Esters of 1,3,3,-trimethyl-2-oxabicyclo [2.2.2]octan-6-ols: synthesis, odour evaluation and in vitro preliminary toxicity assays.

ABSTRACT

Synopsis The synthesis of a series of alkyl and arylesters of 1,3,3,-trimethyl-2-oxabicyclo[2.2.2]octan-6-ols (2-cineolylols) is described. All cineole esters obtained were tested for their olfactive character; the esters derived from aryl acyl chlorides were odourless, while aliphatic esters showed interesting multipurpose aromas. Some of these compounds exhibited fruity, woody, green, pine oil and violet-like notes and some showed aromas interesting for foodstuffs. In vitro toxicity tests were carried out on the cyclopropyl ester of 2-cineolylols, the most promising of these compounds as a potential perfume ingredient. In this study, cultured mouse fibroblast L-929 and human keratinocyte NCTC 2544 cell lines were used. The results obtained with the evaluation of three different physiological end points showed that the tested compound possess much lower cytotoxicity than sodium dodecylsulphate (SDS) used as positive control.