WO2005075614A1 - Procede d'obtention de composes a haute valeur ajoutee a partir de feuilles d'olivier - Google Patents

Procede d'obtention de composes a haute valeur ajoutee a partir de feuilles d'olivier Download PDF

Info

Publication number
WO2005075614A1
WO2005075614A1 PCT/ES2005/070013 ES2005070013W WO2005075614A1 WO 2005075614 A1 WO2005075614 A1 WO 2005075614A1 ES 2005070013 W ES2005070013 W ES 2005070013W WO 2005075614 A1 WO2005075614 A1 WO 2005075614A1
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
olive leaf
added value
high added
leaf according
Prior art date
Application number
PCT/ES2005/070013
Other languages
English (en)
Spanish (es)
Inventor
J. Javier TABERA GALVÁN
Alejandro RUIZ RODRÍGUEZ
Francisco Javier SEÑORÁNS RODRÍGUEZ
Elena IBÁÑEZ EZEQUIEL
Guillermo J. Reglero Rada
Tomás ALBI VIRELLA
Augusto LANZÓN REY
Mª Carmen PÉREZ CAMINO
Mª Ángeles GUINDA GARÍN
Mirella Rada Rada
Original Assignee
Consejo Superior De Investigaciones Científicas
Universidad Autonoma De Madrid
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Consejo Superior De Investigaciones Científicas, Universidad Autonoma De Madrid filed Critical Consejo Superior De Investigaciones Científicas
Publication of WO2005075614A1 publication Critical patent/WO2005075614A1/fr

