JP2004180535A - Method for decaffeinating caffein-containing catechin composition - Google Patents
Method for decaffeinating caffein-containing catechin composition Download PDFInfo
- Publication number
- JP2004180535A JP2004180535A JP2002348796A JP2002348796A JP2004180535A JP 2004180535 A JP2004180535 A JP 2004180535A JP 2002348796 A JP2002348796 A JP 2002348796A JP 2002348796 A JP2002348796 A JP 2002348796A JP 2004180535 A JP2004180535 A JP 2004180535A
- Authority
- JP
- Japan
- Prior art keywords
- caffeine
- composition
- catechin
- water
- caffein
- 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
Landscapes
- Tea And Coffee (AREA)
Abstract
Description
【０００１】
【発明の属する技術分野】
本発明はカフェイン含有カテキン類組成物から選択的にカフェインを除去する方法に関する。
【０００２】
【従来の技術】
カテキン類はコレステロール上昇抑制作用やα−アミラーゼ活性阻害作用などを有することが知られている（例えば、特許文献１、特許文献２参照）。カテキン類のこのような生理効果を発現させるには、成人一日あたり４〜５杯のお茶を飲むことが必要である。このため、より簡便に大量のカテキン類を摂取できるよう、飲料にカテキン類を高濃度に配合する技術が望まれている。
【０００３】
しかし、茶葉中にはカテキン類が約１５％含まれているものの、カフェイン成分も通常２〜４％含まれている。カフェインは中枢神経興奮作用を示すことから、眠気抑制に使用されている反面、過剰摂取による神経過敏、吐き気、不眠などの有害作用を引き起こす原因にもなるといわれている。このため、カフェイン含有組成物から、カフェインのみを選択的に除去する方法が検討されてきた。
【０００４】
例えば、コーヒーの脱カフェイン方法として、１２０〜２５０気圧下において、コーヒーを活性炭等のカフェイン吸着剤と接触させる方法（特許文献３）や、カフェインを含有する水溶液を活性白土または酸性白土と接触させることにより選択的にカフェインを除去する方法（特許文献４）が提案されている。
【０００５】
しかしながら、前者は超臨界抽出技術に関するものであり、プロセス上の設備負荷が過大で工業レベルでの実施において簡易性に欠ける。また、この方法はカフェインのみを選択的に除去するのではなく、有効成分であるカテキン類組成も変化させてしまうという問題がある。一方、後者の方法は、活性白土または酸性白土を使用するだけで選択的にカフェインを除去できるが、色相が悪化する場合があるなどの問題もあった。
【０００６】
【特許文献１】
特開昭６０−１５６６１４号公報
【特許文献２】
特開平３−１３３９２８号公報
【特許文献３】
特開昭５３−１８７７２号公報
【特許文献４】
特開平６−１４２４０５号公報
【０００７】
【発明が解決しようとする課題】
本発明の目的は、カフェイン含有カテキン類組成物中のカフェインを、カテキン類組成を著しく変化させることなく、選択的に除去する方法を提供することにある。
【０００８】
【課題を解決するための手段】
本発明者は、カテキン類組成物に含まれるカフェインを、特定の割合の水と有機溶媒の混合溶液中に溶解させた状態で、活性炭と接触させることにより、カテキン類組成を著しく変化させることなく、しかも色相を悪化させずに、選択的にカフェインを除去できることを見出した。
【０００９】
本発明は、カフェイン含有カテキン類組成物を、有機溶媒と水の重量比が９／１〜１／９の混合溶液に溶解させ、活性炭と接触させることを特徴とする、カフェイン含有カテキン類組成物から選択的にカフェインを除去する方法を提供するものである。
【００１０】
また、本発明は、カフェイン含有カテキン類組成物を、有機溶媒と水の重量比が９／１〜１／９の混合溶液に溶解させ、活性炭と接触させることを特徴とする、カフェイン濃度が、非重合体カテキン類に対して、非重合体カテキン類／カフェイン比率１０〜３０である緑茶抽出物の製造方法を提供するものである。
【００１１】
【発明の実施の形態】
本発明で用いるカフェイン含有カテキン類組成物は、非重合体カテキン類を１種以上含有するものである。非重合体カテキン類とは、カテキン、ガロカテキン、カテキンガレート、ガロカテキンガレート等の非エピ体カテキン類及びエピカテキン、エピガロカテキン、エピカテキンガレート、エピガロカテキンガレート等のエピ体カテキン類をあわせての総称である。
【００１２】
このような非重合体カテキン類を含有するカフェイン含有カテキン類組成物としては、緑茶、紅茶、烏龍茶等の茶葉から得られた抽出液が挙げられる。その他のカフェイン含有植物由来、例えばコーヒーなどのカフェインと茶抽出液の混合物なども用いることができる。
