DE2700036B2 - Process for sweetening digestible products and non-digestible products to be ingested and the products as such manufactured according to this process - Google Patents

Description

HO

30th

35

brings in wherein

R ^{1 represents} a hydroxyl group or a chlorine atom;

R ² and R ³ each represent a hydroxy group and a hydrogen atom, a chlorine atom and a hydrogen atom, or a hydrogen atom and a chlorine atom, the 4-position being in the D configuration;

R ^{4 represents} a hydroxy group; or when at least two of the R ¹ , R ² , R ³ and R ⁵ groups represent chlorine atoms, R ^{4 represents} a hydroxyl group or a chlorine atom; and

R ^{5 represents} a hydroxyl group; or, if at least one of the R ¹ , R ² and R ³ groups represents a chlorine atom, R ^{5 represents} a hydroxyl group or a chlorine atom; with the proviso that at least one of R ¹ , R ² , R ³ and R ^{5 is} a chlorine atom

2. The method according to claim 1, characterized in that in the compound of formula (I) R ^{1 represents} a chlorine atom

3. The method according to claim 1 or 2, characterized in that there is a connection of the form! (I)

1. 1'-chloro-l'-deoxysucrose;

2. 4-chloro-4-deoxy - «- D-galactopyranosylJ-D-fructofuranoside;

3. ^ ChloM-deoxy-flc-D-galactopyranosyl-1-chloro-1-deoxy-β-D-fnictofuranoside;

4. r.e'-dichloro-l'.e'-dideoxysucrose;

5. ^ ChloM-deoxy-Ä-D-galactopyranosyl, 6-dich] or-1,6-dideoxy - /) - D-fructofuranoside;

6. 4,6-dichloro-4,6-dideoxy - «- D-galactpyranosyl-6-chloro-6-deoxy - /? - D-fructofuranoside;

7. 6,1 ', 6' -trichloro-6,1 ', o'-trideoxysucrose;

8. 4,6-pichlor-4,6-dideoxy - «- D-galactopyranosyl, 6-dichloro-1,6-dideoxy-0-D-fructofuranoside, and or

9. 4,6,1 ', 6'-tetrachlor ~ 4,6, l', 6'-tetradeoxysucrose

brings in

4. Sweetened digestible products or sweetened, ingestible, non-digestible products Products, characterized in that a compound of the above formula (I) has been added to them is

5. Product according to claim 4, characterized in that in the compound of formula (I) R ^{1 represents} a chlorine atom

6. Sweetened digestible products or sweetened, ingestible, non-digestible products Products, characterized in that they contain one of the compounds 1 to 9 according to Claim 3 has been added

7. Sweetened products according to claim 4 in the form of a liquid, characterized in that them

such a common additive has been added to improve the so-called mouthfeel

A “digestible product” is used to describe those products which, with the usual course intended to be swallowed during use, for example a food or drink or an oral one pharmaceutical preparation to be administered. The term "oral agent" is used to denote an agent which, in the normal course of use, does not intended to be digested as such, but used in the mouth to treat the throat or oral cavity is, for example, a toothpaste, tooth powder, mouthwash liquid, gargle, lozenge, tooth lotion or chewing gum. The term "sweeteners" means agents that are not taken orally themselves either for digestion or in the mouth be held, but instead others Digestible products or oral products should be added to keep them sweet Increase EU.

27 OO

While sucrose is still the most widely used sweetener, there are many Attempts have been made to find substantially sweeter alternatives which could then be used when desired, a high one Degree of SQBe with a low calorie content and / or a low risk of dental caries, for example for dietetic products or for the Combine manufacture of soft drinks. We have two most successful sweeteners based on non-sac- to Charose base (i.e., sweeteners that comprise a substance other than sarcharose) are so far Saccharin and Cydamate have been, each about 200 and about 30 times the sweetness of sucrose exhibit. However, recent use of these sweeteners, particularly cydamate, has been in some Relief has been restricted or banned, ds doubts about their safety have arisen. Saccharin also has the disadvantage of an uncomfortably bitter aftertaste that is felt by many people is detectable

Recently, many other non-sucrose based sweeteners have been investigated, some of natural origin and others of synthetic origin, with A wide range of chemical structures has been captured. These compounds have proteins such as Monellin, thaumatin and miraculin, dipeptides, such as However, includes asarbyl-L-phenylalanine methyl ester, and dihydrochalcones such as neohesperidine dihydrochalcone apart from the difficulties in synthesizing or extracting such sweeteners, they do not have them necessarily the same sweetness quality as sucrose: especially when compared to sucrose, the Sweetness start relatively slowly and linger on relatively, whereby a licorice-like or other aftertaste may be present, which is the sweetener as one makes a direct substitute for sucrose unsuitable if these differences are not masked can.

