JP2913017B2 - Method for producing cyclodextrins from starch granules - Google Patents
Method for producing cyclodextrins from starch granulesInfo
- Publication number
- JP2913017B2 JP2913017B2 JP8097409A JP9740996A JP2913017B2 JP 2913017 B2 JP2913017 B2 JP 2913017B2 JP 8097409 A JP8097409 A JP 8097409A JP 9740996 A JP9740996 A JP 9740996A JP 2913017 B2 JP2913017 B2 JP 2913017B2
- Authority
- JP
- Japan
- Prior art keywords
- starch
- cds
- granules
- starch granules
- cgtase
- 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 - Lifetime
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Description
【０００１】[0001]
【発明が属する技術分野】本発明は、生澱粉粒及び／又
は損傷澱粉粒からのサイクロデキストリン類（以下、Ｃ
Ｄｓと略記することがある。）の製造方法に関する。よ
り詳細には、馬鈴薯澱粉、トウモロコシ澱粉、甘藷澱
粉、小麦澱粉、コメ澱粉、タピオカ澱粉、サゴ澱粉、ア
マランス澱粉などの澱粉粒を液化することなく用い、こ
の澱粉粒にサイクロデキストリン合成酵素（以下、ＣＧ
Ｔａｓｅと略記することがある。）を作用させてＣＤｓ
を生成させ、さらに生成したＣＤｓを連続的に反応系外
に取り出してＣＤｓを製造する方法に関する。The present invention relates to raw starch granules and / or raw starch granules.
Are cyclodextrins (hereinafter C) from damaged starch granules
It may be abbreviated as Ds. )). More specifically, starch granules such as potato starch, corn starch, sweet potato starch, wheat starch, rice starch, tapioca starch, sago starch, and amaranth starch are used without liquefaction. CG
It may be abbreviated as Tase. ) To act on CDs
And producing the CDs by continuously taking out the generated CDs out of the reaction system.
【０００２】[0002]
【従来の技術】澱粉からＣＤｓを製造する方法として
は、澱粉を水に懸濁させて澱粉乳を作り、この澱粉乳を
耐熱性α−アミラーゼなどの液化用酵素とともに澱粉糊
化温度以上の高温に加熱して糊化−液化した後に、ＣＧ
Ｔａｓｅを加える方法が古くから用いられている。しか
し、ＣＤｓの収率低下を防止するために、澱粉を糊化−
液化するときには、ＣＧＴａｓｅを液化用酵素として用
いるのが一般的である。2. Description of the Related Art As a method for producing CDs from starch, a starch milk is prepared by suspending starch in water, and this starch milk is mixed with a liquefying enzyme such as a heat-resistant α-amylase at a temperature higher than the starch gelatinization temperature. After heating to gelatinization-liquefaction, CG
The method of adding Tase has been used for a long time. However, in order to prevent a decrease in the yield of CDs, the starch is gelatinized.
In liquefaction, CGTase is generally used as a liquefaction enzyme.
【０００３】ＣＤｓを製造する方法としては、約１０％
（ｗ／ｖ）濃度の澱粉乳に液化用酵素として耐熱性α−
アミラーゼもしくはＣＧＴａｓｅを加え、高温に加熱し
て酵素を失活させながら糊化−液化した後に、ＣＤｓ生
産用のＣＧＴａｓｅを加えてＣＤｓを生産する方法が実
用化されている。[0003] As a method for producing CDs, about 10%
(W / v) starch milk at a concentration of heat-resistant α-
A method in which amylase or CGTase is added, gelatinization-liquefaction is performed while heating and inactivating the enzyme to deactivate the enzyme, and then CGTase for producing CDs is added to produce CDs has been put to practical use.
【０００４】また、澱粉粒が糊化する程度に加熱を抑
え、ＣＧＴａｓｅの失活を抑制することにより、再びＣ
ＧＴａｓｅを加えることなくＣＤｓを生産する方法も知
られている。[0004] Further, by suppressing the heating to the extent that the starch granules are gelatinized, and by suppressing the deactivation of CGTase,
A method for producing CDs without adding GTase is also known.