【００１３】
ここで使用する茶葉は、より具体的には、Ｃａｍｅｌｌｉａ属、例えばＣ． ｓｉｎｅｎｓｉｓ、Ｃ． ａｓｓａｍｉｃａ、及びやぶきた種、又はそれらの雑種等から得られる茶葉から製茶された茶葉が挙げられる。製茶された茶葉には、煎茶、番茶、玉露、てん茶、釜炒り茶等の緑茶類がある。
茶葉からカフェイン含有カテキン類組成物の抽出は、攪拌抽出等の方法により行うことができる。抽出の際、水にあらかじめアスコルビン酸ナトリウム等の有機酸又は有機酸塩類を添加しても良い。また、煮沸脱気や窒素ガス等の不活性ガスを通気して溶存酸素を除去しつつ、いわゆる非酸化的雰囲気下で抽出する方法を併用してもよい。
【００１４】
茶葉から抽出するかわりに、茶抽出物の濃縮物を水に溶解あるいは希釈して用いても、茶葉からの抽出液と茶抽出物の濃縮物とを併用しても良い。
ここで、茶抽出物の濃縮物とは、茶葉から熱水又は水溶性有機溶媒により抽出された抽出物を濃縮したものであり、例えば、特開昭５９−２１９３８４号公報、特開平４−２０５８９号公報、特開平５−２６０９０７号公報、特開平５−３０６２７９号公報等に記載されている方法により調製したものをいう。
カフェイン含有カテキン類組成物としては、乾燥重量で、非重合体カテキン類を２５〜９０重量％、特に２５〜７０重量％、更に２５〜４０重量％含有する緑茶抽出物を用いるのが、非重合体カテキン類以外の呈味成分が残っているために好ましい。
【００１５】
具体的には、市販の東京フードテクノ社製「ポリフェノン」、伊藤園社製「テアフラン」、太陽化学社製「サンフェノン」などの粗カテキン製剤を用いることもできる。
【００１６】
本発明で用いる有機溶媒としては、エタノール、メタノール、アセトン、酢酸エチル等が挙げられる。これらのうち、エタノール、メタノール、アセトンの親水性有機溶媒が好ましく、特に食品への使用を考慮すると、エタノールが好ましい。
【００１７】
本発明においては、有機溶媒と水の重量比を９／１〜１／９、好ましくは９／１〜５／５、より好ましくは８／２〜６／４の範囲に調整することが必要である。有機溶媒の割合が９／１を超えるとカテキン類の抽出効率が落ちてしまい、また１／９未満では、脱カフェイン品の味の改善効果が不十分となる。
【００１８】
カフェイン含有カテキン類組成物を有機溶媒と水の混合溶液に溶解する方法は特に制限されず、カフェイン含有カテキン類組成物を水に溶解した後に有機溶媒を添加していくことによって有機溶媒と水の重量比を９／１〜１／９の範囲にしても良く、カフェイン含有カテキン類組成物を有機溶媒に懸濁させた後、徐々に水を添加して同様の比率としても良い。抽出効率の点から、水に溶解後に有機溶媒を添加していく方法が好ましい。カフェイン含有カテキン類組成物を処理する場合において、水のみでの処理ではカテキン類が活性炭に吸着されてしまうのに対し、有機溶媒の存在においてこの影響を排除できる。
【００１９】
本発明においては、有機溶媒と水の混合溶液１００重量部に対して、カフェイン含有カテキン類組成物１０〜４０重量部、特に１５〜３０重量部添加して処理するのが、カフェイン含有カテキン類組成物を効率良く処理できるので好ましい。
【００２０】
水または有機溶媒の必要量の添加時間は１０〜３０分程度の時間でゆっくり滴下するのが好ましい。また、カテキン類の抽出効率を上げるために攪拌状態で滴下するのが好ましい。水の滴下終了後は１０〜１２０分程度の熟成時間を設けると更に好ましい。
これらの処理は、１０〜６０℃で行うことができ、特に１０〜５０℃、更に１０〜４０℃で行うのが好ましい。
【００２１】
本発明で用いる活性炭としては、一般に工業レベルで使用されているものであれば特に制限されず、例えば、ＺＮ−５０（北越炭素社製）、クラレコールＧＬＣ、クラレコールＰＫ−Ｄ、クラレコールＰＷ−Ｄ（クラレケミカル社製）、白鷲ＡＷ５０、白鷲Ａ、白鷲Ｍ、白鷲Ｃ（武田薬品工業社製）などの市販品を用いることができる。
活性炭の細孔容積は０．０１〜０．８ｍＬ／ｇが好ましく、特に０．１〜０．７ｍＬ／ｇが好ましい。また、比表面積は８００〜１３００ｍ２／ｇ、特に９００〜１２００ｍ２／ｇの範囲のものが好ましい。なお、これらの物性値は窒素吸着法に基づく値である。
【００２２】
活性炭は、有機溶媒と水の混合溶液１００重量部に対して０．５〜５重量部、特に０．５〜３重量部添加するのが好ましい。活性炭の添加量が少なすぎると、カフェイン除去効率が悪くなり、また多すぎるとろ過工程におけるケーク抵抗が大きくなり好ましくない。
【００２３】
カフェイン含有カテキン類組成物と活性炭の接触処理は、バッチ式、カラムによる連続処理等のいずれの方法で行っても良い。一般には、粉末状の活性炭を添加、攪拌し、カフェインを選択的に吸着後、ろ過操作によりカフェインを除去した濾液を得る方法、あるいは顆粒状の活性炭を充填したカラムを用いて連続処理によりカフェインを選択的に吸着する方法が採用される。
活性炭と接触させた後のカテキン類組成物を含有する溶液は、系中から有機溶媒を取り除くべく減圧蒸留などの方法を用いて留去される。また処理後のカテキン類組成物は液状でも固体状でもいずれでも良いが、固体状に調製する場合には、凍結乾燥やスプレードライなどの方法によって粉末化しても良い。
【００２４】
本発明により脱カフェイン処理を行った後のカテキン類組成物は、含有する非重合体カテキン類の組成が処理前と本質的に変化していないのが好ましい。処理前後の有機溶媒と水の混合溶液中の非重合体カテキン類の収率は７０重量％以上が好ましく、特に８０重量％以上が好ましい。
