JP6382058B2 - Method for producing sugar condensate - Google Patents

Description

  The present invention relates to a method for producing a sugar condensate. Specifically, a low molecular fraction in a sugar condensate obtained by a sugar condensation reaction or an enzymatic degradation product of the sugar condensate is separated, and the low molecular fraction is obtained. The present invention relates to a method for producing a sugar condensate as it is or mixed with a raw material for a sugar condensation reaction and subjected to a sugar condensation reaction again.

  It is known that sugar condensates can be produced by heat-treating saccharides in the absence of a catalyst or in the presence of various catalysts to cause a condensation reaction, and various methods for producing sugar condensates have been reported (Patent Document 1). ~ 6). The sugar condensate has a function as an indigestible saccharide and a water-soluble dietary fiber, and is widely used as a functional food material. However, it has been confirmed that the sugar condensate produces a low-molecular-weight carbohydrate having a bitter taste such as gentiobiose and a different taste such as sweetness in the reaction process. In addition, it is known that non-fermentable disaccharides contained in the low molecular fraction of the sugar condensation reaction product are likely to induce diarrhea. Due to the above problems, the dosage and use as food are limited.

  Furthermore, in the dietary fiber measurement method such as enzyme-HPLC method, since a component having a polymerization degree of 3 or more is measured as dietary fiber, the content of dietary fiber is reduced due to the inclusion of a saccharide of disaccharide or less, and a functional food material. It is known that the value of will also decline.

  In other words, to reduce the bitterness, sweetness, and off-flavor of sugar condensates, broaden their use as foods and improve their value, and increase the dietary fiber content of sugar condensates to improve their value as functional food materials Therefore, it is necessary to remove or reduce the low molecular fraction containing monosaccharides and disaccharides.

  As a method for solving the above problems, for example, a method of fractionating and removing a low molecular fraction by chromatography or membrane treatment is known (Patent Documents 7 and 8). However, the low-molecular fractions removed by these production methods are all processed as waste or low added-value carbohydrates, and the dietary fiber obtained from the raw material carbohydrates has a very poor yield, production efficiency, There were major problems in terms of manufacturing cost and environmental impact.

JP 2003-231694 A JP 2005-510581 A JP-T-2006-502103 Special table 2009-540068 gazette Special table 2009-524439 Japanese Patent No. 4966429 Japanese Patent Laid-Open No. 04-183372 Japanese Patent Application Laid-Open No. 06-032802

  An object of the present invention is to provide a method for producing a sugar condensate having a low bitterness, a high water-soluble dietary fiber content, and a high utility value for food and drink with a high yield.

  The present inventors separated a low molecular fraction from a sugar condensate composition produced by heat condensation of a saccharide, and left the sugar condensation reaction product in the low molecular fraction as it was or the sugar It was found that a sugar condensate can be produced with a high yield by mixing with a saccharide, which is a raw material for the heat-condensation reaction, and again performing a sugar condensation reaction. The present invention is based on this finding.

That is, the present invention is as follows.
(1) A method for producing a sugar condensate or a reduced product thereof,
(A) A saccharide condensate composition obtained by subjecting one or more saccharides or derivatives thereof to a saccharide condensation reaction or an enzyme-decomposable composition thereof, and a saccharide having a polymerization degree of 9 or less in terms of solid content as 50 % Fraction (low molecular fraction) and other fractions,
(B) The following steps (B-1) and (B-2):
(B-1) A sugar condensate composition in which a low molecular fraction is subjected to a saccharide condensation reaction alone, or a low molecular fraction is subjected to a saccharide condensation reaction together with one or more saccharides or derivatives thereof. Alternatively, the step of obtaining the enzyme-decomposable composition, and the sugar condensate composition or the enzyme-decomposed composition obtained in step (B-2) (B-2) into a low-molecular fraction and other fractions. The dividing step is performed once or twice or more (however, when the step (B-2) is the final step, the step (B-2) may be omitted)
The manufacturing method characterized by the above-mentioned.
(2) The production method according to (1), wherein the sugar condensation reaction is performed in the presence of one or more catalysts selected from inorganic acids, organic acids, mineral substances, and activated carbon.
(3) The production method according to (1) or (2), wherein the content of water-soluble dietary fiber in the sugar condensate is 70% or more.
(4) The production method according to any one of (1) to (3), wherein the sugar condensation reaction is performed under a temperature condition of 100 ° C to 300 ° C.
(5) In step (B), step (B-1) (however, the low molecular fraction is subjected to a sugar condensation reaction together with one or more saccharides or derivatives thereof) and step (B-2) Is repeated two or more times, The manufacturing method in any one of said (1)-(4) characterized by the above-mentioned.
(6) The production method according to any one of (1) to (5), further comprising a step of reducing the produced sugar condensate.
(7) A sugar condensate produced by the production method according to any one of (1) to (6) or a reduced product thereof.
(8) A food or drink comprising the sugar condensate or the reduced product thereof according to (7).
(9) A sugar condensate or a reduced product thereof is produced by the production method according to any one of (1) to (6), and then the sugar condensate or the reduced product thereof is added to a food or drink or a raw material thereof. The manufacturing method of the food-drinks characterized by the above-mentioned.

  According to the production method of the present invention, a sugar condensate having a high utility value for food and drink can be produced with a high yield, which is advantageous in terms of production efficiency and production cost. Conventionally, most of the low molecular fraction separated and removed from the sugar condensation reaction product has been treated as industrial waste. However, according to the production method of the present invention, such a low molecular fraction is subjected to sugar condensation. Since it can be recycled as a raw material for the reaction, the present invention is an invention that contributes to resource saving and environmental load reduction, and is also advantageous in terms of the environment.

Detailed description of the invention

  In the production method of the present invention, first, in step (A), the saccharide condensation composition obtained by the saccharide condensation reaction and the enzymatic degradation composition thereof were divided into a low molecular fraction and a high molecular fraction, and then obtained. The recycling process (B) comprised from a process (B-1) and a process (B-2) is implemented using a low molecular fraction. Hereinafter, the sugar condensation reaction in the step (A) and the step (B-1) and the separation of the low molecular fraction from the sugar condensation composition in the step (A) and the step (B-2) will be described.

Sugar Condensation Reaction In the production method of the present invention, a saccharide or a derivative thereof is subjected to a sugar condensation reaction to produce a sugar condensate.
Here, the “sugar condensation reaction” refers to a reaction in which sugars are condensed and polymerized to obtain a sugar condensate. Typically, water molecules are released from two sugars and the sugars are polymerized. Such a reaction.

In the present invention, a sugar condensation reaction can be carried out using one or more carbohydrates as a substrate.
There are no particular limitations on the carbohydrates that can be subjected to the sugar condensation reaction, and any of monosaccharides, oligosaccharides, and polysaccharides, and their reduced products can be used. When it is intended to be used for food, carbohydrates that can be used as food and drink can be used. In addition, considering the remarkable coloring of ketose (fructose, etc.) during heating (sugar condensation reaction), the sugar to be subjected to the sugar condensation reaction is composed of aldoses such as glucose, galactose, mannose, ribose, arabinose, xylose, etc. Is preferred.

  In the present invention, a carbohydrate derivative can also be used as a substrate for a sugar condensation reaction. Examples of carbohydrate derivatives include oxides such as sugar acids, reduced products such as sugar alcohols, and modified products such as amino sugars, etherified sugars, halogenated sugars, and phosphorylated sugars. When it is intended to be used for food and drink, derivatives that can be used as food and drink can be used. Examples include sorbitol, galactitol, mannitol, xylitol, erythritol, maltitol, lactitol, glucosamine, glucose-6-phosphate, and the like, but there is no particular limitation as long as it is a carbohydrate derivative that can be used as a food or drink.

