LIQUID FUNCTIONALLY IMPROVED ISOMALT

Abstract

The present invention relates to a liquid isomalt composition comprising 6-O-alpha-D-glucopyranosyl-D-sorbitol (1,6-GPS) and 1-O-alpha-D-glucopyranosyl-D-mannitol (1,1-GPM) and the additional glycosylated isomalt components 1-O-(6-O-alpha-D-glucopyranosyl)-alpha-D-glucopyranosyl-D-mannitol (6-g-1, 1-GPM), 6-O-(6-O-alpha-D-glucopyranosyl)-alpha-D-glucopyranosyl-D-sorbitol (6-g-1,6-GPS), 1,6-di-O-alpha-D-glucopyranosyl-D-sorbitol (1-g-1,6-GPS) and 1,6-di-O-alpha-D-glucopyranosyl-D-mannitol (6-g-1,1-GPM).

Claims

1. A liquid isomalt composition, comprising glycosylated isomalt components 1-O-(6-O-alpha-D-glucopyranosyl)-alpha-D-glucopyranosyl-D-mannitol (6-g-1,1-GPM), 6-O-(6-O-alpha-D-glucopyranosyl)-alpha-D-glucopyranosyl-D-sorbitol (6-g-1,6-GPS), 1,6-di-O-alpha-D-glucopyranosyl-D-sorbitol (1-g-1,6-GPS) and 1,6-di-O-alpha-D-glucopyranosyl-D-mannitol (6-g-1,1-GPM), wherein the weight ratio of 6-g-1,1-GPM:6-g-1,6-GPS:1-g-1,6-GPS:6-g-1,1-GPM in the liquid isomalt composition is 1:(0.7-1.3):(0.3-1.1):(1-2) (each based on wt. % and dry substance (DS) of the glycosylated isomalt components).

2. The liquid isomalt composition according to claim 1, wherein the weight ratio of 6-g-1,1-GPM:6-g-1,6-GPS:1-g-1,6-GPS:6-g-1,1-GPM in the liquid isomalt composition is 1:(0.8-1):(0.7-1):(1.2-1.8).

3. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises 0.01 to 0.2 wt. % 6-g-1,1-GPM based on the total weight (DS) of the liquid isomalt composition.

4. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises 0.01 to 0.2 wt. % of 6-g-1,6-GPS based on the total weight (DS) of the liquid isomalt composition.

5. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises 0.01 to 0.2 wt. % of 1-g-1,6-GPS based on the total weight (DS) of the liquid isomalt composition.

6. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises 0.01 to 0.4 wt. % of 6-g-1,1-GPM based on the total weight (DS) of the liquid isomalt composition.

7. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises at least 86 wt. % of 1,6-GPS and 1,1-GPM based on the total weight (DS) of the liquid isomalt composition.

8. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises at least 40 wt. % 1,6-GPS based on the total weight (DS) of the liquid isomalt composition.

9. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises 0.1 to 1.0 wt. % 1,1-GPS (1-O-alpha-glucopyranosyl-D-sorbitol) based on the total weight (DS) of the liquid isomalt composition.

10. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises 0.01 to 2.0 wt. % deoxy disaccharide alcohols based on the total weight (DS) of the liquid isomalt composition.

11. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises 0.01 to 2.0 wt. % of glucosylglycitols based on the total weight (DS) of the liquid isomalt composition.

12. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises 0.01 to 0.3 wt. % of mannitol based on the total weight (DS) of the liquid isomalt composition.

13. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises 0.01 to 0.4 wt. % sorbitol based on the total weight (DS) of the liquid isomalt composition.

14. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises at least 5 wt. % dry matter content based on the total weight of the liquid isomalt composition.

15. The liquid isomalt composition according to claim 1, wherein the liquid isomalt composition comprises at least 10 to 50 wt. % dry matter content based on the total weight of the liquid isomalt composition.

16. Food or luxury foods comprising the liquid isomalt composition according to claim 1.

17. A chewing gum comprising Use of the liquid isomalt composition according to claim 1 as a coating.

Description

EXAMPLE 1

[0081] Production of Liquid Isomalt Compositions According to the Invention

[0082] For the preparation of both liquid isomalt compositions according to the invention and liquid comparative isomalt compositions, crystalline isomalt-based mixtures were prepared in a first step as described below. These had 1,6-GPS and 1,1-GPM in an equimolar ratio of 43 to 57 wt. % 1,6-GPS to 57 to 43 wt. % 1,1-GPM and are referred to below as Isomalt-ST-based compositions (Isomalt-ST base) (see Table 1). In addition, crystalline isomalt compositions and comparative isomalt compositions were prepared that have 1,6-GPS and 1,1-GPM in a ratio of 70 to 80 wt. % 1,6-GPS to 30 to 20 wt. % 1,1-GPM and are referred to as isomalt GS-based compositions (Isomalt-GS base) (see Table 1).

[0083] For the preparation of the aforementioned crystalline isomalt compositions, an isomalt composition described therein as hydrogenated isomerized sucrose (sweetener) was prepared according to Example 1 of EP 0 625 578 A1 and a chromatographic separation of the components 1,1-GPM, 1,6-GPS, 1,1-GPS, 6-g-1,1-GPM, 6-g-1,6-GPS, 1-g-1,6-GPS, 6-g-1,1-GPM, deoxy disaccharide alcohol fraction and glycosylglycitol fraction. The individual components obtained after the separation in isolated form were mixed with commercially available mannitol and sorbitol in the quantities and proportions shown in Table 1 below to obtain substantially crystalline mixtures. Starting from the crystalline isomalt compositions prepared in this manner (samples 17 to 32, Table 1) and comparative isomalt compositions (samples 1 to 16, Table 1), aqueous solutions having a dry substance content of 75 wt. % based on the total weight of the solution were prepared in a further step according to the invention.

[0084] Sample 3 (comparative isomalt composition) can also be obtained by applying the method conditions mentioned in Example 1 of EP 0 625 578 A1 to an isomerized sucrose solution and subsequent chromatographic purification.

[0085] Both the comparative liquid isomalt compositions and the liquid isomalt compositions according to the invention have identical components, particularly the isomalt compositions are characterized by the presence of the four glycosylated isomalt components. The isomalt compositions according to the invention are distinguished from the comparative isomalt compositions particularly by different quantitative ratios of the four glycosylated isomalt components to one another.