Although numerous sweeteners with very different chemical structures are now being investigated it is important to note that a sweetness exceeding that of sucrose in no sucrose derivative or other carbohydrate has been discovered: in those cases where an intensely sweet substance has been discovered such as saccharin, cyclamate and the others Non-sucrose-based sweeteners, which have already been mentioned, have always been of different structure strongly different from sucrose. Indeed, it is so well known that the presence of some substituents on can destroy the sweetness of the sucrose molecule and give it a bitter taste itself.

It is therefore extremely surprising and in complete contrast to what is known about so far Non-sucrose based sweeteners that have now been determined according to the invention that certain Derivatives of sucrose and a sucrose isomer are much sweeter than sucrose itself, with whose sweetness is comparable in intensity to that of saccharin, and a quality to that of Sucrose is comparable, is present

The subject matter of the invention is thus that shown in the preceding claims 1 to 3 Process can sweeten digestive products and ingestible, non-digestible products Products as well as the products produced according to this process as such, according to claims 4 to 7.

The compounds of formula (I) can be used as sweeteners in any conventional manner including sweetening "Digestible products" (as defined above), for example food, beverages and orally administered pharmaceutical preparations and "Oral Mitteta" (according to above definition) for example toothpastes, chewing gum and mouthwashes. You can also use conventional liquid or with solid extenders and carriers in "sweeteners" (according to above definition) can be used.

The diluent or carrier comprises any suitable vehicle for the sucrose derivative of general formula (I) so that it can be formulated in a composition which is convenient for sweetening other products can be used, for example as granules, tablets or in drop form. That Thus, for example, the diluent or the carrier can be conventional water-dispersible tableting ingredients such as starch, lactose and sucrose itself, included. The extender or carrier Can also use low density bulking agents to create a granular sweetener with one to that of Sucrose equivalent sweetness per unit volume, for example spray-dried maltodextrins, include, while aqueous solutions contain auxiliaries such as stabilizers, colorants and viscosity adjusters

Beverages, e.g. non-alcoholic beverages that contain a sucrose derivative of the general formula (I), can either be used as sugar-free dietetic products or as "reduced sugar content" products be formulated containing the minimum amount of sugar required by law. In the absence of sugar it is desirable to have additional substances add to create a "mouthfeel" similar to that obtained from sugar, for example pectin or vegetable gum. For example, pectin can be added in an amount of 0.1 to 0.15% can be added to a bottle of syrup.

A number of compounds of general formula (I) which are used according to the invention are shown in the table below

Table 1

CH ₂ R ⁴

,O

CH ₃ R ¹

HO

(D

HO H R ¹ OH O R ³ R " Ί — r
OH H CH ₂ R ⁵
6 ' Connecting
application no. CI R ² H OH R ⁵ Approximate sweetness
(X sucrose) *) 1 OH OH Cl OH OH 20th 2 Cl H Cl OH OH 5 3 CI H H OH OH 600 4th Cl OH Cl OH CI 500 5 OH H Cl Cl Cl 2000 6th Cl H H Cl Cl 4th 7th Cl OH Cl Cl Cl 100 3 Cl H H Cl Cl 200 9 Cl Cl 100

*) Sweetness rating

The SuBe is in aqueous solution by comparison with a 10 wt .-% aqueous solution of Sucrose rated The results were obtained by a small test group and are therefore not statistically exact, but reflect the approximate order of magnitude of the sweetness.

The compounds in Table 1 are as follows (the systematic nomenclature is given first, according to which the common name is based on "galactosaccharose" in those cases where there is a 4-chloro substituent present):

1. l'-chloro-l'-deoxysucrose

2. 4-Chk> r-4-deoxy-Ä-D-galactopyranosylß-D-fructofuranoside

(i.e. 4-ChloM-deoxygalactosucrose)

3. 4-Chloro-4-deoxy- «- D-galactopyranosyl-1-chloro-1-deoxy-0-D-fructofuranoside

(i.e. 4, r-dichloro-4, l'-dideoxygalactosucrose)

4. l ', 6'-dichloro r ^ -dideoxy sucrose

5. 4-chloro-4- <ieoxy- "- D-galactopyranosyll, 6-dkAk> r-1,6-dideoxy-0-D-fructofuranoside (i.e. ^ l'.e'-TrichloM.l'.e'-trideoxygalactosucrose)

