58556-55-1

Usage

Chemical Properties

Off-White Solid

Uses

Tyrosol derivative

InChI:InChI=1/C10H12O3/c1-8(11)13-7-6-9-2-4-10(12)5-3-9/h2-5,12H,6-7H2,1H3

Upstream product

• 501-94-0 p-hydroxyphenethyl alcohol 
• 75-36-5 acetyl chloride 
• 60037-42-5 2-(4-acetoxyphenyl)ethyl acetate 
• 141-78-6 ethyl acetate 
• 60759-49-1 N-acetyl-1,3-oxazol-2-one 
• 95-47-6 o-xylene 
• 17207-22-6 2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl acetate 
• 108-05-4 vinyl acetate 
• 108-24-7 acetic anhydride 
• 75-05-8 acetonitrile 
• 14140-15-9 4-(2-bromoethyl)phenol 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 406-95-1 2,2,2-trifluoroethyl acetate 

Downstream Products

• 94414-03-6 4-[2-(acetyloxy)ethyl]-4-hydroxy-2,5-cyclohexadien-1-one 
• 115124-79-3 Acetic acid 2-(2-hydroxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-2-yl)-ethyl ester 
• 62287-22-3 Acetic acid 2-(3,6-dioxo-cyclohexa-1,4-dienyl)-ethyl ester 
• 150994-00-6 2-(3-formyl-4-hydroxyphenyl)ethyl acetate 
• 712223-57-9 acetic acid 2-[4-(trifluoromethanesulfonyloxy)phenyl]ethyl ester 
• 162358-08-9 diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate 
• 162358-07-8 2-(4-octylphenyl)-1-iodoethane 
• 162358-05-6 2-(4-Octylphenyl)ethyl alcohol 
• 162358-06-7 4-octylphenethyl methanesulfonate 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 93675-93-5 rengyol monoacetate 
• 107389-92-4 4-hydroxy-4-(2'-acetoxyethyl)cyclohexanone 
• 93675-85-5 rengyol 
• 101489-38-7 trans-1-(2-hydroxyethyl)cyclohexane-1,4-diol 

Relevant academic research and scientific papers

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

Chemoenzymatic Synthesis and α-Glucosidase Inhibitory Activity of Dimeric Neolignans Inspired by Magnolol

A chemoenzymatic synthesis of a small library of dimeric neolignans inspired by magnolol (1) is reported. The 2-iodoxybenzoic acid (IBX)-mediated regioselective ortho-hydroxylation of magnolol is described, affording the bisphenols 6 and 7. Further magnol

Optimization of lipase-catalyzed synthesis of acetylated tyrosol by response surface methodology

The ability of a noncommercial immobilized lipase from Staphylococcus xylosus (SXLi) to catalyze the transesterification of tyrosol and ethyl acetate was investigated. Response surface methodology was used to evaluate the effects of the tempera

3, 4-dihydroxyphenylethanol synthesis method

An embodiment of the invention discloses a 3, 4-dihydroxyphenylethanol synthesis method which includes the steps: taking a compound I as a raw material to prepare a compound II under the action of a catalyst for standby application; performing reaction on the compound II prepared in the first step and strong acid, and extracting and concentrating a reactant to prepare a compound III; dissolving the compound III in a solvent to perform reaction under the of a catalyst to prepare a compound IV; performing diazo-reaction and acidic hydrolysis on the compound IV to generate 3, 4-dihydroxyphenylethanol. According to the 3, 4-dihydroxyphenylethanol synthesis method, raw materials are moderate in cost, mass production is easily implemented, the purity of the 3, 4-dihydroxyphenylethanol is higherthan 99%, and overall yield can reach 78% or more. The synthesis method is simple in reaction condition, special requirements for devices are omitted, the method is easily implemented in industrial production, and organic solvents can be completely recycled and reused in the whole preparation process.

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.

