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PubMed1997

Gas chromatographic method using electron-capture detection for the determination of musk xylene in human blood samples. Biological monitoring of the general population.

Musk xylene (2,4,6-trinitro-1,3-dimethyl-5-tert.-butylbenzene, MX), a synthetic musk often used in different fragrances and soaps to substitute the natural musk, is a potential contaminant of humans. In this publication, a specific and sensitive detection method for the determination of musk xylene in human blood samples is described. The clean-up of the blood samples includes an extraction step followed by a solid-phase adsorption to separate MX from other plasma components. Separation and detection was carried out by capillary gas chromatography and an electron capture detector (GC-ECD). The results were verified using qualitative capillary gas chromatography and a mass selective detector with electron impact ionisation (GC-EI-MS). epsilon-Hexachlorocyclohexane (epsilon-HCH) is used as internal standard. The reliability of the GC-ECD method has been proved. The relative standard deviations of the within-series imprecision were 12.7% for samples with a concentration of 0.5 microg/l and 2.1% for samples with a concentration of 5.0 microg/l, whereas the relative standard deviations for the between-day imprecision were 14.9% (0.5 microg/l samples) and 3.4% (5.0 microg/l samples). The losses during sample treatment were between 10.1% and 17.8%. No interfering peaks were observed. The absolute detection limit was 0.1 microg/l plasma. A total of 72 human blood samples were analysed to determine the MX concentrations within the general population. In 66 of the 72 human blood samples, the MX concentrations ranged from 0.10 to 1.12 microg/l plasma for the described method. In six samples no MX was detected. The median concentration was 0.24+/-0.23 microg MX/l plasma. The 95 percentile was 0.79 microg/l. No correlation could be found between MX concentrations and smoking habit, broca index, age, sex as well as fish consumption habits. Nevertheless, the results demonstrate the exposure of the general population to MX.

Chromatography, Gas↗
PubMed2002

Application of microencapsulation in textiles.

The textile roots of yeast microencapsulation technology was introduced as were the wide range of applications in food and other business sectors. In microencapsulation in general the number of commercial applications in the textile industry continues to grow particularly in the textile industries of Western Europe, Japan and North America. The move by the more developed countries into textiles with new properties and added value, into medical textile and technical textiles for example has encouraged the industry to use microencapsulation processes as a means of imparting finishes and properties on textiles which were not possible or cost-effective using other technology. Textile manufacturers are demonstrating increasing interest in the application of durable fragrances to textile as well as skin softeners. Other potential applications include, insect repellents, dyes, vitamins, antimicrobials, phase change materials and in specific medical applications, antibiotics, hormones and other drugs. Examples of each technology are described. A short summary of a new microencapsulation technology with roots in the textile industry, yeast based microencapsulation, is also described.

Coloring Agents↗
PubMed2003

Fatalities due to methyl alcohol intoxication in Turkey: an 8-year study.

The aim of this study is to examine methyl alcohol poisoning cases from the medico-legal point of view. The records of the Morgue Department of Council of the Forensic Medicine were reviewed retrospectively for all methyl alcohol poisonings for the period of 27.10.1992 and 30.05.2001. The victim's age, sex, death year, death place, methyl alcohol blood levels, the source of methyl alcohol, accompanying laboratory results and histopathologic tissue changes were recorded. The number of deaths due to the methyl alcohol poisoning was 271 during that period of time. Two hundred and forty-two of the (89.3%) total 271 methyl alcohol fatalities were men and 29 (10.7%) of were women. The largest age group was 36-40 years old, followed by 41-45. The methyl alcohol blood concentrations ranged widely from 50 to 755 mg for per 100 ml. There were 222 cases (81.9%) with the methyl alcohol blood concentrations over 100 mg/dl. Twenty-nine (10.7%) victims were poisoned through the consumption of cologne and three of them with alcoholic beverage named "Raki". Consumed products were not known in all other cases because of insufficient patient history and data. As a conclusion, regarding the distribution according to years, mortality due to methyl alcohol intoxication in our country have been proceeding on a certain level. In order to decrease the mortality due to methyl alcohol intoxication, some precautions should be developed that could prevent the production and consumption of alcoholic beverages illegally produced.

Adolescent↗
PubMed1998

GC-MS analysis of incenses for possible presence of allergenic nitromusks.

A Gas chromatographic method with mass detector was developed to identify and determine nitromusks in incense sticks of different origin (India, China, Tibet). The proposed method was found useful to correlate dermatological allergic reactions with the use and composition of commercial incense sticks. The incense sticks were powdered, extracted with methanol and after the addition of 1-eicosanol as internal standard, injected into the GC-MS, using 25 m bonded phase fused capillary column methyl, 5% phenyl silicone (0.32 mm I.D., 0.25 microns film thickness). Musk ambrette was identified and determined in one kind of chinese incense together with musk ketone and musk xylene. The latter compound was also found alone in another kind of chinese incense.

Allergens↗
PubMed2003

Substituted hepta-1,6-dien-3-ones with green/fruity odours green/galbanum olfactophore model.

Following an analysis of available SAR data on green/galbanum-smelling molecules, a series of new 2-substituted hepta-1,6-dien-3-ones and their analogues were prepared and their olfactory properties evaluated. The study allowed to select efficient new odourants-potential substitutes for natural galbanum oil-and to generate an olfactophore model for the green/galbanum note.

Fruit↗
PubMed2001

Musk ketone enhances benzo(a)pyrene induced mutagenicity in human derived Hep G2 cells.

Musk ketone is a widely used artificial fragrance which has been identified in human fatty tissue and milk. The mutagenic and comutagenic effects of this compound were studied in micronucleus tests with a human derived hepatoma cell line (Hep G2). Exposure of the cells to MK alone in the range between 5 and 5000 ng/ml did not cause induction of MN. When the cells were treated simultaneously with MK (5-5000 ng/ml) and 0.2 microg/ml benzo(a)pyrene, no synergistic effects were detected; benzo(a)pyrene (B(a)P) itself caused an 1.5-fold increase of MN over the spontaneous background frequency (60 versus 39 MN/1000 binucleated cells). In a third experimental series, the cells were pretreated with MK for 28h and subsequently exposed to 0.2 microg/ml B(a)P. In this case, a pronounced comutagenic effect was observed: The LOAEL for MK was 0.05 microg/ml. With higher doses (0.5, 1.0 and 5.0 microg MK/ml), a significant increase of B(a)P induced MN frequencies was measured, the induction rates being 50, 66, and 88%, respectively. Additional measurements of 7-ethoxyresorufin deethylase indicated that MK induces cytochrome P450 isoenzymes (1A1) which play a key role in the activation of B(a)P. The results of the present study show that MK amplifies the genotoxic effects of B(a)P in human derived cells and indicate that exposure of humans to MK might increase their susceptibility to the health hazards of B(a)P and other polycyclic aromatic hydrocarbons.

Benzo(a)pyrene↗
PubMed1997

In vitro genotoxicity of polycyclic musk fragrances in the micronucleus test.

The synthetic polycyclic musk fragrance compounds galaxolide (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-(g)-2-b enzopyrane), tonalide (7-acetyl-1,1,3,4,4,6-hexamerthyltetraline), celestolide (4-acetyl-1,1-dimethyl-6-tert-butylindane), phantolide (6-acetyl-1,1,2,3,3,5-hexamethylindane), cashmeran (6,7-dihydro-1,1,2,3,3-pentamethyl-4-(5H) indanone) and traseolide (5-acetyl-1,1,2,6-tetramethyl-3-isopropylindane) were examined for their genotoxicity in the micronucleus test (MNT) with human lymphocytes in vitro in the presence and absence of an exogenous metabolizing system containing rat liver S9 and the metabolically competent human hepatoma cell line Hep G2. Compound concentrations were employed up to cytotoxic doses. Galaxolide, tonalide, celestolide, phantolide, cashmeran and traseolide revealed no genotoxicity in the micronucleus test with human lymphocytes and with the human hepatoma cell line Hep G2.

Adult↗
PubMed1999

Genotoxicity tests with 6-acetyl-1,1,2,4,4,7-hexamethyltetraline and 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-gamma-2-benzopyr an.

6-Acetyl-1,1,2,4,4,7-hexamethyltetraline (AHTN) and 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-gamma-2-ben zopyran (HHCB), synthetic fragrance ingredients, were evaluated for potential genotoxicity in a battery of short-term tests. Salmonella typhimurium/Escherichia coli plate incorporation and liquid preincubation assays were conducted on AHTN using tester strains TA97, TA98, TA100, TA102, TA1535, TA1537 and WP2 uvrA +/- S9 activation at doses from 8 to 5000 micrograms/plate. The plate incorporation mutagenicity assay was conducted on HHCB using tester strains TA98, TA100, TA1535, TA1537, TA1538 and WP2 uvrA +/- S9 activation at doses from 10 to 5000 micrograms/plate. An in vitro cytogenetics assay in Chinese hamster ovary (CHO) cells was conducted with AHTN and HHCB at three concentrations each with +/- S9 activation. In the non-activated study, the exposure/harvest periods were 4/20-, 20/20- and 44/44-h. In the S9 activated study, the exposure/harvest periods were 4/20- and 4/44-h. In vitro unscheduled DNA synthesis (UDS) assays were conducted in primary rat hepatocytes at concentrations between 0.15 and 50 micrograms/ml for AHTN and HHCB. In vivo mouse micronucleus assays were conducted with high doses of 1600 mg AHTN/kg and of 1500 mg HHCB/kg in corn oil. No positive responses were observed in any of the tests with HHCB. With AHTN, no positive responses were observed except for cells with structural aberrations in the in vitro cytogenetics assay in CHO cells with S9 activation at the treatment/harvest time of 4/20 h. In initial studies with AHTN, the high dose of 7.8 micrograms/ml showed 0.5% aberrant cells, with the mitotic index at 41% relative to vehicle control and cell growth inhibition in the range of 25-50%. Thus the genotoxicity findings with AHTN were limited to this one positive response; all other genotoxicity tests with AHTN were considered as negative. In particular, the negative finding in the in vivo assay supports AHTN as not likely to be mutagenic in mammalian systems. These considerations, along with other negative published data, lead to the conclusion that both AHTN and HHCB do not have significant potential to act as genotoxic carcinogens.

Animals↗
PubMedDate not supplied

Effect of reaction parameters on synthesis of citronellyl methacrylate by lipase-catalyzed transesterification.

The methacrylate ester of citronellol was synthesized using various lipases as catalyst. The effect of different reaction parameters such as amount of lipase, solvent, temperature, and acylating agent on the conversion of citronellol to citronellyl methacrylate was studied. Methyl methacrylate, vinyl methacrylate, and 2,3-butanedione mono-oxime methacrylate were used as acylating agents. Porcine pancreatic lipase (PPL), Candida rugosa lipase (CRL), and Pseudomonas cepacia lipase (Amano-PS) were used as biocatalysts. Diisopropyl ether (DIPE) was found to be the most suitable solvent. The stereoselectivity of CRL in transesterification of (+/-)-citronellol was tested for the optimized reaction parameters.

Acyclic Monoterpenes↗
PubMedDate not supplied

Combinatorial QSAR of ambergris fragrance compounds.

A combinatorial quantitative structure-activity relationships (Combi-QSAR) approach has been developed and applied to a data set of 98 ambergris fragrance compounds with complex stereochemistry. The Combi-QSAR approach explores all possible combinations of different independent descriptor collections and various individual correlation methods to obtain statistically significant models with high internal (for the training set) and external (for the test set) accuracy. Seven different descriptor collections were generated with commercially available MOE, CoMFA, CoMMA, Dragon, VolSurf, and MolconnZ programs; we also included chirality topological descriptors recently developed in our laboratory (Golbraikh, A.; Bonchev, D.; Tropsha, A. J. Chem. Inf. Comput. Sci. 2001, 41, 147-158). CoMMA descriptors were used in combination with MOE descriptors. MolconnZ descriptors were used in combination with chirality descriptors. Each descriptor collection was combined individually with four correlation methods, including k-nearest neighbors (kNN) classification, Support Vector Machines (SVM), decision trees, and binary QSAR, giving rise to 28 different types of QSAR models. Multiple diverse and representative training and test sets were generated by the divisions of the original data set in two. Each model with high values of leave-one-out cross-validated correct classification rate for the training set was subjected to extensive internal and external validation to avoid overfitting and achieve reliable predictive power. Two validation techniques were employed, i.e., the randomization of the target property (in this case, odor intensity) also known as the Y-randomization test and the assessment of external prediction accuracy using test sets. We demonstrate that not every combination of the data modeling technique and the descriptor collection yields a validated and predictive QSAR model. kNN classification in combination with CoMFA descriptors was found to be the best QSAR approach overall since predictive models with correct classification rates for both training and test sets of 0.7 and higher were obtained for all divisions of the ambergris data set into the training and test sets. Many predictive QSAR models were also found using a combination of kNN classification method with other collections of descriptors. The combinatorial QSAR affords automation, computational efficiency, and higher probability of identifying significant QSAR models for experimental data sets than the traditional approaches that rely on a single QSAR method.

Algorithms↗
PubMed2002

Removal of fragrance materials during U.S. and European wastewater treatment.

The concentrations and removals of 16 fragrance materials (EMs) were measured in 17 U.S. and European wastewater treatment plants between 1997 and 2000 and were compared to predicted values. The average FM profile and concentrations in U.S. and European influent were similar. The average FM profile in primary effluent was similar to the average influent profile; however, the concentration of FMs was reduced by 14.6-50.6% in primary effluent. The average FM profile in final effluent was significantly different from the primary effluent profile and was a function of the design of the wastewater treatment plant. In general, the removal of sorptive, nonbiodegradable FMs was correlated with the removal of total suspended solids in the plant, while the removal of nonsorptive, biodegradable FMs was correlated with 5-day Biological Oxidation Demand removal in the plant. The overall plant removal (primary + secondary treatment) of FMs ranged from 87.8 to 99.9% for activated sludge plants, 58.6-99.8% for carousel plants, 88.9-99.9% for oxidation ditch plants, 71.3-98.6% for trickling filter plants, 80.8-99.9% for a rotating biological contactor plant, and 96.7-99.9% for lagoons. The average concentration of FMs in final effluent ranged from the limit of quantitation (1-3 ng/L) to 8 microg/L. Measured FM removal and concentrations were compared to predicted values, which were based on industry volume, per capita water use, octanol-water partition coefficient, and biodegradability.

Adsorption↗
PubMed2004

Dissipation of fragrance materials in sludge-amended soils.

A possible removal mechanism for fragrance materials (FMs) in wastewater is adsorption to sludge, and sludge application to land may be a route through which FMs are released to the soil environment. However, little is known about the concentrations and fate of FMs in soil receiving sludge application. This study was conducted to better understand the dissipation of FMs in sludge-amended soils. We first determined the spiking and extraction efficiencies for 22 FMs in soil and leachate samples. Nine FMs were detected in digested sludges from two wastewater treatment plants in Delaware using these methods. We conducted a 1-year die-away experiment which involved four different soils amended with sludge, with and without spiking of the 22 FMs. The initial dissipation of FMs in all spiked trays was rapid, and only seven FMs remained at concentrations above the quantification limits after 3 months: AHTN, HHCB, musk ketone, musk xylene, acetyl cedrene, OTNE, and DPMI. After 1 year, the only FMs remaining in all spiked trays were musk ketone and AHTN. DPMI was the only FM that leached significantly from the spiked trays, and no FMs were detected in leachate from any unspiked tray. While soil organic matter content affected the dissipation rate in general, different mechanisms (volatilization, transformation, leaching) appeared to be important for different FMs.

Adsorption↗
PubMed2005

Simulated inhalation levels of fragrance materials in a surrogate air freshener formulation.

This study measured postapplication exposure levels of fragrance materials in a surrogate air freshener formulation in an environmentally-controlled exposure room (ECER). A five-s spray was released to simulate normal consumer use conditions. Time-course airborne fragrance material levels were sampled with Tenax tubes, and aerosol size distributions were monitored with a TSI 3320 aerodynamic particle sizer. Triplicate experiments were performed for each of the control/test substances. The control substance (unfragranced formulation) experiments indicated that the airborne fragrance materials were not detected, suggesting that the base propellant formulation did not interfere with the sampling procedure or analytical results. The test substance experiments found that the higher the volatility of the fragrance material, the higherthe airborne fragrance concentration within the ECER. In the adult breathing zone height, the maximum concentrations of the nine fragrance materials ranged from 108 to 347 microg/m3 during the first minute postapplication. In the child breathing zone height, the maximum fragrance material concentrations ranged from 125 to 362 microg/m3 during 2-6 min postapplication. Particle size distributions indicated that approximately 60-70% of the generated aerosols were less than 1 microm aerodynamic diameter. Initial peak particle mass concentrations (<5 microm) were 800-1000 microg/m3 during the first minute postapplication. Following initial peak concentrations, there was approximately 10-15 min of fluctuation, and then particle levels decayed gradually and exponentiallyto near background levels. Exposure to the test formulation would originate from two components: particle-bound and vapor-phase fragrance materials. Particle-bound fragrance exposure accounted for approximately 47% and 72% of the total exposures during the first minute postapplication period in the adult and child breathing zone heights, respectively.

Aerosols↗
PubMed2005

Occurrence of synthetic musk fragrances in marine mammals and sharks from Japanese coastal waters.

In this study, the occurrence of the polycyclic musk fragrances HHCB (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[g]-2-benzopyran) and AHTN (7-acetyl-1,1,3,4,4,6-hexamethyltetrahydeonaphthalene) in marine mammals and sharks collected from Japanese coastal waters is reported. HHCB was present in the blubbers of all finless porpoises (Neophocaena phocaenoides) analyzed (n = 8), at levels ranging from 13 to 149 ng/g on a wet weight basis. A fetus sample of finless porpoise contained a notable concentration of HHCB (26 ng/g wet wt), suggesting transplacental transfer of this compound. Among 12 tissues and organs of a finless porpoise analyzed, the highest HHCB concentration was found in blubber, followed by kidney. This indicates that HHCB accumulates in lipid-rich tissues in marine mammals, which is similar to the accumulation profiles of persistent organochlorines, such as PCBs and DDTs. In general, the residue levels of AHTN and nitro musks were low or below the detection limits in finless porpoises, implying either less usage in Japan or high metabolic capacity of these compounds in this animal. HHCB was also found in the livers of five hammerhead sharks (Sphrna lewini) from Japanese coastal waters, at concentrations ranging from 16 to 48 ng/g wet wt. Occurrence of HHCB in higher trophic organisms strongly suggests that it is less degradable in the environment and accumulates in the top predators of marine food chains. This is the first report on the accumulation of synthetic musk fragrances in marine mammals and sharks.

Adipose Tissue↗