salicylates and phenyl-salicylate

The efficiency of counterion affinity towards ionic micelles is often described in terms of the degree of counterion binding (β

Topics: Cations; Micelles; Molecular Probes; Salicylates

A new method, based upon semi-empirical kinetic approach, for the determination of ion exchange constant for ion exchange processes occurring between counterions at the cationic micellar surface is described in this review article. Basically, the method involves a reaction kinetic probe which gives observed pseudo-first-order rate constants (k(obs)) for a nucleophilic substitution reaction between the nonionic and anionic reactants (R and S) in the presence of a constant concentration of both reactants as well as cationic micelles and varying concentrations of an inert inorganic or organic salt (MX). The observed data (k(obs), versus [MX]) fit satisfactorily (in terms of residual errors) to an empirical equation which could be derived from an equation explaining the mechanism of the reaction of the kinetic probe in terms of pseudophase micellar (PM) model coupled with another empirical equation. This (another) empirical equation explains the effect of [MX] on cationic micellar binding constant (K(S)) of the anionic reactant (say S) and gives an empirical constant, K(X/S). The magnitude of K(X/S) is the measure of the ability of X(-) to expel S(-) from a cationic micellar pseudophase to the bulk aqueous phase through ion exchange X(-)/S(-). The values of K(X/S) and K(Y/S) (where Y(-) is another inert counterion) give the ion exchange constant, K(X)(Y) (=K(X)/K(Y) where K(X) and K(Y) represent cationic micellar binding constants of X(-) and Y(-), respectively). The suitability of this method is demonstrated by the use of three different reaction kinetic probes and various MX.

Topics: Cations; Cetrimonium; Cetrimonium Compounds; Chemical Phenomena; Hydrogen-Ion Concentration; Kinetics; Micelles; Models, Chemical; Salicylates

A toxicologic and dermatologic review of phenyl salicylate when used as a fragrance ingredient is presented.

Topics: Animals; Consumer Product Safety; Dose-Response Relationship, Drug; Humans; Mutagens; Perfume; Risk Assessment; Salicylates; Skin; Skin Absorption; Skin Irritancy Tests; Skin Tests; Teratogens; Toxicity Tests

The polylactic acid composite films were successfully fabricated via the technique of solvent casting using cellulose acetate (20%, wt) as the reinforcing material and phenyl salicylate as the ultraviolet (UV) absorbent and antibacterial agent. Polylactic acid-cellulose acetate-phenyl salicylate composite films displayed complete absorption effect at the region of UV-C (280-100 nm) and UV-B (315-280 nm), and more than 95% UV absorption effect at the region of UV-A (400-315 nm). These results indicate that the UV shielding performance of the composite films could be significantly improve by addition of phenyl salicylate. Moreover, the addition of 20% phenyl salicylate could improve the steam resistance, mechanical properties and thermal stability of the films, and the composite films had also better antibacterial activity against Escherichia coli. The composite films could reduce the decay rate of fresh lilies and extend their storage time. The degradation characteristics of the films were explored in the natural environment and the laboratory level, which provided application prospect for the development of degradable food packaging materials with anti-ultraviolet and anti-bacteria effect.

Topics: Anti-Bacterial Agents; Cellulose; Escherichia coli; Food Packaging; Polyesters; Salicylates

The present study is focused on the effect of the TTABr/MX/H2O-nanoparticles on the rate of piperidinolysis of ionized phenyl salicylate where TTABr represents tetradecyltrimethylammonium bromide and MX = NaCl, NaBr and CnH2n+1CO2Na with n = 4, 5, 6 and 7. Pseudo-first-order rate constant for the piperidinolysis of ionized phenyl salicylate at 35°C and constant concentration [PSa(-)]T = 0.2 mM, [Pip]T = 0.1 M, [NaOH] = 30 mM, [TTABr]T and different [MX] follow an empirical relationship which gives two empirical constant, (X)kcat and K(X/S). The value of relative counterion (X) binding constant, RX(Br) were calculated from the relationship; RX(Br) = (X)kcat/(Br)kcat. The values of RX(Br) for X = C4H9CO2(-), C5H11CO2(-), C6H13CO2(-), and C7H15CO2(-) are increasing with increase in the number of alkyl chain of counterion X.

