86214-97-3

Upstream product

• 10597-60-1 hydroxytyrosol 
• 108-24-7 acetic anhydride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 75-36-5 acetyl chloride 
• 7417-21-2 2-(3,4-dimethoxyphenyl)ethyl alcohol 
• 220556-03-6 4-(2-bromo-ethyl)-pyrocatechol 
• 18066-68-7 ethyl 3,4-dimethoxyphenylacetate 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 857416-82-1 1,2-diacetoxy-4-(2-bromo-ethyl)-benzene 

Downstream Products

• 69039-02-7 2-(3,4-dihydroxyphenyl)ethyl acetate 
• 10597-60-1 hydroxytyrosol 

Relevant academic research and scientific papers

Production of triacetylhydroxytyrosol from olive mill waste waters for use as stabilized bioantioxidant

A hydroxytyrosol triacetyl derivative was very efficiently produced as a highly pure stabilized antioxidant compound by a short treatment of olive mill waste water (OMWW) organic extracts, rich in hydroxytyrosol, with an acetylating mixture composed of HC

Synthesis and recovery of high bioactive phenolics from table-olive brine process wastewater

The generated wastewater of table-olive brine processing contains a high amount of polyphenols which are endowed with interesting biological activities. The ethyl acetate extract (EAE) of such wastewater shows high hydroxytyrosol (HT) and tyrosol concentrations of 690 and 98 mg g-1 dry weight extract, respectively. Phenolic compounds analysis was performed by gas chromatography-mass spectrometry (GC-MS). The antioxidant activity was evaluated by the scavenging effect on DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS (2,2′-Azinobis[3-ethylbenzothiazoline-6-sulfonate] radicals. Total polyphenol content was estimated with the Folin-Ciocalteu assay. Hydroxytyrosol has DPPH and ABTS radicals scavenging activities higher than 2,6-di-tert-butyl-hydroxytoluene (BHT), while triacetylated hydroxytyrosol (triAcHT) was devoid of any antioxidant activity. The assessment of these antioxidant compounds in biological systems was carried out by the determination of their in vitro cytotoxicity against two different human cancer cell lines (HeLa and DG75) and normal peripheral blood lymphocytes (PBL) using the MTT assay. The 50% cytotoxic concentrations were ranged between 27 and 210 μg mL-1 for Hela and DG75. At the same concentration range, the EAE and the pure HT and triAcHT exhibited an insignificant cytotoxicity against PBL. Incubation of HeLa and DG75 cells with non-cytotoxic concentrations of EAE, HT or triAcHT resulted in a remarkable protection from the oxidative stress induced by Fe2+. The antimicrobial activity evaluated by the broth dilution NCCL method using Gram-positive (Staphylococcus aureus, Bacillus subtilis) and Gram-negative (Pseudomonas aeruginosa, Escherichia coli, Salmonella enterica) bacteria and (Candida albicans, Aspergillus niger) fungi showed a broad spectrum bactericidal and fungicidal effect of table-olives-EAE, HT and triAcHT. The MICs vary from 125 to 500 μg mL-1 for bacteria and from 500 to 2000 μg mL-1 for fungi.

Tunable microwave-assisted method for the solvent-free and catalyst-free peracetylation of natural products

Background: The peracetylation is a simple chemical modification that can be used to enhance the bioavailability of hydrophilic products and to obtain safe and stable pro-drugs. Results: A totally green, solvent-free and catalyst-free microwave (MW)-assisted method for peracetylation of natural products such as oleuropein, alpha-hederin, quercetin and rutin is presented. By simply tuning the MW heating program, polyols with chemical diverse -OH groups or thermolabile functionalities can be peracetylated to improve the biological activity without degradation of the natural starting molecules. An evaluation of the process greenness was performed. Conclusion: The method is potentially universally applicable for green acetylation of hydrophilic biological molecules, potentially easily scalable for industrial applications, including pharmaceutical, cosmetic and food industry.

