DE10103454A1 - Flavonoid concentrate useful in foods, body care products and cosmetics comprises a polysorbate and isoflavones and/or quercetin - Google Patents
Flavonoid concentrate useful in foods, body care products and cosmetics comprises a polysorbate and isoflavones and/or quercetinInfo
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- DE10103454A1 DE10103454A1 DE10103454A DE10103454A DE10103454A1 DE 10103454 A1 DE10103454 A1 DE 10103454A1 DE 10103454 A DE10103454 A DE 10103454A DE 10103454 A DE10103454 A DE 10103454A DE 10103454 A1 DE10103454 A1 DE 10103454A1
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- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
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- 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
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- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
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- 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
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- A61K8/60—Sugars; Derivatives thereof
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- A—HUMAN NECESSITIES
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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Abstract
Description
Die Erfindung betrifft Wirkstoffkonzentrate sowie Verfahren zu ihrer Herstellung.The invention relates to active ingredient concentrates and processes for their preparation.
Hormone sind chemische Verbindungen, die in speziellen Organen oder Zellen synthetisiert und danach an einen anderen Ort transportiert werden, um dort in sehr niedriger Konzentration Wachstum, Entwicklung und physiologisch-metabolische Leistungen zu koordinieren.Hormones are chemical compounds found in special organs or cells synthesized and then transported to another place to be there in very low concentration growth, development and physiological-metabolic Coordinate services.
Pflanzen enthalten Verbindungen, die für diese keinen Hormoncharakter haben, im Säuger jedoch hormonähnliche Wirkungen hervorrufen. Am bekanntesten sind die sogenannten Isoflavone aus Leguminosen. Soja enthält z. B. Genistein, Isogenistein und das Formononetin. Diese Stoffe haben Oestrogeneffekte und damit einen positiven Einfluß auf postmenopausale Symptome wie Kreislauf-Probleme, Typ II Diabetes und Osteoporose, erfreulicherweise ohne Nebeneffekte. Damit beeinflussen sie indirekt die Mortalitätsrate. Auch generelle Alterungsphänomene, zum Beispiel der Haut, gehören in diesen Formenkreis protektiver Eigenschaften. In Asien liegt die durchschnittliche Isoflavonaufnahme seit Jahrzehnten zwischen 20 und 100 mg/Tag, in westlichen Ländern liegt sie weit darunter.Plants contain compounds that are not hormonal in nature However, mammals produce hormone-like effects. The best known are so-called isoflavones from legumes. Soy contains e.g. B. genistein, isogenistein and the formononetin. These substances have estrogen effects and therefore one positive influence on postmenopausal symptoms such as circulatory problems, type II Diabetes and osteoporosis, fortunately without any side effects. In order to they indirectly affect the mortality rate. Also general aging phenomena, The skin, for example, belongs to this group of protective properties. In Asia, the average isoflavone intake has been between decades 20 and 100 mg / day, in western countries it is far lower.
Isoflavone vom Genistein-Typ sind in Soja und vielen anderen Pflanzen enthalten. Auf Soja basierende Ernährung, die hauptsächlich im asiatischen Raum gebräuchlich ist, führt man zurück, dass dort viel weniger Karzinome (Brust, Prostata, Haut) und bei Frauen postmenopausale Beschwerden kaum auftreten. Isoflavone sind sogenannte Phytooestrogene und binden an den Oestradiolrezeptor. Anhand von Tierversuchen und Hautmodellen konnte man erfahren, dass diese Isoflavone das intrazelluläre, enzymatische, antioxydative Potential erhöhen. Darauf führt man zum Teil ihre Wirkung zurück. Genistein type isoflavones are found in soy and many other plants. Soy-based diet, mainly in the Asian region is common, it is attributed that there are far fewer carcinomas (breast, Prostate, skin) and postmenopausal complaints in women hardly occur. Isoflavones are so-called phytoestrogens and bind to the oestradiol receptor. Animal experiments and skin models showed that these Isoflavones increase the intracellular, enzymatic, antioxidative potential. This is partly attributed to their effect.