  In the present invention, “monosaccharide” refers to a sugar that is a constituent unit of an oligosaccharide or polysaccharide, and examples thereof include glucose, galactose, mannose, ribose, arabinose, xylose, lyxose, erythrose, fructose, psicose, etc. There is no particular limitation as long as it is a monosaccharide that can be used as a product. In consideration of coloring during the sugar condensation reaction, aldoses such as glucose, galactose, mannose, ribose, arabinose and xylose are preferred.

  In the present invention, the “oligosaccharide” refers to a saccharide having 2 to 10 monosaccharides bound thereto, for example, maltose, cellobiose, trehalose, gentiobiose, isomaltose, nigerose, sophorose, cordobiose, sucrose, turanose, lactose, Examples include xylobiose, maltooligosaccharide, isomaltooligosaccharide, nigerooligosaccharide, xylooligosaccharide, gentiooligosaccharide, fructooligosaccharide, galactooligosaccharide, mannooligosaccharide, cyclodextrin, etc. .

  In the present invention, “polysaccharide” refers to a saccharide having 11 or more monosaccharides bound thereto, such as starch, dextrin, pullulan, dextran, arabinoxylan, pectin, inulin, galactan, mannan, indigestible dextrin, polydextrose, However, there is no particular limitation as long as it is a carbohydrate that can be used as a food or drink.

  In the production method of the present invention, saccharides in general can serve as a substrate for a saccharide condensation reaction. Examples of saccharides that can be used as a condensation substrate include glucose, monosaccharides other than glucose and glucose, reduced products of glucose, oligosaccharides, and Examples thereof include combinations with one or more selected from the group consisting of dextrins, and in addition to these, one or two or more monosaccharides other than glucose, oligosaccharides, and polysaccharides are combined to perform the sugar condensation reaction. It may be a substrate. In addition, a starch degradation product can be used as a substrate for a sugar condensation reaction.

  In the production method of the present invention, the substrate for the sugar condensation reaction may be a crystallized saccharide and / or a non-crystalline saccharide powder, or a syrup-like saccharide. The syrup-like saccharide that can be used as a substrate for the saccharide condensation reaction in the production method of the present invention is not particularly limited as long as it is an aqueous solution of saccharide, but preferably has a low water content in the condensation reaction.

  In the production method of the present invention, the sugar condensation reaction may be performed in the absence of a catalyst or in the presence of a catalyst, but it is preferably performed in the presence of a catalyst from the viewpoint of the reaction efficiency. The catalyst for the sugar condensation reaction is not particularly limited, and examples thereof include inorganic acids, organic acids, mineral substances, activated carbon, and the like. Materials listed in the additive list are preferred. Further, various catalysts may be used in combination.

  Examples of inorganic acids that can be used as the catalyst include hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid and the like. Examples of the organic acid that can be used as the catalyst include citric acid, fumaric acid, tartaric acid, succinic acid, and acetic acid. Examples of the mineral substance that can be used as the catalyst include diatomaceous earth, activated clay, acidic clay, bentonite, kaolinite, talc and the like. Examples of the activated carbon that can be used as the catalyst include steam charcoal, zinc chloride charcoal, sulfonated activated carbon, oxidized activated carbon, and the like, and the shape thereof is not particularly limited, such as granular, powdery, fibrous, plate-like, and honeycomb-like.

  In the production method of the present invention, when activated carbon is used as a catalyst for the sugar condensation reaction, the sugar condensation reaction can be carried out at 100 ° C. or higher, preferably at a temperature higher than the melting point of the saccharide serving as a substrate. From the viewpoint of efficiency, it can be carried out in a temperature range of 100 ° C. to 300 ° C., preferably 100 ° C. to 280 ° C., more preferably 170 ° C. to 280 ° C. The reaction time can be adjusted according to the degree of progress of the condensation reaction. When the ratio of the indigestible fraction in the reaction product is adjusted to 75% or more, for example, the reaction temperature is 180 ° C. for 5 to 180 minutes, The reaction temperature can be 190 ° C for 1 to 180 minutes, and the reaction temperature 200 ° C for 1 to 180 minutes. The structure of the reaction equipment varies depending on the atmospheric pressure method or the reduced pressure method, but there is no particular limitation as long as it is a machine that satisfies the heating condition of 100 ° C. to 300 ° C. Examples thereof include a shelf hot air dryer, a thin film evaporator, a flash evaporator, a vacuum dryer, a hot air dryer, a steam jacket screw conveyor, a drum dryer, an extruder, a worm shaft reactor, and a kneader. Also, the reaction equipment can be continuous.

  In the production method of the present invention, the sugar condensation reaction can be carried out under normal pressure conditions or under reduced pressure conditions. When the sugar condensation reaction is carried out under reduced pressure, it is advantageous because the coloring degree of the reaction product is lowered.

  The “sugar condensate” produced by the present invention refers to a sugar polymer obtained by subjecting a sugar to a heat treatment in the absence of a catalyst or in the presence of various catalysts to cause a condensation reaction, and has a degree of polymerization of two or more. If so, the structure and constituent sugars are not particularly limited. Since the sugar condensate obtained by the condensation reaction has a random linkage mode of sugar residues, it is not easily hydrolyzed by digestive enzymes and has a function as dietary fiber. The “sugar condensate” produced according to the present invention includes “roasted dextrin” obtained by hydrolyzing and condensing starch in the presence of hydrochloric acid, and “hard digestion” obtained by enzymatic treatment of the roasted dextrin. And “polydextrose” obtained by condensing glucose and sorbitol in the presence of citric acid.

  In the production method of the present invention, the sugar condensate composition obtained by the sugar condensation reaction may be subjected to the procedure for separating the low molecular fraction as it is, but from the viewpoint of increasing the dietary fiber content, An enzyme degradation product composition may be obtained by treatment with a degrading enzyme, and a low molecular fraction may be separated from the enzyme degradation product composition.

  The saccharide-degrading enzyme to be used is not particularly limited. For example, α-amylase, β-amylase, glucoamylase, isoamylase, pullulanase, amyloglucosidase, α-glucosidase, cyclodextrin glucanotransferase, β-glucosidase, β -Galactosidase, β-mannosidase, β-fructosidase, cellobiase, gentiobiase and the like can be mentioned, and there is no particular limitation as long as it is an enzyme that can be used as a food. From the viewpoint of increasing the dietary fiber content, α-amylase and amyloglucosidase are preferably used, and from the viewpoint of improving taste quality by degrading bitter substances such as gentiobiose, β-glucosidase is preferably used. More preferably, the commercial item of these enzymes is mentioned. The substrate concentration, reaction temperature, reaction time, etc. during the enzyme treatment may be appropriately adjusted according to the characteristics of the enzyme used. Since the digestible site in the sugar condensate can be removed by the enzyme treatment, the dietary fiber content of the sugar condensate can be increased. Moreover, the low molecular fraction produced by the above enzymatic degradation can be removed by the separation procedure of the low molecular fraction described below.

  The sugar condensate obtained by the production method of the present invention may be converted into a reduced product such as a sugar alcohol. In the present invention, the sugar alcohol is a sugar alcohol in which the aldehyde group of the glucosyl group at the reducing end of the sugar is reduced to form a hydroxyl group. The timing for converting the sugar condensate into the sugar alcohol may be after the sugar condensation reaction (before separation of the low molecular fraction) or after separation of the low molecular fraction.

