JPH01132344A - Food and drink - Google Patents

Food and drink

Info

Publication number
JPH01132344A
JPH01132344A JP63264222A JP26422288A JPH01132344A JP H01132344 A JPH01132344 A JP H01132344A JP 63264222 A JP63264222 A JP 63264222A JP 26422288 A JP26422288 A JP 26422288A JP H01132344 A JPH01132344 A JP H01132344A
Authority
JP
Japan
Prior art keywords
food
natural products
acid
fading
drink
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
Application number
JP63264222A
Other languages
Japanese (ja)
Other versions
JPH0333298B2 (en
Inventor
Osamu Inami
治 稲波
Itaru Tamura
至 田村
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.)
T Hasegawa Co Ltd
Original Assignee
T Hasegawa Co Ltd
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 T Hasegawa Co Ltd filed Critical T Hasegawa Co Ltd
Priority to JP63264222A priority Critical patent/JPH01132344A/en
Publication of JPH01132344A publication Critical patent/JPH01132344A/en
Publication of JPH0333298B2 publication Critical patent/JPH0333298B2/ja
Granted legal-status Critical Current

Links

Abstract

PURPOSE:To obtain a food and drink capable of preventing alteration of flavor, by blending a fading inhibitor containing chlorogenic acid separated from natural products and/or caffeic acid synthesized or separated from natural products in a food and drink containing an anthocyanin based pigment. CONSTITUTION:A fading inhibitor consisting of chlorogenic acid separated from natural products and/or caffeic acid synthesized or separated from natural products may contain 100% active ingredient or in the form of a composition with a suitable diluent or carrier. For example, a solid, such as gum arabic or glucose, a liquid, such as water or ethanol, is used as the diluent or carrier. Any of powdery, granular and liquid forms may be suitable as the dosage form. The inhibitor may be in the form of a blend with an anthocyanin based pigment. Such a fading inhibitor in an adequate amount is blended with a food and drink containing the anthocyanin based pigment to provide a product.

Description

【発明の詳細な説明】 本発明は、酸素、光などに対して不安定である点でその
利用上トラブルのあるアントンアニン系色素含有飲料物
に関する。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an antonine-based pigment-containing beverage that is problematic in its use because it is unstable to oxygen, light, and the like.

更に詳しくは、本発明は、天然物から分離されたクロロ
ゲン酸及び/又は合成もしくは天然物から分離されたカ
フェー酸を有効成分とする退色防止剤を、アントンアニ
ン系色素含有飲料物中に含有することを特徴とする飲食
物に関する。
More specifically, the present invention contains an antifading agent containing chlorogenic acid isolated from a natural product and/or caffeic acid isolated from a synthetic or natural product as an active ingredient in a beverage containing an anthonaniline pigment. This invention relates to food and drink characterized by the following.

例えば、ブドウ果皮色素、ハイビスカス色素、エルダー
ベリー色素、ラズベリー色素、シソ色素その他の天然も
しくは合成アントンアニン系色素は、赤色乃至赤紫色系
色調を賦与する色素として、例えば、飲食物、化粧品、
保健・医薬品などの分野で利用され、とくに飲食物の着
色に広く利用されている。
For example, grape skin pigments, hibiscus pigments, elderberry pigments, raspberry pigments, perilla pigments, and other natural or synthetic anthonanine pigments are used as pigments that impart red to reddish-purple hues, for example, in foods, drinks, cosmetics, etc.
It is used in fields such as health care and medicine, and is especially widely used for coloring food and drinks.

このようなアントンアニン系色素は、酸素、光などに対
して不安定であることは良く知られており、また、水溶
液中でpHが低酸性側から中性に近づくに従って著るし
く不安定となり、退色乃至変色(本発明においては退色
と総称する)するトラブルのあることも知られている。
It is well known that such anthonanine dyes are unstable to oxygen, light, etc., and they become significantly unstable in aqueous solutions as the pH approaches neutrality from low acidity. It is also known that there is a problem of fading or discoloration (generally referred to as discoloration in the present invention).

更に、アントンアニン系色素では、アスコルビン酸の存
在下では光のみならず熱に対しても著るしく不安定で退
色し易いことが知られている。
Furthermore, it is known that in the presence of ascorbic acid, anthonanine dyes are extremely unstable not only to light but also to heat and are susceptible to fading.

