MXPA00002552A - METAL COMPLEXES OF N-[N-(3,3-DIMETHYLBUTYL) -L-&agr;-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER - Google Patents
METAL COMPLEXES OF N-[N-(3,3-DIMETHYLBUTYL) -L-&agr;-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTERInfo
- Publication number
- MXPA00002552A MXPA00002552A MXPA/A/2000/002552A MXPA00002552A MXPA00002552A MX PA00002552 A MXPA00002552 A MX PA00002552A MX PA00002552 A MXPA00002552 A MX PA00002552A MX PA00002552 A MXPA00002552 A MX PA00002552A
- Authority
- MX
- Mexico
- Prior art keywords
- phenylalanine
- dimethylbutyl
- methyl ester
- aspartyl
- metal complexes
- Prior art date
Links
- IAOZJIPTCAWIRG-QWRGUYRKSA-N Aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 title claims abstract description 46
- 235000010357 aspartame Nutrition 0.000 title claims abstract description 42
- 229910052751 metal Inorganic materials 0.000 title abstract description 25
- 239000002184 metal Substances 0.000 title abstract description 25
- 235000003599 food sweetener Nutrition 0.000 claims abstract description 24
- 239000003765 sweetening agent Substances 0.000 claims abstract description 24
- 239000007788 liquid Substances 0.000 claims abstract description 12
- -1 3,3-dimethylbutyl Chemical group 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L MgCl2 Chemical group [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 8
- 150000004696 coordination complex Chemical class 0.000 claims description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical group [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 6
- 239000001110 calcium chloride Substances 0.000 claims description 5
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 5
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L Zinc sulfate Chemical group [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 2
- BIGUDPKZXJTJKJ-UHFFFAOYSA-K aluminum;chloride;sulfate Chemical group [Al].[Cl-].[O-]S([O-])(=O)=O BIGUDPKZXJTJKJ-UHFFFAOYSA-K 0.000 claims description 2
- LJBZENKYROGMMZ-UHFFFAOYSA-F dialuminum;zinc;tetrasulfate Chemical group [Al+3].[Al+3].[Zn+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O LJBZENKYROGMMZ-UHFFFAOYSA-F 0.000 claims description 2
- 229960001763 zinc sulfate Drugs 0.000 claims description 2
- 229910000368 zinc sulfate Chemical group 0.000 claims description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 108010016626 Dipeptides Proteins 0.000 abstract description 4
- 235000013615 non-nutritive sweetener Nutrition 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- 108010011485 Aspartame Proteins 0.000 description 9
- 229960003438 Aspartame Drugs 0.000 description 9
- HLIAVLHNDJUHFG-HOTGVXAUSA-N Neotame Chemical compound CC(C)(C)CCN[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-HOTGVXAUSA-N 0.000 description 9
- 239000000605 aspartame Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 8
- 239000004384 Neotame Substances 0.000 description 6
- 108010070257 neotame Proteins 0.000 description 6
- 235000019412 neotame Nutrition 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000013305 food Nutrition 0.000 description 4
- 230000000007 visual effect Effects 0.000 description 4
- 235000013361 beverage Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229960002713 calcium chloride Drugs 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 229960002337 magnesium chloride Drugs 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229940052299 Calcium Chloride Dihydrate Drugs 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 229940050906 Magnesium chloride hexahydrate Drugs 0.000 description 1
- PVCCISSCNBXSKD-UHFFFAOYSA-N O.O.O.O.O.O.O.[Zn] Chemical compound O.O.O.O.O.O.O.[Zn] PVCCISSCNBXSKD-UHFFFAOYSA-N 0.000 description 1
- 210000003254 Palate Anatomy 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 229960000716 TONICS Drugs 0.000 description 1
- YPKOTWSAVCIFAM-UHFFFAOYSA-N [Na].CCC Chemical compound [Na].CCC YPKOTWSAVCIFAM-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 235000012174 carbonated soft drink Nutrition 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229940032296 ferric chloride Drugs 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000001256 tonic Effects 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
Abstract
Dipeptide sweeteners are disclosed that are metal complexes of N-[N-(3, 3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester represented by formula (I) wherein Xp+ is selected from the group consisting of Al3+, Fe2+, Fe3+, Ca2+, Mg2+ and Zn2+;Yq- is selected from the group consisting of Cl-, SO42-, PO43- and CH3COO-;x is a number from 1 to 4 and pn=qm. Also disclosed is a liquid low-calorie sweetener containing such metal complexes.
