Claims
- 1. An eatable composition comprising a sweetener which imparts an undesirable taste to the eatable, and at least one tastand in a substantially tasteless amount of from about 0.0000001 to about 300% by weight, based on the weight of the eatable, which amount is sufficient to reduce said undesirable taste, said tastand being selected from the group consisting of compounds which are substantially tasteless in the amount used and have the structure V-1: ##STR97## wherein a, r, l, and m are 0 or 1; n, j, and k are 0, 1, 2, or 3; each R.sup.2 and R.sup.3, which may be the same or different, is independently selected from the group consisting of H, alkyl, substituted alkyl, alkylene, substituted alkylene, branched alkyl, substituted branched alkyl, branched alkylene, substituted branched alkylene, aryl, substituted aryl, aralkyl, substituted aralkyl, cycloalkyl, substituted cycloalkyl, acyl, substituted acyl, benzoyl, substituted benzoyl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, trifluoromethyl, halogen, cyano, heterocyclic, substituted heterocyclic, polycyclic, and substituted polycyclic; each Y, which may be the same or different, is independently selected from the group consisting of N, O, and S; when r is 1 and Y is N, p is 2 or 3; when m is 1 and Y is N, q is 2 or 3; when r is 1 and Y is O, p is 1; when m is 1 and Y is O, q is 1; when r is 1 and Y is S, p is 1 or 2; when m is 1 and Y is S, q is 1 or 2; A is selected from the group consisting of H, C.dbd.O, O.dbd.S.dbd.O, S.dbd.O, O.dbd.P(H)OH, O.dbd.P(OH).sub.2, and O.dbd.B(H)OH; Q is selected from the group consisting of H, alkyl, substituted alkyl, alkylene, substituted alkylene, branched alkyl, substituted branched alkyl, branched alkylene, substituted branched alkylene, aryl, substituted aryl, aralkyl, substituted aralkyl, cycloalkyl, substituted cycloalkyl, acyl, substituted acyl, benzoyl, substituted benzoyl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, trifluoromethyl, halogen, cyano, heterocyclic, substituted heterocyclic, polycyclic, and substituted polycyclic; each R, which may be the same or different when p>1, and each R', which may be the same or different when q>1, is independently selected from the group consisting of H, alkyl, substituted alkyl, dialkyl, substituted dialkyl, aralkyl, substituted aralkyl, aryl, substituted aryl, diaryl, substituted diaryl, acyl, substituted acyl, cycloalkyl, substituted cycloalkyl, benzoyl, substituted benzoyl, trifluoroacetyl, alkyloxycarbonyl, substituted alkyloxycarbonyl, aryloxycarbonyl, substituted aryloxycarbonyl, alkylaminocarbonyl, substituted alkylaminocarbonyl, arylaminocarbonyl, substituted arylaminocarbonyl, amidines, substituted amidines, alkylamidines, substituted alkylamidines, arylamidines, substituted arylamidines, monosaccharide, substituted monosaccharide, disaccharide, substituted disaccharide, trisaccharide, substituted trisaccharide, oligosaccharide, substituted oligosaccharide, phosphorylated saccharides, substituted phosphorylated saccharides, arylacyl, substituted arylacyl, alkylene, substituted alkylene, heterocyclic, substituted heterocyclic, polycyclic, substituted polycyclic and the following three structures V-2: ##STR98## wherein b, c and d are 0 or 1; f is 0, 1, 2, 3, 4, 5., 6, 7, 8, 9, 10; each Y as is defined above; when d is 1 and b is 0 and Y is N, e is 2 or 3; when d is 1 and b is 0 and Y is O, e is 1; when d is 1 and b is 0 and Y is S, e is 1 or 2; A is as defined above; Q is selected from the group consisting of H, alkyl, substituted alkyl, alkylene, substituted alkylene, branched alkyl, substituted branched alkyl, branched alkylene, substituted branched alkylene, aryl, substituted aryl, aralkyl, substituted aralkyl, cycloalkyl, substituted cycloalkyl, acyl, substituted acyl, benzoyl, substituted benzoyl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, trifluoromethyl, halogen, cyano, heterocyclic, substituted heterocyclic, polycyclic, substituted polycyclic; R'" and Q together may form a cyclic structure; any of the R.sup.3 's and Q together may form a cyclic structure; any of the R.sup.3 's and R'"'s together may form a cyclic structure; Z and Z' may be the same or different and are independently selected from OH, --O.sup.- X.sup.+, OR", NH.sub.2, NHR", N(R").sub.2' ; R" is selected from alkyl, branched alkyl, aryl, aralkyl, alkaryl, cycloalkyl, substituted alkyl, substituted cycloalkyl substituted aryl, substituted aralkyl, substituted alkaryl; R'" is selected from alkyl, branched alkyl, aryl, aralkyl, alkaryl, cycloalkyl, substituted alkyl, substituted cycloalkyl, substituted aryl, substituted aralkyl, substituted alkaryl, and an amino acid side chain; where CH--CH or CH.sub.2 --CH.sub.2 bonds exist the level of unsaturation may be increased by removing one or more hydrogen atoms from each carbon atom participating in the CH--CH or CH.sub.2 --CH.sub.2 bonds; X.sup.+ is selected from H.sup.+ or a physiologically acceptable cation; and physiologically acceptable salts of any of the foregoing compounds.
