JP3044465B2 - Xylobiitol crystals, honey-containing crystals containing the same, and methods for their production and use - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a xylobiitol crystal, a nectar-containing crystal containing the same, and a production method and use thereof.

(Prior Art) Xylobiitol is a sugar alcohol obtained by reducing xylobiose, and is disclosed in Kazumasa Shimizu et al.
As described in Japanese Patent Publication No. 62 and the like, the sweetness of the obtained aqueous solution containing xylobiitol as a main component is a high-quality sweet taste without habit and tingling, and the sweetness is about the same as that of sugar. It is as low as about 40%, hardly digested by human digestive organs, well assimilated by useful bacteria in the large intestine, such as bifidobacteria, and hardly fermented by oral bacteria.

Due to these properties, solutions containing xylobiitol as the main component have been developed for various uses as a sweetness source for low-calorie foods, diet foods, low carious foods, health foods and the like.

(Problems to be Solved by the Invention) However, xylobiitol has conventionally been considered to have excellent properties, but it has not been obtained in the form of crystals, nectar crystals or powder, and is usually in the form of an aqueous solution. And many of its physicochemical properties were not known, and its use was in a very limited range.

(Means for Solving the Problems) In order to solve the above problems, the present inventors have conducted intensive studies on a method for producing xylobiitol crystals and a honey-containing crystal containing the same, and as a result, hardwood, cottonseed and cottonseed. A xylanase, which is an enzyme that mainly produces xylobiose, is allowed to act on an aqueous solution of xylan extracted from shells or the like to obtain xylo-oligosaccharides at a concentration of about 30% by weight (hereinafter sometimes simply referred to as%).
The resulting concentrate was passed through a column packed with activated carbon to isolate xylobiose, which was purified and concentrated to crystallize xylobiose, and after naturation, obtained xylobiose having a purity of 99% or more.

Next, the xylobiose crystals were hydrogenated in the presence of a Raney nickel catalyst, purified, and then concentrated to 80% to obtain a highly pure xylobiitol aqueous solution having a purity of 98% or more.

A portion of the high-purity xylobiitol aqueous solution was taken, ethanol was added thereto, and heating, cooling, and standing were repeated for about 3 weeks. As a result, crystals were deposited on the inner wall.

The crystals were separated and added as seed crystals to the high-purity xylobiitol aqueous solution prepared to a concentration of 75%, and the crystals were promoted with slow stirring to grow the crystals. The crystals were washed with water to obtain more pure crystals.

The high-purity crystals were dissolved in water, treated in the same manner and recrystallized, and further high-purity crystals were collected. The physicochemical properties of the crystals were examined. Found that it is a xylobiitol crystal having properties, succeeded in obtaining a xylobiitol crystal and a honey-containing crystal containing it, succeeded in developing a production method thereof on an industrial scale, We succeeded in developing those applications and completed the present invention.

That is, the present invention is represented by the molecular formula C ₁₀ H ₂₀ C ₉ and has a melting point of
Xylobiitol crystals having a temperature of 129.5 ° C to 132.5 ° C.

Further, the present invention is represented by the molecular formula C ₁₀ H ₂₀ O ₉ and has a melting point
It is a nectar-containing crystal containing xylobiitol crystals having a temperature of 129.5 ° C to 132.5 ° C.

Further, the present invention is the xylobiitol crystal as described above, wherein the xylobiitol crystal has a xylobiitol purity of 65% by weight or more based on dry solid matter.

Further, the present invention is the nectar-containing crystal containing xylobiitol crystals as described above, wherein the xylobiitol crystals have a xylobiitol purity of 65% by weight or more based on dry solid matter.

Further, the present invention is the xylobiitol crystal as described above, wherein the xylobiitol crystal is a composition.

Further, the present invention is the above-mentioned honey-containing crystal containing xylobiitol crystals, wherein the honey-containing crystal containing xylobiitol crystals is a composition.

Further, the present invention is the xylobiitol crystal as described above, wherein the xylobiitol crystal is a molded product.

Further, the present invention is the honey-containing crystal containing xylobiitol crystals as described above, wherein the honey-containing crystal containing xylobiitol is a molded product.

Further, the present invention is characterized by crystallizing xylobiitol crystals represented by the molecular formula C ₁₀ H ₂₀ O ₉ and having a melting point of 129.5 ° C. to 132.5 ° C. from an aqueous solution of xylobiitol, and collecting the crystals. This is a method for producing xylobiitol crystals.

