Classifications

• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/30—Artificial sweetening agents
  • A23L27/33—Artificial sweetening agents containing sugars or derivatives
  • A23L27/37—Halogenated sugars
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/202—Aliphatic compounds
  • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
  • A23L27/2028—Carboxy compounds
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/203—Alicyclic compounds
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/204—Aromatic compounds
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/205—Heterocyclic compounds
  • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/205—Heterocyclic compounds
  • A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/30—Artificial sweetening agents
  • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
  • A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives

Definitions

• This invention relates in general to taste modifying compounds. More particularly it relates to tastands, as such term is used hereinbelow, to reduce or eliminate undesirable tastes, as such term is used hereinbelow.
• Such eatables as for example, pharmaceuticals, antibiotics, pain killers, aspirin, codeine, ibuprofen, » acetaminophen, caffeine, and unsweetened chocolate, and f sweeteners, as such term is used hereinbelow, can have
• any eatable which has a naturally undesirable taste, as such term is used hereinbelow, should be able to be rendered more palatable by the addition of an appropriate tastand, as such term is used hereinbelow.
• undesirable taste(s) shall mean any taste which is sweet, bitter, sour, alkaline, astringent, tangy, dry, sharp, cool, hot, burning, acidic, spicy, pungent, woody, smokey, umami and/or metallic.
• undesirable taste shall include any and all tastes, if such taste(s) is unwanted and include any and all aftertaste(s) , if such aftertaste is unwanted.
• caffeine may have little or no effect on a pharmaceutical and/or the off-taste of KCl, or,
• L-aspartyl-L-phenylalanine methyl ester may have little or no effect on the off-taste of another high intensity sweetener such as saccharin.
• L-Aspartyl-L-phenylalanine will have a substantial effect on the off-taste associated with L-aspartyl-L- phenylalanine methyl ester (Aspartame*) , while it has less effect on the off-taste associated with saccharin,
• Taurine has a substantial effect on the off-taste of saccharin while it has little or no effect on the off-taste associated with L-aspartyl-L-phenylalanine methyl ester (Aspartame*) .
• a "taste” shall mean any taste which is salty, bitter, sweet, sour, alkaline, umami, astringent, tangy, dry, sharp, cool, hot, burning, acidic, spicy, pungent and/or metallic. Such taste shall include any and all taste(s) as well as any and all aftertaste(s) . Once again this list is not all inclusive as one skilled in the art would recognize.
• an "eatable(s)" shall mean any material ingested. Eatables shall include, but not be limited, to materials ingested by humans, other mammals, fish, birds, and other animals.
• substantially tasteless as used herein and the appended claims is meant a compound that has substantially no taste upon initial ingestion at the levels that are appropriate to be a tastand. The aftertaste, if any, is not included in this definition.
• sweetener any material which gives a sweet perception, including but not limited to:
• A. monosaccharides including but not limited to aldoses and ketoses beginning with trioses, including but not limited to glucose, galactose, and fructose,
• sugars which include but are not limited to mono-, di- and oligosaccharides including but not limited to sucrose, maltose, lactose, etc,
• sugar alcohols which include but are not limited to sorbitol, mannitol, glycerol,
• D. carbohydrates and polysaccharides which include but are not limited to polydextrose and maltodextrin,
• high intensity sweeteners shall include but are not limited to:
• L-aspartyl-L-phenylalanine methyl ester (Aspartame*) and other related dipeptide sweeteners, saccharin, L- aspartyl-D-alanine-N-(2,2,4,4-tetramethyl thiatan-3- yl)amide (Alitame*) , 1,6-dichloro-l,6-dideoxy-/9-D- fructofuranoysl-4-chloro-4-deoxy- ⁇ -D-galactopyranoside (Sucralose*) , 6-methyl-l,2,3-oxathiazin-4(3H)-one 2,2- dioxide (Acesulfame*) , 6-methyl-l,2,3-oxathiazin- 4(3H)-one 2,2-dioxide potassium salt (Acesulfame-K*) , cyclohexylsulfamic acid (Cyclamate*) , N-(L-aspartyl)-
• low intensity sweetener as used herein and the appended claims is meant any sweetener except a high intensity sweeteners.
• masker any flavorful eatable which is used to cover and/or disguise and/or obscure an undesirable taste.
• eatables which are commonly used as maskers are sweeteners and spices such as onion, garlic, paprika, red pepper, chili powder, etc.
• low calorie eatable or "low calorie formulation” as used herein and the appended claims is meant any eatable in which the eatable has been purposely formulated for the reduced calorie market. Typically this has resulted in greater than twenty-five percent (>25%) of the calories having been removed from said eatable that would have been present in the regular non-low calorie formulation.
• Vherein X represents H, CHO . CN, CO.C 1 -C 3 al]cyl, C 0 C 1 - C 3 a 1 _c ⁇ 1
• Tastands can also be salt tastands. Tastands have the property that they will block one undesirable taste for example, bitter, and/or in some cases at the same time another undesirable taste.
• A.specific tastand may have its own particular taste but its ability to block an undesirable taste occurs at a concentration below that at which its own particular taste is perceptible. Tastar's may uncover tastes and/or off-tastes that were present in the eatable before the addition of the tastand.
• a tastand will not introduce any substantial taste and/or off-taste of its own. This property differentiates tastands from masking materials. For example to determine if a tastand is a bitter blocker it could be added to a solution of a bitter material such as KCl.
• a tastand may have the ability to block one undesirable taste more effectively than another undesirable taste. Some tastands may block only one undesirable taste effectively. A given tastand may, for example, block the perception of bitter at a level of 10-20 ppm but require 1000-10,000 ppm in order to effectively block another undesirable taste and/or tastes or it may not block the perception of another undesirable taste or tastes at any concentration. This relative effectiveness or inability to block certain tastes at all will vary from tastand to tastand and/or with concentration of the same tastand.
• Some specific tastands may block tastes that are not undesirable in certain specific applications such as sweet. Some tastands when added to an eatable may increase the perception of another taste for example the level of saltiness of the eatable. The blocking of an undesirable taste may allow in some cases an increased sensation of another taste. In this particular instance the increased salt sensation that is perceived by the addition of a tastand is allowing the tastand to act as if it were a salt enhancer.
• salt tastand as used herein and in the appended claims means a tastand which, is itself salty or is combined with another salty eatable, and when mixed with or when ingested along with an eatable possessing an undesirable taste will reduce or eliminate the perceived undesirable taste(s) of said eatable.
• salty eatables that could be used with a tastand to make a salt tastand would be NaCl, KCl, or NH 4 C1.
• tastands and eatables are molecules named variously as salts and/or acids. It is obvious to one skilled in the art that these terms are arbitrary and virtually any acid can be a salt and vice versa depending upon the macroenvironment and/or microenvironment that the molecule is in. This environment can, in some instances, change the efficacy of a particular tastand. For example, 2,4- dihydroxybenzoic acid is not nearly as potent a tastand of the off-taste of KCl as is potassium 2,4-dihydroxybenzoate.
• the solubility of the tastand in water may not be sufficient to demonstrate the blocking ability. In this case the tastand's solubility could be increased by the use of other substances to help this lack of solubility.
• Ethyl alcohol is one example of a material which can be used to increase the solubility of potential tastands to be used in the above referenced tastand test.
• Surfactants can affect the tastand by either increasing or decreasing the effectiveness of the tastand.
• a "surfactant” shall mean an amphipathic molecule.
• Such surface active agents shall include but not be limited to soaps, and/or detergents, whether ionic or non-ionic, and/or membrane lipids.
• Some surfactants can increase the effectiveness of some astands while the same surfactant may lessen the effectiveness of other tastands or not affect that particular tastand at all.
• Surfactants may affect each tastand differently.
• the surfactant that affects one particular tastand in a positive, negative or neutral sense may affect another tastand differently (i.e. a positive, negative or neutral sense and not necessarily in the same way) .
• potassium 2,4-dihydroxybenzoate potassium 2,4-dihydroxybenzoate
• This material in about one to two percent (1-2%) w/v solution is sweet.
• potassium 2,4-dihydroxybenzoate is combined with KCl at, for example, 0.25% to 0.50% by weight relative to the KCl (depending upon the individual's sensitivity to bitter) it will virtually eliminate the bitterness associated with the potassium chloride.
• Potassium 2,4-dihydroxybenzoate is also a tastand for the metallic taste associated with saccharin. If 25 to 50 milligrams of potassium 2,4-dihydroxybenzoate is added to a can of soda sweetened with saccharin (69 to 138 ppm of potassium 2,4-dihydroxybenzoate relative to the soda) the metallic taste is substantially reduced or eliminated allowing other flavors in the soda to come through.
• potassium 2,4- dihydroxybenzoate is a tastand because of its ability to block bitter taste at concentrations where it by itself is substantially tasteless. Potassium 2,4-dihydroxybenzoate is sweet only at significantly higher concentrations. In contrast, sucrose is not a tastand in that a 2% solution is sweet but even at this level the bitterness of KCl is not substantially diminished. Sucrose would be a masking material under the current definitions.
• Proteins and peptides such as skim milk, soybean casein, whey protein concentrate or casein hydrolysates.
• valine As stated above, we have repeated the taste test for valine. This was done in a 300 mM solution of valine (conditions of Tamura et al.) at various levels of taurine reported in the Tamura paper. The results we obtained were confirmed by an independent testing laboratory. The independent test laboratory's results are summarized in the following table:
• a tastand as defined hereinabove, can prevent bitter components from interacting with the taste receptor at concentrations where the tastand is tasteless or- substantially tasteless. Prevention is by a direct interaction with the receptor site, as such term is used herein, to prevent or substantially eliminate:
• taurine is added to a can of soda (354 L of s ⁇ ._. per can; 28 ppm taurine) sweetened only with saccharin the off-taste of the saccharin is substantially reduced or eliminated, while the sweet taste is relatively unaltered.
• the present teaching is analogous to a competitive inhibition with a binding site of the receptor(s) and/or a non-competitive inhibition with the site(s) that influences the receptor.
• one of our teachings is that the tastand can be effective at a low tastand concentration when compared.to the eatable with the undesirable taste.
• This distinction is not a minor teaching as in practical terms it would be impossible to add more of the debittering material than the bitter materials. If the Tamura paper's lower level of proposed use for taurine (0.5 equivalents of taurine) is added to a one percent (1%) KCl solution, the resultant solution has a pronounced off-taste which was not present when only 0.03 equivalents (0.5% by weight relative to the KCl) was used.
• the L-aspartyl-L-phenylalanine that is added as a tastand to the material sweetened with the L-aspartyl-L- phenylalanine methyl ester is in addition to the amount of L-aspartyl-L-phenylalanine that may or may not be present from the breakdown product of the L- aspartyl-L-phenylalanine methyl ester (Aspartame*) or as a manufacturing impurity.
• the use of L-aspartyl-L- phenylalanine as a tastand is an unanticipated result that was not previously known or contemplated.
• L- aspartyl-L-phenylalanine is one of the breakdown products of L-aspartyl-L-phenylalanine methyl ester (Aspartame*)
• the breakdown of the L-aspartyl-L-phenylalanine methyl ester has not been considered a desirable occurrence.
• Both the manufacturers and users of the L- aspartyl-L-phenylalanine methyl ester go to great lengths to prevent this degradation. They attempt to do this by adjusting the formulations of the products in which the material is used.
• the undesirable breakdown of the product can be slowed down by selling the material in a dry state, as well as by the purification of the material.
• L- aspartyl-L-phenylalanine is typically present in an amount less than one percent ( ⁇ 1%) of the L-aspartyl-L-phenylalanine methyl ester.
• the above example of the addition of five (5) to seven and one half (7_) mg of L-aspartyl-L-phenylalar - ⁇ e would be about four percent (4%) of the L-aspartyl-T phenylalanine methyl ester that has been used to sw: * _en the soda.
• Examples of the products that could be fo -.d from the breakdown of the L-aspartyl-L-phenylalanine methyl ester in the soda are ⁇ -L-aspartyl-L-phenylalanine, 3-L- aspartyl-L-pher.ylalanine, methanol, L-aspartyl-L- phenylalanine diketopiperazine, L-phenylalanine, L-aspartic acid, L-phenylalanine methyl ester and ⁇ -L-aspar yl-L- phenylalanine methyl ester.
• the ratio of these and other possible breakdown products will vary according to the conditions of storage (time and temperature) as well as the soda's specific composition its pH, etc.)
• the present invention teaches the use of the breakdown products, whether such breakdown occurs deliberately or accidently, of the L-aspartyl-L-phenylalanine methyl ester (Aspartame*) into one or more tastand(s) .
