JPH0112761B2 - - Google Patents
Info
- Publication number
- JPH0112761B2 JPH0112761B2 JP60230855A JP23085585A JPH0112761B2 JP H0112761 B2 JPH0112761 B2 JP H0112761B2 JP 60230855 A JP60230855 A JP 60230855A JP 23085585 A JP23085585 A JP 23085585A JP H0112761 B2 JPH0112761 B2 JP H0112761B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- acid
- starch hydrolyzate
- polysaccharide
- starch
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920002472 Starch Polymers 0.000 claims description 32
- 235000019698 starch Nutrition 0.000 claims description 32
- 239000008107 starch Substances 0.000 claims description 32
- 150000004676 glycans Chemical class 0.000 claims description 17
- 229920001282 polysaccharide Polymers 0.000 claims description 17
- 239000005017 polysaccharide Substances 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000000346 sugar Nutrition 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 6
- 239000000376 reactant Substances 0.000 description 5
- 150000008163 sugars Chemical class 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 235000019658 bitter taste Nutrition 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000005846 sugar alcohols Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 3
- 229920001353 Dextrin Polymers 0.000 description 3
- 239000004375 Dextrin Substances 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 235000019425 dextrin Nutrition 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 102000004366 Glucosidases Human genes 0.000 description 2
- 108010056771 Glucosidases Proteins 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 102000004139 alpha-Amylases Human genes 0.000 description 2
- 108090000637 alpha-Amylases Proteins 0.000 description 2
- 229940024171 alpha-amylase Drugs 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000000378 dietary effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- AYRXSINWFIIFAE-UHFFFAOYSA-N O6-alpha-D-Galactopyranosyl-D-galactose Natural products OCC1OC(OCC(O)C(O)C(O)C(O)C=O)C(O)C(O)C1O AYRXSINWFIIFAE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- DLRVVLDZNNYCBX-CQUJWQHSSA-N gentiobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 DLRVVLDZNNYCBX-CQUJWQHSSA-N 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、人体内で消化され難い、いわゆる低
カロリーの多糖類の製造法に関し、この多糖類は
低カロリーであるため、摂取カロリーや炭水化物
の摂取を制限する必要のある人の食餌療法等のた
めの食品素材として利用されるものである。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a method for producing so-called low-calorie polysaccharides that are difficult to digest in the human body. It is used as a food material for dietary therapy of people who need to limit their intake of food.
従来の技術
従来、上述したような低カロリー多糖類の製造
法としては、グルコース、マルトースもしくはそ
れらの混合物のいずれかを、ポリカルボン酸触媒
の存在下に、更に所望ならば糖アルコールとの共
存下に、減圧下に加熱重合させる方法（特公昭53
−47280号）ならびに澱粉又は澱粉水解物を、ポ
リカルボン酸、その無水物と減圧下に加熱する方
法（特公昭56−29512号）が提案されている。BACKGROUND ART Conventionally, as a method for producing low-calorie polysaccharides as described above, glucose, maltose, or a mixture thereof is used in the presence of a polycarboxylic acid catalyst and, if desired, in the coexistence of a sugar alcohol. The method of heating polymerization under reduced pressure
-47280) and a method of heating starch or starch hydrolyzate with polycarboxylic acid and its anhydride under reduced pressure (Japanese Patent Publication No. 56-29512).
しかしながら、これらの方法のうち、特公昭53
−47280号の方法では、出発物質としてのグルコ
ース、マルトース又はそれらの混合物を、ポリカ
ルボン酸の存在下に糖アルコールと、これら糖類
の分解点以下の温度で加熱重合させるものであ
り、その場合グルコース又はマルトースについて
の種々の結合方式の可能性のうち、主として１→
６結合を優勢すると脱水縮合反応により重合体を
形成し、その際触媒として用いたポリカルボン酸
はグルコース重合体にエステル結合し、さらに重
合体間をエステル結合によつて架橋して大分子の
重合体を形成するに至る。なお、上記重合反応に
おいて糖アルコールはグルコース重合体の還元末
端基と脱水縮合して重合体に組込まれ、反応中の
着色を抑制する作用を有するものである。 However, among these methods,
In the method of No. 47280, glucose, maltose, or a mixture thereof as a starting material is polymerized by heating with a sugar alcohol in the presence of a polycarboxylic acid at a temperature below the decomposition point of these sugars. Or, among the various possible binding methods for maltose, mainly 1→
When 6 bonds predominate, a polymer is formed by a dehydration condensation reaction, and the polycarboxylic acid used as a catalyst forms an ester bond to the glucose polymer, and the polymers are further cross-linked by ester bonds to form a large molecule polymer. This leads to the formation of a union. In the above polymerization reaction, the sugar alcohol is incorporated into the polymer through dehydration condensation with the reducing end group of the glucose polymer, and has the effect of suppressing coloration during the reaction.