Es ist seit längerem bekannt, dass das in Wasser nur schlecht lösliche Quercetin ein effektiver Radikalenfänger ist. 1984 konnten Elstner et al zeigen, dass Quercetin ähnlich wie zum Beispiel α-Tocopherol bestimmte Zellschutzfunktionen übernehmen kann.It has long been known that quercetin, which is poorly soluble in water, is a effective radical scavenger. In 1984 Elstner et al were able to show that quercetin Similar to α-tocopherol, for example, certain cell protection functions can take over.
Der Erfindung liegt daher die Aufgabe zugrunde, die Bioverfügbarkeit der erwähnten Wirkstoffe zu erhöhen.The invention is therefore based on the object, the bioavailability of the increase active ingredients mentioned.
Die Erfindung sieht dazu ein Wirkstoffkonzentrat vor, welches ein Polysorbat sowie einen oder mehrere der Wirkstoffe Genistein, Daidcein, Glycitein und/oder deren Glykoside, Quercetin oder dessen Derivate enthält. Das erfindungsgemäße Konzentrat ist in Wasser als klare Lösung löslich. Bei Verabreichung dieser Lösung werden die Isoflavone vom Genisteintyp im Gastrointestinal-Trakt leicht resorbiert. Es ist daher z. B. möglich, einem akoholfreien Getränk eine Gabe des erfindungsgemäßen Konzentrats mit der Folge beizugeben, dass die generelle Isoflavonaufnahme des Organismus quasi nebenbei und gleichzeitig mit dem Konsum von Getränken erhöht wird. Dabei können Isoflavone vom Genisteintyp in Form eines wasserlöslichen Konzentrats im klassischen Lebensmittelbereich und vorteilhaft im kosmetischen oder Körperpflege-Bereich eingesetzt werden. Denn die Wasserlöslichkeit sorgt für eine wesentlich erhöhte Aufnahme der Isoflavone durch die Haut.To this end, the invention provides an active ingredient concentrate which is a polysorbate and one or more of the active ingredients genistein, daidcein, glycitein and / or contains their glycosides, quercetin or its derivatives. The invention Concentrate is soluble in water as a clear solution. When administering this Solution, the genistein-type isoflavones in the gastrointestinal tract become easy absorbed. It is therefore z. B. possible, a gift of a soft drink add concentrate according to the invention with the result that the general Isoflavone uptake of the organism almost incidentally and simultaneously with the Drink consumption is increased. Isoflavones of the genistein type in Form of a water-soluble concentrate in the classic food sector and can be used advantageously in the cosmetic or personal care sector. Because the water solubility ensures a significantly increased absorption of the isoflavones through the skin.
Es empfiehlt sich, das Gewichtsverhältnis des oder der Wirkstoffe zu dem Polysorbat auf etwa 1 : 5 einzustellen. Bei größerem Gewichtsverhältnis ergibt sich eine Trübung bezw. ein Sediment in einer wässrigen Lösung des Konzentrats. Bei kleinerem Gewichtsverhältnis ist die wässrige Lösung zwar klar, jedoch überschreitet der Polysorbat-Gehalt der Lösung die lebensmittelrechtlich gezogene Grenze.It is recommended that the weight ratio of the active ingredient (s) to the Adjust the polysorbate to about 1: 5. With a larger weight ratio, this results a cloudiness or a sediment in an aqueous solution of the concentrate. at Smaller weight ratio, the aqueous solution is clear, however The polysorbate content of the solution exceeds that drawn under food law Border.
Bevorzugt sind Wirkstoffe rein pflanzlichen Ursprungs. Für ein Wirkstoffkonzentrat, das nur Isoflavone vom Genisteintyp enthält, empfiehlt es sich, ein im allgemeinen pulverförmig aufbereitetes Sojabohnen-Extrakt zu verwenden, das pro Kilogramm 40 g einer Mischung aus Genistin, Daidcin und Glycitin sowie ihrer Aglykone enthält. Vorteilhafterweise liegt das Mengenverhältnis von Genistin, Daidcin und Glycitin dann etwa bei 1,3 : 1,0 : 0,3.Active ingredients of purely vegetable origin are preferred. For a Active ingredient concentrate, which only contains isoflavones of the genistein type, is recommended itself, a generally powdered soybean extract use 40 g of a mixture of Genistin, Daidcin and Contains glycitin and its aglycones. This is advantageous The quantitative ratio of genistin, daidcin and glycitin then around 1.3: 1.0: 0.3.
