Psicose syrup with improved performance

Abstract

The present invention relates to a psicose syrup with improved properties.

Description

Technical Field

[0001] The present invention relates to a psicose syrup with improved properties. Background Art

[0002] Allulose is a rare sugar with approximately 70% the sweetness of sucrose. Because it is not metabolized after ingestion, it has a very low calorie content. As a functional sweetener, it can prevent body fat gain and control blood sugar levels. Furthermore, despite being only 60% to 70% as sweet as sucrose, allulose is virtually calorie-free and has excellent solubility, making it suitable for a variety of food products.

[0003] During the manufacturing process of psicose, the product contains a low level of psicose, necessitating purification and concentration steps. However, the application of concentrated syrups is limited, leading to a higher demand for crystalline or powdered forms. However, psicose has a low degree of crystallinity and is difficult to crystallize. Therefore, psicose is mainly supplied in the form of psicose-rich syrups.

[0004] In addition, allulose syrup has the problem of easy browning. Therefore, it is necessary to provide a allulose syrup that can prevent browning or improve color stability, thereby delaying or reducing the occurrence of browning. Summary of the Invention

[0005] Technical issues

[0006] One embodiment of the present invention provides a saccharide syrup composition, such as psicose syrup, comprising psicose dimer crystals having a specific diffraction angle pattern or a dissolved solution thereof.

[0007] Another embodiment of the present invention is to provide a formulation for preventing browning of psicose syrup or a formulation for improving browning of psicose syrup, for preventing, inhibiting, reducing or improving browning of psicose syrup, comprising psicose dimer crystals having a specific diffraction angle pattern or a dissolved solution thereof.

[0008] Another embodiment of the present invention relates to a method for preventing or improving browning of psicose syrup, comprising the step of controlling the content of psicose dimer crystals having a specific diffraction angle pattern or a dissolved solution thereof in psicose syrup.

[0009] Another embodiment of the present invention relates to a method for reducing a yellowness change rate of psicose syrup, comprising the step of controlling a content of psicose dimer crystals having a specific diffraction angle pattern or a dissolved solution thereof in the psicose syrup.

[0010] Another embodiment of the present invention is to provide a formulation for preventing moisture loss of psicose syrup, for improving the moisture retention properties of psicose syrup, comprising psicose dimer crystals having a specific diffraction angle pattern or a dissolved solution thereof.

[0011] Another embodiment of the present invention relates to a method for preventing moisture loss in psicose syrup, comprising the step of controlling the content of psicose dimer crystals having a specific diffraction angle pattern or a dissolved solution thereof in the psicose syrup.

[0012] Technical Solution

[0013] One embodiment of the present invention relates to a composition for preventing or improving browning of psicose syrup, or a composition for preventing moisture loss, comprising psicose dimer crystals or a dissolved solution thereof, the psicose dimer crystals having an X-ray powder diffraction pattern comprising peaks at three or more positions selected from the group consisting of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° at 2θ diffraction angles in XRD analysis.

[0014] Another embodiment of the present invention relates to a saccharide syrup comprising psicose; and psicose dimer crystals or a dissolved solution thereof, the psicose dimer crystals having an X-ray powder diffraction pattern comprising peaks at three or more positions selected from the group consisting of 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° in X-ray powder diffraction (XRD) analysis.

[0015] The present invention will be described in more detail below.

[0016] The "psicose dimer" of the present invention refers to a molecule in which two psicose molecules are chemically condensed. Specifically, the psicose dimer may be a substance having 44.600 wt% of carbon, 5.907 wt% of hydrogen, and 53.556 wt% of oxygen, and may have a molecular formula of C 12 H 20 O 10 And a psicose dimer with a molecular weight of 324.11.

[0017] The psicose dimer of the present invention may be in the form of psicose dimer crystals or a dissolved solution thereof. The psicose dimer crystals may have peaks at three or more positions selected from the group consisting of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° in X-ray powder diffraction (XRD) analysis. Specifically, the psicose dimer crystals may have peaks at three or more positions selected from the group consisting of 15.51±0.2°, 17.66±0.2°, 18.14±0.2°, 19.34±0.2°, 7.76±0.2°, and 28.73±0.2° in X-ray powder diffraction (XRD) analysis.

[0018] As one embodiment, the D-psicose dimer crystal may have an X-ray powder diffraction pattern in X-ray powder diffraction (XRD) analysis that includes peaks at 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, and 18.14±0.5°; 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, and 19.34±0.5°; 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, and 7.76±0.5°; or 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5°.

[0019] As one embodiment, the D-psicose dimer crystal may have an X-ray powder diffraction pattern in X-ray powder diffraction (XRD) analysis that includes peaks at 2θ diffraction angles of 15.51±0.2°, 17.66±0.2°, and 18.14±0.2°; 15.51±0.2°, 17.66±0.2°, 18.14±0.2°, and 19.34±0.2°; 15.51±0.2°, 17.66±0.2°, 18.14±0.2°, 19.34±0.2°, and 7.76±0.2°; or 15.51±0.2°, 17.66±0.2°, 18.14±0.2°, 19.34±0.2°, 7.76±0.2°, and 28.73±0.2°.

[0020] In the X-ray powder diffraction (XRD) analysis results, the peak can be a peak with a relative intensity of 30% or more, 35% or more, 40% or more, 45% or more, 50% or more, 55% or more, 60% or more, 65% or more, 70% or more, 75% or more, 80% or more, 85% or more, 90% or more, or 95% or more. The relative intensity of the peak is expressed as a relative numerical percentage by the intensity of each peak based on the intensity of the peak with the maximum intensity of 100%.

