JP4181848B2 - Purification method of catechin preparation - Google Patents
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Description
【０００１】
【発明の属する技術分野】
本発明は飲料用のカテキン製剤の精製方法に関する。
【０００２】
【従来の技術】
カテキン類の効果として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ためには、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とからより簡便に大量のカテキン類を摂取するために、飲料にカテキン類を高濃度配合する技術が望まれていた。この方法の一つとして、カテキン製剤（例えば、特許文献３〜５参照）などを利用して、飲料にカテキン類を配合する方法がある。
【０００３】
しかしながら、このままのカテキン製剤では、溶解したカテキン類が苦味、渋味を呈するとともに、カテキン製剤に含まれるその他の成分によって、苦味、渋味、エグ味、雑味が強すぎ、飲用に適さない。これを緩和すべく各種の甘味料などを配合することにより、飲用時の苦味、渋味を緩和する方法はあるが、この方法は甘味によるマスキング法であることから、完全な渋味や苦味の低減には限界があるとともに、エグ味や雑味の問題は解決されていなかった。
【０００４】
一方、高度に精製された緑茶抽出物の精製物を使用した場合、長期保存時の沈殿物の問題は回避できるものの、高濃度の非重合体カテキン類を配合した飲料においては、緑茶抽出物の精製物からくる人工的な刺すような苦味が感じられ飲用には適していなかった。
【０００５】
また茶系抽出液にアルコールを添加してそれにより生じた沈殿を除いた茶系アルコール飲料用濃縮液の製造方法（例えば、特許文献６参照。）や茶類抽出液を陽イオン交換樹脂と接触した後、その処理液にエタノールを添加して沈殿物を生ぜしめ、該沈殿物を濾別除去する茶葉タンニンの製造方法（例えば、特許文献７参照。）が報告されている。しかしながら特許文献６では、本質的に微生物の繁殖を抑制する為に茶系飲料用濃縮液中に１５ｖ／ｖ％〜６０ｖ／ｖ％のエタノールを含有することが必須となっている。また特許文献７では、実質的にカフェインが除去された茶葉タンニン類を製造すべく、陽イオン交換樹脂で処理する工程が必須となっている。しかしながらこの方法では、茶葉タンニン類の他の飲料の旨味として重要な、カフェイン、アミノ酸類、糖類等の茶葉タンニン類以外の成分がすべて除去されてしまい、飲料用としては好ましくないものとなっている。
【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５９−２１９３８４号公報
【特許文献４】
特開平４−２０５８９号公報
【特許文献５】
特開昭６１−１３０２８５号公報
【特許文献６】
特開２００２−２０９５１９号公報
【特許文献７】
特開平１１−２２８５６５号公報
【０００７】
【発明が解決しようとする課題】
本発明の目的は、風味が改善された高濃度に非重合体カテキン類を含有する飲料の製造に有用なカテキン製剤の精製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、緑茶葉由来のカテキン製剤の精製において、水又は水と有機溶媒の混合物に溶解させたカテキン製剤溶液に有機溶媒を加えていく比率を調節することによってカテキン製剤溶液から生成する沈殿物の量が調節でき、風味に優れたカテキン製剤が得られることを見出した。
【０００９】
本発明は、緑茶葉から得られた非重合体カテキン類を２５〜４０重量％含有するカテキン製剤を、水と有機溶媒の混合溶媒に溶解させ、これに有機溶媒を加えることにより有機溶媒と水の重量比率を９／１〜５／５の範囲に調整して、沈殿物を生じせしめ、懸濁液中の固形分を分離し、残った液相から溶媒を留去することを特徴とするカテキン製剤の精製方法を提供するものである。
【００１０】
【発明の実施の形態】
本発明で非重合体カテキン類とは、カテキン、ガロカテキン、カテキンガレート及びガロカテキンガレートなど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及びエピガロカテキンガレートなどのエピ体カテキン類をあわせての総称である。