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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)
    • A61K36/63—Oleaceae (Olive family), e.g. jasmine, lilac or ash tree
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • B01D11/0288—Applications, solvents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
    • B01D11/0407—Solvent extraction of solutions which are liquid with a supercritical fluid the supercritical fluid acting as solvent for the solute
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0426—Counter-current multistage extraction towers in a vertical or sloping position
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the object of the present invention is a process for obtaining compounds of high added value from olive leaf by solid-liquid extraction with solvents and subsequent fractionation with CO 2 in supercritical state.
  • the sheets are subjected to solid-liquid extraction with organic solvents, preferably hexane or ethanol, and the crude extract obtained is concentrated in vacuo.
  • a fractioning of this crude extract is carried out by countercurrent extraction in a column with supercritical CO 2 and separation in two cells in which different pressure and / or temperature conditions that change the solvent power of CO 2 are set , precipitating different compounds.
  • the process of the invention allows natural products of interest to the food, pharmaceutical and cosmetic industries to be extracted from the olive leaf, such as waxes, squalene, ⁇ -carotene, ⁇ -tocopherol, oleuropein, hydroxytyrosol and other phenolic compounds, ⁇ -sitosterol, ⁇ and ⁇ -amirin, erythrodiol, uvaol and other terpenic alcohols, oleanolic acid, ursolic acid and maslinic acid, among others.
  • natural products of interest to the food, pharmaceutical and cosmetic industries to be extracted from the olive leaf, such as waxes, squalene, ⁇ -carotene, ⁇ -tocopherol, oleuropein, hydroxytyrosol and other phenolic compounds, ⁇ -sitosterol, ⁇ and ⁇ -amirin, erythrodiol, uvaol and other terpenic alcohols, oleano
  • the present invention is related to obtaining natural compounds of high added value from olive leaf, by-product of the olive grove that enters the oil mills in considerable quantities (about 10% on the weight of the olive) and of which currently poor profitability is obtained.
  • the compounds obtained are, among others: waxes, squalene, ⁇ -carotene, ⁇ -tocopherol, oleuropein, hydroxytyrosol and other phenolic compounds, ⁇ -sitosterol, ⁇ and ⁇ -amirin, erythrodiol, uvaol and other terpenic alcohols, oleanolic acid, acid Ursolic and maslinic acid.
  • Some of them (squalene, ⁇ -carotene, ⁇ -tocopherol, hydroxytyrosol and other phenolic compounds) have antioxidant activity, so they find application both in prolonging the shelf life of food and in reducing oxidative stress in the human organism .
  • they can be used as functional food ingredients or drugs. They are also used in pharmacy, parapharmacy and cosmetics in topical preparations protective and regenerating the skin.
  • Ursolic acid is also used in cosmetic preparations against skin wrinkles.
  • maslinic acid is studied as an inhibitor of proteases responsible for the infective power of HIV (ES2140329) and intestinal parasites of the genus Cryptosporidium (ES2131467). Infection with these protozoa is high risk in immunosuppressed patients and for her there is no specific therapy.
  • the sheet is usually dried and / or ground (US2003152656, US2002054927, FR2810887, EP1157701), extracted with an organic solvent (US2003185921, US2003152656, FR2810887, EP1157701), with water (US2002054927, ES2056745), or with ethanol-water mixture (US5714150);
  • the Soxhlet extractor (DE10213032, DE10213019, DE10213031, EP1213025) is used.
  • the extract obtained is usually concentrated or dried by evaporation or lyophilization (US2003152656, US2002054927, FR2810887, EP1157701, US5714150, ES2056745).
  • the extract obtained by any of the above or similar procedures can be concentrated and fractionated by extraction with CO 2 in supercritical state (P> 7.3 MPa and T> 31.1 ° C), in which it has solvation properties similar to those of liquids and viscosities and diffusivities similar to those of gases, making it an ideal extractant.
  • the extraction capacity of supercritical carbon dioxide can be made selective towards a certain group of compounds by modifying their density, which can be achieved in the same installation with slight adjustments of pressure and temperature.
  • supercritical CO 2 is not toxic, it is released from products extracted by simple passage to the gaseous state, and produces effective extractions at mild temperatures and, obviously, in a non-oxidizing atmosphere.
  • the present invention involves a process for the extraction and fractionation of high added value compounds present in the olive leaf, applicable in the food, pharmaceutical and cosmetic industries.
  • the process comprises a solid-liquid extraction with organic solvents, preferably hexane or ethanol, from the olive leaf, an extraction with supercritical CC ⁇ of the concentrated crude extract above and a fractionation of the latter extract. Washed olive leaf is used if it comes from pruning the olive or unwashed if it comes from the separation of olives from the mill.
  • the olive leaf is dried by forced air at a temperature between 30 and 40 ° C for at least 24 hours and chopped in a knife chopper.
  • the olive leaf is extracted whole and without drying.
  • the leaves are extracted by prolonged contact (maceration) with the organic solvent, hexane or ethanol, in a leaf / solvent ratio between 1/4 - 1/20 weight / volume and at a temperature between 20 ° C and 40 ° C. If the solvent is hexane, the maceration takes place during a period between 30 and 60 hours. If the solvent is ethanol, the maceration takes place during a period between 100 and 160 hours.
  • the clarification is carried out, by filtration or centrifugation, of the extract and then at the concentration of the clarified by evaporation under vacuum of the solvent (T ⁇ 40 ° C), until a volume of crude extract between 20% and 50% of the initial maceration volume.
  • the crude extract thus obtained is extracted in countercurrent with supercritical CO2 in a filled column in a temperature range between 35 and 50 ° C and in a pressure range between 15 and 35 Mpa obtaining a supercritical extract in which there is lower concentration of organic solvent than in the crude extract.
  • the effluent of this column, supercritical extract is taken to a first separation cell where, by lowering the pressure to values below 20 MPa, preferably between 10 and 15 Mpa, and / or changing the temperature, the solvent power of CO 2 , precipitating the non-soluble compounds in these new conditions.
  • the effluent from this first cell is taken to a second separation cell, where the pressure is again reduced to values lower than 2 MPa, preferably between 1 and 2 MPa, bringing the carbon dioxide to the gaseous state and producing precipitation of all the compounds that were dissolved in it.
  • the two fractions, of different composition, obtained in the two cells are collected.
  • a third fraction (refined), consisting mainly of the organic solvent and compounds not soluble in supercritical CO 2 , is collected from the extraction column. DETAILED DESCRIPTION OF THE INVENTION
  • the process object of the present invention consists in the extraction of the olive leaf with organic solvents, preferably hexane or ethanol.
  • organic solvents preferably hexane or ethanol.
  • the leaves, obtained from the pruning of the olive tree or separated from the olives in the oil mills, are washed or not, depending on their origin, they are dried with forced air at 30-40 ° C and chopped with a knife chopper if they are to be extracted with solvents such as hexane or extracted whole and without drying with solvents such as ethanol.
  • the extraction is carried out by prolonged contact (maceration) for a time between 30 and 60 hours if hexane is used or between 100 and 160 hours if ethanol is used, in a leaf / solvent ratio between 1 / 4-1 / 20 ( weight / volume) and at a temperature between 20 and 40 ° C.
  • the extract is then concentrated under vacuum (10-20 mm pressure), keeping the temperature below 40 ° C, until a volume between 20 and 20 is achieved. % and 50% of the initial. Finally it is clarified by filtration with filter plate or centrifugation.
  • the crude extract obtained as described above is fed to a column filled with extraction, capable of withstanding pressures greater than 40 MPa, traveled in the opposite direction by carbon dioxide in a supercritical state, preferably at a pressure between 15 and 35 MPa and temperature between 35 and 50 ° C, in an amount (measured in atmospheric conditions) between 5 and 40 times the raw extract feed flow rate, preferably 12 times.
  • a column filled with extraction capable of withstanding pressures greater than 40 MPa, traveled in the opposite direction by carbon dioxide in a supercritical state, preferably at a pressure between 15 and 35 MPa and temperature between 35 and 50 ° C, in an amount (measured in atmospheric conditions) between 5 and 40 times the raw extract feed flow rate, preferably 12 times.
  • a suitable modifier is ethanol that would be added in a proportion of up to 10% over the flow of CO 2
  • the appropriate modifier is water that is added also in proportion of up to 10% over the flow of CO 2 .
  • the supercritical CO 2 containing the soluble compounds under the conditions of the extraction column passes to a first separating cell in which, by means of reductions in pressure and / or variations in temperature, the solvent power of CO 2 is reduced, so that they precipitate preferably a first group of compounds, insoluble in the new conditions.
  • the color of this first fraction is usually yellowish-green.
  • the pressure of carbon dioxide is between 10 and 15 MPa.
  • the carbon dioxide containing the compounds still soluble under the pressure and temperature conditions of the first separating cell, is taken to a second cell in which, by means of a new pressure decrease, it enters the gaseous state, all precipitating the compounds it brought dissolved.
  • the pressure of carbon dioxide is between 1 and 2 MPa.
  • This second fraction is usually colorless or pale yellow.
  • the third fraction consists of refining, the crude extract already extracted with supercritical CO 2 that remains in the extraction column. It is collected by gravity, by its base, once the system is depressurized. It is enriched in compounds less soluble in carbon dioxide at the density of the latter in the extraction column and usually has a brown-greenish color, darker than the crude extract.
  • the crude hexane extract thus obtained containing 962.4 ⁇ g / g of ⁇ -tocopherol, 123.5 ⁇ g / g of ⁇ -sitosterol and 429.0 ⁇ g / g of terpenic alcohols, is fed at a rate of 200 mL / ha the column (stainless steel AISI 316, cylindrical, 17.6 mm internal diameter and 180 cm high), filled with Fenske rings, and extracted in countercurrent with 2500 mL / h of CO 2 at 20 MPa and 35 ° C for 35 minutes, with the addition of ethanol as a modifier (10% over the flow rate of CO 2 ).
  • the extract obtained is partially separated in the first separating cell (stainless steel AISI 316, cylindrical, 270 mL capacity) reducing the pressure to 12 MPa, obtaining in it a greenish yellow product containing 105.6 ⁇ g / g of ⁇ - tocopherol, 57.6 ⁇ g / g of ⁇ -sitosterol and 103.3 ⁇ g / g of terpenic alcohols.
  • the first separating cell stainless steel AISI 316, cylindrical, 270 mL capacity
  • the effluent of this first is taken to the second separating cell (stainless steel AISI 316, cylindrical, 270 mL capacity) where, by lowering the pressure up to 1 MPa, the compounds dissolved in the carbon dioxide are recovered, now in a gaseous state, obtaining a pale yellow product containing 80.4 ⁇ g / g of ⁇ - tocopherol, 474.7 ⁇ g / g of ⁇ -sitosterol and 1661.6 ⁇ g / g of triterpenic dialcohols. Both ⁇ -sitosterol and terpenic alcohols are concentrated in the second separator cell, while ⁇ -tocopherol is, for the most part, refined.
  • the second separating cell stainless steel AISI 316, cylindrical, 270 mL capacity
  • the solution is concentrated in vacuo to 20% of the original volume, at a temperature below 40 ° C, producing a precipitate (mostly oleanolic acid) that is separated by centrifugation or filtration
  • the crude extract in ethanol thus obtained, containing among other compounds 78.6 ⁇ g / g of hydroxytyrosol, 140.2 ⁇ g / g of erythrodiol and 70.0 ⁇ g / g uvaol are fed at a rate of 150 mL / ha column (stainless steel AISI 316, cylindrical, 17.6 mm internal diameter and 180 cm high), filled with Fenske rings, and extracted in countercurrent with 2500 mL / h of CO 2 at 25 MPa and 35 ° C for 120 minutes, with the addition of water as a modifier (5% on CO 2 flow).
  • the extract obtained is partially separated in the first separating cell (stainless steel AISI 316, cylindrical, 270 mL capacity) reducing the pressure to 10 MPa, obtaining a yellowish product containing 34.8 ⁇ g / g of hydroxytyrosol, 320 , 2 ⁇ g / g of erythrodiol and 240.0 ⁇ g / g uvaol.
  • the first separating cell stainless steel AISI 316, cylindrical, 270 mL capacity
  • the effluent of this first is taken to the second separating cell (stainless steel AISI 316, cylindrical, 270 mL capacity) where, by lowering the pressure up to 2 MPa, the compounds dissolved in the carbon dioxide are recovered, now in a gaseous state, obtaining a pale yellow product containing 29.0 ⁇ g / g of hydroxytyrosol, 70.2 ⁇ g / g of erythrodiol and 50.6 ⁇ g / g uvaol. Both erythrodiol and uvaol are concentrated in the first separating cell, while hydroxytyrosol is, for the most part, refined (284.2 ⁇ g / g).