TABLE-US-00001 TABLE 1 6-G-1.1 6-G-1.6 1-G-1.6 6-G-1.1 GPM GPS GPS GPM g/100 g/100 g/100 g/100 Sample g DS g DS g DS g DS number GC analysis Ratio Isomalt ST base Comparison 1 0.06 0.03 0.01 0.05 1 : 0.5 : 0.2 : 2 0.02 0.03 0.05 0.08 1 : 1.5 : 2.5 : 3 0.02 0.02 0.04 0.06 1 : 1.0 : 2.0 : 4 0.06 0.11 0.12 0.19 1 : 1.8 : 2.0 : 5 0.12 0.13 0.19 0.2 1 : 1.1 : 1.6 : 6 0.05 0.03 0.04 0.12 1 : 0.6 : 0.8 : 7 0.14 0.18 0.23 0.09 1 : 1.3 : 1.6 : 8 0.04 0.06 0.05 0.09 1 : 1.5 : 1.3 : Isomalt GS base 9 0.07 0.04 0.01 0.06 1 : 0.6 : 0.1 : 10 0.03 0.05 0.1 0.11 1 : 1.7 : 3.3 : 11 0.04 0.05 0.12 0.13 1 : 1.3 : 3.0 : 12 0.09 0.13 0.13 0.24 1 : 1.4 : 1.4 : 13 0.16 0.14 0.21 0.28 1 : 0.9 : 1.3 : 14 0.05 0.06 0.08 0.09 1 : 1.2 : 1.6 : 15 0.04 0.06 0.04 0.11 1 : 1.5 : 1.0 : 16 0.09 0.13 0.11 0.19 1 : 1.4 : 1.2 : Invention Isomalt (0.7- (0.3- ST base 1 1.3) 1.1) 17 0.07 0.05 0.02 0.07 1 : 0.7 : 0.3 : 18 0.02 0.02 0.01 0.03 1 : 1.0 : 0.5 : 19 0.08 0.1 0.08 0.15 1 : 1.3 : 1.0 : 20 0.18 0.13 0.16 0.26 1 : 0.7 : 0.9 : 21 0.02 0.02 0.02 0.03 1 : 1.0 : 1.0 : 22 0.07 0.07 0.06 0.08 1 : 1.0 : 0.9 : 23 0.06 0.07 0.06 0.11 1 : 1.2 : 1.0 : 24 0.11 0.14 0.12 0.22 1 : 1.3 : 1.1 : Isomalt GS base 25 0.09 0.06 0.03 0.09 1 : 0.7 : 0.3 : 26 0.05 0.04 0.04 0.08 1 : 0.8 : 0.8 : 27 0.13 0.12 0.13 0.21 1 : 0.9 : 1.0 : 28 0.15 0.15 0.11 0.18 1 : 1.0 : 0.7 : 29 0.03 0.03 0.04 0.06 1 : 1.0 : 1.3 : 30 0.06 0.07 0.05 0.08 1 : 1.2 : 0.8 : 31 0.03 0.04 0.02 0.05 1 : 1.3 : 0.7 : 32 0.08 0.1 0.09 0.16 1 : 1.3 : 1.1 : Deoxy Total 1,1- 1,1- 1,6- 1,1- disaccharide Glucosyl GPM + GPM GPS GPS Mannitol Sorbitol alcohols glycitols 1,6-GPS g/100 g/100 g/100 g/100 g/100 g/100 g/100 g/100 Sample g DS g DS g DS g DS g DS g DS g DS g DS number Ratio GC analysis Isomalt ST base Comparison 1 0.8 47.8 50.8 0.31 0.05 0.15 0.3 0.25 98.6 2 4.0 48.9 50.3 0.27 0.05 0.09 0.07 0.12 99.2 3 3.0 48.3 50.5 0.25 0.04 0.08 0.09 0.02 98.8 4 3.2 47.8 51.1 0.27 0.08 0.12 0.1 0.04 98.9 5 1.7 48.1 50.5 0.28 0.03 0.07 0.09 0.03 98.6 6 2.4 47.7 50.6 0.36 0.04 0.09 0.14 0.24 98.3 7 0.6 47.2 51.4 0.23 0.04 0.13 0.08 0.03 98.6 8 2.3 44.8 53.7 0.24 0.03 0.09 0.07 0.02 98.5 Isomalt GS base 9 0.9 23.6 75.1 0.46 0.05 0.16 0.17 0.2 98.7 10 3.7 22.4 76.2 0.43 0.04 0.11 0.1 0.24 98.6 11 3.3 22.4 76.2 0.37 0.06 0.18 0.07 0.03 98.6 12 2.7 22.6 76 0.41 0.07 0.17 0.09 0.01 98.6 13 1.8 23 75.2 0.55 0.05 0.13 0.14 0.05 98.2 14 1.8 22.9 75.5 0.57 0.05 0.15 0.12 0.09 98.4 15 2.8 22.6 75.9 0.4 0.04 0.13 0.1 0.04 98.5 16 2.1 22.5 76.2 0.35 0.04 0.12 0.12 0.08 98.7 Invention Isomalt (1- ST base 2) 17 1.0 47 50.7 0.3 0.05 0.1 0.1 0.38 97.7 18 1.5 47.3 51.9 0.29 0.04 0.1 0.1 0.13 99.2 19 1.9 48.3 50.5 0.21 0.03 0.08 0.08 0.14 98.8 20 1.4 49.9 48 0.22 0.05 0.13 0.09 0.33 97.9 21 1.5 47.8 51.1 0.33 0.05 0.11 0.13 0.27 98.9 22 1.1 47.5 50.9 0.36 0.07 0.17 0.21 0.2 98.4 23 1.8 48.7 50.2 0.24 0.03 0.06 0.05 0.14 98.9 24 2.0 48.1 50.6 0.22 0.07 0.13 0.12 0.06 98.7 Isomalt GS base 25 1.0 21 77.1 0.38 0.04 0.12 0.08 0.1 98.1 26 1.6 22.7 76 0.49 0.07 0.2 0.09 0.12 98.7 27 1.6 22.7 75.8 0.44 0.05 0.17 0.12 0.09 98.5 28 1.2 22.1 76.1 0.46 0.09 0.22 0.16 0.26 98.2 29 2.0 20.6 78 0.37 0.05 0.16 0.11 0.08 98.6 30 1.3 22.3 76.5 0.38 0.04 0.14 0.13 0.11 98.8 31 1.7 22.4 75.9 0.41 0.08 0.3 0.23 0.24 98.3 32 2.0 22.1 76.1 0.47 0.06 0.15 0.12 0.18 98.2

EXAMPLE 2

[0086] Examination of Discoloration During Storage

[0087] The liquid isomalt compositions produced in example 1 were each stored in 10 L canisters at a temperature of 85 C. for a total of 21 days. After 0, 2, 4, 7, 12, 14 and 21 days a small partial amount was taken to measure the color of the solution according to the International Commission for Uniform Methods of Sugar Analysis (ICUMSA, based on method GS2/3-9).

[0088] A sample solution having a dry substance content (refractometric) of 20% is adjusted by dilution with demineralized water. The solution obtained is added to a disposable syringe and filtered through a syringe filter (Sartorius Minisart, 0.45 m) into a cuvette made of optical glass (transmittance from 360 nm, path length 5 cm with lid), wherein the first 5 mL are discarded. The cuvette is covered and left to stand for 15 minutes. The absorbance (E.sub.420) of this solution is then measured in a spectrophotometer (Hitachi) at 420 nm against a reference cuvette filled with water. The color in solution in ICUMSA units F.sub.IE is obtained by calculation:

F.sub.IE=1000.sub.420=1000E.sub.420/(dc) [0089] .sub.420=extinction coefficient [0090] E.sub.420=extinction (at 420 nm) [0091] d=layer thickness of the cuvette (5 cm) [0092] c=concentration (g/mL)=.sub.20%(DS/100) [0093] TS=dry matter content (g/100 g, adjusted to 20 g/100 g) [0094] .sub.20%=1.081 (density of a 20.0% measuring solution)

[0095] As can be seen from Table 2 below, the liquid isomalt compositions according to the invention (samples 17 to 32) were observed to have a significantly lower discoloration during storage time than the comparative isomalt compositions (samples 1 to 16). The comparative isomalt compositions showed a distinct yellowish tinge after 21 days, whereas the isomalt compositions according to the invention showed only a weak yellow coloration. The liquid isomalt compositions according to the invention showed a noticeably delayed tendency to discolor and therefore proved to be significantly more stable during storage.

TABLE-US-00002 TABLE 2 Storage test-examination of the discoloration Color in solution (filtered) Storage time at 85 C. (days) Sample 0 2 4 7 12 14 21 number ICUMSA units Comment Isomalt ST base (solution in water with 75% DS) Comparison 1 <10 <10 12 15 26 29 39 clear 2 <10 <10 16 18 22 34 42 yellow 3 <10 12 17 21 24 31 38 tinge 4 <10 <10 14 23 29 38 47 after 5 <10 14 16 24 27 38 53 21 days 6 <10 <10 15 19 26 34 42 7 <10 <10 14 19 28 37 46 8 <10 <10 13 16 21 32 38 Isomalt GS base (solution in water with 75% DS) 9 <10 <10 13 17 24 31 36 clear 10 <10 <10 <10 13 26 32 38 yellow 11 <10 <10 <10 17 28 32 41 tinge 12 <10 <10 12 14 21 29 34 after 13 <10 <10 12 17 26 32 39 21 days 14 <10 <10 <10 14 27 30 37 15 <10 13 18 23 29 33 43 16 <10 <10 12 18 27 34 38 Invention Isomalt ST base (solution in water with 75% DS) 17 <10 <10 13 15 16 21 26 only 18 <10 <10 <10 12 17 19 24 slight 19 <10 <10 <10 11 14 18 21 yellow 20 <10 <10 <10 16 17 21 25 coloration 21 <10 <10 12 14 15 20 23 after 22 <10 <10 <10 12 19 24 28 21 days 23 <10 <10 <10 13 17 21 26 24 <10 <10 <10 12 16 19 24 Isomalt GS base (solution in water with 75% DS) 25 <10 <10 <10 <10 12 18 22 only 26 <10 <10 <10 13 15 20 24 slight 27 <10 <10 <10 <10 14 16 20 yellow 28 <10 <10 <10 14 19 22 25 coloration 29 <10 <10 <10 13 18 23 28 after 30 <10 <10 <10 14 17 22 26 21 days 31 <10 <10 <10 <10 12 16 21 32 <10 <10 <10 <10 13 15 19