JP4013017B2 - Anti-fading agent for anthocyanin pigment and food containing the same - Google Patents

Description

【００１３】
本発明はこれらを一種単独で使用することもでき、また必要に応じて２種以上を組み合わせて用いることもできる。
【００１４】
なお、イソクロロゲン酸の塩としては、ナトリウム塩やカリウム塩といったアルカリ金属塩などの水溶性塩を挙げることができる。
【００１５】
使用するイソクロロゲン酸は化学合成品であってもよいし、天然物起源から採取したものでもよい。イソクロロゲン酸は、一般にサツマイモ、タバコ葉、ナシ葉、リンゴ果肉等の植物中に広く存在しているものであるが、含有量の割合を考慮すれば、サツマイモの塊根、茎、葉、等から採取するのが容易である。サツマイモとしては、特に種類を制限するものでないが、紅さつま、高系１４号、ベニアズマ、ベニオトメ、コガネセンガン、サツマヒカリ、サツマヒカリ、ベニハヤト等の他、アヤムラサキ，ブラジル原産紫サツマイモ（Ipoea batas, Lam..Convolvlaceae），山川紫，種子島在来，頴娃紫，知覧紫，喜入紫及びナカムラサキ等の紫さつまいも、及びそれらの改良品種を挙げることができる。
【００１６】
例えば出発材料としてサツマイモを用いる場合、イソクロロゲン酸は、例えば日本食品科学工学会誌、４３巻、３号、第313-317頁、（1996)に記載の方法から得ることができる。具体的には、まずサツマイモの塊根、茎、葉等を蒸煮するなどして加熱処理し、次いで乾燥処理して、粉砕し、含水エタノール水溶液で抽出し、得られた抽出物を必要に応じて濃縮して、次いで濃縮抽出物を、例えばゲル濾過、イオン交換等の各種カラムクロマトグラフィーに付してイソクロロゲン酸を分離、精製する方法を挙げることができる。
【００１７】
本発明で利用するイソクロロゲン酸またはその塩は必ずしも純品である必要はないが、退色防止剤を適用する例えば化粧品、食品または医薬品等の対象物の味や香りに影響を与えない程度にまで精製されているものが好ましい。
【００１８】
本発明の退色防止剤は、イソクロロゲン酸またはその塩を有効成分として含むものであれば、イソクロロゲン酸だけからなるものであってもよいし、また他成分として希釈剤、担体またはその他の添加剤を含有する組成物の形態であってもよい。希釈剤、担体及び添加剤は、本発明の効果を妨げないものであれば特に制限されず、例えばシュクロース、グルコース、デキストリン、アラビアゴム、水、エタノール、プロピレングリコール、グリセリン、水飴等を挙げることができる。
【００１９】
本発明の退色防止剤の形態は特に制限されず、例えば粉末状、顆粒状、錠剤状、液状、乳液状、ペースト状等の任意の形態として調製することができる。
【００２０】
本発明が対象とするアントシアニン系色素は、赤、青、紫系の色を呈するフラボノイド系の水溶性色素であり、具体的には、例えば、紫サツマイモ色素、赤キャベツ色素、エルダーベリー色素、ブドウ果汁色素、ブドウ果皮色素、ムラサキトウモロコシ色素、アカダイコン色素、シソ色素、赤米色素、カウベリー色素、グースベリー色素、クランベリー色素、サーモンベリー色素、スィムブルーベリー色素、ストロベリー色素、ダークスィートチェリー色素、チェリー色素、ハイビスカス色素、ハクルベリー色素、ブラックカーラント色素、ブラックベリー色素、ブルーベリー色素、プラム色素、ホワートルベリー色素、ボイセンベリー色素、マルベリー色素、ムラサキヤマイモ色素、ラズベリー色素、レッドカーラント色素、ローガンベリー色素、その他のアントシアニン系色素を挙げることができる。これらの色素は一種類で用いてもまた二種以上を任意に組み合わせて用いることもできる。
【００２１】
また、上記色素には、本発明の退色防止効果を損なわないことを限度に、他の色素を含むこともできる。
【００２２】
このような色素としては、コチニール色素、シコン色素、アカネ色素、ラック色素等のキノン系色素；カキ色素、カロブ色素、カンゾウ色素、シタン色素、スオウ色素、ベニバナ黄色素等のフラボノイド系色素；ベニコウジ色素、ベニコウジ赤色素等のアザフィロン色素；カロチン類やキサントフィル類等のカロチノイド色素及びその他の色素として、ベニバナ黄色素、ウコン色素、クサギ色素、クチナシ青色素、クチナシ黄色素、クチナシ赤色素、スピルリナ青色素等の天然色素やタール系色素等の合成色素を好適に例示することができる。なお、制限はされないが、タール系色素としては、例えば、食用赤色２号、食用赤色３号、食用赤色４０号、食用赤色１０２号、食用赤色１０４号、食用赤色１０５号、食用赤色１０６号、食用黄色４号、食用黄色５号、食用青色１号、食用青色２号、食用緑色３号等を挙げることができる。かかる色素とアントシアニン系色素との併用に対して、本発明の退色防止剤は、アントシアニン系色素のみならず総して退色防止効果を発揮することができる。
【００２３】
本発明の退色防止剤は、例えば上に掲げるアントシアニン系色素を含有するものに広く適用することができる。かかるものとしては、例えば食品、化粧品、医薬品、医薬部外品、飼料等を挙げることができる。
【００２４】