【００１１】
本発明に使用するカテキン製剤は、非重合カテキン類を２５〜４０重量％含有するカテキン製剤であり、緑茶葉から水又は有機溶媒と水の混合物で抽出されたものである。カテキン製剤には、カテキン類の他に、カフェイン、アミノ酸、有機酸などが含まれている。カテキン製剤の呈味において、アミノ酸、シュウ酸をはじめとする有機酸などの水溶性成分が重要な因子となる。より具体的には、Camellia属、例えばC. sinensis、C. assamica及びやぶきた種、又はそれらの雑種から得られる茶葉から製茶された茶葉から水又は水と有機溶媒の混合物によって抽出、濃縮したものが挙げられる。当該製茶された茶葉には、煎茶、番茶、玉露、てん茶、釜炒り茶などの緑茶類がある。
また市販の三井農林（株）「ポリフェノン」、伊藤園（株）「テアフラン」、太陽化学（株）「サンフェノン」などのカテキン製剤を固体のカテキン製剤として用いることもできる。
ここでいう茶抽出物の濃縮物の形態としては、固体、水溶液、スラリー状など種々のものが挙げられる。
【００１２】
本発明のカテキン製剤の精製方法においては、まずカテキン製剤を水又は水と有機溶媒との混合物に溶解させる。このとき使用でき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。好ましくはエタノール、メタノール、アセトンの親水性有機溶媒、特に飲料へ使用をすることから有機溶剤の残留を考慮しエタノールが好ましい。
【００１３】
カテキン製剤の溶解に用いる溶媒は、水と有機溶媒との混合物であるが水／有機溶媒の重量比率は９／１〜５／５の間に調整を行う。この比率が５／５未満の場合、カテキン製剤の溶解性が悪くなり、液液抽出の抽出効率が低下する。
【００１４】
次いで、カテキン製剤の溶液に有機溶媒を徐々に添加していくことにより、カテキン製剤溶液中に不溶成分の沈殿物を生じせしめる。ここ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、酢酸エチルがある。好ましくはエタノール、メタノール、アセトンの親水性有機溶媒、特に好ましくは飲料への使用することから、有機溶剤の残留を考慮しエタノールが良い。
【００１５】
カテキン製剤溶液へ添加する有機溶媒の量は、不溶成分の沈殿物生成の点から、有機溶媒と水の重量比率を９／１〜５／５の範囲に調整することが必要であり、好ましくは８／２〜６／４が良い。有機溶媒／水比が９／１を超えると使用する有機溶媒量が過大になり、経済的に好ましくない。また有機溶媒／水比が５／５未満の場合、沈殿物の濾過分離性が悪くなり好ましくない。
【００１６】
また有機溶媒の添加方法は、必要量を１０〜３０分程度の時間でゆっくり滴下するのが好ましく、また不溶成分の生成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分から４０分程度の熟成時間を設けると更に好ましい。
カテキン製剤溶液への有機溶媒の添加による不溶成分の沈殿物生成の温度は特に限定されないが有機溶媒を使用する為に０〜６０℃が良く、好ましくは１０〜６０℃、更に好ましくは１０〜４０℃が精製工程の管理上簡便であり好ましい。
【００１７】
懸濁液中の固形分を分離し、残った液相から有機溶媒を留去すれば、目的とするカテキン製剤が得られる。固液分離方法は通常の方法、例えば遠心分離や濾過などを使用することができる。また分離して得られた液相からの有機溶媒の留去方法は通常の方法が使用できるが、カテキン製剤の精製物への熱負荷を極力避けるために減圧蒸留が好ましい。
【００１８】
本発明のカテキン製剤の精製物中の非重合体カテキン類の濃度は、２６〜５０重量％、更に３０〜４５重量％、特に３０〜４０重量％、殊更３５〜４０重量％が好ましい。
カテキン製剤の精製物中の非重合体カテキン類の濃度が、２６重量％未満の場合、緑茶抽出物の精製物中に含まれる他の呈味成分の影響が出てしまい、これを配合した高濃度の非重合体カテキン類飲料は嫌味のある渋味を感じると共に、清涼感のない飲料になってしまい好ましくない。カテキン製剤の精製物中の非重合体カテキン類の濃度が、５０重量％を超える場合、カテキン製剤の精製物の非重合体カテキン類以外の旨味の成分などをシュウ酸と共に除去し過ぎてしまうことになり、飲料配合用のカテキン製剤の精製物としては好ましくない。