本発明による脱カフェイン処理後のカテキン類組成物中のカフェイン濃度は、非重合体カテキン類に対して、非重合体カテキン類／カフェイン比が、１０〜３０、更に１０〜２５、特に１０〜２０であるのが好ましい。１０未満では、カフェインの呈味の影響が大きく飲用に適さない。また、３０以上では、ろ過工程の効率の観点から好ましくない。
【００２５】
また、本発明により脱カフェイン処理を行った後のカテキン類組成物中の非重合体カテキン類は、エピガロカテキンガレート、ガロカテキンガレート、エピガロカテキン及びガロカテキンからなるガロ体と、エピカテキンガレート、カテキンガレート、エピカテキン及びカテキンからなる非ガロ体の比率が、天然の緑茶葉の組成を維持しているのが好ましい。すなわち、上記４種のガロ体総量は常に上記４種の非ガロ体総量を上回っているのが、精製物においても天然の緑茶葉の組成を維持しているという点において好ましい。
【００２６】
また、本発明による脱カフェイン処理後のカテキン類組成物中のカテキンガレート、エピカテキンガレート、ガロカテキンガレート及びエピガロカテキンガレートからなるガレート体の全非重合体カテキン類中での割合は、４５重量％以上であるのが、非重合体カテキン類の生理効果の有効性上好ましい。
【００２７】
【実施例】
カテキン類の測定
カフェイン含有カテキン類組成物を蒸留水で希釈し、フィルター（０．８μｍ）でろ過後、島津製作所社製、高速液体クロマトグラフ（型式ＳＣＬ−１０ＡＶＰ）を用い、オクタデシル基導入液体クロマトグラフ用パックドカラム Ｌ−カラムＴＭ ＯＤＳ（４．６ｍｍφ×２５０ｍｍ：財団法人 化学物質評価研究機構製）を装着し、カラム温度３５℃で、Ａ液及びＢ液を用いたグラジエント法により行った。移動相Ａ液は酢酸を０．１ｍｏｌ／Ｌ含有の蒸留水溶液、Ｂ液は酢酸を０．１ｍｏｌ／Ｌ含有のアセトニトリル溶液とし、試料注入量は２０μＬ、ＵＶ検出器波長は２８０ｎｍの条件で行った。
【００２８】
カフェインの測定
（分析機器）
ＨＰＬＣ（日立製作所社製）装置を使用。
プロッター：Ｄ−２５００，ディティクター：Ｌ−４２００
ポンプ：Ｌ−７１００，オートサンプラー：Ｌ−７２００
カラム：ｌｎｅｒｔｓｉｌ ＯＤＳ−２、内径２．１ｍｍ×長さ２５０ｍｍ
（分析条件）
サンプル注入量：１０μＬ，流量：１．０ｍＬ／ｍｉｎ
紫外線吸光光度計検出波長：２８０ｎｍ
カフェイン：２７．２分
ここで求めたエリア％から標準物質により重量％を求めた。
【００２９】
色相の評価（吸光度）
（分析機器）
ＵＶ ＭＩＮＩ１２４０（島津製作所社製）装置を使用。
分光光度計で４５０ｎｍの吸光度における値を測定した。測定においては、精製後のカテキン類組成物をカテキン濃度１００ｍｇ％になるようにイオン交換水で希釈し、そのサンプルを用いて吸光度を測定した。
【００３０】
実施例１、比較例１〜２
表１に示す条件により、カフェイン含有カテキン類組成物中のカフェインの除去処理を行った。
なお、用いたカフェイン含有カテキン類組成物（ポリフェノンＨＧ、東京フードテクノ社製）は、非重合体カテキン類含有量３３．７０重量％、カフェイン含有量５．５重量％、非重合体カテキン類／カフェイン＝６．１、ガレート体率５０．７重量％である。
【００３１】
（処理方法）
（１）実施例１：
カフェイン含有カテキン類組成物（ポリフェノンＨＧ、東京フードテクノ社製）１００ｇを常温、２５０ｒｐｍ攪拌条件下の９５％エタノール水溶液４９０．９ｇ中に懸濁させ、活性炭（クラレコールＧＬＣ、クラレケミカル社製）２０ｇを投入後、約１０分間攪拌を続けた。そして４０％エタノール水溶液４０９．１ｇを１０分間かけて滴下したのち、室温のまま約３０分間の攪拌処理を続けた。その後、２号濾紙で活性炭及び沈殿物を濾過したのち、０．２μｍメンブランフィルターによって再濾過を行った。最後にイオン交換水２００ｇを濾過液に添加し、４０℃、２５Ｔｏｒｒでエタノールを留去し、製品を得た。
【００３２】
（２）比較例１：
活性炭を添加しない以外は実施例１と同様に行った。
（３）比較例２：
カフェイン含有カテキン類組成物（ポリフェノンＨＧ、東京フードテクノ社製）１００ｇを常温、２５０ｒｐｍ攪拌条件下の水９００ｇ中に懸濁させ、活性炭（クラレコールＧＬＣ、クラレケミカル社製）２０ｇを投入後、約２０分間攪拌を続けた。その後、室温のまま約３０分間の攪拌処理を続けた。次に、２号濾紙で濾過したのち、０．２μｍメンブランフィルターによって再濾過を行った。最後に実施例１と同等の水分量になるまで、乾燥機で徐々に水分を蒸発させ、製品を得た。
【００３３】
【表１】
表１の結果から明らかなように、本発明によりカフェイン含有カテキン類組成物を処理することにより、カテキン類組成を維持したまま、カフェインを選択的に除去し、色相を改良させたカテキン類組成物を得ることができる。
【００３５】
【発明の効果】
本発明によれば、カフェイン含有カテキン類組成物中のカフェインを、カテキン類組成を著しく変化させることなく、しかも色相を悪化させずに、選択的に除去することができる。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a method for selectively removing caffeine from a caffeine-containing catechin composition.
[0002]
[Prior art]
It is known that catechins have a cholesterol increase inhibitory action and an α-amylase activity inhibitory action (for example, see Patent Documents 1 and 2). In order for catechins to exert such physiological effects, it is necessary to drink 4 to 5 cups of tea per adult day. For this reason, a technique for blending catechins in a beverage at a high concentration is desired so that a large amount of catechins can be ingested more easily.
[0003]
However, although tea leaves contain about 15% of catechins, caffeine components usually contain 2 to 4%. Since caffeine has a central nervous system excitatory effect, it is used to suppress drowsiness, but is also considered to cause adverse effects such as nervousness, nausea, and insomnia due to excessive intake. For this reason, a method for selectively removing only caffeine from a caffeine-containing composition has been studied.
[0004]
For example, as a method for decaffeinating coffee, a method in which coffee is contacted with a caffeine adsorbent such as activated carbon at 120 to 250 atm (Patent Document 3), or an aqueous solution containing caffeine is mixed with activated clay or acid clay. A method of selectively removing caffeine by contact has been proposed (Patent Document 4).
[0005]
However, the former relates to the supercritical extraction technology, and the facility load on the process is excessive, and the practicability at the industrial level is lacking. In addition, this method has a problem that not only the selective removal of caffeine but also the composition of catechins as an active ingredient is changed. On the other hand, the latter method can selectively remove caffeine only by using activated clay or acid clay, but has a problem that the hue may be deteriorated.
[0006]
[Patent Document 1]
JP-A-60-156614 [Patent Document 2]
Japanese Patent Application Laid-Open No. 3-13928 [Patent Document 3]
JP-A-53-18772 [Patent Document 4]
JP-A-6-142405
[Problems to be solved by the invention]
An object of the present invention is to provide a method for selectively removing caffeine in a caffeine-containing catechin composition without significantly changing the catechin composition.
[0008]
[Means for Solving the Problems]
The present inventors have found that caffeine contained in a catechin composition is dissolved in a mixed solution of water and an organic solvent at a specific ratio, and then brought into contact with activated carbon to significantly change the catechin composition. And found that caffeine can be selectively removed without deteriorating the hue.
[0009]
The present invention provides a caffeine-containing catechin, comprising dissolving a caffeine-containing catechin composition in a mixed solution of an organic solvent and water at a weight ratio of 9/1 to 1/9, and contacting the solution with activated carbon. Provided is a method for selectively removing caffeine from a composition.
[0010]
The present invention also provides a caffeine-containing catechin composition, which is dissolved in a mixed solution of an organic solvent and water at a weight ratio of 9/1 to 1/9, and brought into contact with activated carbon. Provides a method for producing a green tea extract having a non-polymer catechins / caffeine ratio of 10 to 30 with respect to the non-polymer catechins.
[0011]
BEST MODE FOR CARRYING OUT THE INVENTION
The caffeine-containing catechin composition used in the present invention contains one or more non-polymer catechins. Non-polymer catechins, catechin, gallocatechin, catechin gallate, non-epicate catechins such as gallocatechin gallate and epicatechin, epigallocatechin, epicatechin gallate, epigate catechins such as epigallocatechin gallate together Is a generic term for
[0012]
Examples of the caffeine-containing catechin composition containing such non-polymer catechins include extracts obtained from tea leaves such as green tea, black tea, and oolong tea. Other caffeine-containing plant-derived materials, for example, a mixture of caffeine such as coffee and a tea extract can also be used.
[0013]
More specifically, the tea leaves used herein are of the genus Camellia, for example, C. elegans. sinensis, C.I. tea leaves produced from tea leaves obtained from assamica and Yabutaki seeds or hybrids thereof. The tea leaves made include green teas such as sencha, bancha, gyokuro, tencha, and pot roasted tea.
The extraction of the caffeine-containing catechin composition from tea leaves can be performed by a method such as stirring extraction. At the time of extraction, an organic acid or an organic acid salt such as sodium ascorbate may be added to water in advance. Further, a method of extracting under a so-called non-oxidizing atmosphere while removing dissolved oxygen by boiling degassing or passing an inert gas such as nitrogen gas may be used in combination.
[0014]
Instead of extracting from tea leaves, a concentrate of tea extract may be dissolved or diluted in water and used, or an extract from tea leaves and a concentrate of tea extract may be used in combination.
Here, the concentrate of the tea extract is a concentrate obtained by extracting an extract extracted from tea leaves with hot water or a water-soluble organic solvent. For example, JP-A-59-219384 and JP-A-4-20589. And those prepared by the methods described in JP-A-5-260907, JP-A-5-306279 and the like.
As a caffeine-containing catechin composition, it is preferable to use a green tea extract containing 25 to 90% by weight, particularly 25 to 70% by weight, and further 25 to 40% by weight of a non-polymer catechin by dry weight. This is preferable because taste components other than polymer catechins remain.
[0015]
Specifically, crude catechin preparations such as commercially available "Polyphenon" manufactured by Tokyo Food Techno Co., "Theafuran" manufactured by ITO EN, and "Sanphenone" manufactured by Taiyo Kagaku can also be used.
[0016]
Examples of the organic solvent used in the present invention include ethanol, methanol, acetone, and ethyl acetate. Among these, hydrophilic organic solvents such as ethanol, methanol and acetone are preferred, and ethanol is particularly preferred in view of use in foods.
[0017]
In the present invention, it is necessary to adjust the weight ratio of the organic solvent and water to 9/1 to 1/9, preferably 9/1 to 5/5, and more preferably 8/2 to 6/4. is there. When the ratio of the organic solvent exceeds 9/1, the extraction efficiency of catechins decreases, and when it is less than 1/9, the effect of improving the taste of the decaffeinated product becomes insufficient.