従来、このようなアントンアニン系色素が有する不安定
性のトラブルを克服する目的で種々の安定化成分を配合
して安定化しようとする試みや提案がなされてきたが、
充分満足すべき効果が得られないのが実情である。
In the past, attempts and proposals have been made to stabilize the antonine dyes by incorporating various stabilizing components in order to overcome the problem of instability that they have.
The reality is that a fully satisfactory effect cannot be obtained.

本発明者等は、このようなアントンアニン系色素の退色
のトラブルを克服できる退色防止剤の開発について研究
を行ってきた。
The present inventors have conducted research on the development of an anti-fading agent that can overcome the problem of fading of anthonanine dyes.

その結果、天然物から分離されたクロロゲン酸及び/又
は合成もしくは天然物から分離されたカフェー酸がアン
トンアニン系色素の退色に対して、優れた防止効果を発
揮することを発見した。更に、アスコルビン酸の存在下
では光のみならず熱に対しても退色し易いアントンアニ
ン系色素の退色防止に際して、アスコルビン酸の存在下
でも優れた防止効果を発揮することを知った。又更に、
前述の如きこれら色素の利用される広い分野で退色防止
剤として有用であるが、とくにこれら色素を含有する飲
食物分野において好適に利用でき、飲食物に不都合な香
味変調を生ずることなしに、優れた退色防止効果を賦与
できる優れた防止剤であることがわかった。
As a result, it has been discovered that chlorogenic acid isolated from natural products and/or caffeic acid isolated from synthetic or natural products exhibits an excellent preventive effect against fading of anthonanine pigments. Furthermore, it has been found that in the presence of ascorbic acid, an excellent preventive effect is exhibited even in the presence of ascorbic acid in preventing the fading of anthonanine pigments that are susceptible to fading not only by light but also by heat. Furthermore,
These pigments are useful as anti-fading agents in a wide range of fields where they are used, as mentioned above, but they are particularly suitable for use in the field of foods and beverages that contain these pigments, and can be used as an excellent anti-fading agent without causing any unfavorable flavor changes in foods or beverages. It was found that it is an excellent inhibitor that can provide a discoloration prevention effect.

従って、本発明の目的はアントンアニン系色素を含有す
る飲食物への利用を提供するにある。
Therefore, an object of the present invention is to provide the use of anthonaniline pigments in foods and drinks containing them.

本発明の上記目的及び更に多くの他の目的ならびに利点
は、以下の記載から一層明らかとなるであろう。
The above objects and many other objects and advantages of the present invention will become more apparent from the following description.

クロロゲン酸(3−カフエイルキナ酸)は、下記式 で表わすことのできる化合物であって、たとえばコーヒ
ー豆中にクロロゲン酸カリウムカフェインの形で含有さ
れ、微量にはタバコ葉、サツマイモ、ナシ葉、茶菓、リ
ンゴ果肉その他広く植物中に分布する。又、カフェー酸
(3,4−ジオキシケイ皮酸、3,4−ジオキシニラケ
イ酸は、下記式で表わすことのできる化合物であって、
コーヒータンニンの水酸化カリウムケン化物として単離
され、又、1878年T iemannらにより合成さ
れた。
Chlorogenic acid (3-caffeylquinic acid) is a compound that can be represented by the following formula, and is contained, for example, in the form of potassium chlorogenic acid caffeine in coffee beans, and in trace amounts in tobacco leaves, sweet potatoes, pear leaves, and tea confectionery. , apple pulp and other plants are widely distributed. In addition, caffeic acid (3,4-dioxycinnamic acid, 3,4-dioxynillasilicic acid is a compound that can be represented by the following formula,
It was isolated as a saponified potassium hydroxide product of coffee tannin, and was also synthesized in 1878 by Tiemann et al.

針葉樹皮、タデ科植物、タバコなどに遊離状で存在する
が、クロロゲン酸としてコーヒー豆をはじめ広く分布す
る。クロロゲン酸からキナ酸部分を脱離させて得ること
もできる。本発明においてはこれらクロロゲン酸及び/
又はカフェー酸が利用され、本発明においては核酸の水
溶性塩酸を包含する呼称である。例えば、カフェー酸ナ
トリウム、カフェー酸カリウムの如き塩類を例示できる
It exists in free form in coniferous bark, Polygonaceae, tobacco, etc., but is widely distributed as chlorogenic acid, including coffee beans. It can also be obtained by removing the quinic acid moiety from chlorogenic acid. In the present invention, these chlorogenic acids and/or
Alternatively, caffeic acid is used, and in the present invention, the name includes water-soluble hydrochloric acid of nucleic acids. For example, salts such as sodium caffeate and potassium caffeate can be exemplified.

