EP1807047A2 - Ascorbate de sodium solubilise - Google Patents

Ascorbate de sodium solubilise

Info

Publication number
EP1807047A2
EP1807047A2 EP05743331A EP05743331A EP1807047A2 EP 1807047 A2 EP1807047 A2 EP 1807047A2 EP 05743331 A EP05743331 A EP 05743331A EP 05743331 A EP05743331 A EP 05743331A EP 1807047 A2 EP1807047 A2 EP 1807047A2
Authority
EP
European Patent Office
Prior art keywords
polysorbate
weight
solubilizate
sodium
ascorbic acid
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP05743331A
Other languages
German (de)
English (en)
Inventor
Dariush Behnam
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aquanova AG
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
Publication of EP1807047A2 publication Critical patent/EP1807047A2/fr
Withdrawn legal-status Critical Current

Links

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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions

Definitions

  • Ascorbic acid has found widespread use as a reducing agent, the use of which is made more difficult because it is not sufficiently stable in aqueous solution. Thus, in an aqueous ascorbic acid solution after 30 days only about 70% of the added ascorbic acid are present.
  • An increased resistance of the reducing agent in aqueous solution is achieved by derivatization of the antioxidants.
  • sodium ascorbic phosphate or ascorbyl palmitate are frequently used.
  • the ascorbic acid derivatives are many times more expensive than pure ascorbic acid.
  • the ascorbic acid derivatives tend to crystallize out in higher concentrations and lead to discoloration of the end product.
  • the above-mentioned reducing agent is still too low in effectiveness as a protection for fatty substances due to its low solubility in the fats and oils used in the products mentioned above.
  • the reducing agent adheres to the outside of the Fettröpchen and can not develop its antioxidant effect into the interior of the fat blends.
  • Document EP 1338271 A1 describes a fat and water-soluble solubilisate with ascorbic acid containing polysorbate 80 which renders ascorbic acid fat-soluble.
  • the addition of a triglyceride increases the stability of the solubilizate.
  • this document discusses the combined use of ascorbic acid and tocopherol solubilisates in which the mixed solubilizate contains 3% ascorbic acid and 7% tocopherol.
  • the patent DE 19647352 C2 describes a water-soluble solubilisate of the fat-soluble reductone ubiquinone Q 10 with the aid of the solubilizer polyoxyethylene sorbitan monooleate (polysorbate 80), which can be vitaminized by adding vitamin E, which is likewise fat-soluble.
  • the invention has for its object to provide a reducing agent, which is suitable for the protection of fatty foods in readily miscible liquid, water and fat-soluble form. This should be very stable over many months in high concentration.
  • a solubilizate which consists of an aqueous solution of alkali and / or alkaline earth salts of ascorbic acid for food, cosmetics and the like and an emulsifier having an HLB value of 9 to 18, for example polysorbates or cremophore ,
  • the alkali and / or alkaline earth salts of ascorbic acid because of their non-acidic properties in an aqueous environment, are particularly well suited to the above-mentioned object, especially in such uses (e.g., ointments) where a slightly acidic effect of ascorbic acid is not desired.
  • the solubilizate is clear at room temperature and almost gel-like, turbid-free verdü ⁇ nbar with water and can be when heated to about 35 ° C both with aqueous and greasy end products from the cosmetics or food sector, especially in sausage and Fleischpr ⁇ dukten alier kind without further Effortlessly mixing the processing steps homogeneously.
  • the use of sodium L-ascorbate, in crystalline form, as an additive in sausage and ham production is known.
  • the alkali metal and / or alkaline earth metal salts used are the sodium L-ascorbate, which may expediently be present in the solubilizate in a proportion of about 9% by weight to about 11% by weight. It is also advisable to add to the solubilizate one or more medium-chain triglycerides in a content of preferably about 8% to about 11% by weight, wherein the triglycerides may suitably contain caprylic acid and / or capric acid.
  • the solubilisate may contain, instead of the triglycerides, one or more vegetable oils such as thistle oil, rapeseed oil, soybean oil or sunflower oil in substantially equal proportions.
  • the solubilizate contains one or more tocopherols or a mixed tocopherol and / or derivatives thereof, such as the acetate of tocopherol, suitably in a content of about 9 wt% to about 11 wt% as a vitamin E acetate.
