WO2021037656A1 - Folsäure-solubilisat - Google Patents

Folsäure-solubilisat Download PDF

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Publication number
WO2021037656A1
WO2021037656A1 PCT/EP2020/073310 EP2020073310W WO2021037656A1 WO 2021037656 A1 WO2021037656 A1 WO 2021037656A1 EP 2020073310 W EP2020073310 W EP 2020073310W WO 2021037656 A1 WO2021037656 A1 WO 2021037656A1
Authority
WO
WIPO (PCT)
Prior art keywords
solubilizate
range
polysorbate
temperature
weight
Prior art date
Application number
PCT/EP2020/073310
Other languages
German (de)
English (en)
French (fr)
Inventor
Dariush Behnam
Original Assignee
Aquanova Ag
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 Aquanova Ag filed Critical Aquanova Ag
Priority to CN202080061116.XA priority Critical patent/CN114364268A/zh
Priority to EP20761181.5A priority patent/EP4021412A1/de
Publication of WO2021037656A1 publication Critical patent/WO2021037656A1/de

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • 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
    • A23L33/15—Vitamins
    • 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
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F3/00—Biological treatment of water, waste water, or sewage
    • C02F3/34—Biological treatment of water, waste water, or sewage characterised by the microorganisms used
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/68—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2305/00—Use of specific compounds during water treatment
    • C02F2305/06—Nutrients for stimulating the growth of microorganisms
    • 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
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W10/00—Technologies for wastewater treatment
    • Y02W10/30—Wastewater or sewage treatment systems using renewable energies
    • Y02W10/37—Wastewater or sewage treatment systems using renewable energies using solar energy