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Food Science & Technology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Medical Informatics (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Cosmetics (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé d'obtention de composés à haute valeur ajoutée à partir de feuilles d'olivier. Ce procédé comprend les étapes suivantes : une première étape dans laquelle les feuilles d'olivier sont soumises à une extraction solide-liquide au moyen de dissolvants organiques, de préférence hexane ou éthanol, et dans laquelle l'extrait brut obtenu est concentré à vide ; et une deuxième étape dans laquelle l'extrait brut est fractionné par extraction à contre-courant dans une colonne avec du CO2 supercritique, et séparé dans deux cellules dans lesquelles sont fixées différentes conditions de pression et/ou de température qui changent le pouvoir dissolvant du CO2, ce qui permet de précipiter différents composés. Ledit procédé permet d'extraire des feuilles d'olivier des produits naturels d'intérêt pour les industries alimentaire, pharmaceutique et cosmétique, de type cires, squalène, β-carotène, α-tocoférol, oleuropéine, hydroxityrosol et autres composés phénoliques, β-sitostérol, α et β-amyrine, érythrodiol, uvaol et autres alcools terpéniques, acide oléanolique, acide ursolique et acide maslinique, entre autres.
PCT/ES2005/070013 2004-02-09 2005-02-08 Procede d'obtention de composes a haute valeur ajoutee a partir de feuilles d'olivier WO2005075614A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES200400293A ES2238183B1 (es) 2004-02-09 2004-02-09 Procedimiento para obtener compuestos de alto valor añadido a partir de hoja de olivo.
ESP200400293 2004-02-09

