JPH02225491A - Method for extracting glycyrrhizin - Google Patents
Method for extracting glycyrrhizinInfo
- Publication number
- JPH02225491A JPH02225491A JP1046954A JP4695489A JPH02225491A JP H02225491 A JPH02225491 A JP H02225491A JP 1046954 A JP1046954 A JP 1046954A JP 4695489 A JP4695489 A JP 4695489A JP H02225491 A JPH02225491 A JP H02225491A
- Authority
- JP
- Japan
- Prior art keywords
- carbon dioxide
- glycyrrhizin
- licorice
- extraction
- supercritical
- 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
- 239000004378 Glycyrrhizin Substances 0.000 title claims abstract description 15
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 229960004949 glycyrrhizic acid Drugs 0.000 title claims abstract description 15
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 235000019410 glycyrrhizin Nutrition 0.000 title claims abstract description 15
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims description 18
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 21
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 21
- 238000000605 extraction Methods 0.000 claims abstract description 21
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 claims abstract description 12
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 claims abstract description 11
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 claims abstract description 11
- 229940010454 licorice Drugs 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 8
- 240000004670 Glycyrrhiza echinata Species 0.000 claims 1
- 241000202807 Glycyrrhiza Species 0.000 abstract description 10
- 230000000954 anitussive effect Effects 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 229940124584 antitussives Drugs 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract description 2
- 235000005883 Glycyrrhiza glabra var glandulifera Nutrition 0.000 abstract 1
- 244000296796 Glycyrrhiza glabra var. glandulifera Species 0.000 abstract 1
- 230000000857 drug effect Effects 0.000 abstract 1
- 239000000284 extract Substances 0.000 description 8
- 238000010926 purge Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000411851 herbal medicine Species 0.000 description 3
- 229940087646 methanolamine Drugs 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- KSDSYIXRWHRPMN-UHFFFAOYSA-N 4'-O-beta-D-Galactopyranoside-6''-p-Coumaroylprunin-4',5,7-Trihydroxyflavanone Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(C2OC3=CC(O)=CC(O)=C3C(=O)C2)C=C1 KSDSYIXRWHRPMN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 description 1
- 244000303040 Glycyrrhiza glabra Species 0.000 description 1
- DEMKZLAVQYISIA-ONJCETCRSA-N Liquiritin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)c1ccc([C@@H]2Oc3c(C(=O)C2)ccc(O)c3)cc1 DEMKZLAVQYISIA-ONJCETCRSA-N 0.000 description 1
- DEMKZLAVQYISIA-UHFFFAOYSA-N Liquirtin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(C2OC3=CC(O)=CC=C3C(=O)C2)C=C1 DEMKZLAVQYISIA-UHFFFAOYSA-N 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000002467 anti-pepsin effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 229960003720 enoxolone Drugs 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- -1 glycyrrhetinic acid Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- DEMKZLAVQYISIA-ZRWXNEIDSA-N liquiritin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C([C@H]2OC3=CC(O)=CC=C3C(=O)C2)C=C1 DEMKZLAVQYISIA-ZRWXNEIDSA-N 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- GSZUGBAEBARHAW-UHFFFAOYSA-N sophoraflavone B Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(C=2OC3=CC(O)=CC=C3C(=O)C=2)C=C1 GSZUGBAEBARHAW-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Saccharide Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、甘草からグリチルリチンを抽出する方法に関
する。さらに詳しくは、超臨界二酸化炭素を用いて生薬
甘草からその主成分であるグリチルリチンを抽出する方
法において、特定の共留剤を共存させることにより、抽
出効率を高める方法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a method for extracting glycyrrhizin from licorice. More specifically, the present invention relates to a method of increasing the extraction efficiency by coexisting a specific entrainer in a method of extracting glycyrrhizin, the main component of the herbal medicine licorice, using supercritical carbon dioxide.