Further, the present invention is characterized by crystallizing xylobiitol crystals represented by the molecular formula C ₁₀ H ₂₀ O ₉ and having a melting point of 129.5 ° C. to 132.5 ° C. from an aqueous solution of xylobiitol, and collecting or solidifying the crystals. Is a method for producing a honey-containing crystal containing xylobiitol crystals.

Further, the present invention is the method for producing xylobiitol crystals as described above, wherein the xylobiitol purity of the xylobiitol aqueous solution is 65% by weight or more based on dry solids.

Further, the present invention is the method for producing a nectar-containing crystal containing xylobiitol as described above, wherein the xylobiitol purity of the xylobiitol aqueous solution is 65% by weight or more based on dry solids.

Further, the present invention is the method for producing xylobiitol crystals described above or above, wherein the crystallization temperature is 0 to 95 ° C.

Further, the present invention is a honey-containing crystal containing the xylobiitol crystal described above or described, wherein the crystallization temperature is 0 to 95 ° C.

Further, the present invention is the method for producing a xylobiitol crystal according to any one of the above or the above, wherein a seed crystal is allowed to coexist in the aqueous solution of xylobiitol.

Further, the present invention is the method for producing a honey-containing crystal containing xylobiitol crystals according to any one of the above or the above, wherein a seed crystal is allowed to coexist in an aqueous solution of xylobiitol.

Further, the present invention is a food or drink characterized by containing xylobiitol crystals.

Further, the present invention is a food or drink characterized by containing a honey-containing crystal containing xylobiitol crystals.

The xylobiitol crystal of the present invention has the following physicochemical properties.

(1) Elemental analysis Theoretical value C = 42.26% H = 7.09% O = 50.65% Measured value C = 42.39% H = 7.12% O = 50.49% (2) Molecular weight 284.3 (3) Melting point of crystal 129.5 ° C to 132.5 ° C ( 4) Differential scanning calorimetric analysis of crystal Endothermic maximum value = 136.0 ° C to 141.0 ° C (measured at a heating rate of 10 ° C / min using a differential scanning calorimeter) (5) Specific rotation ▲ [α] ²⁰ _D ▼ = -42.01 ゜ (20.16 g /) (6) Ultraviolet absorption When measured as an aqueous solution, there is no particular characteristic absorption.

(7) Infrared absorption spectrum 1 mg of crystalline xylobiitol and 200 mg of dehydrated KBr were mixed and stirred to form a transparent tablet (0.6 mm thick), and the infrared absorption spectrum was measured. The results are shown in Table 1.

Wavelength absorption in Table 1 infrared radiation is measured ^{3100~3600 (cm -1) 2800~3000 1000~1200 980~1000} 920~ 960 880~ 920 absorption Among 880cm ^-1 ~920cm ^-1 is beta-1, This supports the existence of four bonds.

(8) Solubility The solubility of xylobiitol crystals in water at room temperature (25 ° C.) is about 70%.

(9) Physical properties and color of substance Colorless and transparent crystals, and fine crystals are in the form of white powder. It has a sweetness of 35-40% of sugar and no odor. No hygroscopicity or deliquescent. When the xylobiitol crystals are dissolved in water, the aqueous solution is neutral or slightly acidic.

(10) Solubility in various drugs Easily soluble in water, 0.1N-NaOH, 0.1N-HCl. Soluble in hot ethanol. Insoluble in benzene, chloroform and ethyl acetate.

(11) Constituent Sugar When the saccharide obtained by hydrolysis with 4% trifluoroacetic acid is analyzed by high performance liquid chromatography, it is composed of equimolar amounts of D-xylose and D-xylitol.

(12) Nuclear magnetic resonance spectrum 100 mg of crystal xylobiitol was dissolved in 0.6 ml of heavy water, and nuclear magnetic resonance spectra of carbon and proton were measured.

^{In 13} C-NMR, the signal indicating the anomeric carbon of the xylol residue is at 103.3 ppm, and its ¹ J _CH is 162.4 Hz.
Therefore, it can be seen that there is a β bond between the xylose residue and the xylitol residue.

In addition, the signal representing the carbon at the 4-position of xylitol is significantly shifted to the lower magnetic field side, indicating that there is a 1,4 bond.

From the above facts, it is determined that the crystal of the present invention is xylobiitol having the following structure.

