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Esters of 1,3,3,‐trimethyl‐2‐oxabicyclo [2.2.2]octan‐6‐ols: synthesis, odour evaluation and in vitro preliminary toxicity assays
Author(s) -
MARIANI E.,
NEUHOFF C.,
BARGAGNA A.,
LONGOBARDI M.,
FERRO M.,
GELARDI A.
Publication year - 1995
Publication title -
international journal of cosmetic science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.532
H-Index - 62
eISSN - 1468-2494
pISSN - 0142-5463
DOI - 10.1111/j.1467-2494.1995.tb00122.x
Subject(s) - chemistry , toxicity , in vitro , cytotoxicity , positive control , sodium , alkyl , stereochemistry , organic chemistry , traditional medicine , biochemistry , medicine
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