（従来の技術及びその問題点）
従来、生薬甘草からグリチルリチンを抽出する場合には
、有機溶媒や希アルカリ水溶液のような溶媒を用いる溶
媒抽出法によって抽出していた。(Prior Art and its Problems) Conventionally, glycyrrhizin has been extracted from the herbal medicine licorice by a solvent extraction method using a solvent such as an organic solvent or a dilute alkaline aqueous solution.
しかし、この方法では溶媒の除去に多くの時間とエネル
ギーを必要とするという問題がある。However, this method has a problem in that it requires a lot of time and energy to remove the solvent.
従って、溶媒抽出法に関するかかる問題点を回避するた
めに、最近、超臨界流体、特に超臨界二酸化炭素を用い
て抽出する方法が提案されている。Therefore, in order to avoid such problems with solvent extraction methods, extraction methods using supercritical fluids, particularly supercritical carbon dioxide, have recently been proposed.
この方法は、超臨界状態にある流体特に二酸化炭素が、
多くの物質に対して高い溶解性を示し、しかもその溶解
性が温度、圧力の変化によって変化するという特性を有
することを利用するものであって、抽出技術としてのこ
れからの応用が期待されている。In this method, a fluid in a supercritical state, especially carbon dioxide, is
It shows high solubility in many substances and utilizes the property that its solubility changes with changes in temperature and pressure, and is expected to be applied as an extraction technology in the future. .
しかし、この方法で抽出できる物質は、極性が比較的低
いもののみであり、極性が比較的高い物質の抽出に対し
てこの方法を応用する場合には、共留剤としてメタノー
ル、エタノールもしくはアセトンまたはこれらと水との
混合物を共存させた溶媒を使用するなどの工夫がなされ
ている。However, the substances that can be extracted using this method are only those with relatively low polarity, and when applying this method to the extraction of relatively highly polar substances, methanol, ethanol, acetone, or Efforts have been made to use a solvent containing a mixture of these and water.
ただし、グリチルリチンを甘草から抽出する場合には、
これらの溶媒を共留剤として使用してもなお、抽出でき
ないという問題点があった。However, when extracting glycyrrhizin from licorice,
Even if these solvents were used as entrainers, there was still a problem that extraction could not be performed.
（発明が解決しようとする課題）
従って、本発明の目的は、上記の従来技術の問題点を解
消し、グリチルリチンのように極性の高い物質の抽出を
、上記の超臨界二酸化炭素を用いる抽出方法を利用して
行なえるような方法を提供することにある。(Problems to be Solved by the Invention) Therefore, an object of the present invention is to solve the problems of the above-mentioned prior art, and to extract highly polar substances such as glycyrrhizin using the above-mentioned extraction method using supercritical carbon dioxide. The purpose is to provide a method that can be used to do this.
（課題を解決するための手段）
本発明の目的は、超臨界二酸化炭素を用いて甘草からグ
リチルリチンを抽出する方法において、超臨界二酸化炭
素中に、共留剤として、メタノールと有機アミンとの混
合物を共存させて抽出する方法によって達成することが
できる。(Means for Solving the Problems) An object of the present invention is to provide a method for extracting glycyrrhizin from licorice using supercritical carbon dioxide, in which a mixture of methanol and an organic amine is added as an entrainer to supercritical carbon dioxide. This can be achieved by a method of coexistence and extraction.
甘草（カンゾウ）は、Ｇｌｙｃｙｒｒｈｉｚａ ｇｌａ
ｂｒａ Ｌ。Licorice is Glycyrrhiza gla
bra L.
ｖａｒ、ｇｌａｎｄｕｌｉｆｅｒａ Ｒｅｇｅｌ ｅｔ
Ｈｅｒｄｅｒ、Ｇｌｙｃｙｒｒｌ＋＋ｚａｕｒａｌｅ
ｎｓｉｓ Ｆｉｓｃｈｅｒ又はその他同属植物（Ｌｅｇ
ｕ＋ｎｉ口ｏｓａｅ）の根及びストロンであり、主成分
のグリチルリチン（酸）の他、グリチルレチン酸、グラ
ブラ酸、リキリチン等の多くの化合物が成分として明ら
かにされている。var, glandulifera Regel et.