【００１９】
本発明のカテキン製剤の精製後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方が好ましい。したがって上記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。
【００２０】
また、本発明の緑茶抽出物の精製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が４５重量％以上が、非重合体カテキン類の生理効果の有効性上好ましい。
【００２１】
本発明の精製方法によって得られるカテキン製剤は、非重合体カテキン類（Ａ）とシュウ酸（Ｂ）の含有重量比[（Ｂ）／（Ａ）]が０．００１〜０．０３５、さらに０．００１〜０．０３、特に０．００１５〜０．０３、殊更０．０１５〜０．０１が好ましい。
カテキン製剤の精製物中のシュウ酸比率が低すぎると、旨味の成分などをシュウ酸と共に除去し過ぎてしまうことになり、飲料配合用のカテキン製剤の精製物としては好ましくない。またカテキン製剤の精製物中のシュウ酸比率が高すぎると、カテキン製剤の濃縮物で感じられたような、嫌味のある渋味を感じると共に、清涼感のない飲料になってしまい好ましくない。
【００２２】
本発明のカテキン製剤の精製後のシュウ酸濃度は、０．０５〜１．５重量％、更に０．０５〜１．０重量％、特に０．０５〜０．５重量％、殊更０．０８〜０．３重量％が好ましい。
カテキン製剤の精製後のシュウ酸濃度が、１．５重量％を超える場合、カテキン製剤の精製物中に含まれる他の呈味成分の影響により、配合した高濃度の非重合体カテキン類飲料は嫌味のある渋味を感じると共に、清涼感のない飲料になってしまい好ましくない。カテキン製剤の精製後の非重合体カテキン類の濃度が、０．０５重量％未満の場合、カテキン製剤の精製物の非重合カテキン類以外の旨味の成分などをシュウ酸と共に除去し過ぎてしまうことになり、飲料配合用のカテキン製剤の精製物としては好ましくない。
【００２３】
【実施例】
カテキン類の測定
カテキン製剤の精製物を蒸留水で希釈、フィルター（０．８μｍ）でろ過し、島津製作所製、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。
【００２４】
シュウ酸の測定
日本ダイオネックス社製（形式ＤＸＡＱ１１１０）にカラム：ＩｏｎＰａｃＡＳ４Ａ−ＳＣ、４×２５０mmを装着し、サプレッサーＡＳＲＳ−ＵＬＴＲＡ（ダイオネックス社製）に接続し、リサイクルモードで行った。移動相は１．８mmol／ＬＮａ2ＣＯ3水溶液、１．７mmol／ＬＮａＨＣＯ3水溶液を、１．０mL／minで流し、試料注入量は２５μＬとした。検出器は電気伝導度計を使用した。
【００２５】
実施例１〜４、比較例１
表１に示すように液液抽出時の有機溶媒／水比を変化させることによって、生成される不溶成分量を調整することによりカテキン製剤の精製を行った。すなわち、カテキン製剤を水とエタノールの混合溶媒に溶解した後、エタノールを添加してエタノールと水の比を表１記載の比に調整して沈澱物を生じさせ、固形物を濾過して除去し、次いでエタノールを減圧留去した。
【００２６】
【表１】
１）精製後のカテキン製剤をイオン交換水に非重合体カテキン類濃度で０．１重量％になるように添加し、３人の味覚パネラーによって評価を実施。
２）緑茶抽出物の濃縮物
ポリフェノンＨＧ（東京フードテクノ製）
非重合体カテキン類含有量３３．７０重量％、シュウ酸含有量２．０３重量％
シュウ酸／非重合体カテキン類＝０．０６０
【００２８】
液液抽出時のエタノール／水比を７０／３０とすることによって、精製後のシュウ酸／非重合体カテキン比は極めて低くなり、従来のカテキン類にあったエグ味が感じられなくなることがわかった。またカテキン製剤の溶解時に水１００％に溶解するよりもエタノール水溶液への溶解によって、精製効率が高くなることが判明した。
【００２９】
【発明の効果】
風味が良好なカテキン高濃度含有飲料の製造に有用なカテキン製剤が得られる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for purifying a catechin preparation for beverages.
