Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
2001-05-23
2003-07-15
Padmanabhan, Sreeni (Department: 1617)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C514S183000, C514S359000
Reexamination Certificate
active
06592884
ABSTRACT:
FIELD OF THE INVENTION
The present invention concerns the use of alpha-keto enamine derivatives as ingredients.
BACKGROUND OF THE INVENTION
The Maillard reaction of L-proline with reducing monosaccharides has been extensively studied during the last two decades in order to gain insights into the formation of volatiles during thermal processing of cereal products (Tressl et al.,
J. Agric. Food Chem.
1985a, 33, 919-923; Tressl et al.
J. Agric. Food Chem.
1985b, 33, 924-928; Tressl et al.
J. Agric. Food Chem.
1985c, 33, 1132-1137; Helak et al.
J. Agric. Food Chem.
1989a, 37, 400-404; Helak et al.
J. Agric. Food Chem.
1989b, 37, 405-410; Huyghues-Despointes et al.
J. Agric. Food Chem.
1994, 42, 2519-2524).
By application of the GC/olfactometry techniques such as Charm analysis (Roberts, D. D., Acree, T. In
Thermally Generated Flavors;
Parliment T. H., Morello M. J., McGorrin R., Eds.; ACS, Washington DC, 1994, 71-79) or aroma extract dilution analysis (AEDA)(Hofmann, T., Schieberle, P.
J. Agric. Food Chem.
1998, 46, 2721-2726), the odor-active compounds could be successfully detected in solvent extracts of Maillard reaction systems composed of L-proline and reducing sugars. Amongst the volatiles detected, the popcorn-like smelling compounds 2-acetyl-1-pyrroline and 2-acetyltetrahydropyridine could be identified as the key contributors to the overall odor of thermally processed glucose/proline mixtures (Hofinann and Schieberle,
J. Agric. Food Chem.
1998, 46, 2270-2277). Although the major part of the volatile reaction products formed during these roasting processes could be unequivocally shown by AEDA to have no odor activity, it cannot be excluded that some of these odorless compounds might evoke a certain taste sensation on the tongue such as, e.g., bitterness, heating or cooling. Consequently, the sensory attributes of such reaction products from reducing carbohydrates and proline were characterized.
By application of the recently developed taste dilution analysis (Hofmann, T.
J. Agric. Food Chem.
1999, 47, 4763-4768) on HPLC fractions obtained from roasted glucose/proline mixtures two compounds could be detected, which showed an intense cooling effect on the tongue. These compounds were found to be formed in high concentrations when the hexose degradation product 2-hydroxy-3-methyl-2-cyclopenten-1-one was reacted in the presence of L-proline. After isolation by column chromatography both compounds could be obtained as pale-yellow oils with a purity of more than 99%. GC/MS and 1D- and 2D-NMR spectroscopy led to the unequivocal identification of these cooling compounds as 5-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (5-MPC) and 3-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (3-MPC).
Although these compounds have been reported earlier by Tressl et al. (1985c) and Huyghues-Dispointes et al. (1994), these authors did not report on the cooling activity of these compounds when contacted with the tongue.
Besides 3-MPC and 5-MPC, we identified another cooling-active compound in the glucose/proline mixture, namely 2,5-dimethyl-4-(1-pyrrolidinyl)-3(2H)-furanone (DMPF).
3-MPC as well as 5-MPC could easily be synthesised by heating 2-hydroxy-3-methyl-2-cyclopenten-1-one and pyrrolidinium acetate in ethanolic solution or by dry-heating of 2-hydroxy-3-methyl-2-cyclopenten-1-one in the presence of proline. In analogy, DMPF could be obtained by reacting 4-hydroxy-2,5-dimethyl-3(2H)-furanone in the presence of pyrrolidinium acetate in ethanol or in the presence of proline under dry-heating conditions, respectively.
Japanese Patent 7242661 discloses DMPF as flavoring compound to impart flavour to wheat flour foods. This patent concerns flavor emitted from such foods that were just heated. Hence the patent deals with DMPF as a flavour precursor. GB Patent No. 1096427 concerns certain cyclopentanone derivatives as interesting compounds for perfumery. Certain alpha-keto enamines are claimed, but they are mentioned only as intermediates for the synthesis of other compounds.
Thus, it is desired to obtain an improved cooling agent, particularly for use as an ingredient in foodstuffs.