しかし、この方法によると、上述のとおり、脱
水縮合反応が主として起るため、グルコースの
β1→６結合から成る、いわゆるゲンチオビオー
スの生成が避けられず、それに起因する苦味が多
糖類に生ずる欠点がみられる。また、この方法で
は糖アルコールを約５〜20％の範囲の量で作用す
るものであるから、重縮合により得られる多糖類
の物性も狭い範囲のものに限られる。 However, as mentioned above, this method mainly involves the dehydration condensation reaction, so the production of so-called gentiobiose, which consists of β1→6 bonds of glucose, is unavoidable, resulting in a bitter taste in the polysaccharide. It will be done. Furthermore, since this method uses sugar alcohol in an amount ranging from about 5 to 20%, the physical properties of the polysaccharide obtained by polycondensation are also limited to a narrow range.
また、上記特公昭56−29512号の方法は、出発
物質としての澱粉又は澱粉部分加水分解物をポリ
カルボン酸と５重量％未満の水分の存在下に減圧
下で加熱することにより重合を行なわせるもので
あるが、この重合反応に際しては、澱粉ならびに
澱粉部分加水分解物はそれを構成する糖成分が全
て還元末端基を有するため、これが反応に関与
し、集合して樹脂状の巨大分子を形成するもので
ある。そして、このような重合反応上の現象は澱
粉の分解程度に関係なく起るので生成する重合体
もほぼ同一のものが得られ、従つて、物性も狭い
範囲のものに限られるという問題点がある。 Furthermore, in the method disclosed in Japanese Patent Publication No. 56-29512, polymerization is carried out by heating starch or starch partial hydrolyzate as a starting material under reduced pressure in the presence of polycarboxylic acid and less than 5% by weight of water. However, during this polymerization reaction, the sugar components that make up starch and starch partial hydrolysates all have reducing end groups, so these participate in the reaction and aggregate to form resin-like macromolecules. It is something to do. Since this phenomenon in the polymerization reaction occurs regardless of the degree of decomposition of starch, the resulting polymers are almost the same, and the physical properties are therefore limited to a narrow range. be.
加うるに、上記方法では遊離還元基の存在する
状態で反応が行なわれるので反応中の着色も著し
いという問題点がある。 In addition, the above method has the problem that the reaction is carried out in the presence of free reducing groups, resulting in significant coloration during the reaction.
発明が解決しようとする問題点
本発明は、上述したとおりの従来法による多糖
類の製造上の問題点に鑑みてなされたものであつ
て、出発原料として還元澱粉加水分解物を用いる
ことにより、該出発物質の糖構成に対応した糖組
成を有する広範囲な物性を具えた非消化性多糖類
を、実質上苦味や着色を伴なうことなく、短時間
で有利に製造し得る方法を提供することを目的と
する。Problems to be Solved by the Invention The present invention has been made in view of the problems in the production of polysaccharides by the conventional method as described above, and by using reduced starch hydrolyzate as a starting material, To provide a method for advantageously producing a non-digestible polysaccharide having a sugar composition corresponding to the sugar composition of the starting material and having a wide range of physical properties in a short time and without substantially causing bitterness or coloring. The purpose is to
以下本発明を詳しく説明する。 The present invention will be explained in detail below.
発明の構成
本発明の特徴は、還元澱粉加水分解物を無機酸
又は有機酸からなる触媒の存在下に無水条件下で
加熱することにより非消化性多糖類を得ることに
ある。Structure of the Invention The present invention is characterized in that a non-digestible polysaccharide is obtained by heating a reduced starch hydrolyzate under anhydrous conditions in the presence of a catalyst consisting of an inorganic or organic acid.