[0021] Among the peaks, several peaks ranked from high to low by relative intensity, or peaks with relative intensity equal to or greater than a certain value, can be the main peaks defining the crystal form. For example, the main peaks can be 1 to 6, 1 to 5, 1 to 4, 1 to 3, or 1 to 2 peaks with the highest relative intensity. For example, the main peak can be a peak with a relative intensity of 30% or more, 35% or more, 40% or more, 45% or more, 50% or more, 55% or more, 60% or more, 65% or more, 70% or more, 75% or more, 80% or more, 85% or more, 90% or more, or 95% or more.

[0022] Therefore, the diffraction angle of the above-mentioned allulose dimer crystal can be the diffraction angle at the main peak with relatively higher intensity in X-ray powder diffraction (XRD) analysis, and the description order of the diffraction angle can be described from the diffraction angle of the peak with relatively higher intensity from high to low in X-ray powder diffraction (XRD) analysis.

[0023] As one embodiment, the D-psicose dimer crystal may have peaks in X-ray powder diffraction (XRD) analysis in descending order of relative peak intensity, including 15.51±0.5° and 17.66±0.5°; 15.51±0.5°, 17.66±0.5°, and 18.14±0.5°; 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, and 19. 34±0.5°; 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5° and 7.76±0.5°; or an X-ray powder diffraction pattern of peaks at 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5° and 28.73±0.5°. Specifically, the psicose dimer crystal may have peaks in an X-ray powder diffraction (XRD) analysis in descending order of relative intensity of the peaks: 15.51±0.2° and 17.66±0.2°; 15.51±0.2°, 17.66±0.2°, and 18.14±0.2°; 15.51±0.2°, 17.66±0.2°, 18.14±0.2°, and 19.34±0.2°. 0.2°; 15.51±0.2°, 17.66±0.2°, 18.14±0.2°, 19.34±0.2° and 7.76±0.2°; or an X-ray powder diffraction pattern of peaks at 2θ diffraction angles of 15.51±0.2°, 17.66±0.2°, 18.14±0.2°, 19.34±0.2°, 7.76±0.2° and 28.73±0.2°.

[0024] As an embodiment, the D-psicose dimer crystal may have an X-ray powder diffraction line pattern in which a peak having the highest relative intensity is located at a 2θ diffraction angle of 15.51±0.5° or 15.51±0.2° in X-ray powder diffraction (XRD) analysis.

[0025] As one embodiment, the D-psicose dimer crystal may have an X-ray powder diffraction line pattern in which two peaks with the highest relative intensity are located at 2θ diffraction angles of 15.51±0.5° and 17.66±0.5°; or 15.51±0.2° and 17.66±0.2° in X-ray powder diffraction (XRD) analysis.

[0026] As one embodiment, the D-psicose dimer crystals may have an X-ray powder diffraction line pattern in which three peaks with the highest relative intensity are located at 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, and 18.14±0.5°; or 15.51±0.2°, 17.66±0.2°, and 18.14±0.2° in X-ray powder diffraction (XRD) analysis.

[0027] The melting point of the allulose dimer crystals may be 210±5°C, 210±3°C, 210±2°C, 210±1°C, 210.5±5°C, 210.5±3°C, 210.5±2°C, 210.5±1°C, 210.5±0.5°C, 210.7±5°C, 210.7±3°C, 210.7±2°C, 210.7±1°C or 210.7±0.5°C.

[0028] The solubility of the psicose dimer crystals in water may be 5g / 100g to 20g / 100g, 5g / 100g to 15g / 100g, 5g / 100g to 12g / 100g, 5g / 100g to 10g / 100g, 7g / 100g to 20g / 100g, 7g / 100g to 15g / 100g, 7g / 100g to 12g / 100g, 7g / 100g to 10g / 100g, 8g / 100g to 20g / 100g, 8g / 100g to 15g / 100g, 8g / 100g to 12g / 100g, 8g / 100g to 10g / 100g, 9g / 100g to 20g / 100g, 9g / 100g to 15g / 100g, 9g / 100g to 12g / 100g or 9g / 100g to 10g / 100g.

[0029] The retention time of the psicose dimer analyzed by gas chromatography (GC) analysis may be 11 to 13 minutes.

[0030] One embodiment of the present invention relates to a composition for preventing or improving browning of psicose syrup, comprising psicose dimer crystals or a dissolved solution thereof. Psicose dimer crystals or a dissolved solution thereof can be included in psicose syrup to prevent or improve browning of the psicose syrup. Therefore, another embodiment of the present invention relates to a psicose syrup for preventing or improving browning, comprising psicose dimer crystals or a dissolved solution thereof.

[0031] In the present invention, "preventing browning" can be used to include inhibiting or delaying the occurrence of browning. Preventing browning, inhibiting browning, and delaying browning mean that the increase rate of browning level (e.g., yellowness value) is lower than that of the control group compared with that immediately after preparation.

[0032] In the present invention, "improving browning" may be used as a meaning including reducing the degree of browning, such as reducing yellowness. Improving browning may mean that the browning level (eg, yellowness value) becomes lower than that immediately after preparation.

[0033] Browning may be caused, for example, by one or more of heat, pH, and storage time. Browning includes non-enzymatic browning reactions such as amino carbonyl reactions, melanoidine reactions, and Maillard reactions that occur when amino and carbonyl groups coexist. These reactions include browning caused by the formation of osones, browning caused by the formation of intermediates such as unsaturated 3,4-dioxyketose, and browning in which furfural-generating cyclic substances including HMF (hydroxymethyl furfural) react with amino acids to become melanoidines and exhibit brown color. Browning also includes brown pigments derived from decomposition products of sugars.