  Methods for obtaining sugar alcohols are well known to those skilled in the art, and examples of usable reduction methods include a method using a hydride reducing agent, a method using a metal in a protic solvent, an electrolytic reduction method, a catalytic hydrogenation reaction method, etc. Is mentioned. In the present invention, when preparing a small amount of sugar alcohol, the method using a hydride reducing agent is convenient and convenient without requiring a special device, while on the other hand, when carried out industrially on a large scale, A method using a catalytic hydrogenation reaction is preferable because it is economical and has few by-products.

  The catalytic hydrogenation reaction is a reaction in which hydrogen is added to a double bond portion of an unsaturated organic compound in the presence of a catalyst, and is generally also referred to as a hydrogenation reaction. The sugar alcohol production method according to the present invention will be described in detail. The sugar condensate used in the present invention is dissolved in water, an appropriate amount of Raney nickel catalyst is added thereto, hydrogen gas is added, and reduction is performed under high temperature conditions. Next, decolorization / deionization treatment is performed to obtain a sugar condensate-reducing sugar composition.

  In the production method of the present invention, the obtained sugar condensate may be concentrated by decolorizing with activated carbon as necessary, or by removing an ionic component with an appropriate ion exchange resin. In the storage and subsequent use, it is preferable to concentrate the decolorized and ion-removed product until the water activity is such that the propagation of microorganisms does not become a problem. Or it can also be dried and made into a powder so that it may be easy to utilize depending on a use. For drying, a method such as freeze drying, spray drying or drum drying can be used. The dried product is desirably pulverized as necessary.

Separation of low molecular fraction In the production method of the present invention, a low molecular fraction is separated from a sugar condensate composition or an enzymatic degradation composition thereof, and the separation method may use means well known to those skilled in the art. Methods for purifying carbohydrates well known to those skilled in the art such as membrane separation, gel filtration chromatography, carbon-celite column chromatography, strong acid cation exchange column chromatography, ethanol precipitation, and solvent precipitation can be used.

  The low molecular fraction obtained by the production method of the present invention comprises 50% or more of a saccharide having a polymerization degree of 9 or less contained in the sugar condensate composition in terms of solid content. Examples of the saccharide having a polymerization degree of 9 or less include monosaccharides, oligosaccharides including disaccharides to nine sugars, and anhydrous sugars, and further include sugar-hydrolyzed decomposition products. The above-mentioned anhydrous sugar is a saccharide obtained by intramolecular dehydration of hexose or furanose, and 1,6-anhydro-β-D-glucopyranose (anhydropyranose), 1,6-anhydro-β-D-glucofuranose. (Anhydrofuranose) is exemplified. The low-molecular-weight fraction includes an unreacted raw material sugar of the sugar condensation reaction, an oligosaccharide / anhydrosugar (sugar condensation reaction product) generated by the condensation reaction, a decomposition product of the raw sugar, and the enzyme decomposition treatment. Monosaccharides and oligosaccharides produced by The above low molecular fraction contains carbohydrates having a degree of polymerization of 2 or less (that is, monosaccharides, disaccharides, anhydrous sugars, and sugar thermal decomposition products) in consideration of the method for calculating the amount of dietary fiber by the enzyme-HPLC method. In this case, the low molecular fraction obtained from the sugar condensate composition or its enzymatic degradation composition should be adjusted so that a saccharide having a polymerization degree of 2 or less is contained in an amount of 30% or more in terms of solid content. More preferably, 50% or more in terms of solid content, still more preferably 70% or more in terms of solid content, particularly preferably 80% or more in terms of solid content, most preferably 90% or more in terms of solid content Can be adjusted to be included.

  The sugar condensate obtained by the production method of the present invention is characterized by having a high water-soluble dietary fiber content because it undergoes a step of separating and removing a low molecular fraction containing a large amount of non-dietary fiber fractions and condensing again. The water-soluble dietary fiber content can be measured by a high performance liquid chromatographic method (enzyme-HPLC method) shown in the examples described later. Although there is no restriction | limiting in particular in the dietary fiber content of the sugar condensate obtained by the manufacturing method of this invention, Preferably it is 70% or more, More preferably, it is 80% or more, Most preferably, it is 90% or more.

  Hereinafter, each process of the manufacturing method of this invention is demonstrated more concretely.

Step (A)
In the production method of the present invention, first, the step (A) is performed to divide the sugar condensate composition or the enzymatic degradation composition thereof into a low molecular fraction and other fractions, that is, a high molecular fraction. The obtained low molecular weight fraction is used as a raw material for the sugar condensation reaction in the step (B-1) of the step (B). On the other hand, the remaining fraction after the low-molecular-weight fraction is separated from the sugar condensate composition or the enzymatic degradation composition thereof is a high-molecular fraction rich in dietary fiber, and the step (B) ( In addition to the polymer fraction obtained in B-2), the final product is a sugar condensate or a reduced product thereof.

  The sugar condensation reaction in the step (A) carried out to obtain the sugar condensate composition may be the same as or different from the sugar condensation reaction carried out in the step (B-1). Examples of the difference in the sugar condensation reaction between the step (A) and the step (B-1) include, for example, a case where the raw materials in both steps are different and a case where the reaction catalysts in both steps are different. In step (A), a sugar condensate composition obtained by a sugar condensation reaction may be obtained and fractionated into a low molecular fraction and a high molecular fraction. (For example, pine fiber, fiber sol 2 (both manufactured by Matsutani Chemical Co., Ltd.)) and polydextrose (for example, lites, lites II (both manufactured by Danisco Japan)) and other commercially available sugar condensate compositions are obtained. And may be fractionated into a low molecular fraction and a high molecular fraction.

Step (B-1)
The process (B) of the production method of the present invention is a recycling process, and includes a process (B-1) and a process (B-2). In the step (B-1), the low molecular fraction is again subjected to a sugar condensation reaction to obtain a sugar condensate. Specifically, the low molecular weight fraction is subjected to a sugar condensation reaction alone, or together with one or more saccharides or derivatives thereof, which are raw materials for the sugar condensation reaction, from the viewpoint of the efficiency of the sugar condensation reaction. To sugar condensation reaction. In the latter case, the low molecular fraction can be mixed with one or more saccharides or derivatives thereof to cause a saccharide condensation reaction. The process flow for subjecting the low molecular fraction obtained in step (A) to the sugar condensation reaction again is as shown in FIG. In addition, when the raw sugar is a polysaccharide, the sugar condensation reaction may be performed after subjecting the raw sugar to a hydrolysis reaction. The process flow in the case of performing the sugar condensation reaction by subjecting the raw sugar to the hydrolysis reaction is as shown in FIG.

  When the low molecular fraction is subjected to a sugar condensation reaction in the step (B-1), the low molecular fraction may be subjected to a sugar condensation reaction as it is, or may be added to a raw material sugar as it is and subjected to a sugar condensation reaction. However, from the viewpoint of subsequent sugar condensation reaction efficiency and suppression of coloration, the low molecular fraction is preferably used after the solid content concentration of 15 to 99%, more preferably after the solid content concentration of 50 to 99%. preferable. There is no particular limitation on the method for adjusting the solid content concentration of the low molecular weight fraction, and the solid content concentration may be increased by concentration treatment. Syrup, sugar suspension, starch syrup, powdered rice cake, crystalline sugar, powdered sugar You may raise solid content concentration by mixing with.

  The sugar condensation reaction in the step (B-1) may be the same as or different from the sugar condensation reaction in the step (A). A process flow in which the low molecular fraction obtained in the step (A) is subjected to a sugar condensation reaction different from that in the step (A) is as shown in FIG. In the production method of the present invention, the step (B-1) and the step (B-2) may be repeated twice or more as described later. In that case, the sugar condensation in each step (B-1) is performed. The reactions may be the same or different. Examples of different sugar condensation reactions include the case where the raw materials in both steps are different and the case where the reaction catalysts in both steps are different.

