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 49 Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24568174	Inhibitor 8297		13.0 µM [IC50]

PubMed

Title	Date	PubMed
Antioxidant effect of hydroxytyrosol (DPE) and Mn2+ in liver of cadmium-intoxicated rats.	2002 Dec	12458190
Antioxidants induce different phenotypes by a distinct modulation of signal transduction.	2002 Dec 18	12482581
Bioactive compounds in foods: their role in the prevention of cardiovascular disease and cancer.	2002 Dec 30	12566142
Radioprotective effects in vivo of phenolics extracted from Olea europaea L. leaves against X-ray-induced chromosomal damage: comparative study versus several flavonoids and sulfur-containing compounds.	2002 Fall	12495584
Phenolic compounds profile of cornicabra virgin olive oil.	2002 Nov 6	12405780
Production in large quantities of highly purified hydroxytyrosol from liquid-solid waste of two-phase olive oil processing or "Alperujo".	2002 Nov 6	12405779
Influence of thermal treatments simulating cooking processes on the polyphenol content in virgin olive oil.	2002 Oct 9	12358466
Olive oil phenolics: effects on DNA oxidation and redox enzyme mRNA in prostate cells.	2002 Sep	12207832
Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: antiatherogenic properties of Mediterranean diet phytochemicals.	2003 Apr 1	12615669
Quantitative changes in phenolic content during physiological development of the olive (Olea europaea) cultivar Hardy's Mammoth.	2003 Apr 23	12696932
Environmental effects caused by olive mill wastewaters: toxicity comparison of low-molecular-weight phenol components.	2003 Feb 12	12568563
Simultaneous determination of oleuropein and hydroxytyrosol in rat plasma using liquid chromatography with fluorescence detection.	2003 Feb 25	12535851
Simultaneous determination of oleuropein and its metabolites in plasma by high-performance liquid chromatography.	2003 Feb 25	12535848
Liquid chromatography-tandem mass spectrometry analysis of oleuropein and its metabolite hydroxytyrosol in rat plasma and urine after oral administration.	2003 Feb 25	12535837
Tyrosol and hydroxytyrosol are absorbed from moderate and sustained doses of virgin olive oil in humans.	2003 Jan	12548315
Changes in phenolic composition and antioxidant activity of virgin olive oil during frying.	2003 Jan 29	12537439
Oxidative transformation of phenols in aqueous mixtures.	2003 Jul	14509708
In vitro formation of quinoid metabolites of the dietary supplement Cimicifuga racemosa (black cohosh).	2003 Jul	12870886
Activity and location of olive oil phenolic antioxidants in liposomes.	2003 Jun	12787941
Hydroxytyrosol disposition in humans.	2003 Jun	12765992
Differential effects of quercetin and resveratrol on Band 3 tyrosine phosphorylation signalling of red blood cells.	2003 Jun 6	12763027
Grape and grape seed extract capacities at protecting LDL against oxidation generated by Cu2+, AAPH or SIN-1 and at decreasing superoxide THP-1 cell production. A comparison to other extracts or compounds.	2003 May	12797479
Isolation, structure elucidation and antioxidant potential of the major phenolic and flavonoid compounds in brined olive drupes.	2003 May	12659724
Antioxidant effect of phenolic compounds, alpha-tocopherol, and other minor components in virgin olive oil.	2003 Nov 19	14611189
3,4-Dihydroxyphenylacetaldehyde is the toxic dopamine metabolite in vivo: implications for Parkinson's disease pathogenesis.	2003 Nov 7	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 Sep 5	14518773
Bioavailability of phenolic compounds from olive oil and oxidative/antioxidant status at postprandial state in healthy humans.	2004	15700748
Depsides from the petals of Papaver rhoeas.	2004 Apr	15095160
Polyphenol changes during fermentation of naturally black olives.	2004 Apr 7	15053538
Olives and olive oil in cancer prevention.	2004 Aug	15554560
[Isolation and structural identification of C-glycosylflavones from Corallodiscus flabellata].	2004 Feb	15127617
Effect of cultivar and processing method on the contents of polyphenols in table olives.	2004 Feb 11	14759136
Biogenic amine formation and "zapatera" spoilage of fermented green olives: effect of storage temperature and debittering process.	2004 Jan	14717361
Toward a high yield recovery of antioxidants and purified hydroxytyrosol from olive mill wastewaters.	2004 Jan 28	14733507
Production of highly purified hydroxytyrosol from Olea europaea leaf extract biotransformed by hyperthermophilic beta-glycosidase.	2004 Jul 1	15196771
Removal of monomeric phenols in dry mill olive residue by saprobic fungi.	2004 Jul 14	15237956
Antifungal constituents of Clytostoma ramentaceum and Mansoa hirsuta.	2004 Jun	15287070
Effects of differing phenolic content in dietary olive oils on lipids and LDL oxidation--a randomized controlled trial.	2004 Jun	15168036
Bioavailability and antioxidant effects of olive oil phenols in humans: a review.	2004 Jun	15164117
Toxicity of a treatment associating dopamine and disulfiram for catecholaminergic neuroblastoma SH-SY5Y cells: relationships with 3,4-dihydroxyphenylacetaldehyde formation.	2004 Mar	15019299
An endogenous metabolite of dopamine, 3,4-dihydroxyphenylethanol, acts as a unique cytoprotective agent against oxidative stress-induced injury.	2004 Mar 1	14980700
Low-molecular-weight components of olive oil mill waste-waters.	2004 May-Jun	15202603
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 Nov 17	15537313
Acid-induced structural modifications of unsaturated Fatty acids and phenolic olive oil constituents by nitrite ions: a chemical assessment.	2004 Oct	15487893
Total recovery of the waste of two-phase olive oil processing: isolation of added-value compounds.	2004 Sep 22	15366831
Characterization of a new tyrosinase from Pycnoporus species with high potential for food technological applications.	2005	15659188
[Studies on chemical constituents from the corm of Cremastra appendiculata].	2005 Apr	16011094
Activity of olive oil phenols on lymphomonocyte cytosolic calcium.	2005 Feb	15681170
Identification and antioxidant potential of flavonoids and low molecular weight phenols in olive cultivar chemlali growing in Tunisia.	2005 Jan 26	15656655
Hydroxytyrosol, a phenolic compound from virgin olive oil, prevents macrophage activation.	2005 Jun	16025269

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 `Fri Dec 15 18:29:23 GMT 2023` Edited by `admin` on `Fri Dec 15 18:29:23 GMT 2023`
Record UNII	QEU0NE4O90
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HYDROXYTYROSOL

Official Name

English

HYDROXYTYROSOL [MI]

Common 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

HYDROXYTYROSOL [INCI]

Common Name

English

HOMOPROTOCATECHUYL ALCOHOL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C275