[0002]
[Prior art]
Known effects of catechins include cholesterol elevation inhibitory action and α-amylase activity inhibitory action (see, for example, Patent Document 1 and Patent Document 2). In order to express such physiological effects of catechins, it is necessary to drink 4 to 5 cups of tea per day for adults. Therefore, in order to easily ingest a large amount of catechins, A technique for blending a high concentration of sucrose has been desired. As one of the methods, there is a method of blending catechins into a beverage using a catechin preparation (see, for example, Patent Documents 3 to 5).
[0003]
However, in the catechin preparation as it is, the dissolved catechins have a bitter taste and astringency, and the other ingredients contained in the catechin preparation are too bitter, astringent, abundant and miscellaneous, and are not suitable for drinking. There is a method to alleviate the bitterness and astringency when drinking by blending various sweeteners to alleviate this, but this method is a masking method by sweetness, so it can be completely astringent and bitter The reduction has a limit, and the problem of taste and miscibility has not been solved.
[0004]
On the other hand, when a highly purified green tea extract is used, the problem of sediment during long-term storage can be avoided, but in beverages containing high concentrations of non-polymer catechins, Artificial biting bitterness from the purified product was felt and was not suitable for drinking.
[0005]
In addition, a method for producing a concentrated concentrate for tea-based alcoholic beverages by adding alcohol to a tea-based extract and removing precipitates produced thereby (see, for example, Patent Document 6) or contacting a tea extract with a cation exchange resin After that, a method for producing tea leaf tannin has been reported in which ethanol is added to the treatment solution to form a precipitate, and the precipitate is removed by filtration (see, for example, Patent Document 7). However, in Patent Document 6, it is essential to contain 15 v / v% to 60 v / v% ethanol in the concentrated concentrate for tea-based beverages in order to essentially suppress the growth of microorganisms. Moreover, in patent document 7, in order to manufacture the tea leaf tannin from which caffeine was substantially removed, the process processed with a cation exchange resin is essential. However, this method removes all components other than tea leaf tannins, such as caffeine, amino acids, and sugars, which are important as the umami of other beverages of tea leaf tannins, and is not preferable for beverages. Yes.
[0006]
[Patent Document 1]
JP-A-60-156614 [Patent Document 2]
Japanese Patent Laid-Open No. 3-133828 [Patent Document 3]
JP 59-219384 A [Patent Document 4]
JP-A-4-20589 [Patent Document 5]
Japanese Patent Laid-Open No. 61-130285 [Patent Document 6]
JP 2002-209519 A [Patent Document 7]
Japanese Patent Laid-Open No. 11-228565
[Problems to be solved by the invention]
An object of the present invention is to provide a method for purifying a catechin preparation useful for producing a beverage containing non-polymer catechins at a high concentration with improved flavor.
[0008]
[Means for Solving the Problems]
In the purification of catechin preparations derived from green tea leaves, the present inventor determined a precipitate formed from a catechin preparation solution by adjusting the ratio of adding the organic solvent to the catechin preparation solution dissolved in water or a mixture of water and an organic solvent. It was found that a catechin preparation having an excellent flavor can be obtained by adjusting the amount of the product.