(13) X-ray crystal structure analysis When a xylobiitol single crystal crystallized from an 85% aqueous xylobiitol solution was analyzed by X-ray, the lattice constant of the crystal of the present invention was a = 5.114 °, b = 9.201
Å, c = 13.6163Å, β = 99.64 ゜ monoclinic, number of molecules per unit cell = 2, unit cell volume = 635.3
^{３ 3} , density = 1.468 g / cm ³ , space group is P2 ₁ (# 4)
Turned out to be.

Xylobiitol having the above structure is a disaccharide alcohol in which xylitol, a reduced product of xylose, is β-1,4 bonded to the reducing end of xylose, which is a pentose,
4- (β-D-xylopyranosyl) -D-xylitol.

Xylobiitol can be obtained, for example, by preparative fractionation from reduced xylo-oligosaccharides described in JP-A-62-278961, and as described in JP-A-61-285999. Xylobiose can also be obtained by isolating xylobiose from xylooligosaccharide and hydrogenating it using a catalyst such as Raney nickel.

The origin of the reduced xylo-oligosaccharide or xylo-oligosaccharide is not limited, and the production method is also free.

As a raw material for producing xylo-oligosaccharides, almost all natural products containing xylan can be used, but among economical restrictions, those having a high xylan content are preferable among raw materials.

Particularly preferred raw materials include hardwood such as bagasse, corn cob, cottonseed shell, birch, and beech, rice straw, beer lees, and the like.

In addition, xylan, xylo-oligosaccharide, reduced xylo-oligosaccharide, etc. may be chemically, biologically, or decomposed, polymerized, or synthesized from enzymes such as xylose, xylitol, glucose, sorbitol, and starch. There is no problem as a raw material for producing the xylobiitol of the present invention.

In addition, xylobiitol can be easily produced from xylose, xylitol, glucose, sorbitol, or the like, through a process such as synthesis, polymerization, and decomposition chemically or biologically or using an enzyme.

Hereinafter, a method for producing a xylobiitol crystal of the present invention and a honey-containing crystal containing the same will be described.

Xylobiitol aqueous solution for crystallization used in the present invention,
It is sufficient that the xylobiitol crystals of the present invention are precipitated, and the method for producing xylobiitol is not limited.

Normally, xylobiitol having a purity of 65% or more is desirably an aqueous solution having a concentration of 65% to 95%, and the solution temperature is preferably in a range of 0 to 95 ° C. where the solution is not frozen and heat loss is small in a manufacturing process. .

To adjust the viscosity of the solution, for example, methanol,
Ethanol, acetone, and the like can coexist freely.

In addition, the crystallization method is usually to take a supersaturated xylobiitol solution at a relatively high temperature of 40 to 95 ° C. in an auxiliary crystal can, and desirably coexist with 0.1 to 20% of a seed crystal. Just ask them to come out and make a mass kit.

As described above, the xylobiitol crystals of the present invention and the nectar-containing crystals containing the same can be obtained by adding the xylobiitol crystals or the nectar-containing crystals containing the same as seed crystals to a supersaturated xylobiitol solution. Crystallization can be performed relatively easily without the need.

The method for producing xylobiitol crystals and the nectar-containing crystals containing the same from the crystallized mass kit may be any method as long as the xylobiitol crystals, which are the object of the present invention, can be collected. One or two or more known methods such as a coating method and a spray-drying method can be freely used, and if the water content is small, it can be freely solidified.

Specifically, for example, the honey separating method is a method of separating a xylobiitol crystal and honey from a mass kit by a centrifugal separator, and washing the crystal by spraying a small amount of water or cold water as necessary. This method is easily possible, and this method is suitable for producing xylobiitol crystals of higher purity.

Other block grinding method, fluidized granulation method, kneading method,
Since the spray drying method does not separate nectar, the obtained nectar-containing crystals may contain trace amounts of sugar alcohols such as xylitol, xylitolitol, sorbitol, and mannitol as nectar components in addition to the xylobiitol crystals of the present invention. is there.

In the kneading method, which is one of the honey-containing methods, for example, a xylobiitol solution having a water content of 5 to 25%, preferably 6 to 20% is gradually cooled in a kneader, and is gradually cooled to a temperature lower than the melting point of the xylobiitol crystals. At temperature, preferably 10 ° C to 70 ° C
With the addition of a seed crystal of 0.1 to 70% by weight of solids in the solution,
Alternatively, they can be mixed without being added and formed into various shapes, for example, powder, granules, spheres, rods, plates, cubes, etc., to obtain powders or molded bodies of xylobiitol-containing honey crystals.