Description
METALLIC COMPOUNDS OF N-rN- (1) -METHYL ESTER (3,3.- DIMETHYLBUTHYL-L-a-ASPARTILI-L-PHENYLALANINE
BACKGROUND OF THE INVENTION
FIELD OF THE INVENTION
This invention relates to novel sweeteners. In particular, the invention relates to metal complexes of the N-alkylated derivative of aspartame, 1-methyl ester of N- [N- (3,3-dimethylbutyl) -L-a-aspartyl] -L-phenylalanine, ie neotame. The invention also relates to a low calorie liquid sweetener containing said metal complexes.
RELATED PREVIOUS TECHNIQUE
It is known that several N-substituted derivatives of aspartame, such as those described in the patent of E.U.A. No. 5,480,668 are useful as sweetening agents. In particular, it is known that the N-alkylated derivative of aspartame, 1-methyl ester of N- [N- (3,3-dimethylbutyl) -L-aspartyl] -L-phenylalanine is a very potent sweetening agent since it has been reported that its sweetening power, based on weight, is at least 50 times that of aspartame and approximately 10,000 times that of sucrose. Because sweetening agents are often used in aqueous solutions and beverages, it is important that they have an acceptable dissolution rate and an effective level of solubility to be commercially viable. The patent of E.U.A. No. 4,031, 258 discloses certain inorganic salts of dipeptide sweeteners that provide improved dissolution and solubility. The patent of E.U.A. 4,448,716 discloses dipeptide sweeteners: metal complexes with improved dissolution, solubility and stability rates. However, N- [N- (3,3-dimethylbutyl) -L-a-aspartyl] -L-phenylalanine 1-methyl ester is not described or suggested. It is known that the physical properties as well as the stability of aspartame and other peptides can be modified by conversion of their salts. This is described, for example, in the US patents. Us.
4,031, 258 and 4,153,737. The patent of E.U.A. 4,153,737 also describes low-calorie concentrated liquid sweeteners. Structurally, however, 1-methyl ester of N- [N- (3,3-dimethylbutyl) -L-aspartyl] -L-phenylalanine and aspartame differ in that 1-methyl ester of N- [N- (3 , 3-dimethylbutyl) -La-aspartyl] -L-phenylalanine, a substituent of volumetric neohexyl is present in the nitrogen of the amine.
Aspartame Neotame
This structural difference results in severe differences in the physical and chemical properties of these compounds. For example, the melting point of N- [N- (3,3-dimethylbutyl) -La-aspartl] -L-phenylalanine 1-methyl ester is 80 ° C, whereas for aspartame it is 248 ° C . In addition, N- [N- (3,3-dimethylbutyl) -L-a-aspartyl] -L-phenylalanine 1-methyl ester has a much higher solubility in organic solvents than aspartame, and a much lower solubility in water. It is also known that N- [N- (3,3-dimethylbutyl) -L-α-aspartyl] -L-phenylalanine 1-methyl ester has greater stability than aspartame under some pH conditions, as described in the US Pat. USA No. 5,480,688. The difference expressed in sweetness between the two compounds is additional evidence of their chemical inequality. Moreover, it is also known that a primary amino group such as that of aspartame (pKa 7.7) generally has a pKa different from those of the secondary amino group such as that of 1-methyl ester of N- [N- (3,3- dimethylbutyl) -La-aspartyl] -L-phenylalanine (pKa 8.1). In addition, it is known that the pKa of an amino acid has a profound impact on food applications (Labuza, T.P. and Basisier, M.W., 1992, "Physical Chemistry of Foods", H.G.
