26 different compounds have been investigated experimentally for their sensitizing capacity in guinea pigs. 19 of these occur in propolis as well as in poplar bud exudates, and 14 of them are also found in balsam of Peru. 4 caffeates and benzyl isoferulate were found to be strong sensitizers. 7 compounds were moderate, and 13 compounds showed only weak sensitizing potency. Methyl cinnamate was negative. Patch tests in 11 propolis-sensitive patients once more revealed 3-methyl-2-butenyl caffeate and phenylethyl caffeate as the major sensitizers. In addition to the 8 compounds already known to occur in propolis as well as in balsam of Peru, we detected 5 further substances that both materials have in common. Among these, benzyl isoferulate is considered a noteworthy sensitizer. Coniferyl benzoate, which was shown to be a moderate sensitizer, is present in fresh samples of balsam of Peru, while in propolis it has been detected only once so far. The flavonoid aglycones occurring in poplar bud exudates, and hence also in propolis, are weak sensitizers which play only a minor role in propolis hypersensitivity.

SummaryNew p-and y-cyclodextrin derivatives, selectively substituted with n-pentyl and methyl groups, e.g. heptakis(2,6-di-Omethyl-3-O-pentyl)-~-cyclodextrin, octakis(2-O-methyl-3,6-di-0-penty1)-y-cyclodextrin, and octakis(2,6-di-O-methyl-3-0-penty1)-y-cyclodextrin, have been prepared from specifically protected intermediates.The new cyclodextrin derivatives exhibit unique enantioselectivity towards important chiral constituents of essential oils. The enantiomers of lavandulol, abisabolol, nerolidol, and other terpenoid alcohols could be resolved and their presence in different essential oils could be proved. Methyl jasmonate and epi-methyl jasmonate could, in addition, be detected in jasmine concrete by two-dimensional gas chromatography. The enantiomers of the macrocyclic ketone muscone have been separated for the first time.

Summary 3 Results and DiscussionModified cyclodextrins interact enantioselectively with a great variety of volatile chiral constituents of essential oils by forming diastereomeric inclusion complexes. Capillary gas chromatography is used for resolving the enantiomers of terpenoid hydrocarbons (camphene, a-pinene, limonene, a-phellandrene), carbonyl compounds (carvone, fenchone, menthone, isomenthone, piperitone, camphor, myrtenal), and alcohols (trifluoroacetylated P-citronellol, myrtenol, trans-pinocarveol, I -octen-3-01, and underivatized linalool). The enantiomeric composition of some of these compounds in a variety of essential oils is investigated.

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