• Another example of a breakdown product of the L-aspartyl-L-phenylalanine methyl ester (Aspartame*) that is a tastand is 3-L-aspartyl-L- phenylalanine.
• two tastands may be needed to reduce or substantially eliminate the off-taste of the two high intensity sweeteners.
• both taurine and L-aspartyl-L- phenylalanine could be used.
• the levels of the tastands that would be needed would depend on the relative levels of the high intensity sweeteners that were used in the soda.
• tastands are sometimes preferred.
• a salt consisting of a ratio of eighty percent (80%) KCl and twenty percent (20%) NaCl with taurine at five percent (5%) relative to the KCl and three percent (3%) L-aspartyl-L-phenylalanine is sometimes preferred to a single tastand.
• Such single tastand could be for example taurine, L-aspartyl-L-phenylalanine or potassium 2,4-dihydroxybenzoate.
• sweet receptor and the bitter receptor as well as the other taste receptors may be in close proximity and/or related to one another and/or possibly one and the same. It is now known, for example, that if sweet molecules are altered slightly, particularly in their spatial arrangements and/or orientation and/or configuration of their chiral centers and/or their stereochemistry and/or by the addition or substitution and/or elimination in the molecule of various groups, that such molecules may become bitter or tasteless.
• transformation(s) the transformation of a molecule that:
• A. is a tastand will change said molecule into a molecule that is a more active tastand or less active tastand or not a tastand at all, or
• B. is not a tastand will change it to a tastand.
• Such transformations in a molecule may change the molecule from any one of these (sweet, bitter or tasteless) to any of the following: sweet, bitter or tasteless.
• the perception of sweet and the perception of bitter may be associated with the same receptor, part of the same receptor, very closely spatially related receptors or separate receptors which act together to give the associated sweet or bitter taste response, and
• receptor site(s) or “receptor(s)”.
• L- aspartyl-L-phenylalanine methyl ester (Aspartame*) is intensely sweet.
• L-aspartyl-L-phenylalanine methylamide is intensely bitter and L-aspartyl-L- phenylalanine free acid is tasteless.
• transformations extend to almost all of the known dipeptide classes of sweeteners, including the aspartyl-D- alanine amides where many of the aspartyl-D-alanine alkylamides ⁇ re sweet and many of the corresponding L- amides are bitter.
• a similar set of examples exist for the amino malonic acid derivatives, the aspartyl alanine esters and most other classes of peptide-like sweetener compounds. Transformations also extend to many other classes of compounds. For example, in the saccharin type molecules the presence or absence of nitration or alkylation can lead to a molecule that is tasteless or sweet or bitter. This is illustrated in the following example:
• the molecule may inhibit or reduce the sweetness of substances, and in some instances it will also inhibit or reduce undesirable tastes; and/or
• the molecule may inhibit or reduce the bitterness of substances, and in some instances it will also inhibit or reduce other undesirable tastes; and/or
• a sweet molecule can be spatially altered to become substantially tasteless, this molecule will likely be a tastand; and/or
• tastand in order to achieve a desired degree of reduction and/or elimination of undesirable taste(s), it has been found that more than one tastand might be needed in some cases. If more than one tastand is necessary, then it would be obvious to one skilled in the art to either have each one of the tastands ingested in a temporally appropriate manner and/or to chemically link the tastands. In the case of chemically linked tastands the basic molecule could be linked with one or more similar or dissimilar tastand molecule(s). In addition, synergism of molecules in some cases may allow two or more molecules, that in and of themselves do not appear to be tastands, to act as a tastand when said molecules are used in a temporally appropriate manner.
• potassium chloride potassium glutamate, potassium benzoate, potassium nitrate, potassium nitrite, potassium sulfate, potassium sulfite, potassium baking powder and potassium baking soda (which probably become potassium chloride or other potassium salts after baking)
• potassium chloride potassium glutamate, potassium benzoate, potassium nitrate, potassium nitrite, potassium sulfate, potassium sulfite, potassium baking powder and potassium baking soda (which probably become potassium chloride or other potassium salts after baking)
• aspirin acetaminophen
• antibiotics codeine
• caffeine unsweetened chocolate
• other medicaments or other undesirable taste(s) of the eatable undesirable taste(s) of the eatable.
• tastands have also been found to enhance salt taste.
• tastands can be used in conjunction with mixtures of substances with undesirable tastes such as, for example, potassium chloride and/or sodium chloride and/or ammonium chloride to both reduce the undesirable taste(s) and to enhance the salt taste of the sodium and/or potassium and/or ammonium chloride.
• a smoothing effect can be achieved when a tastand is added to plain unflavored, unsweetened yogurt which is normally considered tangy or acidic tasting.
• the tastands useful in the present invention are those compounds of the prior art which are tastands that are substantially tasteless. In many instances, substances of the prior art which could be tastands which are not tasteless can be rendered substantially tasteless by transformation(s) .
• substituted indicates that the molecule may have any hydrogen atom replaced or “substituted” by any of the substituents of
• A-l As used herein and the appended claims the following molecule shall be referred to as A-l and said molecule represents the general class of compounds having the structure:
• m represents 0 or 1
• n represents 0, 1, 2 or 3
• p represents 1, 2, 3, 4 or 5
• q represents 0 or 1
• R represents H or a lower alkyl (e.g. of ⁇ -C- alkyl)
• the substituents R' which may be the same or different, are each represented by one of the substituents of Group 1, in any combination.
• X + represents H + or a physiologically acceptable cation, and physiologically acceptable salts of any and/or all of the foregoing.
• B As used herein and the appended claims the following molecule shall be referred to as B-1 and said molecule represents the general class of compounds having the structure:
• R 7 may be selected from the group consisting of hydrogen and C,-C- alkyl
• g may be selected from the group consisting of hydrogen and C ⁇ C- alkyl
• R 1f is "the group, (as used herein and the appended claims the structure shall be referred to as B-2) :
• B- , R 3 , R 4 , 5 and R 6 are independently selected from the substituents of Group 1, in any combination, and physiologically acceptable salts of any and/or all of the foret ing.
• Illustrative members of particular interest in this class include:
• R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are individually represented by one of the substituents of Group 1, in any combination, and physiologically accepted salts of any and/or all of the foregoing.