[0018]
The method of dissolving the caffeine-containing catechin composition in a mixed solution of an organic solvent and water is not particularly limited, and the organic solvent is added by dissolving the caffeine-containing catechin composition in water and then adding the organic solvent. The weight ratio of water may be in the range of 9/1 to 1/9, and after the caffeine-containing catechins composition is suspended in the organic solvent, water may be gradually added to make the same ratio. From the viewpoint of extraction efficiency, a method of adding an organic solvent after dissolving in water is preferable. In the case of treating a caffeine-containing catechin composition, catechins are adsorbed on activated carbon by treatment with water alone, whereas this effect can be eliminated in the presence of an organic solvent.
[0019]
In the present invention, caffeine-containing catechin is treated by adding 10 to 40 parts by weight, particularly 15 to 30 parts by weight, of a caffeine-containing catechin composition to 100 parts by weight of a mixed solution of an organic solvent and water. This is preferable because the composition can be efficiently treated.
[0020]
It is preferable that the addition time of the required amount of water or the organic solvent is slowly dropped in about 10 to 30 minutes. Further, it is preferable to drop the mixture in a stirring state in order to increase the extraction efficiency of catechins. It is more preferable to provide an aging time of about 10 to 120 minutes after completion of the dropping of water.
These treatments can be performed at 10 to 60 ° C, particularly preferably at 10 to 50 ° C, more preferably at 10 to 40 ° C.
[0021]
The activated carbon used in the present invention is not particularly limited as long as it is generally used at an industrial level. For example, ZN-50 (manufactured by Hokuetsu Carbon Co., Ltd.), Kuraray Coal GLC, Kuraray Coal PK-D, Kuraray Coal PW Commercial products such as -D (Kuraray Chemical Co., Ltd.), Hakuseki AW50, Hakuseki A, Hakuseki M, Hakusagi C (Takeda Pharmaceutical Co., Ltd.) can be used.
The pore volume of the activated carbon is preferably from 0.01 to 0.8 mL / g, particularly preferably from 0.1 to 0.7 mL / g. Further, the specific surface area is preferably in the range of 800 to 1300 m 2 / g, particularly preferably in the range of 900 to 1200 m 2 / g. These physical properties are values based on the nitrogen adsorption method.
[0022]
Activated carbon is preferably added in an amount of 0.5 to 5 parts by weight, particularly 0.5 to 3 parts by weight, per 100 parts by weight of the mixed solution of the organic solvent and water. If the added amount of the activated carbon is too small, the caffeine removal efficiency will be poor, and if it is too large, the cake resistance in the filtration step will be undesirably large.
[0023]
The contact treatment between the caffeine-containing catechin composition and the activated carbon may be performed by any method such as a batch method or a continuous treatment using a column. Generally, powdered activated carbon is added and stirred, and after selectively adsorbing caffeine, a method of obtaining a filtrate from which caffeine has been removed by a filtration operation, or by continuous treatment using a column filled with granular activated carbon A method of selectively adsorbing caffeine is employed.
The solution containing the catechins composition after being brought into contact with activated carbon is distilled off using a method such as vacuum distillation to remove the organic solvent from the system. The catechins composition after the treatment may be either liquid or solid, but when prepared in a solid form, it may be powdered by a method such as freeze-drying or spray-drying.
[0024]
It is preferable that the composition of the non-polymer catechins contained in the catechin composition after the decaffeination treatment according to the present invention is essentially unchanged from that before the treatment. The yield of the non-polymer catechins in the mixed solution of the organic solvent and water before and after the treatment is preferably 70% by weight or more, particularly preferably 80% by weight or more.
The caffeine concentration in the catechin composition after the decaffeination treatment according to the present invention is such that the ratio of the non-polymer catechins / caffeine to the non-polymer catechins is 10 to 30, more preferably 10 to 25, particularly 10 to 25. It is preferably from 10 to 20. If it is less than 10, the influence of the taste of caffeine is large and it is not suitable for drinking. Further, if it is 30 or more, it is not preferable from the viewpoint of the efficiency of the filtration step.
[0025]
Further, non-polymer catechins in the catechins composition after decaffeination treatment according to the present invention, epigallocatechin gallate, gallocatechin gallate, gallo body consisting of epigallocatechin and gallocatechin, epicatechin gallate It is preferable that the ratio of the non-gallo form composed of catechin gallate, epicatechin and catechin maintains the composition of natural green tea leaves. That is, it is preferable that the total amount of the four types of Galo bodies always exceeds the total amount of the four types of non-Gallo bodies, since the composition of natural green tea leaves is maintained even in the purified product.
[0026]
In the catechin composition after decaffeination treatment according to the present invention, the ratio of the catechin gallate, epicatechin gallate, gallocatechin gallate and the gallate composed of epigallocatechin gallate in the total non-polymer catechins is 45%. It is preferable that the content is not less than% by weight in terms of the effectiveness of the physiological effect of the non-polymer catechins.
[0027]
【Example】
Measurement of catechins The caffeine-containing catechins composition was diluted with distilled water, filtered with a filter (0.8 μm), and then using a high-performance liquid chromatograph (model SCL-10AVP) manufactured by Shimadzu Corporation. Gradient method using liquid A and liquid B at a column temperature of 35 ° C. equipped with a packed column L-column TM ODS (4.6 mmφ × 250 mm: manufactured by Japan Chemicals Evaluation and Research Organization) for an octadecyl group-introduced liquid chromatograph. It was performed by. The mobile phase A liquid was a distilled aqueous solution containing 0.1 mol / L of acetic acid, and the liquid B was an acetonitrile solution containing 0.1 mol / L of acetic acid. The sample injection amount was 20 μL, and the UV detector wavelength was 280 nm. .
