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
lactonisation 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 flavoured
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 flavouring a wide range of food
stuffs including baked goods and confectionery.
Una cetona acíclica barata natural del monoterpene (dihydrotagetone) del fórmula (4), aislado del aceite de los sp. de Tagetes, fue oxidada suavemente con permanganato de meta-periodate/potassium en el ácido 2,6-dimethyl-4-oxo-heptanoic del fórmula (3), la reducción de 3 con el hidruro del metal tal como borohydride del sodio o el aluminio 4-hydroxyacid proporcionado hidruro del litio del fórmula (2) que encendido sin el lactonisation experimentado aislamiento en medio ácido equipó dos 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone centrados chiral del fórmula (1) como análogo de la lactona 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone del whisky del fórmula (1a) responsable de alta calidad de la bebida alcohólica (whisky, vino, brandy y escocés), además, 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone condimentado coco del fórmula (1) está también como análogo del coco aldehino (gamma.-nonalactone, F.E.M.A. El No. 2751) del fórmula (1b) que es responsable de condimentar una amplia gama del alimento rellena incluyendo mercancías y la confitería cocidas al horno.