【０００５】これらＣＤｓの製造法においては、６、
７、８グルコース環のそれぞれα−、β−、γ−ＣＤの
他に、９グルコース環以上の大環状ＣＤｓ、さらにはこ
れらに糖質が付加した分岐ＣＤｓの他に単糖、二糖、オ
リゴ糖が生産される。In the production method of these CDs, 6,
In addition to the α-, β-, and γ-CDs of the 7 and 8 glucose rings, respectively, macrocyclic CDs having 9 or more glucose rings, and branched CDs having a saccharide added thereto, as well as monosaccharides, disaccharides, and oligosaccharides Sugar is produced.
【０００６】これらＣＤｓ等の糖質は、澱粉液化工程、
液化澱粉からのＣＤｓ製造工程、液体クロマトグラフィ
によるカラム分離、限外濾過膜等による膜分離などによ
る精製工程を経て製造される。[0006] The carbohydrates such as CDs are subjected to a starch liquefaction step,
It is produced through a purification process such as CDs production process from liquefied starch, column separation by liquid chromatography, membrane separation using an ultrafiltration membrane or the like.
【０００７】しかし、澱粉乳を糊化−液化してからＣＧ
Ｔａｓｅを作用させる従来の製造方法では、糊化−液化
のための澱粉糊化温度以上の高温への加熱操作、及びそ
れに続くＣＤｓ合成反応のための冷却操作を必要とす
る。この際、加熱及び冷却エネルギーの使用が、ＣＤｓ
の製造上不利となる。また、糊化−液化しながらＣＧＴ
ａｓｅを加える従来のＣＤｓ製造方法においても、高温
加熱操作のためのエネルギーが必要である。However, starch milk is gelatinized and liquefied before CG
The conventional production method using Tase requires a heating operation to a temperature higher than the starch gelatinization temperature for gelatinization-liquefaction, and a subsequent cooling operation for CDs synthesis reaction. At this time, the use of heating and cooling energy
Disadvantage in the production of In addition, CGT while gelatinizing and liquefying
The conventional method for producing CDs to which ase is added also requires energy for a high-temperature heating operation.
【０００８】ＣＧＴａｓｅにより製造されたＣＤｓを、
膜により未反応液澱粉糊化−液化液から分離する操作の
際、一般的には限外濾過膜を用いるが、糊化−液化した
澱粉液が高粘度であるため、圧力をかけて膜分離を行う
必要があり、しかも透過流束が上がらず膜が目詰まりし
やすいなどの問題がある。[0008] CDs manufactured by CGTase are
In the operation of separating the unreacted liquid starch from the liquefied liquid using a membrane, an ultrafiltration membrane is generally used, but since the gelatinized-liquefied starch liquid has a high viscosity, the membrane is separated by applying pressure. In addition, there is a problem that the permeation flux does not increase and the membrane is easily clogged.
【０００９】また、糊化−液化した澱粉液は高粘度であ
ることなどの製造工程における操作性及び反応収率の問
題から、従来法では反応液中の澱粉濃度は重量濃度にし
て約１０％程度までしか上昇させることができない。In addition, the starch concentration in the reaction solution is about 10% by weight in the conventional method due to problems in operability and reaction yield in the production process such as the gelatinized and liquefied starch solution having a high viscosity. It can only be raised to a degree.
【００１０】最近、ＣＤｓを廉価で製造する必要性が増
加し、安価なＣＤｓを製造する方法の開発が強く求めら
れてきた。Recently, the need to produce CDs at low cost has increased, and there has been a strong demand for the development of a method for producing inexpensive CDs.
【００１１】[0011]
【発明が解決しようとする課題】本発明は、このような
要求を満たすＣＤｓの製造方法として、エネルギー消費
を抑え、液化せずに直接、澱粉粒にＣＧＴａｓｅを作用
させ、ＣＤｓを効率的に製造する方法を提供するもので
ある。SUMMARY OF THE INVENTION The present invention provides a method for producing CDs that satisfies such a demand by suppressing energy consumption and allowing CGTase to act directly on starch granules without liquefaction to efficiently produce CDs. It provides a way to:
【００１２】[0012]
【課題を解決するための手段】本発明は、生澱粉粒及び
／又は損傷澱粉粒を液化することなく、サイクロデキス
トリン合成酵素を作用させることを特徴とするＣＤｓの
製造方法に関する。SUMMARY OF THE INVENTION The present invention provides raw starch granules and
The present invention relates to a method for producing CDs, wherein a cyclodextrin synthase is allowed to act without liquefying damaged starch granules .