Definitions

  • the invention relates to a folic acid solubilizate according to claim 1. Furthermore, the invention relates to the use of such a solubilizate as
  • Folic acid is a vitamin from the B complex and is chemically composed of a pteridine derivative, para-aminobenzoic acid and L-glutamic acid. It is also known as pteroglutamic acid. Folic acid is the precursor of the coenzyme tetrahydrofolic acid, which is present as an anion tetrahydrofolate under physiological conditions. In the human and animal organism as well as for some microorganisms, folic acid has an important role in the metabolism, especially in the provision of building blocks for DNA replication, or as a growth factor. Folic acid is unstable in contact with oxygen and / or UV radiation.
  • folic acid formulations for the nutrition of humans and animals
  • those for supporting the activity of microorganisms in biological-technical applications are known.
  • One example of this is the addition of folic acid to the water to be treated in sewage treatment plants.
  • DE 4213 603 CI describes a formulation which contains folic acid and / or dihydrofolic acid and / or its salts and, in connection with mixed populations of microorganisms in the so-called sewer skin, a biofilm in the sewer, is activated, whereby the degradation of the wastewater ingredients also occurs in the sewage treatment plant is improved. Since the compounds used are subject to a loss of effectiveness due to residual oxygen in the wastewater even under essentially anaerobic conditions, a protective gas is used to reduce the introduction of oxygen when the folic acid formulation is introduced.
  • Folic acid preparation proposed to improve its stability in the presence of oxygen, which has a combination of dihydrofolic acid and / or at least one salt thereof and at least one hydroxypolycarboxylic acid and / or at least one salt thereof as a stabilizer.
  • the dihydrofolic acid itself is sensitive to oxidation and appears to act as a kind of sacrificial substance. Their own potential for increasing metabolism or growth in the organisms that absorb them cannot be used.
  • Another object of the invention is to provide an improved formulation for folic acid. Another object of the invention is to provide the highest possible proportion of the folic acid used in a bioactive manner over a period of several weeks. In particular, it is an object of the invention to provide a folic acid formulation which shows an improved bioavailability of the folic acid used compared to previously known formulations.
  • folic acid in relation to the invention in the context of this application includes, in addition to folic acid, tetrahydrofolic acid and tetrahydrofolic acid as well as the derivatives and especially salts of these acids, also in dissolved form, in particular as an aqueous solution.
  • the invention provides a solubilizate containing, in particular consisting of folic acid with a proportion of less than or equal to 3% by weight, preferably less than or equal to 2% by weight, particularly preferably less than or equal to 1% by weight, in particular 0.6% by weight .-%, at least one emulsifier with an HLB value in the range between 13 and 18, which is selected in particular from the group consisting of polysorbate 80, polysorbate 20,
  • Sugar esters from fatty acids E 473
  • at least one medium-chain triglyceride MCT
  • the medium-chain triglyceride being provided in particular by at least one MCT oil and / or at least one vegetable oil, at least one alcohol, in particular glycerol and / or ethanol, at least one alkali, in particular sodium hydroxide solution, and water are available.
  • the solubilizate according to the invention is a colloidally formulated mixture in which folic acid is contained as a bioactive agent.
  • a solubilizate can be created with stable micellar structures, even under physiological conditions.
  • a prerequisite for the absorption of fat-soluble micronutrients by the human or animal body is the formation of so-called "physiological mixed micelles" with the help of bile acids, bile salts and enzymes from the digestive tract.
  • the solubilizate according to the invention therefore has analogous to this natural principle and against the background of optimization
  • the bioavailability of folic acid has a stable micellar structure, and bioavailability can be improved in this way if the micelle is stable under physiological conditions - that is, at a temperature of 37 ° C and pH 1.1 reaches the small intestine undamaged.
  • At least one sugar ester of a fatty acid or a mixture of several sugar esters of fatty acids can also be used as an emulsifier.
  • Individual sugar esters of fatty acids (E 473) or mixtures of at least two sugar esters of fatty acids can be used as sugar esters of fatty acids (E 473).
  • Suitable sugar esters of fatty acids are, in particular, sucrose mono-laurate, sucrose-di-laurate, sucrose-mono-palmitate, sucrose-di-palmitate, sucrose-mono-stearate and sucrose-di-stearate.
  • polysorbate 20 can also be used as an emulsifier within the scope of the invention.
  • the inventor has found that the mixture of polysorbate 80 or polysorbate 20 or a mixture of polysorbate 80 and polysorbate 20 with at least one sugar ester of an edible fatty acid can also be used as an emulsifier within the scope of the invention.
  • Vegetable oils for example, sunflower oil and / or safflower oil can be used.
  • the invention offers the advantage of being able to adjust the composition depending on which other components are to be contained in the solubilizate and in what proportions, its properties with regard to optimizing bioavailability and storage stability and preventing or reducing interactions between folic acid and other substances in the stomach contents of humans and / or animals as well as in the wastewater to be treated is to be provided.
