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PubMed1999

Analysis of skin disposition of flurbiprofen after topical application in hairless rats.

Cutaneous disposition of topically applied flurbiprofen (FP) was evaluated using a new in situ experimental model in hairless rats. A disk-shaped agar gel (3.85 cm in diameter and 0.5 cm in thickness) was subcutaneously implanted in the abdominal region of rats as a drug receptor, and a drug donor cell was subsequently placed above this agar gel. No significant pharmacokinetic modification of FP was observed as a result of this experimental procedure. A bolus injection and a constant intravenous infusion of FP were applied to the rats, followed by an analysis of FP levels in the plasma and agar gels. Using these results, the clearance rate of FP from the systemic circulation to the gel could be calculated. FP (1% gel formulation, 1.0 g/3.14 cm(2)) was then topically applied to the skin of these rats. From these experiments, the amount of FP that migrated from the formulation to the systemic circulation and the amount of FP that migrated directly to the agar gel across the skin, over 10 h, were separately evaluated to be 235.4 and 2.0 microg, respectively. Thus, most of the FP was absorbed into the systemic circulation. The effect of endogeneous vasoactive compounds and penetration enhancers on the FP disposition within skin was also determined. Epinephrine and bradykinin were used as vasoactive compounds that were entrapped in agar gel, and an isopropyl myristate system (IPM system) and a l-menthol-ethanol-glycerin-water system (MEGW system) were used as enhancers in the formulation. Epinephrine enhanced the direct delivery of FP into the agar gel to more than ten times its former level, in spite of the fact that it had no effect on systemic delivery. Bradykinin strengthened systemic delivery slightly, without changing the quantity of FP in the gel. IPM increased only the systemic delivery of FP, as was the case with bradykinin, whereas the MEGW system markedly increased both the blood concentration and the quantity of FP in the gel (13 and 200 times, respectively). This technique has proven to be an effective tool for the quantitative evaluation of cutaneous disposition of a topically applied drug.

Administration, Cutaneous↗
PubMed1989

How to instruct patients sensitive to fragrances.

Patients who are sensitive to fragrances should either use fragrance-free cosmetics or undergo a repeat open application test to the cosmetic or perfume to determine sensitivity. Unusual reactions include systemic contact dermatitis due to balsam of Peru, benzyl alcohol, and menthol. Some responses involve pigmented eruptions due to phototoxic or photoallergic agents in perfumes and incense. Other reactions include consort dermatitis and reactions to toothpastes, gum and perfumes in paper products, sanitary napkins, ostomy pastes, and detergents.

Balsams↗
PubMed1982

Effect of a proprietary rubefacient "Tiger Balm" on rabbit skin.

The effect of continuous exposure to proprietary rubefacients (Tiger Balm Red and Tiger Balm White), which contain menthol and camphor as well as clove, cajuput and cassia oils, was tested in rabbits. Dermal irritancy was determined by a 21-day continuous-application patch test (0.5 g/patch) and was assessed according to the Draize method of scoring. At the end of the 21-day test period, the skin was also examined histopathologically. In these tests, Tiger Balm Red (which contained 5% cassia oil plus 5% clove oil) caused irritation consisting of erythema, eschar formation and some oedema, to which a degree of tolerance developed. This irritation resulted in hyperkeratosis and sometimes inflammatory changes but no major damage to the skin. Tiger Balm White (no cassia oil and 2% clove oil) was better tolerated and produced less irritation and histological change than either TIger Balm Red or a mixture of commercial waxes similar in composition to the wax base for Tiger Balm Red. None of the treatments produced any signs of systemic toxicity.

Animals↗
PubMed1997

Smoking habits and attitudes in a methadone maintenance treatment population.

This study characterized smoking habits and attitudes about quitting in methadone maintenance treatment (MMT) patients, with attention to race and gender differences. Of 179 patients surveyed, 92% (n = 165) were current smokers. These patients reported smoking a mean of 24.8 cigarettes per day. Mean age at smoking initiation was 13.6 years with 53% starting at age 13 or younger. The mean Fagerstrom tolerance questionnaire (FTQ) score was 7.5. Blacks as compared to Whites smoked fewer cigarettes per day (21.6 versus 27.5), had lower expired CO levels (18.8 versus 21.6 ppm), but higher urinary cotinine levels (1812 versus 1419 ng/ml) and were more likely to smoke menthol cigarettes (95 versus 46%). Females scored higher than males on the FTQ measures of nicotine dependence (8.0 versus 7.2), and lower than males on a measure of quit smoking self-efficacy. Subjects in the sample as a whole were well aware of health risks of smoking, as indicated by high scores on health risk perception questions. Sixty-one percent (n = 110) of subjects planned to quit within the next 6 months, 57% were 'very interested' in an on-site quit smoking program and 80% expressed interest in using nicotine replacement products. Overall, these results indicate high rates of smoking in MMT patients, confirm within a drug abusing population prior findings of racial differences in smoking habits, and suggest that MMT patients are interested in quitting and in using nicotine replacement products. The data support feasibility of implementing smoking cessation treatments with this population in a setting that allows for convenient access to patients and close monitoring of progress.

Adult↗
PubMed2002

Preparation and in vitro characterization of a eutectic based semisolid self-nanoemulsified drug delivery system (SNEDDS) of ubiquinone: mechanism and progress of emulsion formation.

The objectives of the present work were, first, to develop a self-nanoemulsified drug delivery system (SNEDDS) based on the eutectic properties of ubiquinone (CoQ10); and second, to study the progress of emulsion formation and drug release mechanisms by turbidimetry and droplet size analysis. Binary phase diagrams of CoQ10 with menthol and essential oils were constructed and used to develop the self-nanoemulsified formulation. Pseudo ternary phase diagram was constructed to identify the efficient self-emulsification region. Release mechanisms of the resultant formulas were quantified using turbidimetry in combination with dissolution studies. Turbidity time profiles revealed three distinctive regions: lag phase, plateau, and the pseudolinear phase. Lag phase was attributed to the liquid crystalline properties of the formula. Plateau turbidity was correlated with droplet size. Laser diffraction analysis revealed an average droplet diameter of 100 nm. Emulsification rate was obtained from the corrected slope of the pseudolinear phase of the profile. Stability of the formula was further evaluated using Fourier transform-infrared (FT-IR) attached to an attenuated total reflectance (ATR) accessory. The present study revealed a eutectic based semisolid self-emulsified delivery system that can overcome the drawbacks of the traditional emulsified systems such as low solubility and irreversible precipitation of the active drug in the vehicle with time.

Calorimetry, Differential Scanning↗
PubMed2003

Common herbs, essential oils, and monoterpenes potently modulate bone metabolism.

During our survey of herbs looking for activity on bone metabolism, we found that the dried leaves of sage strongly inhibit bone resorption. Therefore, we investigated several common herbs rich in essential oils (sage, rosemary, and thyme) and essential oils extracted from these herbs and other plants (oils of sage, rosemary, juniper, pine, dwarf pine, turpentine, and eucalyptus) as well as their monoterpene components (thujone, eucalyptol, camphor, borneol, thymol, alpha-pinene, beta-pinene, bornylacetate as well as menthol) and found that they inhibit bone resorption when added to the food of rats. Pine oil, used as a representative essential oil, protects an osteoporosis model, the aged ovariectomized rat, from bone loss. The monoterpenes borneol, thymol, and camphor are directly inhibitory in the osteoclast resorption pit assay. Nonpolar monoterpenes may require metabolism to be active in vitro, for example, cis-verbenol, a metabolite of alpha-pinene occurring in human urine, inhibits osteoclast activity in contrast to the parent compound. Within 30 min borneol inhibits the formation of actin rings, a characteristic of resorbing osteoclasts indicating cell polarization. Both the in vitro and the in vivo effects of borneol are reversible. Our study demonstrates for the first time that essential oils and monoterpenes are efficient inhibitors of bone resorption in the rat.

Animals↗
PubMed2002

Analytical performance of a miniature cylindrical ion trap mass spectrometer.

The analytical performance of a fieldable cylindrical ion trap (CIT)-based miniature mass spectrometer is described. A detailed description of the instrument itself is to be found in the immediately preceding paper (Patterson, G. E.; Guymon, A. J.; Riter, L S.; Everly, M.; Griep-Raming, J.; Laughlin, B. C.; Ouyang, Z.; Cooks, R. G., Miniature Cylindrical Ion Trap Mass Spectrometer, Anal. Chem. 2002, 24, 6145-6153). Applications employing the MS/MS and MSn capabilities of the miniature instrument and analytical performance criteria are given here. The limit of detection for methyl salicylate, introduced as the pure vapor, is estimated as 1 pg. The resolution, R = m/delta m, where delta m, measured as full width at half-maximum, is estimated as 100. Monitoring of organic compounds in air is performed using a permeation membrane introduction device coupled to the mass spectrometer. Water monitoring is performed using an external membrane introduction mass spectrometry (MIMS) system, with acetophenone and toluene serving as model compounds. Data are given for chemical warfare agent simulants, methyl salicylate, and dimethyl methyl phosphonate (DMMP) in air. On-line detection of menthol vapor emitted from a cough drop is reported. Methyl salicylate in air gives a recognizable mass spectrum at 400 ppb in the ambient system, while use of a heated membrane brings the detection limit down to 10 ppb.

Journal Article↗
PubMed1994

Mechanism of stimulation of the calcium adenosinetriphosphatase by jasmone.

The ATPase activity of the Ca(2+)-ATPase of skeletal muscle sarcoplasmic reticulum is increased ca. 3-fold at 25 degrees C and pH 7.2 by jasmone at a concentration of 100 microM, concentrations above 10 mM resulting in reduced stimulation. Stimulation by methyl jasmonate, menthol, or menthone requires much higher concentrations. Effects of jasmone are much less marked at 37 degrees C than at 25 degrees C, and much higher concentrations of jasmone are required to stimulate ATPase activity at pH 6.0 than at pH 7.2. The effects of jasmone on the ATPase are highly specific. Jasmone has no effect on the E1<-->E2 equilibrium constant for the ATPase or on Ca2+ binding. The rate of phosphorylation by ATP is unaffected by jasmone, and only small effects are seen on the reaction of the phosphorylated ATPase with ADP. Jasmone does, however, increase the rate of dephosphorylation by a factor of 2 and the rate of dissociation of Ca2+ from the phosphorylated ATPase by a factor of 3. Jasmone decreases the level of phosphorylation of the ATPase by P(i) in the absence of Ca2+ consistent with a decrease in the equilibrium constant E2P(i)Mg<-->E2PMg. Reconstitution of the ATPase with dimyristoleoylphosphatidylcholine decreases the stoichiometry of Ca2+ binding from the usual 2:1 to 1:1. Unlike other hydrophobic molecules, jasmone failed to reverse this effect. Further, jasmone had very similar effects on the activity of the ATPase reconstituted with either dimyristoleoylphosphatidylcholine or dioleoylphosphatidylcholine, whereas other hydrophobic molecules caused a much greater stimulation of activity for the ATPase reconstituted with the short-chain lipid.

Adenosine Diphosphate↗
PubMedDate not supplied

Catalytic polymerization of a cyclic ester derived from a "cool" natural precursor.

(-)-Menthide, a seven-membered lactone derived from the natural product (-)-menthol, was polymerized using a structurally defined zinc-alkoxide catalyst to form an aliphatic polyester. The polymer was fully characterized by NMR spectroscopy, size exclusion chromatography, and matrix-assisted laser desorption ionization mass spectrometry. The polymerization reaction occurred in a controlled fashion and polymer samples with M(n) values up to 90 kg mol(-1) were obtained by varying the catalyst loading. Monitoring of the rate of polymerization by in situ FT-IR spectroscopy (ReactIR) revealed a first order dependence on (-)-menthide. The temperature dependence of the observed rate constant between 30 and 90 degrees C was well described by the Arrhenius equation and gave E(a) = 38.4 +/- 0.9 kJ mol(-1). Thermodynamic parameters (deltaH(p) degrees = -16.8 +/- 1.6 kJ mol(-1), deltaS(p) degrees = -27.4 +/- 4.6 J mol(-1) K(-1)) for the polymerization of (-)-menthide were also determined by measuring the equilibrium monomer concentration at different temperatures ranging from 40 to 100 degrees C. The equilibrium monomer concentrations at 25 and 100 degrees C were calculated to be 0.031 +/- 0.018 and 0.120 +/- 0.063 M, respectively.

Catalysis↗
PubMedDate not supplied

In silico prediction of medium effects on esterification equilibrium using the COSMO-RS method.

This paper presents a new approach for predicting solvent effects on esterification reactions of industrial importance in the field of biocatalysis. The COSMO-RS method has been used to calculate the activity coefficients of the chemical species involved in various reactions, carried out in different solvents. For comparison we also used the traditional UNIFAC method. Three lipase-catalyzed esterifications were considered: (1) 1-dodecanoic acid with menthol in n-hexane, n-heptane, cyclohexane, 2,2,4-trimethylpentane, toluene, acetonitrile, and 2-methyl-2-butanol; (2) 1-dodecanoic acid and 1-dodecanol in n-hexane, n-heptane, cyclohexane, 2,2,4-trimethylpentane, and toluene; and (3) glycerol and n-octanoic acid in acetonitrile, benzene, and toluene and in the neat reaction mixture (without any solvent). Predicted activities were used to calculate the thermodynamic equilibrium ratio. This should be independent of medium, and the variation in COSMO-RS values is at most 9-fold (corresponding to a DeltaG degrees of about 5.5 kJ/mol, which would still be a very useful prediction) and often only 2-fold (corresponding to less than 2 kJ/mol or 0.5 kcal/mol, therefore comparable with experimental error). UNIFAC is weaker, especially when important roles are played by conformational freedom, intramolecular interactions, strong polar effects, and charge distribution of molecules in the mixture. The relative percent deviations from the mean of equilibrium constants in different solvents range between 17 and 49 for COSMO-RS versus 32 to 65 for UNIFAC. The COSMO-RS method opens up new perspectives for the development of theoretical models for solvent selection with general applicability.

Catalysis↗
PubMed2003

Electrochemical investigation of photooxidation processes promoted by sulfo-polyoxometalates: coupling of photochemical and electrochemical processes into an effective catalytic cycle.

Oxidative photocurrents measured upon irradiation by a 7-W visible light (wavelength 312-700 nm) demonstrated that the sulfo-polyoxometalate anion clusters [S2W18O62]4- (1a), [S2Mo18O62]4- (1b), and [SMo12O40]2- (2) may be activated photochemically to oxidize the organic substrates benzyl alcohol, ethanol, and (-)-menthol. In the case of catalytic photooxidation of benzyl alcohol to benzaldehyde in the presence of 1a, quantitative electrochemical methods have identified pathways for the oxidation of reduced forms of 1 generated during the catalysis. More generally, the oxidation pathways P(n+2)- + 2H+ <==> Pn- + H2 and 2P(n+2)- + O2 + 4H+ <==> 2Pn- + 2H2O have been evaluated by monitoring acidified acetonitrile solutions of the 2e(-)-reduced clusters by rotating disk electrode voltammetry under anaerobic and aerobic conditions, respectively. Neither of the reduced forms 1b(2e-) nor 2(2e-) reacted under these conditions. In contrast, 1a(2e-) was oxidized via both pathways, consistent with its more negative redox potential, with the rate of oxidation by air-oxygen being significantly faster than that by H+. The present work demonstrated that the crucial step necessary to oxidize reduced catalyst in photocatalytic reactions involving the anions studied may be achieved or accelerated by application of an external potential more positive than the first redox potential of the polyoxometalate anion. Voltammetric analysis revealed that this in situ electrolytic regeneration of the reduced catalyst is an option that leads to a viable photoelectrocatalytic pathway, even when the H+ and O2 pathways are not available.

Journal Article↗
PubMed2003

Stereospecific radical polymerization of N-triphenylmethylmethacrylamides leading to highly isotactic helical polymers.

N-Triphenylmethylmethacrylamide (TrMAM) and N-[di(4-butylphenyl)phenylmethyl]methacrylamide (DBuTrMAM) were polymerized using radical initiators. The polymer PTrMAM obtained from TrMAM was insoluble in the common solvents, but was dissolved in sulfuric acid to quantitatively give polymethacrylamide. The 1H NMR spectrum of PTrMAM in sulfuric acid-d2 indicated that the derived polymethacrylamide was nearly 100% isotactic. On the other hand, DBuTrMAM yielded the polymer PDBuTrMAM, which was soluble in THF and chloroform and whose NMR pattern in sulfuric acid-d2 was similar to that of PTrMAM. The polymerization of TrMAM and DBuTrMAM in an optically active solvent, (-)- or (+)-menthol, afforded the optically active polymers having a prevailing one-handed helical structure. The monomers were not solvolized in a methanol-chloroform mixture. TrMAM was not polymerized by anionic initiators.

Journal Article↗
PubMed2004

Helically annelated and cross-conjugated oligothiophenes: asymmetric synthesis, resolution, and characterization of a carbon-sulfur [7]helicene.

The synthesis and characterization of a novel oligothiophene, in which the thiophene rings are annelated into a [7]helicene with cross-conjugated pi-system, are described. Such [7]helicenes may be viewed as fragments of the unprecedented carbon-sulfur (C(2)S)(n)() helix, possessing sulfur-rich molecular periphery. Racemic synthesis of [7]helicene is based upon iterative alternation of two steps: C-C bond homocouplings between the beta-positions of thiophenes and annelation between the alpha-positions of thiophenes. Asymmetric synthesis is carried out using (-)-sparteine-mediated annelation of the axially chiral bis(aryllithium) with electrophilic sulfur equivalent. Alternatively, enantiomers of the [7]helicene are obtained via resolution using menthol-based chiral siloxanes. Racemic [7]helicene and four other macrocyclic products of the annelation are characterized by X-ray crystallography. One of the solvent polymorphs of the [7]helicene possesses pi-stacked columns of opposite enantiomers and multiple short intermolecular contacts, including both homochiral and heterochiral short S...S contacts, suggesting an effective intermolecular electronic coupling in two-dimensions. The [7]helicene is configurationally stable at room temperature and racemizes at 199 degrees C with a half-time of about 11 h. Selected physicochemical studies (UV-vis absorption, CD, optical rotation, and cyclic voltammetry) of the [7]helicene are described.

Journal Article↗
PubMed2002

Enzymatic synthesis of aroma compound xylosides using transfer reaction by Trichoderma longibrachiatum xylanase.

Enzymatic synthesis of aroma compound xylosides was performed by Trichoderma longibrachiatum xylanase. Information concerning the nature of xylosides present in the reaction medium was obtained by GC-EI-MS, by GC-NCI-MS of TFA derivatives, and by positive FAB-MS of the reaction mixtures. Moreover, the structures of isolated benzyl beta-D-xylopyranoside and 4-O-beta-xylopyranosyl-beta-D-xylopyranoside were established by (1)H and (13)C NMR and heteronuclear two-dimensional ((1)H-(13)C) chemical shift correlation. The results obtained for hexyl and benzyl alcohol xylosides indicated that a reaction implying a transfer of one to two or three xylose units from xylan was involved. The enzyme was able to recognize xylobiose, xylotriose, and xylan as xylose donors. Benzyl xyloside, produced independently of xylobioside and xylotrioside, was found as the major kinetic product of the reaction. Benzyl xyloside was produced in higher quantities and at a higher rate than that obtained for the di- and trixyloside derivatives. The maximum production for benzyl xyloside, 1.29 g/L, was obtained in the presence of hexane (50%) used as cosolvent. Xylosides and xylobiosides of several aroma compounds, (Z)-hex-3-en-1-ol, heptan-2-ol, geraniol, nerol, and citronellol, were synthesized in different amounts, from 850 mg/L for (Z)-hex-3-en-1-yl xylosides to 1.5 mg/L for citronellyl xylosides. No synthesis occurred when menthol, linalool, and eugenol were used as acceptors.

Alcohols↗
PubMed2003

In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone.

The major in vivo metabolites of (S)-(-)-pulegone in humans using a metabolism of ingestion-correlated amounts (MICA) experiment were newly identified as 2-(2-hydroxy-1-methylethyl)-5-methylcyclohexanone (8-hydroxymenthone, M1), 3-hydroxy-3-methyl-6-(1-methylethyl)cyclohexanone (1-hydroxymenthone, M2), 3-methyl-6-(1-methylethyl)cyclohexanol (menthol), and E-2-(2-hydroxy-1-methylethylidene)-5-methylcyclohexanone (10-hydroxypulegone, M4) on the basis of mass spectrometric analysis in combination with syntheses and NMR experiments. Minor metabolites were be identified as 3-methyl-6-(1-methylethyl)-2-cyclohexenone (piperitone, M5) and alpha,alpha,4-trimethyl-1-cyclohexene-1-methanol (3-p-menthen-8-ol, M6). Menthofuran was not a major metabolite of pulegone and is most probably an artifact formed during workup from known (M4) and/or unknown precursors. The differences in toxicity between (S)-(-)- and (R)-(+)-pulegone can be explained by the strongly diminished ability for enzymatic reduction of the double bond in (R)-(+)-pulegone. This might lead to further oxidative metabolism of 10-hydroxypulegone (M4) and the formation of further currently undetected metabolites that might account for the observed hepatotoxic and pneumotoxic activity in humans.

Cresols↗
PubMed2005

Antioxidative activity of volatile extracts isolated from Angelica tenuissimae roots, peppermint leaves, pine needles, and sweet flag leaves.

Volatile extracts were isolated from dried medicinal plants [Angelica tenuissimae roots (AT, Angelica tenuissima Nakai), peppermint leaves (PL, Mentha arvensis L.), pine needles (PN, Pinus sylvestris L.), and sweet flag leaves (SF, Acorus gramineus Rhizoma)] using steam distillation under reduced pressure, followed by continuous liquid-liquid extraction (DRP-LLE). The extracts were then analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The major volatile constituents of AT, PL, PN, and SF were 3-butylidene-4,5-dihydrophthalide (32 mg/g), menthol (18 mg/g), thunbergol (2.1 mg/g), and cis-asarone (37 mg/g), respectively. The inhibitory activity (%) of the extracts against hexanal oxidation ranged from 33 to 98% at a level of 50 microg/mL. Among the volatile extracts, PL and PN increased cell viabilities by 10 and 24%, respectively, at a dose of 1 microg/mL, compared to that of H2O2-treated brain neuroblastoma cells, SK-N-SH. However, a 20% reduction in the malonaldehyde level, an index for lipid peroxidation, was observed at only 1 microg/mL concentration of PN.

Acorus↗
PubMed2005

The effect of solvent interactions on alpha-, beta-, and gamma-cyclodextrin/flavor molecular inclusion complexes.

Three commonly used flavor industry solvents (propylene glycol, triacetin, and triethyl citrate) were tested for their capacity to interfere with the ability of alpha-, beta-, and gamma-cyclodextrin to form molecular inclusion complexes with flavors. Six flavor compounds (ethyl butyrate, ethyl heptanoate, l-menthol, methyl anthranilate, neral, and geranial) were measured by headspace gas chromatography above 2:1 water/ethanol containing appropriate additions of cyclodextrin and flavor solvent. The smallest and most polar solvent molecule represented by propylene glycol had the least effect on cyclodextrin/flavorant complex formation. In contrast, triacetin, intermediate in size among the three flavor diluents studied, had the greatest effect, even though, based on at least some computed molecular parameters, it appears to be more polar than triethyl citrate. The explanation for this apparent anomaly may lie in differences in the extent to which triacetin and triethyl citrate are able to interact with cyclodextrins by means of partial interaction with the hydrophobic cavities of the latter.

Citrates↗
PubMed2006

Volatile monoterpenes in black currant (Ribes nigrum L.) juice: effects of heating and enzymatic treatment by beta-glucosidase.

Changes of terpenes in black currant juice induced by the action of heat were investigated in the present study. Limonene, alpha-terpinene, linalool, alpha-terpineol, 4-terpineol, and menthol added to either black currant juice or a model system were thermally treated at 90 degrees C for 30 min. Similar heat-induced decreases in the concentration of the terpenes were observed in the two systems. The concentration of a range of terpene hydrocarbons and oxygenated terpenes increased, alpha-terpineol being a main conversion product of most of the examined compounds. In the main, the measured loss of compounds exceeded the detected concentrations of products formed. In addition, determination of glycosidically bound terpenes in the juice was carried out by two methods of enzymatic hydrolysis, namely, addition of beta-glucosidase to an Amberlite XAD-2 isolate or directly to black currant juice. The two methods gave the same patterns of seven released volatile aglyconic terpenes. However, none of the released terpenes are important for the odor of black currant juice.

Beverages↗