- 2. A composition according to claim 1 wherein the tastand is selected from the group consisting of:
- 1. L-aspartyl-L-phenylalanine,
- 2. L-.beta.-aspartyl-L-phenylalanine,
- 3. L-aspartyl-L-tyrosine,
- 4. N-(L-aspartyl)-o-aminobenzoic acid,
- 5. N-(L-aspartyl)-p-aminobenzoic acid,
- 6. N-(p-cyanophenyl-carbamoyl)-L-aspartyl-L-phenylalanine,
- 7. N-(phenylcarbamoyl)-L-aspartyl-L-phenylalanine,
- 8. N-(L-aspartyl)-p-aminobenzenesulfonic acid,
- 9. N-(aminomalonyl)-p-aminobenzenesulfonic acid,
- 10. amino ethane phosphoric acid,
- 11. N-[N-(p-cyanophenylcarbamoyl)-L-aspartyl]-p-aminobenzenesulfonic acid,
- 12. N-(L-aspartyl)-1-aminocyclopentane-1-carboxylic acid,
- 13. N-(L-aspartyl)-1-aminocyclopropane-1-carboxylic acid,
- 14. N-(L-aspartyl)-1-aminocyclooctane-1-carboxylic acid,
- 15. N-(L-aspartyl)-1-aminocyclohexane-1-carboxylic acid,
- 16. N-(L-aspartyl)-2-aminocyclopentane-1-carboxylic acid,
- and physiologically acceptable salts of the foregoing compounds.
- 3. A composition according to claim 1 wherein the sweetener imparting an undesirable taste to the eatable is selected from the group consisting of:
- L-aspartyl-L-phenylalanine methyl ester (Aspartame.RTM.), saccharin, L-aspartyl-D-alanine-N-(2,2,4,4-tetramethyl thiatan-3yl)amide (Alitame.RTM.), 1,6-dichloro-1,6-dideoxy-.beta.-D-fructofuranoysl-4-chloro-4-deoxy-.alpha.-D-galactopyranoside (Sucralose.RTM.), 6-methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide (Acesulfame.RTM.), 6-methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide (Acesulfame-K.RTM.), cyclohexylsulfamic acid (cyclamate.RTM.),N-(l-aspartyl) N'(2,2,5,5, tetramethyl-cyclopentanoyl)1,1-diaminoethane, guanadinium class sweeteners, dihydrochalcone class sweeteners, stevioside, miraculin, thaumatin, glycerin, high fructose corn syrup, and physiologically acceptable salts thereof.
- 4. A composition according to claim 1 wherein the eatable comprises L-aspartyl-L-phenylalanine methyl ester.
- 5. A composition according to claim 4 wherein the tastand is selected from the group consisting of L-aspartyl-L-phenylalanine, L-aspartyl-L-tyrosine, and physiologically acceptable salts thereof.
- 6. A composition according to claim 1 wherein the eatable is a sweetened drink.
- 7. A composition according to claim 6 wherein the eatable comprises L-aspartyl-L-phenylalanine methyl ester.
- 8. A composition according to claim 6 wherein the tastand is selected from the group consisting of L-aspartyl-L-phenylalanine, L-aspartyl-L-tyrosine and physiologically acceptable salts thereof.
- 9. A composition according to claim 7 wherein the tastand is selected from the group consisting of L-aspartyl-L-phenylalanine, L-aspartyl-L-tyrosine and physiologically acceptable salts thereof.
- 10. A composition according to claim 1 wherein the eatable comprises 6-methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide potassium salt (Acesulfame-K.RTM.).