すなわち本発明は、退色防止剤としてイソクロロゲン酸またはその塩を含有する、アントシアニン系色素含有食品、化粧品、医薬品、医薬部外品及び飼料を提供するものである。なお、化粧品としてはスキンローション、口紅、日焼け止め化粧品、メークアップ化粧品等を、医薬品としては各種錠剤、カプセル剤、ドリンク剤、トローチ剤、うがい薬等を、医薬部外品としては歯磨き剤、口中清涼剤、口臭予防剤等を、また飼料としてはキャットフードやドッグッフード等の各種ペットフード、観賞魚若しくは養殖魚の餌等を一例として挙げることができるが、これらに制限されるものではない。
【００２５】
好ましくは、食品である。食品の例としては、制限されないが、アイスクリーム、アイスミルク、ラクトアイス、シャーベット、氷菓等の冷菓類；乳飲料、乳酸菌飲料、果汁入り清涼飲料、炭酸飲料、果汁飲料、粉末飲料等の飲料類；プリン、ゼリー、ババロア、ヨーグルト等のデザート類；チューインガムや風船ガム等のガム類（板ガム、糖衣状粒ガム）；ハードキャンディー（ボンボン、バターボール、マーブル等を含む）、ソフトキャンディー（キャラメル、ヌガー、グミキャンディー、マシュマロ等を含む）、ドロップ、タフィ等のキャラメル類；浅漬け、塩漬け、糠漬け、梅漬け等の漬物類；セパレートドレッシング、ノンオイルドレッシング、ケチャップ、たれ、ソースなどのソース類；ストロベリージャム、ブルーベリージャム、マーマレード等のジャム類；赤ワイン等の果実酒；その他、各種総菜及び蒲鉾、麩、田麩等の種々の加工食品を挙げることができる。
【００２６】
中でも弱酸性〜酸性の食品を好適に挙げることができる。具体的にはｐＨ５以下、好ましくはｐＨ４以下、より好ましくはｐＨ３．５以下の食品である。
【００２７】
これらの食品の製造工程において、本発明の退色防止剤及びアントシアニン系色素の配合工程及びその順番はとりわけ制限はないが、退色防止剤の存在下にアントシアニン系色素、好ましくはアントシアニン系色素及び香料を配合し、加熱処理等の各種の処理を施すことが望ましい。
【００２８】
例えば、冷菓類の場合は、まず主原料としての牛乳、クリーム、練乳、粉乳、糖類、果実、餡等に退色防止剤、酸類、乳化剤及び安定剤等、次いで香料を加えて冷菓ミックス液を調製し、このミックス液にアントシアニン系色素を添加混合し、次いで殺菌して容器に充填し、冷却、凍結して最終製品を調製する方法を挙げることができる。また飲料類の場合は、主原料としての糖類、果汁、酸類等に退色防止剤、安定剤等を加え、次いでこの飲料に香料及びアントシアニン系色素を添加混合した後、殺菌、冷却して容器に充填する方法を挙げることができる。また、ガム類の場合は、加熱し柔らかくしたガムベースに砂糖、ブドウ糖、退色防止剤及びクエン酸等を加え、次いでその中に香料及びアントシアニン系色素を加え練合する。次に圧延ローラーで適当な厚さにし、室温まで冷却後、切断して最終製品を調製する方法を挙げることができる。また、ゼリー類の場合は、主原料の砂糖、水飴、退色防止剤、クエン酸及び凝固剤（ペクチン、寒天、ゼラチン、カラギナンなど）を適当な割合で混合し、その中に香料並びにアントシアニン系色素を加え、加熱溶解した後、容器に充填し、冷却して最終製品たるゼリーを調製する方法を挙げることができる。キャンディー類の場合は、例えば砂糖、水飴等の主原料に水を加え加熱し溶解した後放冷し、退色防止剤を添加し、次いで香料及びアントシアニン系色素を加え、成型し、室温まで冷却して最終キャンディーを調製する方法を挙げることができる。漬物類の場合は、野菜、食塩、糖類、グルタミン酸ナトリウムを主原料とし、これに調味料及び退色防止剤等を加えて漬物を調製し、この漬物に香料及びアントシアニン系色素を添加混合した後、容器に充填し、殺菌、冷却し最終製品を調製する方法を挙げることができる。ドレッシング類の場合は、植物油、醤油、果汁、糖類、果汁、醸造酢、食塩等を主原料とし、これに退色防止剤、安定剤、乳化剤等を加え、このドレッシング液に香料及びアントシアニン系色素を添加混合した後、殺菌、冷却後容器に充填して最終製品を調製する方法を挙げることができる。
【００２９】
本発明の退色防止剤の食品、化粧品、医薬品、医薬部外品または飼料等の対象物への添加量は、それらに含まれるアントシアニン系色素の退色現象が防止できる量であれば特に制限されず、対象物の種類やそれに含まれる成分並びにアントシアニン系色素の含有量などを考慮して適宜選択、決定することができる。例えば対象物が食品の場合、食品に配合する退色防止剤の量はイソクロロゲン酸に換算して１０〜５００ｐｐｍの範囲を挙げることができる。また、上記対象物に含まれる色素に対する退色防止剤の割合は、色素の極大吸収波長における吸光度（Ａｂｓ）に対するイソクロロゲン酸の325nmでの吸光度の比率が１以上となるような割合を挙げることができる。
【００３０】
【実施例】
以下、本発明の内容を以下の実施例及び比較例を用いて具体的に説明するが、本発明はこれらに限定されるものではない。なお、下記に記載する処方の単位は特に言及しない限りｇを意味するものとする。
実施例１ かき氷シロップ液
液糖 ６５
砂糖 ３
クエン酸 ０．２５
カラギナン ０．３
食塩 ０．１５
エルダーベリー色素 ０．２
イソクロロゲン酸 ０．００５
（３，４−ジカフェオイルキナ酸）
水 適 量
合 計 １００．０００
