Crystallinity imparting agent

Abstract

To provide a novel use of cyclic tetrasaccharide having a cyclic structure composed of four α-D-glucopyranose.SOLUTION: Provided are a crystallinity imparting agent including cyclic tetrasaccharide having a cyclic structure composed of four α-D-glucopyranose, a composition including the crystallinity imparting agent, a method for preparing the composition, and a method for imparting crystallinity to an object.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a novel use of a cyclotetrasaccharide having a cyclic structure composed of four α-D-glucopyranose units as a crystallinity-imparting agent, and also to a composition containing the cyclotetrasaccharide for such use. The present invention also relates to a method for preparing a composition containing the cyclotetrasaccharide for such use, and a method for imparting crystallinity to a subject. [Background technology]

[0002] Among cyclotetrasaccharides (hereinafter referred to as "cyclotetrasaccharides") having a cyclic structure composed of four α-D-glucopyranose units, cyclotetrasaccharides having the structure represented by cyclo{→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→} are cyclic carbohydrates composed of four glucose molecules, and were discovered by Cote in 1994 (Non-Patent Document 1). In the 2000s, a method for producing cyclotetrasaccharides using enzymes derived from soil microorganisms was established (Patent Documents 1 and 2). The establishment of this production method led to the development of cyclotetrasaccharides for industrial use, and the following properties have been revealed: low color (Patent Documents 1 and 2), low calorie content (Patent Documents 1 and 2), dietary fiber content (Patent Documents 1 and 2), radical production inhibitory activity (Patent Document 3), lipid regulating activity (Patent Document 4), and mineral absorption promoting activity (Patent Document 5). The utilization of these properties is now known. However, it is not known that cyclotetrasaccharide has the property of imparting crystallinity to things containing it, nor is there any known application that utilizes this property. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2002 / 010361 [Patent Document 2] International Publication No. 2001 / 903338 [Patent Document 3] International Publication No. 2004 / 020552 [Patent Document 4] International Publication No. 2004 / 899964 [Patent Document 5] International Publication No. 2005 / 007171 [Patent Document 6] International Publication No. 2021 / 066159 Prior Non-Patent Document

[0004] [Non-Patent Document 1] European Journal of Biochemistry, Vol. 226, pp. 641-648 (1994) Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide a novel use of a cyclic tetrasaccharide having a cyclic structure composed of four α-D-glucopyranose units as a crystallization-imparting agent. [Means for solving the problem]

[0006] The present inventors have discovered that crystallinity can be imparted to a target by including a cyclic tetrasaccharide having a ring structure composed of four α-D-glucopyranose units in the target, and have completed the present invention. Specifically, the present invention provides the following crystallinity-imparting agents, compositions containing the crystallinity-imparting agents, methods for preparing the compositions, and methods for imparting crystallinity to a target. [1] A crystallinity-imparting agent characterized by containing a cyclic tetrasaccharide, wherein the cyclic tetrasaccharide has a cyclic structure composed of four α-D-glucopyranose units. [2] The crystallinity-imparting agent according to [1] above, wherein the cyclic tetrasaccharide is a cyclic tetrasaccharide having a structure represented by cyclo{→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→}. [3] The crystallinity imparting agent according to [1] or [2], wherein the cyclic tetrasaccharide is cyclonigerosyl nigerose pentahydrate crystal. [4] The crystallinity imparting agent according to any one of [1] to [3], wherein the cyclic tetrasaccharide is contained in an amount of 40 to 100 mass% in terms of solid content relative to the total mass of the crystallinity imparting agent. [5] A composition comprising the crystallinity imparting agent according to any one of [1] to [4] above. [6] The composition according to [5], wherein the cyclotetrasaccharide is contained in a mass ratio of cyclotetrasaccharide:carbohydrate = 1:1 to 0.2:1 calculated as a solid content relative to all carbohydrates contained in the composition. [7] The composition according to [5] or [6], wherein the composition contains one or more carbohydrates selected from sugar, starch syrup, and low-calorie sweeteners. [8] The composition described in [7], wherein the low-calorie sweetener is one or more carbohydrates selected from reduced starch syrup, xylitol, maltitol, sorbitol, erythritol, reduced palatinose, and allulose. [9] The composition according to any one of [5] to [8], wherein the composition is selected from soft candy, fondant, glaze, sugar coating, coating, baked food, fried food and dried food.

[10] A method for preparing the composition according to any one of [5] to [9] above, wherein the composition is prepared by adding the crystallinity-imparting agent containing cyclotetrasaccharide.

[11] A method for imparting crystallinity to a target, comprising adding a crystallinity-imparting agent containing a cyclic tetrasaccharide to the target, wherein the cyclic tetrasaccharide has a cyclic structure composed of four α-D-glucopyranose units.

[12] The method according to

[11] , wherein the object is food. [Effects of the Invention]

[0007] According to the present invention, by adding a crystallinity-imparting agent characterized by containing cyclic tetrasaccharide, it is possible to impart crystallinity to a composition containing the crystallinity-imparting agent, and through this action, it is possible to reduce tooth stickiness or impart tooth brittleness, thereby imparting a good texture. It is also possible to solidify the composition, improve the shape retention and formability of the composition, and impart appropriate hardness and ease of molding. Furthermore, it is possible to shorten the working time and improve workability in the preparation process of the composition. DETAILED DESCRIPTION OF THE INVENTION

[0008] The present invention will now be described in further detail. <Cyclic tetrasaccharide> In the present invention, a "cyclotetrasaccharide" has a cyclic structure composed of four α-D-glucopyranose units. The cyclotetrasaccharide may be a cyclotetrasaccharide having a structure represented by cyclo{→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→} (hereinafter referred to as "cyclonigerosilnigerose" or "CNN"). The cyclotetrasaccharide may be a cyclotetrasaccharide having the following structure: [ka] The cyclotetrasaccharide may include a branched cyclotetrasaccharide having a structure represented by cyclo{→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→}. For example, the branched cyclotetrasaccharide may have a branched structure in which one or more glucose molecules are bound to the cyclotetrasaccharide via a glycosidic bond. Examples of the branched cyclotetrasaccharide include, but are not limited to, 6-O-α-galactosyl CNN, 4-O-α-glucosyl CNN, 3-O-α-isomaltosyl CNN, 4-O-α-diglucosyl CNN, 3-O-β-N-acetylglucosaminyl CNN, 3-O-β-galactosyl CNN, 6-O-β-galactosyl CNN, and 2-O-α-glucosyl CNN. The cyclotetrasaccharide may be in the form of a crystal, an amorphous substance, or a mixture thereof. The cyclotetrasaccharide preferably comprises a crystal. The crystal may be anhydrous crystal or hydrated crystal. Preferably, the crystal is hydrated crystal. The cyclotetrasaccharide may be a crystal of cyclonigerosil nigerose (CNN). The cyclotetrasaccharide may be anhydrous crystal, monohydrate crystal, or pentahydrate crystal of cyclonigerosil nigerose. Preferably, the cyclotetrasaccharide is pentahydrate crystal of cyclonigerosil nigerose.

[0009] <Carbohydrates> As used herein, "carbohydrate" refers to carbohydrates that are not dietary fiber. As used herein, carbohydrates have a structure in which one or more monosaccharides are linked together. Examples of monosaccharides include, but are not limited to, glucose, fructose, and galactose. Examples of carbohydrates in which multiple monosaccharides are linked together include, but are not limited to, disaccharides in which two monosaccharides are linked together, oligosaccharides in which three to nine monosaccharides are linked together, and polysaccharides in which ten or more monosaccharides are linked together. Examples of disaccharides include, but are not limited to, sucrose (sugar), maltose, lactose, trehalose, and cellobiose. Examples of oligosaccharides in which three to nine monosaccharides are linked together include, but are not limited to, galactooligosaccharides, lactofructose oligosaccharides, raffinose, panose, maltotriose, melezitose, gentianose, maltooligosaccharides, isomaltooligosaccharides, fructooligosaccharides, xylooligosaccharides, gentiooligosaccharides, and nigerooligosaccharides. The oligosaccharides may be cyclic oligosaccharides. Polysaccharides include those that are not dietary fiber, and include, but are not limited to, amylose, amylopectin, glucan, glycogen, and derivatives thereof. The polysaccharides may have a cyclic structure. As used herein, "carbohydrate" includes starch syrup, reduced starch syrup, sugar alcohols, and rare sugars. As used herein, "carbohydrate" does not include cyclic tetrasaccharides. As used herein, the term "low-calorie sweetener" refers to a sweetener whose energy yield per gram (Kcal / g) is less than the energy yield per gram of sugar (energy conversion coefficient 4Kcal / g (nutrition labeling standard)). As used herein, low-calorie sweeteners include, but are not limited to, sugar alcohols, high-intensity sweeteners, and rare sugars. As used herein, sugar alcohol refers to a sugar produced by reducing the carbonyl group of an aldose or ketose, including, but not limited to, erythritol, isomalt, lactitol, maltitol, mannitol, sorbitol, xylitol, reduced palatinose, and reduced starch syrup. In this specification, high-intensity sweeteners include natural high-intensity sweeteners, chemically synthesized high-intensity sweeteners, and mixtures thereof. Examples of natural high-intensity sweeteners include stevia, glycyrrhizin, and monk fruit, while examples of chemically synthesized high-intensity sweeteners include, but are not limited to, aspartame, saccharin, acesulfame K, sucralose, and neotame. As used herein, rare sugars refer to monosaccharides and derivatives thereof that are scarce in nature, and examples thereof include, but are not limited to, allulose, tagatose, and sorbose. <Solid content> In this specification, unless otherwise specified, "solid content equivalent" refers to calculating the mass excluding the moisture contained in the components. In this specification, "solid content mass" refers to the mass excluding the moisture contained in the components.

[0010] <Crystallization agent> As used herein, the term "crystallinity-imparting agent" refers to a composition containing a cyclic tetrasaccharide having a cyclic structure composed of four α-D-glucopyranose units, which is used to impart crystallinity. The crystallinity-imparting agent as used herein is a composition that imparts crystallinity to a target to which it is added, or that adjusts the crystallinity of the target. As used herein, "imparting crystallinity" or "giving crystallinity" refers to the presence of crystals in a target to which the crystallinity-imparting agent of the present invention has been added. The crystals in a target to which the crystallinity-imparting agent of the present invention has been added may be crystals of cyclotetrasaccharide, or may be crystals of a component other than cyclotetrasaccharide. The cyclotetrasaccharide crystals may be crystals that have crystallized in a target to which the crystallinity-imparting agent of the present invention has been added. The presence of crystals in a target to which the crystallinity-imparting agent of the present invention has been added may be confirmed using methods known in the art, for example, by calculating the degree of crystallinity when analyzed by X-ray crystal diffraction. The presence of crystals in a target to which the crystallinity-imparting agent of the present invention has been added may be confirmed, for example, by an increase in the degree of crystallinity of the target to which the crystallinity-imparting agent of the present invention has been added, when analyzed by X-ray crystal diffraction, compared before and after the addition of the crystallinity-imparting agent. In one embodiment, whether an object to which the crystallinity imparting agent of the present invention has been added contains crystals may be confirmed not only by the analysis by the X-ray crystal diffraction method, but also simply by preparing an object that requires crystallinity, such as soft candy, fondant, glaze, sugar coating, coating, or meringue. In one embodiment, the crystallinity-imparting agent of the present invention "imparts crystallinity" or "confers crystallinity" to a target to which it has been added means that, after the addition of the crystallinity-imparting agent of the present invention, the cyclotetrasaccharide and / or components other than the cyclotetrasaccharide crystallize, resulting in solidification of the target to which the crystallinity-imparting agent of the present invention has been added. After the addition of the crystallinity-imparting agent of the present invention, any step may be included before the crystallization of the cyclotetrasaccharide and / or components other than the cyclotetrasaccharide occurs, but crystallization may occur without any such step. Such steps include, but are not limited to, baking, frying, drying, and the like. The presence of crystals in a target may be confirmed using methods known in the art, and may be confirmed, for example, by calculating the degree of crystallinity when analyzed by X-ray crystal diffraction. The degree of crystallinity may be derived from crystals of the cyclotetrasaccharide and / or crystals of components other than the cyclotetrasaccharide. As used herein, "adjusting crystallinity" refers to increasing or decreasing the amount of crystals contained in a target to which the crystallinity-imparting agent of the present invention has been added by increasing or decreasing the amount of the agent. The crystals contained in the target to which the crystallinity-imparting agent has been added may be crystals of cyclotetrasaccharide, or may be crystals of a component other than cyclotetrasaccharide. The increase or decrease in the amount of crystals contained in a target to which the crystallinity-imparting agent of the present invention has been added may be confirmed using methods known in the art, and may be confirmed, for example, by an increase or decrease in crystallinity when analyzed by X-ray crystal diffraction. The crystallinity may be derived from crystals of cyclotetrasaccharide, or may be derived from crystals of a component other than cyclotetrasaccharide. The crystallinity may be derived from crystals of a component contained in the target before the crystallinity-imparting agent of the present invention is added. In one embodiment, the crystallization imparting agent of the present invention promotes the crystallization of components contained in the target substance even before the addition of the crystallization imparting agent. In one embodiment, the crystallization imparting agent of the present invention promotes the crystallization of components other than cyclotetrasaccharide contained in the crystallization imparting agent. As used herein, "promoting crystallization" refers to an increase in the amount of crystals derived from components other than cyclotetrasaccharide contained in the target substance after the crystallization imparting agent is added to the target substance. The increase in the amount of crystals derived from components other than cyclotetrasaccharide contained in the target substance after the crystallization imparting agent of the present invention is added to the target substance may be confirmed using methods known in the art, and may be confirmed, for example, by an increase or decrease in the degree of crystallinity when analyzed by X-ray crystal diffraction.

[0011] The crystallinity imparting agent of the present invention may be liquid or solid, but preferably, the crystallinity imparting agent of the present invention may be solid. The crystallinity imparting agent of the present invention may be dissolved or suspended in any solvent and used in any state such as a solution, suspension, or emulsion. The crystallinity imparting agent of the present invention may be heated or cooled when dissolved or suspended in any solvent. The solvent is preferably water. The crystallinity imparting agent of the present invention may be used in its solid form. When the crystallinity imparting agent of the present invention is used in its solid form, the crystallinity imparting agent may be dissolved or suspended in the target. In some embodiments, the crystallinity-imparting agent contains cyclotetrasaccharide in an amount of about 40 to 100% by weight, calculated as solid content, relative to the total weight of the crystallinity-imparting agent. The crystallinity-imparting agent may contain cyclotetrasaccharide in an amount, calculated as solid content, of about 99.9% by weight or less, about 99.5% by weight or less, about 99% by weight or less, about 98% by weight or less, or about 95% by weight or less, relative to the total weight of the crystallinity-imparting agent. The crystallinity-imparting agent may contain cyclotetrasaccharide in an amount, calculated as solid content, relative to the total weight of the crystallinity-imparting agent of about 45% by weight or more, about 50% by weight or more, about 60% by weight or more, about 70% by weight or more, about 80% by weight or more, about 90% by weight or more, about 95% by weight or more, about 98% by weight or more, about 99% by weight or more, about 99.5% by weight or more, or about 99.9% by weight or more. The crystallinity-imparting agent may contain cyclotetrasaccharide in an amount of about 40% by mass to about 90% by mass, about 40% by mass to about 95% by mass, about 45% by mass to about 98% by mass, about 45% by mass to about 99% by mass, about 45% by mass to about 99.5% by mass, or about 45% by mass to about 99.9% by mass, based on the total mass of the crystallinity-imparting agent. Here, the total mass of the crystallinity-imparting agent means the sum of the solid masses of the contained components.

[0012] The crystallinity-imparting agent of the present invention may contain one or more carbohydrates. Examples of carbohydrates contained in the crystallinity-imparting agent of the present invention include, but are not limited to, glucose, maltose, isomaltose, glucodisaccharides with other bonding modes, maltotriose, isomaltotriose, panose, glucotrisaccharides with other bonding modes, and glucooligosaccharides or glucans with a degree of polymerization of 4 or more with various bonding modes other than cyclotetrasaccharide. The crystallinity-imparting agent of the present invention may further contain any raw material or additive commonly used in the art, as long as it does not impair the objectives of the present invention, and may further contain other ingredients effective for imparting crystallinity. The optional raw materials may be raw materials for the composition described below. Examples of other ingredients and / or additives effective for imparting crystallinity include, but are not limited to, sweeteners, colorants, preservatives, thickeners, stabilizers, gelling agents, thickeners, antioxidants, color formers, fungicides (mold inhibitors), yeast food, gum bases, alkaline water, bittering agents, enzymes, glazing agents, flavorings, acidulants, softeners, seasonings, coagulants, strengthening agents, emulsifiers, pH adjusters, leavening agents, nutritional fortifiers, and physical property improvers such as tartrates, potassium sodium tartrate, and potassium hydrogen tartrate.

[0013] <Composition> As used herein, the term "composition" refers to a mixture containing the crystallinity-imparting agent of the present invention. The composition of the present invention is not particularly limited as long as the crystallinity of the components contained therein is imparted or adjusted by the crystallinity-imparting agent of the present invention. The composition of the present invention may be a composition that solidifies due to the crystallization of the components contained therein. Non-limiting effects brought about by the crystallization of the components include a good texture due to reduced stickiness or improved brittleness, good shape retention and form retention, and the impartation of appropriate hardness and ease of molding. The composition of the present invention utilizes the effect of crystallization of an ingredient. The composition of the present invention includes, but is not limited to, compositions that are themselves intended for oral ingestion, such as food compositions, solid-containing beverage compositions, and pharmaceutical compositions. The composition of the present invention may be a composition used as a raw material, ingredient, or material for a composition that utilizes the effect of crystallization of an ingredient, such as a food composition, solid-containing beverage composition, pharmaceutical, quasi-drug, cosmetic, animal feed, feed, or fertilizer. Examples of compositions or raw materials, ingredients, or materials that utilize the effect of crystallization of an ingredient include, but are not limited to, soft candy, gum, caramel, tablet, fondant, glaze, icing, sugar coating, and coating. Compositions utilizing the effect of crystallization of contained ingredients include compositions whose moisture content has been reduced by processes such as baking, frying, drying, etc., and may be, for example, baked products, fried products, or dried products, or may be raw materials, ingredients, or materials for baked products, fried products, or dried products. Examples of the baked products, fried products, or dried products, or raw materials, ingredients, or materials for baked products, fried products, or dried products, include batter liquids, batter mixes, premixes, etc. for bouchées, dacquoise, meringues, cookies, hard biscuits, soft biscuits, rice crackers, arare (rice crackers), okoshi (rice crackers), cereal bars, energy bars, tempura, etc., but are not limited to these.

[0014] The composition of the present invention may contain one or more carbohydrates. The carbohydrate may be, but is not limited to, one or more selected from sugar, starch syrup, and low-calorie sweeteners. Low-calorie sweeteners include reduced starch syrup, sugar alcohols, and rare sugars. Sugar, reduced starch syrup, or sugar alcohols are preferred. The sugar alcohol may be one or more sugar alcohols selected from xylitol, maltitol, sorbitol, erythritol, and reduced palatinose, with erythritol being preferred. The composition of the present invention contains the cyclotetrasaccharide and all the carbohydrates contained in the composition at a ratio of about 1:1 to about 0.2:1, calculated as a solid content. The composition of the present invention may contain the cyclotetrasaccharide and all the carbohydrates contained in the composition at a ratio of about 1:1, about 0.9:1, about 0.8:1, about 0.75:1, about 0.6:1, about 0.5:1, about 0.4:1, about 0.35:1, about 0.3:1, or about 0.25:1, calculated as a solid content. Here, the mass of all the carbohydrates contained in the composition is the sum of the solid content masses of all the carbohydrates contained in the composition. Here, the mass of the cyclotetrasaccharide is the solid content mass. The composition of the present invention may contain cyclotetrasaccharide:sugar in a mass ratio of about 4:6 to about 9:1. The composition of the present invention may contain cyclotetrasaccharide:sugar in a mass ratio of about 4:6, about 4.5:5.5, about 5:5, about 6:4, about 7:3, about 8:2, or about 9:1. Here, the mass of cyclotetrasaccharide is the mass of the solid content. The composition of the present invention may contain cyclotetrasaccharide:reduced starch syrup at a mass ratio of about 1:6 to about 1:1. The composition of the present invention may contain cyclotetrasaccharide:reduced starch syrup at a mass ratio of about 1:6, about 1:4, about 1:3, about 1:2, about 1:1.5, or about 1:1. Here, the masses of cyclotetrasaccharide and reduced starch syrup are solid content masses. The composition of the present invention may contain the cyclotetrasaccharide:sugar alcohol in a mass ratio of about 1:1 to about 1:0.25. The composition of the present invention may contain the cyclotetrasaccharide:sugar alcohol in a mass ratio of about 1:1, about 1:0.75, about 1:0.5, or about 1:0.25. Here, the masses of the cyclotetrasaccharide and sugar alcohol are solid masses.

[0015] The composition of the present invention may further contain optional ingredients or additives as long as they do not impair the objectives of the present invention. Examples of optional ingredients include, but are not limited to, fats and oils such as butter, vegetable oils, and hardened oils; flours such as wheat flour and cornstarch; eggs; dairy products; and flavoring materials such as cocoa, fruit, and nuts. Examples of optional additives include, but are not limited to, salt, spices, emulsifiers, coagulants such as gelatin, flavorings, colorants, leavening agents, oxidizing agents, antioxidants, thickeners, acidulants, pH adjusters, preservatives, and oil-absorbing substances such as cellulose. In some embodiments, the compositions of the present invention contain a gelling agent or solidifying agent (e.g., gelatin, pectin, starch, etc.) in an amount of 5% by weight or less, calculated as solids, relative to the total weight of the composition. In some embodiments, the compositions of the present invention may contain a gelling agent or solidifying agent (e.g., gelatin, pectin, starch, etc.) in an amount of about 4.5% by weight or less, about 4% by weight or less, about 3.5% by weight or less, about 3% by weight or less, about 2.5% by weight or less, or about 2% by weight or less, calculated as solids, relative to the total weight of the composition. Here, the total weight of the composition refers to the sum of the solid weights of each component contained in the composition.

[0016] In certain embodiments, the composition of the present invention may contain water in an amount of about 1% by mass to about 20% by mass, about 1% by mass to about 10% by mass, or about 1% by mass to about 7% by mass, relative to the total mass of the composition. The composition of the present invention may contain water in an amount of about 1% by mass or more, about 2% by mass or more, about 3% by mass or more, about 4% by mass or more, about 5% by mass or more, about 6% by mass or more, about 7% by mass or more, or about 8% by mass or more, relative to the total mass of the composition. The composition of the present invention may contain water in an amount of about 10% by mass or less, about 8% by mass or less, about 7% by mass or less, about 5% by mass or less, about 4% by mass or less, about 3% by mass or less, or about 2% by mass or less, relative to the total mass of the composition. In some embodiments, the composition of the present invention is a baked, fried, or dried product, and the moisture content of the composition is about 0.1% to about 6% by mass, based on the total mass of the composition. The moisture content of the baked, fried, or dried composition of the present invention may be about 0.5% by mass or more, about 1% by mass or more, about 2% by mass or more, about 2.5% by mass or more, about 3% by mass or more, about 3.5% by mass or more, about 4% by mass or more, about 4.5% by mass or more, about 5% by mass or more, or about 5.5% by mass or more, based on the total mass of the composition. The moisture content of the baked, fried, or dried composition of the present invention may be about 5.5% by mass or less, about 5% by mass or less, about 4.5% by mass or less, about 4% by mass or less, about 3.5% by mass or less, about 3% by mass, about 2.5% by mass, about 2% by mass, about 1.5% by mass, or about 1% by mass or less, based on the total mass of the composition.

[0017] In some embodiments, the composition of the present invention may contain about 70% by weight or less of the crystallinity-imparting agent, calculated as solids, relative to the total weight of the composition. In some embodiments, the composition of the present invention may contain about 65% by weight or less, about 60% by weight or less, about 55% by weight or less, about 50% by weight or less, about 45% by weight or less, about 40% by weight or less, about 35% by weight or less, about 30% by weight or less, about 25% by weight or less, about 20% by weight or less, about 15% by weight or less, about 10% by weight or less, or about 5% by weight or less of the crystallinity-imparting agent, calculated as solids, relative to the total weight of the composition. The composition of the present invention may contain, relative to the total mass of the composition, a crystallinity-imparting agent in an amount, calculated as solid content, of about 1% by mass or more, about 2% by mass or more, about 3% by mass or more, about 5% by mass or more, about 10% by mass or more, about 15% by mass or more, about 20% by mass or more, about 25% by mass or more, about 30% by mass or more, about 35% by mass or more, about 40% by mass or more, about 45% by mass or more, about 50% by mass or more, about 55% by mass or more, about 60% by mass or more, or about 65% by mass or more. Here, the total mass of the composition refers to the solid mass of the composition, which is expressed as the sum of the solid masses of each component contained therein. In some embodiments, the composition of the present invention contains cyclotetrasaccharide in an amount of about 15 to 70% by weight, calculated as solid content, based on the sum of the weights of all carbohydrates and cyclotetrasaccharides contained in the composition. The composition of the present invention may contain cyclotetrasaccharide in an amount of about 65% by weight or less, about 60% by weight or less, about 55% by weight or less, about 50% by weight or less, about 45% by weight or less, about 40% by weight or less, about 35% by weight or less, about 30% by weight or less, or about 25% by weight or less, calculated as solid content, based on the sum of the weights of all carbohydrates and cyclotetrasaccharides contained in the composition. The composition of the present invention may contain cyclotetrasaccharide in an amount of about 20% by weight or more, about 25% by weight or more, about 30% by weight or more, about 35% by weight or more, about 40% by weight or more, about 45% by weight or more, about 50% by weight or more, about 55% by weight or more, about 60% by weight or more, or about 65% by weight or more, calculated as solid content, based on the sum of the weights of all carbohydrates and cyclotetrasaccharides contained in the composition. The composition of the present invention may contain cyclotetrasaccharide in an amount of about 20% to about 65% by mass, about 25% to about 60% by mass, about 30% to about 60% by mass, about 35% to about 60% by mass, about 40% to about 60% by mass, or about 45% to about 60% by mass of all carbohydrates contained in the composition. Here, the sum of the masses of all carbohydrates and cyclotetrasaccharide contained in the composition refers to the sum of the solid masses of all carbohydrates contained in the composition plus the solid mass of cyclotetrasaccharide.

[0018] In one embodiment, the crystallinity-imparting agent of the present invention is added to a composition in which the total solid mass of the cyclic tetrasaccharide contained in the composition is replaced with a carbohydrate, and the standard formulation is a composition in which the total solid mass of the cyclic tetrasaccharide contained in the composition is replaced with a carbohydrate (hereinafter referred to as "standard formulation"). The carbohydrate contained in the standard formulation that is partially or completely replaced by the crystallinity-imparting agent of the present invention is not particularly limited, but is preferably sugar, starch syrup, reduced starch syrup, or sugar alcohol, and more preferably sugar. In one embodiment, the crystallinity imparting agent of the present invention may replace about 25% to about 90% by mass of the carbohydrates contained in the standard formulation, calculated as solid content. In another embodiment, the crystallinity imparting agent of the present invention may replace about 25% by mass or more, about 30% by mass or more, about 35% by mass or more, about 40% by mass or more, about 45% by mass or more, about 50% by mass or more, about 55% by mass or more, about 60% by mass or more, about 65% by mass or more, about 70% by mass or more, about 75% by mass or more, or about 80% by mass or more, calculated as solid content. In one embodiment, the crystallinity imparting agent of the present invention may replace, in solid content terms, about 90% by mass or less, about 85% by mass or less, about 80% by mass or less, about 75% by mass or less, about 70% by mass or less, about 65% by mass or less, about 60% by mass or less, about 55% by mass or less, about 50% by mass or less, about 45% by mass or less, about 40% by mass or less, about 35% by mass or less, or about 30% by mass or less of the carbohydrates contained in the standard formulation. Here, the carbohydrates contained in the standard formulation are represented by the sum of the solid masses of all carbohydrates contained in the standard formulation.

[0019] In one aspect, the crystallization agent of the present invention is added in such a way that part or all of the mass of sugar contained in 100g of food in each processed food and beverage category shown in Table 1 below (hereinafter referred to as "Baseline 2018 Sales Weighted Mean (g sugar per 100g of food)"), equivalent to 10%, 20%, or 30% by mass of the mass of sugar contained in 100g of food in each category, as shown as the 2018 Baseline Sales Weighted Mean, is replaced with cyclotetrasaccharide contained in the crystallization agent, on a solid-state basis.

[0020] [Table 1] TIFF2025167964000003.tif201170 TIFF2025167964000004.tif146170 TIFF2025167964000005.tif215170 TIFF2025167964000006.tif107170

[0021] <Characteristics of the composition> The composition of the present invention has a good texture, with low stickiness or brittleness. "Brittleness" refers to adhesion to teeth, and when there is little adhesion to teeth, it is considered to have low stickiness and a good texture. "Brittleness" refers to a texture that easily crumbles, breaks, or crumbles in the oral cavity when chewed, and in particular, in the case of baked products, those that are brittle are considered to have a good texture. In one embodiment, after the addition of the crystallinity-imparting agent of the present invention, the composition of the present invention solidifies as the cyclotetrasaccharide and / or components other than the cyclotetrasaccharide crystallize, forming a solid.

[0022] In some embodiments, the compositions of the present invention have a crystallinity of about 5% or greater when analyzed by X-ray crystallography using the following method: The compositions of the present invention may have a crystallinity of about 8% or greater, about 10% or greater, about 15% or greater, about 20% or greater, about 25% or greater, or about 30% or greater when analyzed by X-ray crystallography using the following method. In certain embodiments, the compositions of the present invention may have a crystallinity of about 30% or less, about 25% or less, about 20% or less, about 15% or less, or about 10% or less, as analyzed by X-ray crystallography using the following method. (Method for measuring crystallinity) Powder X-ray diffraction spectra are measured by the reflection method using a powder X-ray diffractometer (X'Pert Pro MPD, Spectris, Inc.). Crystallinity analysis is performed using dedicated analytical computer software (HighScore Plus, Spectris, Inc.) installed in the powder X-ray diffractometer, and the crystallinity analysis value is determined by the Hermans method.

[0023] The composition of the present invention has a moderate hardness. As used herein, moderate hardness refers to a hardness of less than about 80 N, as measured by the following method. The composition of the present invention may have a hardness of about 70 N or less, about 60 N or less, about 50 N or less, about 40 N or less, about 30 N or less, about 20 N or less, about 15 N or less, about 10 N or less, or about 5 N or less, as measured by the following method. The composition of the present invention may have a hardness of about 1 N or more, about 2 N or more, about 3 N or more, about 5 N or more, about 10 N or more, about 15 N or more, about 20 N or more, about 25 N or more, about 30 N or more, about 35 N or more, about 40 N or more, or about 45 N or more, as measured by the following method. (Hardness measurement method) 1. 5 g of the composition is molded into a sample measuring 1.5 cm wide x 2.0 cm long x 1 cm high. Using a creep meter at 2.25°C, measure the stress when a cylindrical plunger with a diameter of 8 mm is applied at a table speed of 1 mm / sec until the sample is compressed to 60% of its height (height 0.6 cm). The composition of the present invention has an appropriate hardness as described above, and therefore has the ease of molding, ie, it can be easily molded into a desired shape.

[0024] The composition of the present invention has good shape retention and shape maintenance. In this specification, "shape retention" is evaluated by the increase in the diameter (sagging) of the sample. Specifically, 7.5 g of the sample was molded into a cylindrical shape with a diameter of 2.4 cm and a height of 1.4 cm, and the diameter after molding (r0) and the diameter after storage at a temperature of 40°C and a relative humidity of 65% for X days after molding (r x ) and compare (r x It is expressed as the increase rate (%) of diameter after molding calculated by the formula (-r0) / r0. In one embodiment, the composition of the present invention has a shape retention (sagging) of about 10% to about 35% after storage at a temperature of 40°C and a relative humidity of 65% for 14 days after molding. In one embodiment, the composition of the present invention has a shape retention (sagging) of about 4% to about 60% after storage at a temperature of 40°C and a relative humidity of 65% for 14 days after molding. In one embodiment, the composition of the present invention has a shape retention (sagging) of about 0% to about 40% after storage at a temperature of 40°C and a relative humidity of 65% for 3 days after molding.

[0025] <Method for preparing the composition> The method for preparing the composition of the present invention includes a step of preparing a composition by adding the crystallinity imparting agent of the present invention. The crystallinity imparting agent of the present invention may be dissolved or suspended in any solvent and added to a target in any state, such as a solution, suspension, or emulsion. The crystallinity imparting agent of the present invention may be heated or cooled when dissolved or suspended in any solvent. The solvent is preferably water. The crystallinity imparting agent of the present invention may be added to a target in a solid state. The crystallinity imparting agent of the present invention may be added to a target in a solid state and dissolved or suspended in the target. The crystallinity imparting agent of the present invention dissolved in the target may recrystallize in the target. The process for preparing the composition of the present invention may include a heating step, which may be carried out after adding the crystallinity imparting agent of the present invention in order to reduce the water content of the composition. In one embodiment, the method for preparing the composition of the present invention includes a step of adding a crystallinity-imparting agent containing cyclotetrasaccharide and then reducing the moisture content of a mixture containing the crystallinity-imparting agent. The step of reducing the moisture content may be a step of boiling down the mixture. The step of reducing the moisture content may be a step of baking, frying, or drying the mixture. The step of boiling down the mixture may be performed by heating to a liquid temperature of about 130°C. The step of baking the mixture may be performed using an oven heated to an internal temperature of 150°C to 210°C. The step of frying the mixture may be performed at an oil temperature of 100°C to 200°C. In one embodiment, the method for preparing the composition of the present invention may include a step of adding a crystallinity-imparting agent containing cyclotetrasaccharide and then reducing the moisture content of the mixture without heating the mixture containing the crystallinity-imparting agent. In one embodiment, the method for preparing the composition of the present invention may include an aging step for promoting crystallization of the components in the composition after a step of heating a mixture containing a crystallinity-imparting agent to reduce the water content. The aging step may be performed at any temperature, but may be aged overnight at 40°C, for example. Seeds may be added to promote crystallization during the aging step. A kneading step may be included before the aging step, after the aging step, or both before and after the aging step. According to the method for preparing the composition of the present invention, the addition of the crystallization imparting agent promotes crystallization of the cyclotetrasaccharide and / or the components contained in the composition before the addition of the crystallization imparting agent, making it easier for crystals to precipitate, thereby shortening the time required for solidification and ultimately shortening the overall working time.Furthermore, the addition of the crystallization imparting agent of the present invention shortens the time required for crystals to precipitate and the dough to become non-sticky during the maturing step for promoting crystallization of the components in the composition, thereby shortening the working time.

[0026] <Method for imparting crystallinity> The method for imparting crystallinity of the present invention includes a step of adding a crystallinity imparting agent containing a cyclotetrasaccharide to an object. After the addition of the crystallinity imparting agent of the present invention, the object contains the composition of the present invention. In one aspect, the method of imparting crystallinity of the present invention involves adding a saccharide to a composition in which the entire amount of cyclotetrasaccharide contained in the composition of the present invention is replaced with a saccharide other than cyclotetrasaccharide, which is defined as a standard formulation (hereinafter referred to as "standard formulation"), in such a manner that the saccharide (excluding cyclotetrasaccharide) contained in the standard formulation is partially or entirely replaced. In one embodiment, the method of imparting crystallinity of the present invention involves replacing part or all of the sugar content (g) of sugar contained per 100g of food for each processed food and beverage category shown in Table 1 (hereinafter referred to as the "2018 Baseline Sales Weighted Mean (g sugar per 100g of food)"), calculated as the 2018 Baseline Sales Weighted Mean, with cyclotetrasaccharide, calculated as the solid content.

[0027] In the method of imparting crystallinity of the present invention, the amount of cyclotetrasaccharide added to the subject may be the same as the mass of the solid content of cyclotetrasaccharide contained in the composition of the present invention. In the method of imparting crystallinity of the present invention, the amount of cyclotetrasaccharide added to the subject may be such that the ratio of the solid mass of cyclotetrasaccharide to the solid mass of all the carbohydrates contained in the composition of the present invention is the same. In the method of imparting crystallinity of the present invention, the crystallinity imparting agent containing cyclotetrasaccharide may be added to any object, but is preferably a food, cosmetic, quasi-drug, or industrial product.

[0028] The present invention will be specifically explained below with reference to examples, but the scope of the present invention is not limited to these examples. [Example]

[0029] Example 1-1: Preparation of a crystalline composition (by formulating a soft candy using sugar and starch syrup) The samples were prepared by adding cyclonigerosylnigerose (CNN) as a cyclic tetrasaccharide to a soft candy formulation containing sugar and starch syrup at varying ratios (see Table 2 for the formulation).

[0030] [Table 2]

[0031] <Preparation method> (1) Water and CNN (pentahydrate crystals, moisture content 11.6%, manufactured by Hayashibara Co., Ltd.) were added to a stainless steel container and dissolved by heating using an induction heater. Then, starch syrup (Maltrap 45, solid content 75%, manufactured by Hayashibara Co., Ltd.) and sugar (granulated sugar, manufactured by Ensuiko Sugar Refining Co., Ltd.) were added and boiled down to the specified weight of 152 g using an induction heater. For the formulation of control 1, which contained only starch syrup and sugar, the starch syrup and sugar were added to a stainless steel container and heated using an induction heater while mixing with a spatula until the specified weight of 152 g was reached. (2) To the above (1), 10 g of an emulsifier (DK Creamer E-80, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) was added to 90 g of water, and the mixture was heated to dissolve to prepare a 10% by mass emulsifier solution. Then, hydrogenated oil (Numelanin 35, manufactured by Fuji Oil Co., Ltd.) heated to 70°C was added, and the mixture was heated with an induction heater while being mixed with a spatula, and boiled down to the specified weight of 170 g. (3) To (2) above, 33 g of powdered gelatin (APH200, manufactured by Nitta Gelatin Co., Ltd.) was added to 67 g of water, and then a 33% by mass gelatin solution that had been heated and dissolved and kept at 70°C was added and mixed using a spatula. (4) While the stainless steel container was placed in a water bath at 75°C, the mixture was kneaded for an additional 20 minutes using a Three-One Motor (HEIDON, 600G, manufactured by Shinto Scientific Co., Ltd.). (5) Seeds (CNN in the example, sugar powder in control 1) were added to (4) above and kneaded for 5 minutes. The test sample dough was then removed, wrapped in food wrap film, and left to mature overnight at 40°C. (6) After aging, the mixture was kneaded (conched) with a rolling pin, and 5 g of the test sample was filled into a 12-hole metal deposit machine hard candy mold with holes measuring 1.5 cm wide x 2.0 cm long x 1 cm deep. The mold was then pressed with a rolling pin to form test sample pieces.

[0032] Example 1-2: Evaluation method of a composition imparted with crystallinity The test samples (pieces) prepared in Example 1-1 were measured and evaluated for hardness, shape retention, texture (toothiness), moisture content, and crystallinity by the following methods. <Hardness> Five test specimens were prepared as measurement samples from each of the test specimens obtained in the molding step of the above 2. Preparation method (6). The stress applied to the test specimen was measured using a creep meter at 25°C until the specimen was compressed to 60% of its height, and this was used as an index of hardness. The average value of five samples was recorded. [Measurement conditions] Creep meter (Model number: RE2-33005C, manufactured by Yamaden Co., Ltd.) Plunger (Model: No. 6 Φ8 mm cylindrical) Table speed: 1mm / sec [Hardness evaluation criteria] ◎ (best): 15N or more and less than 60N ○ (Good): Less than 15N and 60N to 80N △ (slightly poor): 80N or more and less than 100N × (defective): 100N or more <Shape retention> Shape retention was evaluated based on the increase in diameter (sagging) of each test sample. (1) 7.5 g of the test sample after conching in the above 2. Preparation method (6) was packed into an ointment container with a diameter of 2.4 cm and a depth of 1.4 cm, formed into a cylinder, and immediately removed from the container. (2) Three measurement samples obtained in (1) above were prepared and each was stored for 14 days in a thermo-hygrostat set at a temperature of 40°C and a relative humidity of 65%. (3) The diameters of the test samples were measured immediately after molding and after 14 days of storage, and the rate of increase was calculated. The rate of increase was calculated by dividing the increase in diameter after 14 days of storage by the diameter immediately after molding and multiplying this value by 100, and the average value of the three samples was used as an index of shape retention. [Evaluation criteria for shape retention] ◎ (Best): 0% to less than 50% Good: 50% or more but less than 75% △ (slightly poor): 75% or more but less than 100% × (defective): 100% or more <Texture (with teeth)> Each test sample piece obtained in the molding step of 2. Preparation method (6) above was evaluated for tooth contact when bitten by five trained expert panelists. The evaluation was as follows: ◎ (Best): Four or more out of five panelists felt that the product did not stick to their teeth when chewed and had a good bite (better than commercially available products). ◯ (Good): Two or three out of five panelists felt that the product did not stick to the teeth when chewed and had a good bite (similar to commercially available products). × (bad): Less than one out of five panelists felt that the chew did not stick to the teeth when chewed and felt that the chew felt good (inferior to commercially available products). <Overall evaluation of hardness, shape retention, and texture (toothiness)> The hardness, shape retention, and texture (toothiness) were comprehensively evaluated according to the following evaluation criteria. [Overall evaluation criteria] ◎ (Best): Hardness, shape retention, and texture are all rated as 〇 (good) or above 〇 (Good): Two or more of the hardness, shape retention, and texture are rated 〇 (good) or higher, and there are no × (bad) ratings. △ (slightly poor): Two or more of the hardness, shape retention, and texture were rated △ (slightly poor), or one of them was rated × (poor). × (bad): Hardness, shape retention, and texture are rated × (bad). <Moisture percentage> 1 g of the test sample after conching in the above 2. Preparation method (6) was thinly spread on a sample dish with a spatula, and the moisture content was measured using a moisture meter (MOC63u, manufactured by Shimadzu Corporation). <Crystallinity> Approximately 5 mg of the test sample after conching in the above 2. Preparation method (6) was thinly spread on a non-reflective silicon plate as a measurement sample, and the powder X-ray diffraction spectrum was measured by the reflection method using a powder X-ray diffractometer (X'Pert Pro MPD, manufactured by Spectris Co., Ltd.). The crystallinity analysis was carried out using dedicated analytical computer software (HighScore Plus, manufactured by Spectris Co., Ltd.) installed in the powder X-ray diffractometer, and the analytical value of the crystallinity was determined by the Hermans method.

[0033] <Result> Table 3 shows the evaluation results for test samples 1-1 to 1-6 and control sample 1, which were soft candies containing sugar and starch syrup, in which part of the sugar was replaced with CNN. Regarding hardness, test samples 1-1 to 1-5 had hardnesses of 25.1 to 59.5 N, compared to 4.2 N for control sample 1, and all of them had extremely good hardness. Regarding shape retention (after 14 days), test samples 1-2 to 1-5, in which CNN was added to replace part of the sugar, all showed very good shape retention with only 14 to 32% runnyness, which was equivalent to the control sample, whereas test sample 1-1 had 109% runnyness and poor shape retention. Regarding texture (stickiness), test samples 1-2 to 1-5, in which CNN was added to replace part of the sugar, exhibited a good texture that was less likely to stick to the teeth, which was equal to or better than that of control sample 1, and test samples 1-4 and 1-5 in particular were found to have an excellent texture that was significantly less likely to stick to the teeth. The crystallinity of the control sample was 19.0, while that of the test samples in which CNN was added to replace part of the sugar was slightly lower, but a tendency for it to increase depending on the amount of CNN was observed. Test Sample 1-6 could not be molded and therefore could not be evaluated. Furthermore, no significant difference was observed in the moisture content of any of the samples. These results indicate that when CNN is blended in a soft candy composition containing sugar and starch syrup in an amount ranging from 28.6 to 42.9% by mass, calculated as solid matter, based on the total sugar and CNN content, the hardness, shape retention, and texture (teethiness) are extremely desirable.

[0034] The results in Table 3 demonstrate that CNN, a cyclic tetrasaccharide, is a significantly superior crystallinity-imparting agent in soft candy compositions containing sugar and starch syrup.

[0035] [Table 3]

[0036] Example 2: Preparation of a crystalline composition (by formulating a soft candy using reduced starch syrup) and its evaluation <Preparation method> Test samples 2-1 to 2-5 were prepared by adding CNN as a cyclic tetrasaccharide to a soft candy formulation containing reduced starch syrup (MU-50, solid content 70%, manufactured by Ueno Food Tech Co., Ltd.) at a ratio of 16.5% to 37.6% by mass relative to the sample mass. The preparation method was the same as in Example 1-1. The specific formulations are shown in Table 4.

[0037] [Table 4]

[0038] <Result> Table 5 shows the evaluation results of test samples 2-1 to 2-5, which were soft candies containing reduced starch syrup, in which part of the reduced starch syrup was replaced with CNN. Regarding hardness, test samples 2-1 to 2-5, in which part of the reduced starch syrup was replaced with CNN, showed hardness values ​​of 2.8 to 7.0 N. Although these values ​​were generally slightly lower than the results of Example 1, in which sugar and starch syrup were combined, all had appropriate hardness. Regarding shape retention (after 14 days), test samples 2-2 to 2-5 showed good shape retention with little sagging at 4.2 to 67%, and test samples 2-4 and 2-5 in particular had remarkably excellent shape retention. On the other hand, test sample 2-1 showed sagging at 96%, which was somewhat inferior. Regarding texture (toothiness), test samples 2-3 to 2-5 exhibited a good texture that did not stick to the teeth, and it was revealed that test sample 2-4 in particular had an excellent texture that did not stick to the teeth at all. The crystallinity index ranged from 8.9 to 12.8, and tended to increase depending on the CNN dose. Furthermore, no significant difference was observed in the moisture content of any of the samples. These results indicate that in soft candy compositions containing reduced starch syrup, when the CNN content relative to the total sugar and CNN content is in the range of 28.7 to 43.1% by mass, calculated as solid content, the hardness, shape retention, and texture (teethiness) are extremely desirable.

[0039] The results in Table 5 demonstrate that CNN, a cyclic tetrasaccharide, is a significantly superior crystallinity-imparting agent in soft candy compositions containing reduced starch syrup.

[0040] [Table 5]

[0041] Example 3: Preparation of a crystalline composition (by formulating a soft candy using reduced starch syrup and a low-calorie sweetener) and its evaluation <Preparation method> In a soft candy formulation using a sugar alcohol or rare sugar as a low-calorie sweetener, a test sample was prepared in which CNN was used as the cyclic tetrasaccharide instead of the low-calorie sweetener. Furthermore, the hardness, shape retention, texture (teethiness), and crystallinity were evaluated using the same methods as in Example 1-2. The formulation and preparation method for the soft candy using the low-calorie sweetener were the same as in Example 1-1, except that potassium hydrogen tartrate was added in addition to the emulsifier and fat in step (2). The raw materials used, such as the low-calorie sweetener, are shown in Table 6, and their formulations in Table 7. The evaluation methods were the same as in Example 1-2.

[0042] [Table 6]

[0043] [Table 7]

[0044] In soft candy compositions containing reduced starch syrup and a low-calorie sweetener, the low-calorie sweetener was replaced with CNN. The evaluation results for test sample 3 and control samples 3-1 to 3-6 are shown in Table 8. Regarding hardness, test sample 3, which was formulated by replacing the low-calorie sweetener with CNN, showed a hardness of 9.9N, which was similar to the hardness of control samples 3-1, 3-2, and 3-4, which used xylitol, maltitol, and erythritol as low-calorie sweeteners. Regarding shape retention (after 14 days), Test Sample 3 showed 74%, and had appropriate shape retention with little runnyness, similar to Control Samples 3-1 and 3-4, which used xylitol and erythritol as low-calorie sweeteners. On the other hand, Test Sample 3-2, which used maltitol as a low-calorie sweetener, showed runnyness of 100% or more, and had poor shape retention. Regarding texture (toothiness), Test Sample 3 exhibited a good texture that did not stick to the teeth, similar to Control Samples 3-1 and 3-4, which used xylitol and erythritol as low-calorie sweeteners. On the other hand, Test Sample 3-2, which used maltitol as a low-calorie sweetener, tended to stick to the teeth and had a poor texture. Regarding the degree of crystallinity, Test Sample 3 showed 11.4, while Control Samples 3-1 and 3-4, which used xylitol and erythritol as low-calorie sweeteners, showed 20.7 and 17.2, respectively. Furthermore, test sample 3-6, which used allulose as a low-calorie sweetener, was not evaluated because it was judged to be unsuitable as a soft candy composition due to its intense coloration.

[0045] The results in Table 8 show that in a soft candy composition containing reduced starch syrup and a low-calorie sweetener, when CNN is used in place of the low-calorie sweetener, the hardness, shape retention, and texture (teethiness) are equal to or better than those of xylitol and erythritol, which are low-calorie sweeteners, and that its effects are comparable to those of maltitol, sorbitol, reduced isomaltulose, and allulose. Furthermore, the sugar alcohols xylitol and erythritol have the characteristic of giving a cool sensation when put in the mouth, which limits the flavoring options available. However, CNN does not produce this cool sensation, and it has been shown to have significantly superior effects compared to xylitol and erythritol.

[0046] [Table 8]

[0047] Example 4: Preparation of a crystalline composition (a formulation in which cyclic tetrasaccharide and erythritol are added in combination to a soft candy using reduced starch syrup) and its evaluation Sugarless soft candies were prepared by combining reduced starch syrup with CNN as a low-calorie sweetener and cyclic tetrasaccharide at various blend ratios, and their physical properties were evaluated. The specific blend compositions are shown in Table 9.

[0048] [Table 9]

[0049] The soft candies prepared as described above were evaluated for hardness, shape retention (after 3 days), texture (teeth), and crystallinity (after 6 days) using the same methods as in Example 1-2, and the results are shown in Table 10.

[0050] [Table 10]

[0051] Table 10 shows the evaluation results for test samples 4-1 to 4-4, which were soft candy compositions containing reduced starch syrup and in which the erythritol and CNN ratio was varied from 1:1 to 1:0.25. Regarding hardness, test samples 4-1 to 4-4 exhibited hardness of 18.4 to 47.8 N, and had extremely good hardness at any blend ratio. Regarding shape retention (after 3 days), test samples 4-1 to 4-4 showed a range of 0 to 38%, and had little sagging and extremely good shape retention at any blending ratio. Regarding texture (toothiness), test samples 4-1 to 4-4 exhibited a good texture that did not stick to the teeth at any blend ratio. In particular, test samples 4-1 and 4-2, which had erythritol to CNN blend ratios of 1:1 and 1:0.5, respectively, had a significantly superior texture that did not stick to the teeth at all. The crystallinity of test samples 4-1 to 4-4 was 17.8, 17.8, 14.6, and 13.7, and it was observed that the crystallinity tended to increase as the amount of erythritol increased.

[0052] The results in Table 10 show that in sugarless soft candy compositions containing reduced starch syrup, erythritol, and CNN, when the CNN is blended with erythritol at a blending ratio of 1:1 to 1:0.25, the hardness, shape retention, and texture (teethiness) are extremely excellent. This demonstrates that CNN, a cyclic tetrasaccharide, is a significantly excellent crystallinity-imparting agent in sugarless soft candy compositions. Furthermore, without wishing to be bound by any particular theory, the crystallinity of the test sample increased and reached a plateau as the amount of erythritol added increased, suggesting that CNN not only crystallized in the test sample but also crystallized erythritol. Therefore, it is believed that the addition of CNN increased the amount of crystals, regardless of the origin of the crystals, resulting in a sugarless soft candy with significantly improved hardness, shape retention, and texture (teeth).

[0053] Example 5: Effect of the inclusion of cyclotetrasaccharide on the aging process (step (5)) (shortening of solidification time) In the soft candy recipe of Example 1, half the mass of the sugar contained in Control 1 was replaced with cyclonigerosylnigerose (CNN) (solids equivalent) as a cyclic tetrasaccharide or a low-calorie sweetener to form test or control samples. These were prepared according to the preparation method of Example 1-1 and evaluated according to the evaluation method of Example 1-2. In addition, during sample preparation, the workability (solidification time) and workability (conching state) were also evaluated in relation to the state of the aging process in step (5). The formulations are shown in Table 11, and the results are shown in Tables 12 and 13. The low-calorie sweeteners used in Controls 5-1 to 5-6 were the same as the raw materials listed as sweeteners in Table 6 of Example 3. (Observation of the aging process) In step (5), seeds (CNN for the test sample, sugar powder for the control) were added and kneaded for 5 minutes. The sample dough was then removed, wrapped in food wrap, and left to mature overnight at 40°C. The dough was then placed in a constant temperature bath at 40°C while still wrapped in the food wrap, and the state of solidification was checked. Solidification was assessed using the strength of adhesion between the wrapped sample dough and the food wrap at the start of aging, 4 hours, 19 hours, and 24 hours. (Workability (evaluation of solidification time)) The workability (solidification time) was evaluated using the time it took to form the dough during conching as an index of adhesion to food wrap, and was shown according to the following criteria. ◎ (Best): The food wrap film is sufficiently solidified so that it can be easily peeled off the sample fabric. 〇 (Good): The food wrap film has solidified to the extent that it partially adheres to the sample fabric. × (Poor): The food wrap film adheres to the sample fabric but does not peel off, and solidification is insufficient. (Workability (conching condition)) The workability (conching state) was evaluated using the hardness of the sample during conching as an index, and was shown according to the following evaluation criteria. ◎ (Best): Appropriate hardness and good workability 〇 (Good): A little hard, but did not affect workability × (bad): The product was too soft to be conched and had poor workability.

[0054] [Table 11]

[0055] <Result> In soft candy compositions containing sugar and starch syrup, part of the sugar was replaced with a low-calorie sweetener or CNN in order to reduce the sugar content. The evaluation results for Test Sample 5, Control 1, and 5-1 to 5-6 are shown in Tables 12 and 13. Regarding workability (conching state), Test Sample 5 containing CNN had an appropriate dough hardness and good workability, similar to Control 1, which contained no low-calorie sweetener, and Controls 5-4 and 5-5, which contained erythritol and isomaltulose reduction as low-calorie sweeteners. On the other hand, Controls 5-1 to 5-3 and 5-6, which contained xylitol, maltitol, sorbitol, and allulose as low-calorie sweeteners, had loose dough and poor workability. Regarding workability (solidification time), Test Sample 5, which contained CNN, solidified from the start of aging and had extremely good workability compared to Control 1, which contained no low-calorie sweetener. On the other hand, Controls 5-4 and 5-5, which contained erythritol and isomaltulose reduction as low-calorie sweeteners, solidified 19 hours and 4 hours after the start of aging, respectively, and had poor workability. Furthermore, Controls 5-1 to 5-3 and 5-6, which contained xylitol, maltitol, sorbitol, and allulose as low-calorie sweeteners, had loose dough and no solidification was observed. Regarding hardness, test sample 5 containing CNN showed an appropriate hardness of 62.9 N, which was similar to control 1, which did not contain any low-calorie sweeteners, and controls 5-4 and 5-5, which contained erythritol and isomaltulose reduction as low-calorie sweeteners. Regarding shape retention (after 14 days), Test Sample 5, which contained CNN, was slightly inferior to Control 1, which did not contain a low-calorie sweetener, but showed appropriate shape retention with little sagging at 50%. Controls 5-4 and 5-5, which contained erythritol and isomaltulose reduction as low-calorie sweeteners, both showed sagging of 93% or more and had poor shape retention. Regarding texture (toothiness), test sample 5 containing CNN exhibited an extremely excellent texture, being less likely to stick to the teeth, compared to control sample 1, which did not contain any low-calorie sweeteners, and controls 5-4 and 5-5, which contained erythritol and isomaltulose reduction as low-calorie sweeteners. Regarding the degree of crystallinity, Test Sample 5 showed a value of 18.6, while Control 1, Control 5-4 and Control 5-5 showed values ​​of 29.2, 18.1 and 13.2, respectively.

[0056] The results in Table 12 clearly show that in a soft candy composition containing sugar and starch syrup and with reduced sugar content, when CNN was used in place of half the amount of sugar, workability, such as conching state and solidification time, was extremely excellent. This effect was more pronounced than that of sugar, erythritol, and reduced isomaltulose. Furthermore, this effect was comparable to that of xylitol and erythritol as low-calorie sweeteners, and significantly superior to that of maltitol, sorbitol, reduced isomaltulose, and allulose. The results in Table 13 clearly show that when CNN was used in place of half the amount of sugar in a soft candy composition containing sugar and starch syrup and with reduced sugar content, the hardness, shape retention, and texture (chewiness) were significantly improved. This effect was more pronounced than that of sugar, erythritol, and reduced isomaltulose. Furthermore, this effect was comparable to that of xylitol and erythritol as low-calorie sweeteners, and significantly superior to that of maltitol, sorbitol, reduced isomaltulose, and allulose. These results demonstrate that CNN, a cyclic tetrasaccharide, is a remarkably excellent crystallinity-imparting agent.

[0057] [Table 12] [Table 13]

[0058] Example 6: Preparation and evaluation of crystalline baked product compositions Cookies were prepared by substituting cyclotetrasaccharide for sugar or part of the sugar as described below, and were evaluated and compared in terms of appearance, texture (brittleness), workability, and hardness. The composition and evaluation results are shown in Table 14. <Preparation method> The butter was beaten to form a pomade, and then mixed with sugar and CNN as a cyclic tetrasaccharide (the control was sugar only). To this, whole eggs were added in several batches and further mixed. Sieved soft flour was then added and kneaded to prepare the dough. The prepared dough was wrapped in plastic wrap and left to rest in the refrigerator for 2 hours, after which it was rolled out to a thickness of 3 mm using a rolling pin and cut into circular shapes using a ring mold. The cut-out dough was placed on a baking tray and baked in an oven with both ends set at 170°C for 15 minutes to prepare the test sample. <Evaluation method> (1) Appearance (shape and browning) was visually inspected by texture evaluation panelists and judged according to the following criteria. ◎ (Best): Excellent appearance equivalent to commercially available products × (Poor): Appearance was inferior to that of commercially available products (2) Texture (brittleness) was evaluated according to the method of Example 1-2 by five trained expert panelists who evaluated the brittleness of each test sample obtained in the molding process of 2. Preparation method (6) when chewed, using the following criteria. ◎ (Best): Four or more out of five panelists felt that the product did not stick to the teeth when chewed and had good tooth brittleness. (Better than commercially available products) ◯ (Good): Two or three out of five panelists felt that the product did not stick to the teeth when chewed and had good tooth brittleness (same as commercially available products). × (Poor): Less than one out of five panelists felt that the product did not stick to the teeth when chewed and had good tooth brittleness (inferior to commercially available products). (3) Workability was evaluated based on the degree of stretching of the dough during the rolling process according to the following criteria. ◎: The sample fabric is not sticky, has a moderate hardness, is easy to stretch, and is easy to work with. 〇: The sample fabric is slightly hard, but it is easy to stretch and does not hinder workability. ×: The sample material is hard and difficult to work with. (4) Hardness was measured using the same method as in Example 1-2.

[0059] [Table 14]

[0060] The CNN-containing baked products of test samples 6-1 and 6-2 both had good tooth brittleness. As shown in Table 14, Test Samples 6-1 and 6-2, which were formulated by replacing part of the sugar with CNN as a sweetener, exhibited excellent appearance properties comparable to those of Control Sample 6, which contained only sugar. Furthermore, the dough of Test Sample 6-1, which was formulated by replacing part of the sugar with CNN, had workability comparable to that of Control Sample 6, which contained sugar. Test Sample 6-2, which contained a higher amount of CNN, also had a slightly harder dough, but still had good workability. On the other hand, Test Samples 6-1 and 6-2, which contained CNN, were significantly more brittle than Control Sample 6, which contained only sugar, and had an extremely good texture. Furthermore, when the hardness of each sample was measured, Control Sample 6, which contained only sugar, had a hardness of 35.6 N, while Test Sample 6-1 had a hardness of 30.2 N and Test Sample 6-2 had a hardness of 16.0 N, demonstrating that the hardness was suppressed depending on the amount of CNN. This indicates that the CNN content relative to the total sugar and CNN content is preferably in the range of more than 0 and 50% by mass in terms of solid content.

[0061] The results in Table 14 show that when CNN is blended in a range of more than 0 to 50 mass% of the total carbohydrate and CNN content in terms of solid matter in a baked product composition containing CNN, the appearance, workability, and texture (brittleness) are excellent.

Claims

1. A crystallinity-imparting agent comprising a cyclotetrasaccharide, wherein the cyclotetrasaccharide has a cyclic structure composed of four α-D-glucopyranose units.

2. The crystallinity-imparting agent according to claim 1, wherein the cyclotetrasaccharide is a cyclotetrasaccharide having a structure represented by cyclo{→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→}.

3. The crystallinity imparting agent according to claim 1, wherein the cyclic tetrasaccharide is cyclonigerosyl nigerose pentahydrate crystal.

4. The crystallinity imparting agent according to claim 1 , wherein the cyclic tetrasaccharide is contained in an amount of 40 to 100% by mass, calculated as a solid content, based on the total mass of the crystallinity imparting agent.

5. A composition comprising the crystallinity imparting agent according to claim 1.

6. 6. The composition according to claim 5, wherein the cyclotetrasaccharide is contained in a mass ratio of cyclotetrasaccharide:carbohydrate = 1:1 to 0.2:1 calculated as a solid content relative to all carbohydrates contained in the composition.

7. The composition of claim 5 , wherein the composition comprises one or more carbohydrates selected from sugar, starch syrup, and low-calorie sweeteners.

8. The composition according to claim 7, wherein the low-calorie sweetener is one or more carbohydrates selected from reduced starch syrup, xylitol, maltitol, sorbitol, erythritol, reduced palatinose, and allulose.

9. 6. The composition of claim 5, wherein the composition is selected from soft candies, fondants, glazes, sugar coatings, coatings, baked goods, fried goods, and dry goods.

10. 6. The method for preparing the composition according to claim 5, wherein the composition is prepared by adding the crystallinity-imparting agent comprising a cyclotetrasaccharide.

11. A method for imparting crystallinity to a target, the method comprising adding a crystallinity-imparting agent containing a cyclic tetrasaccharide to the target, wherein the cyclic tetrasaccharide has a cyclic structure composed of four α-D-glucopyranose units.

12. The method of claim 11 , wherein the object is a food product.

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