JPS60501456A - Method for separating allergens from arnica flowers by CO↓2 high-pressure extraction - Google Patents

Method for separating allergens from arnica flowers by CO↓2 high-pressure extraction

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JPS60501456A
JPS60501456A JP59502195A JP50219584A JPS60501456A JP S60501456 A JPS60501456 A JP S60501456A JP 59502195 A JP59502195 A JP 59502195A JP 50219584 A JP50219584 A JP 50219584A JP S60501456 A JPS60501456 A JP S60501456A
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arnica
extraction
allergens
flowers
separating
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JPH0460451B2 (en
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プフアイフアー，ハンス
ゲーベル，ゲルト
ヴエルゲ，ヴイルフリート
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エア・プロダクツ・アンド・ケミカルズ・インコ−ポレイテッド
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0203—Solvent extraction of solids with a supercritical fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/35—Allergens
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Abstract

(57)【要約】本公報は電子出願前の出願データであるため要約のデータは記録されません。 (57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

【発明の詳細な説明】 ＣＯ２高圧抽出によってアルニカ花からアレルゲンを分離する方法 技術分野 本発明は、Ｃ０２高圧抽出によってアルニカ花Ｄ・らアレルゲンを分離する方法 に関する。[Detailed description of the invention] Method for separating allergens from arnica flowers by CO2 high-pressure extraction Technical field The present invention provides a method for separating arnica flower D. allergens by C02 high-pressure extraction. Regarding.

合量技術 アルニカ・モンタナ（Ａｒｎ１ｃａ　ｍｏｎｔａｎａ　）　ＴＪ、　（キク科） は、数世紀以来中央ヨーロッパの薬室の中の極めて重要な薬用植物の一つである 。アルニカ花（Ｆ１６ｒｅｓＡｒｎｉｃａｅ　）　Ｋついては、全ドイツ薬局方 に単行文が見出される。多数のアルニカ製剤はアルニカ・モンタナの抽出物を含 有している。アルニカ製剤の適用の重点は外部使用である。作用は防腐性、消炎 性及び血液凝固促進性であると特徴づけられている。従ってアル圧力抽出物は就 中創傷治療軟膏においで使用されるが、し力・しまた毛髪用油、ローション、薬 草シャンプーにおいても使用される。内部適用の場合には、呼吸及び循環促進性 ならびに吸収促進性が認められている。Combined amount technology Arnica montana (Arn1ca montana) TJ, (Asteraceae) is one of the most important medicinal plants in the medicinal herb of Central Europe since several centuries. . Arnica flower (F16resArnicae) K, all German Pharmacopoeia A single line sentence is found in . Many arnica preparations contain extracts of Arnica montana. have. The emphasis of the application of arnica preparations is external use. Effects are antiseptic and anti-inflammatory It has been characterized as having anticoagulant and procoagulant properties. Therefore, the alkaline pressure extract is It is used in wound treatment ointments, hair oils, lotions, and medicines. Also used in grass shampoos. Respiratory and circulatory properties for internal application It is also recognized to have absorption promoting properties.

アルニカ製剤の薬理作用は、特定の含有物質、就中精油、フラぎノイドグリコシ ド及び最近の研究で見出されたセスキチル４ンラクトンに起因する。アルニカ花 の含有物質に関する詳細な論文は、雑誌゛′ファルマツィー、イン、ウンゼレル ・ツアイト（Ｐｈａｍａｚｉｅ　１ｎｕｎｓｅｒｅｒ　Ｚｅｉｔ　）　”、第１ ０巻、１〜７頁（１９８１）し力）しアルニ力抽出物、例えばアルニカテンキを 不適切に適用すると、アレルギー性接触皮膚炎の危険が生じる。このような症例 は、”デル・ハウトアールット　（Ｄｅｒ　Ｈａｕｔ　ａｒｚｔ　）　”　、１ ０〜１７　頁　（１９８０）に多数記載されている。接触アレルゲンとしては、 セスキチルインラクトン、ヘレナリン、ヘレナリ／アセテート及びヘレナリンー メタクリレートが挙げられている。The pharmacological effects of arnica preparations are determined by the specific substances they contain, especially essential oils, and fraginoid glycosides. This is due to the sesquitil lactone found in recent studies. arnica flower A detailed article on the substances contained in ・Zeit (Phamazie 1nunserer Zeit)”, 1st Vol. 0, pp. 1-7 (1981) and extracts of arnica, e.g. Improper application creates a risk of allergic contact dermatitis. Cases like this is "Der Haut arzt", 1 Many are described on pages 0 to 17 (1980). As a contact allergen, Sesquitylin lactone, helenalin, helenary/acetate and helenalin- Methacrylate is mentioned.

