Naphthol Research Articles

Synthesis of (2-hydroxy-5-nitrophenyl)di[1-(2-hydroxynaphthyl)]methane and 12-[1-(2-hydroxynaphthyl)]-10-nitro-12H-benzo[α]xanthene from of 5-nitrosalicylaldehyde derivatives and β-naphthol

The reaction of the morpholinal or anil of 5-nitrosalicylaldehyde with β-naphthol yielded (2-hydroxy-5-nitrophenyl)di[1-(2-hydroxynaphthyl)]methane. Condensation of the latter compound in boiling nitromethane gave 12-[1-(2-hydroxynaphthyl)]-10-nitro-12H-benzo[α]xanthene.

Facile Bisarylation of Aldehydes Using Titanium Naphtholates

The facile bisarylation of a range of aldehydes using the titanium naphtholate generated from naphthol 5 and diisopropoxytitanium (IV) chloride is reported.

Syntheses of Calix[4]naphthalenes Derived from 1-Naphthol

Syntheses of Calix[4]naphthalenes Derived from 1-Naphthol

Gas chromatographic-mass spectrometric analysis of polycyclic aromatic hydrocarbon metabolites in Antarctic fish (Notothenia gibberifrons) injected with Diesel Fuel Arctic

Fish (Notothenia gibberifrons) collected in pristine Antarctic sites were injected with Diesel Fuel Arctic (DFA). Gas chromatography/mass spectrometry (GC/MS) was used to identify and quantify polycyclic aromatic hydrocarbon (PAH) metabolites obtained from hydrolyzed fish bile. The concentrations of naphthols (NPH), phenanthrenols (PHN), dibenzothiophenols (DBT), and total PAH metabolites (∑PAH) vary with time. The response curve (production of PAH metabolites vs. time) resembled a Sigmoid curve, with an initial low response at 24 h followed by a rapid rise in production of PAH metabolites (55.74 μg/g) 120 h after exposure to DFA. PAH metabolites identified include NPH, PHN, and DBT and their alkylated derivatives, reflecting the composition of the DFA to which the fish were exposed. The GC/MS technique is highly sensitive, particularly in the detection of multi-ring PAH metabolites. The results suggest that analysis of PAH metabolites is a valuable tool for environmental monitoring and assessment of exposure to petroleum.

Longitudinal study of excretion of metabolites of polycyclic aromatic hydrocarbons in urine from two psoriatic patients.

Coal tar, which is widely used in the treatment of patients with atopic dermatitis, chronic eczema, and psoriasis, contains a large amount of polycyclic aromatic hydrocarbons (PAH). Some of the PAH compounds are known either to be carcinogenic or to potentiate the effects of other carcinogenic substances. In the present study, the excretion patterns of 1-hydroxypyrene (metabolite of pyrene) and alpha-naphthol (metabolite of naphthalene) in urine were studied in 2 patients, both treated once a day with coal tar pitch covering more than 50% of the skin. After 1 week of treatment, the concentration of both alpha-naphthol and 1-hydroxypyrene increased approximately 100 times. However, the concentration after 3 weeks of treatment was decreased to approximately the concentration measured before initiation of the treatment, even though the patients were coal tar-treated with unchanged intensity. The measured concentrations of alpha-naphthol and 1-hydroxypyrene in the urine of the 2 patients exceeded by order of magnitude the levels measured in the urine of occupationally exposed workers, and in view of the present study, epidemiological studies are needed to clarify to what extent coal tar treatment results in an increased risk of skin cancer, and e.g. bladder cancer.

Ultrastructure and cytochemical characteristics of leukocyte infected with Hepatozoon canis.

We have observed the ultrastructure of a canine leukocyte infected with Hepatozoon canis by transmission electron microscope. The infected leukocytes contained many small vesicles and a few typical granules in the cytoplasm. They also contained a few rough surfaced endoplasmic reticula, mitochondria and a segmented nucleus with condensed chromatin. Cytochemical analysis indicated that the infected leukocytes with H. canis contained little alkaline phosphatase, peroxidase, naphthol AS-D chloroacetate esterase or alpha naphthol acetate esterase. These results suggested that the infected leukocytes were neutrophils or monocytes which lost their typical characteristics.

Selection of a Pseudomonas cepacia strain constitutive for the degradation of trichloroethylene.

Tn5 insertion mutants of Pseudomonas cepacia G4 that were unable to degrade trichloroethylene (TCE), toluene, or phenol or to transform m-trifluoromethyl phenol (TFMP) to 7,7,7-trifluoro-2-hydroxy-6-oxo-2,4-heptadienoic acid (TFHA) were produced. Spontaneous reversion to growth on phenol or toluene as the sole source of carbon was observed in one mutant strain, G4 5223, at a frequency of approximately 1 x 10(-4) per generation. One such revertant, G4 5223-PR1, metabolized TFMP to TFHA and degraded TCE. Unlike wild-type G4, G4 5223-PR1 constitutively metabolized both TFMP and TCE without aromatic induction. G4 5223-PR1 also degraded cis-1,2-dichloroethylene, trans-1,2-dichloroethylene, and 1,1-dichloroethylene and oxidized naphthalene to alpha naphthol constitutively. G4 5223-PR1 exhibited a slight retardation in growth rate at TCE concentrations of > or = 530 microM, whereas G4 (which was unable to metabolize TCE under the same noninducing growth conditions) remained unaffected. The constitutive degradative phenotype of G4 5223-PR1 was completely stable through 100 generations of nonselective growth.

Studies with Polyfunctionally Substituted Heterocycles: Synthesis of New Pyridines, Naphtho[1,2-b]pyrans, Pyrazolo[3,4-b]pyridines and Pyrazolo[l,5-a]pyrimidines

A variety of new polyfunctionally substituted pyridines, naphthopyrans and pyrazolopyrimidines were prepared via reacting ylidenemalononitriles with thiophenol, thionaphthol, naphthols and or aminopyrazoles.

Influence of mixing on the azo-coupling of 1-naphthol and diazotized aniline

Influence of mixing on the azo-coupling of 1-naphthol and diazotized aniline

The intragranular location of carboxyl groups in neuromelanin and lipofuscin in human brain and in meningeal melanosomes in mouse brain.

The intragranular location of carboxyl groups was tinctorially determined in human substantia nigra neuromelanin granules, human inferior olive lipofuscin granules, and mouse meningeal melanosomes. Soluble and insoluble lipid was stained with beta naphthol Sudans in unoxidized and oxidized frozen and paraffin sections containing neuromelanin or lipofuscin. Nile blue demonstrated carboxyls in unoxidized neuromelanin, lipofuscin, and melanin, and in oxidized neuromelanin and lipofuscin. Carbodiimide demonstrated carboxyls in unoxidized and oxidized lipofuscin and oxidized neuromelanin. In all instances, staining for carboxyls was inhibited by prior mild methylation, and proof of their presence was obtained by a pre-staining, stepwise, alternating, and repetitive mild demethylation, mild methylation sequence. Structurally, carboxyls were demonstrated in the neuromelanin granule's soluble lipid-free lipofuscin component, in the meningeal melanosome's melanin component, and virtually throughout the lipofuscin granule. The following structural and chemical basis was proposed for the different resistance of Nile blue staining of melanosomes and of neuromelanin and lipofuscin to acetone extraction. Nile blue forms an insoluble complex with melanosomal dopa-melanin's quinonoid, diphenolic, and undissociated carboxyl units. Such complex formation does not occur in neuromelanin's carboxyl-free dopamine-melanin component, however. Instead, Nile blue ionogenicly bonds with dissociated carboxyls belonging to the neuromelanin granule's lipofuscin component.

Effect of n-Alkanols on the Solubilization of Sudan III and Sudan IV in Aqueous Ionic and Nonionic Micelles

Solubilization of aminoazobenzene-beta-naphthol (Sudan III) and orthotoluene-azo-orthotoluene-azo-beta naphthol (Sudan IV) dyes in anionic, cationic, and nonionic micelles in aqueous medium, have been studied spectrophotometrically at 30°C. The absorbance of either of the solubilized dye in dilute surfactant solutions does not change appreciably. But it was found to vary linearly with surfactant concentration above the CMC. Comparable solubilities of dyes in concentrated solutions of surfactants and in organic solvents provide some indication about the location of the solubilizate in the micelle interior. For a particular dye-surfactant system, moles of surfactant solubilizing a mole of dye, N D , have been calculated from the straight live portions of the plots. N D has been found to depend on the nature of the surfactant and the structure of dye. Decreased values of N D with increased chain length of added alkanols have been explained in the light of partitioning of alcohol at the micelle water interface. Lower values of standard free energy of solubilization indicate smaller hydrophobic contribution in the solubilization process. The mechanism of solubilization has been found to depend on the nature of solubilizer, solubilizate, and the additives.

MEASUREMENT OF THE DIFFUSIVITY OF 1-NAPHTHOL IN WATER WITH A ROTATING DISC

The solubility and diffusivity of 1-naphthol in water are reported at several temperatures.

XPS structure elucidation of polymer film coatings obtained by electropolymerizing naphthol derivatives

Preparation d'une serie d'electrodes modifiees electrochimiquement par polymerisation electrolytique d'une serie de derives du naphtol sur Pt, Au et graphite. Identification et elucidation du mecanisme de polymerisation et structure des films des poly(naphtol) et poly(naphtoquinone)

One-carrier thermally stimulated currents and space-charge-limited currents in naphthalene crystals: Doped and irradiated samples.

