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PubMed2006

Growth-induced incommensurability observed in the organic co-crystal hexamethylenetetramine resorcinol.

Co-crystals of hexamethylenetetramine and resorcinol were investigated by X-ray diffraction. The structure was refined in the superspace group Xmcm(0beta0)s0s, X=(1/2 1/2 0 1/2). In the average structure the resorcinol molecules are disordered between two orientations. The main effect of the modulation in the structure is a harmonic modulation of the occupation probabilities of the two orientations of the resorcinol molecule. However, the modulated order is not perfect and the resorcinol molecules remain partially disordered. Below 270 K the crystal undergoes a phase transition to a commensurately modulated structure with modulation vector q=(0 1/2 1/4) and superspace group X2/m(0betagamma)0s. The structure of the low-temperature phase could not be determined owing to the poor quality of the crystals affected by the reconstructive phase transition.

Crystallization↗
PubMed1983

Percutaneous absorption, blood levels, and urinary excretion of resorcinol applied topically in humans.

The absorption and metabolic disposition of 2% resorcinol applied topically in a hydroalcoholic vehicle was determined in three human subjects. The drug penetrated the skin at a rate of 0.37 micrograms/cm2/hour. After 2 weeks of bid application of 800 mg resorcinol to about 30% of body surface of each subject, an average of 1.64% of the dosage was being excreted in 24-hour urine specimens as the glucuronide or as the sulfate conjugate. There was no resorcinol in blood drawn at weeks 1, 2, 3, and 4, or nor were there any abnormalities in thyroid function or blood chemistries at weeks 2, 3, and 4. Resorcinol (2%) appears safe for topical use in humans.

Administration, Topical↗
PubMed1979

Metabolism of phenol and resorcinol in Trichosporon cutaneum.

Trichosporon cutaneum was grown with phenol or resorcinol as the carbon source. The formation of beta-ketoadipate from phenol, catechol, and resorcinol was shown by a manometric method using antipyrine and also by its isolation and crystallization. Metabolism of phenol begins with o-hydroxylation. This is followed by ortho-ring fission, lactonization to muconolactone, and delactonization to beta-ketoadipate. No meta-ring fission could be demonstrated. Metabolism of resorcinol begins with o-hydroxylation to 1,2,4-benzenetriol, which undergoes ortho-ring fission yielding maleylacetate. Isolating this product leads to its decarboxylation and isomerization to trans-acetylacrylic acid. Maleylacetate is reduced by crude extracts to beta-ketoadipate with either reduced nicotinamide adenine dinucleotide or reduced nicotinamide adenine dinucleotide phosphate as a cosubstrate. The enzyme catalyzing this reaction was separated from catechol 1,2-oxygenase, phenol hydroxylase, and muconate lactonizing enzyme on a diethyl-aminoethyl-Sephadex A50 column. As a result it was purified some 50-fold, as was the muconate-lactonizing enzyme. Methyl-, fluoro-, and chlorophenols are converted to a varying extent by crude extracts and by purified enzymes. None of these derivatives is converted to maleylacetate, beta-ketoadipate, or their derivatives. Cells grown on resorcinol contain enzymes that participate in the degradation of phenol and vice versa.

Adipates↗
PubMed1989

[5-Alkyl(C19-C25) resorcinols as regulators of succinate and NAD-dependent substrate oxidation by mitochondria].

The effect of 5-n-alkyl(C19-C25) resorcinols isolated from Azotobacter chroococcum on the oxidation of succinate and NAD-dependent substrates (glutamate, alpha-ketoglutarate, malate, pyruvate) by rat liver mitochondria was studied, using the polarographic technique. With succinate, the above resorcinol lipids activated to some extent the 2,4-dinitrophenol-decoupled mitochondrial respiration, but markedly suppressed it (up to 95%) in the presence of NAD-dependent substrates. The activating and inhibiting effects correlated with the resorcinol lipid/mitochondrial proteins ratio and were observed, when the lipid concentration in the incubation mixture ranged from 2.4.10(-4) to 6.0.10(-4) M. The most striking inhibiting effect was observed with alpha-ketoglutarate as substrate. The results obtained suggest that 5-n-alkyl(C19-C25) resorcinols should be regarded as rotenone type regulators of cell respiration.