  • the folic acid formulation according to the invention provides folic acid enclosed in micelles.
  • the micelles are mechanically stable. This micellation also protects the folic acid against oxidation. Micellation generally enables a reduction or even suppression of reactions of folic acid with other substances. In this way, when the formulation according to the invention comes into contact with the cells of the organism that absorbs the folic acid, the folic acid can be available undamaged and thus develop its full effectiveness.
  • the formulation of folic acid according to the invention enables, when used in sewage treatment plants, a reduction in sludge formation from biological wastewater treatment and an optimization of biogas production.
  • the emulsifier component in particular the polysorbate component, is at least 45% by weight, preferably in the range between 60% by weight and 95% by weight, particularly preferred is in the range between 73% by weight and 90% by weight. With these values, very stable micelles can be achieved.
  • the at least one lye comprises an aqueous solution of sodium hydroxide solution, the ratio of sodium hydroxide solution to water being in particular 1: 3.
  • the solubilizate or an aqueous solution of the solubilizate has, in particular, a basic pH.
  • a significant improvement in the stability of the micelles in which the folic acid according to the invention is enclosed is achieved according to the invention by adding at least one complexing agent to the solubilizate, in particular ethylenediaminetetraacetic acid and / or ethylenediaminetetraacetate (EDTA) and / or
  • the solubilizate contains up to 25% by weight, preferably up to 12% by weight, glycerol.
  • glycerine By adding glycerine, the proportion of polysorbate in particular can be reduced, depending on the application.
  • the invention offers the possibility that the solubilizate contains up to 20% by weight, preferably up to 15% by weight, of ethanol.
  • the amount of polysorbate can also be reduced by adding ethanol.
  • a reduction in the polysorbate content of a solubilizate is an advantage with regard to the ADI value for polysorbate.
  • the easily accessible determination of the turbidity of the solubilizate provides an indication of the good bioavailability.
  • the turbidity of the solubilizate is preferably less than 10 FNU, preferably less than 5 FNU, as a result of the formulation according to the invention, is measured by measuring scattered light with infrared light according to the regulations of the ISO 7027 standard with a dilution of the solubilizate in a ratio of 1:50 in water at pH 1 1 and 37 ° C.
  • the solubilizate according to the invention can also be incorporated into other fluids, in particular liquids, within the scope of the invention.
  • the small micelles filled with the active ingredient are retained.
  • the invention thus also provides a fluid containing an above-described solubilizate, the fluid being selected from the group which includes additives for wastewater treatment in sewage treatment plants, as well as food, beverages, cosmetics and pharmaceutical products.
  • the fluid can comprise an aqueous dilution of the solubilizate.
  • the invention thus also enables, in particular, the use of a solubilizate or fluid described above as an additive for wastewater treatment in sewage treatment plants or as a food supplement.
  • the invention further provides a method for producing a solubilizate described above with the following steps a) providing a mixture of alcohol, in particular of glycerol and / or ethanol, and water, b) adding the at least one lye and the at least one medium-chain triglyceride, c) adding folic acid, d) adding the emulsifier, in particular polysorbate 80, polysorbate 20, sugar esters from fatty acids
  • step a) heating to a temperature in the range from 50 ° C to 65 ° C, preferably to a temperature in
  • step d) heating to a temperature in the range from 80 ° C to 95 ° C, preferably to a temperature im
  • At least one complexing agent in addition to the alkali, at least one complexing agent, in particular ethylenediaminetetraacetic acid and / or ethylenediaminetetraacetate (EDTA) and / or ethylenediaminetetraacetate calcium disodium complex (EDTA CaNa2-2 H 2 O), is added in step b).
  • EDTA ethylenediaminetetraacetic acid and / or ethylenediaminetetraacetate
  • EDTA CaNa2-2 H 2 O ethylenediaminetetraacetate calcium disodium complex
  • ethylenediaminetetraacetate calcium disodium complex (EDTA CaNa 2 ⁇ 2 H 2 0) is added as a complexing agent, it has proven helpful to heat to a temperature in the range from 50 ° C. to 70 ° C., preferably to one temperature in the range from 55 ° C to 65 ° C, particularly preferably at a temperature in the range from 58 ° C to 62 ° C.
  • step b) bl) the at least one complexing agent is dissolved in the at least one alkali, in particular in an aqueous solution of the at least one alkali.
  • the folic acid used in the exemplary embodiments described below was obtained from Welding GmbH & Co. KG, Hamburg, Germany, from Koninklijke DSM N.V., Heerlen, Netherlands, from Zhejiang
  • TEGO SMO 80 V FOOD The material "TEGO SMO 80 V FOOD” from Evonik Nutrition & Care GmbH, Essen, Germany, was used as the source for polysorbate 80.
  • the product complies with the EU requirements for the food additive E 433 mentioned TEGO SMO 80 V from Evonik as polysorbate 80, for example also Crillet 4 / Tween 80-LQ- (SG) from CRODA GmbH, Nettetal, Germany or Lamesorb SMO 20 and Kotilen-O / 1 VL from Univar or Kolb Distributions AG, Hedingen, Switzerland can be used.
  • glycerine from CREMER OLEO GmbH & Co. KG was used as the glycerine. According to the manufacturer, the glycerine content of this product is at least 99.5%. Alternatively, for example, the product “Glycamed 99.7%” from Glaconchemie GmbH, Merseburg, Germany can also be used.
