Mechanochemo-enzymatic Synthesis of Aromatic Aldehyde Oxime Esters

The synthesis of aromatic aldehyde oxime esters (considered fragrances, antifungal and antimicrobial compounds) was achieved by two reactions which combine the advantage of green chemistry and biocatalysis. In the first step, the mechanochemical oxime synthesis by means of grindstone milling of six solid aromatic aldehydes and hydroxylamine hydrochloride in the presence of FlorisilR, as the best support, yielded the aromatic aldehyde oximes 1–6 with high purity and good yields. In the second step the lipase catalyzed acetylation reaction at 40°C for three days of those oximes with vinyl and isopropenyl acetates as acyl donor substrates and ethyl acetate as the solvent, yielded the aromatic aldehyde oxime esters. With Candida antarctica lipase (Novozyme 435), the conversions of oximes 1–6 into their esters were ≥ 99% according to the 1H NMR results and it was the best biocatalyst compared with others such as Candida rugosa (CRL), porcine pancreas lipase and the recombinant lipase LipMatCCR11 from the thermophilic strain Geobacillus thermoleovorans CCR11 cloned and expressed in Escherichia coli BL21 (DE3), all of which showed lower yields.

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Hydrolysis Activity of Virgin Coconut Oil Using Lipase from Different Sources

Scientifica ◽

10.1155/2018/9120942 ◽

2018 ◽

Vol 2018 ◽

pp. 1-6 ◽

Cited By ~ 2

Author(s):

T. A. V. Nguyen ◽

Truong D. Le ◽

Hoa N. Phan ◽

Lam B. Tran

Keyword(s):

Time Course ◽

Candida Rugosa ◽

Coconut Oil ◽

Virgin Coconut Oil ◽

Porcine Pancreas ◽

Hydrolysis Degree ◽

Porcine Pancreas Lipase ◽

Hydrolysis Process ◽

Hydrolysis Of ◽

Different Sources

Two types of lipase, Candida rugosa lipase (CRL) and porcine pancreas lipase (PPL), were used to hydrolyze virgin coconut oil (VCO). The hydrolysis process was carried out under four parameters, VCO to buffer ratio, lipase concentration, pH, and temperature, which have a significant effect on hydrolysis of lipase. CRL obtained the best hydrolysis condition at 1 : 5 of VCO to buffer ratio, 1.5% of CRL concentration, pH 7, and temperature of 40°C. Meanwhile, PPL gave different results at 1 : 4 of VCO to buffer ratio, 2% of lipase concentration, pH 7.5, and 40°C. The highest hydrolysis degree of CRL and PPL was obtained after 16 hours and 26 hours, reaching 79.64% and 27.94%, respectively. Besides, the hydrolysis process was controlled at different time course (every half an hour) at the first 4 hours of reaction to compare the initial hydrolysis degree of these two lipase types. FFAs from hydrolyzed products were isolated and determined the percentage of each fatty acid which contributes to the FFAs mixture. As a result, medium chain fatty acids (MCFAs) made up the main contribution in composition of FFAs and lauric acid (C12) was the largest segment (47.23% for CRL and 44.23% for PPL).

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The Zwitterionic Imidazolium Salt: First Used for Synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones under Solvent-Free Conditions

Journal of Chemistry ◽

10.1155/2013/280585 ◽

2013 ◽

Vol 2013 ◽

pp. 1-5 ◽

Cited By ~ 1

Author(s):

Baocheng Zhou ◽

Wenxing Chen

Keyword(s):

Aromatic Aldehyde ◽

Hippuric Acid ◽

Aromatic Aldehydes ◽

Solvent Free ◽

Imidazolium Salt ◽

H Nmr ◽

Solvent Free Conditions ◽

High Yields ◽

Electron Donating Groups

The zwitterionic imidazolium salt was prepared and characterized by1H NMR. It was first used for synthesis of azlactones via Erlenmeyer synthesis from aromatic aldehydes and hippuric acid under solvent-free conditions. It was found that aldehyde substituents play an important role in these reactions. Better conversions and therefore higher isolated yields were observed when electron-withdrawing groups (EWG-) were present in the aromatic aldehyde. Opposite results were shown when electron-donating groups (EDG-) were present in the aromatic aldehyde. However, azlactones were obtained in moderate to high yields.

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Ultrasound-assisted aqua-mediated synthesis of multi-substituted tetrahydropyridine-3-carboxylates using N-carboxymethyl-3-pyridinium hydrogensulfate ([N-CH2CO2H-3-pic]+HSO4−) as a new efficient ionic liquid catalyst

SN Applied Sciences ◽

10.1007/s42452-021-04671-9 ◽

2021 ◽

Vol 3 (6) ◽

Author(s):

Kobra Nikoofar ◽

Fatemeh Shahriyari

Keyword(s):

Ionic Liquid ◽

Reaction Times ◽

Aromatic Aldehydes ◽

Environmentally Benign ◽

H Nmr ◽

Sonic Waves ◽

Ft Ir ◽

High Yields ◽

Work Up ◽

C Nmr

AbstractA simple, straightforward, and ultrasound-promoted method for the preparation of some highly functionalized tetrahydropyridines reported via pseudo five-component reaction of (hetero)aromatic aldehydes, different anilines, and alkyl acetoacetates in the presence of [N-CH2CO2H-3-pic]+HSO4−, as a novel ionic liquid, in green aqueous medium. The IL was synthesized utilizing simple and easily-handled substrates and characterized by FT-IR, 1H NMR, 13C NMR, GC-MASS, FESEM, EDX, and TGA/DTG techniques. The procedure contains some highlighted aspects which are: (a) performing the MCR in the presence of aqua and sonic waves, as two main important and environmentally benign indexes in green and economic chemistry, (b) high yields of products within short reaction times, (c) convenient work-up procedure, (d) preparing the new IL via simple substrates and procedure.

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Synthesis, Characterization and Study of the Biological activity of Some Aldimines Derivatives

E-Journal of Chemistry ◽

10.1155/2006/618718 ◽

2006 ◽

Vol 3 (4) ◽

pp. 257-261 ◽

Cited By ~ 2

Author(s):

Mohamed N. Ibrahim ◽

Hazem K. Al - Deeb

Keyword(s):

Biological Activity ◽

Schiff Bases ◽

Aromatic Aldehyde ◽

Aromatic Amine ◽

Elemental Analysis ◽

Primary Aromatic Amine ◽

H Nmr

A number of imines derivatives have been synthesized, they were obtained by condensation of aromatic aldehyde derivatives with primary aromatic amine derivatives. Their structures have been characterised by IR,1H NMR in addition to the elemental analysis. The biological activity of these imines (which are also known as Schiff bases) were examined against different type of microorganisms and they found to have considerable activity in comparison with the most commonly used antibiotics.

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Usage of immobilized porcine pancreas lipase in the hydrolysis of roselle (Hibiscus sabdariffa L.) seed oil

10.1063/1.5000220 ◽

2017 ◽

Author(s):

Chau Tran Diem Ai ◽

Vo Thi Hong Linh ◽

Tran Thi Ngoc Yen ◽

Nguyen Thi Nguyen ◽

Phan Ngoc Hoa

Keyword(s):

Seed Oil ◽

Hibiscus Sabdariffa ◽

Porcine Pancreas ◽

Porcine Pancreas Lipase ◽

Hydrolysis Of

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Synthesis and Pharmacological Evaluation of 2-(4-Halosubstituted phenyl)-4,5-diphenyl-1H-imidazoles

E-Journal of Chemistry ◽

10.1155/2008/921256 ◽

2008 ◽

Vol 5 (3) ◽

pp. 447-452 ◽

Cited By ~ 3

Author(s):

G. Nagalakshmi

Keyword(s):

Anticonvulsant Activity ◽

Glacial Acetic Acid ◽

Ammonium Acetate ◽

Antiinflammatory Activity ◽

Aromatic Aldehydes ◽

Mass Spectral Data ◽

Mass Spectral ◽

H Nmr ◽

Structural Assignment ◽

Paw Oedema

In the present study, 2-(4-halosubstituted phenyl)-4,5-diphenyl-1Himidazoles have been synthesized by refluxing benzil and ammonium acetate with different 4-halosubstituted aromatic aldehydes in glacial acetic acid. The structural assignment of this compound has been made on the basis of elemental analysis, UV, IR,1H NMR and Mass spectral data. Toxicity of the compound has been determined. The synthesized compound was evaluated for antiinflammatory activity against carrageenan induced paw oedema and anticonvulsant activity against maximal electro-shock-induced convulsions in rats.

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Three-Component Synthesis of 4-Arylidene-3-alkylisoxazol-5(4H)-ones in the presence of potassium 2,5-dioxoimidazolidin-1-ide

Current Organic Chemistry ◽

10.2174/1385272825666210212120517 ◽

2021 ◽

Vol 25 ◽

Author(s):

Neda Reihani ◽

Hamzeh Kiyani

Keyword(s):

Ethylene Glycol ◽

Ethyl Acetoacetate ◽

Reaction Medium ◽

Hydroxylamine Hydrochloride ◽

Aromatic Aldehydes ◽

Catalyst Loading ◽

Efficient Synthesis ◽

Current Process ◽

High Yields ◽

Low Catalyst Loading

: An efficient synthesis of 4-arylidene-3-alkylisoxazole-5(4H)-ones has been implemented via the three-component cyclocondensation of aryl(heteroaryl)aldehydes with hydroxylamine hydrochloride and β-ketoesters. The potassium 2,5-dioxoimidazolidin-1-ide has been introduced as the new organocatalyst to facilitate of this heterocyclization. In the current process, three starting materials, including substituted benzaldehydes/heterocyclic aromatic aldehydes, hydroxylamine hydrochloride, and ethyl acetoacetate/propyl acetoacetate/butyryl acetoacetate have been successfully used for the synthesize of the number of substituted isoxazole-5(4H)-ones in good to high yields in ethylene glycol as a green reaction medium at 80 ºC. The low catalyst loading is also a main advantage over the some reported catalysts.

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