上記の処方を添加混合し、かき氷シロップ液を調製した。
【００３１】
実験例１
上記実施例１においてイソクロロゲン酸の代わりにクロロゲン酸を、325nmにおける極大吸収でほぼ同一の吸光度となる量添加したかき氷シロップ液（比較品１）、並びに両方無添加のかき氷シロップ液（比較品２）を、実施例１と同様にして調製した。
【００３２】
実施例１のかき氷シロップ液及びこれらの比較品を用いて、第１の実験としてこれらの飲料を２００００ｌｕｘの蛍光灯照射の下に、５℃で５日間放置して、かき氷シロップ液の「耐光性」を試験した。また第２の実験として、これらのかき氷シロップ液を５０℃の恒温器内に１４日間放置して「耐熱性」を試験した。スタート時のシロップ液の色度を１００％（コントロール）として退色の程度を肉眼で比較した。結果を表１に示す。
【００３３】
【表１】

【００３４】
表１から明らかなように、イソクロロゲン酸を添加して調製した本発明のかき氷シロップ液は、クロロゲン酸を添加した比較品１よりも光照射後及び加熱処理後も退色が有意に抑制され、鮮明な赤色が維持されていた。
【００３５】
実施例２ アセロラ飲料
果糖ブドウ糖液糖 ７．０
砂糖 ５．０
クエン酸 ０．４
１／５アセロラ果汁 ４．４
アセロラフレーバー ０．２
赤キャベツ色素 ０．２
イソクロロゲン酸 ０．００５
（３，５−ジカフェオイルキナ酸、３，４−ジカフェオイルキナ酸混合物及び
４，５−ジカフェオイルキナ酸混合物）
水 適 量
合 計 １００．０００
果糖ブドウ糖及び砂糖の糖類、クエン酸、アセロラ果汁を主原料とし、これにイソクロロゲン酸及びアセロラフレーバーを加え、次いでこれに赤キャベツ色素を添加混合して容器に充填してアセロラ飲料を作った。
【００３６】
実験例２
上記実施例２においてイソクロロゲン酸の代わりにクロロゲン酸を、325nmにおける極大吸収でほぼ同一の吸光度となる量添加したアセロラ飲料（比較品３）、並びに両方無添加のアセロラ飲料（比較品４）を、実施例２と同様にして調製した。
【００３７】
実施例２のアセロラ飲料及びこれらの比較品を用いて、第１の実験としてこれらの飲料を１００００ｌｕｘの蛍光灯照射の下に、５℃で３日間放置して、アセロラ飲料の「耐光性」を試験した。また第２の実験として、これらの飲料を５０℃の恒温器内に７日間放置して「耐熱性」を試験した。スタート時の飲料の色度を１００％（コントロール）として退色の程度を肉眼で比較した。結果を表２に示す。
【００３８】
【表２】

【００３９】
表２から明らかなように、実験例１と同様に、イソクロロゲン酸を添加して調製した本発明のアセロラ飲料は、クロロゲン酸を添加した比較品３よりも、光照射後及び加熱処理後も退色が有意に抑制され、鮮明な赤色が維持されていた。光に対しても高い割合で退色現象が抑制されていたが、とりわけ加熱処理による退色現象がほぼ完全に抑制された。アントシアニン系色素は、特にアスコルビン酸の存在下で熱・光に対して不安定であることが知られているが、この実験からイソクロロゲン酸はアントシアニン系色素の耐熱性及び耐光性付与（特に耐熱性付与）に有意に寄与することが判明し、その効果はクロロゲン酸よりも有意に高かった。
【００４０】
実施例３ フルーツゼリー（ピーチゼリー）
果糖ブドウ糖液糖（７５％） ２０．０
１／５濃縮ホワイトピーチ果汁 ４．０
カラギナン １．０
クエン酸 ０．２
ピーチエッセンス ０．１
赤キャベツ色素 ０．１
イソクロロゲン酸 ０．００４
（３，５−ジカフェオイルキナ酸、３，４−ジカフェオイルキナ酸、４，５−ジ カフェオイルキナ酸及び３，４，５−トリカフェオイルキナ酸の混合物）
水 適 量
合 計 １００．０００
上記組成を添加混合し、８０℃１０分間加熱溶解後、カップに充填し、５℃１時間冷却し、フルーツゼリーを作った。
【００４１】
実施例４ ストロベリーシャーベット
砂糖 １５．０
粉末水飴 ７．５
硬化ヤシ油 １．０
脱脂粉乳 １．０
１／５濃縮ストロベリー果汁 ４．０
ストロベリーフレーバー ０．１
ブドウ果汁色素 ０．２２
イソクロロゲン酸 ０．００７
（３，４−ジカフェオイルキナ酸及び４，５−ジカフェオイルキナ酸の混合物）
水 適 量
合 計 １００．０００
脱脂粉乳、砂糖、粉末水飴、果汁を主原料とし、これにイソクロロゲン酸、硬化ヤシ油、香料を加えてミックス液とし、このミックス液にブドウ果汁色素を添加混合した。その後、殺菌、冷却及びフリージングして容器に充填して、これを０℃以下に冷却し凍結してストロベリーシャーベットを作った。
【００４２】
実施例５ アセロラガム
ガムベース １００
精製ブドウ糖 ２８８．９５
粉砂糖 １００
クエン酸 ０．５
アセロラフレーバー ５．０
アカダイコン色素 １．０
イソクロロゲン酸 ０．０５
（３，５−ジカフェオイルキナ酸及び４，５−ジカフェオイルキナ酸の混合物）
水 適 量
合 計 ５００．００
上記処方のうちアカダイコン色素以外の成分を混合、加熱して柔らかくした後、アカダイコン色素を添加し、練合して圧延ローラーで適当な厚さにし、室温まで冷却後、切断してアセロラガムを作った。
【００４３】
実施例６ ハードキャンデー
水２０ｇ、砂糖６０ｇ、水飴４０ｇの混合物を１５０℃まで加熱溶解し、煮詰めて１００ｇにした後、１２０℃まで冷却し、ブドウ果皮色素０．１ｇ、クエン酸０．５ｇ、アセロラフレーバー０．１５ｇ、イソクロロゲン酸（４，５−ジカフェオイルキナ酸）０．００８ｇを添加し、成型後、室温まで冷却してハードキャンディーを作った。
