musk and acetyl-methyl-tetramethyl-tetralin

The study was aimed to conduct the bioremediation of synthetic musks by four species of white rot fungi combined with phytoremediation (Zea mays) in biosolid-amended soils where only Galaxolide (HHCB) and Tonalide (AHTN) were found as other musks were below the detection limit (0.5-2 μg/kg dw). The HHCB and AHTN concentration in natural attenuation treated soil was decreased by not more than 9%. In solely mycoremediation, Pleurotus ostreatus was found to be the most efficient fungal strain, with the higher (P < 0.05) HHCB and AHTN removal (51.3% and 46.4%). Phytoremediation-only of biosolid-amended soil was also able to remove HHCB and AHTN from soil significantly (P < 0.05) in comparison to the control treatment without plants which resulted in the final concentration for both compounds of 56.2 and 15.3 μg/kg dw, respectively. Using white rot fungus-assisted phytoremediation, only P. ostreatus decreased the HHCB content in soil significantly (P < 0.05) by 44.7%, when compared to the initial concentration. While using Phanerochaete chrysosporium, the AHTN concentration was decreased by 34.5%, which was a significantly lower concentration at the end of experiment compared to the initial value. Via fungus-assisted phytoremediation, the enzymatic activity and fungal biomass were increased, probably due to the presence of roots in association with the soil microbiome, in the process increasing the degradation of fragrances accordingly. This could lead to a higher (P < 0.05) AHTN removal in P. chrysosporium assisted phytoremediation. Estimated HHCB and AHTN bioaccumulation factors in maize were lower than 1, therefore no environmental risk would be posed.

Topics: Basidiomycota; Benzopyrans; Biodegradation, Environmental; Biosolids; Tetrahydronaphthalenes; Water Pollutants, Chemical

Synthetic musks (SMs) have drawn worldwide attention, as they are persistent, bioaccumulative, and toxic to many organisms. There is not enough information on the bioaccumulation and trophodynamic behavior of SMs in freshwater food webs to reliably understand the associated ecological risks. In this study, the concentrations of six SM congeners in fifteen aquatic species from Lake Chaohu, China, was investigated. The total concentrations of the six SMs ranged from 0.29 to 59.7 ng/g dry weight (median, 4.41) in fish muscle tissue and in the whole body tissues of small fish species and shrimps. Galaxolide (HHCB) and tonalide (AHTN) were the predominant congeners, accounting for 65.0% and 28.5% of the total SM concentration, respectively. On the whole, the total concentrations of SMs in livers and gills were 0.18-32.8 and 0.84-254 times higher than those in muscle tissues in fish species, respectively. In the food web of Lake Chaohu, cashmeran (DPMI) and HHCB showed a trend towards trophic magnification, and AHTN tended to show trophic dilution, but these trends were not statistically significant. This suggested that the trophic transfer of these chemicals through the food web was strongly influenced by many factors, including tissue-specific distribution within individuals at higher trophic levels. More investigation into the trophic transfer of SMs in aquatic ecosystems and the factors influencing uptake is needed.

Topics: Animals; Benzopyrans; Bioaccumulation; China; Ecosystem; Environmental Monitoring; Fatty Acids, Monounsaturated; Fishes; Food Chain; Humans; Lakes; Seafood; Tetrahydronaphthalenes; Water Pollutants, Chemical

A Quick, Easy, Cheap, Effective, Rugged and Safe (QuEChERS) methodology followed by gas chromatography-tandem mass spectrometry (GC-MS/MS) analysis was developed to extract thirteen synthetic musk compounds (SMCs: cashmeran, celestolide, phantolide, traseolide, galaxolide, tonalide, musk ambrette, musk xylene, musk ketone, musk tibetene, musk moskene, ethylene brassylate and exaltolide) and six ultraviolet-filters (UVFs: 2-ethylhexyl 4-dimethylaminobenzoate, 3-(4'-methylbenzylidene) camphor, 2-ethylhexyl 4-methoxycinnamate, 2-ethylhexyl 2-cyano-3,3-diphenylacrylate, benzophenone and drometrizole trisiloxane) from tomatoes. The proposed methodology was optimized: 2 g of freeze-dried tomato was extracted with 4 mL of water and 10 mL of ethyl acetate, adding 6 g of MgSO

Topics: Benzophenones; Benzopyrans; Dinitrobenzenes; Fatty Acids, Monounsaturated; Gas Chromatography-Mass Spectrometry; Indans; Solanum lycopersicum; Solid Phase Extraction; Tandem Mass Spectrometry; Tetrahydronaphthalenes; Water Pollutants, Chemical; Xylenes

Polycyclic musk compounds have been identified in environmental matrices (water, sediment and air) and in biological tissues in the last decade, yet only minimal attention has been paid to their chronic toxicity in the marine environment. In the present research, the clams Ruditapes philippinarum were exposed to 0.005, 0.05, 0.5, 5 and 50 μg/L of the fragrances Galaxolide® (HHCB) and Tonalide® (AHTN) for 21 days. A battery of biomarkers related with xenobiotics biotransformation (EROD and GST), oxidative stress (GPx, GR and LPO) and genotoxicity (DNA damage) were measured in digestive gland tissues. HHCB and AHTN significantly (p < 0.05) induced EROD and GST enzymatic activities at environmental concentrations. Both fragrances also induced GPx activity. All concentrations of both compounds induced an increase of LPO and DNA damage on day 21. Although these substances have been reported as not acutely toxic, this study shows that they might induce oxidative stress and genotoxicity in marine organisms.