Xylobiitol crystals and honey-containing crystals containing the same are basically non-hygroscopic, but their physicochemical properties such as hygroscopicity, melting point and specific rotation vary depending on their purity.

Therefore, the purity of xylobiitol can be appropriately selected and used depending on the necessity.

In addition, xylobiitol crystals and honey-containing crystals containing them have sweetness, viscosity, heat resistance, acid resistance, resistance to fermentation, resistance to digestion, non-caries, body-giving properties, moisturizing properties, shine-giving properties, etc. Has excellent properties.

In addition, since it is selectively assimilated by useful intestinal bacteria, it is possible to freely produce foods, drinks, cosmetics, pharmaceuticals and the like utilizing these properties.

 Hereinafter, the present invention will be described in more detail.

The xylobiitol crystal of the present invention and the honey-containing crystal containing it can be used as a seasoning for sweetening as it is.

If necessary, for example, sugar, glucose, honey, candy starch, isomerized sugar, maltose, maple sugar, erythritol,
Xylitol, sorbitol, maltitol, lactitol, stevioside, dihydrochalcone, glycyrrhizin, saccharin, aspartame, α-glycosyl stevioside, arhat extract, glycine, alanine, etc. It may be used in combination with a bulking agent such as starch, dextrin, lactose, polydextrin and the like.

Further, among the xylobiitol crystals of the present invention and the honey-containing crystals containing the same, the powdery ones may be used as they are, or may be mixed with a bulking agent, an excipient, a binder, a disintegrant or the like as necessary. It can be freely formed into granules, spheres, tablets, rods, plates, cubes and the like.

In addition, the xylobiitol crystals of the present invention and the honey-containing crystals containing the same do not promote insulin secretion and are hardly digested and absorbed like other sugar alcohols. The calorie of food and drink using the contained honey-containing crystals can be reduced.

Therefore, the xylobiitol crystals of the present invention and the honey-containing crystals containing the same can be used as low-calorie foods and drinks for people with diabetes or obese people who are restricted in calories, such as beauty foods, healthy foods, diet foods. It can be used for sweetening etc.

In addition, the xylobiitol crystals of the present invention and the honey-containing crystals containing the same have the effect of activating the growth of intestinal useful bacteria. It can be used freely as an excipient, sweetener, taste improver, stabilizer and the like.

In addition, the xylobiitol crystals of the present invention and the honey-containing crystals containing the same can be used in foods and the like as sweeteners that hardly cause dental caries because they are hardly fermented by oral bacteria.

For example, chewing gum, chocolate, caramel, cookies, biscuits and other confectionery, cola, cider, juice, coffee, suitable for sweetening foods and drinks where low caries such as drinking water such as lactic acid bacteria beverages are desired, Further, it is also suitable as a sweetening agent for cosmetics and pharmaceuticals for preventing tooth decay such as gargle water and toothpaste.

The sweetness of xylobiitol crystals and the honey-containing crystals containing them is in harmony with various substances having other tastes such as sourness, salty taste, astringency, umami, bitterness, etc., acid resistance, heat resistance It can be freely used not only for the special cases described above but also for sweetening and taste improvement of ordinary foods and drinks, and quality improvement.

For example, soy sauce, powdered soy sauce, miso, powdered miso, moromi,
Hishio, various sprinkles, mayonnaise, dressing, vinegar, three tablespoons vinegar, powdered sushi vinegar, Chinese ingredients, tentsuyu, noodle soup,
It can be used freely as various seasonings such as sauce, ketchup, grilled meat sauce, curry roe, stew mushroom, soup mushroom, dashi mushroom, compound seasoning, mirin, new mirin, table sugar, coffee sugar and the like.

