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Baker’s yeast‐mediated synthesis of endo ‐2‐cineolylol, a starting compound for potential cosmetic odourants[Note 2. Presented in part as a poster at 20th IFSCC ...][Note 3. Dedicated to the memory of Professor Pietro Schenone ...]
Author(s) -
E Mariani,
Martina Bruno,
Carla Villa,
C Neuhoff
Publication year - 2000
Publication title -
international journal of cosmetic science
Language(s) - French
Resource type - Journals
SCImago Journal Rank - 0.532
H-Index - 62
eISSN - 1468-2494
pISSN - 0142-5463
DOI - 10.1046/j.1467-2494.2000.00029.x
Subject(s) - chemistry , stereochemistry , medicinal chemistry
Synopsis Baker’s yeast‐mediated reduction of (+)‐1,3,3‐trimethyl‐2‐oxabicyclo[2,2,2]octan‐6‐one yields the corresponding 1,3,3‐trimethyl‐2‐oxabicyclo[2,2,2]octan‐6‐ol as endo configuration in optically pure form. To study the reaction behaviour we have developed a RP‐HPLC method. The synthesis and the olfactive character of some esters obtained from the endo ‐2‐cineolylol are reported. A comparative odour evaluation between these esters and the corresponding compounds synthesized from the endo‐exo alcohol mixture was performed. Résumé La réduction de (+)‐1,3,3‐triméthyl‐2‐oxabicyclo[2,2,2]octan‐6‐one par la lévure conduit au 1,3,3‐triméthyl [2,2,2]octan‐6‐ol correspondant, de configuration endo avec une forme optique pure. On a développé une méthode RP‐HPLC pour enregistrer le comportement de la réaction. La synthèse et le caractère olfactif des esters obtenus de cet alcool sont rapportés.. On a comparé l’évaluation de l’odeur de ces composés avec celle des composés correspondants, dérivés du mélange endo‐eso des alcools.