ところで、液状ＣＯ２を用いるアルニカ花の適当な処理によって、前記セスキチ ル波ンラクトンを、薬理作用にとって重要な他の含有物質、すなわちフラボノイ ドグリコシド及び精油の一部を一緒に捕捉することなく、定量的に抽出すること ができることが見出された発明の開示 したがって本発明の対象は、アルニカ花からアレルゲンを分離するに当り、乾燥 アルニカ花に３１〜９０℃及び７０〜５００パールで臨界超過ｃｏ２’ｚ用いて 高圧抽出を施しかつ溶出されたアレルゲン物質及び場合によっては同伴抽出され た精油を圧力及び／又は温度低下によって分離することを特徴とする前記アレル ゲンの分離方法である。、 抽出のために、乾燥アルニカ花を例えば滑りローラーを用いて高圧で粉砕するこ とによって砕解してもよい。しかしこの場合には、アレルゲンのセスキチルイン ラクトンの他に精油が定量的に抽出されろという欠点がある。従って未粉砕花に 抽出を施すのが有利であって、この場合にはセスキテルペンラフ　トン分は同ｍ に定量的に抽出されるけれども、精油の主要部分は薬理作用を有する他の物質と 共に被抽出薬種の中に残存している。これは通常アレルゲンを含１ないアルニカ 抽出物、チンキ等つ抽出製造に用いられる。By the way, by appropriately treating arnica flowers using liquid CO2, the sesquichi Luvan lactone is combined with other compounds important for its pharmacological action, namely flavonoids. Quantitative extraction of doglycosides and essential oils without trapping them together Disclosure of inventions found to be capable of Therefore, the object of the present invention is to use dried Arnica flowers using supercritical CO2'z at 31-90℃ and 70-500 pearls High-pressure extraction and eluted allergens and, in some cases, entrained extraction The above allele is characterized in that the essential oil is separated by pressure and/or temperature reduction. This is a method for separating gens. , For extraction, dried arnica flowers can be crushed under high pressure, e.g. using sliding rollers. It may be disintegrated by However, in this case, the allergen sesquitylin The disadvantage is that essential oils in addition to lactones must be quantitatively extracted. Therefore unmilled flowers It is advantageous to carry out extraction, in which case the same ton of sesquiterpene rough Although the essential oil is quantitatively extracted from the Both remain in the extracted drug species. This is usually allergen-free arnica. Used in the production of extracts, tinctures, etc.

二酸化炭素を用いて圧力下に抽出を行うことは原理的には公知であって、多数の 文献、例えばケミストリー・アンド・インダストリー（Ｃｈｅｍｉｓｔｒｙ　ａ ｎ４工ｎｄｕｓｔｒｙ　）　１２．３８５〜４０５頁（１９８２）ならびにヨー ロッパ特許第２３６８０号及゛び同第５８３６５号明細書に記載されている。Extraction under pressure using carbon dioxide is known in principle, and there are many Literature, e.g. Chemistry and Industry n4 engineering) 12. pp. 385-405 (1982) and It is described in Roppa Patent Nos. 23680 and 58365.