Also, for example, rice crackers, hail, okoshi, rice cakes, buns,
Uiro, bean paste, yokan, mizuyokan, nishikidama, jelly, castella, candy, etc., various sweets, bread, pie, biscuit, cracker, pudding, butter cream, custard cream, cream puff, waffle, sponge cake, donut, chocolate , Sweets such as chewing gum, caramel, candy, ice cream, ice cream, sherbet, etc., fruit syrup pickling, ice honey etc. syrups, flower paste, peanut paste, fruit paste etc., jam, marmalade, syrup pickling Fruits such as confectionery, processed foods of vegetables, breads, noodles, cooked rice, cereal processed foods such as artificial meats, pickles such as Fukujinzuke, Betarazuke, Senmaizuke, Rakkyozuke, Takuanzuke, Hakusaizuke Pickles, ham, sausage, kamaboko, chiku , Squid salt, sea urchin, squid salt, various delicacies such as dried fugu mirin, seaweed, wild vegetables, soybeans, small fish, shellfish, etc. , Vegetables such as potato salad, konbu-maki, dairy products, fish meat, meat, fruits, vegetables, cans, synthetic liquors, fruit liquors, liquors such as Western liquors, coffee, cocoa, juice, carbonated beverages, lactic acid As a sweetener for various drinks such as beverages, soft drinks such as lactic acid bacteria drinks, premix powders such as pudding mixes, hot cake mixes, etc., instant juices, instant coffees, instant shiroko, instant soups etc. Further, it can be freely used as a taste improver and a quality improver.

In addition, the xylobiitol crystals of the present invention and the honey-containing crystals containing the same are non-hygroscopic and have good fluidity. For example, chewing gum, vinegar, etc. It can also be advantageously used as an agent for preventing adhesion of wrapping paper and for improving slip.

It can also be used for raising the taste of feeds, feeds and the like for livestock, poultry, and other breeding animals such as honeybees, silkworms, and fish, and for activating the growth of useful intestinal bacteria in animals.

In addition, tobacco, toothpaste, lipstick, lip balm, oral medicine, troche, liver oil drop, mouth refresher, mouth flavor, mouthwash, etc. Various solid, paste, liquid, etc. It can be freely used as a taste improver, a quality improver, and the like.

Further, the xylobiitol crystals of the present invention and the honey-containing crystals containing the same are slightly moistened and are subjected to low-pressure compression molding to obtain various shapes such as molded sugar produced from granulated sugar, for example, a die-like shape. Since it can be freely shaped into fish, flowers, etc., suitable shaped sweeteners such as coffee and tea can be easily produced. In this case, for example, it is possible to add various sugars, artificial sweeteners, etc. to increase the sweetness, to color it with various edible pigments, and to further form it by containing various flavors. . Also,
In using the flavor, various flavors can be included in advance with an inclusion compound such as cyclodextrin.

Further, the xylobiitol crystals of the present invention or the honey-containing crystals containing the same are mixed with, for example, vitamins, antibiotics, lactic acid bacteria, bifidobacteria, and the like, and molded into various shapes such as granules and tablets for various uses. It can also be used for

Further, the xylobiitol crystals of the present invention or the honey-containing crystals containing the same can be easily converted into an anhydride simply by lightly drying with hot air, and thus can be used as a non-aqueous sugar alcohol for chemical reaction.

Therefore, for example, an ether derivative, an ester derivative or the like can be extremely easily produced from xylobiitol crystals by a non-aqueous chemical reaction.

These derivatives, xylobiitol crystals, and honey-containing crystals containing them can be advantageously used as surfactants, emulsifiers, reagents for enzyme reactions, bases for synthesizing various sugar-containing compounds, and the like.

(Examples) Hereinafter, the content of the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples. Further, in the following examples, all percentages are by weight unless otherwise specified.

Example 1 300 kg of bombed explosive birch was extracted with water, and this extract was used as a Streptomyces sp.
A xylo-oligosaccharide solution obtained by hydrolyzing with xylanase produced by 86, using an activated carbon and an ion-exchange resin in a conventional manner, and concentrating to a concentration of 50% (xylobiose content is 45% based on the solid content) 3% by weight of solids
Hydrogenation at a pressure of 150 kg / cm ² using Raney Nickel's catalyst with a xylobiitol content of 45%
To obtain 30 kg of a reduced xylo-oligosaccharide solution. The reduced xylo-oligosaccharide solution is purified by a conventional method, and 1 kg corresponding to the solid content is separately adjusted to a concentration of 33%. The xylobiitol fraction is collected using a column packed with activated carbon, and concentrated to a concentration of 80%.
370 g of a 99.5% xylobiitol aqueous solution was obtained. When 10 g of this high-purity xylobiitol aqueous solution was placed in an eggplant-shaped flask, and heating and cooling were repeated for about 3 weeks while adding ethanol and stirring, crystals were formed on the inner wall.