Step (B-2)
In the step (B-2) constituting the step (B) of the production method of the present invention, the low molecular fraction is separated from the sugar condensate composition obtained in the step (B-1) and the enzymatic decomposition composition thereof. . When the step (B-1) and the step (B-2) are repeated twice or more, the low molecular fraction obtained in the step (B-2) is used as a raw material for the sugar condensation reaction in the step (B-1). Used. On the other hand, the remaining fraction after the low molecular fraction is separated from the sugar condensate composition or its enzymatic degradation composition is a high molecular fraction rich in dietary fiber, and the sugar condensate that is the final product Or a reduced product thereof. Therefore, the polymer fraction obtained in the step (B-2) can be combined with the sugar condensate obtained in the step (A) to obtain a sugar condensate as a final product or a reduced product thereof. .

  The separation procedure of the low molecular fraction in the step (B-2) may be the same as or different from the procedure in the step (A). Further, in the production method of the present invention, the step (B-1) and the step (B-2) may be repeated twice or more as described later. In that case, the low molecule of each step (B-2) The separation procedure of the fractions may be the same or different.

  In the production method of the present invention, when the step (B-2) corresponds to the final step, the step (B-2) may be omitted. That is, when the step (B) is performed once, the step (B-2) may be completed by performing only the step (B-1) without performing the step (B-2). As will be described later, when the step (B) is repeated twice or more, the step (B-2) is not performed at the final stage of the repetition of the step (B-1) and the step (B-2). Only the step (B-1) may be performed to end the step (B). In these cases, the reaction product obtained in step (B-1) is combined with the sugar condensate obtained in step (A) or step (B-2), etc., and the sugar condensate that is the final product. Or it can be set as the reduced product.

Repeating Step (B-1) and Step (B-2) In the production method of the present invention, the step (B-1) and the step (B-2) can be repeated twice or more. By repeating step (B-1) and step (B-2) two or more times, a sugar condensate can be produced with a high yield. The number of repetitions is not particularly limited, but when achieving a high yield rate and aiming for low cost and low environmental load, it is preferable to perform step (B) five times or more after performing step (A), More preferably, it is 10 times or more.

  Specifically, the step (B-1) and the step (B-2) can be repeated two or more times as follows. First, a low molecular fraction is separated from a sugar condensation composition obtained by a sugar condensation reaction, and a polymer fraction is obtained (step (A)). Next, the low molecular fraction is added to the raw sugar, and a sugar condensation reaction (step (B-1) in the first cycle) is performed, and the low molecular fraction is separated from the obtained sugar condensation composition. A polymer fraction is obtained (first cycle step (B-2)). Next, the low molecular fraction obtained in the process (B-2) in the first cycle was added to the raw material carbohydrate, and the sugar condensation reaction (the process (B-1) in the second cycle) was performed. A low molecular fraction is separated from the sugar condensation composition and a high molecular fraction is obtained (step (B-2) in the second cycle). The third and subsequent cycles can be performed in the same manner as the second cycle. As described above, in the final stage of the repetition of the step (B-1) and the step (B-2), the step (B-1) is not performed, the step (B-1) is performed, and the step (B) is performed. May be terminated. In the two or more repeated steps of the step (B-1) and the step (B-2) described above, the low molecular fraction obtained in the step (A) and the low molecular fraction obtained in the step (B-2) are obtained. A part or all of the molecular fraction may be subjected to a sugar condensation reaction alone in the step (B-1).

Use of sugar condensate The sugar condensate obtained by the production method of the present invention and / or its reduced product is a water-soluble dietary fiber, and is added to various foods and drinks as a functional material, excipient, and bulking agent. be able to. Therefore, according to this invention, the food / beverage products which contain the sugar condensate obtained by the manufacturing method of this invention, or its reduced product are provided. According to the present invention, a sugar condensate or a reduced product thereof is produced by the production method of the present invention, and then the sugar condensate or a reduced product thereof is added to a food or drink or a raw material thereof. A method for producing a food or drink is provided.

  Specific examples of foods and drinks to which the sugar condensate obtained by the production method of the present invention can be added include various seasonings (soy sauce, miso, moromi, salted salmon, hashio, flicker, mayonnaise, Dressing, vinegar, three cups of vinegar, powdered sushi vinegar, Chinese soup, tsutsuyu, noodle soup, dashi soup, sauce, ketchup, grilled meat sauce, seasoning solution for pickles, curry roux, stew soup, soup stock, dashi soup, umami Seasoning, compound seasoning, mirin, mirin-style seasoning, syrup, powdered rice cake, table sugar), various Japanese confectionery (senbei, arabe, okoshi, fertilizer, rice cake, manju, dorayaki, seaweed, rice cake, Water sheep, brocade, castella, jasper), various pastries (bread, biscuits, crackers, cookies, pie, donuts, steamed cake, pudding, jelly, butter cream, custard Cream, waffle, sponge cake, chocolate, chewing gum, caramel, nougat, candy, syrup), various ice confectionery (ice cream, sorbet, gelato, shaved ice), various pasty foods (flower paste, peanut paste, margarine, Fruit paste), processed fruits / vegetables (jam, marmalade, syrup pickles, sugar cane, pickles), processed meat products (ham, sausage, salami, fish ham, fish sausage, seaweed, chikuwa, salty, squid, dried fish), Various dairy products (cheese, yogurt, butter), various prepared foods, various bottled / canned products, various mixed powders (hot cake mix, batter mix), various carbohydrates (bread, noodles, cooked rice, rice cake), various beverages ( Fruit juice-containing beverages, fruit juice juice, vegetables Juice, cider, ginger ale, isotonic beverage, amino acid beverage, coffee beverage, green tea, tea, oolong tea, barley tea, lactic acid beverage, cocoa, beer, sparkling liquor, third beer, non-alcoholic beverage, beer flavored beverage, liqueur, Chuhai , Refined sake, fruit liquor, distilled liquor, energy drink, health drink, powdered drink). Furthermore, it can also be used as a health food (for example, a food for specified health use, a nutritional functional food, a nutritional supplement), a functional food, a food for the sick, etc. by utilizing its function as a water-soluble dietary fiber. Examples of the form include tablets, liquids, capsules (soft capsules, hard capsules), powders, granules, sticks, jelly, and the like.

  The present invention will be specifically described based on the following examples, but the present invention is not limited to these examples. In the present specification, when the ratio per “solid content” or the content ratio of “solid content” is mentioned, it means the ratio determined based on the mass of the solid component.

  Various measurement methods and analysis methods shown in the examples were performed as follows.

Measurement of dietary fiber content Measured by the high performance liquid chromatographic method (enzyme-HPLC method) described in April 26, 1999, on Shin-Shin No. 13 (Analysis method for nutritional components, etc. in the nutrition labeling standards) . Specifically, it was performed as follows.