  • the solubilizate according to the invention may contain a non-ionic emulsifier which is authorized in the country concerned for foodstuffs for the purpose according to the invention. Particularly recommended among these are those which have an HLB value between 9 and 18, because these lead to 5 optically clear end products.
  • a polysorbate preferably polysorbate 80 or polysorbate 20, which has an HLB value of 15 and has a sufficient content of hydrophilic and hydrophobic groups is suitable for the invention.
  • the polysorbate content in the solubilizate according to the invention is suitably between about 50% by weight and about 70% by weight.
  • the inventive production process for said solubilizate is characterized in that the alkali and / or alkaline earth salt of ascorbic acid, suitably the sodium L-ascorbate, in warm water, preferably having a temperature of about 6O 0 C to about 85 ° C has , is added in the heat i 5 an emulsifier having an HLB value of 9 to 18 of the solution and stirred until dissolved clarity. It is advisable to dissolve in the warm solution one or more medium-chain triglycerides containing, for example, caprylic and / or capric acid, and then to stir in the emulsifier, suitably a polysorbate such as polysorbate 80 or polysorbate 20.
  • the alkali and / or alkaline earth salt of ascorbic acid suitably the sodium L-ascorbate
  • warm water preferably having a temperature of about 6O 0 C to about 85 ° C has
  • an emulsifier having an HLB value of 9 to 18 of the solution and stirred
  • tocopherols or derivatives thereof such as tocopherol acetate
  • tocopherol acetate can be stirred into the solution.
  • medium-chain triglycerides one or more vegetable oils such as thistle oil, rapeseed oil, soybean oil or sunflower oil can be used.
  • solubilizate according to the invention can be used as an additive to foods, especially 5 to meat and sausage products of all kinds, for the protection of oils, fats, emulsions and to medicaments.
  • the ascorbates are relatively easily oxidizable. Because of this property, in continuation of the invention, the durability of the alkali metal and / or alkaline earth metal salts is further improved by the solubilisate micelles each additionally having a content of one or more tocopherols or a mixed tocopherol. Each solubilisate micelle then contains both the ascorbate and the tocopherol and / or a mixture of individual ascorbate and tocopherol micelles.
  • solubility it is possible, for example, to start from the alkali salt sodium L-ascorbate, which provides its color stability, above all in the case of meat and sausage products.
  • tocopherol, ⁇ -tocopherol, tocopherol derivatives or mixed tocopherols can be used in the solubilizate.
  • the sodium-L-ascorbate content of the formulation according to the invention which may be up to 11% by weight, remains virtually lossless for months.
  • the vitamin E acetate content of the solubiiisate is about 10% by weight.
  • the polysorbate content is suitably about 69% by weight.
  • the sodium L-ascorbate / vitamin E acetate solubilisate according to the invention can easily be added to foods, medicaments, cosmetics (skin and hair care products) with the consequence that the resistance of these products is substantially increased.
  • the polysorbate content of the solution according to the invention unfolds a kind
  • Retard function for the antioxidant properties of ascorbic acid and optionally of tocopherol for the easily oxidizable ingredients of pharmaceutical formulations and foods is maintained over a much longer period of time.
  • a process for the preparation of the solubiiisate according to the invention provides that alkali and / or alkaline earth salts of ascorbic acid dissolved in warm water and in the heat an emulsifier having an HLB value of 9 to 18, preferably a polysorbate added and stirred until clear ,
  • the emulsifier polysorbate 20, or polysorbate 80 is added at a temperature of about 70 to 75 0 C and the mixture heated with stirring until clarity and homogeneity for several minutes.
  • spherical micelles are formed.
  • the tocopherol oil is added to the aqueous solution of alkali metal and / or alkaline earth metal salts of ascorbic acid at a temperature of about 85 ° C., which leads to the formation of an emulsion. Then, at a temperature of about 85 0 C, the emulsifier polysorbate 20 is added. The mixture is kept under stirring for a few minutes at the indicated temperature for clarity and homogeneity. During the addition of the emulsifier, spherical micelles are formed in which both the ascorbates and vitamin E molecules are entrapped. Instead of tocopherol or in addition to this is also an addition of medium-chain triglycerides such as liquid vegetable fats into consideration.
  • medium-chain triglycerides such as liquid vegetable fats into consideration.
