JPH04342590A - Purification of ellagic acid - Google Patents
Purification of ellagic acidInfo
- Publication number
- JPH04342590A JPH04342590A JP14405891A JP14405891A JPH04342590A JP H04342590 A JPH04342590 A JP H04342590A JP 14405891 A JP14405891 A JP 14405891A JP 14405891 A JP14405891 A JP 14405891A JP H04342590 A JPH04342590 A JP H04342590A
- Authority
- JP
- Japan
- Prior art keywords
- ellagic acid
- acid
- alcohol
- water
- ellagic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 229920002079 Ellagic acid Polymers 0.000 title claims abstract description 47
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 title claims abstract description 47
- 235000004132 ellagic acid Nutrition 0.000 title claims abstract description 47
- 229960002852 ellagic acid Drugs 0.000 title claims abstract description 47
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000000746 purification Methods 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 15
- 239000000126 substance Substances 0.000 abstract description 4
- 238000001914 filtration Methods 0.000 abstract description 3
- 239000000401 methanolic extract Substances 0.000 abstract description 3
- 240000007049 Juglans regia Species 0.000 abstract description 2
- 235000009496 Juglans regia Nutrition 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 235000020234 walnut Nutrition 0.000 abstract description 2
- 238000013329 compounding Methods 0.000 abstract 1
- 238000000151 deposition Methods 0.000 abstract 1
- 230000007886 mutagenicity Effects 0.000 abstract 1
- 231100000299 mutagenicity Toxicity 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000843 powder Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 229920001864 tannin Polymers 0.000 description 3
- 239000001648 tannin Substances 0.000 description 3
- 235000018553 tannin Nutrition 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JMGCAHRKIVCLFW-UHFFFAOYSA-N 1-O-Galloylcastalagin Natural products Oc1cc(cc(O)c1O)C(=O)OC2C3OC(=O)c4c2c(O)c(O)c(O)c4c5c(O)c(O)c(O)c6c5C(=O)OC3C7OC(=O)c8cc(O)c(O)c(O)c8c9c(O)c(O)c(O)cc9C(=O)OCC7OC(=O)c%10cc(O)c(O)c(O)c6%10 JMGCAHRKIVCLFW-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001968 ellagitannin Polymers 0.000 description 1
- JMGCAHRKIVCLFW-CNWXVVPTSA-N ellagitannin Chemical compound OC1=C(O)C(O)=CC(C(=O)O[C@H]2C3=C4C(=O)O[C@@H]2[C@@H]2[C@@H]5OC(=O)C6=CC(O)=C(O)C(O)=C6C6=C(O)C(O)=C(O)C=C6C(=O)OC[C@H]5OC(=O)C5=CC(O)=C(O)C(O)=C5C=5C(O)=C(O)C(O)=C(C=5C(=O)O2)C4=C(O)C(O)=C3O)=C1 JMGCAHRKIVCLFW-CNWXVVPTSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、エラグ酸の高純度精製
法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for purifying ellagic acid to high purity.