• Illustrative members of particular interest in this class include:
• R 1 OC 2 H 5
• R 4 NH-CO-NH 2
• R 1 OCH 2 CH 2 CH 3
• R 2 N0 2
• R 4 NH 2
• R 1 CH 3
• R 2 N0 2
• R 4 NH 2
• n and k independently may be 0, 1 or 2; Y (which may be the same or different) may be N (nitrogen) , 0 (oxygen) , or S (sulfur) ; Q may be represented by one of the substituents of Group 3; p and q are 1 when Y is O and p and q may be independently 1 or 2 when Y is S and p and q may be independently 2 or 3 when Y is N; R (which may be the same or different when p>l) and R' (which may be the same or different when q>l) are represented by one of the substituents of Group 2 or one of the following three structures (as used herein and the appended claims the structures shall be referred to as D-2) in any combination and the appropriate stereochemistry:
• Z and Z' are the same or different and are represented by OH, OR", NH 2 , NHR” , N(R") 2 ,;
• R" may be alkyl, branched alkyl, aryl, aralkyl, alkaryl, cycloalkyl, substituted alkyl, substituted cycloalkyl substituted aryl, substituted aralkyl, substituted alkaryl, and R'" may be alkyl, branched alkyl, aryl, aralkyl, alkaryl, cycloalkyl, substituted alkyl, substituted cycloalkyl, substituted aryl, substituted aralkyl, substituted alkaryl, or an amino acid side chain (e.g.
• X* may be H + or a physiologically acceptable cation, preferably an alkali metal, alkaline earth metal or ammonium cation, and physiologically acceptable salts of any and/or all of the foregoing.
• E As used herein and the appended claims the following molecule shall be referred to as E-l and said molecule represents the general class of compounds having the structure:
• R * , R", R"', R 6 are each independently represented by one of the substituents of Group 2, in any combination; R 4 's and R 5 's which may be the same or different are each independently represented by one of the substituents of Group 3; n may be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; Z may be C, S, P or B, q is an integer from 2 to 3 and r is an integer from 1 to 3, when Z is C, q is 2; when Z is S, P or B, q may be 2 or 3; when Z is C or S, r is 1; when Z is P or B, r is 2, and physiologically acceptable salts of any and/or all of the foregoing.
• F-1 As used herein and the appended claims the following molecule shall be referred to as F-1 and said molecule represents the general class of compounds having the structure:
• n may be 0, 1 or 2; Y (which may be the same or different) may be N (nitrogen) , o (oxygen) , or S (sulfur) ; Q may be represented by one of the substituents of Group 3; p and q are 1 when Y is 0 and p and q may be independently 1 or 2 when Y is S and p and q may be independently 2 or 3 when Y is N; R (which may be the same or different when p>l) and R' (which may be the same or different when q>l) are represented by one of the substituents of Group 2 or one of the following three structures (as used herein and the appended claims the structures shall be referred to as F-2) in any combination and the appropriate stereochemistry:
• Z and Z' are the same or different and are represented by OH, -0 * X + , OR", NH 2 , NHR", N(R W ) 2 ,;
• R" is alkyl, branched alkyl, aryl, aralkyl, alkaryl, cycloalkyl, substituted alkyl, substituted cycloalkyl substituted aryl, substituted aralkyl, substituted alkaryl, and
• R"' is alkyl, branched alkyl, aryl, aralkyl, alkaryl, cycloalkyl, substituted alkyl, substituted cycloalkyl, substituted aryl, substituted aralkyl, substituted alkaryl, or an amino acid side chain (e.g.
• X + may be H + or a physiologically acceptable cation, preferably an alkali metal, alkaline earth metal or ammonium cation, and physiologically acceptable salts of any and/or all of the foregoing.
• G As used herein and the appended claims the following molecule shall be referred to as G-l and said molecule represents the general class of compounds having the structure:
• R 1 may each be represented by one of the substituents of Group 1, in any combination, and R 2 may be represented by one of the substituents of Group 2, and physiologically acceptable salts of any and/or all of the foregoing.
• H As used herein and the appended claims the following molecule shall be referred to as H-l and said molecule represents the general class of compounds having the structure:
• R 1 is 5-tetrazol
• p may be 1, 2, 3, or 4
• the substituents R 2 which may be the same or different, may each be represented by one of the substituents of Group 1, in any combination
• R 3 is represented by one of the substituents of Group 2, and physiologically acceptable salts of any and/or all of the foregoing.
• R 1 and R 2 may be independently 1, 2, 3, 4, or 5; and the substituent R 1 and R 2 , which may be the same or different, each may be represented by one of the substituents of Group 1, in any combination, and physiologically acceptable salts of any and/or all of the foregoing.
• J As used herein and the appended claims the following molecule shall be referred to as J-l and said molecule represents the general class of compounds having the structure:
• R 1 is represented by one of the substituents of Group 2
• R 2 and R 3 which may be the same or different, may be represented by one of the substituents of Group 3, in any combination, and physiologically acceptable salts of any and/or all of the foregoing.
• Illustrative of compounds of particular interest in this class are:
• R 3 CH 3
• R 2 H
• R 1 isopropyl
• R 2 R 3 -H, R ⁇ p-cyanophenylcarbamoyl and physiologically acceptable salts of any and/or all of the foregoing.
• K-l the following molecule shall be referred to as K-l and said molecule represents .e general class of compounds having the structure:
• L As used herein and the appended claims the following molecule shall be referred to as L-1 and said molecule represents the general class of compounds having the structure:
• R, R 1 and R 2 which may be the same or different, may each be represented by one of the substituents of Group 2; p may be 0 or 1; each R 3 and R 4 may be independently represented by one of the substituents of Group 3; n may be O, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20; Z is an element selected from the group consisting of carbon, sulfur, boron, or phosphorus; q is an integer from 2 to 3 and r is an integer from 1 to 3, when Z is C, q is 2; when Z is S, P or B, q may be 2 or 3; when Z is C or S, r is 1; when Z is P or B, r is 2; R 1 or R 2 can be eliminated with OH to give a cyclic amide; and physiologically acceptable salts of any and/or all of the foregoing.
• R 1 H
• R 2 t-butyl
• Z S
• q 3
• r l
• n 0
• p 0
• R 1 p-cyanophenylcarbamoyl
• M-l M-l
• substituents R, R 1 and R 2 which may be the same or different, are each represented by one of the substituents of Group 1, in any combination and R 3 is represented by one of the substituents of Group 2, wherein R, R 1 , R 2 and R 3 may be present in any combination, and physiologically* acceptable salts of any and/or all of the foregoing.
• R ⁇ R ⁇ phenyl, R 2 H, and physiologically acceptable salts of any and/or all of the foregoing.
