Showing papers on "Benzoic acid published in 1975"

Mechanism of Benzoic Acid Uptake by Saccharomyces cerevisiae

Abstract: A fast uptake of the preservative benzoic acid was observed in Saccharomyces cerevisiae, reaching saturation in about two min and then remaining constant at this level. The strong dependence of benzoic acid uptake on pH was due to the relative distribution of molecular and ionic forms in solution and not to the pH itself. The molecular form was the only one taken up by the cells. The specificity of the uptake mechanism was evidenced by the pattern of irreversible heat inactivation of the uptake system resembling protein denaturation by heat. Furthermore, the effect of temperature on the uptake was similar to that observed in enzymic reactions, whereas the kinetic data of uptake conformed to the Michaelis-Menten curve of saturation with a Km of 1.54 × 10-2 M and Vmax of 3 × 10-3 M/10s. The evidence presented in this paper indicates that compounds of protein nature are involved in the uptake of this preservative.

Photographic light-sensitive material

Abstract: A silver halide photographic light-sensitive material comprising a hydrophilic organic colloid layer containing a photographic additive dispersed therein using as a solvent a benzoic acid ester which has a boiling point of greater than 250° C at atmospheric pressure, which is soluble in water in a proportion of less than about 10% by weight, and which dissolves water in a proportion of less than about 5% by weight. The benzoic acid ester does not have any harmful influence on the human body and does not cause environmental pollution.

The conversion of L-phenylalanine into benzoic acid on the thylakoid membrane of higher plants.

Abstract: The conversion of L-phenylalanine into benzoic acid and other aromatic carboxylic acids was investigated in Nasturtium officinale (watercress), Astilbe chinensis, and Hydrangea macrophylla in vivo and in vitro. Comparative feeding experiments with radioactively labelled L-phenylalanine and cinnamic acid administered to intact leaf discs of A. chinensis indicated a rapid formation of benzoic acid from L-phenylalanine, whereas cinnamic acid was a poor precursor. Using a pulse-chase labelling technique followed by a fractionation of the tissue into subcellular components, chloroplasts could be identified as the predominant, if not exclusive, site of benzoic acid formation in A. chinensis. Experiments in vitro with chloroplasts and thylalkoids of N. officinale, H. macrophylla, and A. chinensis demonstrate the capacity of thylakoid membranes to catalyze the degradation of L-phenylalanine to benzoic acid. The results obtained upon stimultaneous incubation with [4'-3H]L-phenylalanine and [3-14C]cinnamic acid lead to the hypothesis that the reaction of L-phenylalanine to benzoic acid proceeds via a cinnamic acid pool which is different from that of soluble cinnamic acid.

Oxadiazole benzoic acid derivatives as herbicides

Abstract: New 2-(1,3,4-oxadiazole-2-yl) benzoic acids and salts and esters thereof, as well as certain 2-(2-oxazolyl) benzoic acids, salts and esters, having the formula: ##SPC1## Where X is nitrogen or C-R" (R" being hydrogen or methyl), R is phenyl or various substituents, and R' and the Y's are hydrogen or various substituents, are effective preemergence or postemergence herbicides, on various crops. The chemicals act selectively and are useful against purple nutsedge and in cranberry. Oxadiazoles of the invention may be made by reacting a benzhydrazide with phthalic anhydride to form a hydrazide which is cyclized by removal of the elements of water, using as a catalyst fuming sulfuric acid or dimethylformamide-sulfur trioxide complex.

Aminobenzoic acid diuretics. 7. 3-Substituted 4-phenyl-, 4-arylcarbonyl-, and 4-arylmethyl-5-sulfamoylbenzoic acids and related compounds.