【０００２】0002
【従来の技術】下記の構造式（１）で占めされるエラグ
酸（Ｅｌｌａｇｉｃ ａｃｉｄ）は、[Prior Art] Ellagic acid represented by the following structural formula (1) is:
【化１】
血液凝固作用、抗変異原性、抗酸化作用等の種々な生理
活性をもつことが知られている天然ポリフェノール性物
質の一種であり、植物体中に遊離の状態で、あるいは多
くの場合、エラジタンニンとして糖と結合した状態で存
在している。エラグ酸の製造方法については、例えばク
ルミ樹皮のメタノール抽出物を酸で加水分解する方法〔
ジャード・エル（Ｊｕｒｄ Ｌ．），ジャーナル・オブ
・アメリカン・ケミカル・ソサイアティ（Ｊ． Ａｍ．
Ｃｈｅｍ． Ｓｏｃ．）、第７８巻、第３４４５頁（
１９５６年）〕，ユーカリ材のパルプ浸漬液から単離す
る方法〔特開昭５１−６３９２１号公報〕，没食子酸ま
たはそのエステルの酸化重合によって製造する方法〔マ
イヤー・ダブリュー（Ｍａｙｅｒ Ｗ．）等、リービッ
ヒス・アンナーレン・ケミーエ（ＬｉｅｂｉｇｓＡｎｎ
． Ｃｈｅｍ．）、第９２９頁（１９８４年）、ハスウ
ェイ・ディー・イー（Ｈａｔｈｗａｙ Ｄ． Ｅ．）、
バイオケミカル・ジャーナル（Ｂｉｏｃｈｅｍ． Ｊ．
）、第６７巻、第４４５頁（１９５７年）、カメル・エ
ル・ワイ（Ｋａｍｅｌ Ｍ． Ｙ．）等、フィトケミス
トリー（Ｐｈｙｔｏｃｈｅｍｉｓｔｏ−ｒｙ）、第１６
巻、第５２１頁（１９７７年）〕、タンニンの分解によ
って製造する方法〔特開平１−７５０９９号公報〕等が
知られている。そして、これらの方法において使用され
ているエラグ酸の精製法は、有機溶剤による抽出、アル
カリまたは有機アミンによる溶解、酸沈殿、カラムクロ
マト、ピリジンからの結晶化等、公知の方法である。[Chemical 1] It is a type of natural polyphenolic substance that is known to have various physiological activities such as blood coagulation, antimutagenicity, and antioxidant effects, and is present in free or large amounts in plants. In this case, it exists in a state bound to sugar as ellagitannin. Regarding the production method of ellagic acid, for example, a method of hydrolyzing methanol extract of walnut bark with acid [
Jurd L., Journal of the American Chemical Society (J. Am.
Chem. Soc. ), Volume 78, Page 3445 (
1956)], a method for isolating eucalyptus wood from a pulp soaking solution [JP-A-51-63921], a method for producing by oxidative polymerization of gallic acid or its ester [Mayer W. et al. LiebigsAnn
．． Chem. ), p. 929 (1984), Hathway D.E.
Biochemical Journal (Biochem. J.
), Vol. 67, p. 445 (1957), Kamel M. Y. et al., Phytochemistry, No. 16
Vol., p. 521 (1977)], a method for producing by decomposition of tannins [JP-A-1-75099], and the like. The purification methods for ellagic acid used in these methods are known methods such as extraction with an organic solvent, dissolution with an alkali or organic amine, acid precipitation, column chromatography, and crystallization from pyridine.
【０００３】0003
【発明が解決しようとする課題】しかしながら、エラグ
酸は酸化によって分解しやすく、また分解生成物はエラ
グ酸と挙動が類似しているため、上記精製法により不純
物を含まず、着色の少ない高純度エラグ酸を得るのは極
めて困難であった。[Problems to be Solved by the Invention] However, since ellagic acid is easily decomposed by oxidation, and the decomposition products behave similarly to ellagic acid, the above purification method has been used to produce high-purity products that do not contain impurities and have little coloring. It was extremely difficult to obtain ellagic acid.
【０００４】0004
【課題を解決するための手段】そこで本発明者等は、上
記課題を解決すべく種々検討した結果、アルコ−ルに、
水を添加しエラグ酸を析出させたのち、エラグ酸を採取
すれば、所期の目的を達成できることを知り本発明を完
成させた。すなわち、本発明は、アルコ−ルに、エラグ
酸を溶解させたものに、水を添加しエラグ酸を析出させ
たのち、エラグ酸を採取することを特徴とするエラグ酸
の精製法である。[Means for Solving the Problems] Therefore, the inventors of the present invention have conducted various studies to solve the above problems, and as a result, the present inventors have found that alcohol
The present invention was completed after learning that the desired purpose could be achieved by adding water to precipitate ellagic acid and then collecting the ellagic acid. That is, the present invention is a method for purifying ellagic acid, which is characterized in that ellagic acid is dissolved in alcohol, water is added to precipitate ellagic acid, and then ellagic acid is collected.
【０００５】以下、本発明について詳述する。先ず、ア
ルコ−ルとしては、例えば、メタノール、エタノール等
が挙げられ、そのうちメタノールは、好適なものという
ことができ、更にアルコ−ルに炭酸ガスを溶解させたも
のは、特に好ましい。上記アルコ−ルに、エラグ酸を例
えば、室温で撹拌しつつ溶解させたものに、水を徐々に
撹拌しつつ添加し、エラグ酸を析出させる。なお、配合
比は、重量比において、エラグ酸１に対し、アルコール
は、最大配合比が約１，２００程度であり、また、水は
、最小配合比が約３８０程度である。そして、このよう
に析出させたエラグ酸を例えば、通常の濾過、遠心分離
等の手段により採取し、エラグ酸を得る。The present invention will be explained in detail below. First, examples of the alcohol include methanol, ethanol, etc. Among them, methanol is preferred, and alcohol in which carbon dioxide gas is dissolved is particularly preferred. For example, ellagic acid is dissolved in the above alcohol at room temperature with stirring, and water is gradually added with stirring to precipitate ellagic acid. In terms of weight ratio, alcohol has a maximum blending ratio of about 1,200 to 1 of ellagic acid, and water has a minimum blending ratio of about 380. Then, the ellagic acid precipitated in this way is collected, for example, by ordinary means such as filtration or centrifugation to obtain ellagic acid.
【０００６】[0006]
【発明の効果】上述した如く、本発明によれば、極めて
高純度のエラグ酸を容易に得ることができるので、極め
て有意義な発明である。[Effects of the Invention] As described above, according to the present invention, ellagic acid of extremely high purity can be easily obtained, so it is an extremely significant invention.
【０００７】[0007]
【実施例】以下に、本発明を実施例を挙げてさらに詳細
に説明する。
実施例
ペルー産タラパウダー（タラの木の果筴の乾燥粉末）の
メタノール抽出物（タラタンニンを約７０％含有する粉
末）を水に溶解し、タンニン濃度１０．９％（Ｗ／Ｖ）
の水溶液を調製した。不溶物を濾別したのち、４０％（
Ｗ／Ｖ）カセイソーダ水溶液でｐＨ８．０に調整した。
この液１，０００ｍｌを５，０００ｍｌ容ヒダ付三角フ
ラスコに入れ、重炭酸ナトリウム粉末６３ｇを添加し、
温度２５℃で２４時間、ロータリーシェーカー（２００
ｒ．ｐ．ｍ）上で振盪した。反応終了後のエラグ酸濃度
は５７．１ｍｇ／ｍｌであった。この反応液２００ｍｌ
（エラグ酸量１１．４ｇ）を吸引濾過してエラグ酸の沈
殿物を集め、０．２５Ｍ重炭酸ナトリウム液６００ｍｌ
で洗浄した。この洗浄ケーキを２，３００ｍｌのイオン
交換水に懸濁したのち、撹拌下で５Ｎカセイソーダ液を
滴下し、エラグ酸を溶解させた。溶液のｐＨは１２．８
であった。不溶物をセライト（ハイフロスーパーセル）
を濾過助剤として濾別し、清澄なエラグ酸の溶液を得た
。このアルカリ溶液に撹拌下で５Ｎ塩酸を添加し、ｐＨ