[0034] Another embodiment of the present invention relates to a composition for preventing moisture loss in psicose syrup, comprising psicose dimer. Psicose dimer crystals or a dissolved solution thereof can be included in psicose syrup to prevent moisture loss in the psicose syrup. Therefore, another embodiment of the present invention relates to a psicose syrup for preventing moisture loss, comprising psicose dimer crystals or a dissolved solution thereof.

[0035] In the present invention, "preventing moisture loss" may be used to include inhibiting or delaying moisture loss in saccharide syrup (e.g., psicose syrup). Preventing moisture loss means that the amount of moisture loss is lower than that of the control group compared to that immediately after preparation.

[0036] The content of the psicose dimer crystals or the dissolved solution thereof according to one embodiment of the present invention may be 0.025 wt % or more, 0.03 wt % or more, 0.035 wt % or more, 0.04 wt % or more, 0.045 wt % or more, 0.05 wt % or more, 0.055 wt % or more, 0.06 wt % or more, 0.065 wt % or more, 0.07 wt % or more, 0.075 wt % or more, 0.08 wt % or more, 0.09 wt % or more, 0.10 wt % or more, 0.11 wt % or more, 0.12 wt % or more, 0.13 wt % or more, 0.14 wt % or more, 0.15 wt % or more, 0.16 wt % or more, 0.17 wt % or more, 0.18 wt % or more, 0.19 wt % or more, 0.20 wt % or more, 0.21 wt % or more, 0.22 wt % or more, 0.23 wt % or more, 0.24 wt % or more, 0.25 wt % or more, 0.26 wt % or more, 0.27 wt % or more, 0.28 wt % or more, 0.29 wt % or more, 0.30 wt % or more, 0.31 wt % or more, 0.32 wt % or more, 0.33 wt % or more, 0.35 The content of the psicose dimer crystals or a dissolved solution thereof can be measured based on gas chromatography (GC) analysis.

[0037] The content of the psicose dimer crystals or a dissolved solution thereof based on 100 weight % of the solid content of the psicose syrup may be 20 weight % or less, 19 weight % or less, 18 weight % or less, 17 weight % or less, 16 weight % or less, 15 weight % or less, 14 weight % or less, 13 weight % or less, 12 weight % or less, 11 weight % or less, or 10 weight % or less.

[0038] Another embodiment of the present invention relates to a saccharide syrup comprising psicose; and psicose dimer crystals or a dissolved solution thereof, wherein the psicose dimer crystals have an X-ray powder diffraction pattern comprising peaks at three or more positions selected from the group consisting of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° at 2θ diffraction angles in XRD analysis. The psicose dimer crystals or the dissolved solution thereof are as described above.

[0039] The solids content of the saccharide syrup can be 20% to 90% by weight, 20% to 85% by weight, 20% to 80% by weight, 20% to 75% by weight, 20% to 70% by weight, 25% to 90% by weight, 25% to 85% by weight, 25% to 80% by weight, 25% to 75% by weight, 25% to 70% by weight, 30% to 90% by weight, 30% to 85% by weight, 30% to 80% by weight, 30% to 75% by weight, 30% to 90% by weight, % to 85 wt%, 40 wt% to 80 wt%, 40 wt% to 75 wt%, 40 wt% to 70 wt%, 50 wt% to 90 wt%, 50 wt% to 85 wt%, 50 wt% to 80 wt%, 50 wt% to 75 wt%, 50 wt% to 70 wt%, 60 wt% to 90 wt%, 60 wt% to 85 wt%, 60 wt% to 80 wt%, 60 wt% to 75 wt%, or 60 wt% to 70 wt%.

[0040] The content of the psicose dimer or a dissolved solution thereof in the saccharide syrup may be 0.025 wt % or more, 0.03 wt % or more, 0.035 wt % or more, 0.04 wt % or more, 0.045 wt % or more, 0.05 wt % or more, 0.055 wt % or more, 0.06 wt % or more, 0.065 wt % or more, 0.07 wt % or more, 0.075 wt % or more, 0.08 wt % or more, 0.085 wt % or more, based on 100 wt % of the solid content. % or more, 0.09 wt % or more, 0.095 wt % or more, 0.1 wt % or more, 0.2 wt % or more, 0.3 wt % or more, 0.4 wt % or more, 0.5 wt % or more, 0.6 wt % or more, 0.7 wt % or more, 0.8 wt % or more, 0.9 wt % or more, 1 wt % or more, 1.5 wt % or more, 2 wt % or more, 2.5 wt % or more, 3 wt % or more, 3.5 wt % or more, 4 wt % or more, 4.5 wt % or more, or 5 wt % or more. The content of the psicose dimer crystals or a dissolved solution thereof can be measured by gas chromatography (GC) analysis.

[0041] The content of the psicose dimer or a dissolved solution thereof in the saccharide syrup may be 20 wt% or less, 19 wt% or less, 18 wt% or less, 17 wt% or less, 16 wt% or less, 15 wt% or less, 14 wt% or less, 13 wt% or less, 12 wt% or less, 11 wt% or less, or 10 wt% or less, based on 100 wt% of the solid content.

[0042] The saccharide syrup can be prevented from browning, and the prevention of browning is as described above. In the Examples of the present invention, it was confirmed that the increase in yellowness of the saccharide syrup composition containing psicose dimer or a solution thereof was suppressed compared with the control.