The crystals were collected by filtration and dried in a vacuum dryer at 60 ° C. overnight. 0.5 g of these crystals were used as seed crystals, and the resulting xylobiitol aqueous solution, which had been adjusted to a concentration of 85%, was added at a temperature of 30 ° C., and stirred for 20 hours while cooling to obtain a mass kit.

This mass kit was centrifuged to obtain 173.6 g of xylobiitol crystals having a purity of 99.8%.

The crystals were dried using a vacuum dryer at a temperature of 60 ° C. for 18 hours, and the melting point of the product was measured to be 130.5 ° C.

The results of elemental analysis show that the theoretical value is C = 42.26% and H
= 7.09% and O = 50.65%, respectively.
They were 39%, 7.12% and 50.49%.

Example-2 A xylo-oligosaccharide solution obtained in the same manner as in Example 1,
1 kg of the solid content was fractionated using a column packed with activated carbon, purified by a conventional method, concentrated to a concentration of 80%, and stirred overnight while cooling, and the precipitated crystals were collected by filtration to obtain 225 g of xylobiose crystals. .

The crystals are dissolved in water to a concentration of 50%, and the pressure is increased using a Raney Nickel catalyst of 2% based on the weight of the solid content.
After hydrogenation at 150 kg / cm ² and purification by the usual method,
The solution was concentrated to a concentration of 84% to obtain 265 g of an xylobiitol aqueous solution having a purity of 98.5%. This xylobiitol aqueous solution is heated at a temperature of 30
At 0.5 ° C., 0.5 g of a seed crystal was added, and the mixture was allowed to cool with stirring for 20 hours to obtain a mass kit.

The mass kit was poured into a stainless steel vat and allowed to stand at room temperature overnight to obtain a block-shaped mass.

The block-like mass was pulverized to obtain 221.8 g of a nectar-containing crystal containing the xylobiitol crystals of the present invention. The xylobiitol purity of the honey-containing crystals was 98.5%.

Example 3 Cation exchange of 1 kg of a 40% xylooligosaccharide aqueous solution (xylobiose purity 45%) obtained by hydrolyzing an aqueous extract of bombed explosives with the same enzyme as used in Example 1 into a sodium form The resin is fractionated, purified and concentrated by a conventional method, and a xylobiose aqueous solution having a purity of 82% and a concentration of 50%
7.3 g were obtained.

This xylobiose aqueous solution is 4% based on the solid content weight.
Hydrogenation at a pressure of 130 kg / cm ² using a Raney nickel catalyst, and concentration and purification by a conventional method, with a concentration of 88% and a purity of 81.5%
174 g of an aqueous solution of xylobiitol was obtained.

The xylobiose aqueous solution was put into a Labo Plastomill, and seed crystals (0.5 g) were added at a temperature of 20 ° C. and kneaded at a rotation speed of 40 rpm for 2 hours to obtain about 152 g of a nectar-containing crystal containing the xylobiitol crystals of the present invention.

The xylobiitol purity of the nectar-containing crystals containing the xylobiitol crystals was 81.5%.

Example-4 50 parts by weight of xylobiitol crystals obtained by the same method as in Example 1, 40 parts by weight of cocoa paste, aspartame
0.5 parts by weight were mixed and made into fine powder by a refiner, and then put in a conch and kneaded at a temperature of 50 ° C. for 24 hours.

Thereafter, while cooling to 31 ° C, the mixture was poured into a mold and solidified at 10 ° C.

This product has no hygroscopicity and is useful as a low-cariogenic chocolate having good sweetness.

Example-5 400 g of xylobiitol crystals were added to 450 g of milk in the same manner as in Example 1 corresponding to 2/3 of the blending amount, heated to boiling and cooled to room temperature, and 250 g of yolk was added to xylobiitol crystals. Add the remaining 1/3 and aspartame 3g, mix well and mix well.

450g of butter, which was loosened and creamed in advance,
Margarine was added gradually to a cream consisting of 450 g, and after creaming, 75 g of rum was mixed to produce a butter cream.

The product has a good mouthfeel and mouthfeel and is useful as a cream having good taste.

Example -6 A honey-containing crystal containing xylobiitol crystals obtained in the same manner as in Example 2 was added to 320 g of margarine that had been well unraveled.
g, 200 g of whole egg and 90 g of water and further creaming.

To this, 400 g of soft flour and 3 g of baking powder, which have been mixed in advance, are added and lightly mixed to obtain a dough.

This was squeezed into a rectangular shape and roasted at 165 ° C. for 12 minutes to produce a cookie.

This cookie was palatable and tasteless.

Example -7 Aspirin (50 parts by weight), xylobiitol crystal-containing nectar-containing crystals (15 parts by weight) obtained in the same manner as in Example 3, and corn starch (4 parts by weight) were mixed well, and then 5 m thick using a tableting machine.
m, tablets having a diameter of 6 mm were produced.

This tablet is not hygroscopic, has sufficient physical strength,
And the disintegration property in water was good.

(Effect of the Invention) As described above, the xylobiitol crystals of the present invention and the honey-containing crystals containing the same are useful as various foods, pharmaceuticals and the like, and by carrying out the present invention, the xylobiitol crystals and It becomes possible to produce a honey-containing crystal containing the same, and it is possible to industrially advantageously produce various foods, pharmaceuticals and the like using the same.

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Koichi Kataura 134-1 Tsuda, Fuji City, Shizuoka Prefecture Towa Kasei Kogyo Co., Ltd. (72) Inventor Yoshifumi Ishii 134-1 Tsuda Tsuda Chemical, Fuji City, Shizuoka Prefecture (72) Inventor Kazuaki Kato 2-1-2 Otemachi, Chiyoda-ku, Tokyo Towa Kasei Kogyo Co., Ltd. (56) References JP-A-62-278962 (JP, A) ( 58) Investigated field (Int.Cl. ⁷ , DB name) C07H 15/04 A23L 1/236 C13K 13/00 CAPLUS (STN) REGISTRY (STN)

Claims (18)

(57) [Claims] 1. A compound represented by the molecular formula C ₁₀ H ₂₀ O ₉ and having a melting point of 129.5 ° C.
Xylobiitol crystals at 〜132.5 ° C. 2. A compound represented by the molecular formula C ₁₀ H ₂₀ O ₉ and having a melting point of 129.5 ° C.
Honey-containing crystals containing xylobiitol crystals at ト ー ル 132.5 ° C. 3. The xylobiitol crystal according to claim 1, wherein the xylobiitol crystal has a purity of at least 65% by weight based on dry solids. 4. The honey-containing crystal containing xylobiitol crystals according to claim 2, wherein the xylobiitol crystals have a xylobiitol purity of 65% by weight or more based on dry solids. 5. The xylobiitol crystal according to claim 1, wherein the xylobiitol crystal is a composition. 6. The honey-containing crystal containing xylobiitol crystals according to claim 2, wherein the honey-containing crystals containing xylobiitol crystals are a composition. 7. The xylobiitol crystal according to claim 1, wherein the xylobiitol crystal is a molded product. 8. The honey-containing crystal containing xylobiitol crystals according to claim 2, wherein the honey-containing crystals containing xylobiitol are shaped products. 9. An aqueous solution of xylobiitol having a molecular formula of C ₁₀ H
_A method for producing xylobiitol crystals, which comprises crystallizing xylobiitol crystals represented by ₂₀ O ₉ and having a melting point of 129.5 ° C. to 132.5 ° C., and collecting the crystals. 10. An aqueous solution of xylobiitol, which has a molecular formula of C
Production of honey-containing crystals containing xylobiitol crystals characterized by crystallizing xylobiitol crystals represented by ₁₀ H ₂₀ O ₉ and having a melting point of 129.5 ° C. to 132.5 ° C., and collecting or solidifying the crystals. Method. 11. The method for producing xylobiitol crystals according to claim 9, wherein the xylobiitol purity of the xylobiitol aqueous solution is 65% by weight or more per dry solid. 12. The process for producing xylobiitol-containing honey-containing crystals according to claim 10, wherein the xylobiitol concentration of the xylobiitol solution in the aqueous solution of xylobiitol is 65% by weight or more based on the dry solid matter. 13. The method for producing xylobiitol crystals according to claim 9, wherein the crystallization temperature is 0 to 95 ° C. 14. The method for producing honey-containing crystals containing xylobiitol crystals according to claim 10, wherein the crystallization temperature is from 0 to 95 ° C. 15. The method for producing xylobiitol crystals according to claim 9, wherein a seed crystal is allowed to coexist in the aqueous solution of xylobiitol. 16. The method for producing honey-containing crystals containing xylobiitol crystals according to claim 10, wherein the seed crystals are allowed to coexist in the aqueous solution of xylobiitol. 17. A food or drink comprising xylobiitol crystals. 18. A food or drink comprising honey-containing crystals containing xylobiitol crystals.