6. 4,6-dichloro-4,6-dideoxy- <x -D-galactopyranosyl-6-chk > r-6-deoxy - /> - D-fructofuranoside

(i.e. 4Aß'-TrichloM, 6,6'-trideoxygalactosucrose)

7. 6,1 ', 6'-trichloro-6, l', 6'-tridcoxysaccharose)

8. 4,6-dichloro-4,6-dideoxy - «- D-galactopyranosyl, 6-dichloro-1,6-dideoxy- / 3-D-fructoniranoside (i.e. 4,6,1 ', 6'-tetr «chloro-4,6,1', 6'-tetradeoxygalactosucrose)

9. 4,6, l ', 6'-tetrachloro-4,6, r, 6'-tetradeoxysucrose

From Table 1 it can be seen that the chlorine substituents in the Λ, Y and 6 'positions are effective to induce sweetness. A combination of the two such substituents is synergistic and increased in value in general, the sweetness by an order of magnitude compared to the simply additive increase. Thus results for example an 1'-chlorine substituent itself has a sweetness of 2Ox and a 4j3-chlorine substituent itself a sweetness from 4 χ. However, a 4, r-dichloro combination results a sweetness of 60Ox and a 1 ', 6' poet combination results in a sweetness of 50Ox. In a similar way a combination of all three chlorine substituents increases the sweetness by almost a further order of magnitude, with the 4, r, 6'-trichloro derivative having a sweetness of 2000 χ (all sweetnesses are expressed as multiples of sucrose)

In contrast, a 6-chloro substituent is disadvantageous and has the effect of reducing the SQBe by antagonizing the action of the other

so substituents. For this reason, a 6-chloro substituent R ⁴ can only be present in formula (I) if at least two other chlorine substituents are present.

In general, the 6-chloro-substituted compounds are not preferred for this reason - the sweetest compounds contain 4,1'- and 6'-chlorine substituents a

The pronounced SDBe of the compounds of the formula (I) is combined with an LD ₅₀ (50% lethal dose) value, which in the case of compound 5 is shown in Table 1 for example above 16 g / kg in mice, which is the represents the largest dose that can be administered in practice.

Most of the compounds of the general formula (1) are known and can be synthetic which are described in the chemical literature. However, none of the known compounds has previously been recognized as having possess some useful sweetness.

Compound 5 is in carbohydrate. Res. 40, (1975), 285; Compound 6 in carbohydrate. Res., 44, (1975) 37 and Compound 7 in carbohydrate. Res., 25, (1972), 504 and ibid 44, (1975), 12-13. Compound 2 is in carbohydrate. Res., 40, (1975), 285-298.

All compounds of the general formula (I), both the new and the old, can through Reaction of a sucrose ester containing free hydroxyl groups in the parts to be chlorinated with Sulfuryl chloride can be generated to obtain the corresponding chlorine in sulfate derivative. This results in Treatment with a source of chloride ions such as lithium chloride in an amide solvent such as hexamethylphosphoric acid triamide, the chlorinated sucrose esters. The hydrolysis of the chloroesters, e.g. B. under ι ί Using sodium methylate in dry methanol then sets in the free chlorosucrose Freedom. The reaction with sulfuryl chloride is conveniently carried out at a reduced temperature in one Inert solvent in the presence of a base, e.g. B. chloroform containing pyridine carried out.

A similar methodology can be used for the further chlorination of an already chlorinated sucrose derivative can be applied.

In general, the 4-chloro-sucrose derivatives can be prepared by reacting the 4-chloro-galactosucrose analog with a source of chloride ions at an elevated temperature, e.g. B. 100 to 150 ⁰ C, preferably in the presence of a catalytic amount of iodine obtained.

The following examples 1 to 4 illustrate the production of the not protected here compounds to be used according to the invention and Examples 5 to 10 describe the invention as such (the Temperatures are given in ° C). J5

example 1

1'-chloro-1'-deoxysucrose (compound 1)
(a) 1'-chloro-1'-deoxysaccharose hepta-acetate

A solution of 2,3,4,6,3 ', 4', 6'-hepta-O-acetyIsaccharose (2 g) in a mixture of pyridine (10 ml) and chloroform (30 ml) was treated with sulfuryl chloride (2 ml ) treated at -75 ° C. for 45 minutes. The reaction mixture was taken up in ice-cold sulfuric acid (10%, 200 ml) and dichloromethane (200 ml) and shaken vigorously. The organic layer was then washed successively with water, aqueous sodium hydrogen carbonate and water and then dried (Na 2 SC> 4). The solution was concentrated and extracted with ether. The insoluble material was filtered off and the filtrate was concentrated to give the corresponding 1'-chlorosulfate derivative (2.1g)

This syrupy residue (2 g) was then treated with lithium chloride (2 g) in hexamethylphosphoric triamide (HMPA) (10 ml) at 90 ^° C. for 24 hours. The reaction mixture was poured into ice water and the precipitate formed was collected, washed with water and in ether recorded. The organic layer was dried over sodium sulfate, concentrated and eluted from a silica gel column with ether-light petroleum (1: 1) to give the l'-chloroheptaacetate as an amorphous powder [α] ο + 55.0 ° (c 1.2, CHCl3) ; NMR data: τ 4.29 (d, Ju 3.5 Hz, HI); 5.11 (dd, J ₁₃ 10.0 Hz, H-2); 4.56 (t, J3.4 9.5 Hz, H-3); 4.94 (t. Uj ₅ 94 Hz, H-4); 432 (d, J ,,. 6.5 Hz. H-3 '); 4.60 (t, Us 63 Hz, H-4); 7.84-8.01 (7 Ac). Data of the mass spec

55 trums: [(a) denotes ions which are due to the hexa-pyranosyl cation and (b) a 3: 1 doublet (1 Cl) which is due to ketofuranosyl]: m / e 331 a, 307b, 187 b, 169 a, 145 b, 109 a.

Analysis for C26H35CIO17:

calculated C 47.7, H 5.4, Cl 5.4%,
found C 47.5, H 5.6, Cl 5.7%.

(b) 1'-chloro-1'-deoxysucrose

A solution of the above intermediate (1 g) in dry methanol (10 ml) was treated with a catalytic amount of 1 M sodium methylate in methanol at room temperature for 5 hours. A slowly moving product was detected by thin layer chromatography (dichloromethane-methanol 3: 1). The solution was deionized by shaking with Amberlyst-15 (a polystyrene sulfonic acid resin) in the H ⁺ form, concentrated, and purified by shaking an aqueous solution of the syrup with petroleum ether. The aqueous layer was then concentrated and dried under vacuum to give r-chloro-1'-deoxysucrose [<x] _D + 57.8 ° (c 0.7, water).

Analysis for C12H21CIO10:

calculated C 39.9, H 5.9, Cl 9.8%,
found C 39.7, H 6.1, Cl 9.7%.

Example 2

4,1'-dichloro-4,1 '-dideoxygalactosucrose
(Connection 3)

(a) 2,3,6-Tri-O-acetyl-4-chloro-4-deoxy-

a-D-galactopyranosyl-S ^ -di-O-acetyl-e-O-benzene-

1 -chlor-1 -deoxysucrose

A solution of 2,3,6,3 ', 4'-Penta-O-acetyI-6'-O-benzoylsucrose (2 g) in a mixture of pyridine (10 ml) and chloroform (30 ml) was treated with sulfuryl chloride ( 2 ml) treated at -75 ° for 45 minutes. The reaction mixture was poured into ice-cold sulfuric acid (10%, 200 ml) with vigorous shaking and then extracted with dichloromethane. The organic layer was washed successively with water, aqueous sodium hydrogen carbonate and water and dried (Na 2 SC> 4). The solution was concentrated and extracted with ether. The insoluble material was filtered off and the filtrate was concentrated to give the chlorosulfate (2.1 g). This intermediate was then treated with lithium chloride as in Example 1 to give the chlorine intermediate identified above.

(b) 4-Chloro-4-deoxy-a-D-galactopyranosyl-1-chloro-1-deoxy-jJ-D-fructofuranoside

A solution of the above intermediate from (a) (1 g) in dry methanol was obtained with a catalytic amount of 1M sodium methylate in methanol at room temperature for 5 hours A product was obtained by thin layer chromatography (dichloromethane-methanol 4: 1). The reaction was worked up as in Example 1 (b) to give the title compound as a syrup, [<%] d + 49.6 ° (c, 0.7, Water).

65

Analysis for Ci ₂ H ₂₀ Cl ₂ O ₉ :

calculated C 38.0, H 53, Cl 18.7% found C 35.7, H 6.0, α 20.4%.

