Viewpoint . Synthetic musks in environmental samples: indicator compounds with relevant properties for environmental monitoring

Abstract

Synthetic musks (nitro and polycyclic musks) are a group of chemicals offering a wide range of important properties for environmental monitoring programs. They are produced as odorous chemicals and added to a wide variety of perfumes, toiletry products and other household products. As such, they are directly applied in cosmetic products or in washed textiles to the human body in considerable concentrations and accumulate owing to dermal resorption. In addition, synthetic musks also enter the environment via waste water treatment. Several polycyclic musks are chiral. By using chiral gas chromatographic methods, it is possible to determine the enantiomeric ratio and assess their bioavailability. Although an comprehensive quality assurance program must be followed during the analysis of synthetic musks in environmental samples, the determination of these compounds is not very demanding and can be carried out by a standard analytical laboratory specialising in trace analysis of organic pollutants. Owing to the pheromone-like behavior of some synthetic musks, the induction of receptors in olfactory systems should be investigated. For HHCB (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[ g]-2-benzopyran, e.g., Galaxolide® ), three-dimensional structural similarities with androstenone (5α-androst-16-en-3-one), a mammalian steroid pheromone, were found, which support the hypothesis of HHCB as an artificial pheromone. Owing to their environmental abundance, their relation to human activities and their potential for pheromone-like environmental behavior, synthetic musks are especially valuable as future indicator chemicals for environmental monitoring.

References

1. A. Baur, Ber. Dtsch. Chem. Ges., 1891, 24, 2832.
2. R. Gatermann, J. Hellou, H. Hühnerfuss, G. G. Rimkus and V. Zitko, Chemosphere, 1999, 38, 3431.
3. G. G. Rimkus, Toxicol. Lett., in the press.
4. T. Yamagishi, T. Myazaki, S. Horii and S. Kaneko, Arch. Environ. Contam. Toxicol., 1983, 12, 83.
5. B. Liebl and S. Ehrensdorfer, Chemosphere, 1993, 27, 2253.
6. G. G. Rimkus and M. Wolf, Chemosphere, 1995, 30, 641.
7. G. G. Rimkus and H. Brunn, Ernährungs-Umschau, 1996, 43, 442.
8. H. Brunn and G. G. Rimkus, Ernährungs-Umschau, 1996, 44, 4.
9. R. Kallenborn, R. Gatermann, S. Planting, G. G. Rimkus, M. Lund, M. Schlabach and I. C. Burkow, J. Chromatogr., in the press.
10. E. J. van de Plassche and F. Balk, RIVM Report No. 601503008, RIVM, Bilthoven, 1997.
11. G. G. Rimkus, in Fragrances: Beneficial and Adverse Effects, ed. P. J. Frosch, J. D. Johansen and I. R. White, Springer, Berlin, 1998, p. 136.
12. G. G. Rimkus, W. Butte and H. J. Geyer, Chemosphere, 1997, 35, 1497.
13. K. Kokot-Helbling, P. Schmitt and C. Schlatter, Mitt. Geb. Lebensmittelunters Hyg., 1995, 86, 1.
14. D. E. Rickert, B. E. Butterworth and J. A. Popp, CRC Crit. Rev. T oxicol., 1984, 13, 217.
15. L. D. Lehman-McKeeman, D. R. Johnson and D. Caudill, Toxicol. Appl. Pharmacol., 1997, 142, 169.
16. R. Gatermann, H. Hühnerfuss, G. Rimkus, A. Attar and A. Kettrup, Chemosphere, 1998, 36, 2535.
17. L. D. Lehman-McKeeman, D. R. Johnson, D. Caudill and S. B. Stuard, Drug Metab. Dispos., 1997, 25, 384.
18. A. N. Gilbert, Perfumer Flavorist, 1992, 17, 17.
19. G. Frater, U. Müller, J. A. Bajgrowicz and M. Petrzilka, in Proceedings of the 13th International Congress of Flavours, Fragrances and Essential Oils, Istanbul, Turkey, October 15–19, 1995, ed. K. H. C. Baser, 1995, p. 151.
20. A. N. Gilbert and C. J. Wysocki, Nat. Geogr., 1987, 172, 514.
21. A. Baydar, M. Petrzilka and M. P. Schott, Chem. Senses, 1993, 18, 661.
22. W. Vetter and V. Schurig, J. Chromatogr., 1997, 774, 143.
23. R. Gatermann, S. Biselli, M. Hecker, G. G. Rimkus, L. Karbe, R. Kallenborn, W. A. König and H. Hühnerfuss, Environ. Sci. Technol., submitted for publication.
24. C. H. Walker, S. P. Hopkin, R. M. Sibly and D. B. Peakall, Principles of Ecotoxicology, Taylor and Francis, London, 1997.
25. C. Desbrow, E. J. Routledge, G. C. Brightly, J. P. Sumpter and M. Waldock, Environ. Sci. T echnol., 1998, 32, 1549.