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Usage

Uses

Used in Fragrance and Flavor Industry:
(R)-(-)-1-(4'-hydroxyphenyl)ethanol is used as a key ingredient for imparting floral and fruity notes in the fragrance and flavor industry. Its unique scent profile makes it a valuable component in creating a wide range of scents for perfumes, cosmetics, and personal care products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, (R)-(-)-1-(4'-hydroxyphenyl)ethanol is utilized as a chiral intermediate in the synthesis of various drug compounds. Its chiral nature allows for the development of enantiomerically pure compounds, which is crucial for ensuring the desired therapeutic effects and minimizing potential side effects in pharmaceutical applications.

Upstream product

• 2628-17-3 4-Vinylphenol 
• 7400-08-0 p-Coumaric Acid 
• 108-95-2 phenol 
• 93453-79-3 1-(4-hydroxyphenyl)ethanol 
• 123-07-9 4-Ethylphenol 
• 99-93-4 4-Hydroxyacetophenone 
• 108-05-4 vinyl acetate 
• 144-55-8 sodium hydrogencarbonate 
• 84775-31-5 1-(4-((2-methoxyethoxy)methoxy)phenyl)ethanone 

Relevant academic research and scientific papers

Enantioselective biocatalytic reduction of non-protected hydroxyacetophenones

Direct enantioselective reduction of -, - and -hydroxyacetophenone without protection of the hydroxy moiety was carried out in the presence of (R)- and (S)-alcohol dehydrogenases as bio-catalysts. Whereas reduction of -hydroxyacetophenone gave only low to

Bioactive constituents from the rhizomes of Dioscorea septemloba Thunb

Eight new compounds, dioscorosides G (1), H1 (2), H2 (3), dioscorol B (4), dioscorosides I (5), J (6), K1 (7), and K2 (8), together with twelve known ones (9–20) were obtained from the rhizomes of Dioscorea sept

Synthesis of (S)-1-(4-hydroxyphenyl)alcohols by eugenol dehydrogenase from Pseudomonas fluorescens E118

(S)-1-(4-Hydroxyphenyl)ethanol and (S)-1-(4-hydroxyphenyl)propanol were synthesized with enantiomeric excesses of 96.6% and 95.2%, respectively, from the corresponding 4-alkylphenols by eugenol dehydrogenase from Pseudomonas fluorescens E118. The enantios

Synthesis and characterization of novel silica coated magnetic nanoparticles with tags of β-cyclodextrin: application as an eco-friendly and chiral micro-vessel catalyst in the enantioselective reduction of ketones

In this work, we report the synthesis of a novel, green and recoverable organic–inorganic magnetic nanocomposite by grafting β-cyclodextrin on the surface of a silica-coated magnetic nanoparticle, Fe3O4@SiO2/Pr-β-CD. FT-IR spectroscopy, transmission electron microscopy, CHN analysis, thermogravimetric analysis, vibrating sample magnetometer and X-ray diffraction analyses confirmed its structure. The magnetic core–shell structured modified silica microsphere has been successfully used as a chiral micro-vessel catalyst for the enantioselective reduction of ketones by NaBH4. The described catalyst was regenerated and reused without any significant changes in the yield and enantiomeric excess.

The reaction mechanism of chiral hydroxylation of p -OH and p -NH 2 substituted compounds by ethylbenzene dehydrogenase

Ethylbenzene dehydrogenase (EbDH; enzyme commission (EC) number: 1.17.99.2) is a unique biocatalyst that hydroxylates alkylaromatic and alkylheterocyclic compounds to (S)-secondary alcohols under anaerobic conditions. The enzyme exhibits a high promiscuity catalyzing oxidation of over 30 substrates, inter alia, para-substituted alkylphenols and alkylanilines. Secondary alcohols with OH and NH2 substituents in the aromatic ring are highly valuable synthons for many biologically active compounds in the fine chemical industry. EbDH hydroxylates most of the studied compounds highly enantioselectively, except for five substrates that harbour OH and NH2 groups in the para position, which exhibit a significant decrease in the percent enantiomeric excess (% ee). This phenomenon is inconsistent with the previously suggested enzyme mechanism, but it may be linked to a stabilization of the carbocation intermediate by deprotonation of the OH or NH2 substituent in the active site that yields a transient quinone (imine) ethide species. This would initiate an alternative reaction pathway involving the addition of a water molecule to a C=C double bond. This hypothesis was cross-validated by density functional theory (DFT) cluster modelling of the alternative reaction pathway with 4-ethylphenol, as well as by experimental assessment of the pH dependency of enantiomeric excesses. The results reported herein suggest that the alternative reaction pathway may significantly contribute to the overall reaction if the carbocation intermediates are stabilized by deprotonation.