Topics: Animals; Aquatic Organisms; Benzopyrans; DNA Damage; Fatty Acids, Monounsaturated; Oxidative Stress; Tetrahydronaphthalenes; Water Pollutants, Chemical

In the present study, the effect of polycyclic musk compound tonalide (AHTN) in two concentrations was studied in male rainbow trout (Oncorhynchus mykiss, Walbaum 1792). A feeding trial was conducted with AHTN incorporated into feed granules. One concentration was environmentally relevant (854 µg/kg); the second one was 10× higher (8699 µg/kg). The fish were fed twice a day with the amount of feed at 1 % of their body weight. After an acclimatization period, the experimental phase in duration of six weeks followed. At the end of the experiment, fish were sampled and the biometrical data were recorded. Subsequently, hematological and biochemical tests, histopathological examination, analysis of oxidative stress markers and evaluation of endocrine disruption using plasma vitellogenin were performed. In conclusion, an increase of hematocrit for both AHTN concentrations was found, but no significant changes were observed in biochemical profile. Moreover, AHTN caused lipid peroxidation in caudal kidney tissue, which was confirmed by histopathological images. The long-lasting AHTN exposure could thus be harmful for maintaining homeostasis in the rainbow trout organism. However, the vitellogenin concentration seemed not to be affected by AHTN.

Topics: Animals; Dose-Response Relationship, Drug; Endocrine Disruptors; Fatty Acids, Monounsaturated; Fish Proteins; Gills; Kidney; Lipid Peroxidation; Liver; Male; Oncorhynchus mykiss; Oxidative Stress; Tetrahydronaphthalenes; Vitellogenins

A novel solid phase microextraction Arrow (SPME Arrow) system has been applied for the first time to determine synthetic musk fragrances in fish samples. The lack of regulation concerning the concentration of musk fragrances in fish along with the risk associated to these compounds has led to an increased development of analytical methods on this topic. This study applies SPME Arrow followed by gas chromatography coupled to tandem mass spectrometry (ion trap) to determine nine musk fragrances and compares this novel technique with its predecessor (SPME). Parameters such as type of coating, extraction time and temperature as well as water addition were optimized to achieve higher sensitivity. Results show that detection limits ranging between 0.5 ng g

Topics: Adsorption; Animals; Fatty Acids, Monounsaturated; Fishes; Gas Chromatography-Mass Spectrometry; Perfume; Seafood; Solid Phase Microextraction; Tandem Mass Spectrometry; Temperature; Tetrahydronaphthalenes; Time Factors; Water; Water Pollutants, Chemical

The musk fragrances galaxolide (HHCB) and tonalide (AHTN) are compounds of emerging concern that have been found in various environmental compartments. The present study addressed the ability of HHCB and AHTN to elicit the avoidance response in the estuarine shrimp Palaemon varians and to predict the population immediate decline (PID) of P. varians when exposed to HHCB and AHTN by integrating both avoidance (non-forced exposure) and lethality (forced exposure) responses. The avoidance response was tested in a non-forced multi-compartmented static system, in which the shrimps could move freely among the compartments with different concentrations. The shrimps (n = 3 shrimps per compartment/concentration; 18 shrimps per system) were exposed to a gradient (0, 0.005, 0.05, 0.5, 5 and 50 μg/L) of both substances and their positions were checked at every 20 min for a 3 h period. The results from 24-h forced exposure showed no dose-response relationship and the highest percentage mortality was 17% for HHCB at 0.005 and 0.5 μg/L. In the 3-h non-forced exposure to a gradient of HHCB and AHTN, significant concentration-dependent spatial avoidance was observed for both substances. The shrimps avoided the lowest concentration of HHCB and AHTN (0.005 μg/L) by 15% and 16%. The avoidance increased significantly (p < 0.005) to a 61% and 57%, respectively, for the highest concentration (50 μg/L). The population immediate decline was driven by the avoidance behaviour of the shrimps rather than mortality. These results indicated that the aversiveness of HHCB and AHTN might have serious consequences for habitat selection processes by organisms.

Topics: Animals; Avoidance Learning; Benzopyrans; Fatty Acids, Monounsaturated; Palaemonidae; Perfume; Seafood; Seawater; Tetrahydronaphthalenes; Water Pollutants, Chemical

Human activity in estuarine areas has resulted in pollution of the aquatic environment, but little is known about the levels of synthetic musks (SMs) in river water and sediments in estuarine areas. This study investigated the concentrations and distribution of SMs in the Jiaozhou Bay wetland, including celestolide, phantolide, traseolide, galaxolide (HHCB), tonalide (AHTN), musk xylene and musk ketone (MK). The SMs HHCB, AHTN and MK were detected at concentrations of 10.7-208, not detected (ND)-59.2 and ND-13.6 ng/L, respectively, in surface water samples and 13.1-27.3, 3.06-14.5 and 1.33-18.8 ng/g (dry weight; dw), respectively, in sediment samples. Based on the calculated total organic carbon (TOC) concentrations, there was no significant correlation between SMs and TOC in sediment samples (p > 0.05). The hazard quotients were 0.204, 0.386 and 0.059 for AHTN, HHCB and MK, respectively, which indicated no serious environmental impact, because these values are all less than 1. The concentrations of SMs decreased as the distance to the Xiaojianxi refuse landfill increased in both surface water and sediments. Compared with previous studies, the concentration of SMs in the Jiaozhou Bay wetland was relatively high. Therefore, more attention should be paid to SMs because of their persistent impact on human health and the environment.