【００４４】
実施例７ 鰹風味の梅
梅酢 ４２．０
砂糖 ４．０
果糖ブドウ糖液糖 ２０．０
クエン酸 １．０
グルタミン酸ナトリウム ０．５
カツオエキス １．０
ムラサキトウモロコシ色素 ０．３
イソクロロゲン酸 ０．００６
（３，５−ジカフェオイルキナ酸及び４，５−ジカフェオイルキナ酸の混合物）
梅 ５０．０
水 適 量
合 計 １５０．００
上記処方を添加混合し、鰹風味の梅を調製した。
【００４５】
実施例８ 梅ドレッシング
醸造酢 ５．０
砂糖 ３．０
食塩 ２．６
醤油 ５．０
リンゴ酢 ５．０
レモン果汁 ３．０
グルタミン酸ナトリウム ０．５
コンブエキス １．０
カツオエキス １．０
梅肉 ３．０
シソオイル ０．０５
リンゴ酸 ０．４
シソ色素 ０．２
イソクロロゲン酸 ０．００８
（３，５−ジカフェオイルキナ酸）
コーンサラダ油 ４０．０
水 適 量
合 計 １００．０００
上記成分を各種添加混合した後、殺菌、冷却後容器に充填して梅ドレッシングを調製した。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an anti-fading agent for an anthocyanin dye and an anthocyanin dye-containing food containing the anti-fading agent. The present invention also relates to a new use of isochlorogenic acid.
[0002]
[Prior art]
Anthocyanin pigments are widely used in the fields of food, cosmetics, pharmaceuticals and the like as water-soluble natural pigments that impart a color tone from red to reddish purple.
[0003]
However, anthocyanin dyes are unstable to oxygen, light, and heat, and cause rapid discoloration or discoloration due to other influences such as these factors and additives during processing and storage of food, for example. Has drawbacks.
[0004]
For this reason, conventionally, various stabilizers and anti-fading agents have been studied and developed in order to eliminate the instability of such anthocyanin dyes and prevent the fading phenomenon.
[0005]
For example, Japanese Patent Application Laid-Open No. 58-65761 describes that chlorogenic acid and / or caffeic acid have an anti-fading effect on anthocyanin dyes.
[0006]
[Problems to be solved by the invention]
However, as the present inventors have confirmed, it cannot be said that the anti-fading effect of chlorogenic acid and / or caffeic acid on anthocyanin dyes is sufficiently satisfactory, and in particular, the fading of anthocyanin dyes due to heat cannot be sufficiently prevented. It was the actual situation.
[0007]
An object of the present invention is to provide an anti-fading agent capable of significantly suppressing the fading phenomenon of an anthocyanin dye. Furthermore, an object of the present invention is to provide a discoloration inhibitor having a significantly higher antifade effect of an anthocyanin dye than chlorogenic acid.