[0028]
Caffeine measurement (analytical equipment)
Using an HPLC (Hitachi Ltd.) device.
Plotter: D-2500, Detector: L-4200
Pump: L-7100, Autosampler: L-7200
Column: lertsil ODS-2, inner diameter 2.1 mm x length 250 mm
(Analysis conditions)
Sample injection volume: 10 μL, flow rate: 1.0 mL / min
UV absorption spectrophotometer detection wavelength: 280 nm
Caffeine: 27.2 minutes Weight% was determined from the area% determined here using a standard substance.
[0029]
Hue evaluation (absorbance)
(Analytical instruments)
Uses UV MINI1240 (manufactured by Shimadzu Corporation).
The value at an absorbance of 450 nm was measured with a spectrophotometer. In the measurement, the purified catechin composition was diluted with ion-exchanged water so as to have a catechin concentration of 100 mg%, and the absorbance was measured using the sample.
[0030]
Example 1, Comparative Examples 1-2
Under the conditions shown in Table 1, a treatment for removing caffeine in the caffeine-containing catechin composition was performed.
The caffeine-containing catechin composition (Polyphenone HG, manufactured by Tokyo Food Techno Co., Ltd.) used had a non-polymer catechin content of 33.70% by weight, a caffeine content of 5.5% by weight, and a non-polymer catechin. Class / caffeine = 6.1, gallate content 50.7% by weight.
[0031]
(Processing method)
(1) Example 1
100 g of a caffeine-containing catechin composition (Polyphenone HG, manufactured by Tokyo Food Techno Co., Ltd.) was suspended in 490.9 g of a 95% aqueous ethanol solution at room temperature and 250 rpm with stirring, and activated carbon (Kuraray Coal GLC, manufactured by Kuraray Chemical Co., Ltd.) After charging 20 g, stirring was continued for about 10 minutes. Then, after 409.1 g of a 40% aqueous ethanol solution was added dropwise over 10 minutes, the stirring treatment was continued for about 30 minutes at room temperature. Thereafter, the activated carbon and the precipitate were filtered through No. 2 filter paper, and then re-filtered through a 0.2 μm membrane filter. Finally, 200 g of ion-exchanged water was added to the filtrate, and ethanol was distilled off at 40 ° C. and 25 Torr to obtain a product.
[0032]
(2) Comparative Example 1:
The procedure was performed in the same manner as in Example 1 except that no activated carbon was added.
(3) Comparative Example 2:
100 g of a caffeine-containing catechin composition (Polyphenone HG, manufactured by Tokyo Food Techno Co., Ltd.) was suspended in 900 g of water at 250 ° C. with stirring at room temperature, and 20 g of activated carbon (Kuraray Coal GLC, manufactured by Kuraray Chemical Co., Ltd.) was added. Stirring was continued for about 20 minutes. Thereafter, the stirring treatment was continued for about 30 minutes at room temperature. Next, after filtration through No. 2 filter paper, re-filtration was performed with a 0.2 μm membrane filter. Finally, water was gradually evaporated using a dryer until the water content became equal to that of Example 1, thereby obtaining a product.
[0033]
[Table 1]
As is clear from the results in Table 1, by treating the catechin-containing catechin composition according to the present invention, caffeine is selectively removed and the hue is improved while maintaining the catechin composition. A composition can be obtained.
[0035]
【The invention's effect】
According to the present invention, caffeine in a caffeine-containing catechin composition can be selectively removed without significantly changing the catechin composition and without deteriorating the hue.
Claims (2)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002348796A JP4181863B2 (en) | 2002-11-29 | 2002-11-29 | Caffeine-containing catechin composition decaffeination method |
| AU2003275679A AU2003275679A1 (en) | 2002-10-28 | 2003-10-27 | Method of removing caffeine from caffeine-containing catechin compound composition |
| CN2006101695003A CN1981586B (en) | 2002-10-28 | 2003-10-27 | Method for purifying condensate of tea extraction compound |
| EP11173762.3A EP2382876B1 (en) | 2002-10-28 | 2003-10-27 | Method of purifying a solid concentrate of a tea extract. |
| PCT/JP2003/013700 WO2004037022A1 (en) | 2002-10-28 | 2003-10-27 | Method of removing caffeine from caffeine-containing catechin compound composition |
| KR1020057005930A KR101049391B1 (en) | 2002-10-28 | 2003-10-27 | Decaffeine Method of Caffeine-Containing Catechin Compositions |
| EP11173763.1A EP2382877B8 (en) | 2002-10-28 | 2003-10-27 | Green tea extract |
| EP03758933.0A EP1557097B1 (en) | 2002-10-28 | 2003-10-27 | Method of removing caffeine from caffeine-containing catechin compound composition |
| US10/532,727 US7883734B2 (en) | 2002-10-28 | 2003-10-27 | Method of removing caffeine from caffeine-containing catechin compound composition |
| EP13178703.8A EP2659791B1 (en) | 2002-10-28 | 2003-10-27 | Caffeine-containing catechin compound composition |
| TW099122034A TW201038206A (en) | 2002-10-28 | 2003-10-28 | Method of removing caffeine from caffeine-containing catechin compound composition |
| TW092129912A TW200418395A (en) | 2002-10-28 | 2003-10-28 | Method of removing caffeine from caffeine-containing catechin compound composition |
| US12/971,555 US8574655B2 (en) | 2002-10-28 | 2010-12-17 | Packaged beverage with caffeine-containing catechin composition |