Topics: Bays; Benzopyrans; China; Fatty Acids, Monounsaturated; Humans; Perfume; Risk Assessment; Tetrahydronaphthalenes; Water Pollutants, Chemical; Wetlands; Xylenes

Synthetic musk compounds are widely used in the formulation of several cosmetics, personal care and household products. Due to their massive and widespread use, together with some health concerns, they are considered emerging pollutants and have been detected in different environmental compartments. This study focused on the evaluation of the concentration of synthetic musks (five nitro, five polycyclic and one macrocyclic musks) in beach sands, from Oporto coastal area (Portugal), contributing to the enhancement of the knowledge of levels, trends and behaviour of these compounds in this particular matrix. To accomplish this task, a QuEChERS methodology ("Quick, Easy, Cheap, Effective, Rugged, and Safe") coupled to gas chromatography-mass spectrometry (GC-MS) was successfully used to determine synthetic musks from beach sand. The chosen methodology proved to be suitable, achieving satisfactory results for precision (relative standard deviation values below 15%), accuracy (average recovery of 97%) and limits of detection (below 38 pg g

Topics: Bathing Beaches; Benzopyrans; Cosmetics; Dinitrobenzenes; Fatty Acids, Monounsaturated; Gas Chromatography-Mass Spectrometry; Portugal; Seasons; Tetrahydronaphthalenes; Water Pollutants, Chemical; Xylenes

Personal care products, an important class of emerging contaminants, have been frequently detected in different environmental matrices. Included in this category are synthetic musks compounds (SMCs) and UV-filters. Their occurrence in the coastal environment has been poorly studied. Therefore, this work aimed to verify whether five coastline plant species (Carpobrotus edulis, Cakile maritima, Medicago marina, Elymus farctus borealis-atlanticus and Euphorbia paralias) have the ability to accumulate 11 SMCs (cashmeran, celestolide, phantolide, galaxolide, tonalide, exaltolide, musk moskene, tibetene, ambrette, xylene and ketone) and 2 organic UVB filters (3-(4'-methylbenzylidene) camphor and octocrylene), functioning as biosamplers. To accomplish this task, a QuEChERS technique ("Quick, Easy, Cheap, Effective, Rugged, and Safe") was employed to extract the target compounds from the plant material collected in 15 beaches of Matosinhos and Vila Nova de Gaia (Portugal). The resulting extracts were analysed by gas chromatography-mass spectrometry. Limits of detection ranged from 0.02 ng g

Topics: Benzopyrans; Dinitrobenzenes; Environmental Monitoring; Fatty Acids, Monounsaturated; Gas Chromatography-Mass Spectrometry; Indans; Portugal; Receptor Protein-Tyrosine Kinases; Receptors, Cholinergic; Seawater; Sunscreening Agents; Tetrahydronaphthalenes; Water Pollutants, Chemical; Xylenes

The levels of 12 synthetic musks and one musk metabolite in 24 pooled human milk samples were examined in order to assess the health risks of these contaminants to breast-feeding infants of China. The 24 pooled samples comprised of 1237 individual human milk samples collected from 12 provinces of China according to WHO guidelines. Among the 13 target analytes, OTNE ([1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalen-2yl]ethan-1-one), HHCB (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[γ]-2-benzopyran), AHTN (7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene), musk ketone (4-tert-butyl-2,6-dimethyl-3,5-dinitroacetophenone, MK), Musk T (1,4-dioxacyclohepta decane-5,17-dione), HHCB-lactone (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl cyclopenta[γ]-2-benzopyran-1-one) and musk ambrette (1-(1,1-dimethylethyl)-2-methoxy-4-methyl-3,5-dinitrobenzene, MA), were found in the milk samples analysed with mean (median) concentrations of 3.96 (3.91), 18.03 (15.10), 10.30 (9.38), 4.68 (4.45), < 3.70 (< 3.70), 10.02 (9.20) and < 5.20 (< 5.20) ng g(-1) lipid weight, respectively, whereas ADBI (4-acetyl-1,1-dimethyl-6-tert-butylindan), AHDI (6-acetyl-1,1,2,3,3,5-hexamethylindan), ATII (5-acetyl-1,1,2,6-tetramethyl-3-isopropylindan), musk xylene (1-tert-butyl-3,5-dimethyl-2,4,6-trinitrobenzene, MX), musk tibetene (1-tert-butyl-3,4,5-trimethyl-2,6-dinitrobenzene, MT) and musk moskene (1,1,3,3,5-pentamethyl-4,6-dinotroindane, MM) were not detected. Significantly positive associations were observed in concentration levels between HHCB and AHTN (p < 0.001), HHCB and HHCB-lactone (p < 0.05), AHTN and HHCB-lactone (p < 0.001), and MK and OTNE (p < 0.05). No statistical difference was found in musk concentrations between rural and urban areas in China (p > 0.05). The mean (median) estimated daily intakes by infants were 20.5 (20.2), 93.4 (78.2), 53.4 (48.6), 24.2 (23.0) and 51.9 (47.6) ng kg(-1) body weight for OTNE, HHCB, AHTN, MK and HHCB-lactone, respectively. The musk exposure levels of infants in China via breast feeding were very low according to the current toxicological information.

