JPS6087764A - Sweetener composition - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION Background of the Invention Aspartame (1-methyl N-L-α-aspartyl-L-phenylalanii) is a widely used sweetener. Its manufacture and use are covered by a U.S. patent. Third
, 492.151 and 5.642.49
1 Saimei Book a.

FDA Regulation 21 CFR 172,804, (C) C5
) states that when aspartame is used as a table sugar substitute, it must be used in cooking or baking.
t, 64" 8, finger ok!:・4. . □ Regulations.

ing. This warning label is based on the fact that it has become clear that aspartame is unstable when heated.
Requested by DA. For example, aspartame can break down, typically when baking cakes, cutlets, and pannato.

The present invention solves the problem of aspartame being unstable during baking.

3. DETAILED DESCRIPTION OF THE INVENTION Aspartame and its salts and gold member complexes are protected during heat treatment by coating the sweetener with partially hydrogenated vegetable oil. Aspartame or its salts or metal complexes and partially hydrogenated vegetable oils are passed through 8-40 standard mesh particles having a diameter of 2508 microns in 8 mesh and 840 microns in 20 mesh. It is important to form the aspartame to a particle size of 40 mesh, which refers to a standard screen that passes particles with a diameter of 420 microns, and 80 mesh, which passes particles with a diameter of 177 microns, so that the aspartame is released after a delay in the heating process. It is.

The aspartame sweetener is preferably first prepared to a particle size of 14-80 standard mesh, most preferably 14-65 standard mesh, and then coated (with a partially hydrogenated vegetable oil). It is preferred to form a fine grain of 8-40 standard mesh. Therefore,
The present invention is a thermally stable trout consisting of 8-40 mesh particles containing aspartame or a salt thereof and a partially hydrogenated vegetable oil that melts at over 120'F' by weight. sweet compositions.

The present invention utilizes the principle that aspartame in solid form is much more stable than aspartame in solution.

O-ting with a suitable fat will prevent aspartame from dissolving during preparation and baking.
Stabilize. Both the type of fat and the particle size of the fat-coated aspartame were found to be important. The melting point of JJI is also an important factor in producing aspartame-stabilized, fine-grained products during baking. This principle is \1. ．． Other artificial sweeteners such as tucarin and aceaulfame K and combinations with aspartame are also applicable.

3. Detailed Description of the Invention Aspartame (1-methyl IJ-L-α-aspartyl-L-phenylalanine) has the following chemical structure.

CH,COOH Aspartame salts are also effective sweeteners, usually with greater stability than aspartame itself. Typical salts are sulfates and lower alkyl sulfonates (with the exception of
Lower alkyl groups have 1-4 carbon atoms). A preferred salt has the formula (Al)M-H)280. Bis(hydrogen aspartyl phenylalanine methyl ester) sulfate represented by and formula (APM-H) 803CH3
Hydrogen aspartyl phenylalanine methyl ester methyl sulfonate represented by

Aspartame complexes are also more stable in the isomorphic state than aspartame alone.

Typical metal complexes are derived from all classes of pharmacologically acceptable ions and anions. A typical remainder ion is C
a", Zn" l Mg" l J+++, Fe"
+ and pe +++, typical anion beam o
lJ do, acetate, sulfate and phosphate.

Preferred aspartyl phenylalanine methyl ester (APM) metal complexes include: Mg"-APM-2C1 Fe++" APM-5C2 At"" 2APM-5C1 Ca"APM-2C1 Zz"APM-2C1. Aspartame, etc. and metal complexes can be protected during the haking process with fats, especially partially hydrogenated vegetable oils that melt above 120°F.

Partially hydrogenated triglyceride vegetable oils that melt above 120"F', such as soybean oil, palm oil, and cottonseed oil, are preferred fats useful in the practice of this invention. Typically, 7-1 parts by weight of About 6-9 parts by weight of fat is used to coat APM, its salts or metal complexes.

APM, its salts or metal complexes can melt fat and produce AP
Fat coating by adding M or by mixing APM and fat before melting the fat. The fat is cured and filtered through a standard fat-coated particle mesh screen.
-40 standard mesh particle size range or about 2680 to 4
Obtain 20 micron fat coated APM particles.