Bevorzugt wird zur Herstellung des erfindungsgemäßen Konzentrates Polysorbat 80 verwendet. Zum Einsatz für den erfindungsgemäßen Zweck eignen sich indes auch das Polysorbat 20, das Polysorbat 40, das Polysorbat 60 und das Polysorbat 65, die als Teilester der Laurin-, Palmitin- oder Stearinsäure mit Sorbitol gewonnen werden.Polysorbate 80 is preferably used to produce the concentrate according to the invention. However, polysorbate 20 , polysorbate 40 , polysorbate 60 and polysorbate 65 , which are obtained as partial esters of lauric, palmitic or stearic acid with sorbitol, are also suitable for use for the purpose according to the invention.
Gegenstand der Erfindung sind daher neben nichtalkoholischen Getränken Liköre, diverse Nahrungsmittel auch Hautpflegemittel, Kosmetika und dergleichen Produkte, welche ein Isoflavonkonzentrat aus Polysorbat und einen oder mehrere der Wirkstoffe Genistein, Daidcein, Glycitein und/oder ihrer Glykoside und/oder Quercetin oder seine Derivate enthalten. Zweckmäßig enthält z. B. ein Getränk pro Liter etwa 0,5 g bis etwa 3 g Isoflavonkonzentrat. In Kapseln (1 ml) kann das Konzentrat als Antioxidans bzw. Nahrungsergänzungsmittel unverdünnt abgegeben werden.In addition to non-alcoholic drinks, the invention therefore also relates to liqueurs, Various foods including skin care products, cosmetics and the like Products that contain a polysorbate isoflavone concentrate and one or more of the active ingredients genistein, daidcein, glycitein and / or their glycosides and / or Contain quercetin or its derivatives. Appropriately contains z. B. one drink per Liter about 0.5 g to about 3 g isoflavone concentrate. This can be done in capsules (1 ml) Concentrate given undiluted as an antioxidant or food supplement become.
Zur Herstellung eines wasserlöslichen Konzentrats, das Isoflavone enthält, wird beispielsweise von 100 g Sojabohnen-Extraktpulver ausgegangen, das von der Firma Archer-Daniels-Midland Company, USA unter der Marke NOVASOY vertrieben wird. Dieses Sojabohnenextrakt enthält mindestens 40 Gew.-% Genistin, Daidcin und Glycitin und ihrer Aglykone im Mengenverhältnis 1,3 : 1,0 : 0,3. 100 g des genannten Extrakts enthalten also 20,0 g Genistin, 15,4 g Daidcin und 4,6 g Glycitin, also insgesamt 40,0 g Isoflavone.To prepare a water-soluble concentrate that contains isoflavones for example, from 100 g of soybean extract powder, which from the Archer-Daniels-Midland Company, USA under the NOVASOY brand is distributed. This soybean extract contains at least 40% by weight of genistin, Daidcin and glycitin and their aglycones in the ratio 1.3: 1.0: 0.3. 100 g of the said extract thus contain 20.0 g of genistin, 15.4 g of daidcin and 4.6 g Glycitin, i.e. a total of 40.0 g isoflavones.
Für ein Quercetin enthaltendes Mittel kann man von einem Quercetin-Dihydrat ausgehen, das von der Firma SIGMA-ALDRICH-CHEMIE GmbH, Schnelldorf, Deutschland unter der Artikelnummer 83370-100 G vertrieben wird. For an agent containing quercetin one can get a quercetin dihydrate proceed from the company SIGMA-ALDRICH-CHEMIE GmbH, Schnelldorf, Germany is sold under item number 83370-100 G.