• N-l N-l
• N-2 Illustrative of compounds of particular interest in this class is the following molecule which as used herein and the appended claims shall be referred to as N-2:
• This class includes but is not limited to:
• nitrogen atoms of these compounds may be substituted with one, two or three substituents of Group 2 f ; as appropriate. If oxygen (0) or sulfur (S) atoms exist in these molecules they may be substituted with an appropriate number of substituents from Group 2. Any aromatic groups in these compounds may be substituted with one or more of the substituents of Group 1 in any combination, and physiologically acceptable salts of any and/or all of the foregoing.
• P As used herein and the appended claims the following molecule shall be referred to as P-l and said molecule represents the general class of compounds having the generalized structure:
• substituents R and R 3 which may be the same or different, are each represented by one of the substituents of Group 1, in any combination;
• R 1 and R 2 which may be the same or different, may each be represented by one of the substituents of Group 2, in any combination, and A may be C, S, N, or O and when A is C, substitution on this carbon may be made with one or more of the substituents of Group 1, in any combination, when A is S or N substitution on this S or N may be made with one of the substituents of Group
• Q-l As used herein and the appended claims the following molecule shall be referred to as Q-l and said molecule represents the general class of compounds having the generalized structure:
• R 1 , R z , R 3 , and g which may be the same or differs * , are each represented by one of the substituents of Group 1, in any combination;
• R A and R 6 which may be the same or different, are represented by one of the substituents of Group 2, in any combination, and A may be C, S, N, or O and when A is C, substitution on this carbon may be made with one or more of the substituents of Group l, in any combination, when A is S or N substitution on this S or N may be made with one of the substituents of Group 2, and physiologically acceptable salts of any and/or all of the foregoing.
• this class is intended to include any oxidation state of the ring system, as for example, hydrogenation of one or more of the double bonds.
• R The class of compounds commonly known as natural products. This class includes but is not limited to: alkaloids, terpines, monoterpines, diterpines, triterpines, sesqueterpines, flavanoides, chalcones, dihydrochalcones, humulones, lemonoids, saponins, coumarins, isocoumarins, sinapines, steroids, flavinon.es, and physiologically acceptable salts of any and/or all of the foregoing.
• R-2 As used herein and the appended claims the following molecule shall be referred to as R-2 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-3 As used herein and the appended claims the following molecule shall be referred to as R-3 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-4 As used herein and the appended claims the following molecule shall be referred to as R-4 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-6 As used herein and the appended claims the following molecule shall be referred to as R-6 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-7 As used herein and the appended claims the following molecule shall be referred to as R-7 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-8 As used herein and the appended claims the following molecule shall be referred to as R-8 and said molecule represents the general class of compounds having, but not limited to th
• R-13 As used herein and the appended claims the following molecule shall be referred to as R-13 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-16 As used herein and the appended claims the following molecule shall be referred to as R-16 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-20 As used herein and the appended claims the following molecule shall be referred to as R-20 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-23 As used herein and the appended claims the following molecule shall be referred to as R-23 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-26 As used herein and the appended claims the following molecule shall be referred to as R-26 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-27 As used herein and the appended claims the following molecule shall be referred to as R-27 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-28 As used herein and the appended claims the following molecule shall be referred to as R-28 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-29 As used herein and the appended claims the following molecule shall be referred to as R-29 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-31 As used herein and the appended claims the following molecule shall be referred to as R-31 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-33 As used herein and the appended claims the following molecule shall be referred to as R-33 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-34 As used herein and the appended claims the following molecule shall be referred to as R-34 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-35 As used herein and the appended claims the following molecule shall be referred to as R-35 and said molecule represents the general class of compounds having, but not limited to the following structure:
• R-36 As used herein and the appended claims the following molecule shall be referred to as R-36 and said molecule represents the general class of compounds having, but not
• the ring systems depicted in the above examples may be substituted with a variety of aliphatic, alicyclic, aromatic groups, hydroxy, amino, or other substituents of group 1 or 3, as defined above, and hydroxyl, amino or thio groups may be substituted with one of the substituents of group 2, as defined above.
• the stereochemical relationships of the substituents may be cis or trans, and chiral centers may be of R or S_ configuration.
• nitrogen or oxygen atoms may be substituted with group 2, substituents or mono or polysaccharides including but not restricted to those indicated in the above examples.
• R 1 /8-D-glc 2 -c_-L-rha
• R 2 H and physiologically acceptable salts of any and/or all of the foregoing.
• S-l The class of compounds having the structure, or structures closely related to the following molecule which as used herein and the appended claims shall be referred to as S-l:
• R 1f R 2 , R 3 , and R 4 which may be the same or different are each designated by one of the substituents of Group 1.
• R- is represented by one of the substituents of Group 2
• R 6 is represented by one of the substituents of Group 3, wherein R.,, R 2 , R 3 , ⁇ and R 6 , may be present in any combination. and physiologically acceptable salts of any and/or all of the foregoing.
• T-l The class of compounds having the structure (or structures closely related to) which as used herein and the appended claims shall be referred to as T-l:
• R 1 which may be the same or different, are each represented by one of the substituents of Group 1 in any combination
• R 2 and R 3 which may be the same or different, are each represented by one of the substituents of Group 2
• each R 4 and R 5 may be independently represented by one of the substituents of Group 3 and wherein R, R 2 R 3 R 4 , and R 5 may be present in any combination
• n may be
• Z may be an element selected from the group consisting of carbon, sulfur, boron, or phosphorus; q is an integer from 2 to 3 and r is an integer from 1 to 3, when Z is C, q is 2; when Z is S, P or B, q may be 2 or 3; when Z is C or S, r is 1; when Z is P or B, r is 2;a nd physiologically acceptable salts of any and/or all of the foregoing.
• R 1 p-nitro;
• R 1 p-cyano
• n l
• R 1 p-nitro;
• A may be O(oxygen) , S(sulfur), or C(carbon) , and when A is C, n is l and when A may be O or S, n is zero;
• R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 which may be the same or different, and which may be present in any combination, may each be represented by one of the following: one of the substituents of "Group 1", O-R 13 , NH-R 13 , N-(R 13 ) 2 , or S-R 13 , where R 13 is represented by one of the substituents of "Group 2"; or two R substituents may be dehydrated to form an anhydride linkage; or two R substituents may form a cyclic structure, and physiologically acceptable salts of any and/or all of the foregoing.
