Musk compounds

Shah et al. (1994) have studied the preparation of a class of compounds called Indans, by cross-dimerization of AMS with amylenes, using an ion-exchange resin and acid-treated clay catalysts (Eqns. (12) and (13)). Indans can be subsequently converted, e.g. by acetylation, into perfumric compounds having mu.sk odour. For example, 1,1,2,3,3-pentamethylindan, the product obtained by cross-dimerization of AMS and wo-amylene (Eqn. (12)), can be reacted with propylene oxide and /7 ra-formaldehyde to give an indan type isochroman musk compound, 6-oxa-l,l,2,3,3,8-hexamethyl-2,3,5,6,7,8-hexahydro-lH-benz(f)-indene, sold as Galaxolide commercially. 

Serum and plasma Serum and plasma samples partially mimic the trend observed in human milk samples. Overall, polycyclic musks can be detected more frequently and at higher concentrations compared to the nitro musk compounds (Table 8). HHCB is by far the most common of the polycyclic musks as production and use of this compound increased at the same time as production and use of nitro musks decreased [168]. However, MX still seems to be a common contaminant in human serum, with a considerably high detection frequency compared to AHTN. A high percentage of the population is still exposed to nitro musk compounds [168], although a moderate decline in MX and a strong decline in MK are observed. 

Luckenbach T, Epel D (2005) Nitromusk and polycyclic musk compounds as long-term inhibitors of cellular xenobiotic defense systems mediated by multidrug transporters. Environ Health Perspect 113 17-24... 

Lignell S, Damerud PO, Aune M, Cnattingius S, Hajslova J, Setkova L, Glynn A (2008) Temporal trends of synthetic musk compounds in mother s milk and associations with personal use of perfumed products. Environ Sci Technol 42 6743-6748... 

Compounds used in the database were obtained from literature reports of chemical structure and odor quality (7-11). In Table 1, a list of the compounds comprising the database is given. The macrocyclic and nitroaromatic musks are of strong, medium, weak, or unspecified odor intensity the nonmusks are odorless or have an odor other than musk. Information about odor quality and intensity is contained in the activity label associated with each compound. It should be emphasized that a musk compound labeled as weak, medium, or strong refers only to the change in its odor threshold, not to any change in its odor quality. Structural classes present in the dataset are shown in Fig. 1. Natural musks, whose sources include both rare animal and plant species, are... 

Kannan K., J.L. Reiner, S.H. Yun, E.E. Perrotta, L. Tao, B. Johnson-Restrepo, and B.D. Rodan (2005). Polycyclic musk compounds in higher trophic level aquatic orgarrism and humans in the United States. Chemosphere 61 693-700. 

Ricking M., J. Schwarzbauer, J. HeUon, A.S. Svenson, and V. Zitko (2003). Polycyclic aromatic musk compounds in sewage treatment plant effluents of Canada and Sweden— first results. Marine Pollution Bulletin 46 410-417. 

The occurrence of musk fragrances (polycyclic musks in particular) in room air samples and house dust from 59 apartments and 74 kindergartens in Berlin in 2000 and 2001 was reported by Fromme et al. (2004a). Results are reviewed in Table 11.2. Musk compounds most often detected in the indoor air and dust were HHCB [1.3.4.6.7.8-hexahydro-4.6.6.7.8.8- hexamethylcyclopenta-(g) 2-benzopyrane, Galaxolide , Abbalide , Pearlide ], AHTN [7-acetyl-1.1.3.4.4.6-hexa-methyl-tetraline, Tonalide , Fixolide ] andmusk ketone (4-t-butyl-2.6-dimethyl-3.5-dinitroacetophenone). 

A modified extraction cell containing a bag-shaped membrane made of LDPE, instead of an FS membrane, was designed to contain the extraction solvent for the extraction of polycyclic musk compounds and pharmaceuticals in wastewater.60 The extraction cell was further developed in terms of membrane design and material. A dense nonporous PP membrane was preferably chosen as a membrane bag in the extraction cell, which was incorporated into a fully automated MASI device that is now commercially available from Gerstel (MUlheim an der Ruhr, Germany). 

