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Showing Compound tyrosol (FDB031233)

Record Information
Version1.0
Creation date2015-05-07 21:23:06 UTC
Update date2019-11-26 03:22:13 UTC
Primary IDFDB031233
Secondary Accession Numbers
  • FDB012695
Chemical Information
FooDB Nametyrosol
DescriptionTyrosol, also known as 4-hydroxyphenylethanol or 4-(2-hydroxyethyl)phenol, is a member of the class of compounds known as tyrosols. Tyrosols are organic aromatic compounds containing a phenethyl alcohol moiety that carries a hydroxyl group at the 4-position of the benzene group. Tyrosol is soluble (in water) and a very weakly acidic compound (based on its pKa). Tyrosol can be synthesized from 2-phenylethanol. Tyrosol is also a parent compound for other transformation products, including but not limited to, hydroxytyrosol, crosatoside B, and oleocanthal. Tyrosol is a mild, sweet, and floral tasting compound and can be found in a number of food items such as breadnut tree seed, sparkleberry, loquat, and savoy cabbage, which makes tyrosol a potential biomarker for the consumption of these food products. Tyrosol can be found primarily in feces and urine, as well as in human prostate tissue. Tyrosol exists in all eukaryotes, ranging from yeast to humans. Tyrosol present in wine is also shown to be cardioprotective. Samson et al. has shown that tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS and FOXO3a. In addition, tyrosol also induced the expression of longevity protein SIRT1 in the heart after myocardial infarction in a rat MI model. Hence tyrosol's SIRT1, Akt and eNOS activating power adds another dimension to the wine research, because it adds a great link to the French paradox. In conclusion these findings suggest that tyrosol induces myocardial protection against ischemia related stress by inducing survival and longevity proteins that may be considered as anti-aging therapy for the heart .
CAS Number501-94-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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, MeSH
beta-(p-Hydroxyphenyl)ethanolHMDB
P-Hydroxyphenylethyl alcoholHMDB
P-ThyrosolHMDB
p-TyrosolHMDB, MeSH
Para-hydroxyphenylethanolMeSH, HMDB
P-HydroxyphenylethanolMeSH, HMDB
N-TyrosolMeSH, HMDB
2-(4-Hydroxyphenyl)ethyl alcoholHMDB
TyrosolHMDB
p-(2-Hydroxyethyl)phenolHMDB
p-HPEAHMDB
β-(4-Hydroxyphenyl)ethanolHMDB
β-(p-Hydroxyphenyl)ethanolHMDB
2-(3',4'-dihydroxyphenyl)ethanolHMDB
2-(4'-Hydroxyphenyl)ethanolHMDB
4-Hydroxyphenyl alcoholHMDB
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
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
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 IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference