Allulose syrup with improved properties

Abstract

The present application relates to allulose syrups with improved properties.

Description

[Technical Field]

[0001] The present application relates to allulose syrups with improved properties. [Background technology]

[0002] Allulose is a rare sugar that is approximately 70% as sweet as sugar, and because it is not metabolized upon ingestion, it has a very low calorie content and is a functional sweetener that can prevent body fat gain and regulate blood sugar. Furthermore, despite having 60-70% of the sweetness of sugar, allulose has almost no calories and is highly soluble, making it expected to be used in a variety of foods.

[0003] When producing allulose, the product has a low allulose content, so it requires purification and concentration processes. However, concentrated syrup has limited application, so there is a high demand for crystals or powder, but allulose has low crystallinity and is difficult to crystallize. Therefore, allulose is currently mainly provided in the form of allulose-rich syrup.

[0004] In addition, allulose syrup has a problem of being prone to browning, and it is necessary to provide allulose syrup that can prevent browning or has high color stability and in which browning is delayed or reduced. Summary of the Invention [Problem to be solved by the invention]

[0005] One example of the present application provides a sugar syrup composition, such as allulose syrup, containing allulose dimer crystals or a dissolved product thereof having a specific diffraction angle pattern.

[0006] An additional example of the present application provides an agent for preventing or improving browning of allulose syrup, comprising allulose dimer crystals having a specific diffraction angle pattern or a solution thereof, for preventing, inhibiting, reducing, or improving browning of allulose syrup.

[0007] Yet another example of the present application relates to a method for preventing or improving browning of allulose syrup, which comprises a step of adjusting the content of allulose dimer crystals having a specific diffraction angle pattern or a dissolved product thereof in allulose syrup.

[0008] Yet another example of the present application relates to a method for reducing the rate of yellowness change of allulose syrup, which includes a step of adjusting the content of allulose dimer crystals having a specific diffraction angle pattern or a dissolved product thereof in the allulose syrup.

[0009] Yet another example of the present application provides an agent for preventing moisture loss from allulose syrup, which comprises allulose dimer crystals having a specific diffraction angle pattern or a dissolved product thereof, for improving the moisture retention of allulose syrup.

[0010] Yet another example of the present application relates to a method for preventing moisture loss from allulose syrup, comprising a step of adjusting the content of allulose dimer crystals having a specific diffraction angle pattern or a melt thereof in allulose syrup. [Means for solving the problem]

[0011] One example of the present application relates to a composition for preventing or improving browning of allulose syrup or a composition for preventing moisture loss, comprising allulose dimer crystals or a dissolve thereof, which have an X-ray powder diffraction pattern including at least three peaks with 2-theta 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.

[0012] Yet another example of the present application relates to a sugar syrup containing allulose and allulose dimer crystals or a dissolution product thereof, which have an X-ray powder diffraction pattern including at least three peaks at 2-theta 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. [Effects of the Invention]

[0013] A composition for preventing or improving browning of allulose syrup, a composition for preventing moisture loss, or sugar syrup according to an example of the present application includes allulose dimer crystals or a dissolved product thereof according to an example of the present application, and can prevent or reduce browning of allulose syrup that occurs over storage time and minimize moisture loss contained in allulose syrup. [Brief explanation of the drawings]

[0014] [Figure 1] 1 is a graph showing the solubility of allulose dimer crystals according to an example of the present application. [Figure 2] 1 is a diagram showing the results of gas chromatography (GC) analysis of allulose dimer crystals according to an example of the present application. [Figure 3] 1 is a diagram showing a change in yellowness of a sugar syrup according to an example of the present application. [Figure 4] 1 is a diagram showing the change in yellowness of a saccharide syrup according to an example of the present application, broken down by the content of allulose dimer crystals. [Figure 5] 1 is a diagram showing a change in yellowness when a sugar syrup according to an example of the present application is stored for a long period of time. DETAILED DESCRIPTION OF THE INVENTION

[0015] The present application is described in more detail below. The term "allulose dimer" in the present application refers to a molecule in which two allulose molecules are chemically condensed. Specifically, the allulose dimer may be a substance having 44.600 wt% carbon, 5.907 wt% hydrogen, and 53.556 wt% oxygen, and has the molecular formula C 12 H 20 O 10 and allulose dimer with a molecular weight of 324.11.

[0016] The allulose dimer of the present application may be in the form of an allulose dimer crystal or a dissolved form thereof. The allulose dimer crystal may have peaks at at least three of the following 2-theta diffraction angles in X-ray powder diffraction (XRD) analysis: 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 allulose dimer crystal may have peaks at at least three of the following 2-theta diffraction angles in X-ray powder diffraction (XRD) analysis: 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°.

[0017] For example, the allulose dimer crystals may have an X-ray powder diffraction (XRD) pattern including peaks at 2-theta 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°.

[0018] For example, the allulose dimer crystals may have an X-ray powder diffraction (XRD) pattern including peaks at 2-theta 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°.

[0019] The peak may have 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 in the results of X-ray powder diffraction (XRD) analysis. The relative intensity of the peak is expressed as a relative numerical percentage of the intensity of each peak, with the intensity of the peak with the greatest intensity being 100%.

[0020] Among the peaks, several peaks in descending order of relative intensity, or peaks with a relative intensity equal to or greater than a certain value, may be major peaks that determine the crystalline form. For example, the major peaks may be 1 to 6, 1 to 5, 1 to 4, 1 to 3, or 1 to 2 peaks with the highest relative intensities. For example, the major peaks may be peaks 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.

[0021] Therefore, the diffraction angle of the allulose dimer crystal may be the diffraction angle of a major peak having a high relative intensity in X-ray powder diffraction (XRD) analysis, and the diffraction angles may be listed in order from the diffraction angle having the highest relative intensity in X-ray powder diffraction (XRD) analysis.

[0022] For example, the allulose dimer crystals have, in X-ray powder diffraction (XRD) analysis, 2-theta diffraction angles of 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. 0.34±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°. Specifically, the allulose dimer crystals have, in order of relative peak intensity from highest to lowest in X-ray powder diffraction (XRD) analysis, 2-theta diffraction angles of 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. 0.34±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°.

[0023] For example, the allulose dimer crystal may have an X-ray powder diffraction pattern in which the peak with the highest relative intensity is located at a 2-theta diffraction angle of 15.51±0.5° or 15.51±0.2° in X-ray powder diffraction (XRD) analysis.

[0024] For example, the allulose dimer crystals may have an X-ray powder diffraction pattern in which the two peaks with the highest relative intensities in X-ray powder diffraction (XRD) analysis are located at 2-theta diffraction angles of 15.51±0.5° and 17.66±0.5°; or 15.51±0.2° and 17.66±0.2°.

[0025] For example, the allulose dimer crystals may have an X-ray powder diffraction pattern in which the three peaks with the highest relative intensities in X-ray powder diffraction (XRD) analysis are located at 2-theta diffraction angles of 1, 5.51±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°.

[0026] The allulose dimer crystals may have a melting point of 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.

[0027] The allulose dimer crystals may have a solubility in water of 5 to 20 g / 100 g, 5 to 15 g / 100 g, 5 to 12 g / 100 g, 5 to 10 g / 100 g, 7 to 20 g / 100 g, 7 to 15 g / 100 g, 7 to 12 g / 100 g, 7 to 10 g / 100 g, 8 to 20 g / 100 g, 8 to 15 g / 100 g, 8 to 12 g / 100 g, 8 to 10 g / 100 g, 9 to 20 g / 100 g, 9 to 15 g / 100 g, 9 to 12 g / 100 g, or 9 to 10 g / 100 g.

[0028] The allulose dimer may have a retention time of 11 to 13 minutes as analyzed by gas chromatography (GC) analysis.

[0029] One example of the present application relates to a composition for preventing or improving browning of allulose syrup, comprising the allulose dimer crystals or a solution thereof. The allulose dimer crystals or a solution thereof may be contained in allulose syrup and prevent or improve browning of the allulose syrup. Thus, yet another example of the present application relates to an allulose syrup containing the allulose dimer crystals or a solution thereof, in which browning is prevented or improved.

[0030] In the present application, the term "anti-browning" can be used to mean inhibiting or delaying the occurrence of browning. The terms "anti-browning," "inhibiting browning," and "delaying browning" refer to a lower rate of increase in the browning level (e.g., yellowness index) compared to immediately after production compared to a control group.

[0031] In the present application, the term "improved browning" can be used to mean a reduction in the degree of browning, for example, a reduction in yellowness. The improved browning means that the browning level (e.g., yellowness index value) is lower than that immediately after production.