【００１３】[0013]
【発明の実施の形態】本発明によれば、澱粉粒を液化す
ることなく、サイクロデキストリン合成酵素を作用させ
てＣＤｓを製造することができる。ここで、澱粉粒は固
体のものであればよく、生澱粉粒や物理的外力により損
傷を受けたもの等を用いることができる。本発明の方法
は、基質が固体、生成物が液体であるので、分離が容易
であり、ＣＤｓを連続的に反応系外に取り出し、効率よ
く製造することができる。本発明の方法では、糊化−液
化することなく澱粉粒に直接酵素を作用させてＣＤｓを
製造することができるので、従来の方法よりも効率よく
ＣＤｓを製造することができる。According to the present invention, CDs can be produced by allowing cyclodextrin synthase to act without liquefying starch granules. Here, the starch granules may be solid ones, such as raw starch granules or those damaged by physical external force . According to the method of the present invention, since the substrate is a solid and the product is a liquid, the separation is easy, and CDs can be continuously taken out of the reaction system and efficiently produced. In the method of the present invention, CDs can be produced by directly applying an enzyme to starch granules without gelatinization-liquefaction, and thus CDs can be produced more efficiently than conventional methods.
【００１４】以下、本発明について詳しく説明する。本
発明で用いる基質である澱粉としては、馬鈴薯澱粉、ト
ウモロコシ澱粉、甘藷澱粉、小麦澱粉、コメ澱粉、タピ
オカ澱粉、サゴ澱粉、アマランサス澱粉などの生澱粉粒
や物理的処理した損傷澱粉粒が用いられる。損傷澱粉粒
は、粉砕、磨砕等の圧力、せん断力を伴う物理的処理に
より得られる。これら澱粉粒は、２種類以上を組み合わ
せて用いることができる。さらに、本発明によれば、最
大５０重量％程度、通常は１０〜３０重量％用いて反応
を行うことができる。Hereinafter, the present invention will be described in detail. The starch which is a substrate used in the present invention includes raw starch granules such as potato starch , corn starch, sweet potato starch, wheat starch, rice starch, tapioca starch, sago starch, and amaranth starch.
Or physically treated damaged starch granules are used. Damaged starch granules are subjected to physical treatment involving pressure and shear force such as grinding and grinding.
Is obtained . These starch granules can be used in combination of two or more kinds. Further, according to the present invention, the reaction can be carried out using a maximum of about 50% by weight, usually 10 to 30% by weight.
【００１５】次に、本発明で用いることのできるＣＧＴ
ａｓｅとしては各種由来のものがあり、例えばバチルス
・マセランス由来のＣＧＴａｓｅがあげられる。本酵素
の他にも、澱粉粒分解性（もしくは生澱粉分解性）を有
するＣＧＴａｓｅであれば、本発明に使用することがで
きる。Next, CGT which can be used in the present invention
Examples of the ase include those of various origins, for example, CGTase derived from Bacillus macerans. In addition to the present enzyme, any CGTase having starch granule degradability (or raw starch degradability) can be used in the present invention.
【００１６】固体基質である澱粉粒にＣＧＴａｓｅを作
用させる場合、ＣＧＴａｓｅはグラムあたり５〜５０Ｔ
ＨＵ（単位）用いる。また、この反応はｐＨ５〜１０．
５、好ましくは６〜８にて、４０〜６５℃、好ましくは
５０〜６０℃で６〜４８時間程度行う。When CGTase is allowed to act on starch granules as a solid substrate, CGTase is 5 to 50 T / gram.
Use HU (unit). This reaction was carried out at pH 5-10.
5, preferably at 6 to 8, at 40 to 65C, preferably at 50 to 60C for about 6 to 48 hours.
【００１７】固体基質にＣＧＴａｓｅを作用させると、
ＣＤｓは反応溶液に移るので、反応溶液を取り出し、膜
処理により酵素と生成物を分離し、酵素を循環させれ
ば、連続的な生産が可能となる。また、膜におけるＣＤ
ｓなどの糖質の分離操作においても、反応基質である澱
粉が固体のままであるので、澱粉乳の液部の粘度上昇が
少ないという操作上の利点もある。When CGTase is allowed to act on a solid substrate,
Since CDs are transferred to the reaction solution, continuous production is possible by removing the reaction solution, separating the enzyme and product by membrane treatment, and circulating the enzyme. CD in the film
Also in the separation operation of saccharides such as s, since the starch as a reaction substrate remains in a solid state, there is also an operational advantage that the increase in viscosity of the liquid part of starch milk is small.