Topics: Anions; Bromates; Catalysis; Cations; Kinetics; Nanoparticles; Salicylates; Sodium Chloride; Sodium Compounds; Trimethyl Ammonium Compounds

Salicylates are used as fragrance and flavor ingredients for foods, as UV absorbers and as medicines. Here, we examined the hydrolytic metabolism of phenyl and benzyl salicylates by various tissue microsomes and plasma of rats, and by human liver and small-intestinal microsomes. Both salicylates were readily hydrolyzed by tissue microsomes, predominantly in small intestine, followed by liver, although phenyl salicylate was much more rapidly hydrolyzed than benzyl salicylate. The liver and small-intestinal microsomal hydrolase activities were completely inhibited by bis(4-nitrophenyl)phosphate, and could be extracted with Triton X-100. Phenyl salicylate-hydrolyzing activity was co-eluted with carboxylesterase activity by anion exchange column chromatography of the Triton X-100 extracts of liver and small-intestinal microsomes. Expression of rat liver and small-intestinal isoforms of carboxylesterase, Ces1e and Ces2c (AB010632), in COS cells resulted in significant phenyl salicylate-hydrolyzing activities with the same specific activities as those of liver and small-intestinal microsomes, respectively. Human small-intestinal microsomes also exhibited higher hydrolyzing activity than liver microsomes towards these salicylates. Human CES1 and CES2 isozymes expressed in COS cells both readily hydrolyzed phenyl salicylate, but the activity of CES2 was higher than that of CES1. These results indicate that significant amounts of salicylic acid might be formed by microsomal hydrolysis of phenyl and benzyl salicylates in vivo. The possible pharmacological and toxicological effects of salicylic acid released from salicylates present in commercial products should be considered.

Topics: Animals; Carboxylic Ester Hydrolases; Flavoring Agents; Humans; Hydrolysis; Intestine, Small; Liver; Male; Microsomes; Rats; Rats, Sprague-Dawley; Salicylates

Disinfection of swimming pool water is essential to inactivate pathogenic microorganisms. However chlorine based disinfectants, the most commonly used, are known to lead to the formation of disinfection by-products (DBPs), some of which have been associated with adverse health effects. Precursors of DBPs include the organic matter present in the water used to fill the swimming pool, human body fluids and personal care products (PCPs) used by swimmers and bathers. The increased use, in the last years, of PCPs lead to an increased concern about the fate of PCPs in swimming pool waters and potential health risks of formed DBPs. In this study, the chemical transformations of two salicylates, benzyl salicylate (BzS) and phenyl salicylate (PS), incorporated in several PCPs, in chlorinated water were investigated. High-performance liquid chromatography (HPLC) with UV-diode-array detection (HPLC-UV-DAD) was used to follow the reaction kinetics and HPLC with mass spectrometry (HPLC-MS) was used to tentatively identify the major transformation by-products. Under the experimental conditions used in this work both salicylates reacted with chlorine following pseudo-first order kinetics: rate constant k = (0.0038 ± 0.0002) min(-1) and half-life t1/2 = (182 ± 10) min for BzS and rate constant k = (0.0088 ± 0.0005) min(-1) and half-life t1/2 = (79 ± 4) min for PS (mean ± standard deviation). The reactions of the two salicylates in chlorinated water led to the formation of DBPs that were tentatively identified as mono- and dichloro- substituted compounds. Most probably they result from an electrophilic substitution of one or two hydrogen atoms in the phenolic ring of both salicylates by one or two chlorine atoms.

Topics: Chlorine; Chromatography, High Pressure Liquid; Disinfectants; Disinfection; Mass Spectrometry; Salicylates; Swimming Pools; Water Pollutants, Chemical; Water Pollution, Chemical

