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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-01-22 12:36:42 UTC
Update Date2020-11-09 23:17:44 UTC
HMDB IDHMDB0005784
Secondary Accession Numbers
  • HMDB05784
Metabolite Identification
Common NameHydroxytyrosol
DescriptionHydroxytyrosol, also known as dopet, 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. Hydroxytyrosol is found, on average, in the highest concentration within olives (Olea europaea) and grape wine. Hydroxytyrosol has also been detected, but not quantified in, several different foods, such as cloves (Syzygium aromaticum), fruits, olive oil, and rapes (Brassica napus var. napus). This could make hydroxytyrosol a potential biomarker for the consumption of these foods. Hydroxytyrosol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Hydroxytyrosol.
Structure
Data?1582752364
Synonyms
ValueSource
3,4-DihydroxyphenylethanolChEBI
DopetChEBI
2-(3,4-Dihydroxyphenyl)ethanolMeSH
beta-3,4-Dihydroxyphenylethyl alcoholMeSH
3-HydroxytyrosolHMDB
4-(2-Hydroxyethyl)-1,2-benzenediolHMDB
2-(3'-hydroxyphenyl)ethanolHMDB
2-(3-hydroxyphenyl)ethanolHMDB
2-(3',4'-Dihydroxyphenyl)ethanolHMDB
2-(3,4-Hydroxyphenyl)ethanolHMDB
3'-HydroxytyrosolHMDB
3,4-Dihydroxyphenethyl alcoholHMDB
Homoprotocatechuyl 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
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
  • 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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available131.78731661259
DarkChem[M-H]-PredictedNot Available129.90531661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Hydroxytyrosol,1TMS,#11768.8112https://arxiv.org/abs/1905.12712
Hydroxytyrosol,1TMS,#21655.7233https://arxiv.org/abs/1905.12712
Hydroxytyrosol,1TMS,#31660.2313https://arxiv.org/abs/1905.12712
Hydroxytyrosol,2TMS,#11703.0729https://arxiv.org/abs/1905.12712
Hydroxytyrosol,2TMS,#21696.3245https://arxiv.org/abs/1905.12712
Hydroxytyrosol,2TMS,#31693.7894https://arxiv.org/abs/1905.12712
Hydroxytyrosol,3TMS,#11741.4027https://arxiv.org/abs/1905.12712
Hydroxytyrosol,1TBDMS,#11973.5433https://arxiv.org/abs/1905.12712
Hydroxytyrosol,1TBDMS,#21904.4939https://arxiv.org/abs/1905.12712
Hydroxytyrosol,1TBDMS,#31899.9036https://arxiv.org/abs/1905.12712
Hydroxytyrosol,2TBDMS,#12176.7935https://arxiv.org/abs/1905.12712
Hydroxytyrosol,2TBDMS,#22165.155https://arxiv.org/abs/1905.12712
Hydroxytyrosol,2TBDMS,#32176.6116https://arxiv.org/abs/1905.12712
Hydroxytyrosol,3TBDMS,#12419.198https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-2900000000-8d596359f3e8b95f4fa72017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0avi-8194000000-1246fe8fdd02629c75a62017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-a1441b9d84728fafbb092016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-1900000000-fb3b6c0cad97ea8833c92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-102i-9500000000-6b10b75df8f0b9e05c362016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-eedf780d36ff3efc3d4a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-1900000000-0a567eded9b9beab7d872016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-7900000000-7f6f49833d505eb07a7f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-ee9e9b8403f62cfc7fdf2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-37557f00ee289c910aae2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4900000000-4f2e2d4e2b43d505841d2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-49cbe0a256086ac73ab62021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-1900000000-89117076f87a6733280c2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-300510e1926eff1f33362021-09-07View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.16 +/- 0.084 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
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 674 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 674 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 674 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB12771
Phenol Explorer Compound ID1051
FooDB IDFDB008754
KNApSAcK IDC00032635
Chemspider ID74680
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHydroxytyrosol
METLIN IDNot Available
PubChem Compound82755
PDB IDNot Available
ChEBI ID68889
Food Biomarker OntologyNot Available
VMH ID34DHPE
MarkerDB IDNot Available
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 ]
  3. Satoh Y, Tajima K, Munekata M, Keasling JD, Lee TS: Engineering of L-tyrosine oxidation in Escherichia coli and microbial production of hydroxytyrosol. Metab Eng. 2012 Nov;14(6):603-10. doi: 10.1016/j.ymben.2012.08.002. Epub 2012 Aug 29. [PubMed:22948011 ]