[0032] The browning may be caused by one or more factors selected from the group consisting of heat, pH, and storage time. The browning may be non-enzymatic browning reactions, such as the aminocarbonyl reaction, melanoidin reaction, and Maillard reaction, which occur when an amino group and a carbonyl group coexist. These include browning due to the production of osones, browning due to the production of intermediates such as unsaturated 3,4-dieoxyosone, browning due to the reaction of furfural-generated cyclic substances, including hydroxymethyl furfural (HMF), with amino acids to form melanoidins, and brown pigments due to sugar decomposition products.

[0033] Yet another example of the present application relates to a composition for preventing moisture loss from allulose syrup, comprising the allulose dimer. The allulose dimer crystals or a solution thereof may be contained in allulose syrup to prevent moisture loss from the allulose syrup. Thus, yet another example of the present application relates to an allulose syrup containing the allulose dimer crystals or a solution thereof, from which moisture loss has been prevented.

[0034] In the present application, the term "prevention of water loss" can be used to mean suppressing or delaying the loss of water contained in a sugar syrup, such as allulose syrup. The prevention of water loss means that the amount of water loss is lower compared to a control group immediately after production.

[0035] According to one embodiment of the present application, the allulose dimer crystals or their dissolution product may contain 0.025% by weight or more, 0.03% by weight or more, 0.035% by weight or more, 0.04% by weight or more, 0.045% by weight or more, 0.05% by weight or more, 0.055% by weight or more, 0.06% by weight or more, 0.065% by weight or more, 0.07% by weight or more, 0.075% by weight or more, 0.08% by weight or more, 0.085% by weight or more, based on 100% by weight of the solid content of the allulose syrup. The allulose dimer crystals or their solution may contain 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 allulose dimer crystals or their solution may be measured by gas chromatography (GC) analysis.

[0036] The content of the allulose dimer crystals or their dissolved product may be 20% by weight or less, 19% by weight or less, 18% by weight or less, 17% by weight or less, 16% by weight or less, 15% by weight or less, 14% by weight or less, 13% by weight or less, 12% by weight or less, 11% by weight or less, or 10% by weight or less, based on 100% by weight of the solid content of the allulose syrup.

[0037] Yet another example of the present application relates to a sugar syrup comprising allulose and allulose dimer crystals or a solution thereof, which have an X-ray powder diffraction pattern including at least three peaks in 2-theta 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 allulose dimer crystals or the solution thereof are the same as those described above.

[0038] The solid content of the sugar syrup is 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 70% by weight, The amount may be 40 to 90% by weight, 40 to 85% by weight, 40 to 80% by weight, 40 to 75% by weight, 40 to 70% by weight, 50 to 90% by weight, 50 to 85% by weight, 50 to 80% by weight, 50 to 75% by weight, 50 to 70% by weight, 60 to 90% by weight, 60 to 85% by weight, 60 to 80% by weight, 60 to 75% by weight, or 60 to 70% by weight.

[0039] The saccharide syrup contains the allulose dimer or its solution in an amount of 0.025% by weight or more, 0.03% by weight or more, 0.035% by weight or more, 0.04% by weight or more, 0.045% by weight or more, 0.05% by weight or more, 0.055% by weight or more, 0.06% by weight or more, 0.065% by weight or more, 0.07% by weight or more, 0.075% by weight or more, 0.08% by weight or more, 0.085% by weight or more, based on a solid content of 100% by weight. It may contain 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 allulose dimer crystals or their dissolution product may be measured by gas chromatography (GC) analysis.

[0040] The saccharide syrup may contain the allulose dimer or its dissolved product in an amount of 20% by weight or less, 19% by weight or less, 18% by weight or less, 17% by weight or less, 16% by weight or less, 15% by weight or less, 14% by weight or less, 13% by weight or less, 12% by weight or less, 11% by weight or less, or 10% by weight or less, based on a solid content of 100% by weight.

[0041] The saccharide syrup may be one that has been prevented from browning, and the prevention of browning is the same as that described above. In the examples of the present application, the change in yellowness of the saccharide syrup containing the allulose dimer or its solution according to an example of the present application was examined, and it was found that the increase in yellowness was suppressed compared to the control group.

[0042] Specifically, after storing a sugar syrup according to one example of the present application at 60°C for 48 hours, the rate of change in yellowness measured immediately after production relative to a standard of 100% yellowness may be 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.

[0043] Specifically, after storing a sugar syrup according to one example of the present application at 60°C for three days, the rate of change in yellowness measured immediately after production relative to a standard of 100% yellowness 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.

[0044] Specifically, after storing a sugar syrup according to one example of the present application at 60°C for 6 days, the rate of change in yellowness measured immediately after production relative to a standard of 100% yellowness may be 1400% or less, 1350% or less, 1300% or less, 1200% or less, or 1100% or less.

[0045] In one example of the present application, the saccharide syrup may be one that has been improved in terms of browning, and the improvement in browning is the same as that described above. In the examples of the present application, the change in yellowness of the saccharide syrup containing allulose dimer or its solution according to one example of the present application was confirmed, and the yellowness was found to be reduced compared to the initial value.

[0046] Specifically, after storing a sugar syrup according to one example of the present application at 60°C for 48 hours, the rate of change in yellowness measured immediately after production relative to a standard of 100% yellowness may be -5% or less, -10% or less, -15% or less, -18% or less, -20% or less, -25% or less, or -30% or less.

[0047] The rate of change in yellowness may be calculated by [(measured yellowness)-(yellowness immediately after production)] / (yellowness immediately after production)×100(%).

[0048] For example, the sugar syrup according to one example of the present application may have a yellowness change rate of −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% relative to a standard yellowness of 100% measured immediately after production after storage at 60°C for 48 hours.

[0049] The saccharide syrup may be one that has been prevented from losing moisture, and the prevention of moisture loss is the same as that described above. In the examples of the present application, the change in moisture content of the saccharide syrup containing allulose dimer or its solution according to an example of the present application was confirmed, and the amount of moisture loss was found to be less than that of the control group.

[0050] Specifically, the moisture content of a sugar syrup according to one example of the present application after storage at 60°C for one day may be 57% by weight or more, 58% by weight or more, 59% by weight or more, 60% by weight or more, 61% by weight or more, 62% by weight or more, 63% by weight or more, 64% by weight or more, 65% by weight or more, 66% by weight or more, 67% by weight or more, 68% by weight or more, 69% by weight or more, or 70% by weight or more, based on a moisture content of 100% immediately after production.

[0051] The sugar syrup may further contain one or more selected from the group consisting of monosaccharides excluding allulose, disaccharides, sugar alcohols, oligosaccharides, high-intensity sweeteners, dietary fiber, proteins, vitamins, flavorings, and colorants.

[0052] The monosaccharide may be one or more selected from the group consisting of fructose, glucose, and galactose.

[0053] The disaccharide may be one or more selected from the group consisting of sugar, lactose, and maltose.

[0054] The sugar alcohol may be at least one selected from the group consisting of xylitol, erythritol, sorbitol, maltitol, mannitol, isomalt, and lactitol, but is not limited thereto.

[0055] The high-intensity sweetener may be at least one selected from the group consisting of stevioglucoside, stevia extract, aspartic acid, aspartame, steviaside, enzyme-treated stevia, sucralose, saccharin, rebaudioside, monk fruit, mogroside, acesulfame calcium, thaumatin, brazzein, monellin, miraculin, and pentadin, but is not limited thereto.

[0056] The dietary fiber may include water-soluble dietary fiber and / or insoluble dietary fiber. The water-soluble dietary fiber may be one or more selected from the group consisting of arabinoxylan, fructan, inulin, pectin, alginic acid, agar, raffinose, polydextrose, maltodextrin, and resistant maltodextrin. The insoluble dietary fiber may be one or more selected from the group consisting of cellulose, chitin, hemicellulose, lignin, xanthan gum, and resistant starch, but is not limited thereto.

[0057] The protein may include, but is not limited to, animal protein and / or vegetable protein.

[0058] The vitamins may include, but are not limited to, fat-soluble vitamins and / or water-soluble vitamins.

[0059] The type of flavor is not particularly limited as long as it is an edible flavor, and may be, for example, one or more selected from strawberry, vanilla, chocolate, green tea, apple, grape, blueberry, raspberry, cranberry, watermelon, orange, banana, caramel, pistachio, milk, yogurt, lemon, chestnut, peanut, coffee, black tea, melon, grain, sweet potato, pear, red bean, walnut, almond, peach, cherry, hotteok, tomato, soda, cola, pumpkin, and corn.

[0060] The type of pigment is not particularly limited as long as it is an edible pigment, and may be one or more pigments selected from the group consisting of blue pigments such as gardenia blue pigment and spirulina pigment, yellow pigments such as gardenia yellow pigment, turmeric pigment, annatto pigment, and carotene, red pigments such as beet pigment, cochineal pigment, lac pigment, red koji red pigment, anthocyanin, and paprika extract pigment, purple pigments such as red cabbage pigment, purple sweet potato pigment, and grape skin extract pigment, brown pigments such as cacao pigment and caramel pigment, and green pigments such as green spirulina and chlorella pigment, etc. A variety of pigments can be produced by combining multiple types of pigments as described above.

[0061] Yet another example of the present application relates to a method for producing a sugar syrup containing allulose, the method comprising a step of adjusting the content of allulose dimer crystals or a dissolved product thereof in the allulose-containing sugar syrup, the allulose-containing crystals having an X-ray powder diffraction pattern including at least three peaks with 2-theta 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.

[0062] Yet another example of the present application relates to a method for preventing or ameliorating browning of allulose-containing sugar syrup, the method comprising a step of adjusting the content of allulose dimer crystals or a dissolved product thereof in the allulose-containing sugar syrup, the allulose-containing sugar syrup having an X-ray powder diffraction pattern including at least three peaks at 2-theta 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] Yet another example of the present application relates to a method for preventing water loss from an allulose-containing sugar syrup, the method comprising a step of adjusting the content of allulose dimer crystals or their dissolved products in the allulose-containing sugar syrup, the allulose-containing sugar syrup having an X-ray powder diffraction pattern including at least three peaks with 2-theta 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] The adjusting step may be carried out by adjusting the content of the allulose dimer crystals or their dissolved product to 0.025% by weight or more, 0.03% by weight or more, 0.035% by weight or more, 0.04% by weight or more, 0.045% by weight or more, 0.05% by weight or more, 0.055% by weight or more, 0.06% by weight or more, 0.065% by weight or more, 0.07% by weight or more, 0.075% by weight or more, 0.08% by weight or more, 0.085% by weight or more, based on the solid content of the saccharide syrup (100% by weight). %, 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 dissolved substance may be the content of the allulose dimer crystals excluding the solvent.

[0065] The adjusting step may include, for example, a step of adding the allulose dimer crystals or a dissolved product thereof to the saccharide syrup, or a step of increasing the content of the allulose dimer crystals or a dissolved product thereof contained in the saccharide syrup.

[0066] The present application will be described in more detail below with reference to the following examples, but these examples are for illustrative purposes only and are not intended to limit the scope of the present application. [Example]

[0067] Example 1: Isolation of allulose dimer crystals Allulose syrup having an allulose purity of 95% by weight or more and an allulose solid content of 68 to 72% by weight was titrated to pH 3.5 or less and stored at 35°C until the allulose content decreased to 80% by weight or less. When the allulose content fell below 80 wt%, the allulose syrup was refrigerated to promote the crystallization of allulose dimer. If visual inspection revealed the formation of allulose dimer crystals, they were separated from the syrup using ethanol. The separated allulose dimer crystals were dried in a dry oven to evaporate the ethanol, and the peak elution was monitored by HPLC. The purified product was isolated by fractionation based on the detector signal or retention time. Specifically, HPLC analysis was performed using a Biorad HPX 87C column set to 80°C with an RI detector and a mobile phase of distilled water (DW) at 0.6 mL / min. This yielded pure allulose dimer (purity 99 wt%), which was used for subsequent experiments.

[0068] Example 2: Elemental analysis of allulose dimer crystals Elemental analysis was carried out using an elemental analyzer to analyze the material of the allulose dimer crystals obtained in Example 1. A sample of 1.8 mg was used, and the analysis temperature was set at 1,150°C. Sulfanilic acid and benzoic acid were used as standards. Analysis revealed that the material had C44.600, H5.907, and O53.556 wt%, and the molecular formula was C 12 H 20 O 10 The molecular weight was confirmed to be 324.11.

[0069] Example 3: Mass spectrometry of allulose dimer crystals A high resolution mass spectrometer was used to analyze the allulose dimer crystals obtained in Example 1. The ionization conditions for the analysis were ion mode FAB (Fast Atom Bombardment). As a result of the mass spectrometry, the molecular weight of allulose dimer was confirmed to be 324.11, and the same analytical results as in Example 2 were confirmed.

[0070] Example 4: X-ray Diffraction (XRD) Analysis The allulose dimer crystals obtained in Example 1 were subjected to X-ray diffraction analysis according to the following specific analysis conditions, and the top 6 peaks (relative intensity%) from the X-ray diffraction analysis results of the allulose dimer crystals were selected and shown in Table 1.