Topics: Adolescent; Adult; China; Dinitrobenzenes; Fatty Acids, Monounsaturated; Female; Humans; Indans; Infant; Milk, Human; Recommended Dietary Allowances; Tetrahydronaphthalenes; Water Pollutants, Chemical; Xylenes

A new analytical method for the simultaneous determination of eight synthetic musks compounds (SMs) including five polycyclic musks (PCMs) and three nitro musks (NMs) was validated for sediment samples based on a simple QuEChERS (Quick, Easy, Cheap, Effective, Rugged and Safe) sample preparation procedure followed by gas chromatography-mass spectrometry (GC-MS). Good analytical performances were obtained for all the target compounds. For the validation of the method, internal calibration (IC) and internal calibration with QuEChERS (ICQ) were compared. Good linearity was obtained for both calibration methods with determination coefficients (R

Topics: Benzopyrans; Fatty Acids, Monounsaturated; Gas Chromatography-Mass Spectrometry; Tetrahydronaphthalenes; Tunisia; Xylenes

A methodology based on headspace solid phase microextraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS) determination was developed for the monitoring and evaluation of the removal efficiency of 16 common fragrance allergens and two polycyclic musks in wastewater treatment plants (WWTPs). An experimental design with a full factorial model was applied to evaluate the effects of the experimental parameters on the extraction (e.g., salt content, time and extraction temperature). After determining the optimum conditions (2.4 g NaCl, 45 min at 90 °C), an external calibration was performed and quality parameters of the proposed method were evaluated. Method detection limits in the range of 0.01-1.7 μg L(-1) were obtained. Satisfactory inter-day precision values between 4% and 23% (n=5) were obtained for most compounds. The method was applied to the monitoring of the target analytes in samples from two WWTPs. Seven target compounds were detected at the primary effluent of both plants at μg L(-1) levels. Limonene, linalool and eugenol were quantitatively eliminated during the secondary treatments of both WWTPs, while lilial, benzyl salicylate, galaxolide, and tonalide were still detected at the effluent waters.

Topics: Acyclic Monoterpenes; Aldehydes; Allergens; Benzopyrans; Cyclohexenes; Eugenol; Fatty Acids, Monounsaturated; Gas Chromatography-Mass Spectrometry; Limonene; Monoterpenes; Odorants; Perfume; Salicylates; Solid Phase Microextraction; Terpenes; Tetrahydronaphthalenes; Wastewater; Water Pollutants, Chemical

Galaxolide (HHCB), tonalide (AHTN), phantolide (AHDI), traseolide (ATII) and cashmeran (DPMI) are synthetic polycyclic musks (PCMs). They are all commonly used in fragrance industries as racemic mixtures. A sensitive and robust enantioselective analytical method was developed to facilitate measurement of these chemicals in wastewater and environmental samples. The method is based on gas chromatography with tandem mass spectrometry (GC-MS/MS). Enantioseparation was assessed using four commercially available chiral capillary columns. Optimised resolution was achieved using a dual-column configuration of a chiral heptakis(2,3- di-O-methyl-6-O-t-butyl dimethylsilyl)-β-cyclodextrin column combined with a (non-chiral) HP-5MS column. This configuration was demonstrated to be capable of effectively resolving all commercially manufactured enantiomers of these five PCMs. Method detection limits for single enantiomers in drinking water and surface water range between 1.01 and 2.39ngL(-1). Full validation of the application of this method in these aqueous matrices is provided.

Topics: Benzopyrans; Fatty Acids, Monounsaturated; Gas Chromatography-Mass Spectrometry; Indans; Perfume; Sewage; Stereoisomerism; Tetrahydronaphthalenes; Wastewater; Water Pollutants, Chemical

To investigate the changes in gene expression of earthworm specific proteins following long-term exposure to low-dose polycyclic musks in soil, the mRNA expression levels of the four representative protein-coding genes (HSP70, CRT, cyPA, TCTP) were examined in earthworm Eisenia fetida exposed to polycyclic musks using real-time quantitative PCR (RT-qPCR). The purpose of this study was to investigate mRNA expression profiles of test protein genes in response to sublethal galaxolide (HHCB) and tonalide (AHTN) for 28 d exposure. The analysis results of both sequence alignment and melting curves of RT-qPCR reactions showed that the selected primers were appropriately qualified for quantitative mRNA analysis. mRNA expressions of HSP70 gene were not significantly changed in Eisenia fetida exposed to low concentrations of AHTN (less than 30 microg x g(-1)) and HHCB (less than 50 microg x g(-1)). But HSP70 gene expressions were significantly down-regulated at concentrations of AHTN or HHCB equal to or greater than 30 or 50 microg x g(-1). However, up-regulation of CRT gene expressions was induced in response to all test concentrations of AHTN and HHCB. Both cyPA and TCTP gene expressions were not varied compared to control groups after 28 days of exposure. Overall, the results indicated that HSP70 and CRT genes expression patterns might be potential early molecular biomarkers for predicting the harmful exposure level and ecotoxicological effects of polycyclic musks contaminated soil.