• V The class of compounds having the structure (or structures closely related to) which as used herein and the appended claims shall be referred to as V-l:
• X + may be H + or a physiologically acceptable cation, preferably an alkali metal, alkaline earth metal or ammonium cation, and physiologically acceptable salts of any and/or all of the foregoing.
• X + may be H + or a physiologically acceptable cation, preferably an alkali metal, alkaline earth metal or ammonium cation, and physiologically acceptable salts of any and/or all of the foregoing.
• chelators are molecules capable of chelating with, binding with, complexing with or coordinating with metal ions. Included in this class are the physiologically acceptable salts of any and/or all of the foregoing.
• Ethylenediaminetetraacetic acid EDTA
• physiologically acceptable salts thereof EDTA
• Tastand Enhancers The effectiveness of any individual tastand as described in Classes A-X may be enhanced by one surfactant while the same surfactant may lessen the effectiveness of other tastands or not affect that particular tastand at all.
• Surfactants can increase the effectiveness of some tastands while the same surfactant may lessen the effectiveness of other tastands or not affect that particular tastand at all. Surfactants may affect each tastand differently. The surfactant that affects one particular tastand in a positive, negative or neutral sense may affect another tastand differently (i.e. a positive, negative or neutral sense and not necessarily in the same way) .
• Kier J. Pharm. Sci. 1972, 61, 1394; which is hereby incorporated by reference
• Kier expanded on the model of Shallenberger and Acree and proposed the existence of a third binding site which involved a hydrophobic interaction, which he designated as X.
• a molecule which would interact with all three (AH, B, and X) would be a higher potency sweetener than one which only interacted with the AH, B sJ a.
• Ariyoshi Bull. Chem. Soc. Japan, 1974, 47, 326-330; which is hereby incorporated by reference
• arid van der Heijden Freed Chem.
• the existence of the aspartyl zwitterionic ring cannot be proven conclusively but can be assumed a priori on the basis of evidence obtained from NMR experiments.
• the C ⁇ -C/3 bond of the aspartyl residue possesses a staggered conformation with the carboxyl moiety and the amino group in the gauche position and the sp 2 plane of the terminal aspartyl carboxylate carbon atom and the C ⁇ -C/3 bond coplanar. These conditions are conformationally favorable for the formation of the zwitterionic aspartyl ring.
• This twisting of the phenyl ring is due to packing forces within the crystal structure which result in stacking of adjacent L-aspartyl-L-phenylalanine methyl ester molecules into stable columnar structures.
• the isolated molecule from the crystal structure can be rotated 40° about the ⁇ (Phe) bond, to achieve an isoenergetic conformation in which the rings are coplanar.
• This conformation correlates closely to our proposed model for the structure of sweet dipeptides in solution ( Figure 3) .
• the L-aspartyl-L-phenylalanine methyl ester molecule is solvated and devoid of packing forces.
• the inherent flexibility of this linear peptide will easily accommodate the "L-shape" conformation required by the model.
• Figure 4 depicts L-aspartyl-L- phenylalanine methyl ester in the L "shape" required for sweet taste in the Goodman model superimposed in the 8- centered Tinti and Nofre model.
• the NH 3 + , COO " , and phenyl ring fit well into the AH, B and G sites required for a sweet taste in the Tinti and Nofre model as well as the AH, B and X sites of the Goodman model.
• Belitz (ACS, Food Taste Chemistry, 1979, 93-131; which is hereby incorporated by reference) describes minimum , requirements for bitter taste perception as a molecule possessing an AH group and a hydrophobic moiety. Using the model ascribed to Goodman above the hydrophobic moiety of Belitz would be in the -z (or bitter taste) region described by Goodman.
• the transformation of the hydrophobic zone substituent to a hydrophilic substituent, and/or the increasing or decreasing of the size of the hydrophobic substituent, and/or the increasing or decreasing of the distance between the various hydrogen bonding and hydrophobic interaction sites may result in a change in binding conformation and/or structure in a manner which prevents substantial interaction with the sweet taste (G or X) zone or substantial interaction with the bitter taste (-z) zone, thus, generating a substantially tasteless molecule.
• an inhibitor of sweet taste or bitter taste may interact in various ways with the receptor site. Consequently, depending on the nature of the interaction of a tastand with the receptor, said tastand may be capable of competing favorably against one class of compounds, say for instance sweeteners, and unfavorably against other classes of compounds such as bitter compounds. Another consequence of our finding is that a model explaining both sweet and bitter taste might include the possibility that there are separate receptors or receptor sites for sweet and bitter taste perception. Thus, if a tastand were to interact with only one of these receptors or receptor sites it could completely eliminate one se n sation without affecting the other.
• bitter taste there are at least two types of bitter taste.
• organic bitter taste which is elicited by compounds such as caffeine and the other is the bitter taste elicited by inorganic molecules like potassium ion. Consequently, a tastand may compete favorable against organic bitter taste, perhaps even favorably against sweet taste as well, and unfavorably against potassium ion, depending on the sites of interaction. Conversely the tastand may compete favorably against potassium ion and unfavorably against organic bitter or sweet tastes.
• L-aspartyl-L- phenylalanine methyl ester is approximately 200 times sweeter than sucrose.
• L-Aspartyl-L-phenylalanine methyl ester can be transformed to a bitter compound by changing the L-phenylalanine methyl ester to D-phenylalanine methyl ester (which places the phenyl ring in the -z (bitter taste) zone.
• L-Aspartyl-L-phenylalanine methyl ester can also be transformed to a tasteless compound by changing the methyl ester to a carboxylic acid.
• L-Aspartyl-L- phenylalanine (L-aspartyl-L-phenylalanine methyl ester minus the methyl ester) is tasteless and has been shown to effectively block the bitter taste of potassium ion.
• L- Aspartyl-L-phenylalanine has minimal effect on the sweet taste of L-aspartyl-L-phenylalanine methyl ester but does block the sweet taste of sucrose at very high concentrations (relative to the sucrose) .
• L-Aspartyl-L- phenylalanine has very little effect on the bitter taste of caffeine but does block the off-taste associated with L- aspartyl-L-phenylalanine methyl ester.
• N-(p- Cyanophenylcarbamoyl)-L-aspartyl-L-phenylalanine methyl ester as described by Tinti and Nofre is 14,000 times sweeter than sucrose.
• this compound When this compound is transformed into N-(p-cyanophenylcarbamoyl)-L-aspartyl-L-phenylalanine, i.e. the super sweetener minus the methyl ester, the compound becomes essentially tasteless.
