JPS59223756A - Production of anthocyanin pigment - Google Patents

Production of anthocyanin pigment

Info

Publication number
JPS59223756A
JPS59223756A JP9906183A JP9906183A JPS59223756A JP S59223756 A JPS59223756 A JP S59223756A JP 9906183 A JP9906183 A JP 9906183A JP 9906183 A JP9906183 A JP 9906183A JP S59223756 A JPS59223756 A JP S59223756A
Authority
JP
Japan
Prior art keywords
pigment
resin
soln
anthocyanin
dye
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.)
Pending
Application number
JP9906183A
Other languages
Japanese (ja)
Inventor
Akira Yasuda
侃 安田
Kinnosuke Kotake
欣之輔 小竹
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
San Ei Kagaku Co Ltd
Sanei Kagaku Kogyo KK
Original Assignee
San Ei Kagaku Co Ltd
Sanei Kagaku Kogyo KK
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by San Ei Kagaku Co Ltd, Sanei Kagaku Kogyo KK filed Critical San Ei Kagaku Co Ltd
Priority to JP9906183A priority Critical patent/JPS59223756A/en
Publication of JPS59223756A publication Critical patent/JPS59223756A/en
Pending legal-status Critical Current

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  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

PURPOSE:To produce the titled pigment in a high purity industrially advantageously, by purifying an aq. acidic extract contg. anthocyanin dye with a cationic or adsorptive resin and treating it with an ultrafiltration membrane. CONSTITUTION:A raw material contg. anthocyanin pigment, e.g. purple corn, red cabbage, berry of grape rind is extracted with an aq. acidic soln. having a pH of 4.0 or below. The extract is contacted with a cationic or adsorptive resin to adsorb the pigment on the resin. The resin is washed with water at 40 deg.C or below. The desorption of the pigment is then carried out with an aq. alcoholic or alkaline soln. at 40 deg.C or below. The pH of the resulting soln. is adjusted to 1.0-7.0 and the soln. is treated with an ultrafiltration membrane having 2,000-200,000 fractions. EFFECT:Foods which must have transparent appearance can be clearly colored without causing turbidity or precipitation.

Description

【発明の詳細な説明】 この発明は、色素に係るものであって、工業的に有利に
高純度のアントシアニン色素を得ることを目的とする。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to pigments and aims to obtain industrially advantageous highly pure anthocyanin pigments.

アントシアニン色素は、紫トウモロコシ、赤キャベツ、
ブドウの果皮、果汁、ベリー類、その他に含有されてい
ることは周知であるか、これ等の原料から効率良く高品
位にアントシアニン色素を収得することが、当業者の課
題となる。
Anthocyanin pigments are found in purple corn, red cabbage,
It is well known that anthocyanin pigments are contained in grape skins, fruit juice, berries, and others, and it is a challenge for those skilled in the art to efficiently obtain high-quality anthocyanin pigments from these raw materials.

この発明は、低温範囲(40°C以下)で目的とする色
素の損失を少なく、かつ高品位において11又得するこ
とによシ、この課題にこたえようとするものであって以
下に、その詳利1を説明する。
The present invention attempts to meet this problem by reducing the loss of the target dye in the low temperature range (40°C or less) and obtaining high quality. Let me explain benefit 1.

まず、アントシアニン色素の水溶γ伏ヲ111意する。First, let us consider the water-soluble γ-forms of anthocyanin pigments.

アントシアニン色素は、酸性水抽出液で上記1京本1か
ら安定に溶出する。酸性水溶液に使用される酸類として
は、塩酸、イが[1酸その他の鉱酸、クエン酸、酒石酸
、リンゴ酸、その他の有機酸があけられる。
Anthocyanin pigments are stably eluted from the above-mentioned 1 Kyomoto 1 with an acidic water extract. Examples of acids used in the acidic aqueous solution include hydrochloric acid, acid and other mineral acids, citric acid, tartaric acid, malic acid, and other organic acids.

p Hは4.Q以下が色素の収率向上のため、好」■で
める。I) Llが4.0ヲこえてアルカリ1閑になる
と収率が低下する。
pH is 4. Q or less is preferable because it improves the dye yield. I) When Ll exceeds 4.0 and the alkali level decreases to 1, the yield decreases.

抽出工程から得たアントシアニン色素含有の水溶液を精
製するだめの樹脂は、カチメーン性あるいは吸着性のも
の全採用する。
The resin used to purify the aqueous solution containing anthocyanin pigments obtained from the extraction process is either cationic or adsorptive.

