Zur Diastereoisomerie natürlicher und synthetischer -Bisabolole

Author(s): Nonnenmache, G., Isaac, O.

Journal/Book: Z Naturforsch. 1981; 36b: 114-118.

Abstract: The stereochemistry of ?-bisabolol is discussed. The chiralities of the different ?-bisabolols from Myoporum crassifolium, Popalus balsamifera and Vanillosmopsis erythropappa are deduced from the absolute configuration of natural bisabolol from chamomile, which has to be considered as being (1' S, 2 S)-configurated according to most recent investigations.Based an this assumption, (1' S, 2 R)-configuration has to be ascribed to (-)-?-bisabolol from Myoporum crassifolium, whereas (1' R, 2 R)- resp. (1' S, 2 S)-structure is present in (+)-?-bisabolol from Popalus balsamifera and (-)-?-bisabolol from Vanillosmopsis erythropappa being therefore enantiomeric to the latter. Consequently, the (-)-?-bisabolols from Matricaria chamomilla and Vanillosmopsis erythropappa turn out to be identical in all respects.Synthetic ?-bisabolols, however, featuring approximately equal amounts of all the four, possible stereoisomers, differ not only optically bat also in their stereochemical uniformity from natural ?-bisabolols.By means of NMR spectrometric methods the identity of the native active agent can be established in chamomile specialities; as a consequence possible admixtures of sythetic racemates of ?-bisabolol thus can be identified and quantified.

Keyword(s): Bisabolol

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