抽出は、７０〜５００パール、好ましくは３００パールの圧力でかつ３１〜９０ ℃の温度、好ましくは５０〜７０℃で臨界超過Ｃ０２を用いて行われる。抽出物 の分離は圧力及び温度低下によって行われる。未粉砕薬種の抽出所要時間は約３ 〜６時間である。The extraction is carried out at a pressure of 70-500 pars, preferably 300 pars and 31-90 pars. It is carried out using supercritical C02 at a temperature of 0.degree. C., preferably from 50 to 70.degree. extract Separation of is carried out by pressure and temperature reduction. The extraction time for unpulverized medicinal species is approximately 3 ~6 hours.

抽出前及び後の薬種中の含有物質の測定は薄層クロマトグラフィーにより定量的 に行われる。抽出の完全度は００２−抽出物の相応の検査によって判断すること ができる。Quantitative measurement of substances contained in drug species before and after extraction using thin layer chromatography It will be held on. The completeness of the extraction shall be judged by corresponding examination of the 002-extract. Can be done.

フラボノイドグリコシド検査は原則的にはＤＡＢ　７　（付録２．１１６頁以下 ）Ｉｃより行う：乾燥アルニヵ花（アルニヵ・モンＩｔ　、Ｆｌｏｓ　）　Ｋ、 フラボノイド検査のためにメタノール（薬種１ｇ当りメタノール２０−）を用い て抽出を施す。次に濾過し、濾液を蒸発濃縮して２−とする。この抽出液をクロ ロホルム／メタノール（３：１）中に溶かす。試料１００μ］？：珪酸ゲル”　 ２５４板上にスポットしかつ酢酸エチル／蟻酸（無水）／酢酸／Ｈ２０（１００ ：１１：１１：２６）で展開して薄層クロマトグラフィー２行う。検出はメタノ ール中のジフェニルボリルオキ／エチルアミンの１％溶液を噴霧して行う。In principle, the flavonoid glycoside test is based on DAB 7 (Appendix 2, from page 116 onwards). ) From Ic: Dried arnica flowers (Arnica mon It, Flos) K, Methanol (20 − methanol per 1 g of drug) was used for flavonoid testing. Perform extraction. It is then filtered and the filtrate is evaporated to give 2-. This extract was chlorinated. Dissolve in loform/methanol (3:1). Sample 100μ]? :Silicate gel” 254 plate and ethyl acetate/formic acid (anhydrous)/acetic acid/H20 (100 :11:11:26) and perform thin layer chromatography 2. Detection is methano This is done by spraying a 1% solution of diphenylboryl oxy/ethylamine in a bottle.

セスキテルペンラクトン検査は、ｃ、ヴイルウーン（Ｗｉｌｌｕｈｎ　）及びＨ ，Ｄ、シエーフエル（Ｓ’ｃｈＭｆｅｒ　）、ファルマツオイティッ／工・ツァ イトウング（ＰｈａｒｍａｚｅｕｔｉｓｃｈｅＺｅｉｔｕｎｇ　）　１２３．１ ８０３〜１８０８頁（１９７８）により行うことができ７）： 薬種つ１才り抽出後の残存物５ｇにペンゾール４　Ｑ　ｍｅを用いて１０分間低 温抽出を施し、濾過しかつペンゾール５−で後洗浄する。ペンゾール抽出液を６ ０〜７０℃で蒸発濃縮し、残留物から６０％エタノール３０ｍ１を用いて振出を 行い、次に濾過する。Ｃｏ２−抽出物（］−００ｍ９　）をペンゾール１０ｍ１ 中に熱時に溶がし、濾過しかつ同量の６０％エタノールを用いて小回振出を施す 。Sesquiterpene lactone tests include C, Willuhn and H , D, S'chMfer, Farmatuoiiti Pharmazeutische Zeitung 123.1 803-1808 (1978) 7): Add Penzol 4Qme to 5g of the residue after extracting the drug for 10 minutes. Hot extraction is carried out, filtered and after-washed with Penzol 5-. 6 Penzol extract Evaporate and concentrate at 0 to 70°C, and shake out the residue using 30ml of 60% ethanol. and then filter. Co2-extract (]-00m9) in Penzol 10ml Dissolve in hot water, filter, and give a small shake using the same amount of 60% ethanol. .