Tyrosol fatty acid ester compounds as well as preparation method and application thereof

The invention discloses a tyrosol fatty acid ester compounds as well as a preparation method and application thereof, which belong to the technical field of biological medicines. According to the tyrosol fatty acid ester compounds, the chemical structure of tyrosol is derivatized, fatty acid is introduced into the structure, the structure is quite different from the structure of tyrosol, and the tyrosol fatty acid ester compounds have good bacteriostatic and anti-oxidation effects. The invention further provides the preparation method for the tyrosol fatty acid ester, i.e., with tyrosol, triphenyl phosphine and fatty acid as materials, tetrahydrofuran is added under the shielding of nitrogen, diisopropyl azodiformate is dripped under 0 DEG C, and after reaction, tyrosol fatty acid ester isobtained by column chromatography. The advantages are as follows: the tyrosol fatty acid ester compounds disclosed by the invention have good pharmacodynamic performance and high bioactivity; the reaction process of the preparation method has short steps and good selectivity, the target compounds can be obtained by one-step reaction, yield is high, and the preparation is environmentally friendly;and tyrosol fatty acid ester has bacteriostatic and anti-oxidation effects.

Lipase-mediated selective acetylation of primary alcohols in ethyl acetate

An environmental friendly process to selectively acetylate primary alcohols was demonstrated. The esterification process consists of treatment of a primary alcohol in the presence of immobilized C. antarctica lipase (Novozyme-435) in ethyl acetate at room temperature. Primary alcohols were acetylated in the presence of secondary alcohols and phenols.

Isopropenyl acetate: A cheap and general acylating agent of alcohols under metal-free conditions

Functionalized primary, secondary and tertiary alcohols are efficiently acetylated by isopropenyl acetate and catalytic p-TsOH.

Tyrosol and hydroxytyrosol derivatives as antitrypanosomal and antileishmanial agents

Trypanosomiasis and leishmaniasis keep being a real challenge for health and development of African countries. Existing treatments have considerable side effects and increase resistance of the parasites. We have measured antitrypanosomal and antileishmanial activity of natural phenols, tyrosol (TYR) and hydroxytyrosol (HT) and several of their esters and metabolites. We found significant IC50 values against Trypanosoma brucei for HT decanoate ester and HT dodecanoate ester (0.6 and 0.36 μM, respectively). This represents a large increase in activity with respect to HT (79 and 132 fold, respectively). Moreover, both compounds displayed a high selectivity index against MRC-5, a non-tumoral human cell line (118 and 106, respectively). Then, we synthesized a focused library of compounds to explore structure-activity. We found the ether and thiourea analogs of HT decanoate ester and HT dodecanoate ester also showed IC50 values against T. brucei in the low micromolar range. In conclusion, the di-ortho phenolic ring and medium size alkyl chain are essential for activity whereas the nature of the chemical bond among them seems less important.

Structural and catalytic characterization of a fungal baeyer-villiger monooxygenase

Baeyer-Villiger monooxygenases (BVMOs) are biocatalysts that convert ketones to esters. Due to their high regio-, stereo- and enantioselectivity and ability to catalyse these reactions under mild conditions, they have gained interest as alternatives to chemical Baeyer-Villiger catalysts. Despite their widespread occurrence within the fungal kingdom, most of the currently characterized BVMOs are from bacterial origin. Here we report the catalytic and structural characterization of BVMOAFL838 from Aspergillus flavus. BVMOAFL838 converts linear and aryl ketones with high regioselectivity. Steady-state kinetics revealed BVMOAFL838 to show significant substrate inhibition with phenylacetone, which was more pronounced at low pH, enzyme and buffer concentrations. Para substitutions on the phenyl group significantly improved substrate affinity and increased turnover frequencies. Steady-state kinetics revealed BVMOAFL838 to preferentially oxidize aliphatic ketones and aryl ketones when the phenyl group are separated by at least two carbons from the carbonyl group. The X-ray crystal structure, the first of a fungal BVMO, was determined at 1.9 A and revealed the typical overall fold seen in type I bacterial BVMOs. The active site Arg and Asp are conserved, with the Arg found in the ginh position. Similar to phenylacetone monooxygenase (PAMO), a two residue insert relative to cyclohexanone monooxygenase (CHMO) forms a bulge within the active site. Approximately half of the gvariableh loop is folded into a short ?-helix and covers part of the active site entry channel in the non-NADPH bound structure. This study adds to the current efforts to rationalize the substrate scope of BVMOs through comparative catalytic and structural investigation of different BVMOs.