The ideal coating would not only be compatible with aspartame (it would have a melting point of about 100°C and release aspartame by the end of the baking process.
Mechanisms other than melting fat are believed to slow the release of aspartame during baking. This can be achieved by increasing the thickness of the fat coating and/or the granularity of the baked product by increasing the diffusion time of the melted fat into the matrix of the cake.

Therefore, the particle size is APM y at the end of the baking process
This is important because it is regulated to emit.

If the particle size is too small, the APM will be prematurely released and thermally decomposed during the baking process.

If the particle size is too large, the sweetness will not be fully released and distributed. Therefore, the particle size, type and melting point of the fat are important.

When used to sweeten baking products in high environments such as chocolate cake, this product requires acidic polydextrose il A during the fat coating process.
It has been found to be advantageous to include it together with PM. The amount of polydextrose is 6-8 parts of APM.

The invention will be further illustrated by the following examples, which are intended to illustrate unexploited BAs and are not intended to limit the spirit and scope of the invention.

Example 1 Method for Preparing Fine Granules I 60 parts of 151-158'l? Melt partially hydrogenated triglyceride soybean oil in a flat bottom pot.

Gradually add 10 parts aspartame (APM) w to coat the powder with the molten oil.

The heating is interrupted and 60 parts of the polydextrose powder is dispersed in the molten oil with stirring. The mass is stirred during assimilation to produce fine grains. i'' grains are separated on a standard 20 mesh screen. This method is applicable when using 1υ-60 parts of fat.

Method■ Polydextrose-aspartame non-porous injection granules [A
PM k: , polydextrose or maltriy
It is prepared by mixing a coarse grain-forming compound such as (Maltrin) M 100 with water or a water-alcohol mixture to form a dough, which is expanded and dried at 80° C. in a Makabe open oven. This dried product was then ground to a fine powder] by adding with stirring a solution of 400 parts of polydextrose in 600 parts of aspartame and 150 parts of hot water to substantially dry. Produced by heating and drying until fine grains form. These granules are passed through a 60 standard mesh screen.

Method: 6 parts of APM and 2 parts of polydextrose are mixed in a high-speed stirring granulator using water (6-10% by weight) as a granulation solvent and heat to facilitate granulation. I made it into grains. The granules were dried on trays and sieved to a particle size distribution of 14-60 mesh. The fine grains were coated with 50% Duratex using a fluid bed granulator with heating and pumping equipment to melt and spray the high melting point fat. . Part of coated fine grains'f: 12-5 over wJ
Samples were 0 mesh and 16-60 mesh.

The granules are coated with fat by mixing 50 parts of granules with 50 parts of finely powdered fat and gradually heating with stirring until the granules are coated.

The coated granules are passed through both 10 and 20 standard mesh screens.

Method 1. 1 and ■ can be applied when polydextrose is not used. For example, aspartame may itself be granulated or mixed with other granulating agents.

The heat-stabilized compositions of the present invention can be used in one or more of the following examples.

Example 2 Cake recipe used in the following example -200-206 Aspartame 1.2 - 1.2 -Malt, r
inMloLl 115-2 (JO-flour 15
4 165 147 147 powdered cocoa - -56,
56 Baking powder 6.8' 6.8 1.2 1.
2 baking soda - -5,15,5 salt 5.4
5.5 3.6 5.6 Shortening 50 55.6 56 42 Water 92
92 Milk 194 180 - Putter milk - -9999 Egg 54 70 54.5 54.5 Vanilla Ri, 14.2 1.8 1.8 Blue polydextrose-APM yellow cake: Place lJalRlnMloo with the same amount of polydextrose Same as APM yellow cake except for the change.

Example 6 Compatibility of APM compounds with different types of fats.

By analyzing fat-coated samples,
I got the following results. Unheated samples were used as controls to determine compatibility at elevated temperatures. C in all samples, and the weight ratio used was 9=1 (fat: APMized@-material). The samples were heated at 110°C for 40 minutes. APM was extracted from fat-coated samples using solvent-solvent ([1, Q i N HCl-methylene chloride) extraction and measured by high performance liquid chromatography (HPLC) methods.