Using a similar methodology, l ', 6'-dichloro, 6'-dideoxysucrose (compound 4) was prepared: [a] _D + 67 ° (c 1.0, methanol)

Analysis for C12H20CI2O9:

calculated C 38.0, H 5.3, Cl 18.7%,
found C 37.7, H 5.2, Cl 17.1%.

Hexaacetate - white solid foam, [a] o + 51.7 ° (cl3, CHCh), mass spectrometry: m / e 331 and 283 (2 Cl). Characterized by reductive dehalogenation with Raney nickel, H2 and KOH to l ', 6'-dideoxysucrose hexaacetate - a thick, colorless syrup; Wd + 25.5 ° (c 1.0, CHCl ₃ ). 100 Hz NMR (C ₆ D ₆ τ values) - HI, 4.36 c / (J, 2 3.5 Hz); H-2, 4.99 <7 (J ₂ , 3 10.5 Hz); H-3, 4.17, '(Jj,! 0.0 Hz); H-4, 4.7! J (J ₄₃ ! 0.0 Hz); H-I ', 8.58 S; H-6'- 8.60 d

Example 3

4,6- dichloro-4,6-dideoxy- <x- D-galactopyranosyl-

1,6-dichloro-1,6-dideoxy-j3-D-fructofuranoside

(Connection 8)

A solution of ö.r.ö'-trichloro-ö.r.ö'-trideoxysaccharose (3 g) in pyridine (70 ml) was mixed with sulfuryl chloride (35 ml) in dry chloroform (100 ml) Treated -75 ° C for 3 hours. The solution was at 0 to -5 ° C for 2 hours and then stirred at room temperature for 24 hours. The reaction mixture was then washed with dichloromethane (100 ml) and diluted successively with ice-cold sulfuric acid (10%, 250 ml), water, aqueous sodium hydrogen carbonate and washed water. The organic layer was dried over sodium sulfate and taken under Receiving a concentrated syrup. The syrupy residue was dissolved in methanol (100 ml) and dried using excess barium carbonate and a catalytic amount of sodium iodide are dechlorosulphated. Of the inorganic residue was filtered off and the filtrate concentrated to a syrup. By thin layer chromatography (Chloroform-methanol 4: 1) gave 4,6,1 ', ö'-tetrachloro ^ .e.r.ö'-tetradeoxy-galactosucrose as the main product. A fast moving, low content product, possibly a pentachloro derivative, was also found under purification on a silica gel column Use of chloroform-acetone (5: 1) gave the tetrachloro derivative in 90% yield.

Exactly equivalent results were obtained by repeating the above method, but starting from r.e'-dichloro-r.ö'-dideoxysaccharose or l'-chloro-1'-deoxysucrose instead of 6,1 ', 6'-TrIChIOr-O ₁ I ', 6'-trideoxysucrose obtained.

[«] D + 89 ° (dft. Methanol). Mass spectroscopy: m / e 199 (2-Cl).

Tetraacetate - white solid foam, [ä] d + 98.5 ^o (fc 1.0, CHCl 3), 100 MHz, NMR (CDCl ₃ · v values) 4.28 d (HI), 5.25 q (H. -4), 4.30 d (H-3 '), 4.55 t {HA ¹ ) J _u 3.5 Hz; J3.4 3.0 Hz; J _4-5 1.5 Hz; J3.4 x 6.5 Hz; J ₄ ^ _-5 - 6.5 Hz; Mass spectrometry: m / e 283 (2 Cl).

Tetramesylate - very pale yellow crystals from dichloromethane-ethanol; Melting point 120-121 °; [<x] d + 65.5 ^o (c 1.0, CHCl 3). 100 MHz NMR (CDCl ₃ , T values) HI 4.18 d (J _1-2 3.5 Hz); H-2 5.06 9 (J ₂₃ 10 Hz); H-3 4.77 9 (J _3-4 3.5 Hz); H-4 5.20 ₉ (J _4-5 1.5 Hz); H-3'4.39 d (J _3-4 -7.0 Hz); H-4'4, (55 i (J ₄ v>, 7.0 Hz); mass spectrometry: m / e 355 (2 Cl).

Example 4

4,6,1 ', 6'-tetrachloro-4,6, l', ö'-tetradeoxysucrose
(Compound 9)

To a solution of 4,6,6'-trichloro-4,6,6'-trideoxy-2,3,3 ', 4'-tetra-O-acetylgalactosucrose 1'-O-monomesitylene sulfonate (Ig) in dimethylformamide (15 ml) an excess of lithium chloride (2 g) and a catalytic amount of iodine (50 mg) were added and

ι "the mixture was heated to 140 to 145 ° in an oil bath heated for 18 hours. Thin layer chromatography (benzene-ethyl acetate 3: 1) revealed the Presence of a major product that migrated faster from the starting material. The reaction mixture

is was cooled, poured into ice cold water and then extracted with ethyl acetate. The organic extract was washed thoroughly, initially with 5% sodium thiosulfate solution and then with water and then dried. The ethyl acetate was evaporated and the residue treated with methanol, which is a catalytic amount of sodium methylate contained.

