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...
Patent
1997-03-12
1998-07-14
Mosher, Mary E.
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...
426535, 426536, 426537, 426538, 426544, 426545, 426656, 426657, 530331, 562433, A23L 122, A23L 256, A23J 100
Patent
active
057800901
DESCRIPTION:
BRIEF SUMMARY
FIELD OF TECHNOLOGY AND PRIOR ART
This invention relates to the subject of flavours and more particularly to that of the flavouring of products upon which it is desired to confer a fuller and richer texture, i.e. organoleptic characteristics of the type generally associated with products containing fats, particularly butter and cheese, and an organoleptic character of the spicy salty ("savoury") type.
With this object the invention relates to the use as a flavouring ingredient of: at least one acid amino acid residue, and/or type, where X represents an amino acid residue.
By a "hydrophobic amino acid residue" is meant here a residue of one of the common amino acids which are generally recognised as being hydrophobic, namely alanine (Ala), methionine (Met), valine (Val), leucine (Leu), proline (Pro), phenylalanine (Phe), tyrosine (Tyr), isoleucine (Ile) and tryptophan (Trp).
Likewise, by "acidic amino acid residue" is here meant the residue from glutamic acid (Glu) or the residue from aspartic acid (Asp).
The tripeptide used according to the invention is thus formed from one of the abovementioned hydrophobic residues and at least one acidic residue from Glu and Asp. The third amino acid residue may again be an acidic residue, or it may be selected from the residues of one of the hydrophilic amino acids, namely cysteine (Cys), glycine (Gly), glutamine (Glu), serine (Ser), threonine (Thr) and asparagine (Asn), or one of the basic amino acids, namely lysine (Lys), arginine (Arg), ornithine (Orn) and histidine (His).
The term "amino acid residue" above has the meaning common in the art, that is that it refers to the set of atoms provided by the amino acid corresponding to the tripeptide chain. These residues will henceforth be represented by the three letter abbreviations shown in brackets above, which are in current use for defining the structure of polypeptide chains (see, e.g., Eur. J. Bioch. 1984, 138, 9-37).
In accordance with the invention, an amino acid derivative having a structure of the N-lactoyl-X type, where X represents an amino acid residue, can be used as a flavouring ingredient instead of the tripeptide, or in addition to it. This invention is therefore concerned with compounds which include an N-lactoyl or 2-hydroxypropanoyl radical, which will henceforth be indicated by the abbreviation "Lac", and a residue of one of the common amino acids mentioned above. Thus, and to provide a specific example, one of these derivatives according to the invention is the derivative (S)-Lac-Met, whose structure is as follows: ##STR1##
As will be clear from the above, because asymmetric carbon atoms are present in the structure of the compounds according to the invention, they can occur in the form of several configurational isomers which can all be used satisfactorily for the purposes of the invention, either individually, or as mixtures of isomers. Their configuration will also typically be governed by that of the starting amino acids used to prepare the tripeptides and lactoyl derivatives according to the invention.
We have in fact discovered that the abovementioned tripeptides and amino acid derivatives are very useful flavouring ingredients, which, despite the fact that they are virtually devoid of any taste of their own, are nevertheless capable of imparting very much appreciated organoleptic characteristics to the products to which they are added, specifically a quite remarkable roundness, creaminess and substance. Because of this, they can improve the oral perception or "mouthfeel" of products to which they are added, a result which is particularly useful when these tripeptides and amino acid derivatives are used for the preparation of flavouring compositions intended for flavouring "low-fat" or "low-calorie" consumer products, that is products which are low in fats, or when they are added directly to these products. In particular it has been found that when combined with other commonly used flavouring materials essentially comprising compositions based on volatile substances which are capable of confer
REFERENCES:
patent: 4130555 (1978-12-01), Ohtsuka et al.
M. Noguchi et al., "Isolation and Identification of Acidic Oligopeptides Occuring in a Flavor Potentiating Fraction from a Fish Protein Hydrolysate", J .Agr. Food Chem., vol. 23, No. 1 (1975) pp. 49-53.
Y. Yamasaki et al., "Synthesis of a Peptide with Delicious Taste", Agric. Biol. Chem., vol. 44, No. 1 (1980), pp. 93-97.
J. Coste et al., "PyBOP.RTM.: A New Peptide Coupling Reagent Devoid of Toxic By-Product", Tetrahedron Letters, vol. 31, No. 2 (1990), pp. 205-208.
E. Frerot et al., "PyBop.RTM. and PyBroP: Two Reagents for the Difficult Coupling of the .alpha.,.alpha.-Dialkyl Amino Acid, Aib", Tetrahedron, vol. 47, No. 2 (1991), pp. 259-270.
Nomenclature and Symbolism for Amino Acids and Peptides, Eur. J. Biochem., 138 (1984), pp. 9-37.
Sigma Catalogs, 1990, pp. 70-74.
Escher Sina Dorothea
Frerot Eric
Firmenich SA
Mosher Mary E.
Salimi Ali R.
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