[0071] [Table 1]

[0072] As shown in Table 1, the allulose dimer crystals obtained in Example 1 had the following peak 2-theta values ​​in the powder X-ray spectroscopy spectrum: the top three peaks had 2-theta values ​​of 15.51°, 17.66°, and 18.14°; the top four peaks had 2-theta values ​​of 15.51°, 17.66°, 18.14°, and 19.34°; the top five peaks had 2-theta values ​​of 15.51°, 17.66°, 18.14°, 19.34°, and 7.76°; and the top six peaks had 2-theta values ​​of 15.51°, 17.66°, 18.14°, 19.34°, 7.76°, and 28.73°.

[0073] Example 5: Melting point analysis of allulose dimer crystals (DSC analysis) The melting point of the allulose dimer crystals obtained in Example 1 was confirmed using a differential scanning calorimeter (DSC). The analysis temperature range was -10°C to 250°C, and 4 mg of the allulose dimer crystal sample was quantitatively analyzed. As a result of the melting point analysis, the melting point of the allulose dimer crystals was confirmed to be about 210.7°C.

[0074] Example 6: Solubility analysis of allulose dimer crystals To analyze the solubility of the allulose dimer crystals obtained in Example 1, the solubility was evaluated at temperatures of 25°C to 80°C using water as a solvent. As a result of analyzing the solubility in water, allulose dissolved at 34 g / 100 g (water) at a solvent temperature of 25°C, while allulose dimer crystals dissolved at 9.2 g / 100 g (water). The solubility graph of allulose and allulose dimer crystals is shown in Figure 1.

[0075] Example 7: GC analysis of allulose dimer crystals 100 mg to 300 mg of the allulose dimer crystal sample obtained in Example 1 was titrated, and 30 mg of phenyl beta-D-glucopyranoside was added to 10 ml of 100 ml of pyridine and mixed with the allulose dimer crystal sample. 0.5 ml of the mixture was placed in a 2 ml to 4 ml reagent bottle and evaporated to dryness under a nitrogen stream. 0.5 ml of a solution prepared by mixing 4 g of hydroxylamine hydrochloride in 100 ml of pyridine was added to the evaporated and dried sample, stirred thoroughly to dissolve the dried material, and then left at 70 °C for 40 minutes. After 40 minutes, the reaction mixture was left at room temperature, and 0.4 ml of BSTFA and 0.1 ml of N-trimethylsilylimidazole (TSIM) were added. The cap was then recapped and heated at 70 °C for 30 minutes. After cooling to room temperature, the sample was used for GC analysis. The GC analysis conditions are as shown in Table 2, and the GC analysis dimer content analysis formula is as follows: Dimer (%) = (GC peak surface area of ​​substance at 11-13 min / surface area of ​​internal standard peak) × (weight of internal standard added during sample pretreatment / sample weight) × (100 / dimer reaction coefficient) -Dimer reactivity coefficient: 1.15

[0076] [Table 2]

[0077] The results of GC analysis of the allulose dimer crystals are shown in Figure 2. The GC analysis confirmed that a peak was detected at 11 to 13 minutes.

[0078] Example 8: Anti-browning effect of allulose dimer (1) The effect of the allulose dimer obtained in Example 1 on browning of allulose syrup was confirmed. Allulose crystals with a purity of 99.99% and allulose dimer crystals were mixed in the weight ratio shown in Table 3 to prepare liquid samples with a solid content of 68 wt%. Each sample was stored at 60°C, and samples were taken at 0 and 48 hours of storage. Yellowness was analyzed at 420 nm using a spectrophotometer at a solid content of 30 wt%. The change in yellowness (%) at 48 hours compared to 0 hours was calculated using the following formula 1, and is shown in Table 4 and Figure 3: Yellowness change rate (%) = [(48h yellowness) - (0h yellowness)] / (0h yellowness) x 100%

[0079] [Table 3]

[0080] [Table 4]

[0081] As shown in Table 4 and Figure 3, a comparison of the progression of browning depending on the allulose dimer content according to an example of the present application confirmed that samples containing 0.05 wt% or more of allulose dimer showed a slower browning rate than the control without addition, and samples containing 0.4 wt% or more of allulose dimer showed no or even a lower change in yellowness compared to time 0. Therefore, allulose syrup containing allulose dimer crystals or their solution at a certain concentration or higher according to an example of the present application had the effect of delaying browning.