Herder, Glycyrrl++zaurale
nsis Fischer or other congenerous plants (Leg.
In addition to the main component glycyrrhizin (acid), many other compounds such as glycyrrhetinic acid, glavulic acid, and liquiritin have been revealed as components.
主成分のグリチルリチンＣ４２Ｈ６２０１６は、甘草中
に６〜１４％含まれ、ショ糖の１５０倍の甘さがあり、
甘味料どして用いられる他、生薬としても有名である。The main component, glycyrrhizin C42H62016, is contained in licorice at 6-14% and is 150 times sweeter than sucrose.
In addition to being used as a sweetener, it is also famous as a herbal medicine.
薬効としては、抗消化諸性潰瘍作用、鎮咳作用、抗炎症
作用、抗アレルギー作用、抗ウィルス作用、肝臓機能増
進作用等数多くのものが確認されている。Many medicinal effects have been confirmed, including anti-peptic ulcer, antitussive, anti-inflammatory, anti-allergic, anti-viral, and liver function enhancing effects.
本発明の方法は、超臨界ガス抽出分離装置を用いて行な
われる。超臨界ガスとしては、超臨界状態にある二酸化
炭素を用いる。この二酸化炭素中に共存させる共留剤と
してのメタノールと有機アミンとの混合物は、超臨界状
態の二酸化炭素の気体に対して５〜２０容量％の割合が
好ましく、特に約２０容１％が好ましい。The method of the invention is carried out using a supercritical gas extraction separation device. Carbon dioxide in a supercritical state is used as the supercritical gas. The mixture of methanol and organic amine as an entrainer coexisting in carbon dioxide preferably has a ratio of 5 to 20% by volume, particularly preferably about 20% by volume, based on the carbon dioxide gas in a supercritical state. .
また有機アミンとしては、特にトリメチルアミン及びト
リエチルアミンが好ましい。Further, as the organic amine, trimethylamine and triethylamine are particularly preferred.
さらに、この共留剤中のメタノールと有機アミンとの混
合比は容量比で１：１〜ｌＯ：１が適当であり、好まし
くは２：１〜３：１である。Furthermore, the mixing ratio of methanol and organic amine in this entrainer is suitably 1:1 to 1O:1, preferably 2:1 to 3:1 in terms of volume.
本発明の方法は、二酸化炭素の超臨界状態を達成でき・
るような圧力及び温度において実施され、例えば４００
ｋｇ／ ｃｄの圧力及び４０℃の温度において実施す
ることができる。The method of the present invention can achieve a supercritical state of carbon dioxide.
For example, 400
It can be carried out at a pressure of kg/cd and a temperature of 40 °C.
抽出時間は、実施時の圧力及び温度によって異なるが、
−船釣には、１〜４時間、好ましくは２〜３時間である
。Extraction time varies depending on the pressure and temperature used, but
- For boat fishing, 1 to 4 hours, preferably 2 to 3 hours.
抽出されたエキスについては、通常の分離・精製方法を
用いて、目的物質のみを採取することができる。Regarding the extracted extract, only the target substance can be collected using normal separation and purification methods.
実施例１
超臨界ガス抽出分離装置内に満たされた二酸化炭素中に
、メタノールとトリエチルアミンとの容量比で２：ｌの
混合物を二酸化炭素に対して２０容暑％の割合で混合し
、４００ ｋｇ／ ｃｄの圧力、４０℃の温度にふいて
甘草（２５ｇ）の抽出を行なった。Example 1 A mixture of methanol and triethylamine with a volume ratio of 2:1 was mixed in a carbon dioxide filled in a supercritical gas extraction separation device at a ratio of 20% by volume to carbon dioxide, and 400 kg was mixed. Licorice (25 g) was extracted by wiping at a pressure of /cd and a temperature of 40°C.
計４時間の抽出の間、２時間目までは３０分毎に、２時
間目以降は６０分毎に抽出物を捕集し、抽出エキスを６
回分取した。During a total of 4 hours of extraction, the extract was collected every 30 minutes until the 2nd hour, and every 60 minutes after the 2nd hour.
