DE2022499B2 - Use of dipeptides - Google Patents

Description

COH

Il
ο

C-H

CH ₂ CH ₂

CH ₂ CH ₂
CH
R.

in which R is a hydrogen atom or the hydroxyl group means and the stereochemical configuration is L-L, DL-DL, DL-L or L-Dl, as an active ingredient for sweetening edible substances, optionally together with known sweeteners, thereby characterized in that the dipeptide is L-asparaginyl-L-phenylalanine methyl ester used with saccharin, cyclamate or sucrose as well-known sweeteners

2. Use according to claim 1, characterized in that tablets are used which as active ingredients 25 mg L-asparaginyl-L-phenylalanine methyl ester and contain 4 mg of saccharin.

3. Use according to claim 2, characterized in that tablets are used which contain a solid, non-toxic carrier for the sweeteners.

Use of dipeptides of the general formula O O

Il Il

H;, N-CH-C-NH-CH-C-OCH ₃
CH ₂ CH ₂

I I

COH C-H

II / \

O CH ₂ CH ₂

CH ₂ CH ₂
CH
R.

in which R denotes a hydrogen atom or the hydroxyl group and the stereochemical configuration L-L, DL-DL, DL-L or L-Dl is, as an active ingredient for sweetening edible substances, optionally together with known sweeteners.

Patent 19 36159 emphasizes that the joint use of a compound of the formula given above with a known sweetener such as Saccharin, or cyclamate, to a surprising one

Increase in sweetness leads

The subject of the invention is the further development of the subject of the main patent shown in the preceding claims.
The production of the dipeptides to be used according to the invention is described in DE-AS16 92 768.

Compositions which contain saccharine and L-asparaginyl-L-phenylalanine methyl ester are particularly advantageous.
L-asparaginyl-L-phenyl-analine-methyl ester has a sweetness which is 125 to 150 times the sweetness of sugar

The compositions for use in the present invention can take a variety of forms which are suitable for use as a sweetener. Typical shapes that can be used are: solid forms such as powder, tablets, granules and dragees; liquid forms, such as solutions, suspensions, Syrups and emulsions, as well as other commonly used forms that can be combined with edible materials are particularly suitable. The present one The term "edible materials" used refers to all non-toxic materials that are in solid or liquid form can be consumed or ingested by humans and animals. Examples of such Materials are: food and feed, pre-made food and feed ingredients, chewing gum, Drinking liquids, food and feed additives, including flavorings and colorings and the Taste enhancing or improving agents and protected and unprotected pharmaceuticals Preparations.

The compositions to be used according to the invention can be processed into preparations which may be present separately or in conjunction with non-toxic sweetener carriers, d. H. non-toxic Carriers for sweeteners, i.e. non-toxic substances as they are usually found in Used in conjunction with sweeteners. Such carriers include liquids such as water, ethanol, Sorbitol glycerin, citric acid, corn oil, peanut oil, soybean oil, sesame oil, propylene glycol, corn syrup, maple syrup and liquid paraffin as well as modified solids such as lactose, cellulose, starch, dextrin and others Starches, calcium phosphate, and D- and tricalcium phosphate. Cannot be used with these compositions are naturally toxic carriers such as methanol and dimethyl sulfoxide.

Examples of specific edible materials to be used with the compositions of the present invention Can be sweetened are: fruits, vegetables, juices; Meat products such as ham, bacon, sausages; Egg products; Fruit concentrates; Gelatin, gelatinous products such as jams, jellies, preserves; Dairy products such as ice cream, sour cream, and sherbet; Glazes; Syrups, including molasses; Corn-, Wheat, rye, soybean, adhesive and rice products such as bread, corn flakes, pasta and cake mixes; Fish, seafood and seafood; Cheese and cheese products; Nut kernels and nut products; Beverages,

μ like coffee, tea, non-carbonated and carbonated soft drinks, beers, wines; Confections, such as candies and fruit drops; Seasoning like herbs and spices; Vinegar; flavor enhancing substance

zen, such as sodium glutamate, also chewing gum Further examples of commercial products in which the invention Compositions to be used that can be used are: packaged products, such as Diet sugar, liquid sweeteners, granulated flavor mixtures, which result in non-carbonated drinks when water is added, instant pudding powder, Instant coffee and tea, coffee brighteners, malt-milk mixtures, Feed for pets and livestock; Tobacco, diet supplements and consumable toilet articles, such as mouthwashes and toothpastes, as well as pharmaceutical ones Preparations where there is a need for diabetic or other dietary requirements have caused.

The sweetness of saccharin, depending on the edible material to which it is added, is about this 500 times the sweetness of sucrose. Surprisingly, it was found that the sweetness of Saccharin is enhanced significantly when you use it mixed with the dipepiid to be used according to the invention. The addition of L-asparaginyl-L-phenylalanine methyl ester increases the sweetness of saccharin to around 1000.