[0008]
Another object of the present invention is to provide an anthocyanin-containing food in which the fading phenomenon is significantly suppressed by containing such a fading preventing agent.
[0009]
[Means for Solving the Problems]
The inventors of the present invention have made extensive studies in order to achieve the above-mentioned problems. As a result, dicaffeoylquinic acid (isochlorogenic acid) exhibits an excellent prevention effect against fading of anthocyanin dyes, and It has been found that the preventive effect is significantly higher than that of the known chlorogenic acid. Furthermore, the present inventors have found that the isochlorogenic acid is particularly effective in preventing the fading phenomenon caused by heat treatment, and the effect is significantly higher than that of chlorogenic acid. The present invention has been developed based on such knowledge.
[0010]
That is, the present invention is an anti-fading agent for anthocyanin dyes containing the following isochlorogenic acid or a salt thereof as an active ingredient.
Item 1. An anti-fading agent for anthocyanin dyes, comprising isochlorogenic acid or a salt thereof as an active ingredient.
Item 2. Isochlorogenic acid is selected from the group consisting of 3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid and 3,4,5-tricaffeoylquinic acid Item 2. The anti-fading agent for anthocyanin dyes according to Item 1, which is at least one of the above.
Item 3. An anti-fading method for anthocyanin dyes, comprising blending the anti-fading agent for anthocyanin dyes according to Item 1 or 2 into foods, cosmetics, pharmaceuticals, quasi drugs or feeds containing anthocyanin dyes. .
Item 4. A method for preventing discoloration of an anthocyanin dye, which comprises blending an anthocyanin dye discoloration inhibitor described in Item 1 or 2 with a food containing an anthocyanin dye, and is an active ingredient of the discoloration inhibitor A method of blending isochlorogenic acid in a ratio of 2 to 8 parts by weight with respect to 100 parts by weight of an anthocyanin dye.
[0011]
DETAILED DESCRIPTION OF THE INVENTION
The anti-fading agent for anthocyanin dyes of the present invention is characterized by containing isochlorogenic acid as an active ingredient.
The isochlorogenic acid includes 3,5-dicaffeoylquinic acid represented by formula (1), 3,4-dicaffeoylquinic acid represented by formula (2), and 4,4 represented by formula (3). Three isomers of 5-dicaffeoylquinic acid and 3,4,5-tricaffeoylquinic acid represented by formula (4) are included.
[0012]
[Chemical 1]

[0013]
In the present invention, these may be used alone or in combination of two or more as required.
[0014]
Examples of the salt of isochlorogenic acid include water-soluble salts such as alkali metal salts such as sodium salt and potassium salt.
[0015]
The isochlorogenic acid used may be a chemically synthesized product or may be collected from a natural product source. Isochlorogenic acid is generally widely present in plants such as sweet potatoes, tobacco leaves, pear leaves, apple flesh, etc., but considering the proportion of the content, from roots, stems, leaves, etc. of sweet potatoes Easy to collect. The sweet potato is not particularly limited, but the red sweet potato, high line 14, veneer, beniotome, koganesengan, satsuhikari, satsumahikari, benihayato, etc. ), Purple purple sweet potatoes such as Yamakawa purple, Tanegashima native, Navy purple, Chiran purple, Kiir purple and Nakamurasaki, and their improved varieties.
[0016]
For example, when sweet potato is used as a starting material, isochlorogenic acid can be obtained from the method described in, for example, Journal of Japanese Society for Food Science and Technology, Vol. 43, No. 3, pp. 313-317, (1996). Specifically, the sweet potato tuberous roots, stems, leaves, etc. are first heated and then dried, then crushed, extracted with aqueous ethanol aqueous solution, and the resulting extract is used as necessary. A method of concentrating and then subjecting the concentrated extract to various column chromatography such as gel filtration and ion exchange to separate and purify isochlorogenic acid can be mentioned.
[0017]
Isochlorogenic acid or a salt thereof used in the present invention is not necessarily a pure product, but to the extent that it does not affect the taste and aroma of a target object such as cosmetics, foods or pharmaceuticals to which an anti-fading agent is applied. Those that have been purified are preferred.
[0018]
The anti-fading agent of the present invention may be composed only of isochlorogenic acid as long as it contains isochlorogenic acid or a salt thereof as an active ingredient, and may contain a diluent, carrier or other additive as another component. The form of the composition containing an agent may be sufficient. Diluents, carriers and additives are not particularly limited as long as they do not interfere with the effects of the present invention, and examples thereof include sucrose, glucose, dextrin, gum arabic, water, ethanol, propylene glycol, glycerin, varicella and the like. Can do.
[0019]
The form of the anti-fading agent of the present invention is not particularly limited, and can be prepared as an arbitrary form such as powder, granule, tablet, liquid, emulsion or paste.
