HYDROXYTYROSOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H10O3
Molecular Weight	154.1632
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCCC1=CC(O)=C(O)C=C1

InChI

InChIKey=JUUBCHWRXWPFFH-UHFFFAOYSA-N

InChI=1S/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2

HIDE SMILES / InChI

Molecular Formula	C8H10O3
Molecular Weight	154.1632
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29360770 | https://clinicaltrials.gov/ct2/show/NCT02068092 | https://www.ncbi.nlm.nih.gov/pubmed/25620693 | https://www.ncbi.nlm.nih.gov/pubmed/30853597

Hydroxytyrosol is an important phenolic compound obtained from olive oil. Hydroxytyrosol possesses anti-inflammatory properties and has the capacity to inhibit cyclooxygenase and lipoxygenase enzymes. Hydroxytyrosol is a powerful antioxidant due to its protective function in cells. Hydroxytyrosol protects the cardiovascular system, avoiding oxidation of LDL cholesterol, maintaining normal blood HDL cholesterol concentrations and thus preventing atherosclerosis. Hydroxytyrosol protects brain cells from lipid peroxidation because it easy penetrates through the blood-brain barrier. Thus, the compound can be used in the disease treatment of Alzheimer or Parkinson. In addition, the compound also helps to prevent osteoporosis because its consumption has positive effects on the formation and growth of bones. Hydroxytyrosol is under investigation phase II clinical trials for breast cancer women to evaluate its effect on mammographic density. The recently published article has shown hydroxytyrosol could prevent obesity and insulin resistance by altering the composition of the intestinal microbiota and improving the integrity of the intestinal wall.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Arachidonate 5-lipoxygenase 52 Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24568174	Inhibitor 8504		13.0 µM [IC50]

