Sigma-Aldrich

Resorcinol ACS reagent, ≥99.0%; CAS Number: 108-46-3; EC Number: 203-585-2; Synonyms: 1,3-Benzenediol; Linear Formula: C6H4-1,3-(OH)2; find Sigma-Aldrich-398047 MSDS, related peer-reviewed papers, technical documents, similar products & more at Sigma-Aldrich

Resorcinol ACS reagent, = 99.0 108-46-3

Resorcinol

Magnetic yolk-shell mesoporous silica microspheres with supported Au nanoparticles as recyclable high-performance nanocatalysts.

Size control and characterization of spherical carbon aerogel particles from resorcinol-formaldehyde resin.

Mesomorphic properties of resorcinol.

Preparation of biocompatible and antibacterial carbon quantum dots derived from resorcinol and formaldehyde spheres.

The chemistry of resorcinol carboxylation and its possible application to the CO<SUB>2</SUB> removal from exhaust gases.

Hair coloring products are one of the most important cosmetics for modern people; there are three major types of hair dyes, including the temporary, semi-permanent and permanent hair dyes. The selected hair dyes (such as ammonium persulfate, sodium persulfate, resorcinol and lawsone) are the important components for hair coloring products. Therefore, we analyzed the effects of these compounds on melanogenesis in B16-F10 melanoma cells. The results proved that hair dyes resorcinol and lawsone can reduce the production of melanin. The results also confirmed that resorcinol and lawsone inhibit mushroom and cellular tyrosinase activities in vitro. Resorcinol and lawsone can also downregulate the protein levels of tyrosinase and microphthalmia-associated transcription factor (MITF) in B16-F10 cells. Thus, we suggest that frequent use of hair dyes may have the risk of reducing natural melanin production in hair follicles. Moreover, resorcinol and lawsone may also be used as hypopigmenting agents to food, agricultural and cosmetic industry in the future.

Hair dyes resorcinol and lawsone reduce production of melanin in melanoma cells by tyrosinase activity inhibition and decreasing tyrosinase and microphthalmia-associated transcription factor (MITF) expression.

Graphitized carbons with mesoporous and macroporous structures were synthesized by a facile template-catalysis procedure using resorcinol and formaldehyde as carbon precursors and particulate hydrated metal oxides as both template and catalyst precursors. The materials were used as novel adsorbents for low-concentration benzene vapor. Furthermore, on the basis of the good electrical conductivities associated with the graphitized structures, an electrothermal desorption technique, which involved passing electric currents through the adsorbents to generate Joule heat, was employed to regenerate the saturated adsorbents and produce enriched benzene vapors. In comparison to microporous activated carbon, the porous graphitized carbons could afford a much quicker and more efficient regeneration by electrothermal desorption technique due to their enhanced conductivity and larger pore sizes. In addition, the concentration of the desorbed organics could be controlled by adjusting the applied voltages, which might be interesting for practical secondary treatment. It is promising that the joint utilization of porous graphitized carbon adsorbents and electrothermal desorption technique might develop effective and energy-saving processes for VOCs removal.

Porous graphitized carbon for adsorptive removal of benzene and the electrothermal regeneration.

With the availability of the local lymph node assay, and the ability to evaluate effectively the relative skin sensitizing potency of contact allergens, a model for quantitative-risk-assessment (QRA) has been developed. This QRA process comprises: (a) determination of a no-expected-sensitisation-induction-level (NESIL), (b) incorporation of sensitization-assessment-factors (SAFs) reflecting variations between subjects, product use patterns and matrices, and (c) estimation of consumer-exposure-level (CEL). Based on these elements an acceptable-exposure-level (AEL) can be calculated by dividing the NESIL of the product by individual SAFs. Finally, the AEL is compared with the CEL to judge about risks to human health. We propose a simplified approach to risk assessment of hair dye ingredients by making use of precise experimental product exposure data. This data set provides firmly established dose/unit area concentrations under relevant consumer use conditions referred to as the measured-exposure-level (MEL). For that reason a direct comparison is possible between the NESIL with the MEL as a proof-of-concept quantification of the risk of skin sensitization. This is illustrated here by reference to two specific hair dye ingredients p-phenylenediamine and resorcinol. Comparison of these robust and toxicologically relevant values is therefore considered an improvement versus a hazard-based classification of hair dye ingredients.

Quantitative risk assessment for skin sensitisation: consideration of a simplified approach for hair dye ingredients.

Alkylresorcinols are phenolic lipids, with homologues ranging from C17 to C25, found in high concentrations in whole grain wheat and rye, lower concentrations in barley, and negligible concentrations in refined wheat flour. The analysis of alkylresorcinols is of importance due to their potential as biomarkers of whole grain intake and emerging evidence for some biological effects. Present HPLC methods have insufficient resolution for accurately quantitating the mix of alkyl- and alkenylresorcinols found in rye. An ultrahigh-pressure liquid chromatography method was developed, and three detection methods (CoulArray (CAED), ultraviolet (UV), and fluorescence detection (FD)) were compared for cereal alkylresorcinol analysis. The lower limits of quantitation and detection were 50 and 20 pg injected, 5 pg and 2 pg injected, and 500 and 1250 pg injected for FD, CAED, and UV, respectively. FD and CAED provided similar results, with some bias for higher results with FD (<10% difference). UV detection generally resulted in overestimation of alkylresorcinol concentrations. The method was applied to cereal (15) and cereal product (90) samples mainly from the United States with results in the same range as previous methods. The improved resolution with this method allows facile analysis of alkylresorcinols from cereal products, including minor unsaturated homologues such as those found in rye.

Analysis of alkylresorcinols in cereal grains and products using ultrahigh-pressure liquid chromatography with fluorescence, ultraviolet, and CoulArray electrochemical detection.

Mycothiol (MSH) plays important roles in maintaining cytosolic redox homeostasis and in adapting to reactive oxygen species in the high-(G + C)-content Gram-positive Actinobacteria. However, its physiological roles are ill defined compared to glutathione, the functional analog of MSH in Gram-negative bacteria and most eukaryotes. In this research, we explored the impact of intracellular MSH on cellular physiology by using MSH-deficient mutants in the model organism Corynebacterium glutamicum. We found that intracellular MSH contributes significantly to resistance to alkylating agents, glyphosate, ethanol, antibiotics, heavy metals and aromatic compounds. In addition, intracellular MSH is beneficial for withstanding oxidative stress induced by various oxidants in C. glutamicum. This study greatly expanded our current knowledge on the physiological functions of mycothiol in C. glutamicum and could be applied to improve the robustness of this scientifically and commercially important species in the future.

Physiological roles of mycothiol in detoxification and tolerance to multiple poisonous chemicals in Corynebacterium glutamicum.

An overview on the preparation and properties of resorcinol-formaldehyde (RF) organic and carbon gels reveals the fascinating and remarkably flexible properties of RF carbon and organic gels and how these properties are related to the synthesis and processing conditions. The structural properties can be easily tailored by rigidly controlling such conditions. However, slight variations in some conditions may cause drastic variations in the structural characteristics, and hence properties. Therefore, the effects of different conditions must be well-understood before attempting to tailor organic or carbon gels to specific applications. The most important factors that affect the properties of an organic gel are the precursor concentrations, the catalyst type and concentration, the time and temperature of curing, and the drying method. In addition to these factors, characteristics of activated carbon gels also depend on the pyrolysis temperature and the activation method. These conditions impact the structural and performance characteristics significantly.

Advances in tailoring resorcinol-formaldehyde organic and carbon gels.

Inhibition of 12 mammalian isoforms of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1), CA I-XIV, with a series of phenols was investigated. The inhibition profile by phenols of these CAs was distinct from those of the sulfonamides and their isosteres, the main class of clinically used inhibitors. Phenol and some of its 2-, 3- and 4-substituted derivatives incorporating hydroxy-, fluoro-, carboxy-, amino-, cyano- and acetamido-moieties were generally effective low micromolar CA inhibitors, with inhibition constants in the range of 9.8-4003 microM against CA I, of 0.090-870 microM against CA II, of 0.71-885 microM against CA III, of 9.5-809 microM against CA IV, of 8.7-867 microM against CA VA, of 4.2-649 microM against CA VB, of 11.4-658 microM against CA VI, of 9.1-1359 microM against CA VII, of 8.8-517 microM against CA IX, of 4.1-598 microM against CA XII, of 12.2-697 microM against CA XIII and of 10.1-49.8 microM against CA XIV, respectively. The different mechanisms of inhibition by phenols as compared to sulfonamides, and their diverse inhibition profile for these mammalian isozymes, makes this class of derivatives of great interest for the design of compounds with selectivity and/or specificity for some of the medicinal chemistry targets belonging to this enzyme family.

Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid.

Upon pathogen attack, fruit trees such as apple (Malus spp.) and pear (Pyrus spp.) accumulate biphenyl and dibenzofuran phytoalexins, with aucuparin as a major biphenyl compound. 4-Hydroxylation of the biphenyl scaffold, formed by biphenyl synthase (BIS), is catalyzed by a cytochrome P450 (CYP). The biphenyl 4-hydroxylase (B4H) coding sequence of rowan (Sorbus aucuparia) was isolated and functionally expressed in yeast (Saccharomyces cerevisiae). SaB4H was named CYP736A107. No catalytic function of CYP736 was known previously. SaB4H exhibited absolute specificity for 3-hydroxy-5-methoxybiphenyl. In rowan cell cultures treated with elicitor from the scab fungus, transient increases in the SaB4H, SaBIS, and phenylalanine ammonia lyase transcript levels preceded phytoalexin accumulation. Transient expression of a carboxyl-terminal reporter gene construct directed SaB4H to the endoplasmic reticulum. A construct lacking the amino-terminal leader and transmembrane domain caused cytoplasmic localization. Functional B4H coding sequences were also isolated from two apple (Malus × domestica) cultivars. The MdB4Hs were named CYP736A163. When stems of cv Golden Delicious were infected with the fire blight bacterium, highest MdB4H transcript levels were observed in the transition zone. In a phylogenetic tree, the three B4Hs were closest to coniferaldehyde 5-hydroxylases involved in lignin biosynthesis, suggesting a common ancestor. Coniferaldehyde and related compounds were not converted by SaB4H.

Biphenyl 4-Hydroxylases Involved in Aucuparin Biosynthesis in Rowan and Apple Are Cytochrome P450 736A Proteins.

Inhibition of the newest isoform of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1), CA XV, with a series of phenols was investigated. Murine CA XV showed an inhibition profile by phenols distinct of those of the cytosolic human isoforms CA I and II. Phenol and some of its 2-, 3-, and 4-substituted derivatives incorporating hydroxy, fluoro, carboxy, and acetamido moieties were effective CA XV inhibitors, with inhibition constants in the range of 7.20-11.30 microM, whereas compounds incorporating 4-amino-, 4-cyano, or 3-hydroxy groups were less effective (K(I)s of 335-434 microM). The best phenol inhibitor was clioquinol (K(I) of 2.33 microM). Phenols show a different inhibition mechanism as compared to sulfonamides and their isosteres, and may lead to the design of compounds with selectivity for inhibiting different CA isozymes with medicinal chemistry applications.

Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols.

The development of in silico and in vitro tools to estimate or predict the passive human skin permeation and distribution of new chemical entities, useful in dermal drug delivery, in absorption studies of toxic compounds, and in the cosmetics industry, is presented. In vitro permeation parameters were measured using the artificial membrane PAMPA-skin. The Volsurf approach was then applied to extract pertinent descriptors from molecular interaction fields characterizing the molecular structure of tested compounds. Two useful three-dimensional solvatochromic models able to predict PAMPA permeation parameters directly from the molecular structure were obtained using the partial least squares analysis. The models also provide valuable information to understand the link between physicochemical and structural properties of tested compounds and their interactions with the artificial membrane PAMPA-skin and can be useful to rapidly estimate their permeation through the human skin.

In silico and in vitro filters for the fast estimation of skin permeation and distribution of new chemical entities.

Accumulating evidence suggest that diets rich in cocoa flavanols may have beneficial effects on cardiovascular health. The major cocoa flavanol monomer, (-)-epicatechin (EC), is readily absorbed and circulates primarily as glucuronidated, sulfated, and O-methylated metabolites in human plasma. However, cellular metabolism, for example in endothelial cells, is less well defined. In the present study we detail the uptake and cellular metabolism of EC and its major in vivo metabolites, (-)-epicatechin-3'-β-D-glucuronide (E3G), (-)-epicatechin-3'-sulfate (E3S), 3'-O-methyl-(-)-epicatechin-5-sulfate (3ME5S), and 3'-O-methyl-(-)-epicatechin-7-sulfate (3ME7S) in human endothelial (HUVEC), liver (HepG2) and intestinal epithelial cells (Caco-2 monolayer). Our results indicate that EC associates with HUVECs, leading to its intracellular metabolism to 3ME7G and 3ME7S. In contrast, none of the metabolites were taken up by the cells. The metabolic rate and pattern of metabolism in HUVECs was similar to that observed in HepG2 cells, whilst in Caco-2 cells EC was metabolized to E3G, 3ME5G, 3ME7G, 4ME5G, 4ME7G and 3ME7S. Our data support the notion that endothelial cells may contribute significantly to EC metabolism. However, major human circulating metabolites are not accounted for in these model systems underscoring that caution should be taken when drawing conclusions on in vivo flavanol metabolism from in vitro experiments.

Uptake and metabolism of (-)-epicatechin in endothelial cells.

This work was devoted to the search for new artificial membranes allowing a rapid evaluation of passive human skin permeation of compounds with a parallel artificial membrane permeability assay (PAMPA). Effective permeability coefficients (Pe) determined for a set of compounds using the PAMPA technique with isopropyl myristate (IPM) and silicone oil, alone or in mixture, were compared to the corresponding human skin permeability coefficient values (Kp). A good correlation between Pe and Kp was found for compounds tested through a membrane consisting of 70% silicone and 30% IPM. Moreover, positive correlation between the membrane retention of compounds and stratum corneum/water partition coefficients (PSC) was established. These results showed that this new artificial membrane, defined as PAMPA-skin, is able to mimic the main barrier properties of human stratum corneum and can be used for the fast prediction of passive human skin permeability coefficients.

Parallel artificial membrane permeability assay: a new membrane for the fast prediction of passive human skin permeability.

A set of 116 structurally very diverse compounds, mainly drugs, was characterized by 1630 molecular descriptors. The biological property modelled in this study was the transdermal permeability coefficient logK(p). The main objective was to find a limited set of suitable model compounds for skin penetration studies. The classification and regression trees (CART) approach was applied and the resulting groups were discussed in terms of their role as possible model compounds and their determining descriptors. A second objective was to model transdermal penetration as a function of selected descriptors in quantitative structure-property relationships (QSPR) using a boosted CART (BRT) approach and multiple linear regression (MLR) analysis, where regression models were obtained by stepwise selection of the best descriptors. Evaluation of the standard statistical, as well as descriptor-number dependent, regression quality attributes yielded a maximal 10-dimensional MLR model. The CART and MLR models were subjected to an external validation with a test set of 12 compounds, not included in the original learning set of 104 compounds, to assess the predictive power of the models.

Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds.

Superficially porous particles (SPP), or core shell particles, which consist of a non-porous silica core surrounded by a thin shell of porous silica, have gained popularity as a solid support for chromatography over the last decade. In the present study, five unbonded silica, one diol, and two ethylpyridine (2-ethyl and 4-ethyl) SPP columns were evaluated under SFC conditions using two mixtures, one with 17 drug-like compounds and the other one with 7 drug-like basic compounds. Three of the SPP phases, SunShell™ 2-ethylpyridine (2-EP), Poroshell™ HILIC, and Ascentis(®) Express HILIC, exhibited superior performances relative to the others (reduced theoretical plate height (hmin) values of 1.9-2.5 for neutral compounds). When accounting for both achievable plate count and permeability of the support using kinetic plot evaluation, the Cortecs™ HILIC 1.6μm and Ascentis(®) Express HILIC 2.7μm phases were found to be the best choices among tested SPPs to reach efficiencies up to 30,000 plates in the minimum amount of time. For desired efficiencies ranging from 30,000 to 60,000 plates, the SunShell™ 2-EP 2.6μm column clearly outperformed all other SPPs. With the addition of a mobile phase additive such as 10mM ammonium formate, which was required to elute the basic components with sharp peaks, the Poroshell™ HILIC, SunShell™ Diol and SunShell™ 2-EP phases represent the most orthogonal SPP columns with the highest peak capacities. This study demonstrates the obvious benefits of using columns packed with SPP on current SFC instrumentation.

Evaluation of stationary phases packed with superficially porous particles for the analysis of pharmaceutical compounds using supercritical fluid chromatography.

Resorcinol

ACS reagent, ≥99.0%

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