103-45-7Relevant articles and documents
Synthesis of 2-phenylethyl acetate in the presence of Yarrowia lipolytica KKP 379 biomass
Bialecka-Florjanczyk, Ewa,Krzyczkowska, Jolanta,Stolarzewicz, Izabela,Kapturowska, Agata
, p. 241 - 245 (2012)
Increasing demand for natural products in the food industry has encouraged significant efforts toward the development of biotechnological processes for the production of flavour compounds. The aim of the present study was to synthesise 2-phenylethyl acetate, an essential aroma component for the food and cosmetic industries, by acetate ester alcoholysis with 2-phenylethanol in the presence of Yarrowia lipolytica KKP 379 biomass. Optimisation of reaction conditions were conducted, inter alia, by selection of the proper acyl donor and determination of optimal permeabilisation conditions for the yeast cell wall. Optimal reaction conditions enabled synthesis of the desired ester with an efficiency comparable to commercial enzymes, but at considerably lower cost.
Convenient tetrahydropyranylation of alcohols and phenols by catalytic ferric sulfate hydrate (Fe2(SO4)3· xH2O)
Li, Lingjun,Zhu, Lizhi,Zhang, Xinying,Zhang, Guisheng,Qu, Guirong
, p. 1120 - 1123 (2005)
Ferric sulfate hydrate (Fe2(SO4)3· xH2O) is found to be an efficient heterogeneous catalyst for the tetrahydropyranylation of alcohols and phenols at ambient or near ambient temperature. In addition, selective monotetrahydropyranylation of symmetrical diols is achieved under similar conditions. The deprotection of THP ether and direct transformation of THP ether to the corresponding acetate by Fe 2(SO4)3·xH2O is also studied. The simplicity of manipulation, mild conditions, reusable catalyst, good selectivity, and environment benign characters make this method a good alternative way for the THP protection of alcohols.
Facile catalyzed acylation of heteroatoms using BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride
Ghosh, Rina,Maiti, Swarupananda,Chakraborty, Arijit
, p. 6775 - 6778 (2004)
Acylation of a variety of alcohols, phenols, aliphatic and aromatic amines, a thiol and a thiophenol proceeds efficiently using BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride in a solvent or under solventless conditions, furnishing the corresponding acylated derivatives in very good to excellent yields.
Expanding ester biosynthesis in Escherichia coli
Rodriguez, Gabriel M,Tashiro, Yohei,Atsumi, Shota
, p. 259 - 265 (2014)
To expand the capabilities of whole-cell biocatalysis, we have engineered Escherichia coli to produce various esters. The alcohol O-acyltransferase (ATF) class of enzyme uses acyl-CoA units for ester formation. The release of free CoA upon esterification with an alcohol provides the free energy to facilitate ester formation. The diversity of CoA molecules found in nature in combination with various alcohol biosynthetic pathways allows for the biosynthesis of a multitude of esters. Small to medium volatile esters have extensive applications in the flavor, fragrance, cosmetic, solvent, paint and coating industries. The present work enables the production of these compounds by designing several ester pathways in E. coli. The engineered pathways generated acetate esters of ethyl, propyl, isobutyl, 2-methyl-1-butyl, 3-methyl-1-butyl and 2-phenylethyl alcohols. In particular, we achieved high-level production of isobutyl acetate from glucose (17.2 g l -1). This strategy was expanded to realize pathways for tetradecyl acetate and several isobutyrate esters.
Efficient liquid phase acylation of alcohols over basic ETS-10 molecular sieves
Waghmode, Suresh B.,Thakur, Vinay V.,Sudalai, Arumugam,Sivasanker, Subramanian
, p. 3145 - 3147 (2001)
Acylation of alcohols with acetic acid can be carried out efficiently in the liquid phase over microporous titanosilicate ETS-10-type catalysts. The reaction was studied over ETS-10 exchanged with, Li, Na, K, Rb, Cs, Ba and H ions. Activity for acylation of primary alcohols depends on the exchanged alkali ion and increases in the order LiNaKBa～H～Rb～Cs-ETS-10. These molecular sieves are also suitable for the acylation of secondary alcohols and esterification with long chain carboxylic acids.
Alkylchlorotins grafted to cross-linked polystyrene beads by a -(CH 2)n spacer (n-4, 6, 11): Selective, clean and recyclable catalysts for transesterification reactions
Camacho-Camacho, Carlos,Biesemans, Monique,Van Poeck, Manu,Mercier, Frederic A. G.,Willem, Rudolph,Darriet-Jambert, Karine,Jousseaume, Bernard,Toupance, Thierry,Schneider, Uwe,Gerigk, Ursula
, p. 2455 - 2461 (2005)
Insoluble polystyrene grafted compounds of the type (P-H) (1-t)(P-(CH2)nSnBupCl 3-p,}t, (P-H)(1-t){P-(CH2) nSnBuO)t and (P-H)(1-t)[(P-(CH 2)nSnBuCl}2O]t/2, in which (P-H) is a cross-linked polystyrene; n=4, 6, and 11; p=0 and 1; and t the degree of functionalisation, were synthesised from Amberlite XE-305, a polystyrene cross-linked with divinylbenzene. The compounds were characterised by using elemental analysis, and IR, Raman, solid-state 117Sn NMR, and 1H and 119Sn high-resolution MAS NMR spectroscopy. The influence of the spacer length and the tin functionality on the catalytic activity of these compounds, as well as their recycling ability, was assessed in the transesterifica tion reaction of ethyl acetate with various alcohols. These studies showed significant differences in the activity of the catalysts interpreted in terms of changes in the mobility of the catalytic centres. Some of the supported catalysts could be recycled at least seven times without noticeable loss of activity. The residual tin content in the reaction products was found to be as low as 3 ppm.
Structural and catalytic characterization of a fungal baeyer-villiger monooxygenase
Ferroni, Felix Martin,Tolmie, Carmien,Smit, Martha Sophia,Opperman, Diederik Johannes
, (2016)
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.
Organic Reducing Agents. Reduction of Electron Deficient Bromides by 1,2,2,6,6-Pentamethylpiperidine (PMP)/Mercaptoethanol
Amoli, Maryam,Workentin, Mark S.,Wayner, Danial D. M.
, p. 3997 - 4000 (1995)
1,2,2,6,6-pentamethylpiperidine (PMP) is shown to be an effective reducing agent for the radical chain conversion of primary bromoesters in these reactions to the corresponding esters.The problem of inefficient reduction of tertiary bromoesters in these reactions has been overcome by the addition of an alkyl thiol which mediates the hydrogen atom transfer between the two hindered alkyl centers.
Silphos [PCl3-n(SiO2)n]: A heterogeneous phosphine reagent for formylation and acetylation of alcohols and amines with ethyl formate and acetate
Iranpoor, Nasser,Firouzabadi, Habib,Jamalian, Arezu
, p. 7963 - 7966 (2005)
Alcohols and amines are formylated and acetylated in the presence of Silphos [PCl3-n(SiO2)n] in ethyl formate and ethyl acetate in high to excellent yields. This procedure provides a method to separate the product by a simple filtration.
Acetylation and formylation of alcohols in the presence of silica sulfuric acid
Shirini, Farhad,Zolfigol, Mohammad Ali,Mohammadi, Kamal
, p. 1617 - 1621 (2003)
Alcohols are converted to esters in a mild, clean, and efficient reaction with acetic and formic acids in the presence of silica sulfuric acid. All reactions were performed under mild and completely heterogeneous conditions in refluxing n-hexane.