First, 1 g of a sample is accurately measured, 50 ml of 0.08 mol / l phosphate buffer is added, and it is confirmed that the pH is 6.0 ± 0.5. To this, 0.1 ml of a thermostable α-amylase (Sigma: EC 3.2.1.1 Bacillus licheniformis derived) solution is added, placed in boiling water, and allowed to stand for 30 minutes with stirring every 5 minutes. After cooling, sodium hydroxide solution (1.1 → 100) is added to adjust the pH to 7.5 ± 0.1. Add 0.1 ml of protease (from Sigma: EC 3.4.21.62 Bacillus licheniformis ) solution and react for 30 minutes while shaking in a water bath at 60 ± 2 ° C. After cooling, 0.325 mol / l hydrochloric acid is added to adjust the pH to 4.3 ± 0.3. Add 0.1 ml of amyloglucosidase (Sigma: EC 3.2.13 Aspergillus niger ) solution, and allow to react for 30 minutes while shaking in a 60 ± 2 ° C. water bath. Immediately after the above enzyme treatment is completed, the mixture is heated in a boiling water bath for 10 minutes, then cooled, and 5 ml of glycerin (10 → 100) is added as an internal standard substance to make 100 ml with water to obtain an enzyme treatment solution. 50 ml of the enzyme-treated solution was passed through a column (glass tube 20 mm × 300 mm) packed with 50 ml of ion exchange resin (OH type: H type = 1: 1) at a flow rate of 50 ml / hour, and further the total amount of the effluent through water. To 200 ml. The solution is concentrated on a rotary evaporator and the total volume is made up to 20 ml with water. Filter through a membrane filter with a pore size of 0.45 μm to make a test solution.

  Next, liquid chromatography is performed on 20 μl of the test solution, and the peak area values of glycerin and dietary fiber fraction of the test solution are measured.

The analysis conditions for liquid chromatography were as follows.
Detector: differential refractometer column: ULTRON PS-80N (φ8.0 × 300 mm, Shimadzu GL), connecting column temperature: 80 ° C.
Mobile phase: Pure water flow rate: 0.5 ml / min

The dietary fiber component content was calculated from the following formula.
Dietary fiber component content (%) = [peak area of dietary fiber component / peak area of glycerin] × f1 × [weight of internal standard glycerin (mg) / weight of weighing material (mg)] × 100
(In the above formula, f1 is the sensitivity ratio (0.82) of the peak areas of glycerin and glucose.)

Example 1: Sugar condensation reaction and normal fractionation (1) Sugar condensation reaction Add 100% syrup (DE87, manufactured by Nippon Shokuhin Kako Co., Ltd.) with 2% (per solid content) activated carbon (Futamura Chemical Co.) Thereafter, the mixture was put into a heating reactor (manufactured by ADVANTEC) and heated at 180 ° C. for 10 minutes to obtain a sugar condensate composition sample. The sample after the reaction was cooled to room temperature, and this sample was made into a 20% aqueous solution per solid content, and then the activated carbon was completely removed by filtration to obtain a soluble carbohydrate. The obtained carbohydrate fraction was decolorized and filtered with activated carbon and decolorized with an ion exchange resin, and then concentrated with an evaporator.

(2) Separation of low molecular fraction Thereafter, a low molecular fraction of disaccharides or less was removed using a resin fractionator (manufactured by Nippon Nensui).
The water-soluble dietary fiber obtained was 76.5 g and the dietary fiber content was 92%. Therefore, the yield from 100 g of the raw material was 76.5%.

  Table 1 shows the results of analyzing the candy candy used as a raw material for the sugar condensation reaction and the low molecular fraction fraction-removed in (2) under the following HPLC conditions. (In the table, G3 represents a saccharide having a polymerization degree of 3, G2 represents a saccharide having a polymerization degree of 2, and G1 represents a saccharide having a polymerization degree of 1.)

<HPLC conditions>
Detector: differential refractometer column: Ultron PS-80N · L (φ8.0 mm × 500 mm)
Column temperature: 80 ° C
Mobile phase: Pure water flow rate: 0.5 ml / min

  As is clear from Table 1, the composition of the low molecular fraction removed in (2) and the raw starch syrup are greatly different, and the low molecular fraction contains a large number of sugar condensation reaction products. Was confirmed. That is, only the maltooligosaccharide and maltose peaks were detected in the fraction of trisaccharide or higher (G3 or higher) and disaccharide (G2) fraction in the raw syrup, whereas G3 or higher in the low molecular fraction was detected. The fraction and G2 fraction include various oligosaccharides composed of 1,2 bonds, 1,3 bonds, 1,4 bonds, and 1,6 bonds including α and β anomers (eg, isomaltose, cellobiose, gentiobiose). ) Was predicted (detail composition is unknown), and peaks of other components mainly consisting of anhydrous sugar (anhydrofuranose and anhydrous pyranose) were also detected in the low molecular fraction. .

Example 2: Production of sugar condensate by recondensation of low molecular fraction (1) Sugar condensation reaction The same operation as in Example 1 (1) was performed.

(2) Separation of low molecular fraction The same operation as in Example 1 (2) was performed.

(3) Recondensation reaction of low molecular fraction Further, the low molecular fraction (solid content: 13.5 g) separated in (2) above was concentrated to a solid content concentration of 70%, and 2% (per solid content) of activated carbon ( Futamura Chemical Co., Ltd.) was added and mixed, followed by heat treatment, activated carbon filtration, decolorization filtration, and decolorization with an ion exchange resin, and then concentrated with an evaporator. Thereafter, using a resin fractionator, a low-molecular fraction having a disaccharide or less (a fraction containing 84.6% of a sugar having a disaccharide or less in terms of solid content) was removed. The total amount of water-soluble dietary fiber combining the sugar condensate obtained in (2) above and the sugar condensate obtained in (3) was 78.2 g, and the dietary fiber content was 92%. Therefore, the yield from 100 g of the raw material was 78.2%.

Example 3: Production of a sugar condensate by reusing a low molecular fraction as a raw material (1) Sugar condensation reaction The same operation as in Example 1 (1) was performed.

(2) Separation of low molecular fraction The same operation as in Example 1 (2) was performed.

(3) Reuse of low molecular fraction as raw material Furthermore, the low molecular fraction (solid content: 13.5 g) separated in (2) above is concentrated to a solid content of 70%, and 86.5 g of candy candy per solid content. (DE87, manufactured by Nippon Shokuhin Kako Co., Ltd.) and reused as a raw material for sugar condensation so as to have a solid concentration of 70%. After adding and mixing 2% (per solid content) activated carbon (manufactured by Futamura Chemical Co., Ltd.), heat treatment, activated carbon filtration, decolorization filtration, and decolorization with an ion exchange resin were similarly performed, and the mixture was concentrated with an evaporator. Thereafter, using a resin fractionator, a low molecular fraction having a disaccharide or less (a fraction containing 94.3% of a sugar having a disaccharide or less in terms of solid content) was removed. The total amount of water-soluble dietary fiber combining the sugar condensate obtained in (2) above and the sugar condensate obtained in (3) was 153 g, and the dietary fiber content was 92%. Therefore, the yield from 186.5 g of the raw material was 82.0%.

Example 4: Production of sugar condensate by 10 cycles of reuse of low molecular fractions as raw material (1) Sugar condensation reaction The same operation as in Example 1 (1) was performed.

(2) Separation of low molecular fraction The same operation as in Example 1 (2) was performed.

(3) 10 cycles of reuse of low molecular fractions as raw material After blending the low molecular fraction obtained in (2) above with candy, which is the raw material for the sugar condensation reaction, and subjecting it to a sugar condensation reaction, as in Example 3. The operation of separating the low-molecular fraction again by the method (2) was defined as one cycle, and the cycle was repeated 10 cycles. The total amount of water-soluble dietary fiber obtained by combining the sugar condensate obtained in (2) and the sugar condensate obtained in (3) was 841 g, and the dietary fiber content was 92%. Therefore, the yield from 965 g of the raw material was 87.2%.

  The yield (%) of the water-soluble dietary fiber obtained in Examples 1 to 4 is summarized in Table 2. It was found that a sugar condensate rich in dietary fiber can be produced with a very high yield by mixing the low molecular fraction fractionated from the sugar condensate composition with the raw sugar and using it again in the sugar condensation reaction (example) 3 and 4). In addition, it was possible to reduce the environmental load by not discarding the low molecular fraction. As is clear from Example 2, when the low molecular fraction fractionated from the sugar condensate composition is used again for the sugar condensation reaction, the yield is improved compared to the case where the condensation reaction is not performed again (Example 1). To do. In addition, when the low molecular fraction was mixed with the raw sugar and subjected to the sugar condensation reaction again (Examples 3 and 4), the low molecular fraction fractionated from the sugar condensate composition was directly used for the sugar condensation reaction again. The yield was further improved compared to the case (Example 2). Although not limited by the following theory, when the low molecular fraction fractionated from the sugar condensate composition is used again in the sugar condensation reaction as it is, the yield rate is slightly lower. This is probably because anhydrosugar inhibited the sugar condensation reaction.

Example 5: Sugar condensation reaction, enzyme treatment and normal fractionation (1) Sugar condensation reaction 100 g of water candy (DE87, manufactured by Nippon Shokuhin Kako Co., Ltd.) per solid content 2% (per solid content) of activated carbon (Futamura Chemical Co., Ltd.) After adding and mixing, the sample was put into a heating reactor (ADVANTEC) and heated at 180 ° C. for 10 minutes to obtain a sample. The sample after the reaction was cooled to room temperature, and a 20% aqueous solution per solid content was prepared so that the final concentration was 1 mM acetate buffer (pH 5.0). To this sample, α-amylase (Chrytase L-1, Amano Enzyme) and amyloglucosidase (Dextrozyme DXJ, Novozyme) were added at an enzyme concentration of 1.0 U / g, respectively. For 24 hours. Thereafter, the activated carbon was completely removed by filtration to obtain a soluble carbohydrate (enzymatic degradation composition). The resulting enzyme-decomposed composition was subjected to decolorization filtration using activated carbon, decolorization using an ion exchange resin, and evaporator concentration.

(2) Separation of low molecular fraction Thereafter, a low molecular fraction of disaccharide or less was separated using a resin fractionator. The obtained water-soluble dietary fiber was 72.0 g, and the dietary fiber content was 99% or more. Therefore, the yield from 100 g of the raw material was 72.0%.

  Table 3 shows the results obtained by analyzing the starch candy used as a raw material for the sugar condensation reaction and the low molecular fraction fraction-removed in (2) under the same conditions as the HPLC conditions in Table 1.

  As is clear from Table 3, the composition of the low molecular fraction removed in (2) and the raw starch syrup are greatly different, and the low molecular fraction contains a large number of sugar condensation reaction products. Was confirmed. That is, only the maltooligosaccharide and maltose peaks were detected in the fraction of trisaccharide or higher (G3 or higher) and disaccharide (G2) fraction in the raw syrup, whereas G3 or higher in the low molecular fraction was detected. In the same manner as in Example 1, the G2 fraction contains various oligosaccharides composed of 1,2 bonds, 1,3 bonds, 1,4 bonds and 1,6 bonds, including α and β anomers (for example, Many peaks expected to be isomaltose, cellobiose, and gentiobiose) were detected, and peaks of other components mainly consisting of anhydrous sugar (anhydrofuranose and anhydrous pyranose) were also detected in the low molecular fraction.

Example 6: Production of sugar condensate by recondensation reaction of enzyme-treated low molecular fraction (1) Sugar condensation reaction The same operation as in Example 5 (1) was performed.

(2) Separation of low-molecular fraction The same operation as in Example 5 (2) was performed.

(3) Recondensation reaction of low-molecular fraction Further, the low-molecular fraction (solid content: 18 g) separated in (2) above is concentrated to a solid content concentration of 70%, and 2% activated carbon (manufactured by Phutamura Chemical Co., Ltd.) is added. After mixing, the mixture was subjected to heat treatment, enzyme treatment, activated carbon filtration, decolorization filtration, and decolorization with an ion exchange resin in the same manner as (1) above, and then concentrated with an evaporator. Thereafter, using a resin fractionator, a low molecular fraction having a disaccharide or less (a fraction containing 94.9% of a sugar having a disaccharide or less in terms of solid content) was removed. The total amount of water-soluble dietary fiber obtained by combining the sugar condensate obtained in (2) and the sugar condensate obtained in (3) was 75.4 g, and the dietary fiber content was 99% or more. Therefore, the yield from 100 g of the raw material was 75.4%.

Example 7: Production of a sugar condensate by reusing an enzyme-treated low molecular fraction as a raw material (1) Sugar condensation reaction The same operation as in Example 5 (1) was performed.

(2) Separation of low-molecular fraction The same operation as in Example 5 (2) was performed.

(3) Reuse of low molecular fractions as raw materials Further, the low molecular fraction (solid content 18 g) separated in (2) above was concentrated to a solid content concentration of 70%, and 82 g of syrup (DE87, Japan) per solid content. And re-used as a raw material for sugar condensation so as to have a solid concentration of 70%. After adding and mixing 2% (per solid content) activated carbon (Futamura Chemical Co., Ltd.), heat treatment, enzyme treatment, activated carbon filtration, decolorization filtration, and decolorization with ion exchange resin are performed in the same manner as in (1) above. Concentrated. Thereafter, using a resin fractionator, a low molecular fraction having a disaccharide or less (a fraction containing 94.9% of a sugar having a disaccharide or less in terms of solid content) was removed. The total amount of water-soluble dietary fiber obtained by combining the sugar condensate obtained in (2) and the sugar condensate obtained in (3) was 144 g, and the dietary fiber content was 99% or more. Therefore, the yield from 182 g of the raw material was 79.1%.

Example 8: Production of sugar condensate by 10 cycles of reuse of enzyme-treated low molecular fractions as raw material (1) Sugar condensation reaction The same operation as in Example 5 (1) was performed.

(2) Separation of low-molecular fraction The same operation as in Example 5 (2) was performed.

(3) 10 cycles of reuse of low molecular fractions as raw material After blending the low molecular fraction obtained in (2) above with candy, which is the raw material for the sugar condensation reaction, and subjecting it to a sugar condensation reaction as in Example 7. The operation of separating the low-molecular fraction again by the method (2) was defined as one cycle, and the cycle was repeated 10 cycles. The total amount of water-soluble dietary fiber combining the sugar condensate obtained in (2) above and the sugar condensate obtained in (3) was 792 g, and the dietary fiber content was 99% or more. Therefore, the yield from 920 g of raw material was 86.1%.

  The yield (%) of the water-soluble dietary fiber obtained in Examples 5 to 8 is summarized in Table 4. Even when the sugar condensate composition is enzymatically treated for the purpose of increasing the dietary fiber content, the low-molecular fraction fractionated from the enzyme-decomposable composition is mixed with the raw sugar and the sugar condensation is performed again in the same manner as in Examples 1-4. It was found that a sugar condensate rich in dietary fiber can be produced with a very high yield by using it in the reaction. From Examples 7 and 8, it was shown that a sugar condensate having a water-soluble dietary fiber content of 99% or more can be produced with a very high yield. Furthermore, it was shown that the yield can be improved by increasing the number of times the low molecular fraction is reused (recycled). In addition, it was possible to reduce the environmental load by not discarding the low molecular fraction. When the low molecular fraction fractionated from the enzymatic decomposition composition was used again for the sugar condensation reaction as in Example 2 (Example 6), the yield was higher than when the condensation reaction was not performed again (Example 5). improves. In addition, when the low molecular fraction is mixed with the raw sugar and subjected to the sugar condensation reaction again (Examples 7 and 8), the low molecular fraction fractionated from the enzymatic decomposition composition is directly used again for the sugar condensation reaction. The yield was further improved as compared with (Example 6). Although not bound by the following theory, the yield rate is slightly lower when the low molecular fraction fractionated from the enzymatic degradation composition is used again for the sugar condensation reaction. This is probably because the sugar inhibited the sugar condensation reaction.