  • MCTs Medium-chain triglycerides
  • the medium-chain fatty acids include caproic acid, caprylic acid, capric acid and lauric acid. These are saturated fatty acids, which occur naturally in tropical vegetable fats such as coconut oil and palm kernel oil. To a small extent, they are also contained in milk fat. There is no pure MCT oil in nature, but pure MCT oils can be obtained synthetically. In the context of the invention, individual MCTs or a mixture of different MCTs can be used as medium-chain triglycerides.
  • EDTA-NaOH solution was used for the exemplary embodiments described below. This corresponds to a composition of sodium hydroxide solution (1: 3) and ethylenediaminetetraacetate (EDTA), AppliChem GmbH, Darmstadt, Germany, or ethylenediaminetetraacetate calcium disodium complex (EDTA CaNa2 2 H2O) as the product Solvitar® from Nouryon, Amsterdam, Netherlands, formerly AkzoNobel Specialty Chemicals.
  • the sodium hydroxide solution was prepared from one part of NaOH pellets and three parts of water. The NaOH toes were obtained from Spolchemie, Usti nad Labern, Czech Republic.
  • Distilled water was used as the water.
  • the 15% EDTA-NaOH solution corresponds to 1.5 g EDTA and 8.5 g sodium hydroxide solution.
  • the sodium hydroxide solution consists of one part of NaOH toes and three parts of water.
  • glycerine and water are mixed and heated to a temperature in the range from 53 ° C to 57 ° C.
  • the EDTA solution and the MCT oil are then added and the mixture is homogenized while maintaining the temperature in the range from 53 ° C. to 57 ° C. while stirring. This means that it is stirred so vigorously that the components initially mixed with one another combine with one another homogeneously, with in particular essentially no residues remaining.
  • the folic acid is then added while maintaining the temperature in the range from 53 ° C to 57 ° C and.
  • the folic acid is incorporated with stirring and homogenized with the other components.
  • Polysorbate 80 is then added.
  • the temperature is increased to a value in the range from 83 ° C. to 87 ° C. and the product is homogenized.
  • the mixture is cooled to a temperature below 60 °.
  • the folic acid solubilizate is yellow and transparent.
  • the turbidity is a maximum of 1.5 FNU under physiological conditions, the measurement being carried out as described above.
  • the folic acid solubilisate is then bottled and stored in a dark and cool place, i.e. below 25 ° C.
  • Ethyldiamine tetraacetate calcium disodium complex (EDTA CaNa2 ⁇ 2 H2O) and NaOH solution are used.
  • the NaOH solution is prepared as described in embodiment 1. 8.5 g of this NaOH solution are mixed with 1.5 g
  • Ethyldiamine tetraacetate calcium disodium complex used as 10 g of the 15% (EDTA CaNa2 ⁇ 2 H2O) -NaOH solution.
  • the temperature is increased to a value in the range from 58.degree. C. to 62.degree.
  • the further processing corresponds to that described above.
  • This folic acid solubilizate is also yellow and transparent.
  • the turbidity is a maximum of 1.5 FNU under physiological conditions, the measurement being carried out as described above.
  • the clarity of the solubilizate according to the invention is retained; when heated further, it becomes cloudy the solubilizate. On cooling, the cloudiness is reversible and the solubilizate becomes clear again.
  • Whether a sufficiently complete homogenization of the components to form a solubilizate according to the invention has been completed is checked during production by measuring the clarity of the product with the aid of a laser beam.
  • a laser beam measurement can be carried out, for example, by illuminating the sample with the aid of a commercially available laser pointer, in particular with a wavelength in the range between 650 nm and 1700 nm (spectral color red), and subsequent visual inspection of the illuminated or transilluminated solubilizate.
  • the control is not carried out by taking samples and thus outside the reaction vessel, but in the reaction vessel.
  • the laser beam is directed through a sight glass, which is located on the front of the reaction vessel, perpendicular to the reaction vessel. If only one point of light appears on the rear inner side of the reaction kettle, completely free of scattering, the resulting particle structures in the reaction kettle are smaller than the wavelength of visible light and thus an optical confirmation that the micellation process has been completed.
  • the folic acid content in the solubilizate can also be set significantly higher than in the examples shown, depending on the application.
  • this effectiveness can be attributed to the improved bioavailability of the folic acid solubilized according to the invention compared to known formulations and can already be read from the particularly low turbidity of the solubilizate, which can be understood as a kind of parameter for bioavailability. It is evident to the person skilled in the art that the invention is not restricted to the examples described above, but rather can be varied in many ways. In particular, the features of the individually illustrated examples and embodiments or developments can also be combined with one another or exchanged for one another.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Water Supply & Treatment (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Environmental & Geological Engineering (AREA)
  • Hydrology & Water Resources (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Dispersion Chemistry (AREA)
  • Mycology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
PCT/EP2020/073310 2019-08-29 2020-08-20 Folsäure-solubilisat WO2021037656A1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202080061116.XA CN114364268A (zh) 2019-08-29 2020-08-20 叶酸增溶物
EP20761181.5A EP4021412A1 (de) 2019-08-29 2020-08-20 Folsäure-solubilisat