ここでいう“還元澱粉加水分解物”とは、澱粉
を酸糖化あるいは酵素糖化して得られる種々の
DE及び糖構成を有する澱粉加水分解物を水素添
加して得られる非還元性糖類の混合物を意味する
ものである。したがつて、該還元澱粉加水分解物
は広範囲な分解物を包含するものである。 The term “reduced starch hydrolyzate” here refers to various types of starch obtained by acid saccharification or enzymatic saccharification.
It refers to a mixture of non-reducing sugars obtained by hydrogenating a starch hydrolyzate having DE and sugar composition. Therefore, the reduced starch hydrolyzate includes a wide range of decomposition products.
問題点を解決するための手段
本発明において出発物質として用いる還元澱粉
加水分解物は上述のとおりその糖化により広範囲
なDE及び糖構成のものを包含しているが、その
使用上の選択に当つては、目的とする多糖類に要
求される物性、すなわち、食餌療法上の食品素材
として必要な物性に基き、それを基準として選択
する。Means for Solving the Problems As mentioned above, the reduced starch hydrolyzate used as a starting material includes a wide range of DE and sugar compositions due to its saccharification. is selected based on the physical properties required of the target polysaccharide, that is, the physical properties required as a dietary food material.
本発明で用いる還元澱粉加水分解物としては、
還元分枝デキストリン及び通称還元水アメと呼ば
れる、澱粉を酸や酵素で糖化したものを水素添加
したものを例示し得る。 The reduced starch hydrolyzate used in the present invention includes:
Examples include reduced branched dextrin and hydrogenated starch saccharified with acid or enzymes, commonly called reduced starch syrup.
また、本発明で触媒として用いる無機酸ならび
に有機酸は不揮発性酸であればよく、無機酸とし
てはリン酸が適当であり、その使用量は、還元澱
粉加水分解物の固形分に対して0.3〜0.5重量％程
度がよい。また、有機酸としてはカルボン酸によ
るエステル架橋を、多糖類製造のための反応上必
要とする場合には、クエン酸、フマール酸、酒石
酸、リンゴ酸等のポリカルボン酸が好ましく、そ
の使用量は上記固形分に対して５〜20重量％が適
当である。 In addition, the inorganic acid and organic acid used as a catalyst in the present invention may be any non-volatile acid, and phosphoric acid is suitable as the inorganic acid, and the amount used is 0.3 based on the solid content of the reduced starch hydrolyzate. ~0.5% by weight is preferable. In addition, as the organic acid, when ester crosslinking with carboxylic acid is required for the reaction for polysaccharide production, polycarboxylic acids such as citric acid, fumaric acid, tartaric acid, and malic acid are preferable, and the amount used is A suitable amount is 5 to 20% by weight based on the above solid content.
本発明を実施するに当つては、まず、目的とす
る多糖類に応じて出発物質としての還元澱粉加水
分解物を選択し、それを粉体状のまま、もしくは
液状にしたものに酸触媒を添加し、液状の場合に
は減圧下に濃縮して粉末化し、ついで上記粉体状
のもの又は粉末化したものをトレイもしくはロー
タリエバポレータに採取し、130℃まで減圧下に
徐々に加熱して、なお粉体状態にあることを確め
た後、さらに160℃〜180℃まで昇温し、約１〜３
時間保持する。このようにして得られる反応物は
粉状体であるため、反応容器から容易に取り出す
ことができる。 In carrying out the present invention, first, a reduced starch hydrolyzate is selected as a starting material depending on the target polysaccharide, and an acid catalyst is applied to the reduced starch hydrolyzate as a powder or in a liquid state. If it is liquid, it is concentrated under reduced pressure and powdered, and then the powdered or powdered material is collected in a tray or rotary evaporator, and gradually heated to 130 ° C. under reduced pressure. After confirming that it is in a powder state, the temperature is further increased to 160℃~180℃, and the temperature is increased to about 1~3℃.
Hold time. Since the reactant thus obtained is in powder form, it can be easily taken out from the reaction container.
なお、出発物質にDEの高い澱粉加水分解物を
水素添加した還元澱粉加水分解物を用いた場合に
は、溶融状態で反応を行なうことになるが、この
場合も上記と同様に操作し得る。 Note that when a reduced starch hydrolyzate obtained by hydrogenating a starch hydrolyzate with a high DE is used as the starting material, the reaction will be carried out in a molten state, and in this case, the same operation as above can be performed.
