69039-02-7

Usage

Uses

Used in Food Industry:
Hydroxytyrosol Acetate is used as a natural antioxidant for enhancing the shelf life and quality of various food products. Its antioxidant properties help in neutralizing free radicals, thus preventing the oxidation of fats and oils, and maintaining the freshness and taste of the food.
Used in Pharmaceutical Industry:
Hydroxytyrosol Acetate is used as a therapeutic agent for its potential health benefits. It has been found to possess anti-inflammatory, anti-cancer, and neuroprotective properties. Its antioxidant activity also makes it a promising candidate for the treatment of various diseases associated with oxidative stress.
Used in Cosmetic Industry:
Hydroxytyrosol Acetate is used as an active ingredient in cosmetic products for its skin-friendly properties. It helps in protecting the skin from oxidative damage, promoting skin health, and delaying the signs of aging. Its antioxidant and anti-inflammatory properties also contribute to its effectiveness in skincare formulations.
Used in Nutraceutical Industry:
Hydroxytyrosol Acetate is used as a dietary supplement for its health-promoting properties. It is known to support cardiovascular health, improve cognitive function, and enhance overall well-being. Its antioxidant activity also helps in reducing the risk of various chronic diseases associated with oxidative stress.

InChI:InChI=1/C10H12O4/c1-7(11)14-5-4-8-2-3-9(12)10(13)6-8/h2-3,6,12-13H,4-5H2,1H3

Upstream product

• 10597-60-1 hydroxytyrosol 
• 75-36-5 acetyl chloride 
• 141-78-6 ethyl acetate 
• 32619-42-4 oleuropeine 
• 58556-55-1 2-(4-hydroxyphenyl)ethyl acetate 
• 491845-54-6 2-(4'-hydroxyphenyl)ethyl hexanoate 
• 2380-78-1 homovanillyl alcohol 
• 196081-78-4 3-bromo-4-hydroxyphenylethyl alcohol 
• 99-40-1 2-chloro-3',4'-dihydroxyacetophenone 
• 120-80-9 benzene-1,2-diol 
• 127-08-2 potassium acetate 
• 104693-00-7 1-chloro-2-(3,4-dihydroxyphenyl)ethane 
• 150994-00-6 2-(3-formyl-4-hydroxyphenyl)ethyl acetate 
• 501-94-0 p-hydroxyphenethyl alcohol 

Downstream Products

• 10597-60-1 hydroxytyrosol 
• 1185745-16-7 2-[3′-hydroxy-4′-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]ethyl acetate 
• 1185745-17-8 2-[4′-hydroxy-3′-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]ethyl acetate 

Relevant academic research and scientific papers

Identification of hydroxytyrosyl oleate, a derivative of hydroxytyrosol with anti-inflammatory properties, in olive oil by-products

Hydroxytyrosyl esters with short, medium and long acyl chains were evaluated for their ability to reduce nitric oxide (NO) production by lipopolysaccharide-stimulated RAW264.7 macrophages. Among the compounds tested, C18 esters, namely hydroxytyrosyl stea

Antioxidant activity of hydroxytyrosol acetate compared with that of other olive oil polyphenols

Hydroxytyrosol acetate was synthesized, and the antioxidant activity of this olive oil component was assessed in comparison with that of other olive oil components, namely hydroxytyrosol, oleuropein, 3,4-DHPEA-EA, and α-tocopherol in bulk oil and oil-in-water emulsions. The activity of the compounds was also assessed by scavenging of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Hydroxytyrosol acetate had a weaker DPPH radical scavenging activity than hydroxytyrosol, oleuropein, or 3,4-DHPEA-EA but it had a radical scavenging activity similar to that of α-tocopherol. In oil, the antioxidant activity of hydroxytyrosol acetate was much higher than that of α-tocopherol or oleuropein, but in an emulsion 3,4-DHPEA-EA and α-tocopherol were more effective as antioxidants than hydroxytyrosol acetate. The antioxidant activity of hydroxytyrosol acetate was rather similar to that of hydroxytyrosol in oil and emulsions despite the difference in DPPH radical scavenging activity.