The temperature dependences of α relaxation time τ(α)(T) of three glass-forming liquids (salol, o-terphenyl, and α-picoline) were investigated by a depolarized light scattering technique. A detailed description of τ(α)(T) near T(A), the temperature of the transition from the Arrhenius law at high temperatures to a non-Arrhenius behavior of τ(α)(T) at lower temperatures, was done. It was found that this transition is quite sharp. If the transition is described as switching from the Arrhenius law to the Vogel-Fulcher-Tammann law, it occurs within the temperature range of about 15 K or less. Most of the known expressions for τ(α)(T) cannot describe this sharp transition. Our analysis revealed that this transition can be described either as a discontinuous transition in the spirit of the frustration-limited domain theory [D. Kivelson, G. Tarjus, X. Zhao, and S. A. Kivelson, Phys. Rev. E 53, 751 (1996)], implying a phase transition, or by a phenomenological expression recently suggested [B. Schmidtke, N. Petzold, R. Kahlau, M. Hofmann, and E. A. Rössler, Phys. Rev. E 86, 041507 (2012)], where the activation energy includes the term depending exponentially on temperature.

Topics: Glass; Light; Phase Transition; Picolines; Salicylates; Scattering, Radiation; Temperature; Terphenyl Compounds

The values of the relative counterion (X) binding constant R(X)(Br) (=K(X)/K(Br), where K(X) and K(Br) represent cetyltrimethylammonium bromide, CTABr, micellar binding constants of X(v-) (in non-spherical micelles), v = 1,2, and Br(-) (in spherical micelles)) are 58, 68, 127, and 125 for X(v-) = 1(-), 1(2-), 2(-), and 2(2-), respectively. The values of 15 mM CTABr/[Na(v)X] nanoparticles-catalyzed apparent second-order rate constants for piperidinolysis of ionized phenyl salicylate at 35 °C are 0.417, 0.488, 0.926, and 0.891 M(-1) s(-1) for Na(v)X = Na1, Na2 1, Na2, and Na2 2, respectively. Almost entire catalytic effect of nanoparticles catalyst is due to the ability of nonreactive counterions, X(v-), to expel reactive counterions, 3(-), from nanoparticles to the bulk water phase.

Topics: Anions; Catalysis; Cetrimonium; Cetrimonium Compounds; Kinetics; Micelles; Nanoparticles; Piperidines; Salicylates; Surface-Active Agents; Water

Nosemosis type C caused by the microsporidium Nosema ceranae is one of the most widespread of the adult honey bee diseases, and due to its detrimental effects on both strength and productivity of honey bee colonies, an appropriate control of this disease is advisable. Fumagillin is the only veterinary medicament recommended by the World Organization for Animal Health (OIE) to suppress infections by Nosema, but the use of this antibiotic is prohibited in the European Union and few alternatives are available at present to control the disease. In the present study three therapeutic agents (Nosestat®, Phenyl salicylate and Vitafeed Gold®) have been tested to control N. ceranae infection in honey bee colonies, and have been compared to the use of fumagillin. None of the products tested was effective against Nosema under our experimental conditions. Low consumption of the different doses of treatments may have had a strong influence on the results obtained, highlighting the importance of this issue and emphasizing that this should be evaluated in studies to test therapeutic treatments of honey bee colonies.

Topics: Animals; Antifungal Agents; Bees; Beta vulgaris; Cyclohexanes; Fatty Acids, Unsaturated; Formates; Iodine; Microsporidiosis; Nosema; Phytotherapy; Plant Extracts; Salicylates; Sesquiterpenes

Antimycobacterial activity of phenyl salicylates (salols) was studied in connection with antituberculotic activity of salicylic derivatives. Phenyl salicylates are esters. Our attention was previously oriented on amides. Phenyl salicylates (salols) represent a new group of antimycobacterial compounds. They are less active than the corresponding amides. The most active compound in the group under study is substituted on phenyl in the salicyl moiety with a 4-methoxy group. The study reports a new item of information about antimycobacterial salicylic derivatives.

Topics: Antitubercular Agents; Mycobacterium; Salicylates

We report the investigation of glass-forming salol upon different courses of the temperature changes from liquid to glass state and back using FT-IR spectroscopy measurements in the wide spectral and temperature ranges. The formation of the ordered clusters in supercooled liquid salol has been observed at 250 K. When the temperature is decreased further to 11 K these ordered clusters become an element of the glass structure. With increasing temperature to 270 K through the glass transition noticeable evolutions of the IR spectrum occurs up till the ordered clusters are developed into crystal. So produced crystal melts in the temperature range 300-310 K, that corresponds to the melting temperature of the metastable phase (Tmelt=302 K) . Thus, the crystalline structure of the ordered clusters corresponds to the structure of metastable phase and is monoclinic.