Topics: Animals; Benzopyrans; Calreticulin; Environmental Exposure; Fatty Acids, Monounsaturated; HSP70 Heat-Shock Proteins; Oligochaeta; RNA, Messenger; Soil Pollutants; Tetrahydronaphthalenes

Fate of galaxolide (HHCB) and tonalide (AHTN) during the A2O process was investigated under different hydraulic retention time (HRT). Solid phase extraction (SPE) and gas chromatography mass spectrometry (GC/MS) were applied to determine the concentrations of the targets in the aqueous phase and sewage sludge. The results showed that HRT has an influence on the proportions of biodegradation and the discharge of excess sludge for HHCB by the A2O process, and it also affected the discharge of excess sludge for AHTN. With the extension of HRT, removal rates and removal contribution rates of HHCB and AHTN decreased in the anaerobic tank, while increased in the anoxic tank and aerobic tank. The final removal rates of the targets in the four operating conditions (6 h, 8 h, 10 h and 12 h) were 73.93%, 73.05%, 75.14%, 76% and 48.76%, 44.27%, 57.17%, 62.9%, respectively. The removal efficiency was good for HHCB, but the removal efficiency of AHTN was poor by the A2O process. Meanwhile, with the extension of HRT, the removal efficiency showed no significant effect on HHCB, but it promoted the removal efficiency of AHTN.

Topics: Benzopyrans; Biodegradation, Environmental; Bioreactors; Fatty Acids, Monounsaturated; Polycyclic Compounds; Tetrahydronaphthalenes; Waste Disposal, Fluid; Wastewater

Human breast milk samples collected from mothers (n=110) who lived in Chengdu, Sichuan Province, southwestern China in 2009 were analyzed to determine the concentrations of 13 musk compounds. Possible relationships between musk concentrations and some personal characteristics were also studied. Only five target analytes were detected in the milk samples analyzed, with median concentration values of 16.5, 11.5, 7.85, <1.5 and <1.4ngg(-1)lipid weight for AHTN (7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene), HHCB (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[γ]-2-benzopyran), HHCB-lactone (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[γ]-2-benzopyran-1-one), OTNE ([1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalen-2yl]ethan-1-one) and musk ketone (4-tert-butyl-2,6-dimethyl-3,5-dinitroacetophenone, MK), respectively. Mothers who reported high use of hand-cleaning agents, body-cleaning agents, shampoo and hair conditioners, hair dyes and hair gels had significantly elevated milk concentrations of HHCB whereas elevated milk concentrations of AHTN were observed among mothers reporting high use of body-cleaning agents, body lotions, shampoos, hair dyes and hair gels. Younger age showed a significantly positive effect on milk concentrations of both HHCB and AHTN whereas BMI after delivery, the number of children nursed and place of residence (urban or rural) had no significant effect. The estimated median daily intakes of synthetic musks for breast-fed infants were considerably lower than the current provisional tolerable daily intake amounts suggested for adults.

Topics: Benzopyrans; China; Fatty Acids, Monounsaturated; Female; Household Products; Humans; Infant; Maternal Age; Milk, Human; Mothers; Naphthalenes; Risk Assessment; Tetrahydronaphthalenes; Urban Population; Xylenes

The occurrence of cashmerane (DPMI), celestolide, phantolide, traesolide (ATII), galaxolide (HHCB) and tonalide (AHTN) in sewage and surface waters and their fate during wastewater treatment and anaerobic sludge digestion is investigated. AHTN and HHCB are the most important representatives and influent concentrations of 0.41-1.8 and 0.9-13 μgL(-1) are observed. DPMI is detected in influent and effluent samples but in notably lower concentrations than AHTN and HHCB. Major sources of polycyclic musks are households, whereas industrial emitters seem to be of minor importance. This conclusion is supported by the analysis of selected industrial wastewaters (metal, textile and paper industry). Specific emissions of 0.36 ± 0.19 and 1.6 ± 1.0 mg cap(-1)d(-1) for AHTN and HHCB are calculated. Overall removal efficiencies between approx 50% and more than 95% are observed during biological wastewater treatment and removal with the excess sludge is the major removal pathway. Log K(D) values of 3.73-4.3 for AHTN, 3.87-4.34 for HHCB and 2.42-3.22 for DPMI are observed in secondary sludge. During sludge digestion no or only slight removal occurred. Mean polycyclic musk concentrations in digested sludge amounted to 1.9 ± 0.9 (AHTN), 14.2 ± 5.8 (HHCB), 0.8 ± 0.4 (ATII) and 0.2 ± 0.09 (DPMI) mgkg(-1) dry matter. In the receiving water systems a comparable distribution as during wastewater treatment is observed. AHTN, HHCB and DPMI are detected in surface waters (ND (not detected) - <0.04, ND - 0.32 and ND - 0.02 μg L(-1)) as well as AHTN and HHCB in sediments (ND - 20, ND - 120 μg kg(-1)). For HHCB an apparent K(OC) value of 4.1-4.4 is calculated for sediments. Major source for polycyclic musks in surface waters are discharges from wastewater treatment plants. For HHCB and DPMI 100% of the load observed in the sampled surface waters derive from discharges of treated wastewater.

Topics: Benzopyrans; Environmental Monitoring; Fatty Acids, Monounsaturated; Fresh Water; Geologic Sediments; Indans; Perfume; Polycyclic Compounds; Sewage; Tetrahydronaphthalenes; Waste Disposal, Fluid; Water Pollutants, Chemical; Water Pollution, Chemical

Seven typical synthetic musks were measured in influents, effluents and sewage sludge from seven wastewater treatment plants of Beijing in three seasons. Galaxolide and tonalide were the dominant musks, and the levels were medium compared with those from other regions. Musk concentrations and galaxolide/tonalide ratios were low in warm seasons relative to cold seasons in both water and sludge samples. The removal efficiencies of galaxolide and tonalide ranged in <14.3%-98.0% and <18.5%-98.7%, respectively. The discharge of galaxolide and tonalide through effluents into environment were 1.8-685.6 g/d (mean: 70.1 g/d) and 1.6-195.3 g/d (mean: 22.9 g/d), respectively.