Measurements of space-charge-limited currents (SCLC) and thermally stimulated currents (TSC) were done in naphthalene single crystals grown from the melt and also from solution. Crystals grown from the melt were irradiated with x rays to a dose that ranged between 8×104 and 6×106 R. These crystals were also doped with beta naphthol with concentrations that varied from 10−4 to 10−2 in mole fraction. Melted crystals showed a trap level at 0.71 eV using SCLC and 0.79 eV using TSC, whereas solution crystals showed 0.43 eV using SCLC and 0.78 eV using TSC. Irradiated samples showed a trap level at 0.50 eV. In the case of doped samples the impurities originate a trap level at a depth of 0.53 eV that was possible to predict theoretically. Results showed that care must be exercised to obtain a valid comparison between the SCLC and TSC measurements and also that trapping of charge carriers is greatly influenced by the conditions under which the crystals were grown.

Further histochemical studies characterizing the lipofuscin component of human neuromelanin.

The residuum of bleached substantia nigra neuromelanin and the nonoxidized and oxidized intraneuronal masses of inferior olive lipofuscin gave sudanophilic staining reactions with oil red O, Sudan black B, and a Sudan III and IV combination stain. The pigments also exhibited oxidation basophilia, each having been stained by Gomori's paraldehyde fuchsin method after bleaching or oxidation with potassium permanganate and by the modified carbol fuchsin method of Barbeito-Lopez after bleaching or oxidation with hydrogen peroxide or potassium permanganate. Confirmation of the presence of lipid substances in bleached neuromelanin was obtained by repeatedly staining, decolorizing, and restaining the residuum of the pigment when utilizing the chemically nonreactive beta naphthol type Sudan combination stain, Sudan III and IV. Not only were tinctorial properties characteristic of lipofuscin clearly demonstrated in the bleached residuum of neuromelanin, but additionally, a partial separation was achieved between the relatively soluble beta naphthol type Sudan-staining lipid component and an insoluble component, possibly lipoprotein, staining with Sudan black B and both basic fuchsin dye-containing mixtures. Consideration was given to the idea that the oxidation basophilia of these neuronal pigments was due to the oxidative formation or exposure of one or more kinds of acidic groups consisting of carboxyls or those containing sulfur or phosphorus.

Atypical Surface Marker Characteristics in a T‐Cell Lymphoma

A case of T-cell lymphoma with an unusual phenotype is described. The majority of malignant tumour cells did not form E-rosettes, and lacked surface immunoglobulin but reacted with an antiserum to T cells and thymocytes. Localised acid phosphatase and non-specific alpha naphthol acid esterase activities and a prominent, convoluted, nuclear pattern in some neoplastic cells also supported the T cell derivation. The results demonstrate the importance of using a panel of markers for identification of the cellular derivation of some lymphomas.

Tissue culture studies in Hodgkin's disease: Morphologic, cytogenetic, cell surface, and enzymatic properties of cultures derived from splenic tumors.

Monolayer and suspension cell cultures prepared from Hodgkin's disease tumors in the spleen were examined microscopically and by cytogenetics, tested for lymphocyte and monocyte cell surface properties, and assayed for enzymes by histochemical and spectrophotometric techniques. Hodgkin's disease monolayer cultures were composed of rapidly proliferating round and polygonal cells that were capable of propagation in vitro for an indefinite period of time. Abnormal aneuploid chromosomes were found in short-term Hodgkin's disease monolayers that had been passaged 16-20 times, and in established cell lines carried in culture longer than 3 yr and passaged more than 200 times. Cells fromHodgkin's disease monolayers contained lysozyme (muramidase), fluoride-resistant alpha naphthol acetate esterase, acid and alkaline phosphatase, and chymotrypsin-like activity. The monolayers did not exhibit specific cell surface markers or phagocytosis. Suspension cultures derived from Hodgkin's disease monolayers were composed of cells with aneuploid karyotypes and similar enzymes. The Hodgkin's disease suspension culture cells had surface receptors for complement and IgGFc, lacked surface or cytoplasmic immunoglobulin, and did not form Erosettes, react with an antithymocyte serum, nor exhibit phagocytosis. Normal monolayer culture cells, derived from adult spleen and human fetal spleen and thymus, were composed of spindle cells with a diploid number of chromosomes that could be carried for only a finite period of time in vitro. Normal cultured cells contained similar esterases and phosphatases, but were devoid of lysozyme and chymotrypsin-like activity. The morphologic, cytogenetic, cell surface, and enzymatic findings indicate that our Hodgkin's disease monolayer and suspension cultures are composed of cells with many properties suggesting an origin from monocytes (macrophages) rather than lymphocytes or fibroblasts. The presence of aneuploid karyotypes is consistent with a neoplastic origin and derivation from a malignant cell of Hodgkin's disease.

Alkylation of 2-naphthol by alcohols in the presence of base

Alkylation of 2-naphthol by alcohols in the presence of base

Dimethylaminomethylation of phenols and α-naphthols

Dimethylaminomethylation of phenols and α-naphthols

Mechanism of the quenching of the fluorescence of 2-naphthol by pyridine

Mechanism of the quenching of the fluorescence of 2-naphthol by pyridine