Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Noncarbohydrate sweetener or composition containing same
Patent
1986-05-19
1987-12-22
Jones, Raymond N.
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Noncarbohydrate sweetener or composition containing same
426590, 562561, 560169, A23L 1236, A23L 238
Patent
active
047146192
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention relates to new chemical compounds and to methods of using them as dietary sweeteners. In particular the invention also relates to compounds broadly classified as aminomalonyl D-alanine derivatives.
BACKGROUND OF THE INVENTION
Since the introduction of saccharin as an artificial sweetener, relative few new sweeteners have been developed. Among those that have been discovered, however, chief among them is the methyl ester of L-.alpha.-Aspartyl-L-phenylalanine, more commonly known as aspartame, disclosed in U.S. Pat. No. 3,492,131 to Schlatter. The viability of aspartame's use in non-dry applications is in serious question, however. Its recent introduction for use in soft drinks in this country was as a mixture with saccharin, the saccharin being used to maintain a sweet taste long after aspartame hydrolyzes to a non-sweet structure.
Thus, a non-toxic artificial sweetener compound comparable in sweetening ability to aspartame but which exhibits superior stability to aspartame in aqueous media would be a useful addition to the artificial sweeteners industry. Such compounds, compositions containing them, and methods of using these compounds as artificial sweeteners are the subject of the present invention.
Japanese Pat. No. 28068 (Takeda) describes aminomalonyl dipeptides which have a C-terminal amino acid of the L-configuration as sweetening compounds for preparing food. Surprisingly, we have found that such is not the case, but rather that the corresponding compounds of the present invention having a C-terminal amino acid of the D-configuration are sweet.
SUMMARY OF THE INVENTION
The present invention provides compounds useful as artificial sweeteners having the following structure: ##STR2## wherein X or --OR or --NHR, R being alkyl of 3-10 carbon atoms, or --NH.sub.2. A preferred embodiment results when X or --OR and R is an isopropyl group, i.e. the isopropyl ester of aminomalonyl-D-alanine (herein also referred to simply as the "isopropyl ester"). Stereochemically, when synthesized the compounds of the present invention result as diastereomeric mixtures. The above formula is shown for convenience but it should be noted that the compounds will likely exist as zwitterions.
The pharmaceutically acceptable salts, such as the citrate, tartrate, hydrochloride, and phosphate, of the compounds disclosed herein are also effective as sweeteners. Such salts can be made using typical acids and procedures for making the salts are as conventionally known and practiced in the art.
The compounds of this invention generally range in sweetness between that of sucrose and aspartame. For example, the isopropyl ester of aminomalonyl alanine is 58 times sweeter than sucrose and about half as sweet as aspartame on a weight basis. Compared to saccharin, the isopropyl ester does not possess a "metallic" aftertaste, and there are virtually no detracting side tastes.
Additionally, the compound of this invention are believed to be non-toxic. Concerns have been raised regarding the principal metabolism products of aspartame--aspartic acid and phenylalanine. The former causes brain lesions in neonatal mice and the latter has been reported to induce grand mal-type seizures in monkeys, produce birth defects in pregnant women with phenylketonuria, induce behavioral changes, and alter brain chemistry. Saccharin itself is well known as a weak mutagen in the Ames assay, a property which is associated with carcinogenic potential.
In addition to the compounds having the structure given above, the invention also provides a method of sweetening a beverage, comprising dissolving a sufficient amount of at least one of the compounds disclosed herein to effect said sweetening.
It is therefore an object of this invention to provide an artificial sweetener.
It is further an object of this invention to provide an artificial sweetener which is relatively stable in aqueous solution.
It is further an object of this invention to provide an artificial sweetener which is non-toxic.
These and other objects and adva
REFERENCES:
patent: 4564548 (1986-01-01), Seltzmann
Hsieh Yung-Ao
Seltzman Herbert H.
Jones Raymond N.
Paden Carolyn
Research Triangle Institute
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