Zur Herstellung eines wasserfreien Wirkstoffkonzentrats, welches Isoflavone vom Genistintyp enthält, dient beispielsweise das unter der Bezeichnung NOVASOY von der Firma Archer-Daniels-Midland Company, Decatur, Illinois, USA, zu beziehende pulverförmige Sojaextrakt, dessen typische Analyse sowie Chromatogramm als Anlage beigeschlossen sind. Man erkennt, dass dieses Extrakt hauptsächlich die Glykoside von Genistein, Daidcein und Glycitein enthält.For the production of an anhydrous active ingredient concentrate, which isoflavones from Genistin type contains, for example, that serves under the name NOVASOY from the Archer-Daniels-Midland Company, Decatur, Illinois, USA related powdery soy extract, its typical analysis as well Chromatogram are included as an attachment. You can see that this extract mainly contains the glycosides of genistein, daidcein and glycitein.
Ca. 166 g dieses Sojaextraktpulvers werden in ca. 834 g auf ca. 75°Celsius erwärmtes Polysorbat 80 eingerieselt und die Mischung (1,0 kg) etwa eine halbe Stunde bei dieser Temperatur gleichmäßig gerührt. Es ergibt sich ein tiefbraunes, klares Konzentrat ohne Sediment. Gibt man etwa 1-2 ml dieses Konzentrats zu der zehnfachen Menge an destilliertem Wasser von Zimmertemperatur, erhält man eine klare Lösung.Approximately 166 g of this soy extract powder are sprinkled in about 834 g of polysorbate 80 heated to about 75 ° C. and the mixture (1.0 kg) is stirred uniformly at this temperature for about half an hour. The result is a deep brown, clear concentrate without sediment. If you add about 1-2 ml of this concentrate to ten times the amount of distilled water at room temperature, a clear solution is obtained.
1,0 kg dieses Konzentrats enthält ca. 66 mg Isoflavone. Durch Zugabe von 1,5 g des Konzentrats zu 1,0 l Fertiggetränk enthält dieses etwa 100 mg der genannten Isoflavone, so dass ein Liter des derart aufbereiteten Fertiggetränks den Tagesbedarf an Isoflavonen reichlich deckt.1.0 kg of this concentrate contains approx. 66 mg isoflavones. By adding 1.5 g of the concentrate to 1.0 l ready drink contains about 100 mg of the above Isoflavones, so that one liter of the finished drink prepared in this way Daily requirements for isoflavones are sufficient.
Anstelle von NOVASOY kann man auch von Sojaextrakten anderer Provenienz ausgehen, die sich durch eine größere Zuckerfreiheit auszeichnen. Beispielsweise ist von der Firma K.-W. Pfannenschmidt GmbH, Hamburg, ein Sojabohnenextrakt erhältlich, das einen gesamten Isoflavongehalt von wenigstens von 40% aufweist. Diese etwa 40% setzen sich zusammen aus 7,58% Genistin, 25,43% Genistein, 5,48% Daidcin und 1,67% Daidcein. Verfährt man mit diesem Sojabohnenextrakt wie vorstehend im Zusammenhang mit NOVASOY beschrieben, erhält man in etwa die gleichen Ergebnisse.Instead of NOVASOY you can also use soy extracts from other sources go out, which are characterized by a greater sugar-free. For example is from the company K.-W. Pfannenschmidt GmbH, Hamburg, a soybean extract available that has a total isoflavone content of at least 40%. These about 40% are composed of 7.58% genist, 25.43% genistein, 5.48% daidcin and 1.67% daidcein. Do this with this soybean extract as described above in connection with NOVASOY, is obtained in about the same results.