本発明の退色防止剤に於ては、上述の如き天然物から分
離されたクロロゲン酸及び/又は合成もしくは天然物か
ら分離されたカフェー酸が有効成分である。本発明退色
防止剤は、これら有効成分の100%から成っていても
よいし、これら有効成分と適当な希釈剤もしくは担体と
の組成物の形態であってもよい。このような希釈剤もし
くは担体の例としては、アラビアガム、デキストリン、
グリコース、シュクロースなどの如き固体希釈剤もしく
は担体、水、エタノール、プロピレングリコール、グリ
セリン、界面活性剤、などの如き液体希釈剤もしくは担
体を例示することができる。
In the antifading agent of the present invention, chlorogenic acid isolated from natural products as described above and/or caffeic acid isolated from synthetic or natural products are active ingredients. The antifading agent of the present invention may consist of 100% of these active ingredients, or may be in the form of a composition of these active ingredients and a suitable diluent or carrier. Examples of such diluents or carriers include gum arabic, dextrin,
Examples include solid diluents or carriers such as glycose, sucrose, etc., liquid diluents or carriers such as water, ethanol, propylene glycol, glycerin, surfactants, and the like.

本発明の退色防止剤は、任意の剤形で利用してよく、例
えば、粉末状、顆粒状、液状、乳液状、ペースト状その
他適宜の剤形であることができる。
The antifading agent of the present invention may be used in any desired dosage form, such as powder, granules, liquid, emulsion, paste, or other appropriate dosage forms.

更に、本発明の退色防止剤は、アントンアニン系色素と
の配合物の形態であってもよい。
Further, the antifading agent of the present invention may be in the form of a blend with an anthonaniline dye.

例えば、アラビアガム、デキストリンなどを添加して粉
末状、顆粒状などの剤形で使用しても良く、また例えば
エタノール、プロピレングリフール、グリセリン、或い
はこれらの混合物に溶解して液状剤形として使用するこ
ともでき、更に例えばアラビアガムなどの天然ガム質、
或いは界面活性剤を添加して乳液状剤形として使用して
も良い。
For example, it may be used in a powdered or granular form by adding gum arabic, dextrin, etc., or it may be used as a liquid form by dissolving it in, for example, ethanol, propylene glyfur, glycerin, or a mixture thereof. In addition, natural gums such as gum arabic,
Alternatively, it may be used as an emulsion by adding a surfactant.

本発明の天然物から分離されたクロロゲン酸及び/又は
合成もしくは天然物から分離されたカフェー酸を有効成
分とする上記退色防止剤を利用して、該退色防止剤をア
ントンアニン系色素含有飲食物中に含有することを特徴
とする飲食物を提供することができる。
Utilizing the above-mentioned anti-fading agent containing chlorogenic acid isolated from a natural product and/or caffeic acid isolated from a synthetic or natural product as an active ingredient, the anti-fading agent can be added to an anthonaniline pigment-containing food or drink. It is possible to provide a food or drink characterized by containing the following.

このような飲食品の例としては、無果汁飲料、果汁入飲
料、乳酸菌飲料、粉末飲料などの如き飲料類;アイスク
リーム、シャーベット、氷菓などの如き冷菓類ニブリン
、ゼリー、ババロア、ヨーグルトなどの如きデザート食
品類などを例示することができる。
Examples of such foods and drinks include beverages such as non-fruit juice beverages, beverages with fruit juice, lactic acid bacteria beverages, powdered beverages, etc.; frozen desserts such as ice cream, sherbet, frozen desserts, etc.; Examples include dessert foods.

本発明の退色防止剤の添加量は、適宜な退色防止量を選
択できるが、クロロゲン酸及び/又はカフェー酸として
、例えば、約0.001〜約0.5重量%程度、更には
約0.O1〜約0.1重量%程度の範囲を好ましくは例
示できる。
The amount of the anti-fading agent of the present invention to be added can be selected to be an appropriate anti-fading amount, but for example, about 0.001 to about 0.5% by weight, more preferably about 0.001 to about 0.5% by weight, as chlorogenic acid and/or caffeic acid. A preferable example is a range of O1 to about 0.1% by weight.

