JPH04187695A - Production of soybean oligosaccharide - Google Patents
Production of soybean oligosaccharideInfo
- Publication number
- JPH04187695A JPH04187695A JP2319531A JP31953190A JPH04187695A JP H04187695 A JPH04187695 A JP H04187695A JP 2319531 A JP2319531 A JP 2319531A JP 31953190 A JP31953190 A JP 31953190A JP H04187695 A JPH04187695 A JP H04187695A
- Authority
- JP
- Japan
- Prior art keywords
- soybean
- phosphoric acid
- solution
- protein
- oligosaccharide
- 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.)
- Granted
Links
- 244000068988 Glycine max Species 0.000 title claims abstract description 38
- 235000010469 Glycine max Nutrition 0.000 title claims abstract description 38
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 22
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000010438 heat treatment Methods 0.000 claims abstract description 15
- 239000005862 Whey Substances 0.000 claims abstract description 13
- 102000007544 Whey Proteins Human genes 0.000 claims abstract description 13
- 108010046377 Whey Proteins Proteins 0.000 claims abstract description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 12
- 239000002244 precipitate Substances 0.000 claims abstract description 9
- 102000004169 proteins and genes Human genes 0.000 abstract description 7
- 108090000623 proteins and genes Proteins 0.000 abstract description 7
- 241000186000 Bifidobacterium Species 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 235000003599 food sweetener Nutrition 0.000 abstract description 2
- 235000013336 milk Nutrition 0.000 abstract description 2
- 239000008267 milk Substances 0.000 abstract description 2
- 210000004080 milk Anatomy 0.000 abstract description 2
- 239000003765 sweetening agent Substances 0.000 abstract description 2
- 244000046052 Phaseolus vulgaris Species 0.000 abstract 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 abstract 1
- 230000002062 proliferating effect Effects 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 150000002772 monosaccharides Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 235000018102 proteins Nutrition 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 108010073771 Soybean Proteins Proteins 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 235000019710 soybean protein Nutrition 0.000 description 3
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BYMMIQCVDHHYGG-UHFFFAOYSA-N Cl.OP(O)(O)=O Chemical compound Cl.OP(O)(O)=O BYMMIQCVDHHYGG-UHFFFAOYSA-N 0.000 description 1
- 235000019750 Crude protein Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UQZIYBXSHAGNOE-USOSMYMVSA-N Stachyose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO[C@@H]2[C@@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O2)O1 UQZIYBXSHAGNOE-USOSMYMVSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 235000013322 soy milk Nutrition 0.000 description 1
- UQZIYBXSHAGNOE-XNSRJBNMSA-N stachyose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@@H]3[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O3)O)O2)O)O1 UQZIYBXSHAGNOE-XNSRJBNMSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
Landscapes
- Dairy Products (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
本発明は大豆ホエーがらオリゴ糖を分離精製して大豆オ
リゴ糖を製造する方法に関する。The present invention relates to a method for producing soybean oligosaccharides by separating and refining oligosaccharides from soybean whey.
大豆又は脱脂大豆から水抽出してオカラを除去した残り
の豆乳からさらに大豆蛋白を分離すると大豆ホエーが得
られる。
大豆ホエーから大豆オリゴ糖を製造する方法として例え
ば特公平１−４５３５４には、大豆ホエーを塩化カルシ
ウム存在下に水酸化カルシウムで中和するとともに加熱
し、生じた沈澱物を除去し膜分離して大豆オリゴ糖を得
る方法が開示されている。
又、特開昭６２−１５５０８２には、脱脂大豆をアルコ
ール溶液で抽出して大豆オリゴ糖を含む物質を得る方法
が開示されている。
しかし、いずれの方法も大豆オリゴ糖の精製が充分でな
い欠点を有している。Soybean whey is obtained by further separating soybean protein from the remaining soymilk that has been extracted with water from soybeans or defatted soybeans to remove okara. For example, Japanese Patent Publication No. 1-45354 describes a method for producing soybean oligosaccharides from soybean whey by neutralizing soybean whey with calcium hydroxide in the presence of calcium chloride, heating it, removing the resulting precipitate, and separating it through a membrane. A method for obtaining soybean oligosaccharides is disclosed. Further, JP-A-62-155082 discloses a method of extracting defatted soybeans with an alcohol solution to obtain a substance containing soybean oligosaccharides. However, both methods have the disadvantage that soybean oligosaccharides cannot be sufficiently purified.