Topics: Benzopyrans; China; Environmental Monitoring; Fatty Acids, Monounsaturated; Fresh Water; Perfume; Seasons; Sewage; Tetrahydronaphthalenes; Waste Disposal, Fluid; Water Pollutants, Chemical; Water Pollution, Chemical

Seven typical synthetic musks (SMs) in the samples from the surface water, sediment and fish of the Haihe River were measured. The SM concentrations in the sediment and surface water of the Haihe River were significantly lower than those in the Dagu Drainage River and Chentaizi Drainage River (p<0.05). Along the flow direction, the SM concentrations in surface water and sediment tended to increase from the upstream to the downstream of Dagu Drainage River. The Bioaccumulation factors (BAFs) of galaxolide (HHCB) and tonalide (AHTN) were calculated at high levels in the muscles of crucian carp, common carp, and silver carp. Most of the biota-sediment accumulation factors (BSAFs) for HHCB and AHTN were higher than 1.7, suggesting magnification possibly exist in the musk bioaccumulations of the three fishes in the Haihe River. No significant differences in HHCB/AHTN ratios were observed among the water, fish, and sediment samples (p>0.05). However, the HHCB/AHTN values in the Haihe River were much lower than those in the Dagu Drainage River and Chentaizi Drainage River (p<0.05). Compared with several typical persistent organic pollutants (POPs), the musk concentrations were higher or comparable in the Haihe River.

Topics: Animals; Benzopyrans; Carps; China; Fatty Acids, Monounsaturated; Gas Chromatography-Mass Spectrometry; Geologic Sediments; Muscles; Rivers; Tetrahydronaphthalenes; Water Pollutants, Chemical

With soil culture the ecotoxicological effects of galaxolide (HHCB) and tonalide (AHTN) on the germination of wheat (Triticum aestivum) seeds were investigated. And the influence of these two synthetical musks on the wheat germination rate, inhibition rate of root elongation and inhibition rate of shoot elongation were studied. The results showed that there were no obvious dose-effect relationship between wheat germination rate and concentrations of these two synthetical musks. Lower dose (HHCB < or = 150 mg x kg(-1), AHTN < or = 200 mg x kg(-1)) could accelerate the germination of wheat. Under the test concentrations of synthetical musks, the wheat germination rates treated with HHCB and AHTN were 77.78%-95.56% and 84.44%-97.78%, respectively. There were good dose-effect relationship between inhibition rate of root elongation (or inhibition rate of shoot elongation) and synthetical musks concentrations. The EC50 of HHCB and AHTN based on shoot were 155.84 mg x kg(-1) and 290.58 mg x kg(-1), and were 215.66 mg x kg(-1) and 323.10 mg x kg(-1) based on root from linear model. The EC50 of wheat sensitive positions showed that the toxicity of HHCB was stronger than AHTN.

Topics: Benzopyrans; Ecotoxicology; Environmental Monitoring; Environmental Pollutants; Fatty Acids, Monounsaturated; Germination; Seedlings; Tetrahydronaphthalenes; Triticum

We measured two nitro musk fragrances (musk xylene) and musk ketone) and five polycyclic musk fragrances (galaxolide [HHCB], tonalide [AHTN], celestolide [ADBI], traseolide [ATII], and phantolide [AHMI]) in human blood samples from 11 cities of China (n = 204). Possible temporal trends in musk concentrations and associations with personal factors, such as gender, age, and others, were studied. Galaxolide (HHCB) showed the highest median concentration (0.85 ng/g) followed by AHTN (0.53 ng/g) with high detection frequency (91 and 77%, respectively). Concentrations of the other synthetic musk fragrances, including musk ketone and musk xylene, were all below the quantification limits. The results suggested that musk concentrations were not significantly relative to gender and body weight but positively correlated with age groups and locations. Apparent differences were also observed in the ratios of HHCB to AHTN concentrations among different cities.

Topics: Adolescent; Adult; Aged; Benzopyrans; China; Environmental Exposure; Fatty Acids, Monounsaturated; Female; Humans; Indans; Male; Middle Aged; Tetrahydronaphthalenes; Young Adult

The characteristics of occurrence and distribution of 8 synthetic musks in 15 sewage sludges in Shanghai were studied. The results indicated that HHCB and AHTN were the two main components in all sludges, with the mean concentration of 2.92 mg x kg(-1) (0.81-6.39 mg x kg(-1)) and 1.96 mg x kg(-1) (0.35-3.11 mg x kg(-1)), respectively; and the concentrations of ADBI, AHMI, MK were less. The distributions detected in sludges are in accordance with the usage patterns in China. Total concentrations of 8 synthetic musks were ranged from 1.16-9.57 mg x kg(-1), which were lower than the results in previous studies. Concentrations in sludges are influenced by ratio of domestic wastewater in influent, sewage load and sewage treatment methods. The good linear relationships among HHCB, AHTN and ADBI indicate that these components have the same source: domestic wastewater. The consumption rates of HHCB and AHTN connected to per inhabitant in Shanghai region were estimated, which are low compared with those found in European. The potential impacts on agricultural soil were also assessed.