[0020]
The anthocyanin pigments targeted by the present invention are flavonoid water-soluble pigments exhibiting red, blue, and purple colors. Specifically, for example, purple sweet potato pigments, red cabbage pigments, elderberry pigments, grapes Fruit juice pigment, grape skin pigment, purple corn pigment, red radish pigment, perilla pigment, red rice pigment, cowberry pigment, gooseberry pigment, cranberry pigment, salmon berry pigment, Sim Blueberry pigment, strawberry pigment, dark sweet cherry pigment, cherry Dye, Hibiscus Dye, Hakulberry Dye, Black Currant Dye, Blackberry Dye, Blueberry Dye, Plum Dye, White Berry Dye, Boysenberry Dye, Mulberry Dye, Purple Potato Dye, Raspberry Dye, Red Currant Dye, Logan Berry Dyes, mention may be made of other anthocyanin-based dye. These dyes can be used alone or in any combination of two or more.
[0021]
Moreover, the said pigment | dye can also contain another pigment | dye as long as it does not impair the fading prevention effect of this invention.
[0022]
Examples of such dyes include quinone dyes such as cochineal dyes, sicon dyes, red dyes and lac dyes; flavonoid dyes such as oyster dyes, carob dyes, licorice dyes, rosewood dyes, suou dyes and safflower dyes; Azaphylon pigments such as red beech mushroom red pigments; carotenoid pigments such as carotenes and xanthophylls and other pigments such as safflower yellow pigment, turmeric pigment, wedged pigment, gardenia blue pigment, gardenia yellow pigment, gardenia red pigment, spirulina blue pigment, etc. And natural pigments and synthetic pigments such as tar pigments can be suitably exemplified. Although not limited, examples of the tar-based pigment include food red No. 2, food red No. 3, food red No. 40, food red No. 102, food red No. 104, food red No. 105, food red No. 106, Food yellow No. 4, food yellow No. 5, food blue No. 1, food blue No. 2, food green No. 3, etc. can be mentioned. For the combined use of such a dye and an anthocyanin dye, the anti-fading agent of the present invention can exhibit an anti-fading effect as well as an anthocyanin dye.
[0023]
The anti-fading agent of the present invention can be widely applied to, for example, those containing the anthocyanin dyes listed above. Examples of such products include foods, cosmetics, pharmaceuticals, quasi drugs, and feeds.
[0024]
That is, the present invention provides an anthocyanin pigment-containing food, cosmetics, pharmaceuticals, quasi-drugs and feed containing isochlorogenic acid or a salt thereof as an anti-fading agent. Cosmetics include skin lotion, lipstick, sunscreen cosmetics, makeup cosmetics, etc., pharmaceuticals include various tablets, capsules, drinks, troches, mouthwashes, quasi-drugs, toothpastes, mouth Examples of the refreshing agent, the bad breath prevention agent and the like, and examples of feeds include various pet foods such as cat food and dog food, food for aquarium fish or cultured fish, and the like, but are not limited thereto.
[0025]
Preferably, it is a food. Examples of food include, but are not limited to, frozen confectionery such as ice cream, ice milk, lacto ice, sherbet, ice confectionery; beverages such as milk beverage, lactic acid bacteria beverage, soft drink with fruit juice, carbonated beverage, fruit juice beverage, powdered beverage; Desserts such as pudding, jelly, bavaroa, yogurt; gums such as chewing gum and bubble gum (board gum, sugar-coated granule gum); hard candy (including bonbon, butterball, marble, etc.), soft candy (caramel, nougat) , Gummy candy, marshmallow etc.), caramels such as drop, toffee; pickles such as pickled, salted, pickled, pickled; sauces such as separate dressing, non-oil dressing, ketchup, sauce, sauce; strawberry jam, Blueberry jam, marmalade, etc. S; fruit wine, such as red wine; Etc side dishes and kamaboko, bran, may be mentioned various processed foods such as Denbu.
[0026]
Among these, weakly acidic to acidic foods can be preferably mentioned. Specifically, it is a food having a pH of 5 or less, preferably a pH of 4 or less, more preferably a pH of 3.5 or less.
[0027]
In the production process of these foods, the blending process and the order of the antifading agent and anthocyanin dye of the present invention are not particularly limited, but an anthocyanin dye, preferably an anthocyanin dye and a fragrance are added in the presence of the antifading agent. It is desirable to mix and apply various treatments such as heat treatment.