PubMed

Title	Date	PubMed
Diverse effects of natural antioxidants on cyclosporin cytotoxicity in rat renal tubular cells.	2005-08	15855205
Relationships between oxidative stability, triacylglycerol composition, and antioxidant content in olive oil matrices.	2005-07-13	15998146
Fluorescence spectroscopy for monitoring deterioration of extra virgin olive oil during heating.	2005-07	15986208
Kinetic study of the physicochemical and microbiological changes in "seasoned" olives during the shelf-life period.	2005-06-29	15969509
Effect of the conservation procedure on the contents of phenolic compounds and organic acids in chanterelle (Cantharellus cibarius) mushroom.	2005-06-15	15941337
Separation and identification of phenolic compounds in olive oil by coupling high-performance liquid chromatography with postcolumn solid-phase extraction to nuclear magnetic resonance spectroscopy (LC-SPE-NMR).	2005-06-15	15941298
Hydroxytyrosol, a phenolic compound from virgin olive oil, prevents macrophage activation.	2005-06	16025269
Alpha-tocopherol oxidation in fish muscle during chilling and frozen storage.	2005-05-18	15884830
A thromboxane effect of a hydroxytyrosol-rich olive oil wastewater extract in patients with uncomplicated type I diabetes.	2005-05	15798774
Interactions of ferric ions with olive oil phenolic compounds.	2005-04-06	15796614
Hydroxytyrosol, a natural antioxidant from olive oil, prevents protein damage induced by long-wave ultraviolet radiation in melanoma cells.	2005-04-01	15749387
[Studies on chemical constituents from the corm of Cremastra appendiculata].	2005-04	16011094
Secoiridoids, tocopherols, and antioxidant activity of monovarietal extra virgin olive oils extracted from destoned fruits.	2005-02-23	15713026
Antioxidant activity of olive phenols: mechanistic investigation and characterization of oxidation products by mass spectrometry.	2005-02-07	15678179
Activity of olive oil phenols on lymphomonocyte cytosolic calcium.	2005-02	15681170
Radical scavenging potential of phenolic compounds encountered in O. europaea products as indicated by calculation of bond dissociation enthalpy and ionization potential values.	2005-01-26	15656664
Identification and antioxidant potential of flavonoids and low molecular weight phenols in olive cultivar chemlali growing in Tunisia.	2005-01-26	15656655
Antioxidant and anti-atherogenic activities of olive oil phenolics.	2005-01	15830923
Characterization of a new tyrosinase from Pycnoporus species with high potential for food technological applications.	2005	15659188
Phenolic compounds in olive oils intended for refining: formation of 4-ethylphenol during olive paste storage.	2004-12-29	15612814
Olive oil and modulation of cell signaling in disease prevention.	2004-12	15736919
Qualitative and semiquantitative analysis of phenolic compounds in extra virgin olive oils as a function of the ripening degree of olive fruits by different analytical techniques.	2004-11-17	15537313
Antioxidant effect of hydroxytyrosol, a polyphenol from olive oil: scavenging of hydrogen peroxide but not superoxide anion produced by human neutrophils.	2004-11-15	15476671
The toxicity profile of hydrolyzed aqueous olive pulp extract.	2004-11	15573469
Acid-induced structural modifications of unsaturated Fatty acids and phenolic olive oil constituents by nitrite ions: a chemical assessment.	2004-10	15487893
Total recovery of the waste of two-phase olive oil processing: isolation of added-value compounds.	2004-09-22	15366831
[Assessment of the in vitro and in vivo toxicity of 3,4-dihydroxyphenylacetaldehyde (DOPAL)].	2004-09	15314580
Comparative study on phenolic content and antioxidant activity during maturation of the olive cultivar Chemlali from Tunisia.	2004-08-25	15315388
Olives and olive oil in cancer prevention.	2004-08	15554560
Acylated flavonoids and phenol glycosides from Veronica thymoides subsp. pseudocinerea.	2004-08	15381011
Removal of monomeric phenols in dry mill olive residue by saprobic fungi.	2004-07-14	15237956
Production of highly purified hydroxytyrosol from Olea europaea leaf extract biotransformed by hyperthermophilic beta-glycosidase.	2004-07-01	15196771
Low-molecular-weight components of olive oil mill waste-waters.	2004-06-19	15202603
Antifungal constituents of Clytostoma ramentaceum and Mansoa hirsuta.	2004-06	15287070
Effects of differing phenolic content in dietary olive oils on lipids and LDL oxidation--a randomized controlled trial.	2004-06	15168036
Bioavailability and antioxidant effects of olive oil phenols in humans: a review.	2004-06	15164117
Polyphenol changes during fermentation of naturally black olives.	2004-04-07	15053538
Depsides from the petals of Papaver rhoeas.	2004-04	15095160
An endogenous metabolite of dopamine, 3,4-dihydroxyphenylethanol, acts as a unique cytoprotective agent against oxidative stress-induced injury.	2004-03-01	14980700
Toxicity of a treatment associating dopamine and disulfiram for catecholaminergic neuroblastoma SH-SY5Y cells: relationships with 3,4-dihydroxyphenylacetaldehyde formation.	2004-03	15019299
Effect of cultivar and processing method on the contents of polyphenols in table olives.	2004-02-11	14759136
[Isolation and structural identification of C-glycosylflavones from Corallodiscus flabellata].	2004-02	15127617
Toward a high yield recovery of antioxidants and purified hydroxytyrosol from olive mill wastewaters.	2004-01-28	14733507
Biogenic amine formation and "zapatera" spoilage of fermented green olives: effect of storage temperature and debittering process.	2004-01	14717361
Bioavailability of phenolic compounds from olive oil and oxidative/antioxidant status at postprandial state in healthy humans.	2004	15700748
Antioxidant effect of phenolic compounds, alpha-tocopherol, and other minor components in virgin olive oil.	2003-11-19	14611189
3,4-Dihydroxyphenylacetaldehyde is the toxic dopamine metabolite in vivo: implications for Parkinson's disease pathogenesis.	2003-11-07	14556942
Fast separation and determination of tyrosol, hydroxytyrosol and other phenolic compounds in extra-virgin olive oil by capillary zone electrophoresis with ultraviolet-diode array detection.	2003-09-05	14518773
Oxidative transformation of phenols in aqueous mixtures.	2003-07	14509708
In vitro formation of quinoid metabolites of the dietary supplement Cimicifuga racemosa (black cohosh).	2003-07	12870886

Patents

Sample Use Guides

In Vivo Use Guide

Hydroxytyrosol (HT) exert cardioprotective and anti-atherosclerotic effects. This study evaluates the effect of oral supplementation with HT on early atherosclerosis markers in middle-aged, seemingly healthy adults. The supplement was composed of 9.9 mg of HT

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:13:24 GMT 2025` Edited by `admin` on `Mon Mar 31 19:13:24 GMT 2025`
Record UNII	QEU0NE4O90
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HYDROXYTYROSOL [MI]

Preferred Name

English

HYDROXYTYROSOL

Official Name

English

3,4-DIHYDROXYPHENYLETHANOL

Systematic Name

English

4-(2-HYDROXYETHYL)-1,2-BENZENEDIOL

Systematic Name

English

Hydroxytyrosol [WHO-DD]

Common Name

English

3,4-DIHYDROXY-1-BENZENEETHANOL

Systematic Name

English

2-(3,4-DIHYDROXYPHENYL)ETHANOL

Systematic Name

English

HOMOPROTOCATECHUYL ALCOHOL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C275