[0009]
In the present invention, a catechin preparation containing 25 to 40% by weight of non-polymer catechins obtained from green tea leaves is dissolved in a mixed solvent of water and an organic solvent, and the organic solvent and water are added to the catechin preparation. The weight ratio is adjusted to a range of 9/1 to 5/5 to form a precipitate, the solid content in the suspension is separated, and the solvent is distilled off from the remaining liquid phase. A method for purifying a catechin preparation is provided.
[0010]
DETAILED DESCRIPTION OF THE INVENTION
Non-polymer catechins in the present invention are non-epimeric catechins such as catechin, gallocatechin, catechin gallate and gallocatechin gallate and epi-catechins such as epicatechin, epigallocatechin, epicatechin gallate and epigallocatechin gallate Is a collective term.
[0011]
The catechin preparation used in the present invention is a catechin preparation containing 25 to 40% by weight of non-polymerized catechins and extracted from green tea leaves with water or a mixture of an organic solvent and water. In addition to catechins, catechin preparations include caffeine, amino acids, organic acids and the like. In taste of catechin preparations, water-soluble components such as amino acids and organic acids such as oxalic acid are important factors. More specifically, extracted from tea leaves made from tea leaves made from the genus Camellia, such as C. sinensis, C. assamica, and hybrids, or mixed with water or a mixture of water and an organic solvent. Is mentioned. The tea leaves produced include green teas such as sencha, bancha, gyokuro, tencha, and kettle roasted tea.
Commercially available catechin preparations such as Mitsui Norin Co., Ltd. “Polyphenone”, ITO EN Co., Ltd. “Theafuran”, Taiyo Kagaku Co., Ltd. “Sunphenon” can also be used as solid catechin preparations.
The form of the concentrate of the tea extract here includes various forms such as a solid, an aqueous solution, and a slurry.
[0012]
In the purification method of a catechin preparation of the present invention, first, the catechin preparation is dissolved in water or a mixture of water and an organic solvent. Examples of the organic solvent that can be used at this time include ethanol, methanol, acetone, and ethyl acetate. Preferably, ethanol, methanol, and acetone are used as hydrophilic organic solvents, and ethanol is preferable in consideration of the residual organic solvent because it is used for beverages.
[0013]
The solvent used for dissolving the catechin preparation is a mixture of water and an organic solvent, but the weight ratio of water / organic solvent is adjusted between 9/1 and 5/5. When this ratio is less than 5/5, the solubility of the catechin preparation becomes poor, and the extraction efficiency of liquid-liquid extraction decreases.
[0014]
Next, an organic solvent is gradually added to the solution of the catechin preparation to cause a precipitate of insoluble components in the catechin preparation solution. Examples of the organic solvent used here include ethanol, methanol, acetone, and ethyl acetate. Since it is preferably used for a hydrophilic organic solvent such as ethanol, methanol, and acetone, and particularly preferably used for beverages, ethanol is preferable in consideration of the residual organic solvent.
[0015]
The amount of the organic solvent to be added to the catechin preparation solution needs to adjust the weight ratio of the organic solvent to water in the range of 9/1 to 5/5 from the viewpoint of the formation of a precipitate of insoluble components, preferably 8/2 to 6/4 is preferable. When the organic solvent / water ratio exceeds 9/1, the amount of the organic solvent to be used becomes excessive, which is economically undesirable. Moreover, when the organic solvent / water ratio is less than 5/5, the filtration separation property of the precipitate is deteriorated, which is not preferable.
[0016]
Moreover, as for the addition method of the organic solvent, it is preferable to slowly drop the required amount in a time of about 10 to 30 minutes, and it is preferable to drop it in a stirring state in order to increase the production efficiency of insoluble components. It is more preferable to provide an aging time of about 10 to 40 minutes after the completion of the dropwise addition of water.
The temperature at which the precipitate of the insoluble component is formed by adding an organic solvent to the catechin preparation solution is not particularly limited, but 0-60 ° C is preferable for using the organic solvent, preferably 10-60 ° C, more preferably 10-40. ° C is preferred because it is convenient for the purification process.