- 11. A composition according to claim 10 wherein the tastand is selected from the group consisting of L-aspartyl-L-phenylalanine, L-aspartyl-L-tyrosine and physiologically acceptable salts thereof.
- 12. A composition according to claim 1 wherein the eatable comprises glycerin.
- 13. A composition according to claim 12 wherein the tastand is selected from the group consisting of L-aspartyl-L-phenylalanine, L-aspartyl-L-tyrosine and physiologically acceptable salts thereof.
- 14. A composition comprising a diet soft drink sweetened with L-aspartyl-L-phenylalanine methyl ester and a sufficient amount of a tastand selected from the group consisting of L-aspartyl-L-phenylalanine, or a physiologically acceptable salt thereof, to at least reduce the undesirable taste associated with the L-aspartyl-L-phenylalanine methyl ester.
- 15. A composition according to claim 14 where the undesirable taste is selected from the group consisting of an undesireable lingering taste and an undesirable lingering sweet taste.
- 16. A composition according to claim 14 wherein the diet soft drink is diet Pepsi Cola.RTM..
- 17. A composition according to claim 15 wherein the diet soft drink is diet Pepsi Cola.RTM..
- 18. A composition according to claim 14 wherein the diet soft drink is diet Coca-Cola.RTM..
- 19. A composition according to claim 15 wherein the diet soft drink is diet Coca-Cola.RTM..
- 20. A composition according to claim 1 wherein the eatable comprises a compound selected from the group consisting of saccharin and physiologically acceptable salts thereof.
- 21. A method of making an eatable composition according to claim 1 from an eatable which comprises a sweetener which imparts an undesirable taste to the eatable, which method comprises the step of incorporating in, or ingesting with, said eatable at least one tastand in a substantially tasteless amount of from about 0.0000001 to about 300% by weight, based on the weight of the eatable, which amount is sufficient to reduce said undesirable taste, said tastand being selected from the group consisting of compounds which are substantially tasteless in the amount used and have the structure V-1: ##STR99## wherein a, r, l, and m are 0 or 1; n, j, and k are 0, 1, 2, or 3; each R.sup.2 and R.sup.3, which may be the same or different, is independently selected from the group consisting of H, alkyl, substituted alkyl, alkylene, substituted alkylene, branched alkyl, substituted branched alkyl, branched alkylene, substituted branched alkylene, aryl, substituted aryl, aralkyl, substituted aralkyl, cycloalkyl, substituted cycloalkyl, acyl, substituted acyl, benzoyl, substituted benzoyl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, trifluoromethyl, halogen, cyano, heterocyclic, substituted heterocyclic, polycyclic, and substituted polycyclic; each Y which may be the same or different, is independently selected from the group consisting of N, O, and S; when r is 1 and Y is N, p is 2 or 3; when m is 1 and Y is N, q is 2 or 3; when r is 1 and Y is O, p is 1; when m is 1 and Y is O, q is 1; when r is 1 and Y is S, p is 1 or 2; when m is 1 and Y is S, q is 1 or 2; A is selected from the group consisting of H, C.dbd.O, O.dbd.S.dbd.O, S.dbd.O, O.dbd.P(H)OH, O.dbd.P(OH).sub.2, and O.dbd.B(H)OH; Q is selected from the group consisting of H, alkyl, substituted alkyl, alkylene, substituted alkylene, branched alkyl, substituted branched alkyl, branched alkylene, substituted branched alkylene, aryl, substituted aryl, aralkyl, substituted aralkyl, cycloalkyl, substituted cycloalkyl, acyl, substituted acyl, benzoyl, substituted benzoyl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, trifluoromethyl, halogen, cyano, heterocyclic, substituted heterocyclic, polycyclic, and substituted polycyclic; each R, which may be the same or different when p>1, and each R', which may be the same or different when q>1, is independently selected from the group consisting of H, alkyl, substituted alkyl, dialkyl, substituted dialkyl, aralkyl, substituted aralkyl, aryl, substituted aryl, diaryl, substituted diaryl, acyl, substituted acyl, cycloalkyl, substituted cycloalkyl, benzoyl, substituted benzoyl, trifluoroacetyl, alkyloxycarbonyl, substituted alkyloxycarbonyl, aryloxycarbonyl, substituted aryloxycarbonyl, alkylaminocarbonyl, substituted