Sensory evaluation test For the purpose of comparing various sugar condensates (water-soluble dietary fiber), respective 10 mass% aqueous solutions were prepared and the tastes were compared. Sensory evaluation of the prepared aqueous solution was performed by 10 panelists, and the taste quality was evaluated. The taste quality is indicated by an evaluation of very good (◎), good (◯), normal (△), and bad (×), and the flavor is very good (◎), good (○), normal (△) ), Bad (×) evaluation. As comparative examples, “Lites” (manufactured by Danisco Japan) and “Lites II” (manufactured by Danisco Japan), which are polydextroses of commercially available water-soluble dietary fibers, and “Pine Fiber” (Matsutani Chemical), which is an indigestible dextrin, are used. Kogyo Co., Ltd.) and “Fiber Sol 2” (Matsuya Chemical Co., Ltd.) were used. The evaluation results were as shown in Table 5.

  Thus, it was confirmed that the sugar condensate obtained by the production method of the present invention is almost tasteless and odorless like conventional dietary fibers. That is, it was shown that the sugar condensate obtained by the production method of the present invention can be used as a food excipient or a bulking agent without any problem in various foods and drinks.

Example 9: Production of a sugar condensate by reusing a low molecular fraction (9 sugars or less) as a raw material (1) Sugar condensation reaction The same operation as in Example 1 (1) was performed.

(2) Separation of low-molecular fraction Subsequently, using a resin fractionator (manufactured by Nippon Nissui Co., Ltd.), a low-molecular fraction containing 9 sugars or less (a fraction containing 9% or less sugars in terms of solid content) Minutes). The obtained water-soluble dietary fiber was 28.8 g, and the dietary fiber content was 92%. Therefore, the yield from 100 g of the raw material was 28.8%.

(3) Reuse of low molecular fraction as raw material Further, the low molecular fraction (20 g of solid content) separated in (2) above is concentrated to a solid content of 70%, and 80 g of water candy (DE87, Japan) And re-used as a raw material for sugar condensation so as to have a solid concentration of 70%. After adding and mixing 2% (per solid content) activated carbon (manufactured by Futamura Chemical Co., Ltd.), heat treatment, activated carbon filtration, decolorization filtration, and decolorization with an ion exchange resin were similarly performed, and the mixture was concentrated with an evaporator. Thereafter, a low molecular fraction of 9 sugars or less (a fraction containing 100% sugar of 9 sugars or less in terms of solid content) was removed using a resin fractionator.
The total amount of water-soluble dietary fiber obtained by combining the sugar condensate obtained in (2) above and the sugar condensate obtained in (3) was 57.6 g, and the dietary fiber content was 95%. Therefore, the yield from 180 g of raw material was 32.0%.

Example 10: Production of a sugar condensate by reusing low molecular fractions as saccharification resources (starch) (1) Sugar condensation reaction The same operation as in Example 1 (1) was performed.

(2) Separation of low molecular fraction The same operation as in Example 1 (2) was performed.

(3) Reuse of low molecular fraction to saccharification raw material (starch) Further, 54 g of corn starch (manufactured by Nippon Food Chemical Co., Ltd.) per solid content of the low molecular fraction (solid content 13.5 g) separated in (2) above. And recycled as a saccharification raw material so that the solid content concentration becomes 20%. The pH was adjusted to 6.2 with a 20% sodium hydroxide solution, and 0.1% by weight of α-amylase (Chrytase T-5, manufactured by Daiwa Kasei Co., Ltd.) was added and liquefied at 105 ° C. for 2 hours. The liquefied solution was adjusted to pH 4.7 with a 5% hydrochloric acid solution, and amyloglucosidase (dextrozyme DXJ, manufactured by Novozyme) was added at 0.35% by weight for saccharification for 48 hours. After the enzyme treatment, the enzyme was inactivated by boiling to stop the action of amyloglucosidase. This solution was purified by decolorization filtration using activated carbon, desalting using an ion exchange resin, and the like, and then concentrated to a solid concentration of 70% with an evaporator.

(4) Sugar condensation reaction After adding and mixing 2% (per solid content) of activated carbon (Futamura Chemical Co., Ltd.) to the saccharified solution using the low molecular fraction obtained in (3) above, a heating reactor (ADVANTEC) And heated at 180 ° C. for 10 minutes to obtain a sugar condensate composition sample. The sample after the reaction was cooled to room temperature, and this sample was made into a 20% aqueous solution per solid content, and then the activated carbon was completely removed by filtration to obtain a soluble carbohydrate. The obtained carbohydrate fraction was decolorized and filtered with activated carbon and decolorized with an ion exchange resin, and then concentrated with an evaporator. Thereafter, using a resin fractionator, a low molecular fraction having a disaccharide or less (a fraction containing 94.3% of a sugar having a disaccharide or less in terms of solid content) was removed. The total amount of water-soluble dietary fiber combining the sugar condensate obtained in (2) above and the sugar condensate obtained in (4) was 128.1 g, and the dietary fiber content was 92%. Therefore, the yield from 154 g of the raw material was 83.2%.

Example 11: Production of sugar condensate by reusing polydextrose low molecular weight fraction as raw material (1) Polydextrose condensation reaction Glucose with a solid content of 89 g ( manufactured by Nippon Shokuhin Kako), sorbitol with a solid content of 10 g (Sorbit, Mitsubishi) Chemical Foodtech Co., Ltd.), 1 g of citric acid (manufactured by Kanto Chemical Co., Inc.) with a solid content of 1 g is added and mixed, then charged into a heating reactor (ADVANTEC Co., Ltd.), heated at 180 ° C. for 10 minutes, and a sugar condensate composition sample Got. The sample after the reaction was cooled to room temperature, and this sample was made into a 20% aqueous solution per solid content to obtain a soluble carbohydrate. The obtained carbohydrate fraction was decolorized and filtered with activated carbon and decolorized with an ion exchange resin, and then concentrated with an evaporator.

(2) Separation of low-molecular fraction Subsequently, using a resin fractionator (manufactured by Nippon Nissui Co., Ltd.), a low-molecular fraction of disaccharide or less (sugar of disaccharide or less is 74.1% in terms of solid content). Containing fractions). The obtained water-soluble dietary fiber was 72.0 g, and the dietary fiber content was 92%. Therefore, the yield from 100 g of the raw material was 72.0%.

(3) Reuse of low molecular fractions as raw materials Further, the low molecular fraction (solid content: 18.0 g) separated in (2) above was concentrated to a solid content concentration of 70%, and glucose (Japanese food) with a solid content of 73 g was obtained. Kako), sorbitol with a solid content of 8.2 g (Sorbit, manufactured by Mitsubishi Chemical Foodtech Co., Ltd.), and citric acid with a solid content of 0.8 g (manufactured by Kanto Chemical Co., Ltd.) to a solid content concentration of 70%. Reused as a raw material for polydextrose. Similarly, heat treatment, activated carbon decolorization filtration, purification with an ion exchange resin were performed, and the mixture was concentrated with an evaporator. Thereafter, using a resin fractionator, a low molecular fraction having a disaccharide or less (a fraction containing 76.9% of a sugar having a disaccharide or less in terms of solid content) was removed. The total amount of water-soluble dietary fiber obtained by combining the polydextrose obtained in (2) and the polydextrose obtained in (3) was 144 g, and the dietary fiber content was 92%. Therefore, the yield from 182 g of the raw material was 79.1%.

Example 12: Reuse of polydextrose low molecular weight fraction as raw material Production of sugar condensate by 10 cycles (1) Polydextrose condensation reaction The same operation as in Example 11 (1) was performed.

