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

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
The effect of tyrosol, hydroxytyrosol and oleuropein on the non-enzymatic lipid peroxidation of rat liver microsomes.	2001 Jan	11269663
Effects of virgin olive oil phenolics on scavenging of reactive nitrogen species and upon nitrergic neurotransmission.	2001 Jul 27	11508353
Changes in the phenolic composition of virgin olive oil from young trees (Olea europaea L. cv. Arbequina) grown under linear irrigation strategies.	2001 Nov	11714351
Comparison of radical scavenging effect, inhibition of microsomal oxygen free radical generation, and serum lipoprotein oxidation of several natural antioxidants.	2002 Apr 10	11929315
Supplementation of plasma with olive oil phenols and extracts: influence on LDL oxidation.	2002 Feb 27	11853520
Antioxidant and other biological activities of phenols from olives and olive oil.	2002 Jan	11746176
Deterioration of natural antioxidant species of vegetable edible oils during the domestic deep-frying and pan-frying of potatoes.	2002 Jul	12090031
Hydroxytyrosol 4-beta-D-glucoside, an important phenolic compound in olive fruits and derived products.	2002 Jun 19	12059168
Biophenols in table olives.	2002 Jun 19	12059143
Partition behavior of virgin olive oil phenolic compounds in oil-brine mixtures during thermal processing for fish canning.	2002 May 8	11982407
Influence of thermal treatments simulating cooking processes on the polyphenol content in virgin olive oil.	2002 Oct 9	12358466
Oxidative transformation of phenols in aqueous mixtures.	2003 Jul	14509708
Activity and location of olive oil phenolic antioxidants in liposomes.	2003 Jun	12787941
Differential effects of quercetin and resveratrol on Band 3 tyrosine phosphorylation signalling of red blood cells.	2003 Jun 6	12763027
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
Acylated flavonoids and phenol glycosides from Veronica thymoides subsp. pseudocinerea.	2004 Aug	15381011
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
Antifungal constituents of Clytostoma ramentaceum and Mansoa hirsuta.	2004 Jun	15287070
An endogenous metabolite of dopamine, 3,4-dihydroxyphenylethanol, acts as a unique cytoprotective agent against oxidative stress-induced injury.	2004 Mar 1	14980700
Acid-induced structural modifications of unsaturated Fatty acids and phenolic olive oil constituents by nitrite ions: a chemical assessment.	2004 Oct	15487893
[Studies on chemical constituents from the corm of Cremastra appendiculata].	2005 Apr	16011094
Hydroxytyrosol, a natural antioxidant from olive oil, prevents protein damage induced by long-wave ultraviolet radiation in melanoma cells.	2005 Apr 1	15749387
Identification and antioxidant potential of flavonoids and low molecular weight phenols in olive cultivar chemlali growing in Tunisia.	2005 Jan 26	15656655

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

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