Polycyclic musks

Musks are pleasant smelling fragrances found in various personal and home care products. Since the 1950s, the usage of natural musks has declined due to the relatively easy and inexpensive production of their synthetic counterparts. There are three major types of synthetic musks, nitro musks, polycyclic musks, and macro... 

Personal care products Nitro musks, polycyclic musk, chlorophene GC-MS (El and NCI)... 

On the other hand, the term musk also refers to other compounds, with totally different chemical structure but possessing musk-Uke odor properties. These are commonly named synthetic musks and appeared as a response to ecrniomical and ethical motives. Artificial musks have been generally divided in three subgroups nitro musks, polycyclic musks, and macrocycUc musks. 

The cross-dimerization reaction is very commonly employed for the manufacture of intermediates for synthetic musks, which have become an important class of perfumery chemicals. Synthetic musks have been the target of extensive research over the years due to a conservation order placed on the musk deer. Nitro musks are being steadily replaced by non-nitro polycyclic musks becau.se of technical drawbacks and health aspects of the former, which are explosive, sensitive, and virtually nonbiodegradable. Non-nitro musks, on the other hand exhibit better stability to light and alkali, and more nearly duplicate the odour of the macrocyclic musks occurring in nature. Indian musk odorants are easily soluble in alcohol and perfume compositions. They have the added advantage of non-discoloration in soap and domestic products. In view of the low price, their future in the perfume industry appears very promising. 

Keywords Fragrance materials Wastewater treatment Polycyclic musks Nitromusks Abbreviations... 

The nitromusks (NMs) (shown in Fig. 2) and the polycyclic musks (PCMs) (shown in Fig. 3) have been studied in wastewater treatment by a variety of research groups because they have been detected in the aquatic environment (see for example [7-10]), indicating that they escape wastewater treatment to some degree. The FMs shown in Fig. 1 were studied in wastewater treatment by Simonich et al. [2,11 ] because of their relatively large volumes and wide range of physical-chemical properties and biodegradabihty (see below). 

Gatermann, R. Siselli, S. Huhnerfuss, H. Rimkus, G. G. Hecker, M. Karbe, L. 2002, Synthetic musks in the environment. Part 1 Species-dependent bioaccumulation of polycyclic and nitro musk fragrances in freshwater fish and mussels. Arch. Environ. Con. Tox. 42 437 46. 

Franke, S. Meyer, C. Heinzel, N. Gaterman, R. Huehnerfuss, H. Rimkus, G. Koenig, W.A. Francke, W. 1999, Enantiomeric composition of the polycyclic musks HHCB and AHTN in different aquatic species. Chirality 11 795-801. 

Hiihnerfuss, H. BiselU, S. Gaterman, R. 2004, Enantioselective Analysis of Polycyclic Musks as a Versatile Tool for the Understanding of Environmental Processes. The Handbook of Environmental Chemistry, Springer-Verlag Heidelberg, Germany Vol. 3X, pp. 213-231. 

Homecare Products got their suppliers to remove a polycyclic musk and diethyl phthalates from their products after talking to Greenpeace in August 2001. Their suppliers subsequently informed them that the two substances added no benefit to the cleaning properties of the product. 

Puma, a sport-lifestyle brand, committed to eliminating the OSPAR+ chemicals from both its sports shoes and perfumes with immediate effect, across their whole product range. Results of perfume testing commissioned by Greenpeace revealed that Puma s Jamaica Man and Puma Woman had some of the lowest levels of nitromusks and polycyclic musks of all of the samples analysed. ... 

Chlorine DBPs of the polycyclic musks 6-acetyl-1,1,2,4,4,7-hexamethy 1-tetraline (AHTN) and 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-y-2-benzopyran (HHCB), which are widely used fragrances in cosmetics, daily care products, and cleaning products for household and industry, were investigated by Kuhlich et al. [123]. This study evidenced chlorination of HHCB as a potential new source of HHCB-lactone in the environment, other than biological transformation. 

Kuhlich P, Gostl R, Teichert P, Piechotta C, Nehls I (2011) Transformation of polycyclic musks AHTN and HHCB upon disinfection with hypochlorite two new chlorinated disinfection by-products (CDBP) of AHTN and a possible source for HHCB-lactone. Anal Bioanal Chem 399 3579-3588... 

Abstract We have reviewed the human exposure to selected emerging organic contaminants, such new brominated flame retardants, organophosphate flame retardants, phthalate substitutes, triclosan, synthetic musks, bisphenol-A, perchlorate, and polycyclic siloxanes. Levels of these emerging contaminants in matrices relevant for human exposure (air, dust, food, water, etc.) and in human matrices (blood, urine, or tissues) have been reviewed, together with some of the relevant health effects reported recently. 

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. 

Hutter HP, Wallner P, Moshaminer H, Haiti W, Sattelberger R, Lorbeer G, Kundi M (2005) Blood concentrations of polycyclic musks in healthy young adults. Chemosphere 59 487-492... 

Rimkus GG (1999) Polycyclic musk fragrances in the aquatic environment. Toxicol Lett 111 37-56... 

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... 

Reiner JL, Kaiman K (2006) A survey of polycyclic musks in selected household commodities from the United States. Chemosphere 62 867-873... 

Heberer T (2002) Occurrence, fate, and assessment of polycyclic musk residues in the aquatic environment of urban aieas-a review. Acta Hydrochem Hydrobiol 30 227-243... 

Buerge, I. J. Buser, H.-R. Muller, M. D. Poiger, T. Behavior of the Polycyclic Musks HHCB and AHTN in Lakes, Two Potential Anthropogenic Markers for Domestic Wastewater in Surface Waters. Environ. Sci. Technol. 2003, 37, 5636-5644. 

Polycyclic musk fragrances (PMFs) are a major class of compounds. More than 5000 tons of polycyclic musks are synthesized worldwide annually (Kannan et al., 2005). HHCB and AHTN are two of the most frequendy used PMFs worldwide. They are semi-volatile compounds with a log of 5.4—6.3 (Ricking et al., 2003). They am poorly... 

As with any analytical determination procedure, both quality assurance and quality control issues have to be built into the detection of PPCPs in the environment. For example, analysis of polycyclic musks (PCM) can be easily skewed during analysis as the compound might be present in laboratory soaps and creams, thus coating laboratory glassware used for the analysis. Therefore, programs that are designed to research... 

Balk F. and R.A. Ford (1999). Environmental risk assessment for the polycyclic musks AHTN and HHCB in the EU I. Fate and exposure assessment. Toxicology Letters 111 57-79. 

Berset J.D., T. Kupper, R. Etter, and J. Tarradellas (2004). Considerations about the enantio-selective transformation of polycyclic musks in wastewater and sewage sludge and analysis of their fate in a sequencing batch reactor plant. Chemosphere 57 987-996. 

Gatermann R., S. Biselli, H. Huhnerfuss, G.G. Rimkus, M. Hecker, and L. Karbe (2002). Synthetic musks in the environment. Part 1 Species-dependent hioaccumulation of polycyclic and nitro musk fragrances in fi eshwater flsh and mussels. Archives of Environmental Contamination and Toxicology 42 437-446. 

HERA (2004). Human and environmental risk assessment on ingredients of household cleaning products. Polycyclic musks. Available at http //www.heraproject.com/files/28-E-36551E10F8EF-E807-E4199B9BB0076A9F.pdf. 

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. 

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