3,3,5-Trimethylcyclohexanols and derived esters: Green synthetic procedures, odour evaluation and in vitro skin cytotoxicity assays

R. Gambaro, C. Villa, S. Baldassari, E. Mariani, A. Parodi, A. M. Bassi

Research output: Contribution to journalArticle

Abstract

The alcohols 3,3,5-trimethylcyclohexanols (cis, trans epimers, cosmetic fragrance) and some derived esters, potential and well-known actives in the cosmetic field, such as Homosalate, were synthesized using fast solvent-free methodologies with the aim of renewing and simplifying the conventional procedures. The alcohols were prepared by reduction of 3,3,5- trimethylcyclohexanone (dihydroisophorone) with sodium borohydride/alumina in solid state. The esters from propanoic, butanoic, octanoic, 10-undecenoic, cyclopropanecarboxylic, mandelic and salicylic acids were synthesized with microwave-mediated solvent-free procedures under acidic and basic catalysis. Several experiments were carried out to study advantages and limits of the selected methodologies and the results are reported. Microwave irradiation was carried out using a scientific monomode reactor. In order to evaluate the cosmetic interest of the studied compounds, the sweet-scented substances were submitted to an odour evaluation test; the most promising fragrances and the ester from 10-undecenoic acid, as an example of lipophilic derivatives, were tested to assess their in vitro skin toxicity.

Original languageEnglish
Pages (from-to)439-446
Number of pages8
JournalInternational Journal of Cosmetic Science
Volume28
Issue number6
DOIs
Publication statusPublished - Dec 2006

Keywords

  • 3,3,5-trimethylcyclohexanols and derived esters
  • Green chemistry
  • In vitro cytotoxicity assays
  • Microwave-mediated esterification
  • Solvent-free reduction

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Dermatology

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