【００１８】さらに、糊化−液化による高分子デキスト
リンの生成がなく、未反応澱粉は固体のまま残ることか
ら、本発明の方法は膜の目詰まりの軽減、洗浄操作の軽
減などの利点も有している。Furthermore, since high-molecular dextrin is not produced by gelatinization-liquefaction and unreacted starch remains as a solid, the method of the present invention has advantages such as reduction of membrane clogging and reduction of washing operation. doing.
【００１９】未反応の澱粉粒は、糊化−液化されていな
いので、そのまま或いは保存後、再び反応基質として用
いることができる。Since unreacted starch granules are not gelatinized and liquefied, they can be used again as a reaction substrate as it is or after storage.
【００２０】本発明における連続的なＣＤｓの製造工程
においては、従来必須であった液化工程を省略すること
ができる。すなわち、澱粉粒を液化することなくそのま
まＣＧＴａｓｅを作用させ、ＣＤｓを生産させ、限外濾
過膜等の膜による反応生成物の分離操作、逆浸透膜によ
る反応生成物の濃縮・晶析操作を経て最終製品を得るこ
とができる。In the continuous production process of CDs in the present invention, the liquefaction process which has been conventionally required can be omitted. That is, CGTase is allowed to act as it is without liquefaction of the starch granules, CDs are produced, the reaction product is separated by a membrane such as an ultrafiltration membrane, and the reaction product is concentrated and crystallized by a reverse osmosis membrane. You can get the final product.
【００２１】また、本発明における連続的なＣＤｓの製
造工程においては、限外濾過膜よりも孔径が大きい精密
濾過膜や粒子濾過膜等を、ＣＧＴａｓｅ反応容器の直後
に設備することにより、澱粉粒の除去及び再利用が可能
になるのみならず、引き続く限外濾過膜による分離操作
において、膜の目詰まりの軽減等、製造工程の操作性を
効率的に向上させることが可能である。In the continuous production process of CDs according to the present invention, a microfiltration membrane or a particle filtration membrane having a pore size larger than that of an ultrafiltration membrane is installed immediately after a CGTase reaction vessel, so that starch granules can be obtained. Not only can be removed and reused, but also in the subsequent separation operation using an ultrafiltration membrane, the operability of the production process can be efficiently improved, such as reduction of clogging of the membrane.
【００２２】本発明においては澱粉を糊化−液化する操
作を省くことができることから、従来約１０重量％の濃
度以下でしか用いられなかった澱粉を、約３０重量％以
上でも用いることができる。つまり、連続的に大量のＣ
Ｄｓを製造すること可能となり、実用上の価値が大き
い。In the present invention, since the operation of gelatinizing and liquefying starch can be omitted, starch which has been conventionally used only at a concentration of about 10% by weight or less can be used at about 30% by weight or more. That is, a large amount of C continuously
Ds can be manufactured, which is of great practical value.
【００２３】反応系にＣＤｓの生産を促進する物質、例
えば澱粉鎖に特定の立体構造を形成させて螺旋等を形成
させると言われるエタノール、ＳＤＳ（ドデシル硫酸ナ
トリウム）、脂肪酸等の物質の他に、澱粉の溶解性を向
上させると言われるＤＭＳＯ（ジメチルスルホキシド）
等の物質、ｐＨを調整するための酸性物質もしくは塩基
性物質を加えてもよい。In addition to substances that promote the production of CDs in the reaction system, for example, substances such as ethanol, SDS (sodium dodecyl sulfate) and fatty acids, which are said to form a specific steric structure in the starch chain to form a helix or the like. DMSO (dimethyl sulfoxide) is said to improve the solubility of starch
Or an acidic substance or a basic substance for adjusting pH.
【００２４】[0024]
【実施例】以下、本発明を実施例を用いて詳述するが、
本発明はこれらに限定されるものではない。Hereinafter, the present invention will be described in detail with reference to Examples.
The present invention is not limited to these.
