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Identification
YMDB IDYMDB01798
NameTyrosol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTyrosol, also known as p-thyrosol, 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. Tyrosol is an extremely weak basic (essentially neutral) compound (based on its pKa). Tyrosol exists in all living species, ranging from bacteria to humans. tyrosol can be biosynthesized from 4-hydroxyphenylacetaldehyde through its interaction with the enzyme alcohol dehydrogenase. In yeast, tyrosol is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
Synonyms
  • 2-(4-Hydroxyphenyl)ethanol
  • 2-(p-Hydroxyphenyl)ethanol
  • 4-(2-Hydroxyethyl)phenol
  • 4-Hydroxybenzeneethanol
  • 4-Hydroxyphenethyl alcohol
  • 4-Hydroxyphenylethanol
  • 4-Hydroxyphenylethyl alcohol
  • b-(4-Hydroxyphenyl)ethanol
  • b-(p-Hydroxyphenyl)ethanol
  • Benzeneethanol, 4-hydroxy-
  • beta-(4-Hydroxyphenyl)ethanol
  • beta-(p-Hydroxyphenyl)ethanol
  • Ethanol, 2-(4-hydroxyphenyl)
  • p-Hydroxy-benzeneethanol
  • p-Hydroxyphenethyl alcohol
  • p-Hydroxyphenylethyl alcohol
  • p-Thyrosol
  • p-Tyrosol
  • Phenethyl alcohol, p-hydroxy-
  • tyrosol [2-(4-hydroxy-phenyl)ethanol]
  • Para-hydroxyphenylethanol
  • N-Tyrosol
  • p-Hydroxyphenylethanol
CAS number501-94-0
WeightAverage: 138.1638
Monoisotopic: 138.068079564
InChI KeyYCCILVSKPBXVIP-UHFFFAOYSA-N
InChIInChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
IUPAC Name4-(2-hydroxyethyl)phenol
Traditional IUPAC Nametyrosol
Chemical FormulaC8H10O2
SMILESOCCC1=CC=C(O)C=C1
Chemical Taxonomy
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
Physical Properties
StateSolid
Charge0
Melting point90 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
FloralFDB012695
FruityFDB012695
MildFDB012695
SweetFDB012695
SMPDB Pathways
Tyrosine metabolismPW002441 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Tyrosine metabolismec00350 Map00350
SMPDB Reactions
4-Hydroxyphenylacetaldehyde + NADH + hydronNAD + Tyrosol
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID1879
HMDB IDHMDB04284
Pubchem Compound ID10393
Kegg IDC06044
ChemSpider ID9964
FOODB IDFDB012695
Wikipedia IDTyrosol
BioCyc IDNot Available

Enzymes

General function:
Involved in zinc ion binding
Specific function:
NADP-dependent alcohol dehydrogenase with a broad substrate specificity
Gene Name:
ADH7
Uniprot ID:
P25377
Molecular weight:
39348.19922
Reactions
An alcohol + NADP(+) → an aldehyde + NADPH.
General function:
Involved in zinc ion binding
Specific function:
NADP-dependent alcohol dehydrogenase with a broad substrate specificity
Gene Name:
ADH6
Uniprot ID:
Q04894
Molecular weight:
39617.30078
Reactions
An alcohol + NADP(+) → an aldehyde + NADPH.