Topics: Benzopyrans; China; Cities; Fatty Acids, Monounsaturated; Perfume; Sewage; Tetrahydronaphthalenes; Water Pollutants, Chemical; Water Purification

Synthetic musks are widely used as perfuming agents in products, such as cosmetics, detergents, and soaps. The increased detection of these substances in the aquatic environment and their high bioconcentration potential raises concerns about potential effects on aquatic species. This work aimed at assessing the interactions of the most widely used musks: nitromusks (musk xylene, musk ketone) and polycyclic musks (celestolide, galaxolide, and tonalide) with fish enzymatic systems involved in both xenobiotic and endogenous metabolism. Therefore, CYP catalyzed pathways were investigated in carp liver microsomes (CYP1A, CYP3A), ovarian microsomes (CYP19) and testicular mitochondria (CYP17 and CYP11beta) using standard substrates. Phase II activities (UDP-glucuronosyltransferases and sulfotransferases) were determined in carp liver microsomes and cytosol, respectively. Polycyclic musks (galaxolide and tonalide) were stronger inhibitors of CYP3A- (IC(50): 68-74 microM), CYP17- (IC(50): 213-225 microM), CYP11beta- and CYP19-catalyzed activities than nitromusks, while the latter showed higher ability to interfere with CYP1A (IC(50): 35-37 microM). The sulfation of estradiol was also significantly inhibited by tonalide and galoxolide (IC(50): 140-294 microM). Overall, polycyclic musks showed the highest potential to interfere with those activities involved in the synthesis and metabolism of steroids while nitromusks mainly interfered with xenobiotic metabolism (CYP1A-catalyzed reactions). The obtained data suggest that CYP isoforms are potentially sensitive targets of synthetic musk substances in fish.

Topics: Animals; Aromatase; Benzopyrans; Carps; Cytochrome P-450 CYP1A1; Cytochrome P-450 CYP3A; Fatty Acids, Monounsaturated; Female; Glucuronosyltransferase; Gonads; Indans; Liver; Male; Perfume; Steroid 17-alpha-Hydroxylase; Sulfotransferases; Tetrahydronaphthalenes; Water Pollutants, Chemical; Xenobiotics; Xylenes

The concentrations and distributions of six polycyclic musks and two nitro musks in Suzhou Creek, influent/effluent of a sewage treatment plant (STP), and household commodities were investigated and discussed in this study. The levels of 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexa-methylcyclopenta(g)-2-benzopyran (HHCB) and 7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (AHTN) in Suzhou Creek were 3-78 ng g(-1) (dry weight) and 2-31 ng g(-1) (dry weight) in sediments, while 20-93 ng l(-1) and 8-20 ng l(-1) in surface waters. The results indicated a low proportion of wastewater burden in this river. The concentrations of HHCB and AHTN in the effluent of the STP were 5- to 6-fold higher than those in Suzhou Creek. The amounts discharged into the aquatic environment from sewage in Shanghai are 1.26 t (HHCB) and 0.38 t (AHTN) in 2007, and the input into the STPs is estimated to be HHCB 0.2 g y(-1) and AHTN 0.06 g y(-1) per inhabitant, respectively. A broad concentration range of HHCB and AHTN could be observed in household commodities. The distributions are in accordance with the profiles of musks in aquatic environment, with HHCB and AHTN being the major components.

Topics: Benzopyrans; China; Environmental Monitoring; Fatty Acids, Monounsaturated; Geography; Sewage; Tetrahydronaphthalenes; Waste Disposal, Fluid; Water Pollutants, Chemical

Polycyclic musks were measured in surface sediments collected from the Pearl River Delta and Macao coastal region, South China, to investigate contamination from domestic sewage. Three polycyclic musk compounds-4-acetyl-1,1-dimethyl-6-tert-butylindan, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta(g)-2-benzopyran (HHCB), and 7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (AHTN)-were detected in sediment samples. Two polycyclic musks, HHCB and AHTN, were dominant components in sediment, consistent with the use pattern of polycyclic musks by perfume industries in the Pearl River Delta region. The concentrations of total polycyclic musks ranged from 5.76 to 167 microg/kg. Because of the large amount of domestic sewage and industrial wastewater discharged from the city of Guangzhou, the highest concentration of polycyclic musks was found in sediments from the Zhujiang River. The significant positive correlation between the HHCB to AHTN ratios and the concentrations of polycyclic musks suggested that the HHCB to AHTN ratio could be used as a tracer for source discrimination and for the degree of degradation in the environment.

Topics: China; Fatty Acids, Monounsaturated; Geography; Geologic Sediments; Industrial Waste; Perfume; Polycyclic Compounds; Rivers; Seawater; Tetrahydronaphthalenes

