Benzoic Acid Derivatives (benzoic + acid_derivative)

Distribution by Scientific Domains

Selected Abstracts

Selective Oxidation of Acetophenones Bearing Various Functional Groups to Benzoic Acid Derivatives with Molecular Oxygen

Ryota Nakamura
Abstract Acetophenones substituted by alkyl, alkoxy, acetoxy, and halogen groups were selectively oxidized with molecular oxygen to the corresponding benzoic acids by using the N,N,,N,, -trihydroxyisocyanuric acid (THICA)/cobalt(II) acetate [Co(OAc)2] and THICA/Co(OAc)2/manganese(II) acetate [Mn(OAc)2]. For example, 4-methylacetophenone was selectively oxidized with molecular oxygen to 4-acetylbenzoic acid (85%) by THICA/Co(OAc)2 and to 4-methylbenzoic acid (93%) by Mn(OAc)2, while terephthalic acid was obtained in 93% with the THICA/Co(OAc)2/Mn(OAc)2 catalytic system. It is interesting that the acetyl group on the aromatic ring is efficiently converted by a very small amount of Mn(OAc)2 to the corresponding carboxylic acid, and that the present method provides a versatile route to acetylbenzoic acids which are difficult to prepare by conventional methods. [source]

Electrochemical Oxidation of Benzoic Acid Derivatives on Boron Doped Diamond: Voltammetric Study and Galvanostatic Electrolyses

B. Louhichi
Abstract The electrochemical oxidation of aqueous wastes polluted with benzoic and salicylic acids and phthalic anhydride on boron-doped diamond electrodes has been studied. The complete mineralization of the organic waste has been obtained in each case regardless of the nature of the compound, composition of the solution, and current density. Different voltammetric behaviors between benzoic acid, salicylic acid, and phthalic anhydride were obtained in the voltammetric study, but no differences in the electrochemical oxidation of the three compounds seems to exist in the bulk electrolyses study. The total mineralization of the three compounds at different current densities confirms that the oxidation must occur directly on the electrode surface and/or by hydroxyl radicals generated by decomposition of water and/or by other oxidants electro-generated from the sulfate oxidation. [source]

The Reaction of (N-Isocyanimino)triphenylphosphorane with Benzoic Acid Derivatives: A Novel Synthesis of 2-Aryl-1,3,4-oxadiazole Derivatives.

CHEMINFORM, Issue 22 2007
Ali Souldozi
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]

Macrocyclic polyamine-modified poly(glycidyl methacrylate- co -ethylene dimethacrylate) monolith for capillary electrochromatography

Yun Tian
Abstract 1,4,10,13,16-Pentaazatricycloheneicosane-9,17-dione (macrocyclic polyamine)-modified polymer-based monolithic column for CEC was prepared by ring opening reaction of epoxide groups from poly(glycidyl methacrylate- co -ethylene dimethacrylate) (GMA- co -EDMA) monolith with macrocyclic polyamine. Conditions such as reaction time and concentration of macrocyclic polyamine for the modification reaction were optimized to generate substantial EOF and enough chromatographic interactions. Anodic EOF was observed in the pH range of 2.0,8.0 studied due to the protonation of macrcyclic polyamine at the surface of the monolith. Morphology of the monolithic column was examined by SEM and the incorporation of macrocyclic polyamine to the poly(GMA- co -EDMA) monolith was characterized by infrared (IR) spectra. Successful separation of inorganic anions, isomeric benzenediols, and benzoic acid derivatives on the monolithic column was achieved for CEC. In addition to hydrophobic interaction, hydrogen bonding and electrostatic interaction played a significant role in the separation process. [source]

Fungitoxic phenols from carnation (Dianthus caryophyllus) effective against Fusarium oxysporum f. sp. dianthi

