Hydroxytyrosol
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| Names | |
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| IUPAC name
4-(2-Hydroxyethyl)-1,2-benzenediol
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| Other names
3-Hydroxytyrosol
3,4-dihydroxyphenylethanol (DOPET) Dihydroxyphenylethanol 2-(3,4-Di-hydroxyphenyl)-ethanol (DHPE) 3,4-dihydroxyphenolethanol (3,4-DHPEA)[1] |
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| Identifiers | |
10597-60-1  |
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| ChEBI | CHEBI:68889  |
| ChEMBL | ChEMBL485747 |
| ChemSpider | 74680 |
| Jmol 3D model | Interactive image |
| PubChem | 82755 |
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| Properties | |
| C8H10O3 | |
| Molar mass | 154.163193 g/mol |
| Appearance | Clear, faint yellow to yellow liquid |
| Boiling point | 174 °C (345 °F; 447 K) |
| 5 g/100 ml (25 °C) | |
| Vapor pressure | {{{value}}} |
| Related compounds | |
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Related alcohols
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ethanol, phenol, tyrosol |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
Hydroxytyrosol is a phenylethanoid, a type of phenolic phytochemical with antioxidant properties in vitro. In nature, hydroxytyrosol is found in olive leaf and olive oil, in the form of its elenolic acid ester oleuropein and, especially after degradation, in its plain form.
Oleuropein, along with oleocanthal, are responsible for the bitter taste of extra virgin olive oil. Hydroxytyrosol itself in pure form is a colorless, odorless liquid. The olives, leaves and olive pulp contain large amounts of hydroxytyrosol (compared to olive oil), most of which can be recovered to produce hydroxytyrosol extracts. However, it was found that black olives, such as common canned variety, containing iron(II) gluconate contained very little of the original hydroxytyrosol, as iron salts are catalysts for its oxidation.[2]
Hydroxytyrosol can also be produced endogenously as it is a product of dopamine oxidative metabolism known as DOPET (3,4-dihydroxyphenylethanol).[3][4]
Contents
Research into potential health effects
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In vitro studies
An olive oil fraction containing hydroxytyrosol can inhibit platelet aggregation and eicosanoid (thromboxane B2) formation in vitro.[5] In basic research, hydroxytyrosol had evidence for antimicrobial and antibiotic properties.[6][7]
In vivo studies
Studies have shown that a low dose of hydroxytyrosol reduces the consequences of sidestream smoke-induced oxidative stress in rats.[8]
Ex vivo data provide the first evidence of possible neuroprotective effects of oral hydroxytyrosol intake. Both ex vivo and in vitro studies identified mitochondria as one target for hydroxytyrosol effects in the brain.[9][10]
Metabolism
Hydroxytyrosol undergoes phase II metabolism reactions. The enzymes implicated in these reactions are 5'-diphosphoglucuronosyl transferases (UGTs), sulfotransferases (SULT), and catechol-O-methyltransferase (COMT). The major HT metabolites described in humans are 3- and 4-O-glucuronide conjugates, as well as the corresponding sulfates. A minor metabolic pathway is the COMT-catalyzed conversion of hydroxytyrosol into homovanillyl alcohol.[3]
See also
- Tyrosol
- Echinacoside, a hydroxytyrosol-containing glycoside
References
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