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE202019104734.8U DE202019104734U1 (de) 2019-08-29 2019-08-29 Folsäure-Solubilisat
DE202019104734.8 2019-08-29

Publications (1)

Publication Number Publication Date
WO2021037656A1 true WO2021037656A1 (de) 2021-03-04

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ID=72234823

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2020/073310 WO2021037656A1 (de) 2019-08-29 2020-08-20 Folsäure-solubilisat

Country Status (4)

Country Link
EP (1) EP4021412A1 (zh)
CN (1) CN114364268A (zh)
DE (1) DE202019104734U1 (zh)
WO (1) WO2021037656A1 (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023139105A1 (de) 2022-01-20 2023-07-27 Solmic Biotech GmbH Topisch anwendbare zusammensetzung enthaltend solubilisate lipophiler wirkstoffe
EP4275694A1 (de) 2022-05-13 2023-11-15 Solmic Biotech GmbH Verwendung von solubilisaten in erzeugnissen zur topischen anwendung

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0319598B1 (de) 1987-12-07 1991-09-25 Holger Blum Stabilisierte wässrige Folsäurezubereitung
DE4213603C1 (en) 1992-04-24 1993-06-03 Allied Colloids Mfg. Gmbh, 2000 Hamburg, De Treating waste water by addn. of (di:hydro)folic acid or salts - activating bio:film on inner wall of pipes to accelerate breakdown of components in the water
US20080249191A1 (en) * 2007-03-30 2008-10-09 Nof Corporation Solubilizing composition
WO2011066937A1 (de) * 2009-12-01 2011-06-09 Aquanova Ag Als emulgator wirkende zusammensetzung für wasserlösliche solubilisate hydrophober verbindungen
EP3216443A1 (en) * 2016-03-10 2017-09-13 Athenion AG Beverage preparation capsule for delivery of a solubilisate

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19936545A1 (de) * 1999-08-03 2001-02-08 Hexal Ag Neue pharmazeutische Zusammensetzung zur nasalen Anwendung von wasserlöslichen Wirkstoffen
DE102004045622A1 (de) * 2004-09-17 2006-03-30 Aquanova German Solubilisate Technologies (Agt) Gmbh Konservierungsmittel-Zusammensetzungen
ES2602812T3 (es) * 2008-12-01 2017-02-22 Aquanova Ag Protección contra la oxidación integrada micelarmente para colorantes naturales
DE202012012130U1 (de) * 2012-12-19 2014-03-21 Aquanova Ag Curcuminsolubilisat
KR20200029002A (ko) * 2017-07-11 2020-03-17 아쿠아노바 아게 커큐민 및 선택적으로 적어도 1종의 다른 활성 물질을 갖는 가용화물

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0319598B1 (de) 1987-12-07 1991-09-25 Holger Blum Stabilisierte wässrige Folsäurezubereitung
DE4213603C1 (en) 1992-04-24 1993-06-03 Allied Colloids Mfg. Gmbh, 2000 Hamburg, De Treating waste water by addn. of (di:hydro)folic acid or salts - activating bio:film on inner wall of pipes to accelerate breakdown of components in the water
US20080249191A1 (en) * 2007-03-30 2008-10-09 Nof Corporation Solubilizing composition
WO2011066937A1 (de) * 2009-12-01 2011-06-09 Aquanova Ag Als emulgator wirkende zusammensetzung für wasserlösliche solubilisate hydrophober verbindungen
EP3216443A1 (en) * 2016-03-10 2017-09-13 Athenion AG Beverage preparation capsule for delivery of a solubilisate

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023139105A1 (de) 2022-01-20 2023-07-27 Solmic Biotech GmbH Topisch anwendbare zusammensetzung enthaltend solubilisate lipophiler wirkstoffe
EP4275694A1 (de) 2022-05-13 2023-11-15 Solmic Biotech GmbH Verwendung von solubilisaten in erzeugnissen zur topischen anwendung

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CN114364268A (zh) 2022-04-15
EP4021412A1 (de) 2022-07-06
DE202019104734U1 (de) 2020-12-01

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