本発明で利用するクロロゲン酸及び/又はカフェー酸は
市場で入手可能であるが、天然物に由来するクロロゲン
酸及び/又はカフェー酸は、必らずしも純品である必要
はなく、例えば下記の如くして得ることができる。
The chlorogenic acid and/or caffeic acid used in the present invention are commercially available, but the chlorogenic acid and/or caffeic acid derived from natural products do not necessarily have to be pure products, such as the following: It can be obtained as follows.

粉砕したコーヒー生豆に、例えば約0.5乃至約20倍
重量のエタノールもしくは含水エタノールを添加して、
たとえば約60℃乃至約100℃で、たとえば約1時間
乃至約10時間加熱する。
For example, by adding about 0.5 to about 20 times the weight of ethanol or water-containing ethanol to the ground coffee beans,
For example, heating at about 60° C. to about 100° C., for example, for about 1 hour to about 10 hours.

冷却後、不溶性固形分を分離、除去して得られる抽出液
に、塩酸濃度がたとえば約3〜lO%になるように塩酸
を添加して、たとえば約50°c−100°Cで、たと
えば約30分乃至約5時間加熱撹拌する。次いで濃縮後
、該濃縮溶液をたとえば多孔性重合樹脂で処理して該樹
脂に吸着させ、次いで該樹脂をたとえばエタノールで溶
出処理して、クロロゲン酸及び/又はカフェー酸を得る
ことができる。
After cooling, hydrochloric acid is added to the extract obtained by separating and removing insoluble solids so that the concentration of hydrochloric acid is, for example, about 3 to 10%, and the mixture is heated at, for example, about 50°C to 100°C, for example, about Heat and stir for 30 minutes to about 5 hours. After concentration, the concentrated solution can then be treated with, for example, a porous polymeric resin to adsorb onto the resin, and then the resin can be eluted with, for example, ethanol to obtain chlorogenic acid and/or caffeic acid.

以下、実施例により、本発明防止剤含有飲食物の調製及
び退色防止効果などについて、更に詳しく例示する。
Hereinafter, the preparation of the food and drink containing the inhibitor of the present invention and the effect of preventing fading will be illustrated in more detail with reference to Examples.

実施例1 コーヒー生豆300gをコーヒーミルにて粉砕し、この
粉砕物に5倍重量の70%エタノール水溶液を加えて、
90℃、2時間撹拌加熱した。冷却後不溶性固形分を除
去して、抽出液1.loogを得た。次いでこれに35
%塩酸180gを加えて、抽出液中の塩酸濃度が約5%
になるように調整し、70°O,1時間撹拌加熱した。
Example 1 300 g of green coffee beans were ground in a coffee mill, and 5 times the weight of a 70% aqueous ethanol solution was added to the ground product.
The mixture was stirred and heated at 90°C for 2 hours. After cooling, insoluble solids were removed and extract 1. I got loog. Then 35 to this
Add 180g of hydrochloric acid to reduce the concentration of hydrochloric acid in the extract to approximately 5%.
The mixture was stirred and heated at 70°O for 1 hour.

冷却後減圧下で300gになるまで濃縮し、得られた濃
縮液=7− に20%水酸化ナトリウムを添加してpH11以上に調
整し、次いで塩化メチレン600gを加えて充分撹拌混
合した。水相を分離し、これに10%塩酸を加えてpH
を6〜7に調整し、このpH調整液をダイヤイオンHP
−20樹脂500ccを充てんしたカラム中に徐々に流
した。次いで樹脂を充分水洗した後95%エタノール3
00gを流して樹脂にi着した物質を溶出させ、得られ
た溶液を減圧濃縮後、乾燥してクロロゲン酸及びカフェ
ー酸の混合物的12gを得た。
After cooling, the mixture was concentrated under reduced pressure to 300 g, and 20% sodium hydroxide was added to the resulting concentrated solution (7-) to adjust the pH to 11 or higher. Then, 600 g of methylene chloride was added and the mixture was thoroughly stirred and mixed. Separate the aqueous phase and add 10% hydrochloric acid to adjust the pH.
Adjust the pH to 6 to 7, and add this pH adjustment solution to Diaion HP.
-20 resin was gradually poured into a column filled with 500 cc. Next, after washing the resin thoroughly with water, 95% ethanol 3
The substance adhering to the resin was eluted by flowing 00 g of the resin, and the resulting solution was concentrated under reduced pressure and dried to obtain 12 g of a mixture of chlorogenic acid and caffeic acid.