[0082] Example 9: Browning prevention effect of allulose dimer crystals (2) To further confirm the browning prevention effect depending on the allulose dimer crystal content, allulose syrup was prepared in the same manner as in Example 8, with the allulose dimer crystal content divided into 0.01 wt% increments according to the weight ratios shown in Table 5, and browning was accelerated by storing at 60°C for 48 hours in the same manner as in Example 8. After 48 hours, the allulose syrup was adjusted to a concentration of 68 wt%, and the yellowness was analyzed at 420 nm using a spectrophotometer. The change in yellowness (%) at 48 hours compared to 0 hours was calculated according to Equation 1 and is shown in Table 6 and FIG. 4.

[0083] [Table 5]

[0084] [Table 6]

[0085] As shown in Table 6 and FIG. 4, allulose syrup containing 0.03 wt % or more of allulose dimer prevented browning, and in particular, reduced yellowness compared to the control.

[0086] Example 10: Browning prevention effect of allulose dimer during long-term storage To confirm the browning retardation effect depending on the allulose dimer content during long-term storage of sugar syrup, allulose syrup with a solid content of 71 wt% was prepared in the same manner as in Example 8 using the weight ratios listed in Table 7, and stored at 60°C for 6 days to accelerate browning. After 3 and 6 days of storage, the allulose 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 days 3 and 6 compared to day 0 was calculated and shown in Table 8 and FIG. 5.

[0087] [Table 7]

[0088] [Table 8]

[0089] As shown in Table 7 and FIG. 5, it was confirmed that allulose syrup containing 0.025 wt % or more of allulose dimer was prevented from browning.

[0090] Example 11: Effect of allulose dimer on preventing water loss To confirm the effect of preventing moisture loss depending on the allulose dimer content during long-term storage of saccharide syrup, allulose syrup with a solid content of 71 wt % was prepared by mixing the ingredients in the weight ratios shown in Table 9 in the same manner as in Example 8, and 10 g of the allulose syrup was placed in a dish and stored at 60°C for 1 day to induce moisture evaporation. After storage, the amount of moisture evaporated from the allulose syrup was analyzed using a vacuum drying method, and the moisture loss rate (%) inside the saccharide syrup on day 1 of storage compared to day 0 was calculated and is shown in Table 10.

[0091] [Table 9]

[0092] [Table 10]

[0093] As shown in Table 10, the moisture loss was measured based on an initial moisture content of 100%. It was confirmed that the moisture loss was delayed as the content of allulose dimer according to an example of the present application increased. In particular, it was found that moisture loss was significantly prevented when the allulose dimer content was 1.0 wt% or more.

Claims

1. A composition comprising allulose dimer crystals or a dissolution product thereof, which has an X-ray powder diffraction pattern including peaks at at least three of the following 2-theta diffraction angles in X-ray powder diffraction (XRD) analysis: 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°.

2. The allulose dimer crystals have an X-ray powder diffraction pattern including peaks at 2-theta diffraction angles of 15.51±0.5°, 17.66±0.5°, and 18.14±0.5° in X-ray powder diffraction (XRD) analysis. The composition of claim 1.

3. The allulose dimer crystals according to claim 1, wherein the allulose dimer crystals have an X-ray powder diffraction pattern including peaks at 2-theta 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 allulose dimer crystals according to claim 1, wherein the allulose dimer crystals have an X-ray powder diffraction pattern including peaks at 2-theta 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 allulose dimer crystals according to claim 1, wherein the allulose dimer crystals have an X-ray powder diffraction pattern including peaks at 2-theta 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.

6. The composition according to claim 1, wherein the allulose dimer crystals have a melting point of 210±5°C.

7. The composition according to claim 1, wherein the allulose dimer crystal has a solubility in water of 5 to 20 g / 100 g.

8. The molecular formula of the allulose dimer crystal is C 12 H 20 O 10 2. The composition of claim 1, wherein:

9. The composition of claim 1, wherein the molecular weight of the allulose dimer crystal is 324.

11.

10. The composition according to claim 1, wherein the allulose dimer has a retention time of 11 to 13 minutes when analyzed by gas chromatography (GC).

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

12. The composition according to claim 11, wherein the browning prevention or improvement is achieved by reducing the yellowness index by -50% to 70% when the allulose syrup is stored at 60°C for 48 hours.

13. The composition of claim 11, wherein the browning is caused by one or more selected from the group consisting of heat, pH, and storage time.

14. The composition according to claim 11, wherein the allulose dimer is contained in an amount of 0.025 wt% or more based on 100 wt% of the solid content.

15. The composition according to claim 11, wherein the allulose dimer is contained in an amount of 0.025 wt% or more according to gas chromatography (GC) analysis.

16. The composition according to any one of claims 1 to 10, wherein the composition is for preventing moisture loss from allulose syrup.

17. The composition according to claim 16, wherein the moisture loss is prevented by storing the allulose syrup at 60°C for 24 hours so that the moisture content is 57% by weight or more based on 100% by weight of the moisture content immediately after production.

18. The composition according to claim 16, wherein the allulose dimer is contained in an amount of 1 wt% or more based on 100 wt% of the solid content.

19. The composition according to claim 16, wherein the allulose dimer is contained in an amount of 1% by weight or more according to gas chromatography (GC) analysis.

20. A sugar syrup comprising allulose and allulose dimer crystals or a dissolution product thereof, which have an X-ray powder diffraction pattern including peaks at at least three positions selected from the following 2-theta diffraction angles in X-ray powder diffraction (XRD) analysis: 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°.

21. The saccharide syrup according to claim 20, wherein the saccharide syrup contains the allulose dimer in an amount of 0.025% by weight or more, based on a solid content of 100% by weight.

22. The saccharide syrup according to claim 20, wherein the content of allulose dimer measured by gas chromatography (GC) analysis is 0.025% by weight or more.

23. The allulose dimer crystals according to claim 20, wherein the allulose dimer crystals have an X-ray powder diffraction pattern including peaks at 2-theta 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 allulose dimer crystals have an X-ray powder diffraction pattern including peaks at 2-theta 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 allulose dimer crystals according to claim 20, wherein the allulose dimer crystals have an X-ray powder diffraction pattern including peaks at 2-theta 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 allulose dimer crystals have an X-ray powder diffraction pattern including peaks at 2-theta 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.

27. 21. The saccharide syrup according to claim 20, wherein the allulose dimer crystals have a melting point of 210±5°C.

28. The saccharide syrup according to claim 20, wherein the allulose dimer crystals have a solubility in water of 5 to 20 g / 100 g.

29. The sugar syrup according to claim 20, wherein the allulose content is 20 to 99.975% by weight, based on a solid content of 100% by weight.

30. 21. The sugar syrup according to claim 20, wherein the solids content of the sugar syrup is 20 to 90% by weight.

31. The saccharide syrup according to claim 20, wherein the allulose dimer is an agent for preventing or improving browning of allulose.

32. The saccharide syrup according to claim 20, wherein the rate of change in yellowness when the syrup is stored at 60°C for 48 hours is -50% to 70%.

33. The sugar syrup according to claim 20, wherein the moisture content of the syrup after storage at 60°C for 24 hours is 57% by weight or more based on the moisture content of 100% by weight immediately after production.

34. The sugar syrup according to claim 20, further comprising one or more selected from the group consisting of monosaccharides excluding allulose, disaccharides, sugar alcohols, oligosaccharides, high-intensity sweeteners, dietary fiber, proteins, vitamins, flavorings, and colorants.

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

36. A method for producing allulose-containing sugar syrup, comprising a step of adjusting the content of allulose dimer crystals or a dissolved product thereof in the allulose-containing sugar syrup, the allulose-containing crystals having an X-ray powder diffraction pattern including peaks at at least three positions selected from the 2-theta 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 adjusting step adjusts the content of the allulose dimer crystals or their dissolved product to 0.025% by weight or more based on 100% by weight of the solid content of the saccharide syrup.

38. A method for preventing or improving browning of allulose-containing sugar syrup, comprising a step of adjusting the content of allulose dimer crystals or a dissolved product thereof in the allulose-containing sugar syrup, the allulose dimer crystals having an X-ray powder diffraction pattern including peaks at at least three positions selected from the following 2-theta diffraction angles in X-ray powder diffraction (XRD) analysis: 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°.

39. The method according to claim 38, wherein the adjusting step adjusts the content of the allulose dimer crystals or their dissolved product to 0.025% by weight or more based on 100% by weight of the solid content of the saccharide syrup.

40. A method for preventing water loss from an allulose-containing sugar syrup, comprising the step of adjusting the content of allulose dimer crystals or their dissolved products in the allulose-containing sugar syrup, the allulose-containing crystals having an X-ray powder diffraction pattern including peaks at at least three of the following 2-theta diffraction angles in X-ray powder diffraction (XRD) analysis: 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°.

41. The method according to claim 40, wherein the adjusting step adjusts the content of the allulose dimer crystals or their dissolved product to 1% by weight or more based on 100% by weight of the solid content of the saccharide syrup.

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