吸着樹脂としては、デュオライl−X、 A I) 2
、XAI)−4、XAI)−7、ダイヤイオン1−1.
 P−50、H,P−20その他があげられる。カチオ
ン性樹脂としてはデュオライトQ−8、C−10、C−
20、S−30、その他があけられる。精製方法は次の
通りである。アントシアニン色素含有の前記酸性水溶液
を流し、色素を樹脂に吸着させ、水洗(11旧流、逆流
いずれでも司)後、アルコ−/し水またはアルカリ水な
どで脱着する。この工程において腋の温度は40゛C以
下とすることが重要である。
As the adsorption resin, Duoly I-X, A I) 2
, XAI)-4, XAI)-7, Diamond 1-1.
Examples include P-50, H, P-20 and others. As the cationic resin, Duolite Q-8, C-10, C-
20, S-30, and others can be opened. The purification method is as follows. The acidic aqueous solution containing the anthocyanin pigment is passed through the resin, and the pigment is adsorbed onto the resin. After washing with water (either the old flow or the reverse flow in 11), the resin is desorbed with alcohol/mineral water or alkaline water. In this step, it is important to keep the temperature of the armpit below 40°C.

40°c2こえる温度にあっては、色素の収率が低下し
色相がわるくなる。
At temperatures above 40°c2, the dye yield decreases and the hue becomes worse.

この工程で夾雑物として1)!!質、’Uj(類、脂肪
、その他が除かれる。脱着した色素について、その1)
■1を調整することが必要である。その到達p Hは、
1.0〜7.0の範囲とする。I) l−1,7゜0を
こえると、目的物の収率がわるくなる。
1) as a contaminant in this process! ! Quality, 'Uj (kind, fat, etc. are removed.About desorbed pigments, part 1)
■It is necessary to adjust 1. The pH reached is
The range is 1.0 to 7.0. I) If it exceeds l-1,7°0, the yield of the target product will decrease.

つぎに精製した液を限外θゴ過膜で処理する。膜の種類
は、その原料によって、若干の差異かあるが総じて分子
量を分画(NIW )2,000〜200,000で分
別するのがよく、操作は限外I=過の常法による方法で
よい。赤キヤベツ抽出液の場合、圧力5 kq / e
yi、流速15n/min/−が最適テアリ、紫トウモ
ロコシの場合もほぼ同様である。この水液も前工程にお
けると同じく、40℃以下の温度で処理される。この工
程では夾雑物中、灰分、蛋白質、多糖類、酸類、その他
が除かれる。
Next, the purified liquid is treated with an ultra-theta filter membrane. The type of membrane varies slightly depending on the raw material, but in general it is best to separate the molecular weight by fractionating the molecular weight (NIW) from 2,000 to 200,000, and the operation is carried out using the conventional method of limiting I = 200,000. good. For red cabbage extract, pressure 5 kq/e
yi, a flow rate of 15 n/min/- is optimal for teali and purple corn. This aqueous solution is also treated at a temperature of 40° C. or lower, as in the previous step. This process removes impurities such as ash, protein, polysaccharides, acids, and others.

得られたアン1−シアニン色素か、目的の高品位のアン
トシアニン色素である。
The obtained anthocyanine dye is the desired high-grade anthocyanin dye.

この記明の製造イ去によればアントシアニン色素は高品
位で、高収率に告ることかでき、透明感を要する各棟の
食品に応用したときにlip明で、しかも濁り、沈澱、
その他の問題が解消したものである。
According to the manufacturing process described in this article, anthocyanin pigments are of high quality and have a high yield, and when applied to various foods that require transparency, they are lip bright, and they do not cause turbidity, precipitation, or
Other problems have been resolved.

ここに、この発明は、その目的を達しおえる。Here, the invention achieves its purpose.

樹脂精製した色素液は、限外p過時、透過流速が低下せ
ず又第2限外沖過時の色素・透過も大きい。
In the resin-purified dye liquid, the permeation flow rate does not decrease when passing through the extreme p limit, and the dye and permeation are large when passing through the second limit.

限外p過を行なわない色素は、飲料に使用時、経時的に
オリヲ生じ、また、他の色素や果汁と併用した場合、帯
電コロイドの有2()(によっては、沈澱を生ずること
があるか、との冗明における精製を行なったものに関し
ては、そのような現象は認められない。
Pigments that do not undergo ultrapolar permeation may cause precipitation over time when used in beverages, and if used in combination with other pigments or fruit juices, some may contain charged colloids and may form precipitates. No such phenomenon is observed in those that have been refined as stated above.