[0028]
For example, in the case of frozen desserts, first prepare a frozen dessert mix solution by adding anti-fading agents, acids, emulsifiers, stabilizers, etc. to milk, cream, condensed milk, powdered milk, sugars, fruits, koji etc. In addition, there can be mentioned a method in which an anthocyanin dye is added to and mixed in this mixed solution, then sterilized and filled in a container, cooled and frozen to prepare a final product. In the case of beverages, add anti-fading agents, stabilizers, etc. to saccharides, fruit juices, acids, etc. as the main raw materials, and then add and mix fragrances and anthocyanin pigments to the beverage, then sterilize and cool to a container. A filling method can be mentioned. In the case of gums, sugar, glucose, an anti-fading agent, citric acid and the like are added to a heated and softened gum base, and then a fragrance and an anthocyanin pigment are added and kneaded. Next, a method of preparing a final product by adjusting the thickness to a suitable value with a rolling roller, cooling to room temperature, and then cutting it can be mentioned. In the case of jelly, the main ingredients such as sugar, starch syrup, anti-fading agent, citric acid and coagulant (pectin, agar, gelatin, carrageenan, etc.) are mixed in appropriate proportions, and flavors and anthocyanin pigments are mixed. And a method of preparing a jelly as a final product by filling the container and cooling it. In the case of candies, for example, water is added to the main ingredients such as sugar and syrup, heated and dissolved, allowed to cool, added with an anti-fading agent, then added with a fragrance and an anthocyanin pigment, molded, and cooled to room temperature. And a method of preparing the final candy. In the case of pickles, vegetables, salt, saccharides, sodium glutamate as the main raw materials, seasonings and anti-fading agent etc. are added to this to prepare pickles, and after adding fragrances and anthocyanin pigments to the pickles, A method of preparing a final product by filling a container, sterilizing and cooling can be mentioned. In the case of dressings, vegetable oil, soy sauce, fruit juice, sugar, fruit juice, brewed vinegar, salt, etc. are used as main ingredients, and anti-fading agents, stabilizers, emulsifiers, etc. are added to this, and flavoring and anthocyanin pigments are added to this dressing liquid. After adding and mixing, a method of preparing a final product by filling a container after sterilization and cooling can be mentioned.
[0029]
The amount of the anti-fading agent of the present invention added to an object such as food, cosmetics, pharmaceuticals, quasi drugs or feed is not particularly limited as long as it is an amount that can prevent the fading phenomenon of the anthocyanin pigments contained therein. It can be selected and determined as appropriate in consideration of the type of the object, the components contained therein, the content of the anthocyanin pigment, and the like. For example, when the object is a food, the amount of the anti-fading agent added to the food can be in the range of 10 to 500 ppm in terms of isochlorogenic acid. The ratio of the anti-fading agent to the dye contained in the object may be such that the ratio of the absorbance at 325 nm of isochlorogenic acid to the absorbance (Abs) at the maximum absorption wavelength of the dye is 1 or more. it can.
[0030]
【Example】
Hereinafter, the content of the present invention will be specifically described with reference to the following examples and comparative examples, but the present invention is not limited thereto. In addition, the unit of the prescription described below shall mean g unless otherwise specified.
Example 1 Shaved ice syrup liquid sugar 65
Sugar 3
Citric acid 0.25
Carrageenan 0.3
Salt 0.15
Elderberry pigment 0.2
Isochlorogenic acid 0.005
(3,4-dicaffeoylquinic acid)
water Appropriate amount
Total 100.000
The above recipe was added and mixed to prepare a shaved ice syrup solution.
[0031]
Experimental example 1
Shaved ice syrup solution (Comparative product 1) in which chlorogenic acid was added in an amount equivalent to the maximum absorbance at 325 nm in Example 1 instead of isochlorogenic acid, as well as shaved ice syrup solution (Comparative product 2) without both. ) Was prepared in the same manner as Example 1.
[0032]
Using the shaved ice syrup solution of Example 1 and a comparative product thereof as a first experiment, these beverages were allowed to stand at 20000 lux under fluorescent light irradiation at 5 ° C. for 5 days to obtain the “light resistance” of the shaved ice syrup solution. Was tested. As a second experiment, these shaved ice syrup solutions were left in a thermostat at 50 ° C. for 14 days to test “heat resistance”. The degree of fading was compared with the naked eye with the chromaticity of the syrup solution at the start as 100% (control). The results are shown in Table 1.
[0033]
[Table 1]

[0034]
As is clear from Table 1, the shaved ice syrup solution of the present invention prepared by adding isochlorogenic acid is significantly suppressed from fading after light irradiation and after heat treatment as compared with Comparative Product 1 to which chlorogenic acid was added. A clear red color was maintained.
[0035]
Example 2 Acerola Beverage Fructose Glucose Liquid Sugar 7.0
Sugar 5.0
Citric acid 0.4
1/5 acerola juice 4.4
Acerola Rever 0.2
Red cabbage pigment 0.2
Isochlorogenic acid 0.005
(3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid mixture and 4,5-dicaffeoylquinic acid mixture)
water Appropriate amount
Total 100.000
The main ingredients were fructose glucose and sugar saccharides, citric acid, and acerola juice. To this, isochlorogenic acid and acerola flavor were added, and then red cabbage pigment was added and mixed into the container to prepare an acerola beverage.
[0036]
Experimental example 2
In Example 2 above, an acerola beverage (Comparative Product 3) in which chlorogenic acid is added in place of isochlorogenic acid in an amount that gives almost the same absorbance at the maximum absorption at 325 nm, and an acerola beverage (Comparative Product 4) with no addition of both are obtained Prepared in the same manner as in Example 2.
[0037]
Using the acerola beverage of Example 2 and a comparative product thereof, as a first experiment, these beverages were left under 10000 lux fluorescent light irradiation at 5 ° C. for 3 days to improve the “light resistance” of the acerola beverage. Tested. As a second experiment, these beverages were left in a thermostat at 50 ° C. for 7 days to test “heat resistance”. The degree of fading was compared with the naked eye with the chromaticity of the beverage at the start as 100% (control). The results are shown in Table 2.