エタノールを除去しかつ水相を補充して２０　ｍｌにした後、それぞれ５−のク ロロホルムで５回珈出乞行つ。After removing the ethanol and replenishing the aqueous phase to 20 ml, each Begged for coffee 5 times in Roroform.

集めたクロロホルム抽出液を（ｊａｃｌ　により脱水しがっ蒸発濃縮する。黄色 同伴物質を除去するために、残留物をペンゾール０．５−中に取わ、中性酸化ア ルミニウム９０〔メルク（Ｍｅｒｃｋ　）社、活性段階１）２０ｇＫより石ｍエ ーテル／インゾール／クロロホルム／メク／−ル（５：４：ｌ：２）混合物を用 いてクロマトグラフィーを行う。溶離液の最初の：ｔｏｍｚｖ棄てる。次の２０ −を蒸発乾固し、ＤＣ分析のためにペンゾール０．３−中に取る。The collected chloroform extract was dehydrated with (jacl) and concentrated by evaporation. To remove entrained substances, the residue was taken up in Penzol 0.5- and neutral oxidized Luminium 90 (Merck, active stage 1) from 20gK Using a mixture of ester/inzole/chloroform/mek/l (5:4:l:2) Perform chromatography. Discard the first: tomzv of eluent. next 20 - is evaporated to dryness and taken up in Penzol 0.3- for DC analysis.

試料（２０−３０μｍ）を珪酸ゲルＦ２５４−薄層板（メルク社）上にスポット しかつｎ−ペンタン／エーテル（８：１７）で展開する。検出は、ツィンメルマ ン（Ｚｉｍｍｅｒｍａｎｎ　）試薬〔エタノール中のｍ−ジニトロペンゾール及 び１２５ＮｘｏＨ（１：　１　）の２％溶液〕を噴霧した後紫外線下で行う。Spot the sample (20-30 μm) onto a silicate gel F254-thin plate (Merck & Co.) and developed with n-pentane/ether (8:17). Detection is Zimmermer Zimmermann reagent [m-dinitropenzole and and 2% solution of 125NxoH (1:1)] under UV light.

精油の含量測定はＤＡＢ　１３により行う。The essential oil content is measured using DAB 13.

実施例 例１ 精油０．１２−／ｌｏｏｇを含有する未粉砕乾燥アルニカ花１０００＃を、高圧 抽出装置の抽出容器中で温度７０℃及び圧力３００パールで６時間抽出した。分 離は２０℃及び６０パールで行った。Example Example 1 1000 # of unpulverized dried arnica flowers containing essential oil 0.12-/loog were heated under high pressure. Extraction was carried out for 6 hours at a temperature of 70° C. and a pressure of 300 par in the extraction vessel of the extractor. minutes Detachment was carried out at 20° C. and 60 pars.

枯草風の芳香を有する黄褐色のイースト状抽出物がが分離され、デカンテーショ ン及び絞出しによって除去された。抽出物及び被抽出薬種の分析により次の結果 が得られた： ａ）抽出物 精油：０．０６．ｄ／１０ｏｙの乾燥原料水　：３．１ｍＪ／１００．９の乾燥 原料セスキテルペンラクトン：薄層クロマトグラフィーにより検出できる フラぎノイドグリコンＰ：検出できな℃・ｂ）被抽出薬種 セスキテルペンラクトン：微量しが検出できないフラｉ？　／イドグリコンド： 薄層クロマトグラフィー等が検出できる 精油：　０．０５ｍ／１００　、Ｓ＋の破抽出薬種例２ 乾燥アルニカ花１０００Ｅｖ、滑りローラーを用いて圧力６０ｔで砕解し、次に ７０℃、３００パー、１でこれに４時間抽出を施した。分離は２２℃、６５パー ルで行った。A yellow-brown yeasty extract with a hay-like aroma is isolated and decanted. removed by pressing and squeezing. The following results were obtained from the analysis of the extract and the extracted drug species. was gotten: a) Extract Essential oil: 0.06. d/10oy dry raw water: 3.1mJ/100.9 drying Raw material sesquiterpene lactone: Can be detected by thin layer chromatography Fraginoid glycon P: undetectable °C b) Extracted drug species Sesquiterpene lactone: A trace amount that cannot be detected? /Idgricondo: Can be detected by thin layer chromatography, etc. Essential oil: 0.05m/100, S+ extraction drug type example 2 Dried arnica flowers were crushed at 1000 Ev using a sliding roller at a pressure of 60 tons, and then This was subjected to extraction for 4 hours at 70° C. and 300 par. Separation at 22°C, 65% I went by le.

抽出物６−５重量％及び水２５−が分離された。水はでカンチージョン及び絞出 しによって除去した。6-5% by weight of extract and 25% of water were separated. Kancheejeong and squeezed water It was removed by scrubbing.

抽出物は、セスキチルにンラクトン全量及び精油１）表１１１ＨＧＯ−５０１４ ５Ｇ　（３）２．２ｄ／ｌｏｏ、ｆＪ　（０，１４−／１００．９（７）乾燥原 料に相当する）を含有していた。７ラゼノイドグリコンドは検出できなかった。The extract contains the total amount of sesquitil lactone and essential oil 1) Table 111 HGO-5014 5G (3) 2.2d/loo, fJ (0,14-/100.9(7) Dry field ). 7 lazenoid glycocond could not be detected.

被抽出薬種にはもはやセスキチル啄ンラクトンは検出できず、他方精油の含量は ０．０２　ｄ　／　１００　ｇであった。フラゼノイドグリコシドは完全に得ら れた。Sesquitilactin lactone can no longer be detected in the extracted drug species, while the content of essential oil is It was 0.02 d/100 g. Frazenoid glycosides are completely obtained It was.

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Claims (1)

【特許請求の範囲】 １　アルニ力花からアレルゲンを分離するに当り、乾燥アル二カ花に、３１〜９ ０℃及び７０〜５００パールで臨界超過Ｃｏ２乞用いて高圧抽出を施しかつ溶出 されたアレルゲン物質及び場合によっては同伴抽出された精油を圧力及び／又は 温度低下によって分離することを特徴とするアルニカ花からアレルゲンを分離す る方法。 ２　分離を５０〜７０℃及び３００パールで実施する請求の範囲第１項記載の方 法。 ３　抽出のために未粉砕乾燥アルニカ花を使用する請求の範囲第１項又は第２項 記載の方法。 牛　乾燥アル二カ花からアレルゲンのセスキテルペンラクトン乞分離する請求の 範囲第１項から第３項１でのいづれか１項に記載の方法。 ５　アレルゲン乞含まないアルニカ花薬種を製造する請求の範囲第１項から第４ 項１でのいづれか１項に記載の方法。[Claims] 1. In separating allergens from Arnica flowers, 31 to 9 High-pressure extraction and elution using supercritical CO2 at 0°C and 70-500 par. Pressure and/or Separation of allergens from arnica flowers, which is characterized by separation due to temperature reduction. How to do it. 2. The person according to claim 1, in which the separation is carried out at 50 to 70°C and 300 par. Law. 3. Claim 1 or 2 in which unground dried arnica flowers are used for extraction. Method described. Cattle claim that allergenic sesquiterpene lactones are separated from dried Arnica flowers. The method according to any one of the ranges 1 to 3, 1. 5. Claims 1 to 4 for producing Arnica flower medicinal seeds that do not contain allergens. The method described in any one of Section 1.
JP59502195A 1983-05-27 1984-05-19 Method for separating allergens from arnica flowers by CO↓2 high-pressure extraction Granted JPS60501456A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19833319184 DE3319184A1 (en) 1983-05-27 1983-05-27 METHOD FOR SEPARATING ALLERGENS FROM ARNICA BLUETES BY MEANS OF CO (ARROW DOWN) 2 (ARROW DOWN) HIGH PRESSURE EXTRACTION
DE3319184.0 1983-05-27

Publications (2)

Publication Number Publication Date
JPS60501456A true JPS60501456A (en) 1985-09-05
JPH0460451B2 JPH0460451B2 (en) 1992-09-28

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JP59502195A Granted JPS60501456A (en) 1983-05-27 1984-05-19 Method for separating allergens from arnica flowers by CO↓2 high-pressure extraction

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EP (1) EP0144368A1 (en)
JP (1) JPS60501456A (en)
DE (1) DE3319184A1 (en)
ES (1) ES532847A0 (en)
IT (1) IT1180170B (en)
WO (1) WO1984004683A1 (en)

Families Citing this family (8)

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Publication number Priority date Publication date Assignee Title
IT1190129B (en) * 1986-06-17 1988-02-10 Indena Spa OILAGINOUS FRUITS EXTRACTION PROCEDURE
DE3637826C1 (en) * 1986-11-06 1988-05-11 Hopfenextraktion Hvg Barth Process for extracting natural dyes from walnut shells and henna
US4927652A (en) * 1987-12-16 1990-05-22 Lever Brothers Company Process for the extraction of lactones from lipid material
NL8900652A (en) * 1989-03-16 1990-10-16 Leti Lab PRIMARY TOXIC SUBSTANCES OR ALLERGENS, ISOLABLE FROM VEGETABLE MATERIAL, AND METHODS FOR THE PREPARATION AND USE THEREOF.
ATE123947T1 (en) * 1990-07-05 1995-07-15 Indena Spa ECHINACEA EXTRACTS, METHOD OF PREPARATION AND PREPARATIONS CONTAINING THEM.
US5120558A (en) * 1991-05-01 1992-06-09 Norac Technologies Inc. Process for the supercritical extraction and fractionation of spices
CA2072400C (en) 1991-07-05 2003-08-19 Jayaprakash B. Nair Supercritical extraction of taxanes
FR2843125B1 (en) 2002-08-02 2012-11-16 Coletica ACTIVE PRINCIPLES STIMULATING HUMAN BETA-DEFENSIVE TYPE 2 AND / OR TYPE 3, AND COSMETIC OR PHARMACEUTICAL COMPOSITIONS COMPRISING SUCH ACTIVE INGREDIENTS

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5554003A (en) * 1978-10-13 1980-04-21 Hag Ag Extracting treatment method of vegetable and animal material
JPS5655175A (en) * 1979-08-02 1981-05-15 Henkel Kgaa Production of extract of aromatizing agent

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Publication number Priority date Publication date Assignee Title
BE789002A (en) * 1971-09-22 1973-01-15 Sori Soc Rech Ind PROCESS FOR OBTAINING AN EXTRACT OF ARNICA MONTANA
DE3105557A1 (en) * 1981-02-16 1982-09-09 Henkel Kgaa "METHOD FOR OBTAINING INGREDIENTS OF THE CHAMOMILE BY EXTRACTION WITH CARBON DIOXIDE"

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5554003A (en) * 1978-10-13 1980-04-21 Hag Ag Extracting treatment method of vegetable and animal material
JPS5655175A (en) * 1979-08-02 1981-05-15 Henkel Kgaa Production of extract of aromatizing agent

Also Published As

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ES8502864A1 (en) 1985-02-01
WO1984004683A1 (en) 1984-12-06
ES532847A0 (en) 1985-02-01
JPH0460451B2 (en) 1992-09-28
DE3319184A1 (en) 1984-11-29
IT8421097A0 (en) 1984-05-25
IT8421097A1 (en) 1985-11-25
IT1180170B (en) 1987-09-23
EP0144368A1 (en) 1985-06-19

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