A tablet which contains the composition according to the invention and which is explained below is explained below for addition to edible material, e.g. B. coffee is suitable

Components lot Asparaginyl-L-phenylalanine- methyl ester 25 mg Saccharin 4 mg Mannitol 200 mg Sorbitol 5 mg Magnesium stearate 1 mg

The following are specific examples of the synergistic effect produced by mixing the described Dipeptides are made with a known sweetener.

example 1

Using four different sweetener compositions: A) sucrose alone, B) L-asparaginyl-L-phenylalanine methyl ester alone, C) saccharin alone and D) saccharin and L-asparaginyl-L-phenylalanine methyl ester A non-carbonated artificial strawberry drink was made The composition of the four different beverages, each accounting for 300 ml, are given below.

Q saccharin alone Saccharin 0.054 g Citric acid 0.15 g

Lactose 1.827 g

artificial strawberry flavor 0.12 g

Water 299 g

D. Saccharin plus L-asparaginyl-L-phenylalanine methyl ester

L-asparaginyl-L-phenylalanine-

methyl ester 0.108 g

Citric acid 0.15 g Final volume of lactose 1.827 g Saccharin 0.0165 g

artificial strawberry flavor 0.12 g

By comparing tastes, it was found that each of the four beverages had the same degree of sweetness would have.

Example 2

Dissolving 16.5 g of instant coffee powder in 3000 ml of water made about 3000 ml of instant coffee 4 portions of 600 ml each were taken from this. Each became one of the following Sweetener preparations given: E) 24 g sucrose, F) 0.16 g L-Aspai-aginyl-L-phenylalanine-methytestcr, G) 0.048 g saccharin and H) 0.012 g saccharin and 0.08 g L-asparaginyl-L-phenylalanine methyl ester.

By comparing tastes, it was found that each of the sweetened coffee samples had the same sweetness Had taste.

Example 3

A kola drink was made by first making the following raw material:

140.8 ml kola concentrate
2.72 g sodium benzoate

18.85 g of a mixture of 1 part by weight of La-asparaginyl-L-phenylalanine methyl ester and 10 parts by weight of sodium cyclamate
Water to make up to a final volume of 1300 ml.

r Γ
C. A. sucrose alone 27 g 0.216 g f. Sucrose 2.61g 0.15 g * 1 Dextrose 0.15 g 0.12 g I.
( citric acid 0.12 g 1.827 g r artificial strawberry flavor 1.827 g 299 g Lactose 268 g water B. L-asparaginyl-L-phenylalanine methyl ester alone L-asparaginyl-L-phenylalanine- methyl ester citric acid artificial strawberry flavor Lactose water

Each bottle of the drink was refilled by adding 29.6 ml of this base with soie! carbonated water diluted to a final volume of 178 ml with a carbonated volume of 3.6 was created.

Example 4

A cola drink was made by first produced the following raw material:

140.8 ml kola concentrate
2.72 g sodium benzoate

16.72 g of a mixture of 1 part by weight of L - «- asparaginyl-L-phenylalanine methyl ester and 7 parts by weight of sodium cyclamate
Water to make up to a final volume of 1300 ml.

Each bottle of this drink was refilled by one 29.6 ml of this base is diluted with so much carbonated water that a final volume of 178 ml with a carbonic acid volume of 3.6 was created.

Example 5

An orange soda was made by first making the following raw material:

63.0 ml orange base

17.0 ml of 50% citric acid

14.5 ml of 25% sodium benzoate 21.41 g of a mixture of 1 part by weight of L-α-asparaginyl-L-phenylalanine methyl ester and 10 wt.

Share sodium cyclamate
Water to conspire to a final volume of 125OmL

Each bottle of this drink was refilled by you diluted 28.5 ml of this base with so much carbonated water that a final volume of 178 ml with a carbonic acid volume of 1.75 was created.

Example 6

An orange soda was made by first produced the following raw material:

is 63.0 ml orange base

17.0 ml of 50% citric acid

14.5 ml of 25% sodium benzoate

18.99 g of a mixture of 1 part by weight of L-oc-asparaginyl-L-phenylalanine methyl ester and 7 wt.

Share sodium cyclamate

Water to make up to a total volume of
125OmL

Each bottle of this drink was refilled by one 29.5 ml of this basic material with so much carbonic acid Water diluted to a final volume of 178 ml with a final carbonic acid volume of 1.75 originated.

The exploitation of the invention can be made possible by legal provisions, in particular by the Food Act, be limited.

Claims (1)

Patent claims: I. Further development of the subject matter of patent 19 36 159.2 relating to the use of Dipeptides of the general formula O O Il Il H ₂ N-CH-C-NH-CH-C-OCH ₃
CH ₂ CH ₂