JPS5820588B2 - Compositions and methods for imparting sweetness - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to techniques for producing artificially sweetened foods, and more particularly to a free-flowing, mixable and highly soluble sweetening composition of sweet L-aspartic acid derivatives. Concerning the means of changing to

Members of the sweet-tasting aspartic acid derivative family, such as the dipeptide L-aspartic acid ester of L-phenylalanine (APM), have a dissolution rate that is less than desirable for so-called ready-to-eat foods such as food mixes containing artificial sweeteners. It is characterized by low

Therefore, by subdividing this group of compounds to increase their dispersion and dissolution rates, they can be made more easily dispersible,
There has been a need for a means to make it easily soluble.

Attempts to subdivide the crystalline particles of such compounds to increase their rate of dissolution have not been very successful, and other means have been used to effectively increase the rate of dispersion and therefore dissolution.

One common problem with such compounds appears to be their charged electrostatic properties; when recovered in crystalline form they have an inherent counterion production capacity; indeed, the compounds retain their sweetener properties. They are expected to have this production capacity while they do so.

When foods, such as beverage mixes containing food acids and powdered flavors and colors, are mixed with artificially sweetened compounds, they will have elasto-rheological properties due to the charged electrostatic properties of this compound. .

Furthermore, such mixes tend to become micronized and are not free-flowing compared to the more free-flowing active ingredients that characterize the mix; resulting in irregular or even unusable beverages and similar food products. It becomes a prescription.

Attempts to reduce these effects, for example by screening, are not effective.

This is because the effects of subdivision are not permanent;
This is because sweet compound particles re-agglomerate under the influence of their inherent electrostatic charge.

It would be desirable to be able to provide L-aspartate-derived sweetening compounds in a form that is easily blendable and free-flowing, and also has high dissolution and dispersion rates.

Preferably, such compounds should be blendable with the characteristic numbering and coloring components, or should themselves be both numbering and coloring and at the same time stable sweetening compounds.

A method has now been developed for producing discrete crystals of L-aspartic acid derivative compounds meeting the above requirements by using small amounts of essentially dissolved compound as a medium to aggregate the crystals into an immobilized state.

The crystals are randomly bonded at spaced contacts by a dry solution of APM or similar sweetening material.

In its preferred form, which is a representative embodiment of the present invention,
The sweet compound crystals are hydromilled to a uniform particle size.

This concomitantly dissolves some crystals, forming a cohesive solute; atomizing the hydromilled slurry with droplets produced by pumping the slurry, preferably at a low temperature that minimizes dissolution. drying, such as by passing through a nozzle and spray drying; the droplets advantageously have a portion of the finely dispersed crystals dried on top of each other, and the droplets form a dry powder. The contact point, which when recovered as a free-flowing, round-shaped permanent aggregate of sweet compounds, is permanently bound to each other by the solute sweet compound.

In another aspect of the invention, the sweetening compound in crystalline form is
Combined with a small amount of water, this converts a portion of the sweetening compound into a semi-moist, or dough-like, meal by dissolving it in the water and forming a cohesive solution.

The meal can be converted into a manageable mass, for example by extrusion at room temperature, and the extrudate or terraform mass can be dried and then ground.

Agglomerated particles have the same characteristic random overlap of crystalline sweet compounds that are adhered at regularly spaced contact points through an intermediate re-dried sweet compound that serves to crosslink the crystalline particles into immobilized granules.

The methods and products of the invention, ie, the compositions produced by the methods, are selected depending on the intended advantageous use of the products.

The preferred spray-dried particles, which are very free-flowing and have a high rate of dissolution, are preferred for use in beverage applications, whereas for applications other than dry beverage mixes, granular structures with smaller particles are preferred. It is practical to use any suitable dough forming method described below.

The present invention is useful for effectively immobilizing a wide range of aspartic acid derivatives classified as follows.