Abstract: Various 4-substituted 3-alkylamino-, 3-alkoxy-, 3-alkylthio-, and 3-alkyl-5-sulfamoylbenzoic acids related to known aminobenzoic acid diuretics were synthesized and screened for their diuretic properties in dogs. The tabulated results from a 3-hr test period revealed that generally the diuretic profile and potency could be retained when 3-alkoxy, 3-alkylthio, and 3-phenethyl were substituted for the 3-alkylamino moiety. The high potency of several 3-alkoxy-, 3-alkylthio-, and 3-phenethyl-4-benzoyl-5-sulfamoylbenzoic acids confirmed previous suggestions that the apparent diuretic effect of 4- and 5-alkylamino-6-carboxy-3-phenyl-1,2-benzisothiazole 1,1-dioxides originates from the corresponding 4-benzoyl-5-sulfamoylbenzoic acid derivatives due to an existing equilibrium in plasma. 4-Benzoyl-5-sulfamoyl-3-(3-thenyloxy) benzoic acid (118) is among the most potent benzoic acid diuretics hitherto synthesized and shows significant diuretic activity in dogs at 1 mug/kg. The results obtained with different 3-substituted 4-phenyl-5-sulfamoylbenzoic acids supported the earlier concept regarding the steric influence of the 4-substituent on the diuretic potency of sulfamoylbenzoic acid diuretics.

Isoxazolyl benzoic acids

Abstract: Substituted or unsubstituted isoxazolyl benzoic acids, eg o-(4-methyl-3-phenylisoxazol-5-yl)benzoic acid, are prepared by dehydrating a corresponding 5-hydroxy-2-isoxazolin-5-yl benzoic acid, and are useful as hypolipidemic agents

Benzoic acid terminated oligoesters as melt flow modifiers of thermoplastic coatings and powders

Abstract: The application discloses a mixture of high molecular weight hard resins, such as polymethyl methacrylate, cellulose acetate butyrate and cellulose nitrate with low molecular weight benzoic acid terminated polyesters having a glass transition temperature in the range of -30° C. to 40° C. and a molecular weight in the range of 500 to 1500. The hard polyesters of this invention are obtained by the use of small diols and hard dibasic acids in addition to termination of the chain by the hardening component benzoic acid. Saturated linear dicarboxylic acids are used for less than half of the acid monomer content, on a molar basis, since these are softening components. The polyesters are used to lower the melting point and improve the flow of the high molecular weight polymers without excessively plasticizing these high molecular weight polymers to the point where they are noticeably softened at use temperatures. In contrast, the usual polyesters contain high amounts of saturated dicarboxylic acids and are terminated with saturated fatty acids. The mixture is useful for coatings applied in the form of a powder, a solution or a dispersion. Molded and cast articles can also be made from this mixture. As used herein, "thermoplastic" includes thermosetting resins which go through a thermoplastic flowable stage before becoming thermoset.

Benzoic acid amides for mycobacterium infections

Abstract: Benzoic acid amides characterized by the presence of a hydroxy or amino substituent in the phenyl ring, or an alkylated or acylated derivative thereof and by a heterocyclic group connected to the amide nitrogen atom through a hydrocarbon chain are antibacterial agents and in particular anti-tuberculosis agents. The compounds, of which N-[pyridyl-(2)-methyl]-2-hydroxybenzoic acid amide is a typical embodiment, are prepared by the reaction of an appropriately substituted benzoic acid, or derivative thereof, with an appropriate amine.

Pyridine carboxylic acid amides for mycobacterium infections

Abstract: Benzoic acid amides characterized by the presence of a nitro, cyano, trifluoromethyl, alkylsulfonyl, carboxy, carbalkoxy, amido or sulfonamido substituent in the phenyl ring and by the presence of a heterocyclic group connected to the amide nitrogen atom through a hydrocarbon chain are antibacterial agents and in particular antituberculosis agents. The compounds, of which N-(pyrid-2-yl-methyl)3,5-dinitrobenzoic acid amide is a typical embodiment, are prepared by the reaction of an appropriately substituted benzoic acid, or derivative thereof, with an appropriate amine.

Antilipidemic para-[aryl(alkyl or alkenyl)amino]-benzoic acid derivatives

Abstract: Novel para-[aryl(alkyl or alkenyl)amino]benzoic acids, esters, pharmaceutically acceptable salts and pharmaceutical compositions thereof and a method of lowering serum lipid levels in mammals therewith

Metal ions and complexes in organic reactions. Part XX. Copper-catalysed reactions of aromatic bromo-carboxylates with carbanions, giving oxo-acids, isocoumarins, and related products

