title: Semipreparative-scale gas-chromatographic separation of filbertone enantiomers.
abstract: The enantioselectivity of heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl-beta-CD) toward racemic filbertone (E-5-methyl-hep-2-en-4-one) was studied by performing the chiral separation on a capillary column, a thick-film wide-bore column and a semipreparative column. The semipreparative enantioseparation of filbertone was achieved at 80 degrees C by using a packed column providing (R)- and (S)-enantiomers of filbertone with ee 90 and 96%, respectively. The isolated enantiomers (approximately 250 microg each, ee = 90-96%) may be used for studies on the relationship of chirality and biological activity by olfactory screening and toxicological studies.
authors.affiliation: Instituto de Fermentaciones Industriales, Consejo Superior Investigaciones Cientificas (CSIC), c/ Juan de la Cierva 3, Madrid, Spain. gblanch@ifi.csic.es
authors.forename: Gracia Patricia
authors.initials: GP
authors.lastname: Blanch
authors.forename: Marisa L
authors.initials: ML
authors.lastname: Ruiz del Castillo
mesh_terms: D002849:Chromatography, Gas / Q000379:methods*; D006536:Heptanes / Q000032:analysis / Q000302:isolation & purification; D010938:Plant Oils / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006536:Heptanes; D010938:Plant Oils; C475234:5-methylhept-2-en-4-one