(1) L-aspartyl-2,5-dihydro-L-phenylalanine, L-aspartyl-L-(1-cyclohex-1-ene)-alanine, L-aspartyl-L-
Phenylchrysine and L-aspartyl-L-2,5-
Methyl ester of dihydrophenylglycine; (2) Methyl L-aspartyl-L-α-phenylchrysinate and its salts; (3) Jmperial Jndstries
Ltd. on 18 February 1971, South African Patent 6
Lower alkyl ester of L-aspartyl-L-(β-cyclohexyl)alanine disclosed in the publication of No. 695,910; (4) Stamicarbon, NV 197
Dutch Patent No. 7, rumored to have been granted for the production of aspartyl compounds, issued on May 19, 2007. α-L or DL-aspartyl-L described in the publication of OO7,176
or an alkyl ester classified as DL-substituted glycine; (5) Takeda Pharmaceutical Co., Ltd....described in French Patent No. 2,105,896, granted on April 28, 1972, regarding dipeptide ester sweeteners; A hydrogenated dipeptide ester sweetener such as L-asparadio-〇-etherified serine methyl ester; Formula (6); (wherein R and R1 are CH3 or C2H5, and R2
are the stereochemistry L-L, DL-L, L-DL.

or C47 alkyl representing DL-DL; aspartic acid peptide ester represented by the formula (7): (wherein R is a lower alkyl group such as a methyl group), anhydrous N-protected- G, D produced by reacting L-aspartic acid with L-phenylalanine lower alkyl ester.

5earle and Co, November 28, 1973
and (8) the sweeteners disclosed in British Patent No. 1,339,101 issued to Proctor and Gamble.
West German Patent No. 2,306, granted August 23, 973
, No. 909, a sweet preparation represented by the formula: L-aspartyl-L-1,4-dimethylpenamide.

In a preferred spray drying method, the aspartic acid derivative crystalline solid in the small shed is mixed with water and heated to 66°C (15°C).
The slurry is then maintained at a temperature well below 0'F), typically at ambient room temperature conditions.

This dissolves a minimal amount of the crystalline material, leaving the majority undissolved and most of it hydrated.

The slurry is then subjected to hydromilling, for example by passing it through a mill having narrower orifices than 125 mils between the working mill faces, which can be operated to subdivide the crystalline material into a uniform particle size distribution. Grind vigorously under pressure between.

The hydromill milled slurry is then spray dried to the desired shape.

Partial dissolution of the sweetening compound provides sufficient cohesive adhesion between the undissolved crystalline sweetening compounds, so that when the droplets evaporate, they are separated at regular intervals, with the re-dried compound itself in between. The crystals will randomly aggregate at the contact points where they are placed.

As previously pointed out, the slurry can be dried by means other than spray drying, but the formation of droplets and the resulting surface tension effects bind the crystals into a spherical agglomerate, thus substantially Spray drying is most preferred in that it allows permanent bonding to each other in a structure intended to provide immobilization and reduction of electrostatic charging effects.

The slurry can be dried by any of a number of well-known drying methods used in food manufacturing technology, such as drum drying, oven drying, freeze drying, etc.

In all of these methods, a relatively low temperature slurry is used which, if dried together in the unitary state, is then subdivided into the granular form used.

Instead of using a slurry as a whole, the dough can be made by using the cohesiveness of the peptide and the water crystals generated by adding water to the peptide, thereby making it possible to make a dough that is moist and suitable. A suitable dough or meal is produced, converted into a shaped body, for example by an extrusion process, which is a preferred process, and then re-dried.

Concomitant with this redrying, the individual crystals become permanently bonded to each other with the redried dissolved sweetening compound interposed therebetween.

Forming a slurry or dough involves adding compatible inert or ancillary agents, such as colorants and even fragrances, in the aqueous phase if they cannot participate in the destabilizing reaction with the L-aspartic acid derivative. This does not exclude its existence.

That is, colorants can be dissolved in the aqueous medium used to produce the slurry or meal, so that, for example, the spray-dried product can be advantageously colored without the need for blending.

Similarly, water-insoluble substances can be emulsified or homogenized in an aqueous medium to form a slurry or dough to effect combination with a sweetening compound, with the remaining water present partially dissolving the compound and causing agglomeration. Helps form a cross-linking solution.

Additionally, other artificial sweeteners such as saccharin and/or cyclamates can be blended in small quantities and homogeneously dispersed in the slurry or dough matrix depending on the particular method used. It can provide a pleasant shock of sensual sweetness.

In this process, it is desirable to use a cyclomate with a very low weight of saccharin, and to have a very small overlay of all monoaspartic acid compound solids used, so that the resulting sweetening composition is It is made soluble and provides a balanced and pleasant sensory sweetness when used in beverages and other food applications.

In these methods, the artificial sweetener can be dissolved in the aqueous phase, dry blended in the non-aqueous phase, or crystallized and fixed by random aggregation of mono-aspartic acid derived compounds.

All of these methods produce the most fluid, easily blendable, stable and highly soluble compositions without the drawbacks due to the electrostatic properties that the sweetening compounds themselves still possess.

The invention will be understood in more detail by the following examples.

Example APM crystals (30%) and room temperature tap water (70%) were mixed.

The resulting mixture was charged to a Frymamill and passed through a cerated opening with a gap of about 75 microns to reduce the particle size of the APM particles and to make them fluid and pumpable in a reamed slurry. The crystal mass is finely divided and the slurry is pumped at room temperature to a spray nozzle for spray drying, which produces droplets at 29,8 K.
210° C. with a spray pressure of p/cIft (425 psig)
(410'F) and an inlet dry air temperature of approximately 112°C (23'F).
5°C) and an air flow rate of approximately 2600°C.
It was placed in a vertical spray drying tower with 3 feet/m.

The dried charge droplets had a moisture content of 1.07%, 0.248
Density of S'/CC and bulk density of 0.304 r/CC (
A single charge of material was recovered at a density obtained by shaking under the influence of shaking alone, without applying any appreciable positive mechanical filling force, until the limit of density loss was reached.

The dry particles had the following particle size distribution:

The dried product has a very large size, with 99% of the constituent particles falling between the 60 mesh size and 200 mesh size.
It is noted that it has a particle size distribution.

Advantageously, the product has constituent particles of 1.101
of spray-dried APM aggregates at 7.2 °C when triblended with 3.6 l of anhydrous citric acid and placed in water.
A complete solution is formed by stirring with a spoon for 40 seconds in 1892 water (below 45).

Similar mixtures of APM-acid mixes not treated according to the invention took 60 to 90 seconds to dissolve, depending on the particle size distribution and size of the sweetening compounds involved.

The complete beverage mix containing color, flavor and citric acid blended with the treatment agent APM particles of the present invention had self-flowing properties that are highly favorable for food manufacturing processes.

Claims (1)

[Claims] 1. A method for producing a fluid dry sweet composition, comprising (a)
Crystal particles of an L-aspartic acid derivative sweet compound,
b) an amount of water that causes at least a portion of the crystal particles to remain undissolved to form a mixture of undissolved compound particles; The compound particles are ground into a uniform slurry free of agglomerates, the undissolved particles of the compound are randomly associated with each other while the solute solution generated in the slurry is distributed throughout the particles, and the slurry is spray-dried. immobilizing the particles at a number of spaced contact points in a random arrangement with a re-dried compound interposed therebetween, such that the sweetening composition is substantially immobilized by the re-dried compound. A method, wherein the particles. 2. The method of claim 1, wherein the compound particles are ground to a particle size of less than 125 microns. 3. The method according to claim 1, wherein the amount of water accounts for the majority of the mixture of compound and water in the overlapping section. 4. The method of claim 1, wherein the slurry is maintained below 66°C (below 150°C) before drying. 5. The compound particles are distributed in an amount of water that causes the particles to agglomerate in the random arrangement forming a dough-like shape-retaining meal in which a solution of the sweetening compound is distributed. The method described in Section 1. 6. The method of claim 5, wherein the meal is shaped and subdivided. 7. The method according to claim 1, wherein the compound is an alkyl ester of L-aspartyl-L-phenylalanine. 8. In a free-flowing, highly water-soluble, powdered sweetening composition, a redrying amount of L-aspartic acid sweetening compound aggregated with each other at several spaced contact points through intervening cohesive bonds formed. A composition consisting essentially of interdigitated random aggregates of immobilized crystalline particles of said L-aspartic acid sweetening compound particles immobilized by a redrying compound. 9. The composition according to claim 8, wherein the compound is an alkyl ester of L-aspartyl-L-phenylalanine. 10. The composition according to claim 9, wherein the compound is L-aspartyl-L-phenylalanine methyl ester. 11. The composition according to claim 8, wherein the amount of water accounts for the majority of the mixture of compound and water in the overlapping part. 12. The composition according to claim 8, wherein the proportion of the artificial sweetener in the overlapping portion is small.