A batch was collected.
最後に超臨界ガス抽出分離装置をアルコールで洗浄した
際に得られたエキスをパージとして捕集した。Finally, the extract obtained when the supercritical gas extraction and separation device was washed with alcohol was collected as a purge.
捕集した各抽出エキスについては高速液体クロマトグラ
フィーを用いてグリチルリチンの定量を行なった。Glycyrrhizin was quantified in each of the collected extracts using high performance liquid chromatography.
装置はポンプに５Ｐ８７００、カラムにＯＤＳカラム（
４，６φＸ２５０ｍ１＞、ディテクターはＵＶディテク
ター（２５４０ｍ）を使用し、インティグレータ−３ｉ
ｃ ７０００Ｂでデータ処理を行なった。The device has a 5P8700 pump and an ODS column (
4,6φX250m1>, the detector uses a UV detector (2540m), and the integrator
Data processing was performed using a c7000B.
溶媒として、アセトニ） ＩＪル；３％酢酸水溶液を用
い、その混合比が（２： ８）から６０分後には（８：
２）になるように直線グラジェントをかけ流速１＋＋
＋１！／分となるようにした。A 3% acetic acid aqueous solution was used as the solvent, and the mixing ratio changed from (2:8) to (8:8) after 60 minutes.
2) Apply a linear gradient so that the flow rate is 1++
+1! / minute.
得られたエキスの重量と、その中に含まれていたグリチ
ルリチンの含量について、下記表１に示す。The weight of the obtained extract and the content of glycyrrhizin contained therein are shown in Table 1 below.
比較例１
最初の１時間は、二酸化炭素のみで、１時間経過後は二
酸化炭素中に２０容量％のトリメチルアミンを加えた以
外は、実施例１と同様にして抽出を行なった。ただし、
抽出時間は３時間とし、１時間目以降は３０分毎にエキ
スを抽出した。Comparative Example 1 Extraction was carried out in the same manner as in Example 1, except that for the first hour, only carbon dioxide was used, and after one hour, 20% by volume of trimethylamine was added to the carbon dioxide. however,
The extraction time was 3 hours, and after the first hour, extracts were extracted every 30 minutes.
得られたエキスの重量とグリチルリチンの含量について
、下記表２に示す。The weight and glycyrrhizin content of the obtained extract are shown in Table 2 below.
表 １
０ −０．５
０、５−１
１ −１．５
１゜５−２
パージ
６．０
１．１
０．７
０．２
０、 １
０、 Ｑ
Ｏ，４
４６４、０
９９，９
３０，２
９，５
０，４
痕跡量
４０．５
７．６
８．９
４．０
３．３
０．２
９゜
０、１
表
出し、２時間経過時から４時間経過時までは、二酸化炭
素中に２０容量％のメタノールとトリエチルアミンの容
量比で３：１の混合物を混合して抽出した。他の条件及
び操作は、実施例１と同様にした。ただし、１時間目以
降は、３０分毎にエキスを抽出した。Table 1 0 -0.5 0,5-1 1 -1.5 1゜5-2 Purge 6.0 1.1 0.7 0.2 0, 1 0, Q O,4 464, 0 99,9 30,2 9,5 0,4 Trace amount 40.5 7.6 8.9 4.0 3.3 0.2 9゜0,1 Exposed, from 2 hours to 4 hours, carbon dioxide Extraction was carried out by mixing a mixture of 20% by volume methanol and triethylamine in a 3:1 volume ratio in carbon. Other conditions and operations were the same as in Example 1. However, after the first hour, the extract was extracted every 30 minutes.
結果を表３に示す。The results are shown in Table 3.