_M_____f__ Schwartzber and R.W. Hartel (Eds.), Marcel Dekker, Inc., New York). It is also well known that a secondary amine can not form compounds of the Schiff base type with carbonyl compounds while a primary amine can. In addition, N- [N- (3,3-dimethylbutyl) -L-a-aspartyl] -L-phenylalanine-1-methyl ester exhibits a physiologically different behavior than aspartame as exemplified by the dramatic difference in sweetness. These differences are clear indications that the characteristics and properties of one can not suggest those of the other. Although the 1-methyl ester of N-fN - ^. S-dimethylbutyl-J-L-a-aspartyl] -L-phenylalanine is a highly potent sweetener, it is poorly soluble in water and can give rise to problems of dust formation. Therefore, there is a need for 1-methyl N- [N- (3,3-dimethylbutyl) -L-α-aspartyl] -L-phenylalanine derivatives which have good dissolution and solubility properties in aqueous systems and which avoid Dust formation problems often found in fine dusts. It would also be desirable to improve the stability of N- [N- (3,3-dimethylbutyl) -L-a-aspartyl] -L-phenylalanine 1-methyl ester.
BRIEF DESCRIPTION OF THE INVENTION
This invention relates to dipeptide sweeteners which are metal complexes of N- [N- (3,3-dimethylbutyl) -L-a-aspartyl] -L-phenylalanine 1-methyl ester which possess good dissolution and solubility properties in
___! _______ aqueous systems. In particular, the metal complexes of N- [N- (3,3-dimethylbutyl) -L-a-aspartyl] -L-phenylalanine 1-methyl ester of this invention are represented by the formula
wherein Xp + is selected from the group consisting of AI3 +, Fe2 +, Fe3 +, Ca2 +, Mg2 +, and Zn2 +; Yq "is selected from the group consisting of CI", SO42", PO43", HCOO "and CH3COO"; x is a number from 1 to 4 and pn = qm. The invention also relates to a low calorie liquid sweetener containing the metal complexes of this invention.
BRIEF DESCRIPTION OF THE DRAWING
The figure is a graph comparing the aqueous solution of N- [N- (3,3-dimethylbutyl) -L-α-aspartyl] -L-phenylalanine 1-methyl ester in an objective concentration of 0.05% by weight with a concentration of neotame equivalent, that is, the concentration of neotame in each case is the same as the complexes of calcium chloride and zinc sulfate of N-1-methyl ester of N- [N- (3,3-dimethylbutyl) -L- -aspartil ] -L-phenylalanine.
DETAILED DESCRIPTION OF THE INVENTION
This invention is directed to metal complexes of N- [N- (3,3-dimethylbutyl) -L-a-aspartyl] -L-phenylalanine 1-methyl ester, ie metal complexes of neotame. The patents of E.U.A. Nos. 5,480,668, 5,510,508 and 5,728,862, which describe the preparation of N- [N- (3,3-dimethylbutyl) -La-aspartyl] -L-phenylalanine 1-methyl ester are included herein by reference as if they were exposed in their entirety. Therefore, one skilled in the art can easily prepare the starting material without undue experimentation. The metal complexes of this invention can be prepared by adding N- [N- (3,3-dimethylbutyl) -L- -aspartyl] -L-phenylalanine 1-methyl ester and a metal salt to an amount of a solvent effective to dissolve both the N- [N- (3,3-dimethylbutyl) -L-aspartyl] -L-phenylalanine 1-methyl ester and the metal salt, and then stirring for a while to achieve the formation of the metal complex. Suitable solvents include water, methanol, ethanol, sodium propane, butanol, acetone, acetonitrile, tetrahydrofuran, dimethylformamide and dimethyl sulfoxide. The metal complex product can be recovered by evaporating the solvent in vacuo. The metal complex product can also be recovered by freeze drying or spray drying the resulting solution. The metal salts suitable for use in preparing the metal complexes of this invention include any of the salts formed between a metal cation, Xp +, selected from the group consisting of Al3 +, Fe2 +, Fe3 +, Ca2 +, Mg2 + and Zn2 +; and an anion, Yq ~ selected from the group consisting of CI ", SO42", PO43", and CH3COO". These salts will have the formula (Xp +) n (Yq ") m, where pn = qm, to make the salt electrically neutral The complexes of this invention do not need to have a 1-methyl ester ratio of N- [N - (3,3-dimethylbutyl) -L-aspartyl] -L-phenylalanine with respect to the salt of 1: 1, but also include variations thereof Particularly preferred metal complexes of this invention include those formed between calcium chloride, magnesium chloride, ferric chloride, aluminum chloride or zinc sulfate, and N- [N- (3,3-dimethylbutyl) -L-aspartyl] -L-phenylalanine 1-methyl ester. Metals of this invention provide a series of improved properties compared to those of N- [N- (N- (3,3-dimethylbutyl) -L-α-aspartyl] -L-phenylalanine 1-methyl ester.In particular, the aqueous solubility is increased and the dissolution rate of the composition improves a lot, these neotame metal complexes are sweet on the palate. It is also believed that these metal sweetening complexes will have improved stability. Therefore, the metal complexes of N- [N- (3,3-dimethylbutyl) -L- -aspartyl] -L-phenylalanine 1-methyl ester will be particularly useful in beverage systems, particularly because the methods or additional mechanical preparations are reduced or are not necessary to provide a rapid dissolution as desired in a tabletop sweetener.
The metal complexes of this invention can be mixed with known body-forming agents to prepare tablets, powdered sweeteners and granulates using methods well known to those skilled in the art. Another advantage of the metal complexes of this invention is that they do not present the dusting problems related to N- [N- (3,3-dimethylbutyl) -L-a-aspartyl] -L-phenylalanine 1-methyl ester. The metal complexes can also be used to prepare a low calorie liquid sweetener by dissolving a high concentration of the metal complex of this invention in an aqueous or alcoholic system, for example, water, propylene glycol, water / propylene glycol, ethanol or a water / mixture. ethanol. Said low calorie liquid sweetener may find utility in food products such as gelatin desserts, fruit flavored beverages, cereal, cake flour, fruit juices, syrups, salad dressings, pet foods, carbonated soft drinks, tabletop sweeteners and the like. Said utilities are not limited since other applications may include cough medicines, tonics and the like. One embodiment of this invention of particular interest contemplates a liquid tabletop sweetener as a substitute for sucrose and other known sweeteners. The low color liquid sweetener will usually contain up to about 40% by weight of the metal complex of N- [N- (3,3-dimethylbutyl) -La-aspartyl] -L-phenylalanine 1-methyl ester, depending on the concentration , of course, of the final use
MiaMilMIMMta desired. The following examples are intended to illustrate certain preferred embodiments of the invention, and do not imply limitation of the invention.
EXAMPLE 1 Calcium chloride complex of 1-methyl ester of N- | "N- (3,3-dimethylbutyl) -L-a-aspartp-L-phenylalanine
Calcium chloride dihydrate (3.23 g, 0.0220 moles) and 1-methyl ester of N- [N- (3,3-dimethylbutyl) -La-aspartyl] -L-phenylalanine (8.72 g, 0.0220 moles) were dissolved in 80 ml of methanol. Most of the methanol was removed from the resulting clear solution using a rotary evaporator at 33 ° C under vacuum. The solvent residue was removed using a mechanical vacuum pump producing the title complex (11.2 g). This complex (0.2 g) was dissolved in water (100 mL) in less than 120 seconds (visual observation) and 140 seconds (spectrophotometric determination).
EXAMPLE 2 Magnesium chloride complex of N-fN- (3,3-dimethylbutyl) -L-a-aspartyl-L-phenylalanine 1-methyl ester
Magnesium chloride hexahydrate (6.80 g, 0.0334 moles) and 1-methyl ester of N- [N- (3,3-dimethylbutyl) -La-aspartyl] -L-phenylalanine (13.26 g, 0.0334 moles) were dissolved in 100 mL of methanol. Most of the methanol was removed from the resulting clear solution using a rotary evaporator at 33 ° C under vacuum. The solvent residue was removed using a mechanical vacuum pump, yielding the title complex (17.7 g). This complex (0.2 g) was dissolved in water (100 mL) in less than 120 seconds (visual observation).
EXAMPLE 3 N-rN- (3,3-dimethylbutyl) -L-a-aspartyl-L-phenylalanine 1-methyl ester sulfate complex
Zinc heptahydrate (8.86 g, 0.0308 mol) and N- [N- (3,3-dimethylbutyl) -L-aspartyl] -L-phenylalanine 1-methyl ester (12.21 g, 0.0308 mol) were dissolved in 120 ml of methanol. Most of the methanol was removed from the resulting clear solution using a rotary evaporator at 33 ° C under vacuum. The solvent residue was removed using a mechanical vacuum pump, yielding the title complex (17.2 g). This complex (0.2 g) is
_ ___ ¡_h_H____ dissolved in water (100 mL) in less than 140 seconds (visual observation) and 180 seconds (spectrophotometric determination).
COMPARATIVE EXAMPLE 1 Solution of 1-methyl ester of N-rN- (3,3-dimethylbutyl) -L-a-aspartyl-L-phenylalanine in water
N- [N- (3,3-dimethylbutyl) -L-a-aspartyl] -L-phenylalanine 1-methyl ester (0.1-0.2 g) was dissolved in water (100 mL). The compound completely dissolved in 5-8 minutes (visual observation). The dissolution of
1. 0 g of N- [N- (3,3-dimethylbutyl) -L-a-aspartyl] -L-phenylalanine 1-methyl ester in 100 mL of water required approximately 45 minutes. Other variations and modifications of this invention will be obvious to those skilled in the art. This invention should not be limited except by what is disclosed in the following claims.
____________________
Claims (5)
1. - A metal complex of N- [N- (3,3-dimethylbutyl) -L- -aspartyl] -L-phenylalanine 1-methyl ester represented by the formula wherein Xp + is selected from the group consisting of Al3 +, Fe2 +, Fe3 +, Ca2 +, Mg2 + and Zn2 +; Yq "is selected from the group consisting of CI", SO42", PO43" and CH3COO ", x is a number from 1 to 4 and pn = qm 2.- The metal complex according to claim 1, further characterized because (Xp +) n (Yq ") m is calcium chloride, magnesium chloride, ferric chloride, aluminum chloride or zinc sulfate. 3. A low calorie liquid sweetener composition comprising a metal complex of a dipeptide sweetener represented by the formula to you_______ wherein Xp + is selected from the group consisting of Al3 +, Fe2 +, Fe3 +, Ca2 +, Mg2 + and Zn2 +; Yq "is selected from the group consisting of Cl \ SO42 \ PO43" and CH3COO ", x is a number from 1 to 4 and pn = qm, dissolved in a solvent or consumable solvents in a concentration of up to about 40% by weight of the composition for providing a high concentration low calorie liquid sweetener 4. The low calorie liquid sweetener according to claim 3, further characterized in that the solvent is ethanol, propylene glycol, water, ethanol / water or propylene glycol / water. 5. The low-calorie liquid sweetener according to claim 4, further characterized in that (Xp +) n (Yq ") m is calcium chloride, ferric chloride, aluminum chloride, magnesium chloride or zinc sulfate. «! ______________
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60/058,508 | 1997-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA00002552A true MXPA00002552A (en) | 2001-11-21 |
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