[0017]
The target catechin preparation can be obtained by separating the solid content in the suspension and distilling off the organic solvent from the remaining liquid phase. As the solid-liquid separation method, an ordinary method such as centrifugation or filtration can be used. Moreover, although the normal method can be used for the distilling-off method of the organic solvent from the liquid phase obtained by isolate | separating, in order to avoid the heat load to the refined | purified product of a catechin preparation as much as possible, vacuum distillation is preferable.
[0018]
The concentration of the non-polymer catechins in the purified product of the catechin preparation of the present invention is preferably 26 to 50% by weight, more preferably 30 to 45% by weight, particularly 30 to 40% by weight, and particularly preferably 35 to 40% by weight.
When the concentration of the non-polymer catechins in the purified product of the catechin preparation is less than 26% by weight, the influence of other taste components contained in the purified product of the green tea extract comes out. A non-polymer catechin beverage having a concentration is unfavorable because it feels an astringent taste with an unpleasant taste and becomes a beverage without a refreshing feeling. When the concentration of non-polymer catechins in the purified product of the catechin preparation exceeds 50% by weight, umami components other than the non-polymer catechins in the purified product of the catechin preparation may be removed together with oxalic acid. Therefore, it is not preferable as a purified product of a catechin preparation for blending beverages.
[0019]
The non-polymer catechins after purification of the catechin preparation of the present invention are non-gallo consisting of epigallocatechin gallate, gallocatechin gallate, epigallocatechin and gallocatechin, and catechin gallate, catechin gallate, epicatechin and catechin. It is preferable that the body ratio maintains the composition of natural green tea leaves. Therefore, it is preferable that the total amount of the four types of galloforms always exceeds the total amount of the four types of non-galloforms in that the composition of natural green tea leaves is maintained even in the purified product.
[0020]
In the purified product of the green tea extract of the present invention, catechin gallate, epicatechin gallate, gallocatechin gallate and gallate composed of epigallocatechin gallate have a proportion of 45% by weight or more in all non-polymer catechins, It is preferable on the effectiveness of the physiological effect of non-polymer catechins.
[0021]
The catechin preparation obtained by the purification method of the present invention has a weight ratio [(B) / (A)] of non-polymer catechins (A) and oxalic acid (B) of 0.001 to 0.035, and further 0 0.001 to 0.03, particularly 0.0015 to 0.03, and particularly 0.015 to 0.01 are preferred.
If the ratio of oxalic acid in the purified product of the catechin preparation is too low, umami components and the like are removed together with oxalic acid, which is not preferable as a purified product of the catechin preparation for blending beverages. Further, if the ratio of oxalic acid in the purified product of the catechin preparation is too high, it is not preferable because a taste of astringency that is unpleasant as that felt in the concentrate of the catechin preparation is felt and the beverage has no refreshing feeling.
[0022]
The oxalic acid concentration after purification of the catechin preparation of the present invention is 0.05 to 1.5% by weight, more preferably 0.05 to 1.0% by weight, particularly 0.05 to 0.5% by weight, and particularly 0.08. -0.3 wt% is preferred.
When the oxalic acid concentration after purification of the catechin preparation exceeds 1.5% by weight, the blended high concentration non-polymer catechin beverage is due to the influence of other taste components contained in the purified product of the catechin preparation. It is unfavorable because it causes a bitter taste with an unpleasant taste and a refreshing beverage. When the concentration of non-polymer catechins after purification of the catechin preparation is less than 0.05% by weight, umami components other than the non-polymer catechins in the purified catechin preparation may be removed together with oxalic acid. Therefore, it is not preferable as a purified product of a catechin preparation for blending beverages.