(2) Separation of low-molecular fraction The same operation as in Example 11 (2) was performed.

(3) 10 cycles of reuse of polydextrose low molecular fraction for raw materials After blending the low molecular fraction obtained in (2) above with a raw material for polydextrose reaction in the same manner as in Example 11, sugar condensation reaction was performed. The operation of separating the low-molecular fraction again by the method (2) was defined as one cycle, and the cycle was repeated 10 cycles. The total amount of water-soluble dietary fiber combining the sugar condensate obtained in (2) above and the sugar condensate obtained in (3) was 792 g, and the dietary fiber content was 92%. Therefore, the yield from 965 g of the raw material was 86.1%.

  The yield (%) of the water-soluble dietary fiber obtained in Examples 11 to 12 is summarized in Table 6. Yield of sugar condensate (polydextrose) rich in dietary fiber is extremely high by mixing the low molecular fraction fractionated from the sugar condensate composition (polydextrose) with the raw sugar and using it again in the sugar condensation reaction. (Examples 11 and 12). In addition, it was possible to reduce the environmental load by not discarding the low molecular fraction.

Example 13: Production of sugar condensate by reusing low molecular fraction generated during production of indigestible dextrin as raw material for sugar condensate (1) Production of indigestible dextrin Corn starch ( manufactured by Nippon Shokuhin Kako Co., Ltd.) 1000% 30 ml of hydrochloric acid solution was added by spraying, mixed uniformly for 10 minutes in a mixer, and dried using an air dryer at 50 ° C. until the water content reached 4%. Next, using a heating apparatus in which an oil bath was combined with a rotating glass eggplant-shaped flask, the reaction was performed by heating at 160 ° C. for 30 minutes to obtain roasted dextrin. 2 L of water was added to the obtained roasted dextrin to dissolve it, adjusted to pH 6.0 with 20% sodium hydroxide solution, and 0.2 wt% of α-amylase (Termamyl 200L, Novozyme) was added. And then hydrolyzed at 85 ° C. for 1 hour. Next, the solution was cooled to room temperature, adjusted to pH 5.0 with a 5% hydrochloric acid solution, added with 0.2% by weight of amyloglucosidase (manufactured by Sigma), and hydrolyzed at 60 ° C. for 38 hours. After the enzyme treatment, the enzyme was inactivated by boiling to stop the action of amyloglucosidase. This solution was purified by decolorization filtration with activated carbon, desalting with an ion exchange resin, or the like. Then, after concentrating to about 40%, using a resin fractionation device (manufactured by Nippon Nuisui Co., Ltd.), a low molecular fraction of 2 sugars or less (sugar of 2 sugars or less is converted to 92.0% in terms of solid content) The containing fraction) was removed. The water-soluble dietary fiber obtained was 525 g, and the dietary fiber content was 91.6%. Therefore, the yield from 1000 g of raw material was 52.5%.

(2) Reuse of low molecular fraction generated during production of indigestible dextrin as a raw material for sugar condensate The low molecular fraction (solid content 425 g) separated in (1) above is concentrated to a solid content concentration of 70%, It was blended with 1700 g of water candy (DE87, manufactured by Nippon Shokuhin Kako Co., Ltd.) per solid content, and reused as a raw material for sugar condensation reaction so that the solid content concentration became 70%. After adding and mixing 2% (per solid content) activated carbon (Futamura Chemical Co., Ltd.), the mixture was put into a heating reactor (ADVANTEC Co., Ltd.) and heated at 180 ° C. for 10 minutes to obtain a sugar condensate composition sample. The sample after the reaction was cooled to room temperature, and this sample was made into a 20% aqueous solution per solid content, and then the activated carbon was completely removed by filtration to obtain a soluble carbohydrate. The obtained carbohydrate fraction was decolorized and filtered with activated carbon and decolorized with an ion exchange resin, and then concentrated with an evaporator.

  The water-soluble dietary fiber obtained in (2) was 1913 g, and the dietary fiber content was 85.0%. The total amount of water-soluble dietary fiber combining the indigestible dextrin obtained in (1) above and the sugar condensate obtained in (2) was 2438 g, so the yield from 2700 g of the raw material was 90.3%. It was.

As an example of a process flow in which a low molecular fraction in a sugar condensate is fractionated, added to a raw sugar, and a sugar condensation reaction is performed again, a process in which the raw sugar to which the low molecular fraction is added is subjected to a sugar condensation reaction as it is It is the figure which showed the flow. The flow of reusing the separated low-molecular fraction as a raw material carbohydrate is shown by a dotted line. As an example of a process flow in which a low molecular fraction in a sugar condensate is fractionated, added to a raw sugar, and a sugar condensation reaction is performed again, the raw sugar to which the low molecular fraction is added is hydrolyzed and then condensed. It is the figure which showed the process flow made to react. The flow of reusing the separated low-molecular fraction as a raw material carbohydrate is shown by a dotted line. As an example of a process flow in which a low molecular fraction in a sugar condensate is fractionated, added to a raw sugar, and a sugar condensation reaction is performed again, the low molecular fraction is added to another reaction system to cause a sugar condensation reaction. It is the figure which showed the process flow. A process flow was shown in which the low molecular fraction produced by the production of indigestible dextrin was added to another reaction system using starch syrup. The flow of reusing the separated low-molecular fraction as a raw material carbohydrate is shown by a dotted line.

Claims (9)

A method for producing a sugar condensate or a reduced product thereof,
(A) A saccharide condensate composition obtained by subjecting one or more saccharides or derivatives thereof to a saccharide condensation reaction or an enzyme-decomposable composition thereof, and a saccharide having a degree of polymerization of 9 or less in terms of solids % Fraction (low molecular fraction) and other fractions (here, the low molecular fraction contains the anhydrosugar produced by the sugar condensation reaction) , then
(B) The following steps (B-1a), (B-1) and (B-2):
(B-1a) Adjust the solid content concentration of the low molecular fraction to 15-99%,
(B-1) A sugar condensate composition or an enzyme-decomposing composition thereof by subjecting the low molecular fraction obtained in step (B-1a) to a sugar condensation reaction together with one or more saccharides or derivatives thereof And (B-2) a step of dividing the sugar condensate composition obtained in step (B-1) or its enzymatic degradation composition into a low molecular fraction and other fractions. Or it is performed twice or more (however, when the step (B-2) corresponds to the final step, the step (B-2) may be omitted)
The manufacturing method characterized by the above-mentioned.   The manufacturing method of Claim 1 which adjusts the solid content density | concentration of a low molecular fraction to 50 to 99% in a process (B-1a).   The process according to claim 1 or 2, wherein in the step (B-1a), the solid content concentration of the low-molecular fraction is adjusted by a concentration treatment.   The production method according to any one of claims 1 to 3, wherein the sugar condensation reaction is carried out in the presence of one or more catalysts selected from inorganic acids, organic acids, mineral substances and activated carbon.   The manufacturing method as described in any one of Claims 1-4 whose water-soluble dietary fiber content in a sugar condensate is 70% or more.   The manufacturing method as described in any one of Claims 1-5 by which saccharide | sugar condensation reaction is performed on the temperature conditions of 100 to 300 degreeC.   In a process (B), a process (B-1a), a process (B-1), and a process (B-2) are repeated 2 times or more, It is characterized by the above-mentioned. Production method.   The manufacturing method as described in any one of Claims 1-7 which further includes the process of carrying out the reduction process of the manufactured sugar condensate.   A sugar condensate or a reduced product thereof is produced by the production method according to any one of claims 1 to 8, and then the sugar condensate or the reduced product thereof is added to a food or drink or a raw material thereof. The manufacturing method of food-drinks.

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