Animals↗
PubMed1989

[Synchronous fluorescent determination of phenol and resorcinol using linear regression of multiwavelength data].

A method for simultaneous determination of phenol and resorcinol in mixtures using fluorimetry is developed by combining synchronous fluorescence technique with linear regression of multiwavelength data. The effect of solution pH and other mental variables was examined and the optimal condition for determination of phenol and resorcinol was established. The proposed method was applied to fluorescent assay of resorcinol based on preparation with recoveries of 97.18 ( +/- 2.42)% and 98.15 (+/- 2.70)% for phenol and resorcinol, respectively.

Phenols↗
PubMed1984

Structure activity relationships of resorcinol substituted ring systems.

Dopamine receptor agonist activity was evaluated using resorcinol derivatives of the following ring systems: dopamine, aminotetralin, indan, benzocycloheptane, octahydrobenzo(f)quinoline and octahydrobenzo[g]quinoline. The compounds were evaluated for biological activity using in vitro binding assays, anesthetized cat blood pressure and heart rate, cat cardioaccelerator nerve preparation and rotations of rats with unilateral denervation of the caudate nucleus. Resorcinol substitutions were chosen because one hydroxyl group corresponded to the alpha-conformer of dopamine and the second hydroxyl group corresponded to the beta-conformer of dopamine. Dopamine receptor activity was found primarily with derivatives of aminotetralin and octahydrobenzo[f]quinoline while the other ring systems yielded compounds which were quite inactive. The active resorcinol derivatives were found in the same ring systems where catechol substitution was active in ring positions corresponding to either the alpha- or beta-conformer of dopamine. Likewise in those ring systems where catechol substitution corresponding to the beta-conformer of dopamine were quite inactive, resorcinol substitution in these series was not favorable for activity. The ring systems requirements for alpha- and beta-adrenoceptor agonist activity did not follow the same structural pattern as found for dopamine receptor agonist activity.

Animals↗
PubMed1998

Reaction of Resorcinol with alpha,beta-Unsaturated Ketones.

Products of the acid-catalyzed reaction of resorcinol with alpha,beta-unsaturated ketones have been found to fall into two classes. The first type of product is illustrated by 4-(3,4-dihydro-7-hydroxy-2,4,4-trimethyl-2H-1-benzopyran-2-yl)-1,3-benzenediol, 1, formed in 91% yield by the reaction of resorcinol with 4-methyl-3-penten-2-one (mesityl oxide). The second type of product is illustrated by (C(2)-symmetric) 2,2'-spirobi(7-hydroxy-4,4-dimethylchroman),4, formed in 85% yield by the reaction of resorcinol with 2,6-dimethyl-2,5-heptadien-4-one (phorone). A number of examples of reactions leading, in quite good yields, to products analogous to 1are presented, as well as some reactions that fail. Flavan 1 is identical to the compound formed by the acid-catalyzed reaction of acetone with excess resorcinol. Compound 1 and a steroidal analogue of 1 have been found to be fluorescent.

Journal Article↗
PubMed1983

Determination of phenol in the presence of resorcinol applying substitution with excess bromine water; structure of the bromination products.

Bromination with a large excess of bromine results in the formation of a tetrabromo product for phenol and a pentabromo derivative for resorcinol. It is possible to determine the active bromine in the tetrabromo product after its isolation by filtration. This can also be done in the presence of resorcinol as its pentabromo derivative does not precipitate. The method gives good results (96-97% +/- 1%) for quantities of 8 mg and higher of phenol in the presence of a maximum of 25 mg resorcinol. From the 1H- and 13C-NMR spectra of the bromination products it could be concluded that they have a quinoidal structure.

Bromine↗
PubMed1980

Studies on the mutagenicity of resorcinol and hydroxy-3-(p-amino)anilino-6,N-[(p-amino)phenol]benzoquinone-monoimine-1,4 in Salmonella typhimurium.