【００２５】実施例１ 市販馬鈴薯澱粉１０．０ｇ（最終濃度１０．０重量％）
をｐＨ５．５のリン酸緩衝液（NaH2PO4-Na2HPO4)８９．
０ｇに懸濁させ、５０℃に保ち、攪拌しつつバチルス・
マセランス由来のＣＧＴａｓｅ液１００μＬ（酵素単位
６THU/g 澱粉）を添加して反応を開始した。その結果、
図１に示すように、ＣＤｓの生産量は経時的に増加し、
最大で約２４％の収率でＣＤｓが得られた。Example 1 10.0 g of commercially available potato starch (final concentration 10.0% by weight)
PH 5.5 phosphate buffer (NaH 2 PO 4 —Na 2 HPO 4 ) 89.
0 g, maintained at 50 ° C, and stirred while
The reaction was started by adding 100 μL of CGTase solution derived from macerans (enzyme unit: 6 THU / g starch). as a result,
As shown in FIG. 1, the production of CDs increases over time,
CDs were obtained with a maximum yield of about 24%.
【００２６】実施例２ 市販馬鈴薯澱粉の最終重量濃度、該ＣＧＴａｓｅ液添加
量、反応時間が異なる以外は実施例１と同様にして市販
馬鈴薯澱粉濃度２０．０ｇ（最終濃度２０．０重量％）
または３０．０ｇ（最終濃度３０．０重量％）にＣＧＴ
ａｓｅ液の酵素単位６THU/g 澱粉（それぞれ２００μ
Ｌ、３００μＬ）を加えて反応を開始したところ、図２
に示すように、１２０時間後に、約１８％または約１６
％の収率でＣＤｓが得られた。Example 2 A commercial potato starch concentration of 20.0 g (final concentration 20.0% by weight) was carried out in the same manner as in Example 1 except that the final weight concentration of the commercially available potato starch, the amount of the CGTase solution added, and the reaction time were different.
Or CGT to 30.0 g (final concentration 30.0% by weight)
Enzyme unit 6 THU / g starch (200 μl each)
L, 300 μL) was added to start the reaction.
After 120 hours, about 18% or about 16%
CDs were obtained in a% yield.
【００２７】実施例３ 馬鈴薯澱粉は市販馬鈴薯澱粉を１時間自動乳鉢で磨砕し
たものを用いたこと、攪拌をしなかったこと、及び反応
時間を２４時間としたこと以外は実施例１と同様にして
実施したところ、図３に示すように、磨砕澱粉粒を用い
ることで、攪拌しなくてもＣＤｓが約２３％の収率で得
られた。Example 3 The same as Example 1 except that potato starch obtained by grinding commercially available potato starch in an automatic mortar for 1 hour was used, stirring was not performed, and the reaction time was set to 24 hours. As shown in FIG. 3, CDs were obtained at a yield of about 23% by using the ground starch granules without stirring.
【００２８】実施例４ 反応液のｐＨを変えたこと以外は実施例１と同様にして
実施したところ、図４に示すように、ｐＨを調整する物
質（この場合は酸性物質としてNaH2PO4 、塩基性物質と
してNa2HPO4)の量を加減することにより、ｐＨ８におい
てＣＤｓが約３０％の収率で得られた。なお、通常のＣ
ＧＴａｓｅ安定領域以外でも、酵素は澱粉粒に吸着され
ることにより安定化され、例えばｐＨ１０でもＣＤｓの
収率は２０％であり、反応が進行することが示された。Example 4 The procedure of Example 1 was repeated except that the pH of the reaction solution was changed. As shown in FIG. 4, a substance for adjusting the pH (in this case, NaH 2 PO 4 was used as an acidic substance) By adjusting the amount of Na 2 HPO 4 ) as a basic substance, CDs were obtained at pH 8 with a yield of about 30%. In addition, normal C
Outside the GTase stable region, the enzyme was stabilized by being adsorbed to the starch granules. For example, even at pH 10, the yield of CDs was 20%, indicating that the reaction proceeded.