APM content (%) Durat, ax(9), APM(1)' 9.96
9.55 6.5Durkee17(9), ARM(
1) 10,40 8.40 18.7KL,X(9)
, APM(1) ' 10,20 8.50 16.7
Aratex (9), APM (1) 9,60 9.7
4 0Kaomel (9), ApM (1) 9.84
8.74 11.2AtmO8K150(9), APM
(1) 9,25 6.92 57.6 Myverol
(9), APM (Li 9.60 0 100 Stearic Acid (9), APM (1)' 9.56 0 100 This study shows that triglyceride fats have the best compatibility with APM compounds at high temperatures and coatings. This indicates that it is suitable for use in

Example 4 Temperature of the cake during baking.

The temperature inside the cake during baking was observed using a thermocouple inside the cake and recorded every minute.

The results show that at the end of the 40 minute baking time, the cake temperature reaches a plateau of about i 12-120'υ. Therefore, the maximum temperature of the cake being baked is APM in the solid state, (APM-H)2SO
4, and APM-CaC42 min'! ! I temperatures (160°C, 180°C and about 175°C, respectively). Therefore, if these sweeteners can be kept in solid form by preventing them from dissolving in water, for example by coating with fat, they will be stabilized during baking.

il　5 Summary of analysis results of yellow cutlet cake by HPLC method.

Sa O size 11 Ward ■　za F N sentry r-Q λ Hehe Momo state Ne ＊　＊ Good 4 The following can be seen from the above results.

(1) Fine encapsulation of polydextrose with fatty acids increased the stability of API ill by more than 20% in baking.

(2) Substituting APM with compounds that are more thermally stable than APM, such as (APM-H), 804, and APM-CaCl2, significantly reduced the decomposition to DKP.

(3) The high temperature melting fats Durkee 17 and Duratex are somewhat better than the low temperature melting KLX.

(4) In research using a-grain Ci, 50% Durat
Best results are obtained using an ex coating and a uniform particle size of 20 to 10 meshes.

Example 6) IP for APM in chocolate cupcakes
Summary of Lc analysis results.

-6 Bepi d These results show that:

(1) All cakes using l1tf fat-coated APM sweetener had a significant increase in APM retention.

(2) The effect of coating thickness and particle size on the residual rate of APM in chocolate cake was greater than in the case of yellow cake (sample nos. 8, 9 and 10).

The best results with the +31 aac sample are the same as we used for the yellow cake, with a 50% fat coating and a uniform particle size of 20 to 10 mesh.

Example 7 Sensory evaluation results.

The cutlet cakes were prepared using different APM samples and baked at the same time, and 7 or more evaluators evaluated the flavor of the cutlet cakes.

The above results show that: (1) In baking, the stability of fat-coated (APM-J(), 804-CaSO4
(APM-H), comparable to 800 stability.

(2) Coated with Durkee 17 (APM
-H) The yellow cake prepared with 2804 is a polydextrose-APMi colored cake which is quite sweet.

(3) Cakes made with fat-coated APM samples, both yellow cake and chocolate cake, have sweetness and texture comparable to sugar cake.

(4) Chocolate cakes made with coated (ApM-a)2so are sweeter than those made with coated APM.

Example 8 Bake stability of non-porous APM-polydextrose granules coated with DurateX.

The above results clearly show that the greater the particle size and the greater the coating thickness, the greater the stability of the APM during baking, and that these factors are important for chocolate cakes.

This example shows that APM dissolves more slowly than its salts and complexes and can be advantageously used to stabilize APM in baking. Slowly dissolving factors can be increased by increasing the particle size of the APM. Therefore, DuratelX coated A
The PM granules are AP coated with DurateX.
Shows significantly better stability than M powder.

Trademark Product Description Maltrin M 100 is a Grain Proc
sold by Essing Corporation and has D, E, (dextrose equivalent) of 9-12
is a spray-dried hydrolyzed carbohydrate made from cornstarch.

Polyclextrose is Pfizer Che
Sold by Mical Division, it is a randomly bound condensation polymer of dextrose containing small amounts of bound sorbital and citric acid.

Duratex is Durkee Industria
Sold by Foods K and has a CMP of 141-
147'''F partially hydrogenated cottonseed triglyceride 1 oil.

Durkee 17 is Durkee Industry
Sold by ial Ii'oods and has a CMP of 1
52-158"F partially hydrogenated triglyceride soybean oil.

KLX is Durkee Industrial Fo
Sold by ods, CMP 124°-150'
F partially hydrogenated vegetable oil (mixture of cottonseed oil and soybean oil triglycerides).