Publications (1)

Publication Number Publication Date
WO2005075614A1 true WO2005075614A1 (fr) 2005-08-18

Family

ID=34833894

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/ES2005/070013 WO2005075614A1 (fr) 2004-02-09 2005-02-08 Procede d'obtention de composes a haute valeur ajoutee a partir de feuilles d'olivier

Country Status (2)

Country Link
ES (1) ES2238183B1 (fr)
WO (1) WO2005075614A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1818388A1 (fr) * 2006-02-10 2007-08-15 Carotech SDN. BHD Procédé d'obtention de fractions enrichies contenant de composés naturels à partir d'huile de Palme par fluides supercritiques ou presque supercritiques
WO2007091901A1 (fr) * 2006-02-07 2007-08-16 Industrial Research Limited Procédé d'extraction de fluides sous-critiques
EP2338500A1 (fr) 2009-12-23 2011-06-29 Phenofarm S.r.l. Procédé de production d'actifs concentrés et raffinés à partir de tissus et sous-produits d'Olea europaea avec des technologies de membrane
CN102504823A (zh) * 2011-11-08 2012-06-20 江南大学 一种橄榄酚类天然抗氧化剂的制备方法
CN102701914A (zh) * 2012-06-21 2012-10-03 桂林三宝药业有限公司 从橄榄叶中提取羟基酪醇的方法
FR2989373A1 (fr) * 2012-04-16 2013-10-18 Roquette Freres Procede de raffinage du squalene produit par microalgues
WO2013160881A1 (fr) 2012-04-26 2013-10-31 Universidade De Aveiro Procédé d'obtention d'un extrait riche en acides triterpéniques à partir d'écorces d'eucalyptus
WO2013156720A3 (fr) * 2012-04-16 2014-01-09 Roquette Freres Procédé de raffinage du squalène produit par microalgues
US9029615B2 (en) 2012-09-05 2015-05-12 Dynasep Inc. Energy efficient method and apparatus for the extraction of lower alcohols from dilute aqueous solution
WO2017032722A1 (fr) * 2015-08-21 2017-03-02 N-Zyme Biotec Gmbh Extrait de feuilles d'olivier
US9630894B2 (en) 2012-09-05 2017-04-25 Dynasep Inc. Energy efficient method and apparatus for the extraction of biomolecules from dilute aqueous solution
US11547843B2 (en) 2007-07-19 2023-01-10 Innovative Medical Devices, Llc Venous access port assembly with x-ray discernable indicia

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2969656B1 (fr) * 2010-12-23 2013-01-04 Charabot Procede pour l'obtention d'un extrait odorant de fleurs et/ou feuilles fraiches par des solvants naturels

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5714150A (en) * 1997-01-08 1998-02-03 Nachman; Leslie Method for producing extract of olive leaves
EP1157701A1 (fr) * 1999-12-23 2001-11-28 ASAC Compania de Biotecnologia E Investigacion, S.A. Procede permettant d'obtenir des extraits de olea europeae et applications de ceux-ci
US20030152656A1 (en) * 2002-02-13 2003-08-14 Pinnell Sheldon R. Olive leaf extraction method and formulations containing olive leaf extract

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6784439B2 (en) * 2001-07-19 2004-08-31 Ut Battelle, Llc Thin-channel electrospray emitter

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5714150A (en) * 1997-01-08 1998-02-03 Nachman; Leslie Method for producing extract of olive leaves
EP1157701A1 (fr) * 1999-12-23 2001-11-28 ASAC Compania de Biotecnologia E Investigacion, S.A. Procede permettant d'obtenir des extraits de olea europeae et applications de ceux-ci
US20030152656A1 (en) * 2002-02-13 2003-08-14 Pinnell Sheldon R. Olive leaf extraction method and formulations containing olive leaf extract

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LE FLOCH F. ET AL: "Supercritical fluid extraction of phenol compounds from olive leaves.", TALANTA., vol. 46, no. 5, 1998, pages 1123 - 1130 *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8580116B2 (en) 2006-02-07 2013-11-12 Industrial Research Limited Near-critical fluid extraction process
WO2007091901A1 (fr) * 2006-02-07 2007-08-16 Industrial Research Limited Procédé d'extraction de fluides sous-critiques
AU2007212831B2 (en) * 2006-02-07 2012-09-13 Industrial Research Limited Near-critical fluid fractionation process
AU2007212831C1 (en) * 2006-02-07 2013-03-07 Industrial Research Limited Near-critical fluid fractionation process
WO2007090545A1 (fr) * 2006-02-10 2007-08-16 Carotech Sdn.Bhd. Méthode pour produire des fractions fortement enrichies de composés naturels à partir d'huile de palme avec des fluides supercritiques et des fluides proches du point critique
US8048462B2 (en) 2006-02-10 2011-11-01 Carotech SD. BHD Process for production of highly enriched fractions of natural compounds from palm oil with supercritical and near critical fluids
EP1818388A1 (fr) * 2006-02-10 2007-08-15 Carotech SDN. BHD Procédé d'obtention de fractions enrichies contenant de composés naturels à partir d'huile de Palme par fluides supercritiques ou presque supercritiques
US11547843B2 (en) 2007-07-19 2023-01-10 Innovative Medical Devices, Llc Venous access port assembly with x-ray discernable indicia
EP2338500A1 (fr) 2009-12-23 2011-06-29 Phenofarm S.r.l. Procédé de production d'actifs concentrés et raffinés à partir de tissus et sous-produits d'Olea europaea avec des technologies de membrane
CN102504823A (zh) * 2011-11-08 2012-06-20 江南大学 一种橄榄酚类天然抗氧化剂的制备方法
CN105296552A (zh) * 2012-04-16 2016-02-03 罗盖特兄弟公司 用于精炼微藻产生的角鲨烯的方法
WO2013156720A3 (fr) * 2012-04-16 2014-01-09 Roquette Freres Procédé de raffinage du squalène produit par microalgues
CN104245076A (zh) * 2012-04-16 2014-12-24 罗盖特兄弟公司 用于精炼微藻产生的角鲨烯的方法
FR2989373A1 (fr) * 2012-04-16 2013-10-18 Roquette Freres Procede de raffinage du squalene produit par microalgues
US9346722B2 (en) 2012-04-16 2016-05-24 Roquette Freres Method for refining squalene produced by microalgae
CN104245076B (zh) * 2012-04-16 2017-03-01 罗盖特兄弟公司 用于精炼微藻产生的角鲨烯的方法
WO2013160881A1 (fr) 2012-04-26 2013-10-31 Universidade De Aveiro Procédé d'obtention d'un extrait riche en acides triterpéniques à partir d'écorces d'eucalyptus
CN102701914A (zh) * 2012-06-21 2012-10-03 桂林三宝药业有限公司 从橄榄叶中提取羟基酪醇的方法
US9029615B2 (en) 2012-09-05 2015-05-12 Dynasep Inc. Energy efficient method and apparatus for the extraction of lower alcohols from dilute aqueous solution
US9630894B2 (en) 2012-09-05 2017-04-25 Dynasep Inc. Energy efficient method and apparatus for the extraction of biomolecules from dilute aqueous solution
WO2017032722A1 (fr) * 2015-08-21 2017-03-02 N-Zyme Biotec Gmbh Extrait de feuilles d'olivier

Also Published As

Publication number Publication date
ES2238183B1 (es) 2006-12-16
ES2238183A1 (es) 2005-08-16

Similar Documents

Publication Publication Date Title
WO2005075614A1 (fr) Procede d'obtention de composes a haute valeur ajoutee a partir de feuilles d'olivier
US8066881B2 (en) Method of obtaining a natural hydroxytyrosol-rich concentrate from olive tree residues and subproducts using clean technologies
US10967018B2 (en) Methods for extraction and isolation of isoprenoid and terpene compounds from biological extracts
JP4571081B2 (ja) ライチポリフェノール含有組成物、その製造方法及び用途
ES2655562T3 (es) Composiciones cosméticas que contienen fracciones de extractos de arándano rojo
JP5602346B2 (ja) ユーカリ抽出物の調製方法
JP2814094B2 (ja) アセロラエキスを含む化粧品
KR102433271B1 (ko) 티트리, 하수오 유래 세포외 소포체를 유효성분으로 함유하는 화장료 조성물
WO2012014948A1 (fr) Antioxydant et matériau cosmétique
CN110090180B (zh) 化妆品用紫草提取物及其制备方法
JPH10218786A (ja) 蕎麦殻抽出物を有効成分とする薬剤
JP5995700B2 (ja) ポリメトキシフラボン類の製造方法
JPH03227985A (ja) イチョウ葉からフラボノイドを高含有する抽出物の簡易な製造法
KR20210026726A (ko) 아임계수를 이용한 포도송이덩굴로부터 레스베라트롤 추출 및 재결정화물 분리방법
KR20200016101A (ko) 에틸 락테이트를 이용한 천연물질 추출물의 제조방법
KR20050097698A (ko) 감 껍질을 이용한 올레아놀산 및 우르솔산의 제조방법
JP7570615B2 (ja) 抗酸化剤、抗酸化剤の製造方法および酸化反応の進行を抑制する方法
JP4264456B2 (ja) ヒアルロニダーゼ活性阻害剤
JP4994684B2 (ja) 保湿剤、細胞賦活剤、及び抗酸化剤
JP4245862B2 (ja) 皮膚外用剤
JPH10121044A (ja) 抗酸化剤、活性酸素消去剤およびそれらの応用
EP4322764A1 (fr) Procédé de fractionnement
EP3924081A2 (fr) Procédé d'obtention de secoiridoïdes de type oléocanthal et de production de préparations pharmaceutiques respectives
JP2021102589A (ja) カワラケツメイ属に属する植物の発酵物ならびに前記を含有する化粧料および皮膚外用剤
JP5231777B2 (ja) アポトーシス誘導作用を呈するテルペン誘導体及びその製造方法

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

WWW Wipo information: withdrawn in national office

Country of ref document: DE

122 Ep: pct application non-entry in european phase