• This compound can now interact with the AH, B and D, but not with the X(G) , portions of the receptor site and we have found that this compound effectively blocks the bitter taste of potassium ion and the bitter taste of caffeine while having only a very small effect on the sweet taste of sucrose.
• N-(p- Cyanophenylcarbamoyl)-aminomethanesulfonate which possesses a D and B site, and is essentially tasteless inhibits organic bitter taste (caffeine) and sweet taste, but not the bitter taste associated with potassium chloride.
• Taurine and 3-alanine which both possess an AH, B array are both example of tastands.
• tastands are predicted to be tasteless or nearly tasteless compounds which can be generated by transformation of a sweet or bitter compound in a manner that eliminates hydrophobic interactions in the -z or X(G) areas (as defined by Goodman or Tinti and Nofre) of the taste receptor(s) .
• Such tastands are capable of blocking or inhibiting any one or any combination of the three tastes; sweet, organic bitter or inorganic bitter.
• a molecule need only interact with one of the hydrogen bonding sites described above and have little or no hydrophobic interaction in the X(G) zone or -z zone to be a tastand. Frequently molecules capable of interacting with only one hydrogen bonding site and having a hydrophobic moiety will possess sufficient flexibility (depending on size) to enter the -z zone and will consequently be bitter tasting. Molecules with the ability to hydrogen bond with more than one complementary site on a receptor will have a better chance of keeping hydrophobic groups out of the X(G) and -z zone, and consequently should have a high probability of being a tastand.
• molecules which can interact with the reciprocal AH and/or B hydrogen bonding sites on a receptor as described by Goodman ( Figure 3) and whose conformation and/or structure prevents any hydrophobic interactions in the X (sweet taste) region and which also do not allow hydrophobic interactions in the -z (bitter taste) zone are tastands as defined herein.
• FIG. 3 The Goodman model for the sweet taste with L- aspartyl-L-phenylalanine methyl ester superimposed.
• the ⁇ bond shown by the arrow, has been rotated 40° from the X- ray diffraction structure.
• the hydrogen atoms have been added, with the standard bond lengths and angles.
• the AH-B and X groups of the molecule are illustrated according to the Shallenberger-Kier suggestions.
• tastands exist as racemic mixtures( ⁇ ), minus (-) , plus (+) , or diastereomeric optical isomers. It should be understood that the present invention contemplates use of the tastands in either the racemate or as the individual optical isomers. It is likely that one or the other of the optical isomers of the racemic tastands possess the greater, if not all, of the blocking or tastand activity. For example, it has been found that the (-) isomer of 2-(4-methoxyphenoxy)propionic acid possesses the majority of the activity that reduces undesirable tastes.
• the use of the most active isomer alone is advantageous in that far less tastand is needed to gain the desired reduction in undesirable taste(s) . It has further been found that tastands described above and in particular (-)-2-(4-methoxyphenoxy)propionic acid, in addition to inhibiting bitter taste also enhances the salty taste of sodium containing compounds, if employed in sufficient concentrations.
• the present invention contemplates the preparation of eatables containing, for example, low sodium chloride and the tastands in an amount sufficient to enhance the salty taste of sodium chloride.
• the present invention contemplates the preparation of eatables comprised of a mixture of substances having an undesirable taste such as potassium chloride, magnesium chloride with sodium chloride and/or ammonium chloride in conjunction with the tastands referred to herein in an amount that both reduces the undesirable taste(s) and enhances the salty taste of the sodium chloride.
• Preferred eatable admixture products of the invention comprise from slightly more than 0 up to about 300% by weight of substances with undesirable tastes such as, for example, potassium chloride and magnesium chloride and 0 to 50% by weight sodium chloride in combination with effective concentrations of a tastand(s), typically 0.001% to about 50% preferable 0.1% to about 5%.
• the present invention contemplates the preparation of eatables such as breads, biscuits, pancakes, cakes, pretzels, snack foods, baked goods etc. prepared using for example potassium bicarbonate or potassium carbonate in place of the sodium salts as leavening agents in conjunction with a tastand in an amount sufficient to eliminate the undesirable taste associated with potassium ion or other tastes.
• the tastand is typically present in an amount ranging from about 0.001% to about 50% by weight, preferably about 0.1% to about 10% by weight, of the material with the undesirable taste.
• the present invention also contemplates the preparation of preservatives for eatables comprised of the potassium salts of benzoate, nitrate, nitrite, sulfate and sulfite and so on, in conjunction with an appropriate concentration of a tastand(s) to eliminate undesirable tastes in foodstuffs.
• the tastand is usually about 0.001% to about 10%, preferably about 0.1% to about 5%, by weight of the material with the undesirable taste.
• the present invention also contemplates the use of potassium salts of flavoring agents (such as for example glutamate) in place of sodium salts. Consequently monopotassium glutamate and/or guanalate and/or inosinate in conjunction with an appropriate amount of tastand to eliminate most if not all of the undesirable tastes, thus rendering monopotassium glutamate essentially equivalent to monosodium glutamate.
• the tastand can be present from about 0.0000001% to about 300%, preferably from about 0.1% to about 5%, by weight of the material with the undesirable taste.
• the present invention also contemplates the preparation of medicaments such as aspirin, acetaminophen, ibuprofen, codeine, antibiotics, etc. in conjunction with a tastand(s) in sufficient concentration to remove or reduce the undesirable taste(s) of these materials.
• the tastand is usually 0.001% to about 50% by weight, preferably from about 0.5% to about 5% by weight of the material with the undesirable taste.
• the present invention also contemplates the preparation of eatables which have inherently undesirable tastes, such as unsweetened chocolate, in conjunction with a tastand in sufficient concentration to eliminate or reduce the bitterness of these products.
• the tastand is usually about 0.001% to about 50% by weight, preferably about 0.2% to about 5%, by weight of the material with the undesirable taste.
• concentration of tastand employed to reduce the undesirable taste(s) in any given instance will vary depending principally on the particular tastand selected, the particular substance or substances with the undesirable taste(s) , the extent of the reduction of the undesirable taste(s) desired as well as the other tastes and flavors present in the mi" .re. In most instances, concentrations of about 0.001 to .0% by weight, preferably about 0.05 to 5% of tastand to t&_ material with the undesirable taste are -.tisfactory.
• tastand when the tastand is selected for use with an admixture of sodium chloride and an undesirable tasting substance such as potassium chloride and/or magnesium chloride, it will generally be necessary to employ at least 0.2% by weight up to 10% by weight of the tastand based on the weight of the salt(s) to obtain both the reduction of the undesirable taste(s) and salty taste enhancement.