Vorstehend ist die Herstellung eines wasserfreien Wirkstoffkonzentrats beschrieben. Es ist jedoch auch möglich, ein wässriges Wirkstoffkonzentrat nach den folgenden Beispielen zu erhalten: Above is the preparation of an anhydrous active ingredient concentrate described. However, it is also possible to add an aqueous active ingredient concentrate to get the following examples:
Die Gewinnung des erfindungsgemäßen wasserlöslichen Isoflavonkonzentrats sieht vor, dass man die genannten Zusammensetzungen in auf etwa 60°C erwärmtes Wasser einrieselt und die Mischung während einer vorgegebenen Zeitspanne von etwa zehn Minuten bei der genannten Temperatur rührt. Alsdann wird das Polysorbat der Mischung zugegeben und die Temperatur dabei auf etwa 100°C erhöht. Bei dieser Temperatur wird der Rührvorgang solange fortgesetzt, bis die Mischung klar und transparent geworden ist. Alternativ kann den Zusammensetzungen zuerst Polysorbat zugegeben und anschließend Wasser zugesetzt werden.The recovery of the water-soluble isoflavone concentrate according to the invention provides before that the said compositions in heated to about 60 ° C. Water trickles and the mixture for a predetermined period of stirred for about ten minutes at the temperature mentioned. Then it will Polysorbate added to the mixture and the temperature at about 100 ° C. elevated. At this temperature, the stirring process is continued until the Mixture has become clear and transparent. Alternatively, the Compositions first added polysorbate and then water be added.
Beispielsweise werden 100 g des erwähnten Sojabohnenextraktes NOVASOY gleichmäßig in 400 g destilliertes Wasser eingerührt, das zuvor auf ca 60°C erwärmt wurde. Die Mischung (Gesamtmenge 500 g) wird unter Beibehaltung der Temperatur von etwa 60°C ca. zehn Minuten konstant mittels eines Magnetrührers gerührt. Unter Fortsetzung des Rührvorganges werden 500 g Polysorbat 80 hinzugegeben und die Temperatur dabei auf ca. 100°C erhöht.For example, 100 g of the soybean extract NOVASOY mentioned are evenly stirred into 400 g of distilled water, which has previously been heated to about 60 ° C. The mixture (total amount 500 g) is constantly stirred for about ten minutes using a magnetic stirrer while maintaining the temperature of about 60 ° C. While continuing the stirring process, 500 g of polysorbate 80 are added and the temperature is increased to about 100 ° C.
Bei dieser Temperatur wird der Rührvorgang solange fortgesetzt, bis die Mischung (Gesamtmenge 1 kg) klar und transparent geworden ist. Diese klare Mischung enthält die eingearbeiteten 40 g Isoflavone.The stirring process is continued at this temperature until the mixture (Total amount 1 kg) has become clear and transparent. This clear mix contains the incorporated 40 g isoflavones.
2,5 g dieses klaren, stabilen wässrigen Konzentrats enthalten 100 mg Isoflavone. Diese Menge kann beispielsweise in einen Liter Fertiggetränk eingearbeitet werden, das somit den doppelten Tagesbedarf in Höhe von 50 mg Isoflavone deckt.2.5 g of this clear, stable aqueous concentrate contain 100 mg of isoflavones. This amount can, for example, be incorporated into a liter of finished beverage that covers twice the daily requirement of 50 mg isoflavones.
Zur Gewinnung eines wässrigen Konzentrats, das von den genannten Wirkstoffen nur Quercetin bezw. sein Derivat enthält, kann wie folgt vorgegangen werden: 67 g Quercetin-Dihydrat werden gleichmäßig in 280 g destilliertes Wasser eingerührt, das zuvor auf ca 60°C erwärmt wurde. Die Mischung (Gesamtmenge 347 g) wird unter Beibehaltung der Temperatur von 60°C ca fünf Minuten konstant durch einen Magnetrührer gerührt. Unter Fortsetzung des Rührvorganges werden 653 g Polysorbat 80 hinzugegeben und die Temperatur dabei auf ca 100°C erhöht. To obtain an aqueous concentrate that only quercetin or of the active ingredients mentioned. contains its derivative, can be carried out as follows: 67 g quercetin dihydrate are evenly stirred into 280 g distilled water, which was previously heated to about 60 ° C. The mixture (total amount 347 g) is constantly stirred for about five minutes using a magnetic stirrer while maintaining the temperature at 60 ° C. While continuing the stirring process, 653 g of polysorbate 80 are added and the temperature is increased to about 100 ° C.
Bei dieser Temperatur wird der Rührvorgang solange fortgesetzt, bis die Mischung (Gesamtmenge 1 kg) klar und transparent geworden ist. Diese klare Mischung enthält die eingearbeiteten 67 g Quercetin.The stirring process is continued at this temperature until the mixture (Total amount 1 kg) has become clear and transparent. This clear mix contains the incorporated 67 g quercetin.