実  施  例  l 紫トウモロコシの種実1部(重量、以下同じ)を1%(
重量、以下同じ)個、角変lO部に40°C・30時間
浸漬し、赤紫色のアントシアニン色素抽出液(10’C
1この実施例において以下同じ)を得た。この液をダイ
ヤイオンJ−L I’ −5020部に吸着させてから
、水洗した後58容量形エチルアルコー/I/2部で色
素を勢≠て溶出した。
Example 1 1 part of purple corn seeds (weight, same hereinafter) was added to 1% (
weight, hereinafter the same) were immersed in an angular solution at 40°C for 30 hours to obtain a reddish-purple anthocyanin pigment extract (10'C).
1 In this example, the same applies hereinafter) was obtained. This solution was adsorbed onto 20 parts of Diaion J-L I'-50, washed with water, and the dye was eluted with 2 parts of 58 volume ethyl alcohol/I/1.

アルコールを留去して得た色素液をまず分画分子量6,
000の膜にットウNTU2006)を用いた限外沖過
全行ない、灰分、竹、酸、糖等の低分子夾雑物を除いた
。次にクエン酸でp H3,Qに調整した後、低分子夾
雑物を除いた。次に分画分子量10万の膜(二、 !・
−NTIJ85100 ’)で蛋白、澱粉、コロイド等
の高分子夾雑物を除いた。
The dye solution obtained by distilling off the alcohol is first divided into a molecular weight cutoff of 6,
000 membrane was subjected to an ultraviolet filtration process using TUTO NTU 2006) to remove low-molecular impurities such as ash, bamboo, acid, and sugar. Next, after adjusting the pH to 3, Q with citric acid, low molecular weight impurities were removed. Next, a membrane with a molecular weight cutoff of 100,000 (2, !・
-NTIJ85100') to remove polymeric impurities such as protein, starch, and colloids.

こnらの限外lJE過操作は圧力5 kq / ca・
流速111/朋n/−で行ない、透過流速は各28.6
0(at/pt//hr )  であった。梅脂による
前処理のため、限外濾過中の目詰まシもなく、高い透過
速度が得られ、又濃縮度も非常に[硲かった。
These extreme lJE over-operations require a pressure of 5 kq/ca.
The flow rate was 111/tomo/-, and the permeation flow rate was 28.6 each.
It was 0 (at/pt//hr). Because of the pretreatment with plum oil, there was no clogging during ultrafiltration, a high permeation rate was obtained, and the degree of concentration was also very high.

収得した色素は非常に7登明な赤色を呈し、仄酸飲料、
果汁飲*−1等に使用した際、経時的にオリの発生する
ことはなかった。
The obtained pigment has a very bright red color and is suitable for acidic beverages,
When used for fruit juice drink*-1, etc., no scum formed over time.

実  施  例  2 分キャベツ1部を磨砕し、1%クエン酸氷水2011に
40℃・30時間浸漬後、遠心分離濾過し、赤紫色のア
ントシアニン色素液を得た。この色素液を1部のデュオ
ライトXAD−7に1汲箔、水洗、次いで Δ58 V/V%エチルアルコール1部で色素を溶出シ
た。アルコールを留去した色素液をます分画分子量8,
000の膜(二〕1−−NTU3508)で糖、灰分、
酸等の低分子夾眉[物を除き、次いで分画分子−量10
万の;1ψ、にットーN T U 35100 )で限
外濾過を行ない蛋白質、澱粉、コ・ロイド物質等、高分
子のコロイド状夾雑物を除いた。
Example 2 One part of cabbage was crushed, immersed in 1% citric acid ice water 2011 at 40°C for 30 hours, and then centrifuged and filtered to obtain a reddish-purple anthocyanin pigment solution. This dye solution was poured into 1 part of Duolite XAD-7, washed with water, and then eluted with 1 part of Δ58 V/V% ethyl alcohol. The dye solution from which the alcohol has been distilled off is divided into a molecular weight cutoff of 8,
000 membrane (2)1--NTU3508) sugar, ash,
Low molecular weight substances such as acids [excluding substances, then fractionated molecules - weight 10
Ultrafiltration was performed with a filter of 10,000 mm, 1 ψ, NTU 35100) to remove macromolecular colloidal impurities such as proteins, starches, and colloidal substances.