Synthesis, biological evaluation, and molecular modeling of oleuropein and its semisynthetic derivatives as cyclooxygenase inhibitors

Oleuropein, the main phenolic compound in virgin olive oil, and several of its derivatives such as oleuropein aglycone, hydroxytyrosol, and their respective acetylated lipophilic forms were obtained by simple and environmentally friendly semisynthetic protocols. The same molecules were then tested in vitro and in vivo, comparing their intriguing anti-COX-1 and anti-COX-2 properties to those of well-known anti-inflammatory drugs such as ibuprofen and celecoxib. Finally, molecular modeling experiments displaying the most probable binding modes within the classical binding clefts of the enzymes suggest the heme moiety as a potential alternative target. 2009 American Chemical Society.

Lipid-lowering and antioxidant effects of hydroxytyrosol and its triacetylated derivative recovered from olive tree leaves in cholesterol-fed rats

This study was designed to test the lipid-lowering and antioxidative activities of triacetylated hydroxytyrosol compared with its native compound, hydroxytyrosol, purified from olive tree leaves. Wistar rats fed a standard laboratory diet or a cholesterol-rich diet for 16 weeks were used. The serum lipid levels, the thiobarbituric acid-reactive substances (TBARS) level, as an indicator of lipid peroxidation, and the activity of superoxide dismutase (SOD) as well as that of catalase (CAT) were examined. The cholesterol-rich diet induced hypercholesterolemia that was manifested in the elevation of total cholesterol (TC), triglycerides (TG), and low-density lipoprotein cholesterol (LDL-C). Administration of hydroxytyrosol and triacetylated hydroxytyrosol (3 mg/kg of body weight) decreased the serum levels of TC, TG, and LDL-C significantly and increased the serum level of high-density lipoprotein cholesterol (HDL-C). Furthermore, the content of TBARS in liver, heart, kidney, and aorta decreased significantly when hydroxytyrosol and its triacetylated derivatives were orally administered to rats compared with those fed a cholesterol-rich diet. In addition, triacetylated hydroxytyrosol and hydroxytyrosol increased CAT and SOD activities in the liver. These results suggested that the hypolipidemic effect of triacetylated hydroxytyrosol and hydroxytyrosol might be due to their abilities to lower serum TC, TG, and LDL-C levels as well as to their antioxidant activities preventing the lipid peroxidation process.

Natural compounds and their derivatives for the prevention and treatment of cardiovascular, hepatic and renal diseases and for cosmetic applications

The present invention refers to the use of phenolic compounds and their derivatives represented by formula I wherein R1 and R2 are selected from among: OH, OCOalkyl, or OCOalkenyl, and R3 is either H, OH, OCOalkyl or OCOal

Natural products and derivatives thereof for protection against neurodegenerative diseases

The invention relates to the use of phenolic compounds and derivatives thereof for protection against neurodegenerative diseases, to compositions comprising these compounds, and to some novel phenolic compounds.

A highly convenient synthesis of hydroxytyrosol and its recovery from agricultural waste waters

Hydroxytyrosol, a polyphenol with very interesting antioxidant properties, which naturally occurs in virgin olive oil and mainly in olive oil mill waste waters, was synthesized by reducing 3,4-dihydroxyphenylacetic acid with LiAlH4 in tetrahydrofuran under refluxing for 2 h. The yield of reaction was 82.8%. The spectroscopic and HPLC data of the synthesized compound proved to coincide fully with those of a pure sample obtained by the chromatographic recovery from olive oil mill waste waters (yield = 91 mg/L). This synthetic method appears to be the most convenient compared with those reported in the literature and is more convenient than the chromatographic recovery. The tri- and diacetyl derivatives of the synthetic compound were also prepared for structure-bioactivity relationship studies. A brief discussion is given on the economical and ecological aspects regarding the production of hydroxytyrosol.