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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 16:05:03 UTC
Update Date2021-10-13 04:43:32 UTC
HMDB IDHMDB0004284
Secondary Accession Numbers
  • HMDB04284
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 ). Tyrosol is a microbial metabolite found in Bifidobacterium, Escherichia and Lactobacillus (PMID:28393285 ).
Structure
Data?1588003978
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, 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
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
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
Physiological effect
Disposition
Biological locationSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point90 °CNot Available
Boiling Point308.00 to 311.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility123800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.851 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker138.70830932474
[M-H]-Not Available138.708http://allccs.zhulab.cn/database/detail?ID=AllCCS00001919
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.59631661259
DarkChem[M-H]-124.9131661259
DeepCCS[M+H]+129.43730932474
DeepCCS[M-H]-125.63130932474
DeepCCS[M-2H]-163.03130932474
DeepCCS[M+Na]+138.29530932474
AllCCS[M+H]+129.632859911
AllCCS[M+H-H2O]+125.032859911
AllCCS[M+NH4]+133.932859911
AllCCS[M+Na]+135.232859911
AllCCS[M-H]-129.132859911
AllCCS[M+Na-2H]-130.732859911
AllCCS[M+HCOO]-132.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TyrosolOCCC1=CC=C(O)C=C12780.2Standard polar33892256
TyrosolOCCC1=CC=C(O)C=C11452.6Standard non polar33892256
TyrosolOCCC1=CC=C(O)C=C11443.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tyrosol,1TMS,isomer #1C[Si](C)(C)OCCC1=CC=C(O)C=C11554.9Semi standard non polar33892256
Tyrosol,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(CCO)C=C11489.7Semi standard non polar33892256
Tyrosol,2TMS,isomer #1C[Si](C)(C)OCCC1=CC=C(O[Si](C)(C)C)C=C11567.4Semi standard non polar33892256
Tyrosol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC1=CC=C(O)C=C11779.3Semi standard non polar33892256
Tyrosol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CCO)C=C11741.7Semi standard non polar33892256
Tyrosol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12028.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tyrosol GC-MS (2 TMS)splash10-004i-1920000000-4795e885578e89b760242014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyrosol EI-B (Non-derivatized)splash10-004i-0920000000-09ea62430af3397e5fbb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyrosol GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-b6e98d450debce3e52f52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyrosol GC-MS (Non-derivatized)splash10-004i-1920000000-4795e885578e89b760242017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyrosol GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-12207240533c46fdea752017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tyrosol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-5900000000-83585cd03b0a8c1b30672016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tyrosol GC-MS (2 TMS) - 70eV, Positivesplash10-00vi-9840000000-6d4093c692b4db8587ed2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tyrosol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 10V, Positive-QTOFsplash10-00dr-0900000000-49e061bee76cb42ff7102015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 20V, Positive-QTOFsplash10-00di-1900000000-f0aacb9c7e251e4865542015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 40V, Positive-QTOFsplash10-0fml-9400000000-8e06cbec5e72d38555692015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 10V, Negative-QTOFsplash10-000i-0900000000-b7c90f6632ed711d170c2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 20V, Negative-QTOFsplash10-0a4r-0900000000-676aa996456f5f0baa942015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 40V, Negative-QTOFsplash10-05mo-9800000000-6ea2f536e15d77c653102015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 10V, Negative-QTOFsplash10-000i-0900000000-752d6f7c286547d7e30b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 20V, Negative-QTOFsplash10-066r-0900000000-23b0337f09b1b4332c492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 40V, Negative-QTOFsplash10-00kf-9600000000-d2607175df1bef8971392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 10V, Positive-QTOFsplash10-00di-3900000000-45201e48f40748120cd52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 20V, Positive-QTOFsplash10-00fu-9600000000-fc309e7875f3399eb4722021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tyrosol 40V, Positive-QTOFsplash10-004l-9000000000-228e273810e98c38c9fc2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 673 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID673
FooDB IDFDB012695
KNApSAcK IDC00029515
Chemspider ID9964
KEGG Compound IDC06044
BioCyc IDCPD3O-4151
BiGG IDNot Available
Wikipedia LinkTyrosol
METLIN ID7044
PubChem Compound10393
PDB IDNot Available
ChEBI ID1879
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1203831
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 ]
  7. Rowland I, Gibson G, Heinken A, Scott K, Swann J, Thiele I, Tuohy K: Gut microbiota functions: metabolism of nutrients and other food components. Eur J Nutr. 2018 Feb;57(1):1-24. doi: 10.1007/s00394-017-1445-8. Epub 2017 Apr 9. [PubMed:28393285 ]

Enzymes

General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Tyrosol → Tyrosol 4-sulfatedetails