musk and musk-xylene

The polycyclic musk fragrances, mainly 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta(g)-2-ben zopyrane (HHCB) and 7-acetyl-1,1,3,4,4,6-hexamethyltetrahydronaphthalene (AHTN) are synthetic musk fragrances which are used in almost all scented consumer products, such as perfumes, cosmetics and laundry detergents. Concerning their chemical structures the polycyclic musks are indane and tetraline derivatives highly substituted mainly by methyl groups. Their production has been increased continuously during the last years with a world-wide production volume today of about 6000 t/year. After their application in private households they are dumped via the sewage treatment plants into the aquatic environment. In this review the analysis of polycyclic musk compounds in environmental samples is shortly presented and all published data of polycyclic musk compounds in water, sediment, suspended particulate matter (SPM), sewage sludge, and biota are summarized and discussed. The highest HHCB and AHTN concentrations were analysed in water (maximum concentrations: 6 microg HHCB/l, 4.4 microg AHTN/1) and sludge (maximum concentrations: 63 mg HHCB/kg dry matter, 34 mg AHTN/kg dry matter) from sewage plants, and in fish (maximum concentrations: 159 mg HHCB/kg lipid, 58 mg AHTN/kg lipid) from sewage ponds. In all other samples from different aquatic ecosystems these chemicals were unequivocally detected in varying concentrations dependent on the distance to sewage treatment plants. Even in marine water samples from the German Bight HHCB and AHTN could be quantified at the lower ng/l level. Very often HHCB and AHTN formed the major organic contaminants, in all samples their concentrations exceeded those of musk xylene and musk ketone. Also several by-products and impurities of the commercial polycyclic musks were analysed in river and waste water samples in not negligible amounts. The apparently ubiquitous distribution of polycyclic musks in the aquatic environment demonstrates the persistence and lipophilicity of these pollutants. The high log K(ow) values of HHCB and AHTN (5.7-5.9) do not directly correlate with their relatively low bioconcentration factors (BCFs) derived from fish experiments, this discrepancy may be explained by a particular metabolism in fish. There are indications of a possible species dependent metabolisation. For a general risk assessment of this new group of environmental pollutants besides the missing toxicological data, further studies on

Topics: Animals; Benzopyrans; Fatty Acids, Monounsaturated; Fishes; Geologic Sediments; Naphthalenes; Perfume; Sewage; Water Pollutants, Chemical; Xylenes

Understanding olfaction process at a microscopic or molecular level needs more elucidation of the multiple stages involved in the olfaction mechanism. A worth full elucidation and a better understanding of this molecular mechanism, a necessary preamble should be achieved. The content of this work is a preamble for that. A study of the mouse and human olfactory receptors activation in response to two nitro musks stimuli, which are the musk xylol and the musk ketone, are considered here, first, for their wide expanded use in perfumery, but also to show some particular aspects of this process in the case of these two stimuli, which could help to deduce more details and more general aspects in the global olfactory mechanism. A statistical physics modeling using the monolayer model with two independent types of receptor binding sites of the response of the mouse olfactory receptor MOR215-1 and the human olfactory receptor OR5AN1, which are identified as specifically responding to musk compounds, is used to characterize the interaction between the two nitro musk molecules, the mouse and the human olfactory receptors and to determine the olfactory band of these two odorants through the determination of the molar adsorption energies and the adsorption energy distributions. The physico-chemical model parameters can be used for the steric characterization via the calculation of the receptor site size distributions. The docking computation between these two nitro musks and the human olfactory receptor OR5AN1 is performed demonstrating a large similarity in receptor-ligand detection process. Thus, docking finding results prove that the calculated binding affinities were belonging to the spectrum of adsorption energies.

Topics: Adsorption; Animals; Fatty Acids, Monounsaturated; Humans; Mice; Models, Chemical; Molecular Docking Simulation; Nitro Compounds; Odorants; Physics; Receptor Protein-Tyrosine Kinases; Receptors, Cholinergic; Receptors, Odorant; Smell; Xylenes

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

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

Musk xylene (MX) is a widely used synthetic nitro musk. Although the persistence and bioaccumulation of the synthetic musks are of concern since the nineteenth century, knowledge concerning the toxicity and environmental risks, especially the carcinogenicity is still limited. In the present study, the normal human hepatic cell line L02 was used to investigate the long-term carcinogenicity of MX. L02 cells were exposed to MX with different concentrations (10, 100, and 1000 μg/L) for 24 h, then with conventional culture. After MX exposure for 24 h, some irregular fusiform, protuberances and multinucleated cells were observed. Indefinite cell proliferation, ability of anchorage-independent proliferation and increase of migration and invision were also observed in subsequent experiments, which suggested the positive effects of MX on cell malignant transformation in vitro. Moreover, the up-regulated protein expression of some oncogenes (C-myc and PCNA) in each time points furthermore supported this conclusion. Meanwhile, decreased protein expression level of TGF-β and the downstream proteins, SMAD4 coupled with P15 were observed in MX-treated cells. In addition, after culturing for 20 passages, the proportion of cells in the G0/G1 phase was decreased. These results demonstrated that the TGF-β signaling pathway regulated indefinite cell proliferation might be responsible for the oncogenesis of MX.