を１０に調整した。約１時間ゆるやかに撹拌を続けたの
ち、吸引濾過してエラグ酸の凝集沈殿物を集め、０．２
５Ｍ重炭酸ナトリウム液４００ｍｌで洗浄した。洗浄ケ
ーキを再び１，２００ｍｌのイオン交換水に懸濁したの
ち、５Ｎカセイソーダ液を滴下し、エラグ酸を溶解させ
た。溶液のｐＨは１２．８であった。この溶液に３１％
過酸化水素水を０．５％（Ｖ／Ｖ）となる如く添加し、
温度２５℃でゆるやかに攪拌しつゝ、２時間脱色したの
ち、５Ｎ塩酸を加えてｐＨ１０に調整し、そのまゝ１時
間攪拌を続けた。生成したエラグ酸塩の凝集沈殿物を吸
引濾過して集め、０．２５Ｍ重炭酸ナトリウム液２００
ｍｌで洗浄した。この洗浄ケーキを２００ｍｌの０．１
Ｎ塩酸に懸濁したのち、５Ｎ塩酸を加えてｐＨ２に調整
した。
温度２５℃で１時間緩やかに攪拌したのち、遊離型のエ
ラグ酸の沈殿物を吸引濾過して集め、イオン交換水で充
分に洗浄した。この洗浄ケーキを真空乾燥したのち、乳
鉢で粉砕し、微黄白色の生成粉末８．１ｇ（Ｌ＝８３．
６８、ａ＝−０．３７、ｂ＝１１．９３）を得た。なお
、上記Ｌ、ａ、ｂ値は、色差計〔日本電色（株）製、Ｚ
−１００１ＤＰ〕を用いて色調を測定したものである。
反応液からのエラグ酸の回収率は７１％、精製標品の高
速液体クロマトグラフィー（以下ＨＰＬＣと略称する。
）分析における純度は９９．５％であった。
なお、エラグ酸の定量分析は、ＴＳＫゲルＯＤＳ １２
０Ａ カラム（２５ｃｍ、東洋曹達工業社製）を用い、
２５５ｎｍで検出するＨＰＬＣ法によった。溶離液には
Ｍ／３０燐酸緩衝液（ｐＨ７．０）とメタノールの混合
液（７：３）を用いた。このようにして精製したエラグ
酸１ｇを、炭酸ガスを溶解したメタノールに溶解した。
緩やかに攪拌しながらレジン水９００ｍｌを徐々に添加
しエラグ酸を析出させた。更に氷冷して完全にエラグ酸
析出させたのち直径７．５ｃｍの濾紙２枚で濾過しエラ
グ酸を採取して、真空乾燥した。このようにして得られ
たエラグ酸は極微黄白色（Ｌ＝９５．７２、ａ＝−３．
２８、ｂ＝１４．１６）であり、極めて良好な色調であ
った。[Examples] The present invention will be explained in more detail below with reference to Examples. Example A methanol extract (powder containing about 70% cod tannin) of Peruvian cod powder (dried powder of cod cod) was dissolved in water, and the tannin concentration was 10.9% (W/V).
An aqueous solution was prepared. After filtering out insoluble matter, 40% (
W/V) The pH was adjusted to 8.0 with a caustic soda aqueous solution. Pour 1,000 ml of this liquid into a 5,000 ml pleated Erlenmeyer flask, add 63 g of sodium bicarbonate powder,
In a rotary shaker (200°C) for 24 hours at a temperature of 25℃.
r. p. m) shaken on top. The ellagic acid concentration after the completion of the reaction was 57.1 mg/ml. 200ml of this reaction solution
(Amount of ellagic acid: 11.4 g) was suction filtered to collect the precipitate of ellagic acid, and 600 ml of 0.25M sodium bicarbonate solution was added.