SUMMARY OF THE INVENTION
The invention relates to a food, cosmetic, or pharmaceutical composition including a compound of the general formula:
wherein R
1
includes N-Pyrrolidinyl, N-Pyridinyl, N-(amino-diethyl), N-(2-carboxy-pyrrolidinyl), N-(2-Methoxycarbonyl-pyrrolidinyl), or a combination thereof; R
2
includes hydrogen, methyl, or a combination thereof; X includes methylene, ethylidene, 1-Propylidene, oxy radical, or a combination thereof; and Y includes methylene, ethylidene, 1-propylidene, oxy radical, ethan-1,2-diyl, ethen-1,2-diyl, propan-1,2-diyl, ethan-1-oxy-1-yl, or a combination thereof.
In a first embodiment, R
1
includes N-pyrrolidinyl, R
2
includes hydrogen, X includes methylene and Y includes ethylidene. In a second embodiment, R
1
includes N-pyrtolidinyl, R
2
includes methyl, X includes oxy radical and Y includes methylene. In a third embodiment, R
1
includes N-Pyrrolidinyl, R
2
includes methyl, X includes methylene and Y includes oxy radical. In a fourth embodiment, R
1
includes N-Pyrrolidinyl, R
2
includes methyl, X includes ethylidene and Y includes oxy radical. In a preferred embodiment, the compound includes at least one of 3-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (3-MPC), 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (5-MPC), 3-Methyl-2-(1-piperidinyl)-2-cyclopenten-1-one (3-MPipC), 5-Methyl-2-(1-piperidinyl)-2-cyclopenten-1-one (5-MPipC), 3-Methyl-2-diethylamino-2-cyclopenten-1-one (3-MDeaC), 5-Methyl-2-diethylamino-2-cyclopenten-1-one (5-MDeaC), 3-Methyl-2-diethylamino-2-cyclopenten-1-one (3-MDeaC), 5-Methyl-2-diethylamino-2-cyclopenten-1-one (5-MDeaC), 3-Methyl-2-(2-carboxy-1-pyrrolidinyl)-2-cyclopentene-1-one (3-MProC), 5-Methyl-2-(2-methoxycarbonyl-1-pyrrolidinyl)-2-cyclo-pentene-1-one (5-MMeproC), 5-Ethyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (5-EPC), 3,5-Dimethyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (3,5-DMPC), 3,4-Dimethyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (3,4-DMPC), 4,5-Dimethyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (4,5-DMPC), 3-Methyl-2-(1-pyrrolidinyl)-2-cyclohexen-1-one (3-MPCH), 6-Methyl-2-(1-pyrrolidinyl)-2-cyclohexen-1-one (6-MPCH), 2,5-Dimethyl-4-(1-pyrrolidinyl)-3(2H)-furanone (DMPF), 5-Methyl-4-(1-pyrrolidinyl)-3(2H )-furanone (MPF), 4,5-Dimethyl-3-(1-pyrrolidinyl)-2(5H)-furanone (2(5H)-DMPF), 4-Methyl-3-(1-pyrrolidinyl)-2(5H)-furanone (2(5H)-MPF). In a more preferred embodiment, the compound includes 2,5-Dimethyl-4-(1-pyrrolidinyl)-3(2H)-furanone, 4,5-Dimethyl-3-(1-pyrrolidinyl)-2(5H)-furanone, 4-Methyl-3-(1-pyrrolidinyl)-2(5H)-furanone, or a combination thereof.
In one embodiment, the food composition includes at least one of chocolate, ice-cream, beverages, sugar confectionery, or petfood. In another embodiment, the cosmetic composition includes a topically administered cosmetic composition. In yet another embodiment, the perfume composition includes alcohol or water, or both. In any of these embodiments, the amount of the compound of formula (A) alone or in combination includes from about 0.01 mg/kg to 3000 mg/kg of the total composition. In general, the compound of formula A is present in an amount sufficient to impart a cooling effect.
This cooling effect is preferably accomplished with little or no detectable odor. Thus, in one embodiment, the compound has a cooling threshold to odor threshold ratio less than that of menthol. In a preferred embodiment, the ratio is less than about 3.
The invention also relates to a food product including the compounds and compositions including such compounds. In a preferred embodiment, the composition is completely free of mint-odor and optionally includes a fruity or brown flavor or odor. In one embodiment, the food product is a confectionery product or a malted beverage.
In one embodiment, the invention relates to a cosmetic product including the composition, while in another embodiment the invention relates to a perfume including the composition of the invention.
The invention also
Blank Imre
Cerny Christoph
Frank Oliver
Hofmann Thomas
Ottinger Harald
Nestec S.A.
Padmanabhan Sreeni
Willis Michael A.
Winston & Strawn
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