本発明者等は大豆ホエー中の大豆蛋白を除去する為に加
熱処理を検討した。確かに、加熱により変性して不溶化
する成分は遠心分離等で除去できるが未変性成分は除去
が困難であったり、経時的に濁りが生じたりする。そこ
で、たんに加熱を強くすると糖が分解したり、又膜によ
り強制的に濁りを除去しようとすると時間がかかったり
膜の目詰まりが生ずる等の問題がある。
本発明者等は糖の分解が極めて少なく蛋白質を効率的に
除去できる実用的なオリゴ糖のｎ製を目的として研究を
進めた。The present inventors investigated heat treatment to remove soybean protein from soybean whey. It is true that components that are denatured and insolubilized by heating can be removed by centrifugation or the like, but undenatured components are difficult to remove or become cloudy over time. Therefore, if the heating is too strong, the sugar will decompose, and if the turbidity is forcibly removed using a membrane, it will take time and the membrane will become clogged. The present inventors have carried out research with the aim of producing a practical oligosaccharide that can efficiently remove proteins with extremely little sugar decomposition.
本発明者等は前記目的を達成すべく鋭意研究の結果、大
豆ホエーを加熱した後リン酸でｐＨ３以下に調整して生
じる沈澱を除去すれば目的とする大豆オリゴ糖が高収率
で得られる知見を得て本発明を完成するに到った。
即ち、本発明は、大豆ホエー溶液を７０〜１１０℃にて
加熱処理し、リン酸を用いてｐＨ３以下に調整し、生じ
た沈澱物を除去することを特徴とする大豆オリゴ糖の製
造法である。
本発明に用いる大豆ホエーは（ａ）大豆又は脱脂大豆か
ら得られた豆乳に酸又はアルカリ±Ｉｌｌを加え蛋白を
凝固させて除去した水溶液もしくはこの濃縮液でも、（
ｂｌ大豆又は脱脂大豆から５０〜８０％のアルコール溶
液を用いて抽出した水溶液でもよい。
本発明において、７０℃〜１１０℃（好ましくは８０〜
１００℃）で５〜３０分間加熱することが重要である。
加熱が充分でないと次のリン酸処理と組み合わせても変
性蛋白質の凝集が不十分で蛋白質の除去は充分でなく、
あまり加熱しすぎるとオリゴ糖が単糖にまで分解されて
オリゴ糖の含有比率が低下しビフィズス菌以外の菌でも
資化できるようになりその有効性が低下するので好まし
くない。
本発明において、加熱処理後、リン酸を用いてｐＨ３以
下に調整することが重要なポイントである。
塩酸ではｐＨ１，５以下にしないと沈澱除去効果がない
がリン酸ならｐＨ３Ｊ２１下で効果がある。
その理由は不明である。
即ち、リン酸を用いて且つｐＨ３以下となすことにより
前記加熱処理との組み合わせで生じる蛋白質の沈澱なら
公知の手段で分離でき、残る水溶液は濁りのない精製度
の高いオリゴ糖液とすることができる。
生しる沈澱の分離手段は遠心分離、濾過等公知の手段を
利用することができる。尚、濾過は膜濾過よりケイソウ
土濾過のほうが速く実用的である。
このようにして得られる清澄液はそのまま濃縮したり乾
燥して大豆オリゴ糖とすることもできるが、好ましくは
多孔性有機合成吸着剤、活性炭等で処理したり更にイオ
ン交換樹脂、電気透析処理又は逆浸透膜等による透析処
理等が適当である。As a result of intensive research to achieve the above object, the present inventors have found that the desired soybean oligosaccharide can be obtained in high yield by heating soybean whey, adjusting the pH to 3 or less with phosphoric acid, and removing the resulting precipitate. Based on this knowledge, we have completed the present invention. That is, the present invention is a method for producing soybean oligosaccharides, which is characterized by heat-treating a soybean whey solution at 70 to 110°C, adjusting the pH to 3 or less using phosphoric acid, and removing the resulting precipitate. be. The soybean whey used in the present invention may be (a) an aqueous solution obtained by adding acid or alkali ±Ill to soybean milk obtained from soybeans or defatted soybeans to coagulate and remove proteins, or a concentrated solution thereof (
An aqueous solution extracted from bl soybeans or defatted soybeans using a 50-80% alcohol solution may also be used. In the present invention, 70°C to 110°C (preferably 80°C to 110°C)
It is important to heat at 100° C. for 5 to 30 minutes. If the heating is not sufficient, the denatured protein will not aggregate sufficiently and the protein will not be removed even if it is combined with the next phosphoric acid treatment.
Excessive heating is undesirable because oligosaccharides are decomposed into monosaccharides, the content ratio of oligosaccharides decreases, and bacteria other than Bifidobacteria can assimilate them, reducing their effectiveness. In the present invention, it is important to adjust the pH to 3 or less using phosphoric acid after the heat treatment. Hydrochloric acid has no effect on removing the precipitate unless the pH is below 1.5, but phosphoric acid is effective at pH 3J21. The reason is unknown. That is, by using phosphoric acid and adjusting the pH to 3 or less, the protein precipitate that occurs in combination with the heat treatment can be separated by known means, and the remaining aqueous solution can be made into a highly purified oligosaccharide solution without turbidity. can. As a means for separating the resulting precipitate, known means such as centrifugation and filtration can be used. Note that diatomaceous earth filtration is faster and more practical than membrane filtration. The clarified liquid obtained in this way can be directly concentrated or dried to obtain soybean oligosaccharides, but it is preferably treated with a porous organic synthetic adsorbent, activated carbon, etc., or further treated with an ion exchange resin, electrodialysis treatment, or Dialysis treatment using a reverse osmosis membrane or the like is appropriate.
以下実施例により本発明の実施態様を説明する。
実施例１
分離大豆蛋白製造工程で得られた大豆ホエーを９０°Ｃ
で１０分間加熱し、冷却後リン酸を加えｐＨを３に調整
した。
生じたコロイド状物質を遠心分Ｍ（２５００ＲＰＭＸ１
５分）して清澄液を得た。
この清澄液を多孔性有機合成吸着剤（ダイヤイオンＨＰ
−２０、三菱化成■製）に通し、更にイオン交換樹脂（
レバチット、Ｂａｙｅｒ社製）に通した後、減圧・濃縮
し、次いで活性炭処理して大豆オリゴ糖濃縮物を得た。
濃縮物の成分分析値は：水分４２％、粗蛋白０゜０１％
、灰分０．０３％、糖質５８％であった。
糖質の内訳は３単糖以上４０％、シュークロース５５％
、単糖類５％であった。
実施例２
実施例１と同様にしてリン酸を用いてｐ Ｈ３ニ調節す
る処理工程を、リン酸又は塩酸とし、種々のｐＨにした
後、遠心分離して得られる液の濁り具合を見た。
遠心分離（３０００ＲＰＭ ｘ １０分）後の濁りを次
表に示す。
又、このときの糖類の加水分解の程度を合わせ示す。
表
ｐＨリン酸 塩酸 ３単糖以上
１．５ − −３２ ％２−’Ｏ−
＋ ４０．０ ％
２・ ５ − 十十
３．０ ＝ ＋＋４０．５ ％３・
５ ＋ 十十
４．０ ＋十＋＋ ４０．６ ％−清澄
十 若干濁り
＋十 濁り
３単糖以上は糖類組成中の３単糖以上の糖類（ラフィノ
ース、スタキオース）の割合を示す。
以上よりｐＨ１，５以下では糖の加水分解が起こり、リ
ン酸ではｐＨ３，５以上で濁りが生じ、塩酸ではｐＨ２
以上で濁りが生じた。
実施例３
大豆ホエーの加熱処理温度を変える他は実施例１と同様
にしてオリゴ糖溶液を得た。
加熱温度と得られたオリゴ糖溶液の濁り及び糖の分解を
次表に示す。
表
加熱温度 濁り 加水分解
６０℃ 十 −
８０℃ −
１００°Ｃ−
１２０℃ −〒
６０℃以下では濁りが生し、１２０以上では糖類の分解
が見られ、３単糖以上の割合は３５％に減少した。Embodiments of the present invention will be described below with reference to Examples. Example 1 Soybean whey obtained in the isolated soybean protein production process was heated to 90°C.
The mixture was heated for 10 minutes, and after cooling, phosphoric acid was added to adjust the pH to 3. The resulting colloidal substance was centrifuged with M (2500RPMX1
5 minutes) to obtain a clear liquid. This clear liquid is used as a porous organic synthetic adsorbent (Diaion HP).
-20, made by Mitsubishi Kasei), and then passed through an ion exchange resin (
After passing through Levacit (manufactured by Bayer), it was concentrated under reduced pressure, and then treated with activated carbon to obtain a soybean oligosaccharide concentrate. Component analysis of the concentrate: 42% water, 0.01% crude protein.
, ash content was 0.03%, and carbohydrate content was 58%. The breakdown of carbohydrates is 40% 3 or more monosaccharides, 55% sucrose.
, 5% monosaccharides. Example 2 In the same manner as in Example 1, the pH was adjusted to 3 using phosphoric acid or hydrochloric acid. . The turbidity after centrifugation (3000 RPM x 10 minutes) is shown in the following table. The degree of hydrolysis of sugars at this time is also shown. Table pH Phosphoric acid Hydrochloric acid 3 monosaccharides or more 1.5 - -32 %2-'O-
+ 40.0% 2・5 − 113.0 = ++40.5%3・
5 + 10 4.0 + 10++ 40.6 % - Clear 10 Slightly cloudy + 10 Cloudy 3 or more monosaccharides indicates the proportion of saccharides with 3 or more monosaccharides (raffinose, stachyose) in the saccharide composition. From the above, hydrolysis of sugar occurs at pH 1.5 or lower, turbidity occurs at pH 3.5 or higher with phosphoric acid, and turbidity occurs at pH 2 or higher with hydrochloric acid.
This caused turbidity. Example 3 An oligosaccharide solution was obtained in the same manner as in Example 1, except that the heat treatment temperature of soybean whey was changed. The heating temperature, turbidity of the obtained oligosaccharide solution, and sugar decomposition are shown in the following table. Surface heating temperature Turbidity Hydrolysis 60°C 10 - 80°C - 100°C - 120°C - Below 60°C, turbidity occurs, and above 120°C, decomposition of sugars is observed, and the proportion of 3 or more monosaccharides is 35%. Diminished.
以上説明したように、本発明により、純度の高い大豆オ
リゴ糖が高収率で得られるようになったものである。又
、この大豆オリゴ糖はビフィヅス菌増殖促進物質として
、又低甘味剤として種々の食品に利用できるだけでなく
機能性素材として各種飲料等に用いることもできる。As explained above, according to the present invention, highly pure soybean oligosaccharides can be obtained in high yield. In addition, this soybean oligosaccharide can be used not only as a bifidobacteria growth promoter and as a low sweetener in various foods, but also as a functional material in various beverages.
Claims (1)
、リン酸を用いてｐＨ３以下に調整し、生じた沈澱物を
除去することを特徴とする大豆オリゴ糖の製造法。(1) A method for producing soybean oligosaccharides, which comprises heating a soybean whey solution at 70 to 110°C, adjusting the pH to 3 or less using phosphoric acid, and removing the resulting precipitate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2319531A JP2635210B2 (en) | 1990-11-21 | 1990-11-21 | Manufacturing method of soybean oligosaccharide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2319531A JP2635210B2 (en) | 1990-11-21 | 1990-11-21 | Manufacturing method of soybean oligosaccharide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04187695A true JPH04187695A (en) | 1992-07-06 |
| JP2635210B2 JP2635210B2 (en) | 1997-07-30 |
Family
ID=18111283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2319531A Expired - Fee Related JP2635210B2 (en) | 1990-11-21 | 1990-11-21 | Manufacturing method of soybean oligosaccharide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2635210B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004104036A1 (en) * | 2003-05-21 | 2004-12-02 | Fuji Oil Company, Limited | Process for producing soyeban whey protein and digested soybean whey protein |
| US9909119B2 (en) | 2013-11-07 | 2018-03-06 | Toray Industries, Inc. | Method for producing purified soybean oligosaccharide liquid |
-
1990
- 1990-11-21 JP JP2319531A patent/JP2635210B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004104036A1 (en) * | 2003-05-21 | 2004-12-02 | Fuji Oil Company, Limited | Process for producing soyeban whey protein and digested soybean whey protein |
| US9909119B2 (en) | 2013-11-07 | 2018-03-06 | Toray Industries, Inc. | Method for producing purified soybean oligosaccharide liquid |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2635210B2 (en) | 1997-07-30 |
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