Hydroxytyrosol

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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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.114.418 Edit this at Wikidata
EC Number
  • 600-704-3
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • Oc1ccc(cc1O)CCO
Properties
Chemical formula
 C8H10O3
Molar mass 154.165 g·mol−1
Appearance Clear, faint yellow to yellow liquid
Boiling point 174 °C (345 °F; 447 K)
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 labelling:[2]
Pictograms
 GHS07: Exclamation mark
Signal word
 Warning
H315, H319, H335
Precautionary statements
 P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, 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  (what is checkY☒N ?)
Infobox references

Hydroxytyrosol is a phenylethanoid, a type of phenolic phytochemical with antioxidant properties in vitro. In nature, hydroxytyrosol is mainly found in olives, olive leaves, and olive oil in the form of its elenolic acid ester, oleuropein.[1] It is a constituent of red and white wines.[3]

Description[]

Hydroxytyrosol itself in pure form is a colorless, odorless liquid. But in addition to its pure form, it is more commonly available as a beige colored powder, which is a natural byproduct of the waste water of the olive oil industry. In addition to these natural forms, hydroxytyrosol can also be produced synthetically in varying concentrations as either a pure white powder or as a clear liquid, depending on the concentration. Both the natural and synthetic forms are used in food stuffs and the cosmetics industry.

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.[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.[4] The ripening of an olive substantially increases the amount of hydroxytyrosol.[5] Processed olives, such as the common canned variety containing iron(II) gluconate, contained little hydroxytyrosol, as iron salts are catalysts for its oxidation.[6]

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).[7]

In the United States, hydroxytyrosol is considered to be a safe ingredient (GRAS) in processed foods at levels of 5 mg per serving.[8]

Function and production[]

Synthesis of Hydroxytyrosol.jpg

In nature, hydroxytyrosol is generated by the hydrolysis of oleuropein that occurs during olive ripening. Oleuropein is accumulated 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.[9]

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.[10] 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.[11] The daily intake of hydroxytyrosol within the Mediterranean diet is estimated to be between 0.15 and 30 mg/day.[12]

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.[13]

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,[13] 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.[14]

See also[]

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

References[]

  1. ^ a b c Baldioli M, Servili M, Perretti G, Montedoro GF (1996). "Antioxidant activity of tocopherols and phenolic compounds of virgin olive oil". Journal of the American Oil Chemists' Society. 73 (11): 1589–1593. doi:10.1007/BF02523530. S2CID 84749200.
  2. ^ "Hydroxytyrosol". pubchem.ncbi.nlm.nih.gov.
  3. ^ Fernández-Mar, M.I.; Mateos, R.; García-Parrilla, M.C.; Puertas, B.; Cantos-Villar, E. (2012-02-15). "Bioactive compounds in wine: Resveratrol, hydroxytyrosol and melatonin: A review". Food Chemistry. 130 (4): 797–813. doi:10.1016/j.foodchem.2011.08.023. ISSN 0308-8146.
  4. ^ "Showing all foods in which the polyphenol Hydroxytyrosol is found - Phenol-Explorer". phenol-explorer.eu. Retrieved 2021-07-02.
  5. ^ Rocha, J; Borges, N; Pinho, O (2020). "Table olives and health: a review". Journal of Nutritional Science. 9: e57. doi:10.1017/jns.2020.50. ISSN 2048-6790. PMC 7737178. PMID 33354328.
  6. ^ Marsilio V, Campestre C, Lanza B (July 2001). "Phenolic compounds change during California-style ripe olive processing". Food Chemistry. 74 (1): 55–60. doi:10.1016/S0308-8146(00)00338-1.
  7. ^ Turck, Dominique; Bresson, Jean-Louis; Burlingame, Barbara; Dean, Tara; Fairweather-Tait, Susan; Heinonen, Marina; Hirsch-Ernst, Karen Ildico; Mangelsdorf, Inge; McArdle, Harry J.; Naska, Androniki; Neuhäuser-Berthold, Monika (2017). "Safety of hydroxytyrosol as a novel food pursuant to Regulation (EC) No 258/97". EFSA Journal. 15 (3): e04728. doi:10.2903/j.efsa.2017.4728. ISSN 1831-4732. PMC 7010075. PMID 32625437.
  8. ^ "GRAS notice for hydroxytyrosol". US Food and Drug Administration. 13 May 2016. Retrieved 2 July 2021.
  9. ^ Charoenprasert S, Mitchell A (July 2012). "Factors influencing phenolic compounds in table olives (Olea europaea)". Journal of Agricultural and Food Chemistry. 60 (29): 7081–95. doi:10.1021/jf3017699. PMID 22720792.
  10. ^ Martínez-González Miguel A.; Gea Alfredo; Ruiz-Canela Miguel (2019-03-01). "The Mediterranean diet and cardiovascular health". Circulation Research. 124 (5): 779–798. doi:10.1161/CIRCRESAHA.118.313348. PMID 30817261.
  11. ^ Marcelino, Gabriela; Hiane, Priscila Aiko; Freitas, Karine de Cássia; Santana, Lidiani Figueiredo; Pott, Arnildo; Donadon, Juliana Rodrigues; Guimarães, Rita de Cássia Avellaneda (2019-08-07). "Effects of olive oil and its minor components on cardiovascular diseases, inflammation, and gut microbiota". Nutrients. 11 (8): 1826. doi:10.3390/nu11081826. ISSN 2072-6643. PMC 6722810. PMID 31394805.
  12. ^ de Pablos, Rocío M.; Espinosa-Oliva, Ana María; Hornedo-Ortega, Ruth; Cano, Mercedes; Arguelles, Sandro (1 May 2019). "Hydroxytyrosol protects from aging process via AMPK and autophagy; a review of its effects on cancer, metabolic syndrome, osteoporosis, immune-mediated and neurodegenerative diseases". Pharmacological Research. 143: 58–72. doi:10.1016/j.phrs.2019.03.005. ISSN 1096-1186. PMID 30853597. S2CID 73726654.
  13. ^ a b "Scientific Opinion on the substantiation of health claims related to polyphenols in olive and protection of LDL particles". European Food Safety Authority. 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
  14. ^ "EU Register of nutrition and health claims made on foods (v.3.6)". ec.europa.eu. Retrieved 2021-04-13.
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