収得した赤色素は、炭酸飲料や果汁飲月に着色した際、
経時的なオリの発生を認めなかった。赤ギャベツ色累は
陽性のコロイ1−゛イオン物質を含むので、従来法から
叫だものを使用し、た場合、果汁中の陰性コロイドイオ
ン(タンニン物質)が存在すると、経時的に共沈する現
象がみられたが、との発明の方法で収得した色素によシ
はじめて、果汁飲料にtfl−明に着色できた。
The obtained red pigment is used when coloring carbonated drinks and fruit juice drinks.
No occurrence of sludge over time was observed. Since red gabetsu contains positive colloid ions, if a method different from the conventional method is used, if negative colloid ions (tannin substances) are present in the fruit juice, they will co-precipitate over time. However, it was possible to color a fruit juice drink TFL-bright for the first time using the dye obtained by the method of the invention.

実施例3 エルダーベリー乾燥物ttilを粉イ17〜後、1%硫
酸20部に、40°C5時間、浸漬攪拌、次いで〃4別
した色素液をタイヤイオンHP −20吸着樹脂2部に
吸着、水洗後58V/、V%エチルアルコール1部で溶
出した。溶出色素のアルコールを留去した液について、
まず分画分子量5,000で限外f過を行なった。次い
で分画分子量10ガで限外濾過を行なった。
Example 3 After powdering ttil of dried elderberry for 17 days, it was soaked and stirred in 20 parts of 1% sulfuric acid at 40°C for 5 hours, and then the separated color liquid was adsorbed on 2 parts of Tire Ion HP-20 adsorption resin. After washing with water, it was eluted with 1 part of 58V/V% ethyl alcohol. Regarding the liquid from which the alcohol of the eluted dye was distilled off,
First, ultraf filtration was performed at a molecular weight cutoff of 5,000. Next, ultrafiltration was performed using a molecular weight cutoff of 10 ga.

これらの処理で低分子の硫酸、糖、夾雑物及び    
゛タンニン様物質、蛋白、晒粉等の高分子夾!i:11
:物を除去する。収得した色素は高濃縮液においても低
粘度であシ、水溶液は澄明で経時的にオリの発生は少な
かった。
These treatments remove low-molecular sulfuric acid, sugar, impurities and
゛Contains polymers such as tannin-like substances, proteins, and bleached powder! i:11
: Remove something. The obtained dye had a low viscosity even in a highly concentrated solution, and the aqueous solution was clear and little sludge formed over time.

特f「出願人 三栄化学工梁株式会社Special f “Applicant Sanei Chemical Engineering Co., Ltd.

Claims (1)

【特許請求の範囲】[Claims] 紫トウモ、ロコシ、赤キャベツ、ベリー類、ブドウ果皮
その他のアントシアニン色素を含有するものの酸性水抽
出液をカチオン性、あるいは吸着性樹脂を用いて精製し
、更にp I:L 7. Q以下にした後限外p過膜(
分画2,000〜200,000)で処理することに特
徴を有するアントシアニン色素の製造法。
Acidic water extracts of purple corn, red cabbage, berries, grape skins, and other substances containing anthocyanin pigments are purified using a cationic or adsorbent resin, and further p I:L 7. After setting the value below Q, the ultrap-filtering film (
A method for producing an anthocyanin pigment characterized by treatment with fractions 2,000 to 200,000.
JP9906183A 1983-06-02 1983-06-02 Production of anthocyanin pigment Pending JPS59223756A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP9906183A JPS59223756A (en) 1983-06-02 1983-06-02 Production of anthocyanin pigment

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP9906183A JPS59223756A (en) 1983-06-02 1983-06-02 Production of anthocyanin pigment

Publications (1)

Publication Number Publication Date
JPS59223756A true JPS59223756A (en) 1984-12-15

Family

ID=14237210

Family Applications (1)

Application Number Title Priority Date Filing Date
JP9906183A Pending JPS59223756A (en) 1983-06-02 1983-06-02 Production of anthocyanin pigment

Country Status (1)