ArateX is \Durkee Industrial
Cottonseed, soybean and palm oil trig sold by F'oods. It is a partially hydrogenated vegetable oil that is a mixture of riserides.

Kaomel %@, Durkee Industry
Sold by ial Foods and has a CMP of 97-
101'F partially hydrogenated vegetable oil.

Atmos K 150 is sold by ICI and has a melting point range of 155-142'i? It is a mixture of di-glyceride and di-glyceride fats.

Myverol is sold by East tlman and mainly (90 section)? Contains monoglyceride fats with an f1 point range of 154-165"F.

Grind CaCA2.2H20 to a fine powder. 2υ, O
l APM and i o, o 11 CaC72” 2H2
0 and mix thoroughly. Preheated to about 60-70℃ 3
Sip 001ILl 200 standard strength alcohol slowly without stirring. Rinse (filter) by suction.

After the solution has cooled to room temperature, it is cooled in the refrigerator. Collect the precipitated product by filtration. Dry overnight under vacuum and heating to about 60°C.

Dissolve a certain amount of calcium hydrogen oxide in a small amount of distilled water.
DiI or decompose. Alternatively, the corresponding bisulfate salt can be prepared directly in water using suitable calcium sulfate and sulfuric acid. Next, a certain amount of ---,,, --=,
a4 ・-1,-=h h; ? f<c+L+A!
uz-r'r? 6 folds while tM. Usage amount is AP
I+4: ca": H2SO4-2 should be compatible with a 1:1 chemical formula. About 10 to 20 times the volume of water used, organic solvents such as alcohol and isopropanol. , preheated to about 60°C, and stirred for 1 to 10 minutes overnight and at 5°C, the product suddenly formed a crystalline precipitate.

(APM-H) 2804 Distilled water (40#u) &+I,e (9695,1,6
6, '2) at various places and heated to about 40°. Add aspartame (10,0) to this solution and stir until the mixture becomes a clear solution, then add ethanol (400 ml) heated to about 60°.
? : Added while stirring. RH liquid drains quickly (filter, filter 1
When is it time to cool the fabric to about 5°? Let it settle, wash it with cold ethanol, and dry it in a vacuum at about 500℃ for about 2 hours.
A salt with a designation of approximately 11.9 was produced.

Examples of sulfonate salts of the invention include organic sulfonic acids (Rso, 2n) 'f! in place of sulfuric acid. r: Produced by the method described above.

Claims (1)

[Scope of Claims] (1) Particles of 8-40 standard mesh containing aspartame (APM), salts, or metal complexes thereof, and a portion that melts at a temperature of about 120° F. or higher and 30-90% by weight M%. A sweetening composition comprising hydrogenated vegetable oil. (2) The composition according to claim 1, which contains aspartame (APM) y. (3) Aspartame (APM-H) 280. A composition according to claim 1, characterized in that: (4) Aspartame (APM-H)2So3CH3
The composition according to claim 1, which contains: (51 Aspartame (APM"H) 2804"Ca
SO4, (kPM”H)2804 ・CaSO4, (A
PM-H)2804-Mgso4 or (APM・H)
Including 2SO4・2Mg5o4 [Z6, Wi if requested]
A composition according to scope 1. 161 Ca" (APM) 2 Ct-. (7) The composition according to claim 1, characterized by polydextrose. (8) The particles are 1 4-80 standard mesh fine grain containing aspartame, which is heated to about 120°F.
The composition of claim 1, wherein the composition is coated with a partially hydrogenated vegetable oil that melts at temperatures above or above to form particles of 8-40 standard mesh. (9) Particles contain aspartame 1 4-50
It is a fine grain of standard mesh size, which is about 6 120"
9. The composition of claim 8 coated with a partially hydrogenated vegetable oil melting at temperatures of F' or above to form particles of an R8-40 standard mesh. (The composition according to claim 9, wherein the fine particles having a particle size of 111410 standard mesh are composed of aspartame and polydextrose. (Aspartame ki- containing fine particles having a particle size of 11114-80#i semi-mesh) 120 A process for stabilizing aspartame, characterized in that it is coated with a partially hydrogenated vegetable oil melting at d degrees F or above to provide particles of 8-40 standard mesh.