Antioxidant and Biological Activities of Hydroxytyrosol and Homovanillic Alcohol Obtained from Olive Mill Wastewaters of Extra-Virgin Olive Oil Production

Some constituents of the Mediterranean diet, such as extra-virgin olive oil (EVOO) contain substances such as hydroxytyrosol (HT) and its metabolite homovanillic alcohol (HA). HT has aroused much interest due to its antioxidant activity as a radical scavenger, whereas only a few studies have been made on the HA molecule. Both chemical synthesis and extraction techniques have been developed to obtain these molecules, with each method having its advantages and drawbacks. In this study, we report the use of tyrosol from olive mill wastewaters as a starting molecule to synthesize HT and HA, using a sustainable procedure characterized by high efficiency and low cost. The effects of HT and HA were evaluated on two cell lines, THP-1 human leukemic monocytes and L-6 myoblasts from rat skeletal muscle, after treating the cells with a radical generator. Both HT and HA efficiently inhibited ROS production. In particular, HT inhibited the proliferation of the THP-1 leukemic monocytes, while HA protected L-6 myoblasts from cytotoxicity.

Chemoenzymatic synthesis of hydroxytyrosol monoesters and their suppression effect on nitric oxide production stimulated by lipopolysaccharides

Fatty acid monoesters of hydroxytyrosol [2-(3,4-dihydroxyphenyl)ethanol] were synthesized in two steps from tyrosol (4-hydroxyphenylethanol) by successive Candida antarctica lipase B-catalyzed chemoselective acylation on the primary aliphatic hydroxy group over phenolic hydroxy group in tyrosol, and 2-iodoxybenzoic acid (IBX)-mediated hydroxylation adjacent to the remaining free phenolic hydroxy group. Examination of their suppression effects on nitric oxide production stimulated by lipopolysaccharides in RAW264.7 cells showed that hydroxytyrosol butyrate exhibited the highest inhibition (IC50 7.0 μM) among the tested compounds.

Chemoenzymatic synthesis and radical scavenging of sulfated hydroxytyrosol, tyrosol, and acetylated derivatives

Potential metabolites of bioactive compounds are important for their biological activities and as authentic standards for metabolic studies. The phenolic compounds contained in olive oil are an important part of the human diet, and therefore their potenti

A three-step, gram-scale synthesis of hydroxytyrosol, hydroxytyrosol acetate, and 3,4-dihydroxyphenylglycol

Hydroxytyrosol and two other polyphenols of olive tree, hydroxytyrosol acetate and 3,4-dihydroxyphenylglycol, are known for a wide range of beneficial activities in human health and prevention from diseases. The inability to isolate high, pure amounts of these natural compounds and the difficult and laborious procedures for the synthesis of them led us to describe herein an efficient, easy, cheap, and scaling up synthetic procedure, from catechol, via microwave irradiation.

Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses

Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection.

Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity

Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties.

An efficient, economical synthesis of hydroxytyrosol and its protected forms via Baeyer-Villiger oxidation

An efficient and practical preparation of hydroxytyrosol and its orthogonally-protected forms was developed from inexpensive tyrosol. The utilization of Baeyer-Villiger oxidation enables the chemoselective introduction of a phenolic hydroxyl group in good yield.

Surface-active properties of lipophilic antioxidants tyrosol and hydroxytyrosol fatty acid esters: A potential explanation for the nonlinear hypothesis of the antioxidant activity in oil-in-water emulsions

Our group has recently observed a nonlinear tendency in antioxidant capacity of different hydroxytyrosol fatty acid esters in fish oil-in-water emulsions, where a maximum of antioxidant efficiency appeared for hydroxytyrosol octanoate. These results appea