Country Link
JP (1) JPS59223756A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6136364A (en) * 1984-07-27 1986-02-21 San Ei Chem Ind Ltd Method for purifying dyestuff anthocyanin
JPH02163037A (en) * 1988-12-14 1990-06-22 Maruhachi:Kk Pickles of red turnip
WO2001011988A3 (en) * 1999-08-13 2001-09-13 Dry Creek Nutrition Inc Novel polyphenolic polymeric compositions, method of their isolation, and a method of altering and improving taste characteristics of edible consumables
WO2003064538A1 (en) * 2002-02-01 2003-08-07 San-Ei Gen F.F.I., Inc. Purified purple corn color and method of preparing the same
WO2008039375A1 (en) * 2006-09-25 2008-04-03 Wild Flavors, Inc. Treatment of plant juices, extracts, and pigments
US7658963B1 (en) 1999-07-02 2010-02-09 Meiji Seika Kaisha, Ltd. Compositions for foods, process for producing the same and functional foods and drinks containing the same
CN102229753A (en) * 2011-04-20 2011-11-02 淮北普豪生物科技有限公司 Method for extracting purple corn pigment
US8153866B2 (en) 2007-06-21 2012-04-10 Suntava Llc Corn inbreds like FAR045 and hybrids thereof
CN102660141A (en) * 2012-05-22 2012-09-12 南京农业大学 Method for extracting anthocyanin from fruit epidermis
JP2014520912A (en) * 2011-06-30 2014-08-25 イー アンド ジェイ ガロ ワイネリイ Natural crystalline colorant and process
US11352501B2 (en) 2014-08-26 2022-06-07 San-Ei Gen F.F.I., Inc. Anthocyanin-based pigment composition

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50103526A (en) * 1974-01-21 1975-08-15
JPS5221032A (en) * 1975-07-22 1977-02-17 Fuaburikashion E Do Konmerushi Method of treating anthocyanin extracts
JPS53111331A (en) * 1977-01-24 1978-09-28 Rhone Poulenc Ind Purification method of anthocyanin
JPS5453141A (en) * 1977-09-13 1979-04-26 Welch Foods Inc Separation of anthocyanine

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50103526A (en) * 1974-01-21 1975-08-15
JPS5221032A (en) * 1975-07-22 1977-02-17 Fuaburikashion E Do Konmerushi Method of treating anthocyanin extracts
JPS53111331A (en) * 1977-01-24 1978-09-28 Rhone Poulenc Ind Purification method of anthocyanin
JPS5453141A (en) * 1977-09-13 1979-04-26 Welch Foods Inc Separation of anthocyanine

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0441185B2 (en) * 1984-07-27 1992-07-07 Sanei Kagaku Kogyo Kk
JPS6136364A (en) * 1984-07-27 1986-02-21 San Ei Chem Ind Ltd Method for purifying dyestuff anthocyanin
JPH02163037A (en) * 1988-12-14 1990-06-22 Maruhachi:Kk Pickles of red turnip
US7658963B1 (en) 1999-07-02 2010-02-09 Meiji Seika Kaisha, Ltd. Compositions for foods, process for producing the same and functional foods and drinks containing the same
US8722126B2 (en) 1999-07-02 2014-05-13 Meiji Co., Ltd. Compositions for food, process for producing the same, and functional foods and drinks containing the same
WO2001011988A3 (en) * 1999-08-13 2001-09-13 Dry Creek Nutrition Inc Novel polyphenolic polymeric compositions, method of their isolation, and a method of altering and improving taste characteristics of edible consumables
WO2003064538A1 (en) * 2002-02-01 2003-08-07 San-Ei Gen F.F.I., Inc. Purified purple corn color and method of preparing the same
US7192456B2 (en) 2002-02-01 2007-03-20 San-Ei Gen F.F.I., Inc., Method of preparing a purified purple corn coloring agent
WO2008039375A1 (en) * 2006-09-25 2008-04-03 Wild Flavors, Inc. Treatment of plant juices, extracts, and pigments
US8153866B2 (en) 2007-06-21 2012-04-10 Suntava Llc Corn inbreds like FAR045 and hybrids thereof
US8642847B2 (en) 2007-06-21 2014-02-04 Lee K. French Corn inbreds like FAR601 and hybrids thereof
CN102229753A (en) * 2011-04-20 2011-11-02 淮北普豪生物科技有限公司 Method for extracting purple corn pigment
JP2014520912A (en) * 2011-06-30 2014-08-25 イー アンド ジェイ ガロ ワイネリイ Natural crystalline colorant and process
JP2015221902A (en) * 2011-06-30 2015-12-10 イー アンド ジェイ ガロ ワイネリイE. & J. Gallo Winery Natural crystal colorant agent and production method thereof
CN102660141A (en) * 2012-05-22 2012-09-12 南京农业大学 Method for extracting anthocyanin from fruit epidermis
US11352501B2 (en) 2014-08-26 2022-06-07 San-Ei Gen F.F.I., Inc. Anthocyanin-based pigment composition

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