[0043] Specifically, based on the yellowness measured immediately after preparation as 100%, the saccharide syrup according to one embodiment of the present invention may have a yellowness change rate of 70% or less, 65% or less, 60% or less, 55% or less, 50% or less, 45% or less, 40% or less, 35% or less, 30% or less, 25% or less, 20% or less, 15% or less, 10% or less, 5% or less, 4% or less, 3% or less, 2% or less, or 1% or less after storage at a temperature of 60°C for 48 hours.

[0044] Specifically, based on the yellowness measured immediately after preparation as 100%, the yellowness change rate of the saccharide syrup according to one embodiment of the present invention after storage at a temperature of 60°C for 3 days may be 260% or less, 250% or less, 240% or less, 230% or less, 200% or less, 180% or less, 150% or less, or 130% or less.

[0045] Specifically, based on the yellowness measured immediately after preparation as 100%, the yellowness change rate of the saccharide syrup according to one embodiment of the present invention after storage at a temperature of 60° C. for 6 days may be 1400% or less, 1350% or less, 1300% or less, 1200% or less, or 1100% or less.

[0046] In one embodiment of the present invention, the saccharide syrup may have improved browning, and the improved browning is as described above. In the examples of the present invention, the results of the change in yellowness of the saccharide syrup containing the psicose dimer or a solution thereof according to one embodiment of the present invention were confirmed, and the yellowness was reduced compared to the initial yellowness.

[0047] Specifically, based on the yellowness measured immediately after preparation as 100%, the yellowness change rate of the saccharide syrup according to one embodiment of the present invention after storage at a temperature of 60° C. for 48 hours may be -5% or less, -10% or less, -15% or less, -18% or less, -20% or less, -25% or less, or -30% or less.

[0048] The yellowness change rate can be calculated by [(measured yellowness)-(yellowness immediately after preparation)] / (yellowness immediately after preparation)×100(%).

[0049] As an example, based on the yellowness measured immediately after preparation as 100%, the rate of change in yellowness of the saccharide syrup according to one embodiment of the present invention after storage at a temperature of 60° C. for 48 hours is -50% to 70%, -50% to 65%, -50% to 60%, -50% to 55%, -50% to 50%, -50% to 45%, -50% to 40%, -40% to 70%, -40% to 65%, -40% to 60%, -40% to 55%, -40% to 50%, -40% to 45%, -40% to 40%, -35% to 70%, -35% to 65%, -35% to 60%, -35% to 55%, -35% to 50%, -35% to 45%, or -35% to 40%.

[0050] The saccharide syrup can be prevented from losing water, and the prevention of water loss is as described above. In the examples of the present invention, it was confirmed that the saccharide syrup containing the psicose dimer or a dissolved solution thereof according to one embodiment of the present invention had less water loss than the control group.

[0051] Specifically, based on the moisture content immediately after preparation as 100 weight %, the moisture content of the saccharide syrup according to one embodiment of the present invention after storage at 60° C. for 1 day may be 57 weight % or more, 58 weight % or more, 59 weight % or more, 60 weight % or more, 61 weight % or more, 62 weight % or more, 63 weight % or more, 64 weight % or more, 65 weight % or more, 66 weight % or more, 67 weight % or more, 68 weight % or more, 69 weight % or more, or 70 weight % or more.

[0052] The saccharide syrup may further include at least one selected from the group consisting of monosaccharides other than psicose, disaccharides, sugar alcohols, oligosaccharides, high-intensity sweeteners, dietary fiber, protein, vitamins, seasonings, and colorants.

[0053] The monosaccharide may be one or more selected from the group consisting of fructose, glucose, and galactose.

[0054] The disaccharide may be one or more selected from the group consisting of sucrose, lactose, and maltose.

[0055] The sugar alcohol may be one or more selected from the group consisting of xylitol, erythritol, sorbitol, maltitol, mannitol, isomalt, and lactitol, but is not limited thereto.

[0056] The high intensity sweetener may be selected from one or more of the group consisting of steviol glycosides, stevia extracts, aspartic acid, aspartame, stevioside, enzyme-modified stevia, sucralose, saccharin, rebaudioside, monk fruit, mogroside, acesulfame potassium, thaumatin, brazzein, monellin, miraculin and pentadin, but is not limited thereto.

[0057] Dietary fiber may comprise water-soluble dietary fiber and / or insoluble dietary fiber, the water-soluble dietary fiber may be selected from one or more of the group consisting of arabinoxylan, fructan, inulin, pectin, alginate, agar, raffinose, polydextrose, maltodextrin and indigestible maltodextrin, and the insoluble dietary fiber may be selected from one or more of the group consisting of fibrin (cellulose), chitin, hemicellulose, lignin, xanthan gum and resistant starch, but is not limited thereto.

[0058] The protein may include animal protein and / or plant protein, but is not limited thereto.

[0059] The vitamins may include fat-soluble vitamins and / or water-soluble vitamins, but are not limited thereto.

[0060] There is no particular restriction on the types of seasonings as long as they are edible seasonings, for example, they can be selected from one or more of strawberry flavor, vanilla flavor, chocolate flavor, green tea flavor, apple flavor, grape flavor, blueberry flavor, raspberry flavor, cranberry flavor, watermelon flavor, orange flavor, banana flavor, caramel flavor, pistachio flavor, milk flavor, yogurt flavor, lemon flavor, chestnut flavor, peanut flavor, coffee flavor, black tea flavor, melon flavor, cereal flavor, sweet potato flavor, pear flavor, red bean flavor, walnut flavor, almond flavor, peach flavor, cherry flavor, sugar pancake flavor, tomato flavor, soda flavor, cola flavor, pumpkin flavor, and corn flavor.

[0061] There are no particular restrictions on the types of colorants as long as they are edible colorants, and for example, they can be selected from the group consisting of one or more blue colorants such as gardenia blue colorant and spirulina colorant, yellow colorants such as gardenia yellow colorant, turmeric colorant, annatto colorant, and carotene, red colorants such as beet colorant, cochineal colorant, shellac colorant, monascus red colorant, anthocyanin, and chili extract colorant, purple colorants such as purple cabbage colorant, purple potato colorant, and grape skin extract colorant, brown colorants such as cocoa colorant and caramel colorant, green colorants such as green spirulina and chlorella colorant, etc. As described above, various colorants can be prepared by combining various colorants.

[0062] Another embodiment of the present invention relates to a method for preparing a saccharide syrup containing psicose, the method including the step of controlling the content of psicose dimer crystals or a dissolved solution thereof in the saccharide syrup containing psicose, the psicose dimer crystals having an X-ray powder diffraction pattern including peaks at three or more positions selected from the group consisting of 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° in X-ray powder diffraction (XRD) analysis.

[0063] Another embodiment of the present invention relates to a method for preventing or improving browning of a saccharide syrup containing psicose, the method including the step of controlling the content of psicose dimer crystals or a dissolved solution thereof in the saccharide syrup containing psicose, the psicose dimer crystals having an X-ray powder diffraction pattern including peaks at three or more positions selected from the group consisting of 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° in X-ray powder diffraction (XRD) analysis.

[0064] Another embodiment of the present invention is directed to a method for preventing moisture loss in a saccharide syrup containing psicose, the method comprising the step of controlling a content of psicose dimer crystals or a dissolved solution thereof in the saccharide syrup containing psicose, the psicose dimer crystals having an X-ray powder diffraction pattern comprising peaks at three or more positions selected from the group consisting of 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° in X-ray powder diffraction (XRD) analysis.

[0065] The controlling step may control the content of the psicose dimer crystals or the dissolved solution thereof to be 0.025 wt % or more, 0.03 wt % or more, 0.035 wt % or more, 0.04 wt % or more, 0.045 wt % or more, 0.05 wt % or more, 0.055 wt % or more, 0.06 wt % or more, 0.065 wt % or more, 0.07 wt % or more, 0.075 wt % or more, 0.08 wt % or more, 0.085 wt % or more, or 0.095 wt % or more. % by weight or more, 0.09 % by weight or more, 0.095 % by weight or more, 0.1 % by weight or more, 0.2 % by weight or more, 0.3 % by weight or more, 0.4 % by weight or more, 0.5 % by weight or more, 0.6 % by weight or more, 0.7 % by weight or more, 0.8 % by weight or more, 0.9 % by weight or more, 1 % by weight or more, 1.5 % by weight or more, 2 % by weight or more, 2.5 % by weight or more, 3 % by weight or more, 3.5 % by weight or more, 4 % by weight or more, 4.5 % by weight or more, or 5 % by weight or more. The content of the dissolved solution may be the content of the psicose dimer crystals excluding the solvent.

[0066] The controlling step may include, for example, a step of adding the psicose dimer crystals or a dissolved solution thereof to the saccharide syrup, or a step of increasing the content of the psicose dimer crystals or a dissolved solution thereof in the saccharide syrup.

[0067] Beneficial effects

[0068] A composition for preventing or improving browning, a composition for preventing moisture loss, or a saccharide syrup according to an embodiment of the present invention comprises the psicose dimer crystals according to an embodiment of the present invention or a dissolved solution thereof. Therefore, it can prevent or reduce browning of psicose syrup during storage and minimize the loss of moisture contained in the psicose syrup. BRIEF DESCRIPTION OF THE DRAWINGS

[0069] Figure 1 A graph showing the solubility of Psicose dimer crystals according to one embodiment of the present invention.

[0070] Figure 2 A graph showing gas chromatography (GC) analysis results of D-psicose dimer crystals according to one embodiment of the present invention.

[0071] Figure 3 A graph showing the change in yellowness of a sugar syrup according to an embodiment of the present invention.

[0072] Figure 4 A graph showing the change in yellowness of a saccharide syrup according to one embodiment of the present invention depending on the content of finely divided psicose dimer crystals.

[0073] Figure 5 A graph showing changes in yellowness of a saccharide syrup when stored for a long period of time according to an embodiment of the present invention. DETAILED DESCRIPTION

[0074] The present invention will be described in more detail below through the following examples. However, these examples are only used to illustrate the present invention, and the scope of the present invention is not limited by these examples.

[0075] Example 1: Isolation of Psicose Dimer Crystals

[0076] The psicose syrup having a psicose purity of 95 wt % or more and a solid content of 68 wt % to 72 wt % was titrated to a pH of 3.5 or less and then stored at 35° C. until the psicose content dropped to 80 wt % or less.

[0077] When the psicose content dropped below 80% by weight, the psicose syrup was refrigerated to promote the crystallization of psicose dimer. Afterwards, upon visual confirmation of psicose dimer crystal formation, the psicose dimer crystals were separated from the syrup using ethanol. The separated psicose dimer crystals were dried in an oven to evaporate the ethanol, and then peak elution was monitored by HPLC. Fractions were collected based on the detector signal or retention time to isolate and purify the product. Specifically, HPLC was performed using a refractive index (RI) detector, a Biorad HPX-87C chromatographic column maintained at 80°C, and a mobile phase of distilled water (DW) at a flow rate of 0.6 mL / min to separate and analyze psicose dimer. This method yielded pure psicose dimer (purity 99% by weight) for subsequent experiments.

[0078] Example 2: Elemental Analysis of Psicose Dimer Crystals

[0079] The material analysis of the psicose dimer crystals obtained in Example 1 was performed using an elemental analyzer. A 1.8 mg sample was used, the analysis temperature was set to 1150°C, and sulfanilic acid and benzoic acid were used as standard substances. The analysis results showed that the substance had 44.600 wt% C, 5.907 wt% H, and 53.556 wt% O, and the molecular formula was confirmed to be C 12 H 20 O 10 , and the molecular weight was confirmed to be 324.11.

[0080] Example 3: Mass spectrometry analysis of D-psicose dimer crystals

[0081] The mass spectrum of the psicose dimer crystals obtained in Example 1 was analyzed using a high-resolution mass spectrometer. The ionization conditions used for the analysis were analyzed using the FAB (Fast Atom Bombardment) ionization mode.

[0082] The results of mass spectrometry confirmed that the molecular weight of the psicose dimer was 324.11, which was consistent with the analysis results of Example 2.

[0083] Example 4: X-ray diffraction analysis (XRD)

[0084] The psicose dimer crystals obtained in Example 1 were subjected to X-ray diffraction analysis according to the following specific analysis conditions. The top six peaks (relative intensity %) were selected from the X-ray diffraction analysis results of the psicose dimer crystals, as shown in Table 1.

[0085] [Table 1]

[0086]

[0087] As shown in Table 1, in the powder X-ray spectrum of the psicose dimer crystals obtained in Example 1, the 2θ values ​​of the first three peaks were 15.51°, 17.66°, and 18.14°, the 2θ values ​​of the first four peaks were 15.51°, 17.66°, 18.14°, and 19.34°, the 2θ values ​​of the first five peaks were 15.51°, 17.66°, 18.14°, 19.34°, and 7.76°, and the 2θ values ​​of the first six peaks were 15.51, 17.66, 18.14, 19.34, 7.76, and 28.73.

[0088] Example 5: Melting Point Analysis of Psicose Dimer Crystals (DSC Analysis)

[0089] Differential scanning calorimetry (DSC) was used to determine the melting point of the psicose dimer crystals obtained in Example 1. The analysis temperature range was -10°C to 250°C, and 4 mg of the psicose dimer crystal sample was quantitatively analyzed.

[0090] As a result of melting point analysis, the melting point of the psicose dimer crystals was confirmed to be approximately 210.7°C.

[0091] Example 6: Solubility Analysis of Psicose Dimer Crystals

[0092] In order to analyze the solubility of the psicose dimer crystals obtained in Example 1, water was used as a solvent and the solubility was evaluated at temperatures ranging from 25°C to 80°C.

[0093] The solubility analysis results in water were based on a solvent temperature of 25°C. The solubility of psicose was 34 g / 100 g (water), while the solubility of psicose dimer crystals was confirmed to be 9.2 g / 100 g (water). Figure 1 shown.

[0094] Example 7: GC Analysis of Psicose Dimer Crystals

[0095] 100 mg to 300 mg of the crystalline sample of the psicose dimer obtained in Example 1 was titrated, and 10 ml of 100 ml of pyridine mixed with 30 mg of phenyl β-D-pyranoglucoside was taken and mixed with the crystalline sample of the psicose dimer. 0.5 ml of the mixed solution was taken and placed in a 2 ml to 4 ml reagent bottle, evaporated and dried under a nitrogen flow, and then 0.5 ml of a solution in which 4 g of hydroxylamine hydrochloride was mixed with 100 ml of pyridine was taken and mixed with the evaporated and dried sample. The mixture was stirred thoroughly to dissolve the dry matter therein, and then placed at 70°C for 40 minutes. After 40 minutes, the reactants were brought to room temperature, and 0.4 ml of BSTFA and 0.1 ml of N-trimethylsilyl imidazole (TSIM) were added. The stopper was closed again, heated at 70°C for 30 minutes, then cooled at room temperature, and then used as a sample for GC analysis. The GC analysis conditions are shown in Table 2, and the GC analysis formula for dimer content is as follows:

[0096] Dimer (%) = (surface area of ​​the substance's GC peak from 11 minutes to 13 minutes / surface area of ​​the internal standard peak) * (weight of the internal standard added during sample pretreatment / sample weight) * (100 / dimer reaction coefficient)

[0097] -Dimer reaction coefficient: 1.15

[0098] [Table 2]

[0099]

[0100] The GC analysis results of the allulose dimer crystals are as follows: Figure 2 As a result of GC analysis, it was confirmed that a peak was detected at 11 minutes to 13 minutes.

[0101] Example 8: Anti-browning effect of allulose dimer (1)

[0102] The effect of the psicose dimer obtained in Example 1 on the browning of psicose syrup was confirmed. Psicose crystals with a purity of 99.99% and psicose dimer crystals were mixed in a weight ratio according to Table 3 to prepare a liquid sample, and the solid content was adjusted to 68 wt %. Each sample was stored at 60°C and sampled at 0 hour and 48 hours after storage. The yellowness was analyzed at 420 nm using a spectrophotometer at a solid content of 30 wt %. The yellowness change rate (%) at 48 hours compared to 0 hours was calculated according to the following equation 1, as shown in Tables 4 and 5. Figure 3 As shown:

[0103] [Equation 1]

[0104] Yellowness change rate (%) = [(yellowness at 48h) - (yellowness at 0h)] / (yellowness at 0h) × 100%

[0105] [Table 3]

[0106]

[0107] [Table 4]

[0108]

[0109] As shown in Table 4 above and Figure 3 As shown in the figure, as a comparison of the effect of the psicose dimer content according to one embodiment of the present invention on the browning process, it can be confirmed that the browning rate of the samples with a psicose dimer content of 0.05% by weight or more was reduced compared to the control group without addition. Moreover, it can be seen that the yellowness of the samples with a psicose dimer content of 0.4% by weight or more remained unchanged or decreased compared to the time at 0 hours. Therefore, psicose syrup containing a certain concentration or more of psicose dimer crystals according to one embodiment of the present invention or a dissolved solution thereof has the effect of delaying browning.

[0110] Example 9: Anti-browning effect of allulose dimer (2)

[0111] To further confirm the anti-browning effect based on the psicose dimer crystal content, the psicose dimer crystal content was divided into 0.01 wt% units according to the weight ratios described in Table 5. A psicose syrup was prepared using the same method as in Example 8 and stored at 60°C for 48 hours to accelerate browning. After 48 hours, the psicose syrup was adjusted to a concentration of 68 wt%, and the yellowness was analyzed at 420 nm using a spectrophotometer. The yellowness change rate (%) between 48 hours and 0 hours was calculated according to Equation 1, as shown in Tables 6 and 7. Figure 4 shown.

[0112] [Table 5]

[0113]

[0114] [Table 6]

[0115]

[0116] As shown in Table 6 and Figure 4 As shown, the psicose syrup containing 0.03 wt % or more of psicose dimer prevented browning, and specifically, a reduction in yellowness was observed compared with the control group.

[0117] Example 10: Anti-browning effect of psicose dimer during long-term storage

[0118] To confirm the effect of delaying browning according to the psicose dimer content during long-term storage of a saccharide syrup, a psicose syrup having a solid content of 71 wt% was prepared using the same method as in Example 8 according to the weight ratios described in Table 7 and stored at 60°C for 6 days to accelerate browning. After storage for 3 and 6 days, the psicose syrup was adjusted to a concentration of 30 wt%, and the color value was analyzed at 420 nm using a spectrophotometer. The yellowness change rate (%) on storage day 3 and storage day 6 compared to storage day 0 was calculated, as shown in Tables 8 and 9. Figure 5 shown.

[0119] [Table 7]

[0120]

[0121] [Table 8]

[0122]

[0123] * p<0.05, ** p<0.005

[0124] As shown in Table 7 and Figure 5 As shown in the figures, it was confirmed that the psicose syrup containing 0.025 wt % or more of psicose dimer prevented browning.

[0125] Example 11: Moisture Loss Prevention Effect of Psicose Dimer

[0126] To confirm the effectiveness of preventing moisture loss during long-term storage of a saccharide syrup based on the psicose dimer content, a psicose syrup with a solids content of 71% by weight was prepared by mixing the ingredients in the weight ratios listed in Table 9 using the same method as in Example 8. 10 g of the mixture was then dripped onto a dish and stored at 60°C for one day to promote moisture evaporation. After storage, the moisture content evaporated from the psicose syrup was analyzed using vacuum drying, and the moisture loss rate (%) within the saccharide syrup was calculated on storage day 1 compared to storage day 0, as shown in Table 10.

[0127] [Table 9]

[0128]

[0129] [Table 10]

[0130]

[0131] *p<0.05, **p<0.005

[0132] As shown in Table 10, based on an initial moisture content of 100%, it was confirmed that the higher the psicose dimer content, the slower the moisture loss. Specifically, it was found that when the psicose dimer content was 1.0 wt % or more, moisture loss was significantly prevented.

Claims

1. A composition comprising psicose dimer crystals or a dissolved solution thereof, wherein the psicose dimer crystals have an X-ray powder diffraction pattern comprising peaks at three or more positions selected from the group consisting of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° at 2θ diffraction angles in XRD analysis.

2. The composition according to claim 1, wherein the psicose dimer crystal has an X-ray powder diffraction pattern having peaks at positions including 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, and 18.14±0.5° in X-ray powder diffraction (XRD) analysis.

3. The composition according to claim 1, wherein the psicose dimer crystal has an X-ray powder diffraction pattern comprising peaks at positions including 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, and 19.34±0.5° in X-ray powder diffraction (XRD) analysis.

4. The composition according to claim 1, wherein the psicose dimer crystal has an X-ray powder diffraction pattern comprising peaks at positions including 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, and 7.76±0.5° in X-ray powder diffraction (XRD) analysis.

5. The composition according to claim 1, wherein the psicose dimer crystal has an X-ray powder diffraction pattern comprising peaks at positions including 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° in X-ray powder diffraction (XRD) analysis. The composition according to claim 1 , wherein the D-psicose dimer crystals have a melting point of 210±5° C. 7 . The composition according to claim 1 , wherein the solubility of the psicose dimer crystals in water is 5 g / 100 g to 20 g / 100 g.

8. The composition according to claim 1, wherein the molecular formula of the psicose dimer crystal is C 12 H 20 O 10 .

9. The composition according to claim 1, wherein the molecular weight of the psicose dimer crystals is 324.

11. 10 . The composition according to claim 1 , wherein the retention time of the psicose dimer analyzed by gas chromatography (GC) analysis is 11 to 13 minutes.

11. The composition according to any one of claims 1 to 10, wherein the composition is used to prevent or improve browning of psicose syrup.

12. The composition according to claim 11, wherein the prevention or improvement of browning is characterized by a yellowness change rate of -50% to 70% when the psicose syrup is stored at 60°C for 48 hours.

13. The composition according to claim 11, wherein the browning is caused by at least one selected from the group consisting of heat, pH, and storage time. The composition according to claim 11 , wherein the content of the psicose dimer is 0.025 wt % or more based on 100 wt % of solid content. The composition according to claim 11 , wherein the content of the psicose dimer is 0.025 wt % or more based on gas chromatography (GC) analysis.

16. The composition according to any one of claims 1 to 10, wherein the composition is used to prevent moisture loss of psicose syrup.

17. The composition according to claim 16, wherein the prevention of moisture loss is characterized in that the moisture content of the psicose syrup after storage at 60°C for 24 hours is 57 wt% or more, based on 100 wt% of the moisture content immediately after preparation. The composition according to claim 16 , wherein the content of the psicose dimer is 1 wt % or more based on 100 wt % of the solid content. The composition according to claim 16 , wherein the content of the psicose dimer is 1% by weight or more based on gas chromatography (GC) analysis.

20. A sugar syrup comprising Allulose; and Dictionary > English > psicose dimer crystals or a dissolved solution thereof, wherein the psicose dimer crystals have an X-ray powder diffraction pattern comprising peaks at three or more positions selected from the group consisting of 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° in X-ray powder diffraction (XRD) analysis. The saccharide syrup according to claim 20, wherein the saccharide syrup comprises 0.025 wt% or more of the psicose dimer based on 100 wt% of solid content. 22 . The saccharide syrup according to claim 20 , wherein the content of the psicose dimer measured by gas chromatography (GC) analysis is 0.025 wt % or more.

23. The saccharide syrup according to claim 20, wherein the psicose dimer crystals have an X-ray powder diffraction pattern having peaks at positions including 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, and 18.14±0.5° in X-ray powder diffraction (XRD) analysis.

24. The saccharide syrup according to claim 20, wherein the psicose dimer crystals have an X-ray powder diffraction pattern having peaks at positions including 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, and 19.34±0.5° in X-ray powder diffraction (XRD) analysis.

25. The saccharide syrup according to claim 20, wherein the psicose dimer crystals have an X-ray powder diffraction pattern having peaks at positions including 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, and 7.76±0.5° in X-ray powder diffraction (XRD) analysis.

26. The saccharide syrup according to claim 20, wherein the psicose dimer crystals have an X-ray powder diffraction pattern having peaks at positions including 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° in X-ray powder diffraction (XRD) analysis. The saccharide syrup according to claim 20 , wherein the melting point of the psicose dimer crystals is 210±5° C. The saccharide syrup according to claim 20, wherein the solubility of the psicose dimer crystals in water is 5 g / 100 g to 20 g / 100 g.

29. The saccharide syrup according to claim 20, wherein the content of psicose is 20 wt% to 99.975 wt% based on 100 wt% of the solid content.

30. The saccharide syrup of claim 20, wherein the saccharide syrup has a solids content of 20% to 90% by weight.

31. The saccharide syrup according to claim 20, wherein the psicose dimer is a preparation for preventing psicose from browning or a preparation for improving psicose from browning.

32. The saccharide syrup according to claim 20, wherein when the syrup is stored at 60°C for 48 hours, the yellowness change rate is -50% to 70%. The saccharide syrup according to claim 20, wherein the moisture content of the syrup after storage at 60°C for 24 hours is 57 wt% or more, based on 100 wt% of the moisture content immediately after preparation.

34. The saccharide syrup according to claim 20, wherein the syrup further comprises at least one selected from the group consisting of monosaccharides other than psicose, disaccharides, sugar alcohols, oligosaccharides, high intensity sweeteners, dietary fiber, protein, vitamins, seasonings, and colorants.

35. A food composition comprising the carbohydrate syrup according to any one of claims 20 to 34.

36. A method for preparing a saccharide syrup containing psicose, the method comprising the step of controlling the content of psicose dimer crystals or a dissolved solution thereof in the saccharide syrup containing psicose, the psicose dimer crystals having an X-ray powder diffraction pattern comprising peaks at three or more positions selected from the group consisting of 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° in X-ray powder diffraction (XRD) analysis.

37. The method according to claim 36, wherein the controlling step controls the content of the psicose dimer crystals or the dissolved solution thereof to be 0.025 wt% or more based on 100 wt% of the solid content of the saccharide syrup.

38. A method for preventing or improving browning of a saccharide syrup containing psicose, the method comprising the step of controlling the content of psicose dimer crystals or a dissolved solution thereof in the saccharide syrup containing psicose, the psicose dimer crystals having an X-ray powder diffraction pattern comprising peaks at three or more positions selected from the group consisting of 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° in X-ray powder diffraction (XRD) analysis.

39. The method according to claim 38, wherein the controlling step controls the content of the psicose dimer crystals or the dissolved solution thereof to be 0.025 wt% or more based on 100 wt% of the solid content of the saccharide syrup.

40. A method for preventing moisture loss in a saccharide syrup containing psicose, the method comprising the step of controlling a content of psicose dimer crystals or a dissolved solution thereof in the saccharide syrup containing psicose, the psicose dimer crystals having an X-ray powder diffraction pattern comprising peaks at three or more positions selected from the group consisting of 2θ diffraction angles of 15.51±0.5°, 17.66±0.5°, 18.14±0.5°, 19.34±0.5°, 7.76±0.5°, and 28.73±0.5° in X-ray powder diffraction (XRD) analysis.

41. The method according to claim 40, wherein the controlling step controls the content of the psicose dimer crystals or the dissolved solution thereof to be 1 wt% or more based on 100 wt% of the solid content of the saccharide syrup.

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