実施例2〜5 ブドウ果皮色素をpH3の酒石酸ソーダ緩衝液にて希釈
してODo、54に調整した。次いでこの色素水溶液に
本発明による退色防止剤を添加して、無色透明の100
mffびんに入れ、6時間日光照射して色素残存率を測
定した。その結果を法衣に示した。本発明による退色防
止剤は、アンドシアン色素に対して著しい退色防止効果
を示すことが分った。
Examples 2 to 5 Grape skin pigments were diluted with a pH 3 sodium tartrate buffer to adjust the ODo to 54. Next, the anti-fading agent according to the present invention is added to this dye aqueous solution to obtain a colorless and transparent 100%
It was placed in an mff bottle, exposed to sunlight for 6 hours, and the dye residual rate was measured. The results were shown on the robe. It has been found that the anti-fading agent according to the present invention exhibits a remarkable anti-fading effect on andocyan dyes.

8一 実施例6 エルダベリー色素水溶液(OD 350/g) l 。81 Example 6 Elderberry dye aqueous solution (OD 350/g) 1.

Og、砂糖120g、酒石酸0.2gsクエン酸1゜2
g、 ビタミンCI 、Ogの混合物に水を加えてHと
する。これにカフェー酸0.2!5g添加して200m
Q透明びんに入れ、6時間日光照射して色素残存率を測
定したところ85%であった。一方退色防止剤を添加し
なかった対照品の色素残存率は55%であった。
Og, sugar 120g, tartaric acid 0.2gs citric acid 1゜2
Add water to a mixture of g, vitamin CI, and Og to obtain H. Add 0.2!5g of caffeic acid to this and make 200m
When placed in a Q transparent bottle and exposed to sunlight for 6 hours, the dye residual rate was measured and found to be 85%. On the other hand, the dye residual rate of the control product to which no anti-fading agent was added was 55%.

Claims (1)

【特許請求の範囲】[Claims] 1、天然物から分離されたクロロゲン酸及び/又は合成
もしくは天然物から分離されたカフエー酸を有効成分と
する退色防止剤を、アントンアニン系色素含有飲食物中
に含有することを特徴とする飲食物。
1. A food or drink characterized by containing an anti-fading agent containing chlorogenic acid isolated from a natural product and/or caffeic acid separated from a synthetic or natural product as an active ingredient in an anthonaniline pigment-containing food or drink. thing.
JP63264222A 1988-10-21 1988-10-21 Food and drink Granted JPH01132344A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP63264222A JPH01132344A (en) 1988-10-21 1988-10-21 Food and drink

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP63264222A JPH01132344A (en) 1988-10-21 1988-10-21 Food and drink

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
JP56162799A Division JPS5865761A (en) 1981-10-14 1981-10-14 Fading inhibitor for coloring matter and utilization thereof

Publications (2)

Publication Number Publication Date
JPH01132344A true JPH01132344A (en) 1989-05-24
JPH0333298B2 JPH0333298B2 (en) 1991-05-16

Family

ID=17400194

Family Applications (1)

Application Number Title Priority Date Filing Date
JP63264222A Granted JPH01132344A (en) 1988-10-21 1988-10-21 Food and drink

Country Status (1)

Country Link
JP (1) JPH01132344A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002233330A (en) * 2001-02-08 2002-08-20 Sanei Gen Ffi Inc Discoloring inhibitor
WO2007096643A1 (en) * 2006-02-23 2007-08-30 Med-Eq As Tea
CN102835649A (en) * 2012-01-18 2012-12-26 天津天康源生物技术有限公司 Gardenia yellow pigment colour retention agent and preparation method thereof
CN105199425A (en) * 2015-10-12 2015-12-30 南京农业大学 Extraction method of cyanidin

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002233330A (en) * 2001-02-08 2002-08-20 Sanei Gen Ffi Inc Discoloring inhibitor
WO2007096643A1 (en) * 2006-02-23 2007-08-30 Med-Eq As Tea
CN102835649A (en) * 2012-01-18 2012-12-26 天津天康源生物技术有限公司 Gardenia yellow pigment colour retention agent and preparation method thereof
CN105199425A (en) * 2015-10-12 2015-12-30 南京农业大学 Extraction method of cyanidin

Also Published As

Publication number Publication date
JPH0333298B2 (en) 1991-05-16

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