実施例２
最初の１時間は二酸化炭素のみにより、１時間経過時か
ら２時間経過時までは、二酸化炭素中に２０容量％のメ
タノールを混合したものにより抽表
Ｏ２
０，１０
痕跡量
パージ
０．４５
３９．４
８．７６
表
パージ
０．８３
９０．８
１０．９４
実施例３
メタノールとトリメチルアミンとの２；１の混合物
（容量比）
を共留剤として用いた他は、
実施
例２と同じようにして抽出した。Example 2 For the first 1 hour, only carbon dioxide was used, and from 1 hour to 2 hours, a mixture of 20% by volume of methanol in carbon dioxide was used to purge 0.10 trace amounts of O2. 45 39.4 8.76 Table purge 0.83 90.8 10.94 Example 3 Same as Example 2 except that a 2:1 mixture (volume ratio) of methanol and trimethylamine was used as the entrainer. It was extracted in this way.
結果を表４に示す。The results are shown in Table 4.
実施例４ メタノールとトリエチルアミンとの２＝１の混合物 （容量比） を共留剤として用いた他は、 実施 例２と同じようにして抽出した。Example 4 2=1 mixture of methanol and triethylamine (capacity ratio) In addition to using as an entrainer, implementation Extraction was carried out in the same manner as in Example 2.
結果を表５に示す。The results are shown in Table 5.
パージ
１．３７
８６．６
６．３２
（発明の効果）
以上説明したように、本発明によれば、従来の溶媒抽出
法における問題点を解決した超臨界ガス抽出法を利用で
き、しかもグリチルリチンを高効率に抽出することがで
きる。Purge 1.37 86.6 6.32 (Effects of the Invention) As explained above, according to the present invention, it is possible to use a supercritical gas extraction method that solves the problems of conventional solvent extraction methods, and also to remove glycyrrhizin. Can be extracted with high efficiency.
Claims (3)
チンを抽出する方法において、 超臨界二酸化炭素中にメタノール及び有機アミンの混合
物を共留剤として共存させて抽出することを特徴とする
抽出方法。(1) A method for extracting glycyrrhizin from licorice using supercritical carbon dioxide, which is characterized in that the extraction is carried out in the presence of a mixture of methanol and an organic amine as an entrainer in supercritical carbon dioxide.
ルアミンである請求項（１）に記載の抽出方法。(2) The extraction method according to claim (1), wherein the organic amine is triethylamine or trimethylamine.
１：１〜１０：１である請求項（１）または（２）に記
載の抽出方法。(3) The extraction method according to claim (1) or (2), wherein the mixing ratio of methanol and organic amine is 1:1 to 10:1 by volume.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1046954A JPH02225491A (en) | 1989-02-28 | 1989-02-28 | Method for extracting glycyrrhizin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1046954A JPH02225491A (en) | 1989-02-28 | 1989-02-28 | Method for extracting glycyrrhizin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02225491A true JPH02225491A (en) | 1990-09-07 |
Family
ID=12761683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1046954A Pending JPH02225491A (en) | 1989-02-28 | 1989-02-28 | Method for extracting glycyrrhizin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02225491A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6737254B2 (en) | 1991-07-05 | 2004-05-18 | Bristol-Myers Squibb Company | Supercritical extraction of taxanes |
| US6811796B2 (en) * | 2002-04-22 | 2004-11-02 | Matsuura Yakugyo Co., Ltd. | Preventive or therapeutic agent for pollen allergy, allergic rhinitis, atopic dermatitis, asthma or urticaria, or health food for prevention or improvement or reduction of symptoms thereof |
-
1989
- 1989-02-28 JP JP1046954A patent/JPH02225491A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6737254B2 (en) | 1991-07-05 | 2004-05-18 | Bristol-Myers Squibb Company | Supercritical extraction of taxanes |
| US6811796B2 (en) * | 2002-04-22 | 2004-11-02 | Matsuura Yakugyo Co., Ltd. | Preventive or therapeutic agent for pollen allergy, allergic rhinitis, atopic dermatitis, asthma or urticaria, or health food for prevention or improvement or reduction of symptoms thereof |
| US7452557B2 (en) | 2002-04-22 | 2008-11-18 | Original Image Co., Ltd. | Preventive or therapeutic agent for pollen allergy, allergic rhinitis, atopic dermatitis, asthma or urticaria, or health food for prevention or improvement or reduction of symptoms thereof |
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