1 g dieses klaren stabilen, wässrigen Konzentrats enthält 67 mg Quercetin. Diese Menge kann beispielsweise in einen Liter Fertiggetränk eingearbeitet werden.1 g of this clear, stable, aqueous concentrate contains 67 mg quercetin. This For example, the quantity can be incorporated into a liter of finished beverage.
Die Stabilität des erfindungsgemäßen Konzentrates in seiner Klarheit und Wasserlöslichkeit ist auch dann gegeben, wenn dem erfindungsgemäßen Konzentrat oder einem daraus hergestellten Mittel (z. B. Getränk) Magensäure zugegeben wird. Dies gilt auch dann, wenn das Konzentrat z. B. auf etwa 100°C erhitzt wird. Das Konzentrat zeichnet sich also durch eine ausgezeichnete Stabilität aus.The stability of the concentrate according to the invention in its clarity and Water solubility is also given when the invention Concentrate or an agent made from it (e.g. beverage) gastric acid is added. This also applies if the concentrate z. B. to about 100 ° C. is heated. The concentrate is therefore characterized by excellent stability out.
Claims (17)
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DE10103454A DE10103454A1 (en) | 2000-12-29 | 2001-01-25 | Flavonoid concentrate useful in foods, body care products and cosmetics comprises a polysorbate and isoflavones and/or quercetin |
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WO2006010370A1 (en) * | 2004-07-22 | 2006-02-02 | Aquanova German Solubilisate Technologies (Agt) Gmbh | Essential oil and other substance solubilised products |
DE102005032352A1 (en) * | 2005-07-08 | 2007-01-11 | Aquanova German Solubilisate Technologies (Agt) Gmbh | Solubilizer for an active ingredient concentrate in the food industry comprises a St. John's wort extract, a roseda extract or a tarragon extract, a polysorbate emulsifier and water |
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WO2002085328A3 (en) * | 2001-02-11 | 2003-11-06 | Aquanova Ger Solubilisate Tech | Method for producing an active ingredient concentrate, and an active ingredient concentrate |
WO2002085328A2 (en) * | 2001-02-11 | 2002-10-31 | Aquanova German Solubilisate Technologies (Agt) Gmbh | Method for producing an active ingredient concentrate, and an active ingredient concentrate |
US7208594B2 (en) | 2002-06-29 | 2007-04-24 | Aquanova Ag | Isoflavone concentrates as well as methods for their production |
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DE102005032352A1 (en) * | 2005-07-08 | 2007-01-11 | Aquanova German Solubilisate Technologies (Agt) Gmbh | Solubilizer for an active ingredient concentrate in the food industry comprises a St. John's wort extract, a roseda extract or a tarragon extract, a polysorbate emulsifier and water |
WO2007006497A3 (en) * | 2005-07-08 | 2007-07-26 | Aquanova Ger Solubilisate Tech | Solubilsation products of an active ingredient extract |
WO2007006497A2 (en) * | 2005-07-08 | 2007-01-18 | Aquanova German Solubilisate Technologies (Agt) Gmbh | Solubilsation products of an active ingredient extract |
JP2016222680A (en) * | 2009-10-22 | 2016-12-28 | エイピーアイ・ジェネシス,エルエルシー | Methods of making and using compositions comprising flavonoids |
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US9889098B2 (en) | 2009-10-22 | 2018-02-13 | Vizuri Health Sciences Llc | Methods of making and using compositions comprising flavonoids |
US11135177B2 (en) | 2009-10-22 | 2021-10-05 | Vizuri Health Sciences Consumer Healthcare, Inc. | Methods of making and using compositions comprising flavonoids |
US11491226B2 (en) | 2009-10-22 | 2022-11-08 | Technology Investments Lc | Methods of increasing solubility of poorly soluble compounds and methods of making and using formulations of such compound |
JP2013541557A (en) * | 2010-10-22 | 2013-11-14 | エイピーアイ・ジェネシス,エルエルシー | Methods of increasing the solubility of poorly soluble compounds and methods of making and using such compounds |
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