Einsle, T., H. Paschke, K. Bruns, S. Schrader, P. Popp, and M. Moeder. 2006. Membrane-assisted liquid-liquid extraction coupled with gas chromatography-mass spectrometry for determination of selected polycyclic musk compounds and drugs in water samples. J. Chromatogr. A 1124 196-204. 

Rudel, H., W. Bohmer, and C. Schroter-Kermani. 2006. Retrospective monitoring of synthetic musk compounds in aquatic biota from German rivers and coastal areas. J. Environ. Monit. 8 812-823. 

B. D. Mookherjee R. A. Wilson, The Chemistry and Fragrance of Natural Musk Compounds. In Fragrance Chemistry The Science of the Sense of Smell E. T. Theimer, Ed. Academic Press London, 1982 pp 433-494. 

Whilst yields are generally low, this is a useful method for preparing large ring compounds, including a number of important musk compounds used in perfumes. 

T. Luckenbach and D. Epel, Nitromusk and Polycyclic Musk Compounds as Long-Term Inhibitors of Cellular Xenobiotic Defense Systems Mediated by Multidrug Transporters, Environmental Health Perspectives, 2005, 113, 1, 17. 

Table 17. Trivial name, CAS number, chemical name, chemical structure, molecular formula, molecular mass, n-octanol/water partition coefficient (log Kow), and bioconcentration factors on a wet weight basis (BCF ) and/or on a lipid basis (BCFl) of Nitro Musk Compounds (NMCs) in mussel and fish, which were detected in an aquatic environment, and/or in human milk and adipose tissue...

Some of these polycyclic musk fragrances were also found in humans [358-360]. Consumption of fish and other food from aquatic ecosystems contaminated with PMFs can not explain the concentration in human. It is assumed that the occurrence of these lipophilic compounds in human adipose tissue or mother s milk is mainly due to dermal sorption from cosmetics and detergents [349-351]. In the future the production and use of polycyclic musk fragrances will still increase and the nitro musk compounds will be replaced by the PMFs. 

The two-phase system has been used for selective oxidation of an alkylborane group in the presence of a double bond.llb Thus the cyclic diene (3) was treated with 1 equiv. of diborane to give the alkylborane (4). which was then oxidized by aqueous chromic acid-diethyl ether to give 8-cyclohexadecene-l-one (5), a musk compound. 

Polycylic aromatic musk compounds in sewage treatment plant effluents of Canada and Sweden ... 

Ricking M, Schwarzbauer J, Hellou J, Svenson A, Zitko V (2002b) Polycyclic aromatic musk compounds in Canada and Sweden - first results. Marine Poll Bull 46, 410-417. 

An interesting case emerges from the comparison of the musk compounds 32 with the nonmusk 33. 

Draisci and co-workers performed interesting research for the extraction of relatively polar analytes such as musk compounds in Italian fresh water fish (60) and corticosteroids in bovine liver (61). For musk components, alumina was utilized in the extraction cell to hinder co-extraction of lipids. The FFR values for these investigations were in the range 0.002 and 0.05, and in no case did they report problems with the presence of fet during the chromatographic analysis. For corticosteroids, a different concept was used, where fat was selectively extracted with pure hexane, followed by elution of the analytes in a second step. 

Perfume The musk used in perfumes and colognes contains many chemical compounds, including large cycloalkanes. Research and write a short report about the sources used for natural and synthetic musk compounds in these consumer products. 

Most of fragrance determinations in indoor environments have been focused on synthetic musks, and have been performed on dust (Table 5). Synthetic musk fragrances have been extracted from house dust by PLE (Gevao et al. 2006 Rudel et al. 2003). Fromme et al. (2004) carried out the PLE extraction of both polycyclic and nitromusk in indoor dust with n-hexane/diethyl ether (19 1) and further determination by GC/MS operating in the El mode with SIM. Recently, Peck et al. (2007) reported the extraction of musk compounds from the indoor dust standard reference material SRM 2585 with dichloromethane at 100°C and 2000 psi. After clean-up on an alumina SPE cartridge, a GPC column and volume concentration, recoveries in the range 73-90% were obtained. 

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