Abstract: Depending upon choice of solvent and other conditions, copper-catalysed reactions of sodium o-bromobenzoate with sodium acetylacetonate gave o-(diacetylmethyl)benzoic acid (1), o-acetonylbenzoic acid (2), or 3-methylisocoumarin (3), whereas reactions with ethyl sodioacetoacetate gave compound (2) or (3) or o-(ethoxycarbonylmethyl)benzoic acid (5); analogously, the products o-CO2H·C6H4·CH(CO2Et)2[or (5)], o-CO2H·C6H4·CH(CN)·CO2H, and o-CO2H·C6H4·CH(CN)2 were obtained with the corresponding nucleophiles. Sodium 1-bromo-2-, 3-bromo-2-, and 8-bromo-1-naphthoate gave similar substitution products, including, in the first two cases, naphthopyranones. Nucleophilic substitution by the carbanions was ineffective with substrates not containing a carboxylate-salt group adjacent to the halogen. Reductive substitution of halogen competed to a varying extent. Copper could be introduced as metal, or CuI or CuII species, but the effective reaction intermediates are considered to be copper(II) complexes incorporating the halogeno-carboxylate substrate and the carbanionic nucleophile.

Organic Reactions in Molten Tetrachloroaluminate Solvents

Abstract: The use of molten salts as a medium for organic reactions has been known since organic chemistry’s beginning. The advantages such as short reaction times, ease of product recovery, possibility of high yields, and savings on solvent recovery together with the unusual physical properties (ionic liquids, high conductivity) shown by molten salts in comparison with other solvents opens new frontiers in the study of organic syntheses, separations, and mechanisms.

[35] Novobiocic acid synthetase

Abstract: Publisher Summary This chapter presents the assay procedure and properties of novobiocic acid synthetases. The antibiotic novobiocin consists of a noviose sugar (C ring), a coumarin moiety (B ring), and a substituted benzoic acid moiety (A ring) linked by a glycosidic and an amide bond. The enzyme forming an amide bond between the A ring and the B ring to produce novobiocic acid has been demonstrated in cell-free extracts of Streptomyces niveus. The reaction requires adenosine triphosphate (ATP), which indicates that an activation of the carboxyl group of the A ring is involved. The mode of activation has not been determined. Novobiocic acid synthetase can be assayed by measuring the rate of novobiocic acid formation. The quantity of novobiocic acid produced is measurable by spectrophotometric methods after extraction into n-butyl acetate. Substrates for the biosynthesis of novobiocin are most conveniently obtained by the hydrolysis of novobioein itself. Two hydrolysis routes are presented in the chapter.

The biosynthesis of benzoic acid in Bramley's Seedling apples infected by Nectria galligena Bres

Abstract: Radioactive benzoic acid was synthesized from glucose-14C and l -phenylalanine-14C in apples infected with Nectria galligena and in apples infused with protease extracted from tissue rotted by N. galligena. Phenylalanine ammonia-lyase (PAL) activity was rapidly induced in apples infused with the fungal protease but a lag phase occurred following inoculation with the pathogen. Production of benzoic acid was maximal approximately 3 days after maximum PAL production. Enzymes extracted from necrotic apple tissue converted phenylalanine to cinnamic and benzoic acids. P. expansum, a non-protease producing apple pathogen, did not induce either PAL activity or elicit benzoic acid accumulation in apples.

Glass-electrode measurements over a wide range of temperatures: The ionization constants (5–90°C) and thermodynamics of ionization of aqueous benzoic acid

Abstract: Glass-electrode measurements have been applied to the determination of the ionization constant of aqueous benzoic acid from 5 to 90°C, with the experimental procedure and calculations described in detail. The results lead to ΔHo=+60 cal-mole−1 for the standard enthalpy of ionization at 298°K, which is compared with ΔHo values from earlier investigations.

Role of the phytoalexin pisatin in controlling saprophytic fungal growth on pea leaves

Abstract: Czapek-Dox medium were transferred to flasks containing a benzoic acid solution (0'2 mgjml). Air containing 0, 2'5, 5'0, 7'5 and 10'0 %CO 2 was bubbled through the medium in the flasks. Following 12 h incubation the hyphae were removed from the flasks and the concentrations of benzoic acid remaining in the media were determined as previously described (Brown & Swinburne, 1973b). The rate of benzoic acid metabolism was apparently independent of the concentration of CO 2 in the aeration mixtures . It is believed that benzoic acid production arises indirectly from the shikimic acid pathway (Swinburne & Brown, 1975). The increased concentration of atmospheric CO 2 may result in the suppression of CO 2 release from reactions in this pathway and consequently partially inhibit the biosynthetic path.

Halophenoxy benzoic acid salts

Abstract: Metal salts and amine salts of 2-nitro-5-(halophaenoxy) benzoic acids comprise a class of compounds that are highly effective pre- and post-emergence herbicides.

Dynamic stereochemistry of imines and derivatives. Part V. Acid catalysis of E–Z imine interconversion

Abstract: The rate of E–Z isomerization in N-(α-phenyl-4-nitrobenzylidene)methylamine at 35° is shown to be markedly increased by trace amounts of benzoic acid. Dynamic n.m.r. experiments at higher temperature show that the isomerization rate is proportional to the acid concentration and enable activation parameters to be determined. CNDO/2 Calculations performed on the benzylideneammonium ion suggest that the C[graphic omitted] rotational barrier is ca.46 kcal mol–1, and high temperature n.m.r. studies on a related immonium perchlorate also indicate a high rotational barrier. It is suggested that benzoic acid promotes imine isomerization by nucleophilic addition to the C[graphic omitted] bond in the conjugate acid. The relevance of the rate of imine isomerization to the mechanism of the imine–peroxyacid reaction is discussed.

Synthesis of N-10-methyl-4-thiofolic acid and related compounds.

Abstract: Compound 21 (N10-methyl-4-thiofolic acid) and related compounds were prepared as potential inhibitors of the cofactor forms of tetrahydrofolate. The preparation of 2-acetylamino-4-(benzylthio)-6-chloro-5-nitropyrimidine (4) provided an intermediate that was allowed to react with methyl p-[(3-aminoacetonyl)methylamino]benzoate oxime (16). The oxime function of the resulting 6-substituted aminopyrimidine 6 was hydrolyzed to give the corresponding acetonylaminopyrimidine 7, which on reductive cyclization gave methyl p-[[[2-amino-4-(benzylthio)-7,8-dihydro-6-pteridinyl]methyl]methylamino]benzoate (9). This dihydropteridine was oxidized with potassium permanganate, and the product was treated successively with sodium hydrosulfide to replace the benzylthio group and with aqueous sodium hydroxide to hydrolyze the ester function to give p-[[(2-amino-3,4-dihydro-4-thioxo-6-pteridinyl)methyl]methylamino]benzoic acid (N10-methyl-4-thiopteroic acid, 12). Another route to 12 involved the interaction of 2,5-diamino-4,6-dichloropyrimidine (15) with 16 to give methyl p-[[(2-amino-4-chloro-7,8-dihydro-6-pteridinyl)methyl]methylamino]benzoate (13). Displacement of the chloro group of 13 with sodium hydrosulfide followed by the simultaneous air oxidation of the dihydropteridine ring and saponification of the ester group gave 12. After protection of the 2-amino and 4-thioxo moieties of 12, the resulting intermediate benzoic acid was coupled with diethyl L-glutamate. The product of this reaction was deblocked to give 21. Methylation of 21 gave the corresponding 4-(methylthio) derivative 22, which on reaction with hydrazine gave the 4-hydrazino analog 23 of methotrexate. Reduction of 12 and 21 with sodium hydrosulfite gave the dihydropteridines 24 and 25, respectively. The title compound was an excellent inhibitor of the growth of Streptococcus faecium ATCC 8043. However, this and related compounds were ineffective inhibitors of dihydrofolic reductase and showed no significant activity in either the KB cell culture screen or against L1210 leukemia cells in mice.

Toner powder for electrostatic images comprising epoxy resin

Abstract: Toner powders for developing electrostatic images are provided which contain in epoxy resin organic dye that, although in itself insoluble in the resin, is solubilized therein by one or more substances selected from the group consisting of complete esters and alkyl and aryl amides of o- and m-phthalic acid, carbonic acid, phosphoric acid, benzoic acid and benzenesulfonic acids and condensation products of formaldehyde with alkyl and aryl amides of benzenesulfonic acids.