Chemistry:Hydroxytyrosol

Hydroxytyrosol

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)
Identifiers
CAS Number	10597-60-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:68889 Y
ChEMBL	ChEMBL485747 Y
ChemSpider	74680 Y
DrugBank	DB12771
EC Number	600-704-3
PubChem CID	82755
UNII	QEU0NE4O90 Y
InChI InChI=1S/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2 Y Key: JUUBCHWRXWPFFH-UHFFFAOYSA-N Y InChI=1/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2 Key: JUUBCHWRXWPFFH-UHFFFAOYAM
SMILES Oc1ccc(cc1O)CCO
Properties
Chemical formula	C8H10O3
Molar mass	154.165 g·mol−1
Appearance	colorless solid
Solubility in water	5 g/100 ml
Hazards
Main hazards	Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Safety data sheet	[1]
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
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).
N verify (what is YN ?)
Infobox references

Hydroxytyrosol is an organic compound with the formula (HO)
2C
6H
3CH
2CH
2OH. 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, 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

Occurrence

Olives

thumb|left|[[Oleuropein, bitter compound, an ester of hydroxytyrosol found in green olive skin]]

The olives, leaves, and olive pulp contain large amounts of hydroxytyrosol derivative Oleuropein, more so than olive oil. 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. The ripening of an olive substantially increases the amount of hydroxytyrosol. Processed olives, such as the common canned variety containing iron(II) gluconate, contained little hydroxytyrosol, as iron salts are catalysts for its oxidation.

Food safety

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).

In the United States, hydroxytyrosol is considered to be a safe ingredient (GRAS) in processed foods at levels of 5 mg per serving.

Function and production

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.

Metabolism

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.

Mediterranean diet

Mediterranean diets, characterized by regular intake of olive oil, have been shown to positively affect human health, including reduced rates of cardiovascular diseases. 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. The daily intake of hydroxytyrosol within the Mediterranean diet is estimated to be between 0.15 and 30 mg.

Regulation

Europe

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.

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, 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.

See also

• Echinacoside, a hydroxytyrosol-containing glycoside
• Tyrosol
• Verbascoside, another hydroxytyrosol-containing glycoside
• Resveratrol

References

{{Navbox

| name = Neurotransmitter metabolism intermediates
| title = Neurotransmitter metabolic intermediates
| state = autocollapse|
| listclass = hlist

| group1 = catecholamines
  | list1 = {{Navbox|child

  | group1 = Anabolism
(tyrosine→epinephrine)
  | list1 =

• Tyrosine → Levodopa → [[Chemistry:Dop[[Chemistry:Dopamine → Norepinephrine|Norepinephrine]] → Epinephrine

  | group2 = Catabolism/
metabolites

| list2 =

dopamine:	DOPAL DOPAC MOPET Hydroxytyrosol 3-Methoxytyramine Homovanillic acid
norepinephrine:	3,4-Dihydroxymandelic acid Normetanephrine Vanillylmandelic acid 3-Methoxy-4-hydroxyphenylglycol Dihydroxyphenylethylene glycol
epinephrine:	Metanephrine

}} 

| group3 = tryptophan→serotonin

| list3 =

anabolism:	5-Hydroxytryptophan
catabolism:	5-Hydroxyindoleacetic acid

| group4 = serotonin→melatonin
| list4 =

• Normelatonin

}}