反応物はほとんど着色していないのでそのまま
製品となし得るが、脱酸の必要があれば水に再溶
解し、イオン交換樹脂などを用いて脱酸した後、
濃縮してシラツプとするか、乾燥粉末化して製品
とするとよい。 Since the reactant is hardly colored, it can be used as a product as it is, but if deacidification is necessary, it is redissolved in water, deoxidized using an ion exchange resin, etc.
It is best to concentrate it to make syrup or dry powder to make it into a product.
本発明により得られる多糖類は、還元澱粉加水
分解物を無水条件下で加熱することにより得られ
るものであつて、それを構成する非還元糖類のグ
ルコース残基が主として１→６結合で転移した各
種の重合度を有する非還元重合体の集合体から成
る。また、本発明により得られる多糖類では、非
還元重合体間の縮合反応が起らないため、出発物
質として用いた還元澱粉加水分解物の糖構成に対
応した非消化性多糖類となる。 The polysaccharide obtained by the present invention is obtained by heating reduced starch hydrolyzate under anhydrous conditions, and the glucose residues of the non-reducing saccharide constituting the polysaccharide are mainly transferred through 1→6 bonds. It consists of a collection of non-reduced polymers with various degrees of polymerization. Furthermore, in the polysaccharide obtained by the present invention, since no condensation reaction occurs between non-reduced polymers, the polysaccharide becomes a non-digestible polysaccharide corresponding to the sugar composition of the reduced starch hydrolyzate used as a starting material.
したがつて、本発明によると、前述したよう
に、上記還元澱粉加水分解を選択することによ
り、それに対応した糖構成を有する種々の物性を
具えた製品を得ることができる。 Therefore, according to the present invention, as described above, by selecting the above-mentioned reduced starch hydrolysis, it is possible to obtain products having a corresponding sugar composition and various physical properties.
さらに、本発明において用いる還元澱粉加水分
解物は、非還元糖類から構成されているため、還
元性糖類からなる澱粉糖に比べてはるかに熱安定
性が良好であり、したがつて、本発明では無水条
件下でも150〜250℃程度で加熱することができる
ので、短時間で目的多糖類を製造し得る利点も
る。 Furthermore, since the reduced starch hydrolyzate used in the present invention is composed of non-reducing saccharides, it has much better thermal stability than starch sugar composed of reducing saccharides. Since it can be heated at about 150 to 250°C even under anhydrous conditions, it has the advantage of producing the desired polysaccharide in a short time.
以下に実施例を示して本発明をさらに具体的に
説明する。 EXAMPLES The present invention will be explained in more detail with reference to Examples below.
実施例 １
DE22のα−アミラーゼによる澱粉加水分解物
を水素添加した還元澱粉加水分解物（水分30％）
145ｇにクエン酸５ｇを添加して溶解し、真空オ
ーブンにて100℃、760mmHgの減圧下で脱水乾燥
した。この乾燥物の10％溶液のPHは2.6であり、
糖組成は重量でG1：3.0％、G2：7.1％、G3：9.0
％、G4：6.7％、G5：7.2％、G6：23.1％、Gn＞
６：43.9％（Gnは非還元糖類の重合度を示す）
であつた。次いで、上記脱水乾燥物をロータリエ
バポレータに採取し、750mmHgの減圧下、シリコ
ンオイル浴中で重合反応を行なつた。回転数は
80r.p.mとした。Example 1 Reduced starch hydrolyzate (moisture 30%) obtained by hydrogenating starch hydrolyzate using α-amylase of DE22
5 g of citric acid was added to 145 g, dissolved, and dehydrated and dried in a vacuum oven at 100° C. under reduced pressure of 760 mmHg. The pH of a 10% solution of this dried product is 2.6,
Sugar composition by weight: G1: 3.0%, G2: 7.1%, G3: 9.0
%, G4: 6.7%, G5: 7.2%, G6: 23.1%, Gn＞
6: 43.9% (Gn indicates the degree of polymerization of non-reducing sugars)
It was hot. Next, the dehydrated product was collected in a rotary evaporator, and a polymerization reaction was carried out in a silicone oil bath under reduced pressure of 750 mmHg. The number of rotations is
It was set to 80r.pm.
初め130℃までは徐々に昇温したところ溶融状
態を呈した。引き続き170℃まで昇温してその状
態で１時間保持した。得られた反応物の糖組成は
重量でG1：3.0％、G2：6.2％、G3：5.5％、G4：
5.8％、G5：4.4％、Gn＞５：75.1％（Gnは非還
元糖類の重合度を示す）であつた。。この反応物
の10％溶液の着色度は430ｍμ、10mmセルで測定
した結果0.02であつた。また同液（PH5.0）につ
いてアミロ（１，４）グルコシダーゼ、アミロ
（１，４、１，６）グルコシダーゼ、アミロ（１，
４）デキストリナーゼの混合系からなる酵素を過
剰に加え、55℃、２時間糖化した結果の糖組成は
重量でグルコース：10.8％、G1：3.8％、G2：7.8
％、G3：6.9％、G4：4.9％、G5：3.9％、Gn＞
５：61.9％であつた。 Initially, when the temperature was gradually increased to 130℃, it became molten. Subsequently, the temperature was raised to 170°C and held at that state for 1 hour. The sugar composition of the obtained reaction product was: G1: 3.0%, G2: 6.2%, G3: 5.5%, G4:
5.8%, G5: 4.4%, and Gn>5: 75.1% (Gn indicates the degree of polymerization of non-reducing sugars). . The degree of coloration of a 10% solution of this reactant was 0.02 as measured with a 430 mμ, 10 mm cell. Regarding the same solution (PH5.0), amylo(1,4) glucosidase, amylo(1,4,1,6) glucosidase, amylo(1,
4) Excessive addition of an enzyme consisting of a mixed system of dextrinase and saccharification at 55°C for 2 hours resulted in a sugar composition by weight of glucose: 10.8%, G1: 3.8%, G2: 7.8
%, G3: 6.9%, G4: 4.9%, G5: 3.9%, Gn＞
5: 61.9%.
反応物を粉砕して苦味の全くない白色粉末を得
た。 The reaction product was ground to obtain a white powder with no bitter taste.
実施例 ２
DE35のα−アミラーゼによる澱粉加水分解物
を水素添加した還元澱粉加水分解物（水分30％）
145ｇに、リン酸0.3ｇを添加し、真空オーブンに
て100℃、760mmHgkの減圧下で脱水乾燥した。
このものの10％溶液のPHは2.6であり、糖組成は
重量でG1：9.9％、G2：9.8％、G3：11.4％、
G4：6.7％、G5：7.6％、G6：17.3％、Gn＞６：
37.3％であつた。Example 2 Reduced starch hydrolyzate (moisture 30%) obtained by hydrogenating starch hydrolyzate using α-amylase of DE35
0.3 g of phosphoric acid was added to 145 g, and the mixture was dehydrated and dried in a vacuum oven at 100° C. under reduced pressure of 760 mmHgk.
The pH of a 10% solution of this product is 2.6, and the sugar composition is G1: 9.9%, G2: 9.8%, G3: 11.4%, by weight.
G4: 6.7%, G5: 7.6%, G6: 17.3%, Gn>6:
It was 37.3%.
次いで、上記脱水乾燥物をロータリーエバポレ
ータに採取し、750mmHgの減圧下、シリコンオイ
ル浴中で170℃で重合反応を行なつた。１時間経
過後の反応物の糖組成は重量でG1：7.5％、G2：
9.5％、G3：10.6％、G4：7.6％、G5：6.9％、Gn
＞５：57.9％（Gnは非還元糖類の重合度を示す）
であつた。また、この反応物の10％溶液の着色度
は430ｍμ、10mmセルで測定した結果0.04であつ
た。 Next, the dehydrated product was collected in a rotary evaporator, and a polymerization reaction was carried out at 170° C. in a silicone oil bath under a reduced pressure of 750 mmHg. The sugar composition of the reaction product after 1 hour was G1: 7.5%, G2:
9.5%, G3: 10.6%, G4: 7.6%, G5: 6.9%, Gn
>5: 57.9% (Gn indicates the degree of polymerization of non-reducing sugars)
It was hot. The degree of coloration of a 10% solution of this reactant was 0.04 when measured with a 430 mμ, 10 mm cell.
同液（PH5.0）について実施例１と同様の酵素
系で55℃、２時間糖化した結果、糖組成は次の通
りであつた。 The same solution (PH5.0) was saccharified at 55°C for 2 hours using the same enzyme system as in Example 1, and the sugar composition was as follows.
グルコース：11.7％、G1：7.2％、G2：9.2％、
G3：9.5％、G4：6.3％、G5：5.5％、Gn＞５：
50.6％であつた。反応物を粉砕して苦味の全くな
い白色粉末を得た。 Glucose: 11.7%, G1: 7.2%, G2: 9.2%,
G3: 9.5%, G4: 6.3%, G5: 5.5%, Gn>5:
It was 50.6%. The reaction product was ground to obtain a white powder with no bitter taste.
実施例 ３
DE8の分枝デキストリンを水素添加して得た還
元分枝デキストリンを出発物質とした。この出発
物質100ｇ及びクエン酸20ｇに水を加えて完全に
溶解し、100℃、760mmHgの減圧下で脱水乾燥し
た。次いで、この脱水乾燥物をロータリーエバポ
レータに採取し、シリコンオイル浴中、170℃、
２時間反応を行なわせた。反応中間体は粉末状を
呈した。反応物は水中でやや膨潤するのみで不溶
性であた、酵素反応は全く受けなかつた。粉砕後
微黄色の粉末を得た。Example 3 A reduced branched dextrin obtained by hydrogenating DE8 branched dextrin was used as a starting material. Water was added to 100 g of this starting material and 20 g of citric acid to completely dissolve it, and the mixture was dehydrated and dried at 100° C. under reduced pressure of 760 mmHg. Next, this dehydrated dry product was collected in a rotary evaporator and heated at 170°C in a silicone oil bath.
The reaction was allowed to proceed for 2 hours. The reaction intermediate was in the form of a powder. The reactant swelled slightly in water, was insoluble, and did not undergo any enzymatic reaction. After grinding, a slightly yellow powder was obtained.
Claims (1)
らなる触媒の存在下に無水条件下で加熱すること
を特徴とする非消化性多糖類の製造法。 ２ 加熱を150℃乃至250℃の温度で約１〜３時間
行なう特許請求の範囲第１項記載の製造法。[Scope of Claims] 1. A method for producing a non-digestible polysaccharide, which comprises heating a reduced starch hydrolyzate under anhydrous conditions in the presence of a catalyst consisting of an inorganic or organic acid. 2. The manufacturing method according to claim 1, wherein heating is carried out at a temperature of 150°C to 250°C for about 1 to 3 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60230855A JPS6291501A (en) | 1985-10-16 | 1985-10-16 | Production of nondigestible polysaccharide from reduced starch hydrolyzate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60230855A JPS6291501A (en) | 1985-10-16 | 1985-10-16 | Production of nondigestible polysaccharide from reduced starch hydrolyzate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6291501A JPS6291501A (en) | 1987-04-27 |
| JPH0112761B2 true JPH0112761B2 (en) | 1989-03-02 |
Family
ID=16914353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60230855A Granted JPS6291501A (en) | 1985-10-16 | 1985-10-16 | Production of nondigestible polysaccharide from reduced starch hydrolyzate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6291501A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001516388A (en) * | 1997-03-19 | 2001-09-25 | カルター フード サイエンス インコーポレーテッド | Monosaccharide and disaccharide polymerization using low levels of mineral acids. |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0728694B2 (en) * | 1990-02-22 | 1995-04-05 | 松谷化学工業株式会社 | Food composition having intestinal regulating action |
| FR2688793B1 (en) | 1992-03-19 | 1994-06-03 | Roquette Freres | COMPOSITION OF HYPOCARIOGENIC SACCHARIDES SACCHARIDES, PROCESS FOR PREPARING THE SAME AND APPLICATION THEREOF. |
| FR2831541B1 (en) * | 2001-10-30 | 2005-08-19 | Roquette Freres | SOLUBLE HYDROGEN STARCH DERIVATIVES CONTAINING NON-DIGESTIBLE FOOD FIBERS |
| FR2842992B1 (en) * | 2002-08-05 | 2006-02-10 | Roquette Freres | METHOD FOR MANUFACTURING SNACKS LUBRICATED IN FATS AND ENRICHED IN FIBERS AND SNACKS THUS OBTAINED |
-
1985
- 1985-10-16 JP JP60230855A patent/JPS6291501A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001516388A (en) * | 1997-03-19 | 2001-09-25 | カルター フード サイエンス インコーポレーテッド | Monosaccharide and disaccharide polymerization using low levels of mineral acids. |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6291501A (en) | 1987-04-27 |
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