WO2013151407A1 - Procédé d'extraction d'huile d'acorus calamus var. angustatus contenant des quantités importantes de bêta-asarone par extraction par fluide supercritique - Google Patents
Procédé d'extraction d'huile d'acorus calamus var. angustatus contenant des quantités importantes de bêta-asarone par extraction par fluide supercritique Download PDFInfo
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- WO2013151407A1 WO2013151407A1 PCT/KR2013/002932 KR2013002932W WO2013151407A1 WO 2013151407 A1 WO2013151407 A1 WO 2013151407A1 KR 2013002932 W KR2013002932 W KR 2013002932W WO 2013151407 A1 WO2013151407 A1 WO 2013151407A1
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- extraction
- iris
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/02—Pretreatment
- C11B1/04—Pretreatment of vegetable raw material
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
- C11B1/104—Production of fats or fatty oils from raw materials by extracting using super critical gases or vapours
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/025—Recovery by solvent extraction
-
- 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
Definitions
- the present invention relates to a method for extracting iris root oil containing a large amount of beta asaron using a supercritical extraction method, more specifically, drying irises; Grinding the dried irises;
- the method relates to a method for extracting an iris oil containing a large amount of beta asaron from an iris comprising extracting the iris powder by a supercritical extraction method using supercritical carbon dioxide and a cosolvent and concentrating the iris extract. .
- Iris ( Acorus calamus var. Angustatus ) is a perennial herb that grows in wetlands and belongs to Tiannan province .
- the habitat is known to extend from Jeju Island to the northern part of Korea. In Korea, it is customary to bathe or wash your hair in water boiled with iris leaves or iris roots on a single day in a three-day period to defeat bad energy.If you wash your hair in water boiled with iris leaves or iris roots, your hair will not fall out. She believed that she was shiny and smooth, and her hair would be long like a window stalk.
- oriental medicine In oriental medicine, it has important effects such as sedation, palliative action, analgesic action, and antifungal action.
- aromatic substance which is widely used as a fragrance for making lotion and high-quality perfume.
- Asarone of 4-propenyl-1,2,5-trimethoxybenzene (C 12 H 16 O 3 , molecular weight 208.254 g / mol) is a major component of root, leaf and stem extracts of Acorus species.
- Korean iris species which are native to Korea, are traditionally contained in large amounts of antibacterial components, and are known to exhibit antimicrobial and insecticidal effects such as treatment of hair dandruff and skin diseases (acne, athlete's foot, eczema, scabies, atopic bacteria, etc.) or food poisoning. Recently, it is used as a chemical sterilizer after steam treatment, and is known as a toxin, a morph modifier or an insect stimulant.
- beta-aron As isomer of asaron, beta-aron ( ⁇ -asarone) is toxic while alpha-asarone ( ⁇ -asarone) has no toxicity and has only anti-freezing activity.
- Asaron is known to be contained in a large amount of irises, among other plants, and irises are native to temperate regions and are aquatic plants native to any region including Jeju Island in Korea. Roots are beard roots, but long, long stems extend into the ground, and roots sprout from the bottom.
- Essential oils contain 0.8 to 5% in the root stem and 0.1 to 0.3% in the leaves, and beta asaron is one of the essential oil components.
- Pharmacological action is used as abortion, analgesic, aphrodisiac, fragrance, puncture, antiperspirant, tonic economy, antipyretic, hallucinogenic drug, homeopathic, sedative, stimulant, tonic or insect repellent.
- Beta asaron extraction from conventional irises has been performed mostly through hot water extraction or methanol solvent extraction.
- the conventional extraction method has a problem in that residual waste and organic solvent remain after extraction.
- the extraction yield of beta asaron is low.
- the inventors grind the irises to 0.5 mm to 1 mm particle size after natural drying and extract a large amount of beta from the irises by supercritical extraction using supercritical carbon dioxide and co-solvent. It was confirmed that the oil containing asaron can be extracted and completed the present invention.
- Another object of the present invention is to provide an iris oil containing beta asaron extracted using the above extraction method.
- the present invention comprises the steps of crushing the iris (step 1); Supercritical extraction of the iris powders using supercritical carbon dioxide and co-solvent at 40 ° C. to 60 ° C. and 200 bar to 400 bar pressure conditions (step 2); And it provides a method for extracting beta-aron containing iris oil comprising the step of concentrating the iris extract (step 3).
- Step 1 is a pretreatment method for increasing the extraction yield of the irises, the crushed irises to a predetermined size.
- the term "Iris” is used as a medicinal herb sprayed with perennial herbaceous plants belonging to Chunnamseong. It is known to have the effects of dry stomach, soothing, jingyeong, and leech, and is used for symptoms such as digestion, diarrhea, wet swelling, jeongan, vigilance, forgetfulness, mental anxiety, customs pain, seawater, bronchitis, carbuncle, and spear.
- the root contains a fragrant substance that is used in the bath water.
- the said iris uses the low temperature cold air drying dried iris.
- cold air drying means a method of drying at low temperature.
- the low temperature means a relatively low temperature, and generally the low temperature means a temperature range of 40 ° C to 60 ° C.
- the low temperature cold wind drying in the present invention can be carried out for several days. It is preferably performed for 1 to 5 days, but may be appropriately adjusted according to the moisture content of the irises.
- the grinding is preferably a pin mill or a low temperature mill, but is not limited thereto.
- the diameter of the iris powder is preferably a size of 0.5 mm to 1 mm.
- the particle size of the pulverized product is out of the range, there is a disadvantage in that the extraction efficiency of the iris is lowered.
- the particle size of less than 0.5 mm the extraction efficiency is lowered due to the pressure load during supercritical extraction, the beta asaron contained in the particles difficult to extract to the outside by the supercritical fluid at the particle size of more than 2 mm have.
- Step 2 is a step of supercritical extraction by adding a co-solvent to the supercritical carbon dioxide in order to extract the iris oil containing beta asaron from the iris.
- the cosolvent is preferably ethanol, but is not limited thereto.
- the cosolvent may use 1 to 10 vol% of the total supercritical fluid mixture, preferably 3 vol% of the total supercritical fluid mixture.
- the supercritical extraction is preferably performed at a temperature of 40 °C to 60 °C, it is preferably carried out at 200 bar to 400 bar pressure conditions.
- a high yield of iris oil supercritical extract of 6.2% was obtained under the extraction conditions of 50 °C and 200 bar, 40 °C and 300 It was confirmed that the iris supercritical fluid extract extracted by the addition of the co-solvent in the extraction condition of bar had a high content of beta asaron of 0.937 g.
- Step 3 is a step of concentrating the iris supercritical extract to remove the cosolvent in the iris extract obtained by extraction.
- the concentration can be carried out using conventional thickeners known in the art.
- the present invention provides a iris oil containing a large amount of beta asaron derived from irises extracted by the above extraction method.
- the method for extracting beta-asarone derived from irises according to the present invention includes supercritical extraction of crushed irises having a particle size of 0.5 mm to 1 mm by adding a co-solvent to a carbon dioxide supercritical fluid, thereby containing a large amount of beta-asarone from irises. It is effective to provide a method for extracting essential oils.
- FIG. 1 shows the addition of 2 ml / min ethanol at 40 ° C. of a 0.5 mm particle size iris mill according to one embodiment of the invention before (a) extraction, (b) after 200 bar supercritical extraction, and (c) Images show the iris extract after 300 bar supercritical extraction and (d) iris powder after extraction at 400 bar and (e) 200 bar extraction, (f) 300 bar extraction and (g) 400 bar extraction.
- FIG. 2 shows the addition of 2 ml / min ethanol at 400 bar of a 2 mm particle size iris mill according to one embodiment of the invention before (a) extraction, (b) after 50 ° C. supercritical extraction and (c) An image showing the iris powder after 60 ° C supercritical extraction and (d) 50 ° C supercritical extraction and (e) 60 ° C supercritical extraction.
- Figure 3 is (a) before extraction, (b) after 200 bar supercritical extraction, (c) after 300 bar supercritical extraction at 50 ° C of 0.5 mm particle size iris powder according to an embodiment of the present invention and ( d) An image showing the iris powder after extraction at 400 bar and (e) 200 bar extraction, (f) 300 bar extraction and (g) 400 bar extraction.
- FIG. 4 shows the addition of 2 ml / min ethanol at 50 ° C. of a 0.5 mm particle size iris mill according to one embodiment of the invention before (a) extraction, (b) after 200 bar supercritical extraction, and (c) Images show the iris extract after 300 bar supercritical extraction and (d) iris powder after extraction at 400 bar and (e) 200 bar extraction, (f) 300 bar extraction and (g) 400 bar extraction.
- Figure 5 (a) change in pressure, temperature change and extraction yield (%) change with or without cosolvent at 0.5 mm particle size according to an embodiment of the present invention, (b) temperature change at 200 bar pressure conditions And change in extraction yield (%) with and without cosolvent, (c) change in extraction yield (%) with temperature change at 300 bar pressure, and (d) temperature change and presence or absence of cosolvent at 400 bar pressure. It is a graph showing the change in extraction yield (%).
- Figure 6 is a graph showing the results of HPLC quantification of (a) 7000 ppm, (b) 700 ppm and (c) 350 ppm for the beta asaron standard according to an embodiment of the present invention.
