Hydroxytyrosol

Source: Wikipedia, the free encyclopedia.
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)[1]
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
100.114.418 Edit this at Wikidata
EC Number
  • 600-704-3
UNII
  • InChI=1S/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2 checkY
    Key: JUUBCHWRXWPFFH-UHFFFAOYSA-N checkY
  • 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
  • Oc1ccc(cc1O)CCO
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]
GHS07: Exclamation mark
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).
☒N verify (what is checkY☒N ?)

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]

Occurrence

Olives

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.[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]

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).[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]

Function and production

In nature, hydroxytyrosol is generated by the

β-glucosidase catalyzes hydroxytyrosol synthesis via hydrolysis from oleuropein.[12]

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.[13]

Mediterranean diet

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]

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.[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]

See also

References

  1. ^
    S2CID 84749200
    .
  2. ^ "Hydroxytyrosol". PubChem. U.S. National Library of Medicine.
  3. PMID 22720792
    .
  4. .
  5. ^ .
  6. .
  7. ^ "Showing all foods in which the polyphenol Hydroxytyrosol is found - Phenol-Explorer". phenol-explorer.eu. Retrieved 2021-07-02.
  8. PMID 33354328
    .
  9. .
  10. .
  11. ^ "GRAS notice for hydroxytyrosol". US Food and Drug Administration. 13 May 2016. Retrieved 2 July 2021.
  12. PMID 22720792
    .
  13. .
  14. .
  15. .
  16. .
  17. .
  18. ^ a b "Scientific Opinion on the substantiation of health claims related to polyphenols in olive and protection of LDL particles". European Food Safety Authority. 8 April 2011. Retrieved 2021-04-13. 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
  19. ^ "EU Register of nutrition and health claims made on foods (v.3.6)". ec.europa.eu. Retrieved 2021-04-13.