  • the Polysorbatmoleküle store at the beginning of the micelle formation areally together, it comes to the association of the vitamin E molecules to the hydrophobic areas of the emulsifier molecules.
  • the critical micelle formation concentration is exceeded, globular aggregates begin to form globular micelles, in the interior of which an aqueous compartment containing dissolved alkali and / or alkaline earth salts of ascorbic acid is enclosed.
  • the micelles have a double-walled shell of radially arranged polysorbate molecules in an aqueous medium.
  • the polysorbate molecules of the inner shell with their hydrophilic section enclose the inner compartment with the enclosed alkali and / or alkaline earth salt solution of ascorbic acid and the hydrophilic sections of the polysorbate molecules of the outer shell arrange outwards.
  • Vitamin E is associated with the hydrophobic portions of the polysorbate molecules.
  • the antioxidants are therefore micellised together in the solubiüsate. Since the reducing agent enclosed in the micelles are released only delayed, the antioxidant effect of the solubilizate in the mentioned agents remains effective longer than, for example, the sole addition of ascorbyl palmitate, so one of the above-mentioned ascorbic acid derivatives.
  • the inclusion of the water-insoluble vitamin E in the micelle causes a marked stabilization of the ascorbic acid, which is highly decomposition-prone as an endiol.
  • the ascorbic acid is additionally protected against decomposition, which leads to an increased stability of the latter.
  • solubilizate according to the invention it is of great advantage that the water-soluble sodium ascorbate and the fat-soluble vitamin E are present in mixed micelles in both water-soluble and fat-soluble form.
  • solubilisate To allow longer shelf life of the formulation, it is advisable to add one or more medium-chain triglycerides or vegetable oils such as thistle oil to solubilisate, the proportion of which should be about 10 to 11% by weight, which reliably prevent precipitation of parts of the reducing agent.
  • the inclusion of the antioxidant substances in micelles by the emulsifier prevents the ascorbic acid or vitamin E from exerting its effect already in the middle digestive tract, ie in the stomach and duodenum, during oral administration of the solubilizate according to the invention.
  • the micellised active substances mentioned above are absorbed without damage first in the small intestine (without the involvement of bile acid, bile salts and enzymes quantitatively up to several times better).
  • Example 1 of a ten percent sodium ascorbate solubilizate with triglycerides
  • Example 2 As in Example 1, dissolve about 10 g of sodium L-ascorbate in about 24 g of distilled water and add about 55 g of polysorbate 80 to this solution. This mixture is stirred after heating to about 70 to 75 0 C until the mixture is transparent and
  • this mixture are added about 684.5 g of polysorbate 20 and about 85 0 C is stirred as long as the mixture has to transparency and homogeneity achieved.
  • the resulting solubilizate is allowed to cool slowly and filled at about 60 C C 5.
  • T-90 consisting of 90% by weight of tocopherols, composed as follows: 14% ⁇ -tocopherol, 2% ⁇ -tocopherol, 60% ⁇ -tocopherol and 24% ⁇ -tocopherol.
  • solubilizate is allowed to cool slowly and fills it at about 60 0 C.
  • Polysorbate 80 added. This mixture is heated to about
  • solubilizate is allowed to cool slowly and filled at about 60 0 C.
  • the production process can also be designed so that the sodium L-ascorbate in water from 50 ° C to 6O 0 C for
  • the mixture is heated to about 75 0 C to about 85 0 C, so that a clear solubilizate is formed. After cooling to at least 5O 0 C, the addition of the triglyceride is carried out with stirring. The temperature must not exceed 50 0 C.
  • Material The same material is used as in Example 8, except that the polysorbate 20 is replaced by the same amount of polysorbate 80.
  • the solubilizates of Examples 1 to 7 have excellent and long shelf life.
  • the stable solubilizates prepared according to Examples 8 and 9 are intended for immediate use within the scope of intended uses.
  • the quantitative information on the substances used by themselves is not essential, but only the ratio of this information.
  • 5750 g of water can be used, and 50 times higher values of these substances can be used to achieve the same result.
  • the Poiysorbate can be used in the context of the invention, also RH series Cremopore, A 6, A 25, EL, whose HLB values are between 10 and 17.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Food Science & Technology (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Dispersion Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)

Abstract

L'invention concerne un produit solubilisé constitué d'une solution aqueuse de sels alcalins et/ou alcalinoterreux de l'acide ascorbique pour des produits alimentaires, cosmétiques et similaires, et constitué d'un émulsifiant ayant une valeur HLB comprise entre 9 et 18, du polysorbate par exemple. Le produit solubilisé selon l'invention comprend en outre, de manière avantageuse, un ou plusieurs triglycérides à chaîne moyenne et/ou un ou plusieurs tocophérols.
EP05743331A 2004-10-20 2005-05-09 Ascorbate de sodium solubilise Withdrawn EP1807047A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004051245A DE102004051245A1 (de) 2004-10-20 2004-10-20 Vitamin C-Solubilisat
PCT/EP2005/004993 WO2006042574A2 (fr) 2004-10-20 2005-05-09 Ascorbate de sodium solubilise

Publications (1)

Publication Number Publication Date
EP1807047A2 true EP1807047A2 (fr) 2007-07-18

Family

ID=34980139

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05743331A Withdrawn EP1807047A2 (fr) 2004-10-20 2005-05-09 Ascorbate de sodium solubilise

Country Status (4)

Country Link
US (1) US20090048334A1 (fr)
EP (1) EP1807047A2 (fr)
DE (1) DE102004051245A1 (fr)
WO (1) WO2006042574A2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102010033458B4 (de) 2010-08-05 2016-03-10 Helvista Ag Emulgierte Lektinzusammensetzungen und ihre Verwendung
DE102011105703A1 (de) 2011-06-22 2012-12-27 Wolfgang Langhoff Diätetikum zur Behandlung mitochondrialer Dysfunktionen
WO2023200792A1 (fr) * 2022-04-11 2023-10-19 Impossible Foods Inc. Méthodes de traitement de réducteur pour précurseurs de produits alimentaires

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1464797A (en) * 1973-08-02 1977-02-16 American Cyanamid Co Injectable liquid vitamin preparation
DE19609476A1 (de) * 1996-03-11 1997-09-18 Basf Ag Stabile zur parenteralen Verabreichung geeignete Carotinoid-Emulsionen
DE60014255T2 (de) * 1999-07-06 2005-11-03 Dsm Ip Assets B.V. Zusammensetzung, die fettlösliche Substanzen in einer Kohlenhydratmatrix enthält
US6274169B1 (en) * 1999-08-02 2001-08-14 Abbott Laboratories Low oxygen content compostions of 1α, 25-dihydroxycholecalciferol
US6300377B1 (en) * 2001-02-22 2001-10-09 Raj K. Chopra Coenzyme Q products exhibiting high dissolution qualities
DE10158447B4 (de) * 2001-11-30 2005-02-10 Aquanova German Solubilisate Technologies (Agt) Gmbh Ascorbinsäure-Solubilisat
AU2003250967B2 (en) * 2002-07-24 2009-05-28 Basf Aktiengesellschaft Ascorbic acid salt suspensions and use thereof as antioxidants

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006042574A2 *

Also Published As

Publication number Publication date
WO2006042574A3 (fr) 2006-08-03
WO2006042574A2 (fr) 2006-04-27
US20090048334A1 (en) 2009-02-19
DE102004051245A1 (de) 2006-04-27

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