| US14/029,259 US9198946B2 (en) | 2002-10-28 | 2013-09-17 | Green tea extract |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002348796A JP4181863B2 (en) | 2002-11-29 | 2002-11-29 | Caffeine-containing catechin composition decaffeination method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004180535A true JP2004180535A (en) | 2004-07-02 |
| JP4181863B2 JP4181863B2 (en) | 2008-11-19 |
Family
ID=32751610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002348796A Expired - Fee Related JP4181863B2 (en) | 2002-10-28 | 2002-11-29 | Caffeine-containing catechin composition decaffeination method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4181863B2 (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006063004A (en) * | 2004-08-26 | 2006-03-09 | Kao Corp | Method for producing catechins-containing composition |
| JP2006129757A (en) * | 2004-11-04 | 2006-05-25 | Pharma Foods International Co Ltd | Green tea extract reduced in bitter taste and harsh taste, and drink and food containing the extract |
| JP2007001893A (en) * | 2005-06-22 | 2007-01-11 | Ito En Ltd | Catechin composition and method for production of the same |
| JP2007014283A (en) * | 2005-07-08 | 2007-01-25 | Kao Corp | Packaged green tea beverage |
| JP2007022935A (en) * | 2005-07-13 | 2007-02-01 | Kao Corp | Method for producing non-polymer catechin composition |
| EP1810575A1 (en) | 2006-01-23 | 2007-07-25 | Ito En, Ltd. | Beverage |
| WO2007122817A1 (en) * | 2006-04-17 | 2007-11-01 | Kao Corporation | Process for producing purified green tea extract |
| WO2007122818A1 (en) * | 2006-04-17 | 2007-11-01 | Kao Corporation | Process for producing purified green tea extract |
| JP2008212024A (en) * | 2007-03-01 | 2008-09-18 | Riverson:Kk | Tea reduced in caffeine content, and method for producing the same |
| JP2008280282A (en) * | 2007-05-10 | 2008-11-20 | Ogawa & Co Ltd | Purification method of polyphenol-containing composition, and polyphenol-containing composition purified by the same |
| US7666452B2 (en) | 2006-01-25 | 2010-02-23 | Ito En, Ltd. | Beverage comprising cathechins and caffeine |
| JP2011004766A (en) * | 2010-10-08 | 2011-01-13 | Kao Corp | Method for producing decaffeinated raw coffee bean extract |
| CN101019586B (en) * | 2006-02-14 | 2012-09-05 | 株式会社伊藤园 | Beverage |
| JP2013539788A (en) * | 2010-10-13 | 2013-10-28 | クラフト・フーヅ・グローバル・ブランヅ リミテッド ライアビリティ カンパニー | Coffee extract as a material for food, pharmaceuticals, cosmetics, dietary supplements, and biopharmaceuticals |
| JP2014124141A (en) * | 2012-12-26 | 2014-07-07 | Asahi Soft Drinks Co Ltd | Tea beverage and method for increasing the deliciousness of tea beverage |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59219384A (en) * | 1983-05-30 | 1984-12-10 | Mitsui Norin Kk | Preparation of natural antioxidant |
| JPH0145345B2 (en) * | 1980-05-28 | 1989-10-03 | Nestle Sa | |
| JPH0222755B2 (en) * | 1983-07-05 | 1990-05-21 | Mitsui Norin Kk | |
| JPH0420589A (en) * | 1990-05-16 | 1992-01-24 | Mitsui Norin Kk | Manufacture of green tea polyphenol |
| JPH04300836A (en) * | 1991-03-29 | 1992-10-23 | Nikko Kyodo Co Ltd | Hepatic dysfunction preventive agent and functional food having preventive action on hepatic dysfunction |
| JPH04352726A (en) * | 1990-08-17 | 1992-12-07 | Nikko Kyodo Co Ltd | Arterial sclerosis-preventing agent and functional food having arterial sclerosis-preventing activity |
| JPH07179353A (en) * | 1993-12-22 | 1995-07-18 | Mitsui Norin Kk | Production of tea polyphenol containing low caffeine |
| JPH07313062A (en) * | 1994-05-23 | 1995-12-05 | Unie Kafue:Kk | Method for obtaining caffeine-reduced coffee extract, method for obtaining coffee beverage from the same, method for obtaining instant coffee from the same, and method for obtaining concentrated solution of coffee extract from the same |
| JPH0870772A (en) * | 1994-09-05 | 1996-03-19 | Unie Cafe:Kk | Caffeine reduced production of tea leaf extract, tea beverage and concentrate of tea extract; drying and utilization of tea extract, production of tea beverage, solid material and concentrate of tea beverage reduced in strange smell caused in tea leaf processing and caffeine content and extraction of tea reduced in caffeine content by soaking tea bag in water |
-
2002
- 2002-11-29 JP JP2002348796A patent/JP4181863B2/en not_active Expired - Fee Related
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0145345B2 (en) * | 1980-05-28 | 1989-10-03 | Nestle Sa | |
| JPS59219384A (en) * | 1983-05-30 | 1984-12-10 | Mitsui Norin Kk | Preparation of natural antioxidant |
| JPH0222755B2 (en) * | 1983-07-05 | 1990-05-21 | Mitsui Norin Kk | |
| JPH0420589A (en) * | 1990-05-16 | 1992-01-24 | Mitsui Norin Kk | Manufacture of green tea polyphenol |
| JPH04352726A (en) * | 1990-08-17 | 1992-12-07 | Nikko Kyodo Co Ltd | Arterial sclerosis-preventing agent and functional food having arterial sclerosis-preventing activity |
| JPH04300836A (en) * | 1991-03-29 | 1992-10-23 | Nikko Kyodo Co Ltd | Hepatic dysfunction preventive agent and functional food having preventive action on hepatic dysfunction |
| JPH07179353A (en) * | 1993-12-22 | 1995-07-18 | Mitsui Norin Kk | Production of tea polyphenol containing low caffeine |
| JPH07313062A (en) * | 1994-05-23 | 1995-12-05 | Unie Kafue:Kk | Method for obtaining caffeine-reduced coffee extract, method for obtaining coffee beverage from the same, method for obtaining instant coffee from the same, and method for obtaining concentrated solution of coffee extract from the same |
