Distribution by Scientific Domains
Distribution within Chemistry

Kinds of Salicylate

  • benzyl salicylate
  • methyl salicylate
  • phenyl salicylate
  • sodium salicylate

  • Terms modified by Salicylate

  • salicylate concentration

  • Selected Abstracts

    Fine-Tuning Plant Defence Signalling: Salicylate versus Jasmonate

    PLANT BIOLOGY, Issue 1 2006
    G. J. M. Beckers
    Abstract: Plant defences against pathogens and herbivorous insects form a comprehensive network of interacting signal transduction pathways. The signalling molecules salicylic acid (SA) and jasmonic acid (JA) play important roles in this network. SA is involved in signalling processes providing systemic acquired resistance (SAR), protecting the plant from further infection after an initial pathogen attack. SAR is long-lasting and provides broad spectrum resistance to biotrophic pathogens that feed on a living host cell. The regulatory protein NPR1 is a central positive regulator of SAR. SA-activated NPR1 localizes to the nucleus where it interacts with TGA transcription factors to induce the expression of a large set of pathogenesis-related proteins that contribute to the enhanced state of resistance. In a distinct signalling process, JA protects the plant from insect infestation and necrotrophic pathogens that kill the host cell before feeding. JA activates the regulatory protein COI1 that is part of the E3 ubiquitin ligase-containing complex SCFCOI1, which is thought to derepress JA-responsive genes involved in plant defence. Both synergistic and antagonistic interactions have been observed between SA- and JA-dependent defences. NPR1 has emerged as a critical modulator of cross-talk between the SA and JA signal and is thought to aid in fine tuning defence responses specific to the encountered attacker. Here we review SA- and JA-dependent signal transduction and summarize our current understanding of the molecular mechanisms of cross-talk between these defences. [source]

    Should Aspirin be Used to Counteract ,Salicylate Deficiency'?

    Gareth Morgan
    Emerging evidence suggests that aspirin reduces the risk of other chronic diseases such as certain forms of cancer. Salicylate may contribute to the disease reduction effects. It is present naturally in fruits and vegetables and individuals with a low intake of these foods may be ,salicylate deficient'. This deleterious state may constitute a significant public health threat. Interventions to prevent deficiency, such as low-dose aspirin programmes, could have substantial beneficial health impacts around the world. [source]

    One-Dimensional Network Constructed by Salicylate and Phenanthroline Ligands with Copper (II)

    Lag-Guan Zhu
    Abstract A novel complex, [Cu2 (phen) (sal) (Hsal)2]n (1), was synthesized and structurally characterized. The base dimeric units are hold by sal ligands and extended into 1-D network. The carboxylate groups of salicylates coordinate to the central ion in three different coordination modes: chelating, bridging and bridging-chelating. In the case of bridging-chelating of the carboxylate group of the salicylate, all three oxygen atoms of salicylate are bidentately coordinated to copper ion, namely, ,4 -,3 binding mode. [source]

    Effect of ion-exchange fiber structure on the binding and release of model salicylates

    Kaisa R. Hänninen
    Abstract Salicylates were used as model anions to evaluate the effect of the structure (framework and ion-exchange groups) of fibrous anion-exchangers on the extent and mechanism(s) of compound binding and release. Binding was affected by the physicochemical properties of both the salicylates and the ion-exchange fibers. The highest molar amount of binding was obtained with the most lipophilic salicylate (5-chlorosalicylic acid) and the weak base (vinylpyridine) anion-exchange fibers. However, when the ion-exchange capacity was taken into account, higher binding was obtained in fibers of poly(ethylene) framework compared to the viscose-based fibers. The extent of salicylate release into NaCl solution(s) was dependent on the physicochemical characteristics of both the fiber and the bound model salicylate as well as on the amount of extracting ions. With strong base fibers (trimethylammonium), the viscose framework released the salicylates more efficiently than the poly(ethylene) framework. In the case of weak base fibers, the poly(ethylene) framework released the salicylates to a higher extent than the viscose framework. Calculated equilibrium constants (K) of the ion-exchange reactions illustrated that in addition to electrostatic interactions (pure ion-exchange mechanism), non-electrostatic interactions (hydrophobic interactions and/or hydrogen bonding) were also involved. However, the release of the salicylates was efficiently modified by the amount of extracting electrolyte, demonstrating that ion-exchange was the prevalent release mechanism. © 2005 Wiley-Liss, Inc. and the American Pharmacists Association J Pharm Sci 94:1772,1781, 2005 [source]

    ChemInform Abstract: Rhodium-Catalyzed Aryl- and Alkylation,Oligomerization of Alkynoates with Organoboron Reagents Giving Salicylates.

    CHEMINFORM, Issue 30 2010
    Yuichi Yasuhara
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

    ChemInform Abstract: Synthesis of Functionalized Salicylates by Formal [3 + 3] Cyclocondensation of 1,3-Bis(silyloxy)buta-1,3-dienes with 3-Alkoxy-2-en-1-ones.

    CHEMINFORM, Issue 50 2009
    Gerson Mross
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

    One-Pot Synthesis of Xanthones and Thioxanthones by the Tandem Coupling,Cyclization of Arynes and Salicylates.

    CHEMINFORM, Issue 2 2006
    Jian Zhao
    No abstract is available for this article. [source]

    Sensitization to 26 fragrances to be labelled according to current European regulation

    CONTACT DERMATITIS, Issue 1 2007
    Results of the IVDK, review of the literature
    To study the frequency of sensitization to 26 fragrances to be labelled according to current European regulation. During 4 periods of 6 months, from 1 January 2003 to 31 December 2004, 26 fragrances were patch tested additionally to the standard series in a total of 21 325 patients; the number of patients tested with each of the fragrances ranged from 1658 to 4238. Hydroxymethylpentylcyclohexene carboxaldehyde (HMPCC) was tested throughout all periods. The following frequencies of sensitization (rates in %, standardized for sex and age) were observed: tree moss (2.4%), HMPCC (2.3), oak moss (2.0), hydroxycitronellal (1.3), isoeugenol (1.1), cinnamic aldehyde (1.0), farnesol (0.9), cinnamic alcohol (0.6), citral (0.6), citronellol (0.5), geraniol (0.4), eugenol (0.4), coumarin (0.4), lilial (0.3), amyl-cinnamic alcohol (0.3), benzyl cinnamate (0.3), benzyl alcohol (0.3), linalool (0.2), methylheptin carbonate (0.2), amyl-cinnamic aldehyde (0.1), hexyl-cinnamic aldehyde (0.1), limonene (0.1), benzyl salicylate (0.1), ,-methylionon (0.1), benzyl benzoate (0.0), anisyl alcohol (0.0). 1) Substances with higher sensitization frequencies were characterized by a considerable number of ,++/+++' reactions. 2) Substances with low sensitization frequencies were characterized by a high number of doubtful/irritant and a low number of stronger (++/+++) reactions. 3) There are obviously fragrances among the 26 which are, with regard to contact allergy, of great, others of minor, and some of no importance at all. [source]

    An ecological cost of plant defence: attractiveness of bitter cucumber plants to natural enemies of herbivores

    ECOLOGY LETTERS, Issue 3 2002
    Anurag A. Agrawal
    Abstract Plants produce defences that act directly on herbivores and indirectly via the attraction of natural enemies of herbivores. We examined the pleiotropic effects of direct chemical defence production on indirect defence employing near-isogenic varieties of cucumber plants (Cucumis sativus) that differ qualitatively in the production of terpenoid cucurbitacins, the most bitter compounds known. In release,recapture experiments conducted in greenhouse common gardens, blind predatory mites were attracted to plants infested by herbivorous mites. Infested sweet plants (lacking cucurbitacins), however, attracted 37% more predatory mites than infested bitter plants (that produce constitutive and inducible cucurbitacins). Analysis of the headspace of plants revealed that production of cucurbitacins was genetically correlated with large increases in the qualitative and quantitative spectrum of volatile compounds produced by plants, including induced production of (E,)-,-ocimene (3E,)-4,8-dimethyl-1,3,7-nonatriene, (E,E)-,-farnesene, and methyl salicylate, all known to be attractants of predators. Nevertheless, plants that produced cucurbitacins were less attractive to predatory mites than plants that lacked cucurbitacins and predators were also half as fecund on these bitter plants. Thus, we provide novel evidence for an ecological trade-off between direct and indirect plant defence. This cost of defence is mediated by the effects of cucurbitacins on predator fecundity and potentially by the production of volatile compounds that may be repellent to predators. [source]

    A 4-trifluoromethyl derivative of salicylate, triflusal, stimulates nitric oxide production by human neutrophils: role in platelet function

    De Miguel
    Background The thrombotic process is a multicellular phenomenon in which not only platelets but also neutrophils are involved. Recent in vitro studies performed in our laboratory have demonstrated that triflusal, a 4-trifluoromethyl derivative of salicylate, reduced platelet aggregation not only by inhibiting thromboxane A2 production but also by stimulating nitric oxide (NO) generation by neutrophils. The aim of the present study was to evaluate whether oral treatment of healthy volunteers with triflusal could modify the ability of their neutrophils to produce NO and to test the role of the NO released by neutrophils in the modulation of ADP-induced platelet aggregation and ,-granule secretion. Methods The study was performed in 12 healthy volunteers who were orally treated with triflusal (600 mg day,1) for 5 days. Flow cytometric detection of platelet surface expression of P-selectin was used as a measure of the ability of platelets to release the contents of their ,-granules. Results After treatment with triflusal, there was an increase in NO production by neutrophils and an increase in endothelial nitric oxide synthase (eNOS) protein expression in neutrophils. A potentiation of the inhibition of platelet aggregation by neutrophils was reversed by incubating neutrophils with both an l -arginine antagonist, NG -nitro- l -arginine methyl ester ( l -NAME) and an NO scavenger, 2-(4-carboxyphenyl)-4,4,5,5 tetramethylimidazoline 1-oxyl 3-oxide (C-PTIO). A slight decrease in P-selectin surface expression on platelets was found which was not modified by the presence of neutrophils and therefore by the neutrophil-derived NO. Exogenous NO released by sodium nitroprusside dose-dependently inhibited both ADP-stimulated ,-granule secretion and platelet aggregation. Therefore, platelet aggregation showed a greater sensitivity to be inhibited by exogenous NO than P-selectin expression. Conclusion Oral treatment of healthy volunteers with triflusal stimulated NO production and eNOS protein expression in their neutrophils. After triflusal treatment, the neutrophils demonstrated a higher ability to prevent ADP-induced platelet aggregation. However, the neutrophils and the endogenous NO generated by them failed to modify P-selectin expression in ADP-activated platelets. [source]

    Tripyrrinatocadmium Complexes: Enforcing Supramolecular Aggregation by a Large Ion

    Martin Bröring
    Abstract A newly developed method for the preparation of free base tripyrrin ligands HTrpy by cyanide-promoted demetalation of nickel chelates TrpyNiNCO was used in order to explore the chemistry of cadmium tripyrrins TrpyCdX with a variety of anionic co-ligands X. The introduction of the large CdII ion into the tripyrrin N3 coordination site was accomplished by the use of cadmium acetate as the metal precursor. Ligand exchange experiments using sodium salts of different anions disclose a marked tendency for pentacoordination, which is achieved either by the formation of chelates or of 1D coordination polymers that form as a consequence of the size of the central metal. The attempted introduction of chlorido, iodido, or cyanato ligands thus leads mainly to decomposed material, while the use of 1,1,1-trifluoracetylacetonate, salicylate, and acetate ligands results in stable, pentacoordinate and monomeric complexes with the external ligand bound as a four- or six-membered O,O -chelate ring. With the pseudohalogenido ligands thiocyanate, selenocyanate, and azide as well as with the weakly coordinating trifluoroacetate 1D coordination polymers with a variety of chain structures were obtained and investigated by X-ray diffraction studies. Interestingly TrpyCdN3 is present in the crystal as a coordinatively and hydrogen-bonded methanol adduct with a dimeric repeating subunit. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007) [source]

    The effect of topically applied salicylic compounds on serotonin-induced scratching behaviour in hairless rats

    J. S. Thomsen
    Abstract: There is a strong need for antipruritic substances for treating itch in clinical dermatology. In one recent human study, topically applied acetylsalicylic acid has been described to rapidly decrease histamine-induced itch. We have established a model for periferally elicited pruritus by injecting serotonin into the rostral back area (neck) in rats. Using this model, we aimed to investigate the antipruritic potential of four different salicylic compounds, which all possess different skin penetration characteristics. Eighteen rats were studied for 6 weeks. Prior to serotonin injections (2 mg/ml, 50 µl), 10 µl of test substances was applied to a circular area 18 mm in diameter. The four substances were salicylic acid, butyl salicylate, diethylamine salicylate and salicylamide, all solubilized in dimethyl isosorbide to a concentration of 5% w/w. Diethylamine salicylate and salicylamide were previously shown to be slowly absorbed through rat skin in contrast to salicylic acid and butyl salicylate. After serotonin injections, scratching was monitored by video recording for 1.5 h. Compared with the vehicle, a lower number of scratch sequences were seen when diethylamine salicylate (P < 0.001) and salicylamide (P = 0.005) had been applied. The numbers of scratch sequences were lower with diethylamine salicylate and salicylamide than with the vehicle throughout the 1.5-h study period. We conclude that topical application of diethylamine salicylate and salicylamide could suppress serotonin-induced scratching in rats. The antipruritic effect seems to be related to the slow drug release of the two substances. The results may be clinically relevant as serotonin induces itch in humans. [source]

    Pittosporum undulatum Vent. grown in Portugal: secretory structures, seasonal variation and enantiomeric composition of its essential oil

    Nicolau J. Ferreira
    Abstract Aerial parts of Pittosporum undulatum were collected fortnightly for 1 year at the Parque de Saúde de Lisboa. Collective samples of two populations were investigated, i.e. from pruned and non-pruned trees, and in addition samples from one pruned and one non-pruned individual. An SEM study of the aerial parts showed the presence of non-glandular T-shaped trichomes, and capitate trichomes with an elongated stalk and two to four round-shaped cells on the top. Numerous canals were seen at the level of the capsule wall as well as in the leaves and stems. Essential oil samples were isolated from the (deep-frozen) aerial parts by hydrodistillation to estimate the oil yields, and by distillation,extraction to determine their percentage composition, and analysed by GC and GC,MS. Monoterpenes (59,97%) were dominant in all oils, sabinene (5,58%), limonene (2,37%) and terpinen-4-ol (4,27%) being the major components, although in different relative amounts during the year of collection. Benzyl benzoate (8%) and benzyl salicylate (10%) attained high relative amounts in the oils from fully developed flowers, whereas in the oils from the other plant parts their relative amounts did not exceed 1%. The enantiomeric ratio of sabinene, limonene and terpinen-4-ol was investigated in the leaf, flower and capsule oils, showing dominance of the (+)-forms and homogeneity between all the oil samples. Copyright © 2006 John Wiley & Sons, Ltd. [source]

    A comparative study of the essential oils of the genus Plumeria Linn. from Malaysia

    Norsita Tohar
    Abstract The chemical composition of the flower oils of three Malaysian Plumeria Linn. species, P. acuminata Ait. (white flower), P. rubra Linn. (reddish-orange flower) and P. rubra Linn. (red flower), were determined by gas chromatography on two columns of different polarity, GC,MS and Kováts retention indices. The oil of P. acuminata Ait. (white flower) was made up predominantly of benzyl salicylate (39.0%), benzyl benzoate (17.2%), trans -nerolidol (10.6%), neryl phenylacetate (10.5%) and linalool (8.9%). Phenylethyl benzoate at 12.3% was the most abundant compound in the oil of P. rubra Linn. (reddish-orange flower), followed by dodecanoic acid at 11.8% concentration. Hexadecanoic acid constituted 9.3% and 27.2% of the oils of P. rubra Linn. (reddish-orange flower) and P. rubra Linn. (red flower), respectively. Copyright © 2006 John Wiley & Sons, Ltd. [source]

    Analysis of the essential oil of the aerial parts of Viola etrusca from Monte Labbro (South Tuscany, Italy) and in vivo analysis of flower volatiles using SPME

    Guido Flamini
    Abstract The composition of the essential oil of the endemic Viola etrusca Erben from Monte Labbro (Italy) has been studied for the first time. It was made up almost exclusively of methyl salicylate (96%), together with many other mono- and sesquiterpenes and non-terpenic alcohols and aldehydes. In addition, the SPME technique has been used to evaluate the volatiles emitted in vivo by different-coloured flowers. Copyright © 2002 John Wiley & Sons, Ltd. [source]

    The dual function of hepatic SOCS3 in insulin resistance in vivo

    GENES TO CELLS, Issue 2 2007
    Takehiro Torisu
    Inflammation associates with insulin resistance, which dysregulates nutrient homeostasis and leads to diabetes. The suppressor of cytokine signaling 3 (SOCS3), which is induced by pro-inflammatory cytokines, such as TNF, and IL-6, has been implicated in inflammation-mediated insulin resistance in the liver and adipocytes. However, no genetic evidence has been provided for the involvement of SOCS3 on insulin resistance. Here, we generated hepatocyte-specific SOCS3-deficient (L-SOCS3 cKO) mice and examined insulin sensitivity. Being consistent with a previous idea, the loss of SOCS3 in the liver apparently improved insulin sensitivity. However, unexpectedly, L-SOCS3 cKO mice exhibited obesity and systemic insulin resistance with age. Insulin signaling was rather suppressed in muscles, suggesting that deletion of the SOCS3 gene in the liver modulates insulin sensitivity in other organs. Anti-inflammatory reagent, sodium salicylate, partial improved insulin resistance of aged L-SOCS3 cKO mice, suggesting that enhanced inflammatory status is associated with the phenotype of these mice. STAT3 was hyperactivated and acute-phase proteins were elevated in L-SOCS3 cKO mice liver, which were reduced by sodium salicylate treatment. We conclude that hepatic SOCS3 is a mediator of insulin resistance in the liver; however, lack of SOCS3 in the liver promotes systemic insulin resistance by mimicking chronic inflammation. [source]

    Root and canal morphology of permanent mandibular molars in a Sudanese population

    H. A. Ahmed
    Abstract Aim, To investigate variations in the root canal systems of first and second permanent mandibular molar teeth in a Sudanese population using a clearing technique. Methodology, Two hundred extracted first and second permanent mandibular molars from three cities in the state of Khartoum were studied. Access cavities were prepared and pulp tissue was removed by immersion in 5% sodium hypochlorite under ultrasonication; Indian ink was then injected into the root canal systems assisted by a vacuum applied apically. The teeth were rendered clear by demineralization and immersion in methyl salicylate before evaluation. The following observations were made (i) number of roots and their morphology; (ii) number of root canals per tooth; (iii) number of root canals per root and (iv) root canal configuration. Results, Overall 59% of mandibular first molars had four canals with 3% having a third distolingual root. Seventy-eight per cent of second mandibular molars had two separate flat roots, whilst 10% were C-shaped. The most common canal system configurations were type IV (73%) and type II (14%). Inter-canal communications were more common in the mesial roots. The prevalence of inter-canal communications was 65% in first molars and 49% in second molars. Conclusions, In this sample of Sudanese teeth, 59% of the mandibular first permanent molars had four root canals whilst 10% of the mandibular second molars had C-shaped roots/canals. [source]

    Root and canal morphology of maxillary first and second permanent molar teeth in a Ugandan population

    C. M. Rwenyonyi
    Abstract Aim, To investigate the root and canal morphology of permanent maxillary molar teeth from a Ugandan population. Methodology, Maxillary first (n = 221) and second molar (n = 221) teeth were collected from patients attending dental clinics in Kampala. Teeth were prepared using a clearing technique: the pulp chambers were accessed and the teeth placed consecutively into 5% sodium hypochlorite, 10% nitric acid, then methyl salicylate. Indian ink was injected into the pulp chambers to demonstrate the canal system. Results, In the first molars, 95.9% of the teeth had separate roots. The mesiobuccal root was fused with the palatal root in 3% of specimens and with the distobuccal root in 0.5% of teeth. In the second molars, 86% of the teeth had separate roots. The mesiobuccal root was fused with the palatal root in 6.3% of specimens and with the distobuccal root in 6.8% of teeth. Apical deltas were more frequent in the mesiobuccal root when compared with distobuccal and palatal roots of both the first and second molars. A type I canal configuration (>75%) was the most frequent in all the roots of both the first and second molars. Canal intercommunications and lateral canals were more frequent in the mesiobuccal root when compared with other roots. Conclusions, The mesiobuccal root tended to have more variations in the canal system followed by the distobuccal root, whereas the palatal root had the least. The findings in root and canal morphology of this Ugandan population were different from previous studies, which may partly be attributed to racial differences. [source]

    A comparison between clearing and radiographic techniques in the study of the root-canal anatomy of maxillary first and second molars

    O. E. Omer
    Abstract Aim, To compare a clearing technique with conventional radiography in studying certain features of the root-canal system of maxillary right first and second molars. A secondary aim was to assess interexaminer agreement for these features using radiographs. Methodology, Eighty-three recently extracted permanent maxillary right first molars and 40 recently extracted maxillary right second molars from an Irish population were included. Standard periapical radiographs were taken from a buccolingual and mesiodistal direction. The specimens were then decoronated, demineralized in 10% hydrochloric acid for 8 days and then cleared using methyl salicylate. The cleared teeth were examined using a dissecting microscope (×20), and data relating to number of roots, canal type following Vertucci's classification, presence of lateral canals, presence of transverse anastomoses and position/number of apical foramina were collected. The radiographs were examined by two independent trained endodontists using an X-ray viewer and a magnifying lens (×2) in a dark room for the same features studied using the clearing technique. Results, The Kappa values for the agreement between the radiographic examiners A and B and the clearing technique and between the two examiners for the number of roots were 0.60, 0.64 and 0.53; for the root-canal type, 0.37, 0.41 and 0.42; for the number of roots with lateral canals, 0.21, 0.18 and 0.14; and for the transverse anastomoses, 0.29 for radiographic Examiner A. Radiographic Examiner B did not feel capable of accurately recognizing transverse anastomoses from the radiographs. For the position/number of apical foramina, the Kappa values were 0.33 and 0.24, respectively. In general, the Kappa values were low to modest for all comparisons. Conclusions, It is concluded that the agreement between the two radiographic examiners and the agreement between either radiographic examiner and the clearing technique were poor to moderate, indicating the limited value of radiographs alone when studying certain aspects of the root-canal system. [source]

    An empirical approach to study the occurrence of ion exchange in the ionic micellar-mediated semi-ionic reactions: Kinetics of the rate of reaction of piperidine with ionized phenyl salicylate in the presence of cationic micelles

    M. Niyaz Khan
    Pseudo-first-order rate constants (kobs),obtained for the cleavage of ionized phenyl salicylate (PS,) at constant [NaOH], [MeCN], [CTAZ]T (total concentration of cetyltrimethylammonium chloride and bromide), [Pip]T (total concentration of piperidine), and varying concentrations of sodium cinnamate, acetate, and butanoate ([NaX]),follow the relationship: kobs = (k0 + , K[NaX])/(1 + K[NaX]), where , and K are empirical parameters. The values of , are almost independent of [CTAZ]T, while K values decrease with the increase in [CTAZ]T within its range 0.006,0.020 M. The values of , and K are explained in terms of pseudophase model of micelle coupled with an empirical relationship: KS = KS0/(1 + ,X/S [NaX]), where KS is the CTAZ micellar binding constant of PS, in the presence of NaX. © 2001 John Wiley & Sons, Inc. Int J Chem Kinet 33: 288,294, 2001 [source]

    Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients

    C. Villa
    Synopsis Solid,liquid solvent-free phase transfer catalysis (PTC) and acidic catalysis in dry media were applied, with noticeable improvement and simplification over classical procedures in a Green Chemistry context, to the synthesis of some aromatic esters useful as cosmetic ingredients: 3-methylbutyl 4-methoxycinnamate, 2-ethylhexyl 4-methoxycinnamate, 2-ethylhexyl 4-(dimethylamino)benzoate and 2-ethylhexyl salicylate, well-known ultraviolet B sunscreen filters; 4-isopropylbenzyl salicylate, UV absorber and cutaneous antilipoperoxidant; propyl 4-hydroxybenzoate and butyl 4-hydroxybenzoate (parabens), antimicrobial agents. The reactions were performed under microwave (MW) activation and conventional heating. The best results for the synthesis of cinnamic, salicylic and 4-(dimethylamino)benzoic esters were achieved by in situ preformed carboxylates alkylation with alkyl bromides using PTC. The 4-hydroxybenzoates were obtained in good yields by classical esterification of the acid with alcohols using a simple heterogeneous mixture of reagents with catalytic amounts of p -toluenesulfonic acid (PTSA). The comparisons of yields and thermal profiles under either MW or conventional heating were studied and reported. Résumé La catalyse par transfert de phase (CTP) solide-liquide sans solvant et l'estérification acido-catalysée en ,,milieu sec'' ont été appliquées, dans le cadre de la ,,chimie verte'', avec des nettes améliorations et simplifications par rapport aux méthodes classiques, à la synthèse de certains esters aromatiques, ingrédients cosmétiques: 3-methylbutyl 4-méthoxycinnamate, 2-éthylhéxyl 4-méthoxycinnamate, 2-éthylhéxyl 4-(diméthylamino) benzoate et 2-éthylhéxyl salicylate, filtres solaires UVB bien connus; 4-isopropylbenzyl salicylate, filtre UV et antilipopéroxydant cutané; propyl 4-hydroxybenzoate et butyl 4-hydroxybenzoate (parabens), agents antimicrobien. Les réactions ont été procédées sous irradiation micro-onde et par chauffage classique. Pour la synthèse des esters dérivés de l'acide cinnamique, salicylique et 4-(diméthylamino)benzoïque les meilleurs résultats ont été obtenus grâce à la CTP par alkylation des carboxylates (préformés in situ) avec des bromures d'alkyle. Les esters de l'acide 4-hydroxybenzoique ont été obtenus avec de bons rendements par simple mélange hétérogène des réactifs et d'acide p-toluènesulfonique (PTSA) comme catalyseur. Les rendements et les profils de montée en température sous micro-ondes et par chauffage classique ont été comparés. [source]

    Dosage de l'octyl dimethyl PABA, de l'homosalate et de l'octyl salicylate dans les produits de protection solaire

    M.-O. Masse
    Résumé La méthode décrit le dosage de l,octyl dimethyl PABA (2-ethylhexyl 4-(dimethylamino)benzoate) (CAS RN 21245-02-3), de l,homo-salate (3,3,5-trimethylcyclohexyl salicylate) (CAS RN 118-56-9) et de l,octyl salicylate (2-ethylhexyl salicylate) (CAS RN 118-60-5) dans les produits cosmétiques de protection solaire. L,échantillon est mis en suspension dans le méthanol et après traitement approprié, le dosage est effectué par HPLC/UV. La précision, le rendement et la fiabilité de la méthode ont été déterminés. Synopsis The method describes the quantitative determination of octyl dimethyl PABA (2-ethylhexyl 4- (dimethylamino)benzoate) (CAS RN 21245-02-3), homosalate (3,3,5-trimethylcyclohexyl salicylate) (CAS RN 118-56-9) and octyl salicylate (2-ethylhexyl salicylate) (CAS RN 118-60-5) in cosmetic sunscreen products. The sample is suspended in methanol and after appropriate treatment the determination is made by HPLC/UV. Accuracy, yield and viability of the method were resolved. [source]

    Approaching risk assessment of complex disease development in horse chestnut trees: a chemical ecologist's perspective

    A. B. Johne
    Abstract The chemo-ecological predispositions were investigated for the development of a complex disease on the basis of an insect,fungus mutualism using the system of horse chestnuts (Aesculus hippocastanum and Aesculus x carnea), the horse chestnut leaf miner (Cameraria ohridella) and the biotrophic powdery mildew (Erysiphe flexuosa). Both C. ohridella and E. flexuosa can appear on the same horse chestnut leaf tissue simultaneously. The olfactory detection of fungal infection by the insect, its ability to discriminate the potentially mutualistic fungus from other fungi and the impact of fungal infection on insect oviposition were examined. Gas chromatography coupled with mass spectroscopic and electroantennographic detection by C. ohridella (GC-MS/EAD) was used to assess the olfactory detection of fungal-infected A. hippocastanum and A. x carnea leaves by C. ohridella. Infection-related compounds, such as benzyl alcohol, dodecane, tridecane and methyl salicylate as well as fungus-related C8 compounds, are perceived by C. ohridella. The discrimination of E. flexuosa from another phytopathogenic fungus, such as Guignardia aesculi, is based primarily on the differing pattern of C8 compounds of these fungi. Oviposition on fungal-infected leaves of A. hippocastanum and leaves treated with fungal-related compounds showed that C. ohridella is able to respond to the modifications in the leaf volatile profiles of horse chestnuts caused by the different fungal infections. Thus, from the perception point of view, the necessary predispositions for the development of a close insect,fungus relation between the biotrophic fungus E. flexuosa and the leaf-mining insect C. ohridella are fulfilled. However, decreased oviposition on infected leaves does not enhance the selective contact between the species. As a consequence, an important predisposition for forming an insect,fungus mutualism is not fulfilled by these two species and, according to this approach, the risk of forming a complex disease can be assessed as low. [source]

    Oestrogenic activity of benzyl salicylate, benzyl benzoate and butylphenylmethylpropional (Lilial) in MCF7 human breast cancer cells in vitro

    A. K. Charles
    Abstract Benzyl salicylate, benzyl benzoate and butylphenylmethylpropional (Lilial) are added to bodycare cosmetics used around the human breast. We report here that all three compounds possess oestrogenic activity in assays using the oestrogen-responsive MCF7 human breast cancer cell line. At 3 000 000-fold molar excess, they were able to partially displace [3H]oestradiol from recombinant human oestrogen receptors ER, and ER,, and from cytosolic ER of MCF7 cells. At concentrations in the range of 5 × 10,5 to 5 × 10,4 m, they were able to increase the expression of a stably integrated oestrogen-responsive reporter gene (ERE-CAT) and of the endogenous oestrogen-responsive pS2 gene in MCF7 cells, albeit to a lesser extent than with 10,8 m 17, -oestradiol. They increased the proliferation of oestrogen-dependent MCF7 cells over 7 days, which could be inhibited by the antioestrogen fulvestrant, suggesting an ER-mediated mechanism. Although the extent of stimulation of proliferation over 7 days was lower with these compounds than with 10,8 m 17, -oestradiol, given a longer time period of 35 days the extent of proliferation with 10,4 m benzyl salicylate, benzyl benzoate or butylphenylmethylpropional increased to the same magnitude as observed with 10,8 m 17, -oestradiol over 14 days. This demonstrates that benzyl salicylate, benzyl benzoate and butylphenylmethylpropional are further chemical components of cosmetic products which give oestrogenic responses in a human breast cancer cell line in culture. Further research is now needed to investigate whether oestrogenic responses are detectable using in vivo models and the extent to which these compounds might be absorbed through human skin and might enter human breast tissues. Copyright © 2009 John Wiley & Sons, Ltd. [source]

    Site-specific percutaneous absorption of methyl salicylate and VX in domestic swine

    E. J. Scott Duncan
    Abstract The site specificity of the percutaneous absorption of methyl salicylate (MeS) and the organophosphate nerve agent VX (O -ethyl S -(2-diisopropylaminoethyl) methylphosphonothioate) was examined in anaesthetized domestic swine that were fully instrumented for physiological endpoints. Four different anatomical sites (ear, perineum, inguinal crease and epigastrium) were exposed to the MeS and the serum levels were measured over a 6-h time period. The dose absorbed at the ear region was 11 ,g cm,2 with an initial flux of 0.063 ,g cm,2min,1, whereas at the epigastrium region the dose absorbed was 3 ,g cm,2 with an initial flux of 0.025 ,g cm,2min,1. For this reason further studies were carried out with VX on the ear and the epigastrium only. In animals treated with agent on the epigastrium, blood cholinesterase (ChE) activity began to drop 90 min after application and continued to decline at a constant rate for the remainder of the experiment to ca. 25% of awake control activity. At this time there were negligible signs of poisoning and the medical prognosis was judged to be good. In contrast, the ChE activity in animals receiving VX on the ear decreased to 25% of awake control values within 45 min and levelled out at 5,6% by 120 min. Clinical signs of VX poisoning paralleled the ChE inhibition, progressing in severity over the duration of the exposure. It was judged that these animals would not survive. The dramatic site dependence of agent absorption leading to vastly different toxicological endpoints demonstrated in this model system has important ramifications for chemical protective suit development, threat assessment, medical countermeasures and contamination control protocols. Copyright © 2002 Crown in the right of Canada. Published by John Wiley & Sons, Ltd. [source]

    Use of methyl salicylate as a simulant to predict the percutaneous absorption of sulfur mustard

    Jim E. Riviere
    Abstract Exposure to chemical vesicants such as sulfur mustard (HD) continues to be a threat to military forces requiring protectant strategies to exposure to be evaluated. Methyl salicylate (MS) has historically been the simulant of choice to assess HD exposure. The purpose of this study was to compare the percutaneous absorption and skin deposition of MS to HD in the isolated perfused porcine skin flap (IPPSF). The HD data were obtained from a previously published study in this model wherein 400 ,g cm,2 of ]14C[-MS or ]14C[-HD in ethanol were topically applied to 16 IPPSFs and experiments were terminated at 2, 4 or 8 h. Perfusate was collected at increasing time intervals throughout perfusion. Radioactivity was determined in perfusate and skin samples. Perfusate flux profiles were fitted to a bi-exponential model Y(t) = A(e, , e,) and the area under the curve (AUC), peak flux and time to peak flux were determined. Sulfur mustard had more pronounced and rapid initial flux parameters (P < 0.05). The AUCs determined from observed and model-predicted parameters were not statistically different, although the mean HD AUC was 40,50% greater than MS. The HD skin and fat levels were up to twice those seen with MS, but had lower stratum corneum and residual skin surface concentrations (P < 0.05). Compared with other chemicals studied in this model, HD and MS cutaneous disposition were very similar, supporting the use of MS as a dermal simulant for HD exposure. Copyright © 2001 John Wiley & Sons, Ltd. [source]

    O -acetylation of GD3 prevents its apoptotic effect and promotes survival of lymphoblasts in childhood acute lymphoblastic leukaemia

    Kankana Mukherjee
    Abstract We have previously demonstrated induction of O -acetylated sialoglycoproteins on lymphoblasts of childhood acute lymphoblastic leukaemia (ALL). These molecules promote survival of lymphoblasts by preventing apoptosis. Although O -acetylated sialoglycoproteins are over expressed, the status of O -acetylation of gangliosides and their role in lymphoblasts survival remains to be explored in ALL patients. Here, we have observed enhanced levels of 9- O -acetylated GD3 (9- O -AcGD3) in the lymphoblasts of patients and leukaemic cell line versus disialoganglioside GD3 in comparison to the normal cells. Localization of GD3 and 9- O -AcGD3 on mitochondria of patient's lymphoblasts has been demonstrated by immuno-electron microscopy. The exogenous administration of GD3-induced apoptosis in lymphoblasts as evident from the nuclear fragmentation and sub G0/G1 apoptotic peak. In contrast, 9- O -AcGD3 failed to induce such apoptosis. We further explored the mitochondria-dependent pathway triggered during GD3-induced apoptosis in lymphoblasts. GD3 caused a time-dependent depolarization of mitochondrial membrane potential, release of cytochrome c and 7.4- and 8-fold increased in caspase 9 and caspase 3 activity respectively. However, under identical conditions, an equimolar concentration of 9- O -AcGD3 failed to induce similar effects. Interestingly, 9- O -AcGD3 protected the lymphoblasts from GD3-induced apoptosis when administered in equimolar concentrations simultaneously. In situ de- O -acetylation of 9- O -AcGD3 with sodium salicylate restores the GD3-responsiveness to apoptotic signals. Although both GD3 and 9- O -acetyl GD3 localize to mitochondria, these two structurally related molecules may play different roles in ALL-disease biology. Taken together, our results suggest that O -acetylation of GD3, like that of O -acetylated sialoglycoproteins, might be a general strategy adopted by leukaemic blasts towards survival in ALL. J. Cell. Biochem. 105: 724,734, 2008. © 2008 Wiley-Liss, Inc. [source]

    Assessment of naphthalene biodegradation efficiency of Pseudomonas and Burkholderia strains tested in soil model systems,

    Andrei E Filonov
    Abstract The kinetic parameters of the naphthalene degradation process performed by indigenous and introduced microorganisms were studied in soil model systems. The introduction of active naphthalene-degrading strains Pseudomonas putida BS3701 and G7 in soil model systems accelerated the naphthalene destruction process by a factor of three to four. Moreover, the addition of salicylate (0.1 mg g,1 dry soil) to the systems containing the introduced microbial strains again doubled the rate of the naphthalene degradation process. To provide a quantitative assessment of the naphthalene biodegradation process, a mathematical model describing the bacterial growth, the consumption of the naphthalene, the production and subsequent consumption of naphthalene cleavage products, and the consumption of organic soil substances in soil model systems was developed. An approach for assessment of the degradation efficiency of low solubility polycyclic aromatic hydrocarbon provided by bacteria of genera Pseudomonas and Burkholderia in soil was suggested. The approach will enable comparison and selection of the most active degraders, which have the potential for application in biotechnologies for cleaning of soils contaminated by polycyclic aromatic hydrocarbons. Copyright © 2005 Society of Chemical Industry [source]

    Drug,herb interactions: unexpected suppression of free Danshen concentrations by salicylate

    Deepali Gupta
    Abstract The general population of the U.S. uses over-the-counter herbal medicines. Danshen is a Chinese herbal product used for the treatment of cardiovascular disease. In a previous study we showed that Danshen has significant digoxin-like immunoreactivity, and we used this parameter to monitor total and free Danshen activities in sera (10). In this report we demonstrated strong protein binding of Danshen (50,70%), and we also identified albumin as the major serum protein that binds Danshen. Because salicylate, which is also strongly bound to albumin, is a widely used over-the-counter medicine in the U.S., we studied Danshen,salicylate interaction in vitro. We observed no significant change in free Danshen concentrations as measured by free-digoxin-like activity when salicylate concentrations were subtherapeutic (,100 ,g/mL). With therapeutic concentrations of salicylate (,150 ,g/mL), the free Danshen concentrations significantly decreased from the control. On the other hand, Danshen can displace salicylate from protein binding, thereby increasing the free salicylate concentration. We conclude that salicylate in therapeutic concentration can significantly decrease free Danshen concentrations, and Danshen can displace salicylate. J. Clin. Lab. Anal. 16:290,294, 2002. © 2002 Wiley-Liss, Inc. [source]

    Synthesis of 5-ethyl-2-{5-[4-(2-hydroxyethyl)piperazin-1-ylsulfonyl]-2- n -propoxyphenyl}-7- n -propyl-3,5-dihydro-4H -pyrrolo[3,2- d]-[2- 14C]pyrimidin-4-one·2 HCl (14C-SK3530·2 HCl)

    Hyun-Il Shin
    Abstract A new 14C-labelled PDE5 inhibitor, 5-ethyl-2-{5-[4-(2-hydroxyethyl)piperazin-1-ylsulfonyl]-2- n -propoxyphenyl}-7- n -propyl-3,5-dihydro-4H -pyrrolo[3,2- d ]-[2- 14C]pyrimidin-4-one·2 HCl (14C-SK3530·2 HCl) (1·2 HCl) was synthesized through a straightforward six-step sequence from the readily available [14C-carbonyl]methyl salicylate (2). The overall radiochemical yield of the 1·2 HCl from 2 was 10.5%, and its radiochemical purity was 98.8%. Copyright © 2006 John Wiley & Sons, Ltd. [source]