Topics: Carcinogens; Cell Line; Fatty Acids, Monounsaturated; Humans; Liver; Transforming Growth Factor beta; 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

Synthetic musks are organic compounds used as fragrance and fixative additives in several personal care products. Until now, little is known about their occurrence and distribution in these household commodities. However, this information is essential to perform a human dermal exposure assessment. Therefore, this study gives an overview on the levels of 12 synthetic musks in 140 personal care products from 7 different categories (body and hair wash, toilet soaps, shaving products, dentifrice products, deodorants/antiperspirants, moisturizers and perfumes). They were analysed by QuEChERS extraction followed by gas chromatography-mass spectrometry. Detection limits were found between 0.01ngg(-1) (galaxolide) and 5.00ngg(-1) (musk xylene). Higher average concentrations of total synthetic musks were detected in perfumes (5245.05μgg(-1)) and shampoos (487.67μgg(-1)) for adults. Galaxolide, exaltolide and cashmeran were the most detected compounds. Combining these results with the daily usage amounts, an average daily dermal exposure of 75.69μgkgbw(-1)day(-1) for adults and 15.54μgkgbw(-1)day(-1) for babies/children was achieved. The main contributors for adult and babies/children dermal exposure were perfumes and lotions, respectively. About 40% of the adult daily dermal exposure is related to exaltolide, 30% galaxolide, and 15% tonalide, while for babies/children 96% occurs due to exaltolide. An estimate of the amount of musks discharged "down-the-drain" into the wastewater treatment systems through the use of toiletries was also performed. An average emission per capita of 6.7mgday(-1) was determined and galaxolide and exaltolide were the predominant musks in the effluents.

Topics: Adult; Benzopyrans; Environmental Exposure; Fatty Acids, Monounsaturated; Gas Chromatography-Mass Spectrometry; Humans; Indans; Infant; Lactones; Limit of Detection; Odorants; Perfume; Skin; Soaps; Wastewater; Water Pollutants, Chemical; Xylenes

To investigate the occurrence of 13 kinds of synthetic musk and triclosan in breast milk samples collected from Beijing, and to estimate the exposure of breastfed infants.. Target compounds in 65 milk samples collected from 4 districts of Beijing in 2004 were analyzed by means of gas chromatography - tandem mass spectrometry (GC - MS/MS) and quantified by internal standards. The exposure of infants was analyzed statistically by SPSS software.. HHCB, AHTN, OTNE, MT and Triclosan were detected in milk samples in the range of 0.6 - 174.1 ng/g lipid, with some difference in 4 districts. It is estimated that the intake of synthetic musks and triclosan for each infant from breast milk would be 13.5 - 3917 ng/d.. Commonly used synthetic musks and tricloson were generally detected in breast milk. Further study should be focused on monitoring and tracing the possible source of pollution.

Topics: Adult; Breast Feeding; Environmental Exposure; Environmental Pollutants; Fatty Acids, Monounsaturated; Female; Gas Chromatography-Mass Spectrometry; Humans; Infant; Milk, Human; Perfume; Tandem Mass Spectrometry; Triclosan; Xylenes

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

Synthetic musk fragrances have been measured in water, air, sediments, sewage sludge, and biota worldwide. As the study of the environmental fate and impacts of these compounds progresses, the need for Standard Reference Materials (SRMs) for these compounds to facilitate analytical method improvement and interlaboratory comparisons becomes increasingly important. The National Institute of Standards and Technology (NIST) issues environmental matrix SRMs with certified concentrations for a variety of persistent organic pollutants including polycyclic aromatic hydrocarbons (PAHs), chlorinated pesticides, and polychlorinated biphenyl congeners (PCBs). Until now synthetic musk fragrance concentrations have not been reported in NIST SRMs. The objective of this study was to provide reference values for several commonly detected synthetic musk fragrances in several NIST natural matrix SRMs. In this study five polycyclic musk fragrances [HHCB (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-gamma-2-benzopyran), AHTN (7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene), ADBI (4-acetyl-1,1-dimethyl-6-tert-butylindane), AHMI (6-acetyl-1,1,2,3,3,5-hexamethylindane), and ATII (5-acetyl-1,1,2,6-tetramethyl-3-isopropylindane] and two nitro musk fragrances [musk xylene (1-tert-butyl-3,5-dimethyl-2,4,6-trinitrobenzene) and musk ketone (4-tert-butyl-3,5-dinitro-2,6-dimethylacetophenone)] were measured in selected environmental SRMs. Gas chromatography-electron impact mass spectrometry (GC/EI-MS) was used for all analyses. HHCB was the most frequently detected synthetic musk fragrance and was detected in SRM 2585 Organic Contaminants in House Dust, SRM 2781 Domestic Sludge, SRM 1974b Organics in Mussel Tissue (Mytilus edulis), and SRM 1947 Lake Michigan Fish Tissue. It was not detected in SRM 1946 Lake Superior Fish Tissue or SRM 1945 Organics in Whale Blubber. Concentrations of HHCB in these SRMs ranged from 1.12 ng/g in SRM 1947 to 92,901 ng/g in SRM 2781. All of the polycyclic musk fragrances were detected in SRM 2781 and all of the target compounds were detected in SRM 2585.

Topics: Animals; Bivalvia; Chemistry Techniques, Analytical; Dust; Environmental Monitoring; Environmental Pollutants; Fatty Acids, Monounsaturated; Gas Chromatography-Mass Spectrometry; Models, Chemical; Mytilus; Organic Chemicals; Reference Standards; Reproducibility of Results; Xylenes