• the eatables to which the tastands of the invention can be added are without limitation and include both foodstuff and eatables having essentially no food value such as pharmaceuticals, medicaments and other eatables. Therefore, the tastands of the present invention are effective for use with all substances which have an undesirable taste(s) .
• Illustrative of substances with undesirable taste(s) with which the taste modifiers of the invention can be used are potassium chloride, ammonium chloride, sodium chloride, magnesium chloride, halide salts, naringin, caffeine, urea, magnesium sulfate, saccharin, acetosulfames, aspirin, potassium benzoate, potassium bicarbonate, potassium carbonate, potassium nitrate, potassium nitrite, potassium sulfate, potassium sulfite, potassium glutamate, food preservatives in their physiologically acceptable salts, ibuprofen, acetaminophen, antibiotics, codeine, cognac, unsweetened chocolate, cocoa beans, yogurt, preservatives, flavor enhancers, dietary supplements, gelling agents, Ph control agents, nutrients, processing aids, bodying agents, dispersing agents, stabilizers, colorings, coloring diluents, anticaking agents, antimicrobial agents, formulation aids, leavening agents, surface active agents, an
• E. alkalis or alkalis made into their corresponding salts, and/or, substances that are approved, at any time, as eatables by the Food and Drug Administration and/or that are GRAS as defined by the Flavor Extract Manufacturers' Association could then be made more palatable by the use of the tastands taught herein (hereinafter and in the appended claims referred to as "material(s)”) . These materials would or could be made more palatable by the reduction or elimination of any undesirable taste(s) associated with them. (Generally, sodium based salts are better tasting than the corresponding non-sodium salts.) The use of tastands with all of these materials as well as all of their anticipated uses is hereby anticipated by the teachings set forth herein.
• the taste of lithium chloride was greatly improved by the addition of 1% by weight (-)-2-(4- methoxyphenoxy)propionic acid sodium salt .
• the saltiness was substantially increased.
• Potassium benzoate containing 0.5% by weight (-)-2-(4- methoxyphenoxy)propionic acid sodium salt was added to foodstuffs in place of sodium benzoate. There was no detectable difference in the taste of the foodstuffs.
• Potassium nitrate and potassium nitrite containing 0.5% (-)-2-(4-methoxyphenoxy)propionic acid sodium salt were added to foodstuffs in place of the sodium salts. There was no detectable difference in the taste.
• Potassium bicarbonate/carbonate mixture containing 0.5% by weight (-)-2-(4-methoxyphenoxy)propionic acid sodium salt was used in place of baking powder for the preparation of pancakes. Essentially no bitterness was detected.
• a taste panel consisting of six tasters unanimously preferred potato chips salted with 1.6% w/w potassium chloride/sodium chloride/L-aspartyl-L-phenylalanine potassium salt (90/10/3) over potato chips salted with 1.6% w/w potassium chloride/sodium chloride (90/10) due to substantially reduced bitterness.
• EXAMPLE 44 A taste panel consisting of six tasters unanimously preferred potato chips salted with 1.6% w/w potassium chloride/sodium chloride/L-aspartyl-L-phenylalanine potassium salt (90/10/3) over potato chips salted with 1.6% w/w potassium chloride/sodium chloride (90/10) due to substantially reduced bitterness.
• the bitter and sour tastes of sodium acetylsalicylate was essentially absent from an aqueous suspension comprised of sodium acetylsalicylate (0.5 gram), water (2 mL) and potassium 2,4-dihydroxybenzoate (0.375 gram) .
• a sample of refried beans (100 g ) salted with potassium chloride (0.98 gm) , sodium chloride (0.42 gm) and sodium tartrate (0.15 gm) gave a clean, salty taste, almost completely devoid of bitterness, when compared with a sample of 100 grams of refried beans salted only with potassium chloride (0.98 gm) and sodium chloride (0.42 gm) .
• the bitterness associated with potassium chloride was reduced when a 2% aqueous solution of potassium chloride was saturated with uric acid.
• the bitterness associated with potassium chloride was reduced when a 2% aqueous solution of potassium chloride was saturated with uracil.
• the bitterness associated with potassium chloride was reduced when a 2% aqueous solution of potassium chloride was saturated with d-biotin.
• the bitterness associated with potassium chloride was reduced when a 2% aqueous solution of potassium chloride was saturated with DL-dihydroorotic acid.
• a solid preparation containing a mixture of potassium chloride (1.8 g) , sodium chloride (0.2 g) and N-(L- aspartyl)-p-aminobenzoic acid monopotassium salt (0.02 g) gave a clean salty sodium chloride-like taste.
• a solid obtained from a aqueous solution containing potassium chloride (1.8 g) , sodium chloride (0.02 g) and N-(L-aspartyl)-o-aminobenzoic acid monopotassium salt gave a bitterness-free salty taste.
• a solid lyophilized from the mixture of potassium chloride (1.8 g) , sodium chloride (0.2 g) and ⁇ - aminoethyl phosphonic acid (0.02 g) gave a clean salty taste without the bitter taste associated with potassium chloride.
• a solid made from a solution of potassium chloride (1.8 g) , sodium chloride (0.2 g) and 0-aminoethyl phosphonic acid (0.1 g) was completely free of the bitterness from potassium chloride.

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• 1992
  • 1992-11-24 HU HU9401598A patent/HUT68764A/hu unknown
  • 1992-11-24 CZ CZ941290A patent/CZ129094A3/cs unknown
  • 1992-11-24 CA CA002117284A patent/CA2117284A1/en not_active Abandoned
  • 1992-11-24 AU AU32250/93A patent/AU675778B2/en not_active Ceased
  • 1992-11-24 EP EP93900657A patent/EP0661932A4/en not_active Withdrawn
  • 1992-11-24 WO PCT/US1992/010179 patent/WO1993010677A1/en not_active Application Discontinuation
  • 1992-11-24 SK SK620-94A patent/SK62094A3/sk unknown
  • 1992-11-24 JP JP5510237A patent/JPH07504810A/ja active Pending
• 1994
  • 1994-05-26 NO NO941972A patent/NO941972L/no not_active Application Discontinuation
  • 1994-05-26 FI FI942463A patent/FI942463A/fi unknown
  • 1994-05-31 BG BG98818A patent/BG98818A/xx unknown

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