Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Flavor per se – or containing flavor or flavor improver of...
Reexamination Certificate
1996-05-30
2001-09-11
Woodward, Michael P. (Department: 1631)
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Flavor per se, or containing flavor or flavor improver of...
C426S069000, C426S533000, C426S650000, C426S656000, C426S804000
Reexamination Certificate
active
06287620
ABSTRACT:
TECHNICAL FIELD
The present invention relates to the flavoring industry and more particularly to the use of &agr;-keto-acids as flavoring ingredients for the preparation of flavoring compositions and/or flavored food or pharmaceutical products.
Tha &agr;-keto-acids are a group of compounds which obey the general formula
wherein symbol R can represent hydrogen or a large variety of alkyl radicals, saturated or unsaturated, linear or branched, optionally substituted by hydroxy, amino, phenyl, hydroxy-phenyl, carboxy, mercapto, methylthio, guanidino and other groups. More than a hundred of such compounds are presently known and the invention concerns more particularly the use as a flavoring ingredient of a certain number of these acids mentioned below, which are edible.
PRIOR ART
A good number of these compounds are known as components of natural products, wherein they are formed by fermentation of amino acids resulting from the enzymatic transformation of proteins. Thus, several of these acids have been found, among others, in cocoa, in several types of cheese, or yet in beer.
It is also known that the &agr;-keto-acids can play a decisive role in the metabolism of living beings when acting as precursors of essential and semi-essential amino acids, and this renders them useful in the pharmaceutical industry. In this context, they have been known to be used, for example, as active principles in medications intended for the treatment of kidney or liver diseases. However, their use to this effect presents some difficulties related to their unpleasant odor and taste (see for example, FR 2 419 723 and EP 406 811), and this has prompted a number of researchers to propose particular carrier systems, e.g. cyclodextrine clathrates (EP 406 811), which make it possible to palliate such problems.
In view of the preceding comments, it may not be surprising to observe that, in spite of the many prior art reports related to the natural occurrence of certain of these keto-acids and to their use for therapeutical applications, to our knowledge, it has never been suggested to apply them as active flavoring ingredients, to improve the taste and aroma of edible products, by adding them to these products in essentially pure form, i.e. devoid of the natural substances which may accompany them in a natural product.
We have now surprisingly discovered that the above-mentioned compounds are very advantageous flavoring ingredients, and that the scope of their use to this effect can be extremely general. We have thus established that, upon addition of one or several of these compounds to flavoring compositions o r concentrated flavors of a large variety, one could improve in an unexpected manner the taste of said compositions and concentrates, namely the “mouthfeel” of these products, without observing any harmful organoleptic effect, unlike what could have been expected in view of the prior art.
DESCRIPTION OF THE INVENTION
Thus, an object of the present invention is an artificial flavoring composition containing as an active ingredient one or several compounds selected from the group consisting of the &agr;-keto-acids in essentially pure form, as well as their edible derivatives and precursors susceptible of being formed from said acids, respectively liberate said acids, in the utilization medium.
By an &agr;-keto-acid in essentially pure form it is understood here an &agr;-keto-acid which is not accompanied by the substances with which it may occur in a natural origin product, nor in the same proportions.
According to a preferred embodiment of the flavoring composition of the invention, the active ingredient is formed of one or several compounds selected in the group consisting of glyoxylic, 2-oxo-propanoic, 2-oxo-butanoic, 3-methyl-2-oxo-butanoic, 3-methyl-2-oxo-pentanoic, 4-methyl-2-oxo-pentanoic, 3-hydroxy-2-oxo-propanoic, oxalacetic, 2-oxo-glutaric, 2-oxo-3-phenyl-propanoic, 3-(4-hydroxyphenyl)-2-oxo-propanoic, 2-oxo-1H-indole-3-propanoic, 2-oxo-1H-imidazole-4-propanoic, 4-methylthio-2-oxo-butanoic, 3-mercapto-2-oxo-propanoic, 3-hydroxy-2-oxo-butanoic, 6-amino-2-oxo-hexanoic and 5-guanidino-2-oxo-pentanoic acids, and by the edible derivatives and precursors of these acids susceptible of being or of liberating the latter in the utilization medium.
By “utilization medium” it is meant here, either the medium of the actual flavoring composition, which will also typically contain one or more current flavoring ingredients of natural or synthetic origin, optionally in admixture with the usual solvents and adjuvants, or the medium of the food or pharmaceutical product into which said flavoring composition may be incorporated. It is apparent therefore, that such a medium will possess physical and chemical characteristics, and namely a pH, which are a function of the nature of the varied components present in the flavoring composition or in the above-mentioned end-products and which can condition the chemical form in which the &agr;-keto-acid occurs in said medium and produces its organoleptic effect. One has in mind in particular the possible formation of hydrates in aqueous solution, or yet the derivatives which can result from keto-enol type tautomeric equilibria. The group of compounds from which the active ingredient of the flavoring composition according to the invention can be selected thus includes these potential derivatives which can be formed from said &agr;-keto-acids under the conditions of their utilization.
Likewise, as the edible derivatives or precursors of the &agr;-keto-acids in the context of the invention, one can cite in particular the edible salts of these acids, for example their salts of alkaline metals such as sodium, lithium, magnesium, potassium or calcium, or yet their C
1
to C
4
alkyl esters.
By C
1
to C
4
alkyl esters it is referred here the ester derivatives of the above-mentioned acids wherein the ester function contains a saturated or unsaturated, linear or branched alkyl group, having 1 to 4 carbon atoms. Among others, these include the methyl and ethyl esters.
Other edible precursors of the &agr;-keto-acids include the corresponding amino acids and namely the essential and semi-essential amino acids and their salts of alkaline metal. When referring here to the amino acids, one is referring more particularly to the enantiomers of these acids which possess an L configuration, which have a natural occurrence.
The addition according to the invention of the &agr;-keto-acids and/or their above-mentioned derivatives and precursors, as active ingredients, to the flavoring compositions and concentrates typically produces an improvement or enhancement of the impact and of the rich, creamy and full feeling of the composition in the mouth, i.e. of the gustative impressions connected to the texture, volume and fullness as perceived upon tasting these products and which are generally referred to under the designation of the “mouthfeel” of the product. Moreover, these effects may be accompanied of other imparted aromatic attributes, namely those associated with the volatile notes responsible for the characteristic odor and taste of a certain food product, for the flavoring of which the composition or concentrated is intended.
Now, this is a totally unexpected effect in view of the prior art knowledge, particularly as regards the literature reports related to the natural occurrence of these compounds in cheeses. These reports do in fact suggest that the said compounds may play a role in the taste of the cheese, which role may be more or less important depending on the nature of the latter, without however qualifying this role and never associating it to the cheeses' characteristics which relate to the texture and more or less creamy and buttery nature thereof, e. g. their mouthfeel.
Furthermore, as is apparent from the examples presented further on, in a number of applications, upon the use of certain compounds among those cited, there was observed a radical modification of the properties of the base composition, with a remarkable improvement not only of the mouthfeel of this co
Benzi François
van Beem Nicole
Van Den Ouweland Godefridus
Vanrietvelde Claude
Firmenich SA
Woodward Michael P.
Zeman Mary K.
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