Synthetic musk fragrance compounds, such as polycyclic musks (PCMs), are a group of chemicals used extensively as personal care products, and can be found in the environment and the human body. PCMs, such as 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexa-methylcyclopenta-gamma-2-benzopyran (HHCB) and 7-acetyl-1,1,3,4,4,6-hexamethyltetralin (AHTN), are known to have agonistic activities toward human estrogen receptor alpha (hERalpha) and hERbeta, and have antagonistic activity toward the human androgen receptor (hAR), as shown in several reporter gene assays. However, little is known about the interaction of PCMs with the human thyroid hormone receptor (hTR), and the hormonal effects of other PCMs except for HHCB and AHTN. In this study, we focus on the interactions of six PCMs, namely, HHCB, AHTN, 4-acetyl-1,1-dimethyl-6-tert-butyl-indan (ADBI), 6-acetyl-1,1,2,3,3,5-hexamethylindan (AHMI), 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone (DPMI), and 5-acetyl-1,1,2,6-tetramethyl-3-isopropy-lindan (ATII) with hERalpha, hAR, and hTRbeta by in vitro reporter gene assay using Chinese hamster ovary cells. All the samples were found to be agonists toward hERalpha, whereas no agonistic activities of these PCMs for hAR and hTRbeta were observed. No antagonistic activities for hERalpha and hTRbeta were observed at the concentrations tested. However, several PCMs, namely, HHCB, AHTN, ATII, ADBI, and AHMI, showed dose-dependent antagonistic activities for hAR, and the IC50 values of these compounds were estimated to be 1.0 x 10(-7), 1.5 x 10(-7), 1.4 x 10(-7), 9.8 x 10(-6), and 1.4 x 10(-7) M, respectively. The results suggest that these PCMs interact with hERalpha and hAR but have no hormonal effect on hTRbeta. This is the first report on the agonistic and antagonistic activities of ATII, ADBI, AHMI, and DPMI for hERalpha and hAR as determined by in vitro reporter gene assay using stably transfected Chinese hamster ovary cells.

Topics: Animals; Benzopyrans; Biological Assay; CHO Cells; Cosmetics; Cricetinae; Cricetulus; Dose-Response Relationship, Drug; Estrogen Receptor alpha; Fatty Acids, Monounsaturated; Female; Genes, Reporter; Indans; Receptors, Androgen; Receptors, Thyroid Hormone; Tetrahydronaphthalenes

Two important ingredients of personal care products, namely polycyclic musk fragrances and UV filters, can be found in the environment and in humans. In previous studies, several compounds of both classes have been tested for their interaction with the estrogen receptor. Two polycyclic musk fragrances, namely AHTN and HHCB, turned out to be anti-estrogenic both in vitro and in vivo in a transgenic zebrafish assay. Several UV filters have been shown to exert estrogenic effects in vitro and in some in vivo studies. Here, we assessed the interaction of five polycyclic musk compounds and seven UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone (PR) receptor, using sensitive and specific reporter gene cell lines. Four polycyclic musks (AHTN, HHCB, AETT, and AHMI) were found to be antagonists toward the ERbeta, AR and PR. The UV filters that showed estrogenic effects (benzophenone-3, Bp-3; 3-benzylidene camphor, 3-BC; homosalate, HMS; and 4-methylbenzylidene camphor, 4-MBC) were found to be antagonists toward the AR and PR. The ERalpha agonistic UV filter octyl-dimethyl-p-aminobenzoic acid (OD-PABA) did not show activity toward the AR and PR. Octyl methoxy cinnamate (OMC) showed weak ERalpha agonism, but potent PR antagonism. Butyl methoxydibenzoylmethane (B-MDM) only showed weak ERalpha agonism and weak AR antagonism. Most effects were observed at relatively high concentrations (above 1 muM); however, the anti-progestagenic effects of the polycyclic musks AHMI and AHTN were detected at concentrations as low as 0.01 muM. The activity of anti-progestagenic xenobiotics at low concentrations indicates the need to undertake more research to find out about the potential endocrine disrupting effects of these compounds in vivo.

Topics: Benzopyrans; Biological Assay; Cell Line; Dose-Response Relationship, Drug; Drug Interactions; Fatty Acids, Monounsaturated; Genes, Reporter; Humans; Perfume; Receptors, Androgen; Receptors, Estrogen; Receptors, Progesterone; Receptors, Steroid; Sunscreening Agents; Tetrahydronaphthalenes; Toxicity Tests; Transcription, Genetic; Transcriptional Activation

Polycyclic and nitro musks and two fragrances (Acetyl cedrene and Amberonne) have been determined and quantified in influent and effluent waste water, river water and tap water samples from different European countries by closed loop stripping analysis (CLSA) as a method of preconcentration and GC/MS operating in the SIM mode. Limits of detection; precision expressed as repeatability and reproducibility relative standard deviations of the method; matrix effects and the estimation of the uncertainty have been evaluated. All samples contained different musks at ng/l levels being the polycyclic musks Galaxolide and Tonalide and both fragrances, Amberonne and Acetyl cedrene the most abundant. Removal of these main compounds is achieved partially in all waste water treatment plants studied. These results suggest the importance of studying and controlling the presence of these ubiquitous environmental compounds in water systems.

Topics: Benzopyrans; Fatty Acids, Monounsaturated; Gas Chromatography-Mass Spectrometry; Perfume; Reproducibility of Results; Sensitivity and Specificity; Sewage; Tetrahydronaphthalenes; Volatilization; Water Pollutants, Chemical; Water Supply

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Topics: Animals; Benzopyrans; Cell Line; Copepoda; Drosophila melanogaster; Endocrine System; Fatty Acids, Monounsaturated; Female; Indans; Larva; Life Tables; Male; Odorants; Perfume; Population Dynamics; Reproduction; Tetrahydronaphthalenes; Water Pollutants, Chemical; Xylenes

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.

Topics: Adult; Animals; Benzopyrans; Carcinoma, Hepatocellular; Fatty Acids, Monounsaturated; Humans; Indans; Lymphocytes; Micronucleus Tests; Perfume; Rats; Tetrahydronaphthalenes; Tumor Cells, Cultured