-MS Spectrumsplash10-004i-1920000000-4795e885578e89b76024Spectrum
GC-MS2-(4-Hydroxyphenyl)ethanol, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-12207240533c46fdea75Spectrum
Predicted GC-MS2-(4-Hydroxyphenyl)ethanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-5900000000-83585cd03b0a8c1b3067Spectrum
Predicted GC-MS2-(4-Hydroxyphenyl)ethanol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00vi-9840000000-6d4093c692b4db8587edSpectrum
Predicted GC-MS2-(4-Hydroxyphenyl)ethanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0900000000-49e061bee76cb42ff7102015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-f0aacb9c7e251e4865542015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fml-9400000000-8e06cbec5e72d38555692015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-b7c90f6632ed711d170c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0900000000-676aa996456f5f0baa942015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9800000000-6ea2f536e15d77c653102015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-752d6f7c286547d7e30b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0900000000-23b0337f09b1b4332c492021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9600000000-d2607175df1bef8971392021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3900000000-45201e48f40748120cd52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fu-9600000000-fc309e7875f3399eb4722021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9000000000-228e273810e98c38c9fc2021-09-23View Spectrum
NMRNot Available
ChemSpider ID9964
ChEMBL IDCHEMBL53566
KEGG Compound IDC06044
Pubchem Compound ID10393
Pubchem Substance IDNot Available
ChEBI ID1879
Phenol-Explorer ID673
DrugBank IDNot Available
HMDB IDHMDB04284
CRC / DFC (Dictionary of Food Compounds) IDHJW29-C:HJW29-C
EAFUS IDNot Available
Dr. Duke IDP-HYDROXYPHENYLETHYLALCOHOL|2-(4-HYDROXY-PHENYL)-ETHANOL|4-HYDROXYPHENYLETHANOL|TYROSOL
BIGG IDNot Available
KNApSAcK IDC00029515
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1203831
SuperScent IDNot Available
Wikipedia IDTyrosol
Phenol-Explorer Metabolite ID673
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
cardiovascular38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).