Names | |
---|---|
Preferred IUPAC name
4-(2-Hydroxyethyl)benzene-1,2-diol | |
Other names
3-Hydroxytyrosol
3,4-dihydroxyphenylethanol (DOPET) Dihydroxyphenylethanol 2-(3,4-Di-hydroxyphenyl)-ethanol (DHPE) 3,4-dihydroxyphenolethanol (3,4-DHPEA) [1] | |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.114.418 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C8H10O3 | |
Molar mass | 154.165 g·mol−1 |
Appearance | colorless solid |
5 g/100 ml | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
|
Causes skin irritation.
Causes serious eye irritation. May cause respiratory irritation. |
GHS labelling: [2] | |
Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Safety data sheet (SDS) | [1] |
Related compounds | |
Related
alcohols
|
benzyl alcohol, tyrosol |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Hydroxytyrosol is an organic compound with the formula (HO)2C6H3CH2CH2OH. It is a phenylethanoid, i.e. a relative of phenethyl alcohol. Its derivatives are found in a variety of natural sources, notably olive oils and wines. Hydroxytyrosol is a colorless solid, [3] [4] although samples often turn beige during storage. It is a derivative, formally speaking, of catechol.
It or its derivatives occurs in olives and in wines [5] [6]
The olives, leaves, and olive pulp contain large amounts of hydroxytyrosol derivative Oleuropein, more so than olive oil. [1] Unprocessed, green (unripe) olives, contain between 4.3 and 116 mg of hydroxytyrosol per 100g of olives, while unprocessed, black (ripe) olives contain up to 413.3 mg per 100g. [7] The ripening of an olive substantially increases the amount of hydroxytyrosol. [8] Processed olives, such as the common canned variety containing iron(II) gluconate, contained little hydroxytyrosol, as iron salts are catalysts for its oxidation. [9]
Hydroxytyrosol is considered safe as a novel food for human consumption, with a no-observed-adverse-effect level of 50 mg/kg body weight per day, as evaluated by the European Food Safety Authority (EFSA). [10]
In the United States, hydroxytyrosol is considered to be a safe ingredient ( GRAS) in processed foods at levels of 5 mg per serving. [11]
In nature, hydroxytyrosol is generated by the hydrolysis of oleuropein that occurs during olive ripening. Oleuropein accumulates in olive leaves and fruit as a defense mechanism against pathogens and herbivores. During olive ripening or when the olive tissue is damaged by pathogens, herbivores, or mechanical damage, the enzyme β-glucosidase catalyzes hydroxytyrosol synthesis via hydrolysis from oleuropein. [12]
Shortly after olive oil consumption, 98% of hydroxytyrosol in plasma and urine appears in conjugated forms (65% glucuronoconjugates), suggesting extensive first-past metabolism and a half-life of 2.43 hours. [13]
Mediterranean diets, characterized by regular intake of olive oil, have been shown to positively affect human health, including reduced rates of cardiovascular diseases. [5] [14] [15] Research on consumption of olive oil and its components includes hydroxytyrosol and oleuropein, which may inhibit oxidation of LDL cholesterol – a risk factor for atherosclerosis, heart attack or stroke. [16] The daily intake of hydroxytyrosol within the Mediterranean diet is estimated to be between 0.15 and 30 mg. [17]
The EFSA has issued a scientific opinion on health claims in relation to dietary consumption of hydroxytyrosol and related polyphenol compounds from olive fruit and oil, and protection of blood lipids from potential oxidative damage. [18]
EFSA concluded that a cause-and-effect relationship existed between the consumption of hydroxytyrosol and related compounds from olives and olive oil and protection of blood lipids from oxidative damage, [18] providing a health claim for consumption of olive oil polyphenols containing at least 5 mg of hydroxytyrosol and its derivatives ( oleuropein complex and tyrosol) per 20 g of olive oil. [19]
From oxidative damage (ID 1333, 1638, 1639, 1696, 2865), maintenance of normal blood HDL cholesterol concentrations (ID 1639), maintenance of normal blood pressure (ID 3781), "anti-inflammatory properties" (ID 1882), "contributes to the upper respiratory tract health" (ID 3468), "can help to maintain a normal function of gastrointestinal tract" (3779), and "contributes to body defences against external agents" (ID 3467) pursuant to Article 13(1) of Regulation (EC) No 1924/2006
Names | |
---|---|
Preferred IUPAC name
4-(2-Hydroxyethyl)benzene-1,2-diol | |
Other names
3-Hydroxytyrosol
3,4-dihydroxyphenylethanol (DOPET) Dihydroxyphenylethanol 2-(3,4-Di-hydroxyphenyl)-ethanol (DHPE) 3,4-dihydroxyphenolethanol (3,4-DHPEA) [1] | |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.114.418 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C8H10O3 | |
Molar mass | 154.165 g·mol−1 |
Appearance | colorless solid |
5 g/100 ml | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
|
Causes skin irritation.