A Rational Active-Site Redesign Converts a Decarboxylase into a C=C Hydratase: "tethered Acetate" Supports Enantioselective Hydration of 4-Hydroxystyrenes

The promiscuous regio- and stereoselective hydration of 4-hydroxystyrenes catalyzed by ferulic acid decarboxylase from Enterobacter sp. (FDC-Es) depends on bicarbonate bound in the active site, which serves as a proton relay activating a water molecule fo

An Enantioconvergent Benzylic Hydroxylation Using a Chiral Aryl Iodide in a Dual Activation Mode

The application of a triazole-substituted chiral iodoarene in a direct enantioselective hydroxylation of alkyl arenes is reported. This method allows the rapid synthesis of chiral benzyl alcohols in high yields and stereocontrol, despite its nontemplated nature. In a cascade activation consisting of an initial irradiation-induced radical C-H-bromination and a consecutive enantioconvergent hydroxylation, the iodoarene catalyst has a dual role. It initiates the radical bromination in its oxidized state through an in-situ-formed bromoiodane and in the second, Cu-catalyzed step, it acts as a chiral ligand. This work demonstrates the ability of a chiral aryl iodide catalyst acting both as an oxidant and as a chiral ligand in a highly enantioselective C-H-activating transformation. Furthermore, this concept presents an enantioconvergent hydroxylation with high selectivity using a synthetic catalyst.

Deracemization of sec-alcohols through sequential application of C. Albicans and Ketoreductases

A biocatalytic cascade process was developed using immobilized cells of the wild type yeast Candida albicans CCT 0776 in calcium alginate beads and a commercially available ketoreductase. The aim was to promote deracemization by stereoinversion of (±)-1-arylethanols in high substrate concentration (above 100 mmol L-1) to prepare the (R)-enantiomers of the alcohols (90-99percent), with a high enantiomeric excess (83-99percent) after 2 to 19 h. The (R)-1-(3-methoxyphenyl)ethanol, with 70percent yield and 91percent ee, obtained after 5 h was used to prepare (S)-1-(3-methoxyphenyl)-ethylamine with 60percent yield and 91percent ee after two steps, a key intermediate in the synthesis of (S)-rivastigmine.

Multienzyme One-Pot Cascade for the Stereoselective Hydroxyethyl Functionalization of Substituted Phenols

The operability and substrate scope of a redesigned vinylphenol hydratase as a single biocatalyst or as part of multienzyme cascades using either substituted coumaric acids or phenols as stable, cheap, and readily available substrates are reported.

Multigram Scale Enzymatic Synthesis of (R)-1-(4′-Hydroxyphenyl)ethanol Using Vanillyl Alcohol Oxidase

The enantioselective oxyfunctionalisation of C?H bonds is a highly interesting reaction, as it provides access to chiral alcohols that are important pharmaceutical building blocks. However, it is hard to achieve using traditional methods. One way in which it can be achieved is through the action of oxidative enzymes. Although many reports of the oxyfunctionalisation capabilities of enzymes at an analytical scale have been published, reports on the use of enzymes to achieve oxyfunctionalisation on a synthetically relevant scale are fewer. Here, we describe the scale-up of the conversion of 4-ethylphenol to (R)-1-(4′-hydroxyphenyl)ethanol using the flavin-dependent enzyme vanillyl alcohol oxidase. The process was optimised by testing different reaction media and substrate and enzyme concentrations and by performing it under an oxygen atmosphere. Under optimised reaction conditions, 4.10 g (R)-1-(4′-hydroxyphenyl)ethanol at 97% ee was obtained from 10 g 4-ethylphenol (isolated yield 36%). These results highlight some of the challenges that can be encountered during scale-up of an enzymatic oxyfunctionalisation process to a synthetically relevant scale and will be of use for the development of enzymatic processes for the synthesis of industrially relevant compounds. (Figure presented.).