alkylaminocarbonyl, arylaminocarbonyl, substituted arylaminocarbonyl, amidines, substituted amidines, alkylamidines, substituted alkylamidines, arylamidines, substituted arylamidines, monosaccharide, substituted monosaccharide, disaccharide, substituted disaccharide, trisaccharide, substituted trisaccharide, oligosaccharide, substituted oligosaccharide, phosphorylated saccharides, substituted phosphorylated saccharides, arylacyl, substituted arylacyl, alkylene, substituted alkylene, heterocyclic, substituted heterocyclic, polycyclic, substituted polycyclic and the following three structures V-2: ##STR100## wherein b, c and d are 0 or 1; f is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10; each Y is defined above; when d is 1 and b is 0 and Y is N, e is 2 or 3; when d is 1 and b is 0 and Y is O, e is 1; when d is 1 and b is 0 and Y is S, e is 1 or 2; A is as defined above; Q is selected from the group consisting of H, alkyl, substituted alkyl, alkylene, substituted alkylene, branched alkyl, substituted branched alkyl, branched alkylene, substituted branched alkylene, aryl, substituted aryl, aralkyl, substituted aralkyl, cycloalkyl, substituted cycloalkyl, acyl, substituted acyl, benzoyl, substituted benzoyl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, trifluoromethyl, halogen, cyano, heterocyclic, substituted heterocyclic, polycyclic, substituted polycyclic; R'" and Q together may form a cyclic structure; any of the R.sup.3 's and Q together may form a cyclic structure; any of the R.sup.3 's and R'"'s together may form a cyclic structure; Z and Z' may be the same or different and are independently selected from OH, --O.sup.+ X.sup.+, OR", NH.sub.2, NHR", N(R").sub.2' ; R" is selected from alkyl, branched alkyl, aryl, aralkyl, alkaryl, cycloalkyl, substituted alkyl, substituted cycloalkyl substituted aryl, substituted aralkyl, substituted alkaryl; R'" is selected from alkyl, branched alkyl, aryl, aralkyl, alkaryl, cycloalkyl, substituted alkyl, substituted cycloalkyl, substituted aryl, substituted aralkyl, substituted alkaryl, and an amino acid side chain; where CH--CH or CH.sub.2 --CH.sub.2 bonds exist the level of unsaturation may be increased by removing one or more hydrogen atoms from each carbon atom participating in the CH--CH or CH.sub.2 --CH.sub.2 bonds; X.sup.+ is selected from H.sup.+ or a physiologically acceptable cation; and physiologically acceptable salts of any of the foregoing compounds.
- 22. A method in accordance with claim 21 wherein the tastand is selected from the group consisting of:
- 1. L-aspartyl-L-phenylalanine,
- 2. L-.beta.-aspartyl-L-phenylalanine,
- 3. L-aspartyl-L-tyrosine,
- 4. N-(L-aspartyl)-o-aminobenzoic acid,
- 5. N-(L-aspartyl)-p-aminobenzoic acid,
- 6. N-(p-cyanophenyl-carbamoyl)-L-aspartyl-L-phenylalanine,
- 7. N-(phenylcarbamoyl)-L-aspartyl-L-phenylalanine,
- 8. N-(L-aspartyl)-p-aminobenzenesulfonic acid,
- 9. N-(aminomalonyl)-p-aminobenzenesulfonic acid,
- 10. amino ethane phosphoric acid,
- 11. N-[N-(p-cyanophenylcarbamoyl)-L-aspartyl]-p-aminobenzensulfonic acid,
- 12. N-(L-aspartyl)-1-aminocyclopentane-1-carboxylic acid,
- 13. N-(L-aspartyl)-1-aminocyclopropane-1-carboxylic acid,
- 14. N-(L-aspartyl)-1-aminocyclooctane-1-carboxylic acid,
- 15. N-(L-aspartyl)-1-aminocyclohexane-1-carboxylic acid,
- 16. N-(L-aspartyl)-2-aminocyclopentane-1-carboxylic acid,
- and physiologically acceptable salts of the foregoing.
- 23. A method in accordance with claim 21 wherein the sweetener imparting an undesirable taste to the eatable is selected from the group consisting of:
- L-aspartyl-L-phenylalanine methyl ester (Aspartame.RTM.), saccharin, L-aspartyl-D-alanine-N-(2,2,4,4-tetramethyl thiatan-3yl)amide (Alitame.RTM.), 1,6-dichloro-1,6-dideoxy-.beta.-D-fructofuranoysl-4-chloro-4-deoxy-.alpha.-D-galactopyranoside (Sucralose.RTM.), 6-methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide (Acesulfame.RTM.), 6-methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide (Acesulfame-K.RTM.), cyclohexylsulfamic acid (cyclamate), N-(l-aspartyl)-N'(2,2,5,5,tetramethylcyclopentanoyl)1,1-diaminoethane, guanadinium class sweeteners, dihydrochalcone class sweetener, stevioside, miraculin, thaumatin, glycerin, high fructose corn syrup, and physiologically acceptable salts thereof.