Topics: Computer Simulation; Glass; Models, Chemical; Phase Transition; Salicylates; Spectroscopy, Fourier Transform Infrared; Temperature

To investigate the influence of the interfacial area and the emulsifier lecithin on the degradation rate of drugs prone to hydrolysis in parenteral lipid O/W emulsions we measured the degradation kinetics of phenyl salicylate in systems consisting of Miglyol as oil, buffered and isotonized aqueous phase and lecithin as emulsifier. Two-layer oil over water systems and emulsions of different oil droplet diameters and emulsifier contents were tested and a kinetic model was developed to interpret the results. The measurements showed a complex influence of interfacial area and liposomal concentration on the hydrolysis of phenyl salicylate. The interface between oil and water does not act as a diffusion barrier for phenyl salicylate, neither without nor with an interfacial layer of emulsifier. However, the presence of the layer and the formation of liposomes by the emulsifier lead to an overall acceleration of the hydrolysis. Three effects, partially counteracting each other, could be distinguished: the increase of phenyl salicylate concentration in the aqueous phase with increasing emulsifier concentration, the acceleration of hydrolysis with increasing interfacial area and the protection from hydrolysis by incorporation of phenyl salicylate into the emulsifier liposomes.

Topics: Algorithms; Buffers; Chemical Phenomena; Chemistry, Physical; Chromatography, High Pressure Liquid; Electrochemistry; Emulsions; Hydrogen-Ion Concentration; Hydrolysis; Kinetics; Liposomes; Oils; Osmotic Pressure; Pharmaceutical Preparations; Phosphatidylcholines; Photons; Salicylates; Solubility; Spectrum Analysis; Surface Tension; Water

Mesoporous silica phases, with uniform pores of dimensions in the 2-30 nm range, offer a uniquely well-defined environment for the study of the effects of two-dimensional spatial confinement on the properties of glass-forming liquids. We report observations by differential scanning calorimetry of the vitrification of o-terphenyl (OTP), salol, and glycerol in hexagonal mesoporous silica (MCM-41 and SBA-15) in a wide range of pore sizes from 2.6 to 26.4 nm. In agreement with previous studies, where a controlled porous glass is used as a solid matrix, the glass transition temperature for o-terphenyl diminishes with decreasing pore size. In contrast to OTP, glycerol shows a gradual increase in glass transition temperature, while in salol a slight reduction of glass transition temperature is observed, followed by an increase, which results in glass transition temperature indistinguishable from that of the bulk for the smallest pores. These results are discussed in terms of liquid-surface interactions in an interfacial layer, monitored by Fourier-transformed infrared spectroscopy in the study. The hydrogen bonding with silica surface silanols dominates the glass transition trends observed in salol and glycerol.

Topics: Calorimetry, Differential Scanning; Chemistry, Physical; Glass; Glycerol; Hydrogen Bonding; Models, Chemical; Molecular Conformation; Salicylates; Silanes; Silicon Dioxide; Spectroscopy, Fourier Transform Infrared; Temperature; Terphenyl Compounds; Thermodynamics; Transition Temperature

The effect of photostabilization of azadirachtin-A (Aza-A) was examined in solutions when exposed to UV radiation, in the presence of four structurally different UV absorbers namely, p-aminobenzoic acid, 2,4-dihydroxybenzophenone, 4,4'-dihydroxybenzophenone and phenyl salicylate. The percentages of Aza-A recovered from the solutions after 6 h exposed to UV radiation in the presence and absence of UV absorbers indicated that the order of stabilization of Aza-A by these absorbers was similar to that obtained in the solid phase experiments in accordance with our previous observations. It is observed that the addition of phenyl salicylate in Aza-A (in 1:1 mole ratio) provides the excellent photostabilization of Aza-A molecule in solid phase as well as in solution among the four absorbers studied.

Topics: 4-Aminobenzoic Acid; Azadirachta; Benzophenones; Drug Stability; Limonins; Pest Control, Biological; Photolysis; Salicylates; Solutions; Ultraviolet Rays

The mutans group of streptococci is considered to play a key role in the etiology of dental caries. We have evaluated the ability of different substances to prevent dental plaque formation without affecting Streptococcus sobrinus viability. Viable organisms were detected as CFU/mL in agar plates and bacterial adherence was assessed by dry weight. We studied 23 compounds and we demonstrated that phenyl salicylate, phenylmercuric nitrate and potassium iodate are more effective to inhibit adhesion without showing antibacterial activity.

Topics: Anti-Infective Agents, Local; Bacterial Adhesion; Colony Count, Microbial; Dental Plaque; Iodates; Phenylmercury Compounds; Potassium Compounds; Salicylates; Streptococcus sobrinus

The stability and degradation pathways of phenyl salicylate (PS) in 50 v/v% aqueous ethanol were investigated over the pH range of 3.2-8.4. The experiments were performed at three different temperatures (5, 23 and 50 degrees C) for four months by the use of high performance liquid chromatography. The degradation of PS was observed as a pseudo first-order kinetics not only in the alkaline region but in the acidic region and shown to proceed via transesterification (k1) and hydrolysis (k2) processes. The transesteified product, ethyl salicylate (ES), further underwent hydrolysis (k3) (k1 > k2 > k3). On the basis of kinetic studies, it was found that the degradation rate of PS decreased with decreasing pH and temperature. The half-lives of PS at pH 6.3 were 6.6 d (50 degrees C), 178 d (23 degrees C) and 2934 d (5 degrees C), respectively, and PS was stable at below ca. pH 4. On the other hand, PS in 100% ethanol also underwent the breakdown to ES by k1 process and its half-lives were 2.5 d (50 degrees C), 31.5 d (23 degrees C) and 257 d (5 degrees C), respectively. The present results is useful for the integrity of pharmaceutical formulations and delivery profiles.

Topics: Chromatography, High Pressure Liquid; Drug Stability; Ethanol; Hydrogen-Ion Concentration; Preservatives, Pharmaceutical; Salicylates; Solutions; Solvents; Temperature; Water

Several observations have indicated that house-dust mites (HDM) play an important role in allergic diseases. Thus, the primary form of treatment should aim at reducing exposure to HDM for these patients. Allergen-avoidance measures in homes have been demonstrated to be beneficial in decreasing the risk of sensitization, severity of symptoms, bronchial reactivity, and basophil sensitivity. Various chemical methods, as well as physical measures, have been tried to eliminate mite allergens from house dust. However, none have gained wide acceptance because of the lack of effectiveness and safety, and the high cost. It is clear that new approaches are required for effective long-term control of HDM allergens. This study compared the acaricidal activities of phenyl salicylate, tea leaf extract (high tannic acid content), and essential oils (eucalyptus and laurel) with that of benzyl benzoate. The contact, short-duration persistence, and residual effects of various concentrations of these chemicals and benzyl benzoate were assessed in laboratory conditions with specially designed wells. Our data suggest that benzyl benzoate may not be effective when applied according to the manufacturer's instructions, but may be effective when applied more frequently (i.e., three to four times a year) and for longer periods (up to 24 h) even with lower concentrations (0.4%). Essential oils were shown to have little acaricidal activity, but virtually no effect was observed with tea. Among the chemicals used, phenyl salicylate seems to be promising as an alternative acaricide.

Topics: Animals; Benzoates; Dose-Response Relationship, Drug; Insecticides; Mites; Oils, Volatile; Salicylates; Time Factors

The aromatic compounds phenyl benzoate (PB), phenyl salicylate (PS), and biphenyl (BP), which have previously been found to leach from poly(methyl methacrylate) denture base materials, were tested for cytotoxicity and biologic effects by L929 cells in culture. The octanol-water partition coefficient (log P(ow), a descriptor for the lipophilicity, was determined for the compounds. Cytotoxicity was evaluated by total cell growth and the plating efficiency test, and biologic effects by the total fatty acid composition of L929 cells. The commonly used tests, total cell growth and plating efficiency, did not show any significant changes of the cells due to the compounds. On the other hand, BP and PS, in particular, induced changes in the total fatty acid composition of L929 cells. The problem of bioavailability of aromatic compounds in cell culture assays and the relation to lipophilicity was addressed.

Topics: Animals; Biocompatible Materials; Biological Availability; Biphenyl Compounds; Cell Division; Cells, Cultured; Denture Bases; Fatty Acids; Fibroblasts; Lipids; Materials Testing; Methylmethacrylates; Mice; Salicylates

Unstimulated saliva was collected from orthodontic patients and subjected to combined gas-chromatography and gas-chromatography/mass-spectrometry analyses. Saliva was collected before insertion of removable orthodontic appliances made of cold-cured resins. Saliva was then collected 1-2 months after insertion of the appliances and 1 week after they had been removed. Phenyl benzoate (PB) and phenyl salicylate (PS) were identified in pooled saliva samples from patients wearing the appliances. Biphenyl and 2-methoxy-4-hydroxy-benzophenone in addition to PB and PS were identified in a study with in vitro specimens made of orthodontic resin. The leaching of compounds from these test specimens processed by a powdering technique and a pre-mix technique was compared.

Topics: Biphenyl Compounds; Child; Chromatography, Gas; Chromatography, High Pressure Liquid; Diffusion; Ethanol; Female; Gas Chromatography-Mass Spectrometry; Humans; Isotonic Solutions; Male; Microscopy, Electron, Scanning; Orthodontic Appliances; Resins, Synthetic; Ringer's Solution; Salicylates; Saliva; Surface Properties; Time Factors

Topics: Adolescent; Adult; Cross Reactions; Dermatitis, Allergic Contact; Eyeglasses; Female; Humans; Male; Resorcinols; Salicylates

Topics: Adolescent; Dermatitis, Contact; Dermatologic Agents; Female; Humans; Salicylates

We report 3 cases of allergic contact dermatitis behind the ears from wearing the same brand of industrial safety spectacles. In each case, a positive patch test was obtained with scrapings of the plastic frame. In 2 cases further patch tests with constituents of the plastic were carried out; positive patch tests were obtained with phenyl salicylate. Phenyl salicylate is used as an ultraviolet inhibitor in some cellulose acetate butyrate and cellulose acetate propionate formulae. It has previously been reported as a contact sensitizer from its use as a sun screen in a lip salve. Positive patch test reactions were also obtained variously in these patients with balsam of Peru, resorcinol monobenzoate, and epoxy resin.

Topics: Adult; Dermatitis, Contact; Dermatitis, Occupational; Eye Protective Devices; Humans; Male; Middle Aged; Protective Devices; Salicylates

Topics: Animals; Cheilitis; Chemical Phenomena; Chemistry; Dermatitis, Atopic; Dermatitis, Contact; Dermatologic Agents; Drug Hypersensitivity; Female; Guinea Pigs; Humans; Patch Tests; Salicylates

The in vitro carcinogenic activities of 3-(N-salicyloyl)amino-1,2,4-triazole (SAT) and its two components, 3-amino-1,2,4-triazole and phenyl salicylate were examined in a transformation assay with cryopreserved hamster embryo cells. SAT induced morphological transformation at certain doses between 10 microgram/ml and 100 microgram/ml in each of 5 repeated experiments, but gave a negative result in the Salmonella mutation assay. 3-Amino-1,2,4-triazole also induced transformation in 3 repeated experiments. Phenyl salicylate did not induce transformation at any of the doses tested in 3 consecutive experiments.

Topics: Amitrole; Animals; Carcinogens; Cell Transformation, Neoplastic; Cells, Cultured; Cricetinae; Embryo, Mammalian; Mutagens; Salicylates; Triazoles

Six cases of contact dermatitis from a lip salve are described. Five were allergic to phenyl salicylate and one to geraniol in the fragrance. The dermatitis spread in a ring around the mouth. Phenyl salicylate has been removed from the formulation.

Topics: Adult; Child; Dermatitis, Contact; Dermatologic Agents; Female; Humans; Lip; Male; Patch Tests; Salicylates

Topics: Adult; Cheilitis; Dermatitis, Contact; Dermatologic Agents; Female; Humans; Salicylates

Topics: Animals; Mice; Salicylates; Streptomycin; Suspensions; Tuberculosis

Topics: Chlorides; Ions; Pharmaceutical Preparations; Pilocarpine; Procaine; Salicylates; Thymol

Topics: Humans; Salicylates