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Franke S, Meyer C, Heinzel N, et al. Enantiomeric composition of the polycyclic musks HHCB and AHTN in different aquatic species. Chirality. 1999;11(10):795-801doi: 10.1002/(SICI)1520-636X(1999)11:10<795::AID-CHIR10>3.0.CO;2-S.
Franke, S., Meyer, C., Heinzel, N., Gatermann, R., Huhnerfuss, H., Rimkus, G., Konig, W. A., & Francke, W. (1999). Enantiomeric composition of the polycyclic musks HHCB and AHTN in different aquatic species. Chirality, 11(10), 795-801. https://doi.org/10.1002/(SICI)1520-636X(1999)11:10<795::AID-CHIR10>3.0.CO;2-S
Franke, et al. "Enantiomeric composition of the polycyclic musks HHCB and AHTN in different aquatic species." Chirality vol. 11,10 (1999): 795-801. doi: https://doi.org/10.1002/(SICI)1520-636X(1999)11:10<795::AID-CHIR10>3.0.CO;2-S
Franke S, Meyer C, Heinzel N, Gatermann R, Huhnerfuss H, Rimkus G, Konig WA, Francke W. Enantiomeric composition of the polycyclic musks HHCB and AHTN in different aquatic species. Chirality. 1999;11(10):795-801. doi: 10.1002/(SICI)1520-636X(1999)11:10<795::AID-CHIR10>3.0.CO;2-S. PMID: 10561711.
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Chirality. 1999;11(10):795-801. doi: 10.1002/(SICI)1520-636X(1999)11:10<795::AID-CHIR10>3.0.CO;2-S.

Enantiomeric composition of the polycyclic musks HHCB and AHTN in different aquatic species.

Chirality

Franke, Meyer, Heinzel, Gatermann, Huhnerfuss, Rimkus, Konig, Francke

Affiliations

  1. Institut fur Organische Chemie, Universitat Hamburg, Hamburg, Germany.

PMID: 10561711 DOI: 10.1002/(SICI)1520-636X(1999)11:10<795::AID-CHIR10>3.0.CO;2-S

Abstract

Synthetic polycyclic musk fragrances are mainly represented by the compounds HHCB (Galaxolide(TM)) and AHTN (Tonalide(TM)). Because of their volume of use and their bioaccumulation potential, there is concern with respect to their environmental safety. HHCB and AHTN are chiral compounds, and gas chromatography using modified cyclodextrins as chiral stationary phases coupled to high-resolution mass spectrometry enabled enantioselective analysis even under unfavorable matrix conditions. The gas chromatographic elution order of (4S,7RS)- and (4R,7RS)-HHCB was assigned using synthetic (4S, 7RS)-HHCB. Fish and mussels reared in a pond associated with a municipal waste water treatment plant and semipermeable membrane devices exposed in the pond were analyzed for HHCB and AHTN. The highest lipid concentrations of HHCB and AHTN were observed in mussels (Dreissena polymorpha), tench (Tinca tinca), and crucian carp (Carassius carassius). Pronounced deviations in enantiomeric composition from racemic HHCB were observed in crucian carp and from racemic AHTN in tench. Correlations between lipid levels, enrichment, and enantioselective biotransformation of HHCB or AHTN were not seen. Selective biotransformation depended on both the compound and the species involved. The present study gives the first account of the enantiomeric composition of HHCB and AHTN in aquatic species. The lactone, 1,3,4,6,7,8-hexahydro-4,6,6,7,8, 8-hexamethylcyclopenta[g]-2-benzopyran-1-one, an oxidation product of HHCB, has been identified for the first time in environmental samples. Copyright 1999 Wiley-Liss, Inc.

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