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Record Information
Version4.0
Creation Date2007-01-22 12:36:42 UTC
Update Date2017-09-27 08:24:38 UTC
HMDB IDHMDB0005784
Secondary Accession Numbers
  • HMDB05784
Metabolite Identification
Common NameHydroxytyrosol
DescriptionHydroxytyrosol is a polyphenol extracted from virgin olive oil and a natural antioxidant. It has a protective effect in preventing protein damage induced by ultraviolet radiation (PMID: 15749387 ). Research results suggest that Hydroxytyrosol could exert its antioxidant effect by scavenging hydrogen peroxide but not superoxide anion released during the respiratory burst(PMID: 15476671 ).
Structure
Thumb
Synonyms
ValueSource
3,4-DihydroxyphenylethanolChEBI
DopetChEBI
2-(3,4-Dihydroxyphenyl)ethanolHMDB
3-HydroxytyrosolHMDB
4-(2-Hydroxyethyl)-1,2-benzenediolHMDB
beta-3,4-Dihydroxyphenylethyl alcoholHMDB
Chemical FormulaC8H10O3
Average Molecular Weight154.1632
Monoisotopic Molecular Weight154.062994186
IUPAC Name4-(2-hydroxyethyl)benzene-1,2-diol
Traditional Namehydroxytyrosol
CAS Registry Number10597-60-1
SMILES
OCCC1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2
InChI KeyJUUBCHWRXWPFFH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
Direct ParentTyrosols
Alternative Parents
Substituents
  • Tyrosol
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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

Biological Location:

  Biofluid and excreta:

Source:

  Biological:

    Plant:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility17.4 g/LALOGPS
logP0.13ALOGPS
logP0.89ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.59 m³·mol⁻¹ChemAxon
Polarizability15.74 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.16 +/- 0.084 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 674 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 674 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 674 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 674 details
UrineDetected and Quantified0.163 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0230-5.850 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0543 umol/mmol creatinineAdult (>18 years old)Female
High risk of coronary artery disease
details
UrineDetected and Quantified0.0924 umol/mmol creatinineAdult (>18 years old)Male
High risk of coronary artery disease
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID1051
Phenol Explorer Metabolite ID674
FoodDB IDFDB008754
KNApSAcK IDC00032635
Chemspider ID74680
KEGG Compound IDNot Available
BioCyc IDCPD-15887
BiGG IDNot Available
Wikipedia LinkHydroxytyrosol
METLIN IDNot Available
PubChem Compound82755
PDB IDNot Available
ChEBI ID68889
References
Synthesis ReferenceVoswinckel, Hugo. Derivatives of Pyrocatechol. Berichte der Deutschen Chemischen Gesellschaft (1910), 42 4651-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. O'Dowd Y, Driss F, Dang PM, Elbim C, Gougerot-Pocidalo MA, Pasquier C, El-Benna J: Antioxidant effect of hydroxytyrosol, a polyphenol from olive oil: scavenging of hydrogen peroxide but not superoxide anion produced by human neutrophils. Biochem Pharmacol. 2004 Nov 15;68(10):2003-8. [PubMed:15476671 ]
  2. D'Angelo S, Ingrosso D, Migliardi V, Sorrentino A, Donnarumma G, Baroni A, Masella L, Tufano MA, Zappia M, Galletti P: Hydroxytyrosol, a natural antioxidant from olive oil, prevents protein damage induced by long-wave ultraviolet radiation in melanoma cells. Free Radic Biol Med. 2005 Apr 1;38(7):908-19. [PubMed:15749387 ]