Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-11-29
2000-11-07
Chang, Ceila
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546214, 426537, A61K 31445, C07D30766, A23L 1226
Patent
active
061437689
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new furan derivatives, to processes for their synthesis and to their use as flavour enhancer.
SUMMARY
The subject of the present invention is compounds of formula I: ##STR2## wherein A is a piperidin-1-yl group which is unsubstituted or substituted with one or more groups chosen from a (C.sub.1 -C.sub.4)alkyl group and a hydroxyl group;
R.sub.1 and R.sub.2, which are identical or different, are chosen from a hydrogen atom, a (C.sub.1 -C.sub.4)alkyl group and a hydroxyl group, as well as their edible salts.
Preferably, the subject of the present invention is a compound of formula I in which A is an unsubstituted piperidin-1-yl group and R.sub.1 and R.sub.2, which are identical, represent a methyl group.
The said preferred compound is therefore 4-hydroxy-2,5-dimethyl-3-piperidylfuran ##STR3##
The subject of the present invention is also a process for the synthesis of the compounds of formula I as defined above, which consists in reacting a piperidine of formula AH, where A is as defined above, with a compound of formula II: ##STR4## wherein R.sub.1 and R.sub.2, which are identical or different, are chosen from a hydrogen atom, a (C.sub.1 -C.sub.4)alkyl group and a hydroxyl group, in order to obtain a compound of formula I as defined above.
DETAILED DESCRIPTION
More particularly, the 4-hydroxy-2,5-dimethyl-3-piperidylfuran may be obtained from L-rhamnose, which is reacted with piperidine, the 4-hydroxy-2,5-dimethyl-3(2H)furanone formed reacting with the piperidine.
According to a preferred embodiment of the present invention, the 4-hydroxy-2,5-dimethyl-3-piperidylfuran may be prepared according to the method comprising the steps consisting in: in molar proportions 1.65/1/2.2; solvent have evaporated off; solvent, and then washing with water, acidifying the aqueous phase and then evaporating the organic solvent.
The authors of the present invention have discovered that the compounds of formula I as defined above exhibit a flavour enhancing property.
Edible and nontoxic, the compounds of the invention are therefore useful as flavour or taste enhancers in food preparations. Among the preferred food preparations, there may be mentioned in particular preparations of the drinks, yoghurt, ice-cream and confectionery type, and the like.
The compounds of the present invention may more particularly be used in combination with at least one flavour, for example in combination with 4-hydroxy-2,5-dimethyl-3(2H)furanone (strawberry, caramel, pineapple flavour), vanallin (vanilla flavour) or maltol (caramel flavour).
The compounds of the present invention may be used in a concentration of 5 to 50 ppm, preferably of 8 to 20 ppm in the food preparation.
When they are combined with a flavour, the compounds of the present invention may in particular be used in a proportion of about 1 to 10%, preferably of about 3 to 4% relative to the flavour.
The compounds of the present invention may be dissolved in a solvent, optionally in combination with at least one flavour.
Alcoholic solvents, such as for example ethyl alcohol, isopropyl alcohol or monopropylene glycol, are preferred solvents.
The subject of the present invention is therefore also a composition comprising a compound of formula I as defined above, in combination with at least one flavour, in a preferably alcoholic solvent. More particularly, the subject of the present invention is a composition as defined above, in which the said compound of formula I is present in a proportion of 1 to 10% relative to the said flavour.
The following examples illustrate the invention without limiting the scope thereof.
EXAMPLE 1
Synthesis of 4-Hydroxy-2,5-Dimethyl-3-Piperidylfuran
4-Hydroxy-2,5-dimethyl-3-piperidylfuran is a coproduct of synthesis of 4-hydroxy-2,5-dimethyl-3(2H)furanone ##STR5## from L-rhamnose.
L-Rhamnose (1.65 mol) in anhydrous ethyl alcohol is stirred in the presence of piperidine (1 mol) and acetic acid (2.2 mol). The reaction medium is heated under reflux. The solvent and the acetic acid are removed by evaporation. The remai
REFERENCES:
Washino et al. "<Manufacture of hydroxfuranosnes fro flavoring materials" CA 111:97064, 1987.
Shigematsu, "Components of roasting flavor formed in the heating reaction between amino compounds and sugars" Nippo Sembai Kosha Chuo kenkyusho Kenkyu Hokoku, v. 118, pp. 119-182, 1976.
Akbar Emami
Chang Ceila
Francaise d'Aromes et Parfums
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