Showing papers on "Benzoic acid published in 1982"

The origin of urinary aromatic compounds excreted by ruminants. 3. The metabolism of phenolic compounds to simple phenols.

Abstract: Dietary phenolic cinnamic acids are hydrogenated in the side-chain, demethylated and dehydroxylated in the rumen and are responsible for the large urinary output of benzoic acid by ruminants. 2. Decarboxylation of phenolic acids to simple phenols is another reaction of the intestinal microflora and experiments were made to determine the extent of this reaction in the rumen of sheep. 3. In five experiments phenolic compounds, quinic acid or casein were infused into the rumen or abomasum of sheep and increments in urinary outputs of phenolic acids and phenols determined by thin-layer and gas-liquid chromatography. 4. Production of phenols was almost exclusively confined to reactions in the rumen. 5. Rumen administration of phenolic benzoic or phenylacetic acids which contained a 4-hydroxy substituent yielded large increments in urinary phenol outputs. Other phenolic benzoic and phenylacetic acids were not decarboxylated. Rumen decarboxylation of 4-hydroxy-3-phenylpropionic acid did not occur and decarboxylation of 4-hydroxycinnamic acids was slight. 6. Nearly half the tyrosine content of rumen-administered casein was excreted as p-cresol, a decarboxylation product of 4-hydroxyphenylacetic acid, p-Cresol was the principal phenol found in sheep urine. 7. Catechol and phenol were consistently found in sheep urine samples and p-ethylphenol, resorcinol, quinol, 4-methylcatechol, orcinol and pyrogallol were also found when suitable precursors were infused to the rumen. 8. It is concluded that p-cresol is a rumen metabolite of tyrosine. The other phenols found are microbial metabolites of phenolic precursors which are either widely distributed in plants such as 4-hydroxybenzoic, protocatechuic and vanillic acids or of more limited distribution such as the orcinol glycosides of some Ericaceous plants.

The origin of urinary aromatic compounds excreted by ruminants. 2. The metabolism of phenolic cinnamic acids to benzoic acid.

Abstract: 1. The extent to which phenolic derivatives of benzoic acid (seven); of phenylacetic acid (one); of 3-phenylpropionic acid (one) and of cinnamic acid (six) served as precursors of the urinary benzoic acid excreted by sheep was determined after administration as continuous drips via rumen or abomasal cannulas. 2. Phenolic derivatives of benzoic or of phenylacetic acid were not dehydroxylated to yield aromatic acids following administration via either route. 3. Rumen infusion of phenolic derivatives of both 3-phenylpropionic and cinnamic acids gave enhanced rumen concentrations of 3-phenylpropionic acid with negligible amounts of benzoic acid. Between 63 and 106% of the 2-, 3- or 4-hydroxy acids, of the 3,4-dihydroxy acids or of the 3-methoxy, 4-hydroxy acids infused were excreted in the urine as benzoic acid and a variable proportion, characteristic of the individual animal, of up to 20% of the dose as cinnamic acid. 4. Abomasal infusion of monohydroxy 3-phenylpropionic and cinnamic acids did not yield urinary benzoic acid increments. However, between 11 and 34% of abomasally-infused disubstituted phenolic cinnamic acids infused were excreted in the urine as benzoic acid due, it is postulated, to entero-hepatic circulation and microbial metabolism of the infused acids in the large intestine. 5. It is concluded that rumen microbial metabolism of dietary phenolic cinnamic acids to 3-phenylpropionic acid followed by its absorption and oxidation in the body tissues is responsible for the greater part of the benzoic and cinnamic acids found in ruminant urine.

Structure of a new crystal form of 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid (flufenamic acid)

Abstract: C14Ht0F3NO2, P2.Jc, a = 12.523 (4), b = 7.868(6), c = 12.874 (3)A, fl = 95.2 (2) ° , O,,, = 1.47 (4), D e = 1.47 Mg m -3, Z = 4. Final R = 0.074 for 2255 observed reflections. The carboxyl group and the phenyl ring bearing the carboxyl group are nearly coplanar whereas the two phenyl rings are inclined with respect to each other at 52.8 ° . The difference between the two polymorphs of flufenamic acid lies in the geometrical disposition of the [3-(trifluoromethyl)- phenyl]amino moiety with respect to the benzoic acid moiety. As in other fenamate structures, the carboxyl group and the imino N atom are connected through an intramolecular hydrogen bond; also, pairs of centrosymmetrically related molecules are connected through hydrogen bonds involving carboxyl groups.

The origin of urinary aromatic compounds excreted by ruminants 1. The metabolism of quinic, cyclohexanecarboxylic and non-phenolic aromatic acids to benzoic acid

Abstract: 1. The contribution of dietary constituents to the large urinary output of benzoic acid characteristic of ruminants and some herbivores is not well understood. 2. Methods for the analysis of quinic, cyclohexanecarboxylic, benzoic, phenylacetic, 3-phenylpropionic and cinnamic acids in urine and in rumen fluids were developed. 3. The urinary output of aromatic acids by sheep given seven-rations was determined: benzoic acid output varied between 2.8 and 7.8 g/d; phenylacetic acid output between 0.16 and 1.3 g/d; cinnamic acid between 0.08 and 0.25 g/d and small amounts of 3-phenylpropionic acid were found in some samples. 4. Increments in urinary aromatic acid excretion were determined when the acids listed in paragraph 2 were infused via rumen or abomasal cannulas. 5. When cyclohexanecarboxylic acid was infused 40% of the dose was excreted as urinary benzoic acid after either route of infusion. Quinic acid was completely metabolized in the rumen; following rumen infusion between 16 and 53% of the infused acid was recovered as urinary benzoic acid; none was so recovered after abomasal infusion. 6. Urinary recoveries of rumen- and abomasally-infused aromatic acids were: benzoic acid 90 and 88% respectively as benzoic acid, phenylacetic acid 78 and 83% respectively as phenylacetic acid, 3-phenylpropionic acid 96 and 105% respectively as benzoic acid and cinnamic acid, 70 and 70% respectively as benzoic acid. 7. The concentration of aromatic acids in rumen fluid varied with time after feeding: cyclohexanecarboxylic acid was maximal (7 mg/l) 1 h after feeding, benzoic acid was always a minor component (0.5 +/- 0.5 mg/l), phenylacetic acid varied between 0 and 35 mg/l and 3-phenylpropionic acid between 25 and 47 mg/l. Cinnamic acid was not found in rumen fluid but on rumen infusion of this acid the concentration of 3-phenylpropionic acid in rumen fluid increased by 10 mg/l rumen fluid per g infused per d. 8. The incomplete metabolism of quinic and cyclohexanecarboxylic acids to urinary benzoic acid is discussed. It is concluded that the principal dietary precursors of urinary benzoic acid in ruminants are compounds yielding 3-phenylpropionic acid on microbial fermentation in the rumen. The small amount of cinnamic acid characteristic of ruminant urine arises as an intermediate in the beta-oxidation of 3-phenylpropionic acid in the body tissues.

Thermodynamics of complexation of lanthanides by benzoic and isophthalic acids

Abstract: The thermodynamic parameters (..delta..G, ..delta..H, and ..delta..S) of formation of the 1:1 complexes between lanthanide cations and benzoate and isophthalate anions were determined by potentiometric and calorimetric titrations in aqueous solutions of 0.10 M (NaClO/sub 4/) ionic strength. The values for the benzoate complexes agreed with the general relationships for alkyl monocarboxylate complexation (e.g., log ..beta../sub 101/ vs. pK/sub a/). Even though the isophthalate complexes must also involve interaction between the metal and a single carboxylate group, the thermodynamic parameters differ from those for benzoate complexing. It is proposed that the enhanced stability of the isophthalate complexes is related to polarization of electronic charge from the unbound carboxylate group through the ..pi.. system of the phenyl ring to the bonding carboxylate.

Synthesis and Properties of a New Polyesterimide from a Forest Product

Abstract: Polyesterimide offers a class of resin which combines the advantage of high temperature stability with ease of process-ability. Gum rosin, the exudate of pine trees, has been developed as the raw material for preparation of polyesterimide. Abietic acid of rosin reacts readily with maleic anhydride to form the Diels-Alder adduct, which reacts with p-amino benzoic acid to produce a dicarboxylic acid containing an internal imide group. The dicarboxylic acid reacts with diethylene glycol under melt polycondensation at higher temperature (260–300°C)to produce polyesterimide. The polymer is found to be soluble in highly polar solvents. The polymer is amorphous and of low molecular weight. Thermal stability of the polymer has been characterized, and the polymer was found to be thermostable.

Anionic compounds based on modified novolak-oxyalkylates, their preparation and their use as foam-free surface-active agents

Abstract: The invention relates to novolak oxyalkylate mixed esters which, on the one hand, contain benzoyl and/or naphthoyl radicals and, on the other hand, contain maleic acid and/or sulfosuccinic acid half-ester groups. They are obtained by reacting novolak oxyalkylates with benzoic acid and/or naphthoic acid or with its anhydride or chloride on the one hand and maleic anhydride on the other hand and, if appropriate, reacting the maleic acid half-ester groups with sulfites to give sulfosuccinic acid half-ester groups. These compounds are highly suitable for use as dispersing agents for the preparation of low-foam dispersions of pigments, dyestuffs and other agents and as emulsifying, leveling and dyeing auxiliaries.

Mechanistic studies in strong acids. VIII. Hydrolysis mechanisms for some thiobenzoic acids and esters in aqueous sulfuric acid, determined using the excess acidity method

Abstract: The excess acidity method has been applied to hydrolysis rate data, obtained as a function of medium composition, for four thiobenzoic acids, thioacetic acid, eight ethyl thiolbenzoates, and eight ethyl thionbenzoates in aqueous sulfuric acid. The mechanistic behaviour thus revealed has both similarities to and differences from that of a typical ester like ethyl benzoate, which gives benzoic acid by an A-2 reaction involving two water molecules in weak acid, and by A-1 acylium ion formation in strong acid. The thioacids follow this behaviour, except that the A-2 process involves three water molecules, and that the mechanistic changeover occurs in 60% rather than 80% acid. The A-2 process for the ethyl thiolbenzoates is slow; the major hydrolysis mechanism is acylium ion formation, not in an A-1 reaction but by a concerted A-SE2 process involving both proton transfer to sulfur and carbon–sulfur bond breaking. The major proton transfer agent is the undissociated sulfuric acid molecule. The thionbenzoate est...

Pyrolysis of Chlorogenic Acid and Rutin

Abstract: Chlorogenic acid and rutin, major polyphenols in tobacco, were pyrolysed with a furnace type pyrolyser connected directly to a gas chromatograph and 22 compounds (including catechol, benzoic acid, 4-vinylcatechol and quinic acid γ-lactone) from Chlorogenic acid and 24 compounds [including catechol, 5-methyl-2-furaldehyde, 4-methylcatechol and 1, 6-anhydroglucopyranose (levoglucosan)] from rutin have been identified as pyrolysis products. The gas chromatograph was also replaced by a capillary cold trap which allowed collection of the pyrolysis products prior to a quantitative determination using an internal standard. Comparison of the pyrolysis products produced from chlorogenic acid or rutin with those derived from tobacco and analysis of the pyrolysis products from a mixture of tobacco and chlorogenic acid or rutin indicated that fairly large proportions of catechol, 4-vinylcatechol and quinic acid γ-lactone produced by the pyrolysis of tobacco may originate from endogenous chlorogenic acid.

Electrolytic synthesis of aryl alcohols, aryl aldehydes, and aryl acids

Abstract: Disclosed is a method of synthesizing compounds chosen from the group consisting of benzyl alcohol, benzaldehyde, benzoic acid, phenoxy benzyl alcohol, phenoxy benzaldehyde, phenoxy benzoic acid, and mixtures thereof by providing a composition of a current carrying component, such as a fluoroborate salt or a tetraethylammonium salt, a solvent, and a methyl aryl compound in contact with an anode and cathode. The solvent is reduced at the cathode and the methyl substituted aryl at the anode whereby to form product. According to an alternative exemplification of the invention, the anode and cathode are separated by a permionic membrane and a source of oxygen is provided in contact with the cathode and the permionic membrane.

Some observations on the urinary excretion of glycine conjugates by laboratory animals.

Abstract: 1. An isotope dilution assay has been developed for measuring the amount of conjugated glycine present in urine. The average daily excretion of conjugated glycine by male and female mouse, rat, guinea-pig and rabbit has been determined.2. The glycine conjugates excreted by the four species have been identified. All species excreted only benzoylglycine and phenylacetylglycine.3. The metabolism of [carboxy-14C]benzoic acid and [1-14C]phenylacetic acid has been investigated in the Sprague-Dawley rat. When administered over a range of concn. from 10 μg/kg to 1 g/kg, benzoic acid is converted to hippuric acid while phenylacetic acid is converted to phenylacetylglycine and phenylacetylglutamine.4. Neither the rate of excretion nor the composition of the urinary metabolites arising from each acid is changed when low doses of one acid are co-administered with a high dose of the other.5. The origin of the conjugated benzoic and phenylacetic acids is discussed.

Alkanol alkoxylate preparation

Abstract: A process for the preparation of alkanol alkoxylates, useful as nonionic surfactants, comprises steps for alkoxylating one or more alkanols having carbon number in the range from 8 to 18 by reaction with one or more alkylene oxides having carbon number in the range from 2 to 4 under alkaline pH and in the presence of one or more soluble compounds of calcium, and neutralizing the resulting alkoxylation mixture by addition thereto of an acid selected from the group consisting of propionic acid, benzoic acid, and mixtures thereof. The products are characterized by a single liquid phase of low viscosity.

The Schmidt reaction of anthraquinones

Abstract: Schmidt reaction (sodium azide/sulfuric acid) of 1,5- and of 1,8-dichloroanthraquinones gives, in each case, both of the theoretically possible lactams (2,3,5,6-dibenzoazepin-4,7-diones). Two of the four theoretically possible lactams have been identified from Schmidt reaction of 1- and 2-chloroanthraquinones respectively. Methods used include: (a) preferential hydrolysis of one lactam and identification of the isomeric aminoanthraquinone formed on cyclodehydration of the resulting amino acid; (b) identification of the isomeric aminoanthraquinone(s) formed on direct treatment of a lactam (or mixture of lactams) by sulfuric acid; (c) cleavage by potassium tert-butoxide of the amino acid formed by preferential hydrolysis of one lactam and identification of the resulting benzoic acid as its methyl ester.

The kinetic mechanism of the major form of ox kidney aldehyde reductase with d-glucuronic acid

Abstract: The steady-state kinetics of the major form of ox kidney aldehyde reductase with d-glucuronic acid have been determined at pH7. Initial rate and product inhibition studies performed in both directions are consistent with a Di-Iso Ordered Bi Bi mechanism. The mechanism of inhibition by sodium valproate and benzoic acid is shown to involve flux through an alternative pathway.

Human Metabolism of Bis(2-ethylhexyl)phthalate

Abstract: To study the human metabolism of bis (2-ethylhexyl)-phthalate (DEHP) urine samples were analyzed from non-uremic psoriatic patients, uremic patients undergoing hemodialysis treatments and patients undergoing cardiac bypass surgery using High Performance Liquid Chromatography (HPLC). The urine of dialyzed non-uremic patients contained phthalic acid, mono (2-ethylhexyl) phthalate and bis (2-ethylhexyl) phthalate. Other compounds identified were p-hydroxy benzoic acid, m-hydroxy benzoic acid, o-hydroxy hippuric acid, o-hydroxy benzoic acid and benzoic acid, which may be either diet dependent normal urinary constituents or metabolites of bis (2-ethylhexyl) phthalate. The levels of phthalic acid and bis (2-ethylhexyl) phthalate found in the urine of patients who were on total body oxygenators containing a membrane during cardiac bypass surgery were comparable to levels obtained from non-uremic psoriatic patients. Significant levels of phthalic acid were detected in the urine of the uremic patients stu...