Causes serious eye irritation. May cause respiratory irritation. |
GHS labelling: [2] | |
Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Safety data sheet (SDS) | [1] |
Related compounds | |
Related
alcohols
|
benzyl alcohol, tyrosol |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Hydroxytyrosol is an organic compound with the formula (HO)2C6H3CH2CH2OH. It is a phenylethanoid, i.e. a relative of phenethyl alcohol. Its derivatives are found in a variety of natural sources, notably olive oils and wines. Hydroxytyrosol is a colorless solid, [3] [4] although samples often turn beige during storage. It is a derivative, formally speaking, of catechol.
It or its derivatives occurs in olives and in wines [5] [6]
The olives, leaves, and olive pulp contain large amounts of hydroxytyrosol derivative Oleuropein, more so than olive oil. [1] Unprocessed, green (unripe) olives, contain between 4.3 and 116 mg of hydroxytyrosol per 100g of olives, while unprocessed, black (ripe) olives contain up to 413.3 mg per 100g. [7] The ripening of an olive substantially increases the amount of hydroxytyrosol. [8] Processed olives, such as the common canned variety containing iron(II) gluconate, contained little hydroxytyrosol, as iron salts are catalysts for its oxidation. [9]
Hydroxytyrosol is considered safe as a novel food for human consumption, with a no-observed-adverse-effect level of 50 mg/kg body weight per day, as evaluated by the European Food Safety Authority (EFSA). [10]
In the United States, hydroxytyrosol is considered to be a safe ingredient ( GRAS) in processed foods at levels of 5 mg per serving. [11]
In nature, hydroxytyrosol is generated by the hydrolysis of oleuropein that occurs during olive ripening. Oleuropein accumulates in olive leaves and fruit as a defense mechanism against pathogens and herbivores. During olive ripening or when the olive tissue is damaged by pathogens, herbivores, or mechanical damage, the enzyme β-glucosidase catalyzes hydroxytyrosol synthesis via hydrolysis from oleuropein. [12]
Shortly after olive oil consumption, 98% of hydroxytyrosol in plasma and urine appears in conjugated forms (65% glucuronoconjugates), suggesting extensive first-past metabolism and a half-life of 2.43 hours. [13]
Mediterranean diets, characterized by regular intake of olive oil, have been shown to positively affect human health, including reduced rates of cardiovascular diseases. [5] [14] [15] Research on consumption of olive oil and its components includes hydroxytyrosol and oleuropein, which may inhibit oxidation of LDL cholesterol – a risk factor for atherosclerosis, heart attack or stroke. [16] The daily intake of hydroxytyrosol within the Mediterranean diet is estimated to be between 0.15 and 30 mg. [17]
The EFSA has issued a scientific opinion on health claims in relation to dietary consumption of hydroxytyrosol and related polyphenol compounds from olive fruit and oil, and protection of blood lipids from potential oxidative damage. [18]
EFSA concluded that a cause-and-effect relationship existed between the consumption of hydroxytyrosol and related compounds from olives and olive oil and protection of blood lipids from oxidative damage, [18] providing a health claim for consumption of olive oil polyphenols containing at least 5 mg of hydroxytyrosol and its derivatives ( oleuropein complex and tyrosol) per 20 g of olive oil. [19]
From oxidative damage (ID 1333, 1638, 1639, 1696, 2865), maintenance of normal blood HDL cholesterol concentrations (ID 1639), maintenance of normal blood pressure (ID 3781), "anti-inflammatory properties" (ID 1882), "contributes to the upper respiratory tract health" (ID 3468), "can help to maintain a normal function of gastrointestinal tract" (3779), and "contributes to body defences against external agents" (ID 3467) pursuant to Article 13(1) of Regulation (EC) No 1924/2006