Paolo Curir
Abstract The phenol compositions of two cultivars of carnation (Dianthus caryophyllus) namely "Gloriana" and "Roland", which are partially and highly resistant, respectively, to Fusarium oxysporum f. sp. dianthi have been investigated with the aim of determining if endogenous phenols could have an anti-fungal effect against the pathogen. Analyses were performed on healthy and F. oxysporum -inoculated in vitro tissues, and on in vivo plants. Two benzoic acid derivatives, protocatechuic acid (3,4-dihydroxybenzoic acid) and vanillic acid (4-hydroxy-3-methoxybenzoic acid), were found within healthy and inoculated tissues of both cultivars, together with the flavonol glycoside peltatoside (3-[6-O-(,- L -arabinopyranosyl)-,- D -glucopyranosyl] quercetin). These molecules proved to be only slightly inhibitory towards the pathogen. 2,6-Dimethoxybenzoic acid was detected in small amounts only in the inoculated cultivar "Gloriana", while the highly resistant cultivar "Roland" showed the presence of the flavone datiscetin (3,5,7,2,-tetrahydroxyflavone). The latter compound exhibited an appreciable fungitoxic activity towards F. oxysporum f. sp. dianthi. Copyright © 2003 John Wiley & Sons, Ltd. [source]

X-ray crystallographic structures of enamine and amine Schiff bases of pyridoxal and its 1:1 hydrogen-bonded complexes with benzoic acid derivatives: evidence for coupled inter- and intramolecular proton transfer

Shasad Sharif
Crystal structures of Schiff bases containing pyridoxal (PL), N -(pyridoxylidene)-tolylamine, C15H16N2O2 (I), N -(pyridox­ylidene)-methylamine, C9H12N2O2 (III), and their 1:1 adduct with 2-nitrobenzoic acid, (I)+ C7H4NO (II), and 4-nitrobenzoic acid, (III)+ C7H4NO (IV), serve as models for the coenzyme pyridoxal-5,-phosphate (PLP) in its PLP-dependent enzymes. These models allow the study of the intramolecular OHN hydrogen bond of PL/PLP Schiff bases and the H-acceptor properties of their pyridine rings. The free base (I) forms hydrogen-bonded chains involving the hydroxyl side groups and the rings of adjacent molecules, whereas (III) forms related hydrogen-bonded cyclic dimers. The adducts (II)/(IV) consist of 1:1 hydrogen-bonded complexes, exhibiting strong intermolecular bonds between the carboxylic groups of the acids and the pyridine rings of (I)/(III). In conclusion, the proton in the intramolecular O,H,N hydrogen bond of (I)/(III) is located close to oxygen (enolamine form). The added acids protonate the pyridine ring in (II)/(IV), but only in the latter case does this protonation lead to a shift of the intramolecular proton towards the nitrogen (ketoimine form). All crystallographic structures were observed in the open form. In contrast, the formation of the pyridinium salt by dissolving (IV) leads to the cyclic aminal form. [source]

Alterations in Taxol Production in Plant Cell Culture via Manipulation of the Phenylalanine Ammonia Lyase Pathway

Michelle C. Brincat
One approach to increasing secondary metabolite production in plant cell culture is to manipulate metabolic pathways to utilize more resources toward production of one desired compound or class of compounds, such as diverting carbon flux from competing secondary pathways. Since phenylalanine provides both the phenylisoserine side chain and the benzoyl moiety at C-2 of Taxol, we speculated that blockage of the phenylpropanoid pathway might divert phenylalanine into Taxol biosynthesis. We used specific enzyme inhibitors to target the first enzyme in the phenylpropanoid pathway, phenylalanine ammonia lyase (PAL), the critical control point for conversion of l -phenylalanine to trans -cinnamic acid. Cinnamic acid acted quickly in reducing PAL activity by 40,50%, without affecting total protein levels, but it generally inhibited the taxane pathway, reducing Taxol by 90% of control levels. Of the taxanes produced, 13-acetyl-9-dihydro-baccatin III and 9-dihydrobaccatin III doubled as a percentage of total taxanes in C93AD and CO93P cells treated with 0.20 and 0.25 mM cinnamic acid, when all other taxanes were lowered. The PAL inhibitor ,-aminooxyacetic acid (AOA) almost entirely shut down Taxol production at both 0.5 and 1.5 mM, whereas l -,-aminooxy-,-phenylpropionic acid (AOPP) had the opposite effect, slightly enhancing Taxol production at 1 ,M but having no effect at 10 ,M. The discrepancy in the effectiveness of AOA and AOPP and the lack of effect with addition of phenylalanine or benzoic acid derivatives further indicates that the impact of cinnamic acid on Taxol is related not to its effect on PAL but rather to a specific effect on the taxane pathway. On the basis of these results, a less direct route for inhibiting the phenylpropanoid pathway may be required to avoid unwanted side effects and potentially enhance Taxol production. [source]