Washed with. After suspending this washed cake in 2,300 ml of ion exchange water, 5N caustic soda solution was added dropwise under stirring to dissolve ellagic acid. The pH of the solution is 12.8
Met. Celite the insoluble matter (Hyflo Super Cell)
was filtered as a filter aid to obtain a clear solution of ellagic acid. 5N hydrochloric acid was added to this alkaline solution under stirring to adjust the pH.
was adjusted to 10. After continuing to stir gently for about 1 hour, the agglomerated precipitate of ellagic acid was collected by suction filtration, and 0.2
Washed with 400 ml of 5M sodium bicarbonate solution. After suspending the washed cake in 1,200 ml of ion-exchanged water again, 5N caustic soda solution was added dropwise to dissolve ellagic acid. The pH of the solution was 12.8. This solution contains 31%
Add hydrogen peroxide solution to 0.5% (V/V),
After decolorizing for 2 hours while stirring gently at a temperature of 25° C., 5N hydrochloric acid was added to adjust the pH to 10, and stirring was continued for 1 hour. The resulting coagulated precipitate of ellagate was collected by suction filtration and diluted with 0.25 M sodium bicarbonate solution at 200 ml.
Washed with ml. 200ml of this washed cake is 0.1
After suspending in N hydrochloric acid, the pH was adjusted to 2 by adding 5N hydrochloric acid. After gently stirring at a temperature of 25° C. for 1 hour, the precipitate of free ellagic acid was collected by suction filtration and thoroughly washed with ion-exchanged water. After drying this washed cake in vacuum, it was crushed in a mortar and 8.1 g of slightly yellowish white powder was produced (L=83.
68, a=-0.37, b=11.93). The above L, a, and b values were measured using a color difference meter [manufactured by Nippon Denshoku Co., Ltd., Z
-1001DP]. The recovery rate of ellagic acid from the reaction solution was 71%, and the purity in high performance liquid chromatography (hereinafter abbreviated as HPLC) analysis of the purified sample was 99.5%. For quantitative analysis of ellagic acid, TSK gel ODS 12
Using a 0A column (25cm, manufactured by Toyo Soda Kogyo Co., Ltd.),
HPLC method with detection at 255 nm was used. A mixture of M/30 phosphate buffer (pH 7.0) and methanol (7:3) was used as the eluent. 1 g of ellagic acid purified in this way was dissolved in methanol in which carbon dioxide gas had been dissolved. While stirring gently, 900 ml of resin water was gradually added to precipitate ellagic acid. After further cooling on ice to completely precipitate ellagic acid, the mixture was filtered through two pieces of filter paper with a diameter of 7.5 cm to collect ellagic acid, which was vacuum dried. The ellagic acid thus obtained was extremely pale yellowish white (L=95.72, a=-3.
28, b=14.16), and the color tone was extremely good.
Claims (1)
ものに、水を添加しエラグ酸を析出させたのち、エラグ
酸を採取することを特徴とするエラグ酸の精製法。1. A method for purifying ellagic acid, which comprises adding water to a solution of ellagic acid in alcohol to precipitate ellagic acid, and then collecting the ellagic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14405891A JPH04342590A (en) | 1991-05-21 | 1991-05-21 | Purification of ellagic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14405891A JPH04342590A (en) | 1991-05-21 | 1991-05-21 | Purification of ellagic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04342590A true JPH04342590A (en) | 1992-11-30 |
Family
ID=15353336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14405891A Pending JPH04342590A (en) | 1991-05-21 | 1991-05-21 | Purification of ellagic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04342590A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632380A (en) * | 2016-11-21 | 2017-05-10 | 东北林业大学 | Process for producing high-purity ellagic acid by desolvation crystallization method |
| CN110357900A (en) * | 2019-08-02 | 2019-10-22 | 中国科学院新疆理化技术研究所 | A kind of intermediate processing obtaining ellagic acid from pomegranate rind extract |
-
1991
- 1991-05-21 JP JP14405891A patent/JPH04342590A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632380A (en) * | 2016-11-21 | 2017-05-10 | 东北林业大学 | Process for producing high-purity ellagic acid by desolvation crystallization method |
| CN110357900A (en) * | 2019-08-02 | 2019-10-22 | 中国科学院新疆理化技术研究所 | A kind of intermediate processing obtaining ellagic acid from pomegranate rind extract |
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