The hair-dye coupler resorcinol and the oxidation product of p-phenylenediamine d resorcinol, hydroxy-3-(p-amino)anilino-6,N-[(p-amino)phenol]benzoquinonemonoimine-1.4, were tested for mutagenicity in the histidine-requiring mutants of Salmonella typhimurium (TA100, TA1535, TA1537, TA1538 and TA98). The investigations were carried out in the absence and presence of rat-liver homogenate induced by Aroclor 1254 and the components of the NADPH-generating system. There was no indication of mutagenic activity by these 2 compounds at any of the 8 concentrations used. The nuclear magnetic resonance spectrum of the reaction product of p-phenylenediamine and resorcinol was recorded and is in agreement with its chemical structure.

Mutagenicity Tests↗
PubMed1987

Comparative metabolism and excretion of resorcinol in male and female F344 rats.

Following oral administration, resorcinol was readily absorbed from the gastrointestinal tract, rapidly metabolized, and excreted by male and female rats. In both sexes, most of the dose of resorcinol (greater than 90%) was excreted in the urine within 24 hr after oral administration of 112 mg/kg, indicating little potential for bioaccumulation in animal tissues. Less than 3% of an oral dose was excreted in feces. An analysis of bile indicated that at least 50% of the dose excreted in bile undergoes enterohepatic circulation to be eventually excreted in urine. Little (less than 5%) of the parent compound was excreted in urine; most of the dose was in the form of three major and one minor metabolite. The relative amounts of metabolites excreted changed only slightly with time and dose administered. Approximately 70% of the total radioactivity in the urine of both sexes was in the form of a glucuronide conjugate. Female rats excreted a greater portion of the dose as a sulfate conjugate than males. Males excreted more of a diconjugate containing both sulfate and glucuronide groups. Repeated exposure to up to five daily doses resulted in no apparent alteration of the pattern of resorcinol absorption, metabolism, and excretion observed after a single dose.

Animals↗
PubMed1994

The impact of gelatin-resorcinol glue on aortic tissue: a histomorphologic evaluation.

PURPOSE: Although gelatin-resorcinol-formaldehyde glue has been used to treat acute aortic dissections for some time, concerns about formaldehyde's mutagenicity and carcinogenicity made it imperative to develop a new glue compound. Gelatin-dialdehyde glue was produced by omitting the formaldehyde component and replacing it with two less toxic aldehydes, glutaraldehyde and glyoxal. This study evaluated the histomorphologic effects of the new glue through in vivo use on the aortic tissue of domestic pigs. METHODS: Each animal's infrarenal aorta was glued around an implanted prosthesis. Histomorphologic evaluation was performed after operation after 1 and 4 weeks. RESULTS: The results demonstrated that the clinically observed tanning effect can be attributed primarily to the disintegration of the fiber texture, specifically collagenous, as well as smooth muscle fibers, and to the reciprocal alterations of the proteoglycan interstitial substance in the aortic wall. Macroscopic, microscopic, and electron microscopic analysis of the gluing process revealed an adequate healing process without any morphologically significant difference between formaldehyde and formaldehyde-free gelatin-resorcinol glue. CONCLUSIONS: Gelatin-dialdehyde glue is able to produce the same effects in the area of the aortic wall as the substantially more toxic gelatin-resorcinol-formaldehyde glue and thus could be recommended for clinical trials for treating acute aortic dissections thus far yielding excellent initial results.

Animals↗
PubMed2005

Properties of resorcinol-tannin-formaldehyde copolymer resins prepared from the bark extracts of Taiwan acacia and China fir.

Resorcinol-tannin-formaldehyde copolymer resins (RTF) were prepared by using the bark extracts of Taiwan acacia (Acacia confusa) and China fir (Cunninghamia lanceolata) to substitute part of the resorcinol. From the results, the content of reactive phenolic materials in Taiwan acacia and China fir bark extracts were 51.6% and 46.5%, respectively. Aromatic compounds were the main components in the bark extracts showed by FT-IR analysis. The conventional synthesis condition used for RF resin was certainly not suitable for the RTF copolymer resin. It should be formed the novolak RF prepolymer by reacting the resorcinol with formaldehyde at the first stage, and then the bark extracts added and underwent the copolymerization reaction under acidic condition at the second-stage. The RTF copolymer resins prepared had cold-setting capability. They had higher viscosity, shorter gel time as compared with the RF resin. The RTF copolymer resins could be carried out the gluing application immediately after the hardener was added and had bonding strength the same as RF resin. But the RTF copolymer resins had worse stability and shorter shelf life than RF resin.

Acacia↗
PubMed2005

Determination of the overlapping pKa values of resorcinol using UV-visible spectroscopy and DFT methods.

In this paper we determine the overlapping pK(a) values of resorcinol in water, applying a UV-Vis spectroscopic method that uses absorbance diagrams. On the other hand, in order to explain the pK(a) values obtained, we also investigate the molecular conformations and solute-solvent interactions of the resorcinate anions, using ab initio and density functional theory methods. Several ionization reactions and equilibria in protic solvents, which possess a high hydrogen-bond-donor capability, are proposed. The mentioned reactions and equilibria constituted the indispensable theoretical basis to calculate the acidity constants of resorcinol. Basis sets at the HF/6-31 + G(d) and B3LYP/6-31 + G(d) levels of theory were used for calculations. Tomasi's method was used to analyze the formation of intermolecular hydrogen bonds between the resorcinate anions and water molecules. In this way, it was determined that in alkaline aqueous solutions the monoanion and dianion of resorcinol are solvated with two and four molecules of water, respectively. The agreement between the experimentally determined pK(a) values and those reported in the literature demonstrates the applicability and accurateness of the spectroscopic method here used. On the other hand, the agreement between the experimental and theoretically calculated pK(a) values provides solid support for the acid-base reactions proposed in this work.

Hydrogen Bonding↗
PubMed2005

Studies on the riboflavin-resorcinol interaction in an aqueous medium and its pH dependence.

The equilibrium constants, K', for the formation of the molecular association complex between riboflavin and resorcinol in the pH range 6-8 were found to be in the range 5-25 mol(-1)dm(3) by difference absorption spectroscopy. The equilibrium constants from emission spectroscopy were estimated to be in the range 38-55 mol(-1)dm(3) over the same pH range. Both sets of K' show a remarkable dependence on pH. The equilibrium constants K(A) and K(B) describing the interaction of riboflavin with neutral and ionic forms of resorcinol, respectively, obtained by resolving K', shows that K(B) is much greater than K(A). Molecular modeling studies suggest a stacked conformation of the two components in the complexed form. The interaction energies obtained from modeling studies also suggest a stronger interaction between the ionic form of resorcinol and riboflavin.

Hydrogen-Ion Concentration↗
PubMed1999

Gelatin-resorcinol-formaldehyde-glutaraldehyde glue for sealing pulmonary air leaks during thoracoscopic operation.

BACKGROUND: Intraoperative pulmonary air leakage is one of the most troublesome complications in video-assisted thoracoscopic surgical procedures. We developed a sealing procedure using gelatin-resorcinol-formaldehyde-glutaraldehyde (GRFG) glue for pulmonary air leaks during such operations. METHODS: Formaldehyde-glutaraldehyde (FG) jelly is prepared by mixing FG fluid with 2.5% sodium carboxymethyl cellulose to make the FG fluid viscous. We performed an adhesion-strength test to determine the optimum ratio of gelatin-resorcinol mixture to FG jelly and then conducted an air leakage test on swine lung to compare the sealing effect between fibrin and GRFG glues. To study the histotoxicity of the GRFG glue, the sealant was applied to injured rabbit lung, and the rabbits were followed for 1 day to 188 days. For clinical studies, we developed an endosyringe to apply the GRFG glue on the target site during video-assisted thoracoscopic surgical procedures and used this technique in 21 patients with intraoperative air leaks. In addition, the side effects of GRFG glue application were studied in 52 patients in whom glue was used in several ways during lung operations. RESULTS: The results of the adhesion-strength test favored a 2:1 gelatin-resorcinol to FG ratio. The mean pressure required to produce air leakage was significantly higher with GRFG glue than with fibrin glue (p<0.001). No critical histologic damage was seen in the rabbit lung, and the glue persisted on the lung surface for 188 days after sealing. Clinical application of the glue in 21 patients resulted in complete stoppage of air leakage during operation and long afterward, except in 1 patient with a late-onset lung fistula. The FG jelly helped prevent glue spillage at the target site, regardless of angle. A transient rise in temperature up to 38.60C was observed as a side effect 7 days after operation in 5 (9.6%) of the 52 patients. CONCLUSIONS: A GRFG glue using FG jelly seals pulmonary air leaks effectively, simply, and safely during video-assisted thoracoscopic surgical procedures.

Animals↗
PubMed2005

Electrochemical oxidation of hydroquinone, resorcinol, and catechol on boron-doped diamond anodes.

The electrochemical oxidation of aqueous wastes polluted with hydroquinone, resorcinol, or catechol on boron-doped diamond electrodes has been studied. The complete mineralization of the organic waste has been obtained independently of the nature of each isomer. No aromatic intermediates were found during the treatment, and solely aliphatic intermediates (carboxylic acids C4 and C2, mainly) were detected in the three cases. Although as from the bulk electrolyses study no differences in the electrochemical oxidation of dihydroxybenzenes seem to exist, different voltammetric behavior between resorcinol and the other two isomers was obtained in the voltammetric study. Catechol and hydroquinone have a reversible quinonic form, and a cathodic reduction peak appears in their voltammograms. The characterization of the first steps in the electrochemical oxidation of the three dihydroxybenzenes showed the formation of a larger number of intermediates in the oxidation of catechol, although no carbon dioxide was detected in its oxidation. Conversely, the oxidation of resorcinol and hydroquinone lead to the formation of important concentrations of carbon dioxide. The nondetection of aromatic intermediates, even if small quantities of charge are passed, confirms that the oxidation must be carried out directly on the electrode surface or by hydroxyl radicals generated by decomposition of water.

Boron↗
PubMed2000

Inhibition of tyrosinase by flavonoids, stilbenes and related 4-substituted resorcinols: structure-activity investigations.

Several flavonoids, stilbenes and related 4-substituted resorcinols, obtained from Artocarpus incisus and other plants or synthesized, were tested for their inhibitory activity against tyrosinase. The structure-activity relationships suggested that specific natural or synthesized compounds having the 4-substituted resorcinol skeleton have potent tyrosinase inhibitory ability. Kinetic studies have indicated that specific compounds having the 4-substituted resorcinol skeleton exhibit competitive inhibition of the oxidation of DL-beta-(3,4-dihydroxyphenyl)alanine (DL-DOPA) by mushroom tyrosinase. These findings could lead to the design and discovery of new tyrosinase inhibitors.

Enzyme Inhibitors↗
PubMed1982

Catalysis of nitrosation in vitro and in vivo in rats by catechin and resorcinol and inhibition by chlorogenic acid.

Measurements were made of the effects of phenolic compounds, some of which are present in the human diet, on the nitrosation of proline by nitrite to give N-nitrosoproline (NPRO). In vitro, resorcinol, catechin, p-nitrosophenol and phenol were catalysts and chlorogenic acid an inhibitor; guaiacol showed a marginal catalytic effect. Both the catalytic and the inhibiting effects were dependent on pH and on the concentration of phenolic compounds; catalysis by resorcinol and catechin was increased at optimal ratios of [nitrite]: [phenolic compound]. Endogenous nitrosation was examined in vivo by co-administration of nitrite, proline and a phenolic compound to rats and by monitoring the amount of NPRO excreted in the urine. Under similar experimental conditions, the catalytic effects observed in vivo decreased in the same order as those observed in vitro: resorcinol greater than p-nitroso-phenol greater than catechin greater than phenol greater than or equal to guaiacol; chlorogenic acid acted as an inhibitor. Catalysis and inhibition of N-nitrosation in rats in vivo appears to occur via mechanisms similar to those in vitro, although the effects in vivo were smaller. The implications of our findings for the endogenous formation of N-nitroso compounds and for variations in exposure due to different dietary constituents in humans are discussed.

Animals↗