The thin-layer chromatogram (chloroform / acetone / methanol / water, 57: 20: 20: 3) now showed the presence of a faster moving product in smaller quantities and a slower moving main product - both of which had very similar mobilities, the latter being 4.6 , 1 '-6,' - tetradeoxy-galactosucrose (compound 8) (mixed thin layer chromatogram). The mixture was fractionated on a silica gel column using chloroform-methanol (10: 1) as the eluant. However, complete separation was not achieved because of the closely spaced mobilities of the two components. The first few fractions contained 4,6,1 ', 6'-tetrachloro-4,6, l', 6'-tetradeoxy-sucrose, which as a white solid [<x] d + 45 ° (c \ ß, MeOH) was obtained. The structure was confirmed by NMR and mass spectrometry of the following derivatives:

Tetraacetate syrup, [λ] _ο + 30.5 ° fc 1.0, CHCl ₃ ) NMR (C ₆ D ₆ r values) - HI, 4.39 c / (Ji, ₂ 4.35 Hz); H-2. 5.14 q (J ₂₃ 10 Hz); H-3, 4.27 f (J ₃₄ 10 Hz); H-4 6.1 t (J ^ 10 Hz); H-3 ', 4.20 d (] y, A- 9.6 Hz); H-4', 4.62 r (J ₄ .5 x 6.0 Hz).

Tetramesylate - white crystalline compound, melting point 187 ° (dichloromethane-methanol) [a] _D + 29.9 ° (t 1.0, acetone).

Example 5
Sweet tablets for beverages

Each tablet contains:

Connection 3
or connection 5

8 mg
2 mg

together with a dispersible tablet base (approx. 60 mg) the sucrose, gum arabic and Magnesium stearate contains and is equivalent to about 4.5 g of sucrose in terms of sweetness.

Example 6
Filled sweetener

A filled sweetener that is the same

<> 5 sweetness as an equivalent volume of sucrose (granulated sugar) is obtained by mixing

of the following ingredients and spray drying to a bulk density of 0.2 g / cm ³ :

Maltodextrin solution with a dry weight of
containing compound 3
(or connection 5

222.2 g 1.7 g 0.5 g)

The resulting composition has a sweetness equivalent to about 2 kg of sugar.

Example 7

Cola drink containing sugar with reduced calorie content.

Ingredients for making 100 ml bottle syrup:

Connection 3

(or connection 5

sugar

Benzoic acid

Phosphoric acid (conc.)

Kola flavor

colour

Make up to 100 ml with

Mineral water

80 mg 20 mg) 60 g 35 mg 1 ml 1.1 ml ad-lib.

This syrup can then be added in 25 ml cans with CO2-displaced 255 ml portions of chilled mineral water to be added.

Example 8

Low-calorie carbonated soda pop (sugar-free)

Ingredients for making 100 ml of syrup:

This syrup can be added in 25 ml cans to 225 ml portions with CO2 added to chilled mineral water will.

Example 9

Toothpaste

Weight o / o

Dibasic calcium phosphate 50%

Glycerine 20% Sodium Lauryl Sulphate 2.5%

Spearmint Oil 2.5%

Tragacanth gum 1.0%

Compound 3 0.03%

! ■> water 23.97%

The ingredients will be used to give a spearmint flavored toothpaste of acceptable sweetness mixed together, but which is free of sugar or saccharin.

Example 10

chewing gum

Parts by weight

Compound 3 100 mg

(or compound 5 19 mg)

Benzoic acid 35 mg

Citric acid (dry weight) 1.67 g

Lemon essence 0.8 g filling up to 100 ml in
Mineral water polyvinyl acetate
Butyl phthalyl butyl glycolate
Polyisobutylene
Microcrystalline wax
Calcium carbonate
Flavor aroma
Connection 3
glucose

20th

0.07 10

The above gum base can be cut into conventional tablets or strips.

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

Claims (1)

27 OO claims: 1. Process for sweetening digestible products and non-digestible products to be taken, thereby marked draws that a compound of the general formula (I) is included in the products mentioned