【００２９】[0029]
【発明の効果】本発明の方法では、澱粉粒を液化するこ
となく、澱粉粒分解性を有するＣＧＴａｓｅで分解し、
高濃度の澱粉粒からＣＤｓを得ることができる。また、
本発明の方法では、澱粉粒を糊化−液化するための加熱
操作を、完全に或いは一部省略できるので、ＣＤｓを極
めて効率的に製造することができる。According to the method of the present invention, starch granules are decomposed with CGTase having starch-degrading property without liquefaction,
CDs can be obtained from highly concentrated starch granules. Also,
In the method of the present invention, the heating operation for gelatinizing and liquefying the starch granules can be completely or partially omitted, so that CDs can be produced extremely efficiently.
【図１】 馬鈴薯澱粉（重量濃度１０％）に、攪拌条件
下、バチルス・マセランス由来のＣＧＴａｓｅを澱粉１
グラムあたり６単位量作用させたときのＣＤｓの生成量
の経時変化を示すものである。FIG. 1 shows that CGTase derived from Bacillus macerans is added to potato starch (weight concentration 10%) under stirring conditions.
FIG. 4 shows the change over time in the amount of CDs produced when 6 units are applied per gram.
【図２】 重量濃度５、１０、２０、３０％の馬鈴薯澱
粉に、攪拌条件下、バチルス・マセランス由来のＣＧＴ
ａｓｅを澱粉１グラムあたり６単位量作用させたときの
１２０時間後のＣＤｓの生成量を示したものである。FIG. 2: CGT derived from Bacillus macerans on potato starch having a weight concentration of 5, 10, 20, and 30% under stirring conditions.
1 shows the amount of CDs produced after 120 hours when ase was allowed to act in an amount of 6 units per gram of starch.
【図３】 磨砕処理或いは未処理、それぞれの馬鈴薯澱
粉（重量濃度１０％）に、静置条件下、バチルス・マセ
ランス由来のＣＧＴａｓｅを澱粉１グラムあたり６単位
量作用させたときのＣＤｓの生成量を示したものであ
る。FIG. 3 shows the generation of CDs when CGTase derived from Bacillus macerans was allowed to act on each of potato starch (weight concentration 10%), which had been ground or untreated, in a static condition, in an amount of 6 units per gram of starch. It shows the amount.
【図４】 異なるｐＨ条件下において、馬鈴薯澱粉（重
量濃度１０％）に、攪拌条件下、バチルス・マセランス
由来のＣＧＴａｓｅを澱粉１グラムあたり６単位量作用
させたときのＣＤｓの生成量を示したものである。FIG. 4 shows the amount of CDs produced when CGTase derived from Bacillus macerans was allowed to act on a potato starch (10% by weight) under different pH conditions in an amount of 6 units per gram of starch under stirring conditions. Things.
Claims (3)
ることなく、サイクロデキストリン合成酵素を作用させ
ることを特徴とするサイクロデキストリン類の製造方
法。1. A process for producing cyclodextrins, wherein a cyclodextrin synthase is allowed to act without liquefying raw starch granules and / or damaged starch granules .
粉、甘藷澱粉、小麦澱粉、コメ澱粉、タピオカ澱粉、サ
ゴ澱粉及びアマランサス澱粉のいずれかである請求項１
記載の方法。2. The starch according to claim 1, wherein the starch is any one of potato starch, corn starch, sweet potato starch, wheat starch, rice starch, tapioca starch, sago starch and amaranth starch.
The described method.
的に反応系外に取り出してサイクロデキストリン類の製
造を行う請求項１記載の方法。3. The method according to claim 1, wherein the cyclodextrins produced are continuously taken out of the reaction system to produce cyclodextrins.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8097409A JP2913017B2 (en) | 1996-03-28 | 1996-03-28 | Method for producing cyclodextrins from starch granules |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8097409A JP2913017B2 (en) | 1996-03-28 | 1996-03-28 | Method for producing cyclodextrins from starch granules |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09262091A JPH09262091A (en) | 1997-10-07 |
| JP2913017B2 true JP2913017B2 (en) | 1999-06-28 |
Family
ID=14191704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8097409A Expired - Lifetime JP2913017B2 (en) | 1996-03-28 | 1996-03-28 | Method for producing cyclodextrins from starch granules |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2913017B2 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2782077B2 (en) * | 1989-02-28 | 1998-07-30 | 王子コーンスターチ株式会社 | Method for producing cyclodextrin |
-
1996
- 1996-03-28 JP JP8097409A patent/JP2913017B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09262091A (en) | 1997-10-07 |
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