[0023]
【Example】
Measurement of catechins The purified product of catechin preparation was diluted with distilled water, filtered with a filter (0.8 μm), and then a liquid introduced with octadecyl group using a high performance liquid chromatograph (model SCL-10AVP) manufactured by Shimadzu Corporation. A chromatographic packed column L-column TM ODS (4.6 mmφ × 250 mm: manufactured by Chemical Substances Research Institute) was attached, and the gradient method was performed at a column temperature of 35 ° C. The mobile phase A solution was a distilled aqueous solution containing 0.1 mol / L of acetic acid, the B solution 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.
[0024]
Measurement of oxalic acid A column: IonPacAS4A-SC, 4 × 250 mm was attached to Nippon Dionex (model DXAQ1110), connected to a suppressor ASRS-ULTRA (Dionex), and performed in a recycling mode. . As the mobile phase, a 1.8 mmol / LNa 2 CO 3 aqueous solution, a 1.7 mmol / L NaHCO 3 aqueous solution was flowed at 1.0 mL / min, and the sample injection amount was 25 μL. An electric conductivity meter was used as a detector.
[0025]
Examples 1-4, Comparative Example 1
As shown in Table 1, the catechin preparation was purified by adjusting the amount of insoluble components produced by changing the organic solvent / water ratio during liquid-liquid extraction. That is, after dissolving the catechin preparation in a mixed solvent of water and ethanol, ethanol is added to adjust the ratio of ethanol to water to the ratio shown in Table 1 to form a precipitate, and the solid matter is removed by filtration. Then, ethanol was distilled off under reduced pressure.
[0026]
[Table 1]
1) The purified catechin preparation was added to ion-exchanged water so that the concentration of non-polymer catechins was 0.1% by weight, and evaluation was performed by three taste panelists.
2) Concentrate of green tea extract Polyphenon HG (manufactured by Tokyo Food Techno)
Non-polymer catechins content 33.70% by weight, oxalic acid content 2.03% by weight
Oxalic acid / non-polymer catechins = 0.060
[0028]
It can be seen that by setting the ethanol / water ratio at the time of liquid-liquid extraction to 70/30, the oxalic acid / non-polymer catechin ratio after purification becomes extremely low, and the taste of conventional catechins cannot be felt. It was. It was also found that the purification efficiency was increased by dissolution in an ethanol aqueous solution rather than dissolution in 100% water when the catechin preparation was dissolved.
[0029]
【The invention's effect】
A catechin preparation useful for producing a beverage containing a high concentration of catechin having a good flavor is obtained.
Claims (2)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002313081A JP4181848B2 (en) | 2002-10-28 | 2002-10-28 | Purification method of catechin preparation |
| AU2003275679A AU2003275679A1 (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 |
| EP11173762.3A EP2382876B1 (en) | 2002-10-28 | 2003-10-27 | Method of purifying a solid concentrate of a tea extract. |
| CN2006101695003A CN1981586B (en) | 2002-10-28 | 2003-10-27 | Method for purifying condensate of tea extraction compound |
| EP11173763.1A EP2382877B8 (en) | 2002-10-28 | 2003-10-27 | Green tea extract |
| US10/532,727 US7883734B2 (en) | 2002-10-28 | 2003-10-27 | Method of removing caffeine from caffeine-containing catechin compound composition |
| EP03758933.0A EP1557097B1 (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 |
| PCT/JP2003/013700 WO2004037022A1 (en) | 2002-10-28 | 2003-10-27 | 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 |
| TW099122034A TW201038206A (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 |
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| JP2002313081A JP4181848B2 (en) | 2002-10-28 | 2002-10-28 | Purification method of catechin preparation |
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| JP4751113B2 (en) * | 2005-07-13 | 2011-08-17 | 花王株式会社 | Method for producing non-polymer catechins composition |
| JP5081028B2 (en) * | 2008-03-24 | 2012-11-21 | 花王株式会社 | Method for producing purified green tea extract containing non-polymer catechins |
| JP6312418B2 (en) * | 2012-12-28 | 2018-04-18 | 花王株式会社 | Production method of tea extract |
| JP7410699B2 (en) | 2018-12-06 | 2024-01-10 | 花王株式会社 | Powdered green tea extract composition |
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