3,3,5-Trimethylcyclohexanols and derived esters: green synthetic procedures, odour evaluation and in vitro skin cytotoxicity assays1
| Autor: | Sara Baldassari, Alessandro Parodi, Carla Villa, Emilia Mariani, A. M. Bassi, R. Gambaro |
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| Rok vydání: | 2006 |
| Předmět: |
Green chemistry
Aging Prima materia Stereochemistry Pharmaceutical Science Dermatology Chemical synthesis Catalysis Homosalate Sodium borohydride chemistry.chemical_compound Colloid and Surface Chemistry Odor chemistry Chemistry (miscellaneous) Drug Discovery medicine Organic chemistry Epimer medicine.drug |
| Zdroj: | International Journal of Cosmetic Science. 28:439-446 |
| ISSN: | 0142-5463 |
| DOI: | 10.1111/j.1467-2494.2006.00343.x |
| Popis: | 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. Resume |
| Databáze: | OpenAIRE |
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