- FIG. 7 is an image showing a calibration curve measurement result obtained to verify the results of HPLC quantitative analysis by concentration of the beta asaron standard according to an embodiment of the present invention.
- FIG. 10 is a graph showing changes in total content of beta-aron and (b) change in total amount of beta-aron according to pressure change of (a) temperature change of an iris extract according to an embodiment of the present invention.
- the irises inhabiting Hapyeongsan, Korea were naturally dried at 60 ° C. for 5 days and then pretreated by grinding to a size of 0.5 mm to 2 mm using a pin mill.
- Supercritical extraction is controlled at temperatures of 40, 50 and 60 ° C., and the pressure is adjusted to 200, 300 and 400 bar at each temperature condition so that the amount of 100 g of the pretreated irises is extracted using a supercritical extraction device at each extraction condition. And supercritical extraction was performed for 100 minutes for each iris sample. In supercritical extraction, the flow rate was 60 ml / min (supercritical fluid extraction).
- the irises inhabiting Hapyeongsan, Korea were dried at 60 ° C. for 5 days and then ground to a size of 0.5 mm using a grinder. 100 g of the prepared iris was put in 500 ml of a methanol solution, and the extract was supported for 24 hours at a temperature of 60 ° C., and then concentrated by using a vacuum concentrator to completely remove the solvent. Table 2 shows the extraction conditions.
- the extraction yield of the iris extract obtained in the above Examples and Comparative Examples was measured.
- 100 g (A) of the sample was put in the extraction basket, and the weight (B) of the extracted material obtained after the extraction was recorded.
- Extraction yield measurement using cosolvent was carried out using supercritical carbon dioxide and cosolvent, supercritical extract material containing calamus oil was placed in a vacuum concentrator, and solvent was completely removed. 100 g (A ′) was recorded and calculated by the following equation.
- Table 3 The results of Table 3 are shown in FIG. 5 according to temperature and pressure conditions. As shown in Figure 5, it can be seen that the extraction yield of the sample prepared in Example 4 (0.5 mm particle size, 50 °C temperature and 200 bar pressure conditions) was the highest, each pressure condition (200 bar, 300 bar And (b), (c) and (d) of Fig. 5 showing the extraction yield change according to 400 bar) to confirm that the sample using the co-solvent extraction yield (%) is higher than the sample without the co-solvent could.
- HPLC analysis was performed using Waters HPLC with COSMOSIL 5C18MS-II, 250 mm ⁇ 4.6 mm (Nakala Teque, Inc., Japan) column at 10 ⁇ l injection volume and 0.1% formic acid (Fluka) as mobile phase. , USA) and acetonitrile (acetonitrile, JT Baker, USA) were eluted for 45 minutes at a flow rate of 1 ml / min using a concentration gradient (acetonitrile content: 20 wt% to 80 wt%).
- the oven temperature was set at 35 ° C.
- the components of the irises supercritical extracts of Examples 1 to 22 were examined through HPLC analysis, and the results are shown in FIG. 9. As shown in FIG. 9, the extraction yield of the iris extract extracted through Example 4 was 1.9 times higher than that of the methanol extract obtained from Comparative Example 1, and the beta asaron content of the iris extract extracted through Example 2 was obtained. It was confirmed that 1.9 times higher compared with the control Comparative Example 1.
- the iris methanol extract extracted in Comparative Example 1 was used, to determine the concentration of beta asaron contained in iris oil, the sample by concentration using a beta asaron standard solution.
- the chromatograms prepared and obtained through HPLC analysis are shown in FIG. 6.
- the calibration curve for determination of concentration through the chromatogram obtained in FIG. 6 is shown in FIG. 7, and the conditions of the highest extraction yield and the high beta-asone content are shown in FIG. 8.
- Example 4 50 °C, 200 bar and co-solvent use conditions
- the conditions of Example 2 40 °C, 300 bar and co-solvent use) Conditions
- Example 13 the extraction conditions were significantly higher in Example 4 conditions (50 °C, 200 bar and co-solvent use conditions) compared to Example 13 and the control Comparative Example 1 without the co-solvent
- the conditions of Example 2 (40 ° C., 300 bar and cosolvent use conditions) were confirmed to be significantly higher in beta-asarone content in the iris oil than in Example 13 without the cosolvent and Comparative Example 1.
- FIG. 10 Changes in the total content of beta-asarone according to the temperature and pressure conditions of the iris supercritical extract using 0.5 mm particle size except 19 to 22 of Examples 1 to 22 are shown in FIG. 10.
- the highest beta-aronone content was obtained in the extraction conditions using 40 ° C., 300 bar, and the cosolvent prepared in Example 2, and the sample using the cosolvent at the same temperature was used as the cosolvent. It was confirmed that the total extraction content of beta asaron is higher than the sample not used.
- Example 1 to 22 the beta-aronon HPLC measurement concentration and the concentrated sample content of Examples 6, 9, 13, 18, 19, 20, 21, and 22 having a pressure condition of 400 bar were measured. And FIG. 11. As shown in Table 5 and Figure 11, regardless of the extraction temperature and pressure change, when using the particle size of 0.5 mm, the extraction yield was up to 2.4 times higher than that of the particle size of 2 mm, beta asaron The content was also confirmed to be as high as the extraction yield.
- Cheongpo extract obtained in Example 6 showed the highest content of beta asaron, it was confirmed that the amount of extraction decreases slightly with increasing temperature. In addition, it was confirmed that the extraction amount increases as the co-solvent is present and the particle size is small. Therefore, it can be seen that the particle size and the use of the co-solvent is an important factor.
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
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- Medicines Containing Plant Substances (AREA)
- Extraction Or Liquid Replacement (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| KR1020120036330A KR101433771B1 (ko) | 2012-04-06 | 2012-04-06 | 초임계 유체 추출법을 이용한 베타아사론이 다량 함유된 창포 오일 추출 방법 |
| KR10-2012-0036330 | 2012-04-06 |
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| WO2013151407A1 true WO2013151407A1 (fr) | 2013-10-10 |
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| PCT/KR2013/002932 Ceased WO2013151407A1 (fr) | 2012-04-06 | 2013-04-08 | Procédé d'extraction d'huile d'acorus calamus var. angustatus contenant des quantités importantes de bêta-asarone par extraction par fluide supercritique |
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| WO (1) | WO2013151407A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018077013A1 (fr) * | 2016-10-27 | 2018-05-03 | 陕西师范大学 | Procédé d'extraction d'huile supercritique à haut rendement |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101682497B1 (ko) | 2015-07-28 | 2016-12-05 | 주식회사 한빛향료 | 지방함량이 적은 종자의 오일 추출방법 |
| CN106854491A (zh) * | 2016-12-07 | 2017-06-16 | 宁夏农林科学院固原分院 | 一种富硒亚麻籽油及其制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR960016900B1 (ko) * | 1994-01-03 | 1996-12-26 | 삼성전자 주식회사 | 하드디스크드라이브의 액츄에이터 고정장치 |
| KR20050068283A (ko) * | 2003-12-30 | 2005-07-05 | 코스맥스 주식회사 | 석창포 추출물을 포함하는 피부노화방지 조성물 |
| KR20100038029A (ko) * | 2008-10-02 | 2010-04-12 | 인성실업(주) | 초임계 추출에 의하여 크릴 오일을 생산하는 방법 및 오메가-3 지방산 함량이 높은 크일 오일 조성물 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR960016900A (ko) * | 1994-11-23 | 1996-06-17 | 초임계 유체 추출방법을 이용한 식물로부터 유효성분의 추출방법 |
-
2012
- 2012-04-06 KR KR1020120036330A patent/KR101433771B1/ko not_active Expired - Fee Related
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2013
- 2013-04-08 WO PCT/KR2013/002932 patent/WO2013151407A1/fr not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR960016900B1 (ko) * | 1994-01-03 | 1996-12-26 | 삼성전자 주식회사 | 하드디스크드라이브의 액츄에이터 고정장치 |
| KR20050068283A (ko) * | 2003-12-30 | 2005-07-05 | 코스맥스 주식회사 | 석창포 추출물을 포함하는 피부노화방지 조성물 |
| KR20100038029A (ko) * | 2008-10-02 | 2010-04-12 | 인성실업(주) | 초임계 추출에 의하여 크릴 오일을 생산하는 방법 및 오메가-3 지방산 함량이 높은 크일 오일 조성물 |
Non-Patent Citations (1)
| Title |
|---|
| MARONGIU, BRUNO ET AL.: "Chemical composition of the essential oil and supercritical C02 extract of Commiphora myrrha (Nees) Engl. and of Acorus calamus L..", JOURNAL OF AGRICUTURAL AND FOOD CHEMISTRY., vol. 53, 2005 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018077013A1 (fr) * | 2016-10-27 | 2018-05-03 | 陕西师范大学 | Procédé d'extraction d'huile supercritique à haut rendement |
| US10829715B2 (en) | 2016-10-27 | 2020-11-10 | Shaanxi Normal University | High-efficiency supercritical oil extraction method |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20130113820A (ko) | 2013-10-16 |
| KR101433771B1 (ko) | 2014-08-27 |
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