[0038]
[Table 2]

[0039]
As is clear from Table 2, as in Experimental Example 1, the acerola beverage of the present invention prepared by adding isochlorogenic acid was more light-irradiated and heat-treated than Comparative Product 3 to which chlorogenic acid was added. Fading was significantly suppressed and a clear red color was maintained. Although the fading phenomenon was suppressed at a high rate with respect to light, the fading phenomenon due to the heat treatment was suppressed almost completely. Anthocyanin dyes are known to be unstable to heat and light, particularly in the presence of ascorbic acid. From this experiment, isochlorogenic acid imparts heat resistance and light resistance to anthocyanin dyes (especially heat resistance). The effect was significantly higher than that of chlorogenic acid.
[0040]
Example 3 Fruit Jelly (Peach Jelly)
Fructose glucose liquid sugar (75%) 20.0
1/5 concentrated white peach juice 4.0
Carrageenan 1.0
Citric acid 0.2
Peach essence 0.1
Red cabbage pigment 0.1
Isochlorogenic acid 0.004
(Mixture of 3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid and 3,4,5-tricaffeoylquinic acid)
water Appropriate amount
Total 100.000
The above composition was added and mixed, heated and dissolved at 80 ° C. for 10 minutes, filled into a cup, cooled at 5 ° C. for 1 hour, and a fruit jelly was prepared.
[0041]
Example 4 Strawberry Sorbet Sugar 15.0
Powdered water tank 7.5
Hardened coconut oil 1.0
Nonfat dry milk 1.0
1/5 concentrated strawberry juice 4.0
Strawberry flavor 0.1
Grape juice pigment 0.22
Isochlorogenic acid 0.007
(Mixture of 3,4-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid)
water Appropriate amount
Total 100.000
Non-fat dry milk, sugar, powdered syrup, and fruit juice were used as the main ingredients, and isochlorogenic acid, hydrogenated coconut oil, and fragrance were added thereto to form a mixed solution, and grape juice pigment was added to and mixed with this mixed solution. Thereafter, the container was sterilized, cooled and frozen, filled into a container, cooled to 0 ° C. or lower, and frozen to prepare a strawberry sherbet.
[0042]
Example 5 Acerola gum gum base 100
Purified glucose 288.95
Powdered sugar 100
Citric acid 0.5
Acerola Laborer 5.0
Red radish pigment 1.0
Isochlorogenic acid 0.05
(Mixture of 3,5-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid)
water Appropriate amount
Total 500.00
In the above formulation, ingredients other than red radish pigment are mixed and heated to soften, then red radish pigment is added, kneaded to a suitable thickness with a rolling roller, cooled to room temperature, cut and acerola gum made.
[0043]
Example 6 A mixture of 20 g of hard candy water, 60 g of sugar, and 40 g of starch syrup was heated and dissolved to 150 ° C., boiled to 100 g, cooled to 120 ° C., 0.1 g of grape skin pigment, 0.5 g of citric acid, acerola 0.15 g of flavor and 0.008 g of isochlorogenic acid (4,5-dicaffeoylquinic acid) were added, and after molding, cooled to room temperature to make a hard candy.
[0044]
Example 7 Ume plum vinegar with strawberry flavor 42.0
Sugar 4.0
Fructose dextrose liquid sugar 20.0
Citric acid 1.0
Sodium glutamate 0.5
Skipjack extract 1.0
Purple corn pigment 0.3
Isochlorogenic acid 0.006
(Mixture of 3,5-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid)
Plum 50.0
water Appropriate amount
Total 150.00
The above-mentioned prescription was added and mixed to prepare a strawberry-flavored plum.
[0045]
Example 8 Plum dressing brewed vinegar 5.0
Sugar 3.0
Salt 2.6
Soy sauce 5.0
Apple cider vinegar 5.0
Lemon juice 3.0
Sodium glutamate 0.5
Comb extract 1.0
Skipjack extract 1.0
Plum meat 3.0
Perilla oil 0.05
Malic acid 0.4
Perilla dye 0.2
Isochlorogenic acid 0.008
(3,5-dicaffeoylquinic acid)
Corn salad oil 40.0
water Appropriate amount
Total 100.000
After various addition and mixing of the above components, sterilization, cooling, and filling into a container to prepare a plum dressing.

Claims (4)

  An anti-fading agent for anthocyanin dyes, comprising isochlorogenic acid or a salt thereof as an active ingredient.   Isochlorogenic acid is selected from the group consisting of 3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid and 3,4,5-tricaffeoylquinic acid The anti-fading agent for anthocyanin dyes according to claim 1, which is at least one of the above.   An anthocyanin dye fading prevention comprising the anthocyanin dye fading inhibitor according to claim 1 or 2 added to an anthocyanin dye-containing food, cosmetic, pharmaceutical, quasi-drug or feed. Method.   A method for preventing discoloration of an anthocyanin dye according to claim 1 or 2 in a food containing an anthocyanin dye, comprising the active ingredient of the discoloration preventive agent. The method of mix | blending a certain isochlorogenic acid in the ratio of 2-8 weight part with respect to 100 weight part of anthocyanin type pigment | dyes.