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Human Metabolome Database Version 3.5

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Showing metabocard for Tyrosol (HMDB04284)

Record Information
Version 3.5
Creation Date 2006-08-13 10:05:03 -0600
Update Date 2013-02-08 17:13:09 -0700
HMDB ID HMDB04284
Secondary Accession Numbers None
Metabolite Identification
Common Name Tyrosol
Description 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-(4-Hydroxyphenyl)ethanol
  2. 2-(p-Hydroxyphenyl)ethanol
  3. 4-(2-Hydroxyethyl)phenol
  4. 4-Hydroxybenzeneethanol
  5. 4-Hydroxyphenethyl alcohol
  6. 4-Hydroxyphenylethanol
  7. 4-Hydroxyphenylethyl alcohol
  8. b-(4-Hydroxyphenyl)ethanol
  9. b-(p-Hydroxyphenyl)ethanol
  10. beta-(4-Hydroxyphenyl)ethanol
  11. beta-(p-Hydroxyphenyl)ethanol
  12. p-Hydroxyphenethyl alcohol
  13. p-Hydroxyphenylethyl alcohol
  14. p-Thyrosol
  15. p-Tyrosol
  16. Tyrosol
Chemical Formula C8H10O2
Average Molecular Weight 138.1638
Monoisotopic Molecular Weight 138.068079564
IUPAC Name 4-(2-hydroxyethyl)phenol
Traditional IUPAC Name tyrosol
CAS Registry Number 501-94-0
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 Key YCCILVSKPBXVIP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Tyrosols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • an aromatic compound(Cyc)
  • phenols(ChEBI)
Substituents
  • Primary Alcohol
Direct Parent Tyrosols and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 90 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 25.3 g/L ALOGPS
LogP 0.85 ALOGPS
LogP 1.19 ChemAxon
LogS -0.74 ALOGPS
pKa (strongest acidic) 10.2 ChemAxon
pKa (strongest basic) -2.4 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 40.46 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 39.61 ChemAxon
Polarizability 14.85 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Urine
Tissue Location
  • Prostate
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Expected and not Quantified
Article_icon
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 673 Not Available
Urine Expected and not Quantified
Article_icon
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 673 Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID 673 Link_out
Phenol Explorer Metabolite ID 673 Link_out
FoodDB ID FDB012695
KNApSAcK ID C00029515 Link_out
Chemspider ID 9964 Link_out
KEGG Compound ID C06044 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Tyrosol Link_out
NuGOwiki Link HMDB04284 Link_out
Metagene Link HMDB04284 Link_out
METLIN ID 7044 Link_out
PubChem Compound 10393 Link_out
PDB ID Not Available
ChEBI ID 1879 Link_out
References
Synthesis Reference Zheng, 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. 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 Link_out
  2. 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out