A natural inexpensive acyclic monoterpene ketone (dihydrotagetone) of
formula (4), isolated from the oil of Tagetes sp., was smoothly oxidized
with meta-periodate/potassium permanganate into
2,6-dimethyl-4-oxo-heptanoic acid of formula (3), the reduction of 3 with
metal hydride such as sodium borohydride or lithium aluminium hydride
provided 4-hydroxyacid of formula (2) which on without isolation undergone
lactonization in acidic medium furnished two chiral centered
5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone of formula (1) as an
analogue of whisky lactone 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone of
formula (1a) responsible for high quality of alcoholic beverage (whisky,
wine, brandy and scotch), in addition, coconut flavored
5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone of formula (1) is also as an
analogue of coconut aldehyde (.gamma.-nonalactone, F.E.M.A. No. 2751) of
formula (1b) which is responsible for flavoring a wide range of food
stuffs including baked goods and confectionery.
Uma cetona acíclica barata natural do monoterpene (dihydrotagetone) da fórmula (4), isolado do óleo de sp. de Tagetes, foi oxidada lisamente com permanganate de meta-periodate/potassium no ácido 2,6-dimethyl-4-oxo-heptanoic da fórmula (3), a redução de 3 com o hydride do metal tal como o borohydride do sodium ou o alumínio 4-hydroxyacid fornecido hydride do lítio da fórmula (2) que sobre sem o lactonization submetido isolação no meio acidic forneceu dois 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone centrados chiral da fórmula (1) como um analogue do lactone 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone do whisky da fórmula (1a) responsável para a qualidade elevada da bebida alcoólica (whisky, vinho, conhaque e scotch), além, 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone flavored coco da fórmula (1) é também como um analogue do coco aldeído (gamma.-nonalactone, F.E.M.A. O no. 2751) da fórmula (1b) que é responsável para flavoring uma escala larga do alimento enche including bens e o confectionery cozidos.
