Hydroxytyrosol

Base Information

• Chemical Name: Hydroxytyrosol
• CAS No.: 10597-60-1
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• Hs Code.: 29072990
• UNII: QEU0NE4O90
• DSSTox Substance ID: DTXSID70147451
• Nikkaji Number: J246.008D
• Wikipedia: Hydroxytyrosol
• Wikidata: Q744577
• NCI Thesaurus Code: C63690
• RXCUI: 1314227
• Metabolomics Workbench ID: 38755
• ChEMBL ID: CHEMBL1950045
• Mol file: 10597-60-1.mol

Synonyms:2-(3,4-dihydroxyphenyl)ethanol;3,4-dihydroxyphenylethanol;beta-3,4-dihydroxyphenylethyl alcohol;dopet;hydroxytyrosol

Chemical Property of Hydroxytyrosol

Chemical Property:

• Appearance/Colour: Yellow green powder
• Vapor Pressure: 1.15E-05mmHg at 25°C
• Refractive Index: 1.622
• Boiling Point: 355.4 °C at 760 mmHg
• PKA: 9.72±0.10(Predicted)
• Flash Point: 182.6 °C
• PSA: 60.69000
• Density: 1.321 g/cm³
• LogP: 0.63260
• Storage Temp.: Refrigerator
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly), Ethyl Acetate (Sparingly), Methanol (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 116

Purity/Quality:

20%, 99% ^*data from raw suppliers

Hydroxy Tyrosol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CCO)O)O
• Recent ClinicalTrials: Olive Oil for High Risk Breast Cancer Prevention in Women
• Description: 3,4-Dihydroxyphenyl ethanol is a phenolic component of olive oil that inhibits both 12- and 5-LO. The IC50 values for the inhibition of rat platelet 12-LO and rat neutrophil 5-LO are 4.2 and 13 μM, respectively. It does not inhibit, and may actually enhance, COX activity. 3,4-Dihydroxyphenyl ethanol also protects LDL from both biological and chemical oxidation, suggesting a potential mechanism for the protective effects of olive oil against atherosclerosis.
• Uses: Hydroxytyrosol is used in cardiovascular drugs, and has miraculous effects on the prevention and treatment of arteriosclerosis, hypertension, heart disease, cerebral hemorrhage, etc., and is superior to similar drugs. It can also Inhibits the proliferation rate of cancer cells and induces apoptosis of cancer cells. Hydroxy tyrosol is a tyrosol metabolite. It is also a strong anti-oxidant found in olive oil. It is used in beauty products and health care products, which can effectively enhance skin elasticity and moisturizing, and has the effect of anti-wrinkle and anti-aging.

Technology Process of Hydroxytyrosol

There total 89 articles about Hydroxytyrosol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

homovanillyl alcohol (2380-78-1) → hydroxytyrosol (10597-60-1)

Guidance literature:

With 3-mercaptopropionic acid ethyl ester; In aq. buffer; at 30 ℃; for 24h; pH=6.5; Inert atmosphere; Glovebox; Enzymatic reaction;

DOI:10.1002/anie.202104278

Reference yield: 97.0%

2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)ethan-1-ol (119054-91-0) → hydroxytyrosol (10597-60-1)

Guidance literature:

With Amberlyst 15; In methanol; for 3h; Heating;

DOI:10.1021/jf063353b

Reference yield: 97.0%

2-(3,4-dihydroxyphenyl)acetic acid methyl ester (25379-88-8) → hydroxytyrosol (10597-60-1)

Guidance literature:

2-(3,4-dihydroxyphenyl)acetic acid methyl ester; With sodium tetrahydroborate; In water; at 0 - 24.5 ℃; for 8.16667h;

With hydrogenchloride; water; at 0 - 5 ℃; for 0.25h; Product distribution / selectivity;

upstream raw materials:

methanol

2′-acetylacteoside

2'-acetylisoacteoside

2-(3,4-dihydroxyphenyl)-ethyl O-α-L-rhamnopyranosyl-(1->3)-O-[β-D-clucopyranosyl-(1->6)]-2-O-acetyl-4-O-[(E)-caffeoyl]-β-D-glucopyranoside

Downstream raw materials:

6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline-2,3,9,10-tetraol

6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline-2,3,10,11-tetraol

2-(3,4-diacetoxyphenyl)-ethyl acetate

Refernces

• 1、 Allouche, Noureddine,Sayadi, Sami. "Synthesis of hydroxytyrosol, 2-hydroxyphenylacetic acid, and 3-hydroxyphenylacetic acid by differential conversion of tyrosol isomers using Serratia marcescens strain". . p. 6525 - 6530. Retrieved 2005.
• 2、 Grasso, Salvatore,Siracusa, Laura,Spatafora, Carmela,Renis, Marcella,Tringali, Corrado. "Hydroxytyrosol lipophilic analogues: Enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection". . p. 137 - 152. Retrieved 2007.
• 3、 Mateos, Raquel,Espartero, Jose Luis,Trujillo, Mariana,Rios,Leon-Camacho, Manuel,Alcudia, Felipe,Cert, Arturo. "Determination of phenols, flavones, and lignans in virgin olive oils by solid-phase extraction and high-performance liquid chromatography with diode array ultraviolet detection". . p. 2185 - 2192. Retrieved 2001.
• 4、 Bernini, Roberta,Crisante, Fernanda,D'Acunzo, Francesca,Gentili, Patrizia,Ussia, Emanuele. "Oxidative cleavage of 1-aryl-isochroman derivatives using the: Trametes villosa laccase/1-hydroxybenzotriazole system". . p. 3314 - 3322. Retrieved 2016.
• 5、 Horvat, Melissa,Fritsche, Susanne,Kourist, Robert,Winkler, Margit. "Characterization of Type IV Carboxylate Reductases (CARs) for Whole Cell-Mediated Preparation of 3-Hydroxytyrosol". . p. 4171 - 4181. Retrieved 2019.
• 6、 Medina,Lois,Alcantara,Lucas,Morales. "Effect of lipophilization of hydroxytyrosol on its antioxidant activity in fish oils and fish oil-in-water emulsions". . p. 9773 - 9779. Retrieved 2009.
• 7、 Medina, Eduardo,Brenes, Manuel,Romero, Concepcion,Garcia, Aranzazu,De Castro, Antonio. "Main antimicrobial compounds in table olives". . p. 9817 - 9823. Retrieved 2007.
• 8、 Espin, Juan Carlos,Soler-Rivas, Cristina,Cantos, Emma,Tomas-Barberan, Francisco A.,Wichers, Harry J.. "Synthesis of the antioxidant hydroxytyrosol using tyrosinase as biocatalyst". . p. 1187 - 1193. Retrieved 2001.
• 9、 Gvazava,Kikoladze. "Verbascoside from Verbascum phlomoides". . p. 710 - 711. Retrieved 2007.
• 10、 Fernandez-Pastor, Ignacio,Fernandez-Hernandez, Antonia,Rivas, Francisco,Martinez, Antonio,Garcia-Granados, Andres,Parra, Andres. "Synthesis and Antioxidant Activity of Hydroxytyrosol Alkyl-Carbonate Derivatives". . p. 1737 - 1745. Retrieved 2016.