- 24. A method in accordance with claim 21 wherein the eatable comprises L-aspartyl-L-phenylalanine methyl ester.
- 25. A method in accordance with claim 24 wherein the tastand is selected from the group consisting of L-aspartyl-L-phenylalanine, L-aspartyl-L-tyrosine and physiologically acceptable salts thereof.
- 26. A method in accordance with claim 21 wherein the eatable is a sweetened drink.
- 27. A method in accordance with claim 26 wherein the drink is sweetened with L-aspartyl-L-phenylalanine methyl ester.
- 28. A method in accordance with claim 26 wherein the tastand is selected from the group consisting of L-aspartyl-L-phenylalanine, L-aspartyl-L-tyrosine and physiologically acceptable salts thereof.
- 29. A method in accordance with claim 27 wherein the tastand is selected from the group consisting of L-aspartyl-L-phenylalanine, L-aspartyl-L-tyrosine and physiologically acceptable salts thereof.
- 30. A method in accordance with claim 21 wherein the eatable comprises 6-methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide potassium salt (Acesulfame-K.RTM.).
- 31. A method in accordance with claim 30 wherein the tastand is selected from the group consisting of L-aspartyl-L-phenylalanine, L-aspartyl-L-tyrosine and physiologically acceptable salts thereof.
- 32. A method in accordance with claim 21 wherein the eatable comprises glycerin.
- 33. A method in accordance with claim 21 wherein the tastand is selected from the group consisting of L-aspartyl-L-phenylalanine, L-aspartyl-L-tyrosine and physiologically acceptable salts thereof.
- 34. A method of providing an improved tasting diet soft drink sweetened with L-aspartyl-L-phenylalanine methyl ester, said method comprising the steps of incorporating in, or ingesting with, said soft drink a sufficient amount of a tastand selected from the group consisting of L-aspartyl-L-phenylalanine, or a physiologically acceptable salt thereof; to reduce or remove the undesirable taste associated with the L-aspartyl-L-phenylalanine methyl ester.
- 35. A method according to claim 34 where the undesirable taste is selected from the group consisting of an undesireable lingering taste and an undesirable lingering sweet taste.
- 36. A method in accordance with claim 34 wherein the diet soft drink is diet Pepsi Cola.RTM..
- 37. A method in accordance with claim 35 wherein the diet soft drink is diet Pepsi Cola.RTM..
- 38. A method in accordance with claim 34 wherein the diet soft drink is diet Coca Cola.RTM..
- 39. A method in accordance with claim 35 wherein the diet soft drink is diet Coca Cola.RTM..
- 40. A method in accordance with claim 21 wherein the eatable comprises a compound selected from the group consisting of saccharin and physiologically acceptable salts thereof.
Parent Case Info
This application is a division of application Ser. No. 08/877,472 filed Jun. 17, 1997; which is a division of 08/462,265 filed Jun. 5, 1995 now U.S. Pat. No. 5,700,792; which is a division of Ser. No. 08/451,063 filed May 25, 1995 now U.S. Pat. No. 5,637,618; which is a continuation of Ser. No. 08/067,537 filed May 26, 1993 now abandoned; which is a continuation-in-part of International Application No. PCT/US92/10179 filed Nov. 24, 1992; and a continuation-in-part of application Ser. No. 07/799,207 filed Nov. 27, 1991, now abandoned which in turn is a continuation-in-part of application Ser. No. 07/531,388 filed June 1, 1990 now U.S. Pat. No. 5,232,735.
US Referenced Citations (12)
Foreign Referenced Citations (1)
| Number |
Date |
Country |
| 052631 |
Jan 1978 |
JPX |
Non-Patent Literature Citations (1)
| Entry |
| CA Abstract, 89:152571, for JP 53052631 (1978). |
Divisions (3)
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Number |
Date |
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| Parent |
877472 |
Jun 1997 |
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| Parent |
462265 |
Jun 1995 |
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| Parent |
451063 |
May 1995 |
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Continuations (1)
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Number |
Date |
Country |
| Parent |
067537 |
May 1993 |
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Continuation in Parts (2)
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Number |
Date |
Country |
| Parent |
PCTUS9210179 |
Nov 1992 |
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| Parent |
531388 |
Jun 1990 |
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