| JPH0870772A (en) * | 1994-09-05 | 1996-03-19 | Unie Cafe:Kk | Caffeine reduced production of tea leaf extract, tea beverage and concentrate of tea extract; drying and utilization of tea extract, production of tea beverage, solid material and concentrate of tea beverage reduced in strange smell caused in tea leaf processing and caffeine content and extraction of tea reduced in caffeine content by soaking tea bag in water |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006063004A (en) * | 2004-08-26 | 2006-03-09 | Kao Corp | Method for producing catechins-containing composition |
| JP2006129757A (en) * | 2004-11-04 | 2006-05-25 | Pharma Foods International Co Ltd | Green tea extract reduced in bitter taste and harsh taste, and drink and food containing the extract |
| JP2007001893A (en) * | 2005-06-22 | 2007-01-11 | Ito En Ltd | Catechin composition and method for production of the same |
| JP2007014283A (en) * | 2005-07-08 | 2007-01-25 | Kao Corp | Packaged green tea beverage |
| JP4644058B2 (en) * | 2005-07-08 | 2011-03-02 | 花王株式会社 | Containerized green tea beverage |
| JP2007022935A (en) * | 2005-07-13 | 2007-02-01 | Kao Corp | Method for producing non-polymer catechin composition |
| JP4751113B2 (en) * | 2005-07-13 | 2011-08-17 | 花王株式会社 | Method for producing non-polymer catechins composition |
| EP1810575A1 (en) | 2006-01-23 | 2007-07-25 | Ito En, Ltd. | Beverage |
| US7666452B2 (en) | 2006-01-25 | 2010-02-23 | Ito En, Ltd. | Beverage comprising cathechins and caffeine |
| CN101019586B (en) * | 2006-02-14 | 2012-09-05 | 株式会社伊藤园 | Beverage |
| JP2007282569A (en) * | 2006-04-17 | 2007-11-01 | Kao Corp | Method for producing refined green tea extract |
| JP4569965B2 (en) * | 2006-04-17 | 2010-10-27 | 花王株式会社 | Method for producing purified green tea extract |
| WO2007122818A1 (en) * | 2006-04-17 | 2007-11-01 | Kao Corporation | Process for producing purified green tea extract |
| WO2007122817A1 (en) * | 2006-04-17 | 2007-11-01 | Kao Corporation | Process for producing purified green tea extract |
| JP2008212024A (en) * | 2007-03-01 | 2008-09-18 | Riverson:Kk | Tea reduced in caffeine content, and method for producing the same |
| JP2008280282A (en) * | 2007-05-10 | 2008-11-20 | Ogawa & Co Ltd | Purification method of polyphenol-containing composition, and polyphenol-containing composition purified by the same |
| JP2011004766A (en) * | 2010-10-08 | 2011-01-13 | Kao Corp | Method for producing decaffeinated raw coffee bean extract |
| JP2013539788A (en) * | 2010-10-13 | 2013-10-28 | クラフト・フーヅ・グローバル・ブランヅ リミテッド ライアビリティ カンパニー | Coffee extract as a material for food, pharmaceuticals, cosmetics, dietary supplements, and biopharmaceuticals |
| JP2014124141A (en) * | 2012-12-26 | 2014-07-07 | Asahi Soft Drinks Co Ltd | Tea beverage and method for increasing the deliciousness of tea beverage |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4181863B2 (en) | 2008-11-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4225814B2 (en) | Caffeine-containing catechin composition decaffeination method | |
| EP2382876B1 (en) | Method of purifying a solid concentrate of a tea extract. | |
| JP4181863B2 (en) | Caffeine-containing catechin composition decaffeination method | |
| JPH06142405A (en) | Method for removing caffeine in aqueous solution containing caffeine | |
| JP6656159B2 (en) | Caffeine removal method and system | |
| US7666452B2 (en) | Beverage comprising cathechins and caffeine | |
| WO2006013871A1 (en) | Process for producing nonpolymeric catechin containing tea extract | |
| JP3662561B2 (en) | Purification method of catechin preparation | |
| EP2517565B1 (en) | Instant black tea | |
| JP4280232B2 (en) | Method for producing purified green tea extract | |
| JP2006008580A (en) | Production method of non-polymer catechins composition | |
| JP2006067828A (en) | Beverage | |
| JP2006174801A (en) | Refined product of green tea extract, and high concentration catechin-containing packaged beverage mixed with the same | |
| JP4381254B2 (en) | Method for producing catechin-containing composition | |
| JP4102746B2 (en) | Method for producing green tea extract | |
| JP2004159597A (en) | Method for producing tea-based composition | |
| JP2006271401A (en) | Method for producing beverage | |
| JP4181848B2 (en) | Purification method of catechin preparation | |
| JP5393770B2 (en) | Powdered tea | |
| JP5307649B2 (en) | Method for producing purified tea extract | |
| JP7425592B2 (en) | Powdered green tea extract composition | |
| JP2006206482A (en) | Method for producing non-polymeric catechin composition | |
| JP2005082533A (en) | Blood peroxide lipid concentration-lowering agent | |
| JP2009274969A (en) | Serum triglyceride concentration-reducing agent | |
| JP2008308460A (en) | Method for purifying low gallate body of non-polymeric catechins |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20040510 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20071023 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20071219 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20080826 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20080901 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110905 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120905 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130905 Year of fee payment: 5 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |