US20030087789A1 - Emulsion containing a plant extract, method for producing said emulsion and for obtaining a plant extract - Google Patents

Emulsion containing a plant extract, method for producing said emulsion and for obtaining a plant extract Download PDF

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Publication number
US20030087789A1
US20030087789A1 US10/239,929 US23992902A US2003087789A1 US 20030087789 A1 US20030087789 A1 US 20030087789A1 US 23992902 A US23992902 A US 23992902A US 2003087789 A1 US2003087789 A1 US 2003087789A1
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emulsion
triterpene
birch
solvent
extract
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Armin SCHEFFLER
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Amryt Pharmaceuticals Designated Activity Co
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Individual
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Priority claimed from DE10015353A external-priority patent/DE10015353A1/de
Priority claimed from DE10056902A external-priority patent/DE10056902A1/de
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Publication of US20030087789A1 publication Critical patent/US20030087789A1/en
Priority to US11/748,304 priority Critical patent/US7482383B2/en
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Assigned to AMRYT PHARMACEUTICALS DESIGNATED ACTIVITY COMPANY reassignment AMRYT PHARMACEUTICALS DESIGNATED ACTIVITY COMPANY MERGER (SEE DOCUMENT FOR DETAILS). Assignors: AMRYT RESEARCH LIMITED
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    • 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
    • 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
    • A61K36/02—Algae
    • A61K36/04—Rhodophycota or rhodophyta (red algae), e.g. Porphyra
    • 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)
    • 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)
    • A61K36/54—Lauraceae (Laurel family), e.g. cinnamon or sassafras
    • 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)
    • A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
    • A61K36/736—Prunus, e.g. plum, cherry, peach, apricot or almond
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling

Definitions

  • the present invention concerns a process for obtaining triterpenes and/or their components as well as an emulsion, of which the aqueous and fatty phases are emulsified by a plant extract, wherein the plant extract contains at least one triterpene and/or a triterpene divertive and the emulsion further contains at least one oil and/or fat and water.
  • the present invention concerns a process for producing the emulsion as well as the use of the triterpenes for production of cosmetics and pharmaceuticals.
  • Betulin containing plants are widely distributed in the plant kingdom. They belong primarily to the Hamamelididae (angiosperm plants), where in one single species in the order fagales (birch relatives), and more particularly in the family of the betulaceen (birches), the content of betulin accumulates in the outer bark (review article: Hayek, E. W. et al., (1989), A Bicentennial of Betulin, Phytochemistry, 28(9), pages 2229-2242).
  • the white part of the birch bark, in particular the species betula pedula, betula verrucosa and betula papyfera can contain more than 30% betulin.
  • Betulin is a pentacyclic triterpene with a lupan skeleton, which is also referred to as betulinol, trochoton, birch camphor and (coryli) resinol.
  • the characterizing feature of the lupan group is a ring with five carbon atoms within the pentacyclic system, which contains an ⁇ -isopentyl group in the position C-19.
  • Betulin is further characterized by a high thermal stability, its melting point lies between 250 and 260° C., wherein even high values are obtained after sublimation of the re-crystallized product.
  • birch bark is used for production of birch bark oil, which has also been used for treatment of rheumatism and as aroma therapy (Hansel, R. et al., (Hrsg.), (1994), Drug A-D, Springer Publishing House, Chapter Betula, pages 502-511; Hyek, E. W. supra).
  • birch extracts as bath salts for treatment, particularly for sweaty feet, as well as additives to shampoos as a hair care agent is known (Nowak, G. A., (1966), Cosmetic and Medicinal Properties of the Birch, Amer. Perfumer Cosmet., 81, page 37).
  • aqueous extracts from birch leaves have been employed, which contain practically no betulin.
  • Betulinic acid derivates a new class of human immunodeficiency virus type 1 specific inhibitors with a new mode of action, J. Med. Chem. 39, pages 1056-1068; Hayek, E. W. et. al., supra).
  • an anti-inflammatory, cortisone like effect as well as cytostatic effect upon use in vitro against various tumor cell lines of betulin and betulin derivatives has been shown (Carmen Recio, M., et. al. (1995), Investigations on the steroidal anti-inflammatory activity of triterpenoids from Diospyros leucomelas, Planta Med. 61, pages 9-12); Yasukawa, K., et. al., (1991), Sterol and triterpene derivates from plants ( . . . ), Oncogene 48, pages 72-76).
  • the disadvantage of the sublimation technique is the fact that the content is obtained only with very low yield, which necessitates the use of large amounts of starting materials.
  • a particular disadvantage of the sublimation technique is the simultaneous occurrence of tar-like decomposition products from other cork/bark components, which necessitates multiple re-sublimation or re-crystallization.
  • betulin is relatively poorly soluble in the mentioned solvents and the extraction can only be carried out with high investment in time.
  • multiple re-crystallizations are necessary.
  • the best results are obtained with higher boiling carbohydrates (Eckermann, C. and Ekman, R. (1985), supra).
  • Solvents in which betulin is highly soluble, such as for example pyridine and tetrohydrofuran, are generally considered to be toxins. They are dismissed on the basis of their health risk and their not insubstantial handling risks during extraction.
  • a further disadvantage of the mentioned solvents is that substantial amounts of brown, undesired substances are dissolved at the same time, of which the later separation is extremely complex and costly and uneconomical. Accordingly, until today there is no efficient process for obtaining betulin from birch cork, whereby betulin can be produced in large amounts, with a high degree of purity and without using strong hazardous solvents.
  • U.S. Pat. No. 5,647,976 a reaction vessel is described, which can be employed for extraction of contents with solvents with high pressure and elevated temperature.
  • This reaction vessel is characterized by a lock, which makes it possible to introduce solvents in the reaction vessel and to remove them therefrom, without having to disturb the lock. In this manner contamination of the solvent is effectively prevented.
  • the reaction vessel is simple to operate, so that it can be operated even by untrained personnel.
  • U.S. Pat. No. 5,647,976 essentially describes the mentioned reaction vessel, however gives not direction as to how to carry out an extraction process. Besides this, it contains no indication regarding the quality and purity of the contents which have been isolated in the reaction vessel.
  • a disadvantage of the process is in particular that it may be suitable for extracting soluble substances in an analytic sample, however is not or is only poorly suitable for preparative production and yielding of components in greater amounts and purity, since it is precisely in such processes that contamination of the sample leads to defects in the degree of purity of the extracted components. Further, the process as described in U.S. Pat. No. 5,785,856 as conceived is limited to the analytical realm. The document provides no indication regarding obtainable degrees of purity and the possibility for scaling up to industrial scale.
  • anti-microbial effective preservatives were added to the described emulsifiers, whereby primarily benzoic acid derivatives were employed (Pasich, J., 1965), Triterpenoid emulsifiers of plant origin. V. Emulsifying properties of Betulin and certain of its esters. Farm. Polska 21, Nr. 17-18, pages 661-666).
  • the present invention further addresses the task of providing a triterpene containing emulsion which contains pharmaceutically active components and at the same time is sufficiently stable for a longer period of time without the addition of preservatives. Besides this, the emulsion should be capable of preparation in a simple manner.
  • the first task is solved thereby, that in the inventive process for obtaining of triterpenes from plants and/or their components the plant parts are first washed at 20° C. to 70° C. in a solvent in which the triterpenes are not soluble or only slightly soluble.
  • the triterpenes are extracted with a solvent under increased pressure and elevated temperature.
  • a cooling and simultaneous depressurization of the triterpene containing solution whereby the triterpenes precipitate in the solvent in extremely small particles and then more triterpene crystallizes onto these particles upon further cooling.
  • they are washed following filtration at room temperature with a fresh solvent.
  • the expression “washing ( . . . ) in a solvent, in which the triterpene ( . . . ) is not or is only slightly soluble” means that the solubility of the triterpene is not more than 1 g/liter.
  • the extraction of the triterpene occurs with solvent under increased pressure and elevated temperature, in certain cases in the supercritical region.
  • solvents for example supercritical carbon dioxide as well as carbohydrates in the supercritical region as well as liquid carbohydrates under elevated pressure or mixtures of different carbohydrates.
  • step (e) Prior to washing [step (e)] it is advantageous that it is not necessary to dry the filter cake in a further process step. Thereby the process is particularly simple to carry out.
  • step (e)] the washing of the triterpene [step (e)] can itself be carried out under normal conditions, thereby keeping the inventive process particularly simple and economical.
  • the inventive process is carried out continuously.
  • the plat material and cold solvent are conveyed through a pressure-tight tube by pumping, and washed in a counter-current at 20° C. to 70° C.
  • the washed plant material is conveyed in a second, likewise pressure-tight and heatable tube or pipe and extracted in counter-current with fresh, supercritical heated or liquid solvent.
  • the discharge of the wash solution and the extraction solution occurs respectively via a filter system.
  • the plant parts are conveyed counter-current to the solvent flow on the basis of their different density and are discharged at the end opposite to the solvent discharge end.
  • the extract solution is—with maintenance of the pressure in the extraction system—conveyed to spray nozzles via a valve system and it is only here that it is finally reduced in pressure.
  • Birch bark is available in large amounts as an economical raw material in particular as waste products in the pulp industry.
  • the triterpenes are obtained from birch bark, preferably from the white part of the birch bark, which is also referred to as birch cork.
  • “Separated birch cork” refers to both the white outer layer when stripped by hand, which is sloughed off outwardly as cork skin by the trunk of the birches and thus lies outside of the actual bark, as well as the subsequently separated birch cork separated for example with the aid of a hammer mill and a flotation process from a total skinning.
  • the triterpene is obtained in a purity of at least 80%, preferably 85%, in particular 90%, particularly preferably above 90%.
  • the main component of the extracted triterpene is betulin, wherein its content is at least 80%, preferably 85%, in particular 90%, particularly preferably above 90%.
  • a low boiling carbohydrate or a mixture which includes a low boiling carbohydrate since a low boiling carbohydrate can be subsequently very easily removed.
  • the boiling point of the employed carbohydrate, or as the case may be the mixture preferably lies below 100° C.
  • Particularly preferred is the employment of n-pentane, n-hexane or n-heptane, since all are inexpensive, do not harbor any special health hazards and are available in sufficient quantities in good quality.
  • the first washing step is carried under a pressure of 1 to 300 bar, preferably 10 to 35 bar, particularly preferably about 25 bar.
  • the actual extraction occurs preferably at a temperature of 50 to 200° C., preferably 140 to 160° C., particularly preferably about 150° C. and under a pressure of 1 to 300 bar, preferably 10 to 35 bar, particularly preferably about 25 bar.
  • these extraction conditions large amounts of pure triterpenes, in particular pure betulin, are obtained.
  • the inventive process has also been found to be of particular advantage, when the crystallization of the triterpene occurs as micro-crystallization with an average particle size of ⁇ 40 ⁇ m, in particular from 2 to 32 ⁇ m.
  • a further atribute of the present invention is an emulsion, of which the aqueous and fatty phases are emulsified by a plant extract, wherein the plant extract includes at least one triterpene and/or at least one derivative of a triterpene and the emulsion further includes at least one oil and/or fat and water.
  • the triterpene and/or its derivative preserves and emulsifies the emulsion. Besides this, it is pharmaceutically active. Thereby it is in particular achieved, that the emulsion contains no supplemental preservative, and thus possesses a particularly high degree of purity and a good compatibility above all with problematic applications to damaged skin.
  • the plant extract is herein an extract of birch bark, preferably from the white part of the birch bark, which is referred to as birch cork.
  • the plant extract contains at least one of the substances betulin, betulinic acid, betulonic acid, lupeol (lupol), erythrodiol, allobetulin, phellonic acid, hydroxy-lactone, betulonic aldehyde, ⁇ -amyrin, oleanolic acid, ursolic acid, esterified betulin and/or ⁇ -sitosterol.
  • These plant constituents could be employed individually as well as mixed with each other in various combinations in the inventive emulsion.
  • a particularly suitable combination is comprised of betulin>80%, betulinic acid ⁇ 10%, lupeol ⁇ 3%, oleanolic acid ⁇ 4%, erythrodiol ⁇ 4% and water ⁇ 1%.
  • the emulsion preferably contains the triterpene and/or its derivative in a concentration of 2 to 10%. Depending upon the desired consistency, the proportion of the triterpene and/or its derivative can be varied in the mentioned concentration range. For the employment of a fluid lotion the emulsion exhibits for example a concentration of the triterpene and/or its derivative of 2 to 3.5%. If the emulsion is used in the form of a cream, the concentration of the triterpene and/or its derivative is preferably 3.5 and 10%.
  • the oily and/or fatty component of the emulsion can be selected from any of the dermatological and cosmetic known oils and fats. Particularly suitable are animal and plant fats such as jojoba oil, peanut oil and olive oil. Particularly preferred is the use of avocado and/or almond oil.
  • moisturizers and/or thickeners and solidifiers can be employed.
  • moisturizers there can be employed in particular glycerin and urea or carbamide.
  • concentrations of respectively 3 to 10% glycerin and/or urea or carbamide are suitable based upon the amount of the emulsion.
  • thickener there can be employed, for example, polysaccharides, which are to be added in a concentration of 0.2 to 2%, preferably 0.5%, based upon the amount of the employed water. Natural polysaccharides as well as further sugar compounds and their derivatives are particularly suitable, since they do not react with the other components of the emulsion, they do not modify them and are thus chemically inert.
  • the polysaccharide agar agar is preferably employed.
  • Agar agar is a mixture of agarouse and agaropectin, which is obtained from red algae and has the advantage that it cannot be decomposed by most micro-organisms.
  • the polysaccharide carrageenan can be employed which occurs naturally in the cell wall of red algae and certain brown algae and has the same advantages as agar agar.
  • the emulsion comprises 2 to 10% extract from the white part of the birch bark, 20 to 30% avocado oil, 10 to 20% almond oil and 40 to 68% water.
  • the most preferred concentrations comprise 4% extract from the white part of the birch bark, 29.3% avocado oil, 14.7% almond oil and 52% water.
  • a further inventive emulsion contains 2 to 10% extract from the white part of the birch bark, 20 to 30% avocado oil, 10 to 20% almond oil, 5 to 10% moisturizing agent and 30 to 63% water.
  • the most preferred is the concentration of 4% extract from the white part of the birch bark, 29.3% avocado oil, 14.7% almond oil, 5% glycerin and/or 5% urea and 42 to 47% water.
  • the extract from the white part of the birch bark which is contained in all emulsions, comprises at least 80% betulin, at most 10% betulinic acid, at most 3% lupeol and at most 4% oleanolic acid.
  • the emulsion on the basis of its composition and its verifiable biocompatibility, is particularly suitable as a salve base for addition of all known fragrances, cosmetics and medicinal active agents.
  • a further atribute of the invention is a process for producing the inventive emulsion, wherein the process includes the following steps:
  • the dispersion and homogenization preferably occurs in a homogenizing mixer since the process can be carried in particularly simple manner in this way. Further, it is possible to prepare small amounts of emulsion for individual applications.
  • a moisturizing agent in particular glycerin and/or urea, or a thickener, in particular a polysaccharide.
  • a further attribute of the present invention is the use of the triterpenes for manufacture of a cosmetic, preferably in the form of a salve, a lotion, a cream, a gel, a jelly, a tincture, a shampoo, a powder and/or a cosmetic (compact) powder, in particular for application upon the skin, the face or scalp or scalp and/or for inhalation.
  • a cosmetic preferably in the form of a salve, a lotion, a cream, a gel, a jelly, a tincture, a shampoo, a powder and/or a cosmetic (compact) powder, in particular for application upon the skin, the face or scalp or scalp and/or for inhalation.
  • the triterpenes in particular the obtained betulin, are particularly suitable for skin and head care. It relaxes and smoothes skin, reduces the water loss and induces attractiveness and blush.
  • the cosmetic can be particularly employed for maintaining moisture of the skin and smoothing the skin as well as for reduction of age spots and can be employed in the case of dandruff or flaking skin.
  • a further advantage is the water insolubility of the triterpenes, so that skin which is exposed to water vigorously and for prolonged periods is particularly well protected.
  • the use as deodorant is particularly advantageous. Added to this is the minimization of transpiration on the basis of an effective closure of the sweat glands.
  • a further attribute of the present invention is the use of the triterpenes for production of a pharmaceutical or medicinal formulation, preferably in the form of a salve, a lotion, a cream, a gel, a jelly, a tincture, a shampoo, a powder and/or a cosmetic (compact) powder, in particular for application upon the skin, the face or scalp or scalp, and/or for inhalation, particularly preferably for treatment of dermatological conditions of the skin and/or the scalp, above all for neurodermitis, psoriasis, contact eczema, melanoderma, impetigo, pre-cancerous conditions of the skin as well as for inhalation during asthmatic attacks and/or for substitution in place of glucocorticoids.
  • the obtained triterpenes in particular the obtained betulin, is suitable for the therapeutic application on pre-cancerous skin.
  • inventive emulsion is so well suited for the above-mentioned applications because the extract from the white part of the birch bark includes no mutagenic characteristics. Topical toxicity tests were likewise carried out, wherefrom no sensitizing characteristics were discovered.
  • Diagnosis heavy, generalized psoriasis vulgaris
  • Treatment multiple daily application of the inventive emulsion as salve upon the afflicted skin areas
  • Treatment multiple daily application of the inventive emulsion as salve upon the afflicted skin areas
  • Diagnosis neurodermitis, hyperkeratotic, prematurely aged, chapped-shriveled skin
  • Treatment multiple daily applications of the inventive emulsion as salve upon the afflicted skin areas
  • Diagnosis neurodermitis, hyperkeratotic, prematurely aged, chapped-shriveled skin
  • Treatment multiple daily applications of the inventive emulsion as salve upon the afflicted skin areas
  • Diagnosis neurodermitis, hyperkeratotic, prematurely aged, chapped-shriveled skin
  • Treatment multiple daily applications of the inventive emulsion as salve upon the afflicted skin areas
  • Treatment multiple daily application of the inventive emulsion as salve upon the afflicted skin areas
  • Treatment multiple daily application of the inventive emulsion as salve upon the afflicted skin areas
  • Treatment multiple daily application of the inventive emulsion as salve upon the afflicted skin areas
  • Diagnosis dry, itching, easily infected scabbing eczema
  • Treatment multiple daily application of the inventive emulsion as salve upon the afflicted skin areas
  • the birch cork was delivered by:
  • Kaukas The “wood pulp company Kaukas” (UPM-Kymmene Lappeenranta, Finland). Kaukas separates the bark mechanically from the birch wood and the cork is also mechanically removed from the inner bark.
  • a first step the mechanically separated and the hand cut cork is analyzed regarding its identity.
  • the cork is microscopically examined, whereby multiple individual cork layers and lenticular cells, which are typical for birch, can be seen.
  • the extractable amount of triterpenes with n-hexane at 140 to 160° C. under increasing pressure is examined.
  • the extractable amount of triterpene with the main component betulin exceeded 10%, since such amounts occur only in the cork of birches with white bark.
  • the cork was ground in a cutting mill (produced by the company Retsch) and suctioned off out of the machine through a sieve with a pore size of 1 mm diameter. For the further extraction, only particles with a particle size ⁇ 1 mm were employed.
  • Betulin at least 80%
  • Betulinic acid at most 10%
  • the overview shows a typical gas chromatogram with values of 84 to 86% betulin, 4 to 5% betulinic acid, approximately 1% lupeol and approximately 1% oleanolic acid.
  • the amount of the solvent n-hexane remaining must be ⁇ 7,725 mg/kg extract, while a cream containing 4% birch cork extract may not contain more than 290 mg/kg n-hexane.
  • Typical values comprise 1,500 mg/kg n-hexane in dried extract, which corresponds to approximately 60 mg/kg in the birch cream.
  • Each charge was checked according to the European requirements with respect to the acid value ( ⁇ 5) and the peroxide number ( ⁇ 15) by means of a standardized process.
  • the content of birch cork extract was analyzed using GC. Further, an examination was made regarding microbes ( ⁇ 100/g); besides this, no pathological microbes may be contained.
  • the inventive formulation is set forth in Table 1 (Tab. 1). They were comprised of the following composition: TAB. 1 Composition of the Formulation Active Component in all Extract from Birch cork Formulations 40 ⁇ 4 mg/g Cream (4%) Formulation Ingredient in % Birch Cream A 29.3 avocado oil 14.7 Almond oil 52 Water Birch Cream G 29.3 avocado oil 14.7 Almond oil 5 Glycerin 47 Water Birch Cream H 29.3 avocado oil 14.7 Almond oil 5 Urea 47 Water
  • All three formations contained the same amount of the active component (birch cork extract) as well as avocado and almond oil. They differed essentially with respect to the component urea (only in birch cream H) as well as glycerin (only in birch cream G), birch cream A is free of these components.
  • the birch cream was centrifuged at 500 ⁇ g and was found to be stable therein.
  • the acute toxicity of the birch cork extract was determined by intra-peritoneal and subcutaneous administration to mice and rats.
  • the lethality was determined 14 days after the administration of an individual dose for determination of the average lethal dose LD 50 . At the same time the animals were observed in order to detect symptoms of toxicity. As such there were considered local and systemic intolerance reactions as well as changes in the body weight. The animals were sacrificed at the end of the experiment and examined microscopically. The acute toxicity test followed EC guidelines L 383 A: B1.
  • Chemicals are classified on the basis of their relative toxicity. They are characterized as toxic when the LD 50 valve us between 50 and 500 mg/kg body weight. With a LD 50 value of 5000 to 15000 mg/kg body weight there is the presumption of practically no toxicity.
  • the LD 50 value is >2000 mg/kg body weight, and is very likely also >5000 mg/kg body weight, since even with the high value of 2000 mg/kg body weight no toxic symptoms were observed.
  • the birch cork extract can be characterized as non-toxic.
  • Birch cork extract (charge-number: Bet. 009) was administered to experimental rats (Sprague-Dawley/Crl: CD® BR) by means of intraperitoneal injection over 14 days within the framework of a subacute toxicity test.
  • the test protocol is summarized in Table 4 (Tab. 4). TAB.
  • Dogs (Beagle), i.p.
  • a subacute toxicity was carried out over a period of two weeks with Beagles as dose-determining experiment, over 4 weeks as subchronic toxicity test.
  • the birch cork extract (Batch No.: Bet. 009) was administered intra-peritoneal with sesame oil as the carrier.
  • the results are summarized in Table 8 (Tab. 8).
  • TAB. 9 Subacute toxicity test in dogs (beagles), i.p. No effect: ⁇ 50 mg/kg body weight/day during the MTD time
  • Lethal dose 500 mg/kg body weight/day
  • Toxic indication during the fixed dose time (100, 300 mg/kg body weight/day)
  • Reduced body weight Reduced food uptake Change in hematopoetic and biochemical parameters Heavy stomach fur inflammation in 3 of 8 animals* )

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WO2005011717A1 (fr) * 2003-07-03 2005-02-10 Greenpharma S.A. Utilisation de l’acide betulinique ou d’un extrait vegetal titre en acide betulinique seul ou en association pour des applications cosmetiques, nutraceutiques, veterinaires et pharmaceutiques
WO2005123037A1 (de) * 2004-06-22 2005-12-29 Birken Gmbh Triterpenhaltiger oleogelbildner, triterpenhaltiges oleogel und verfahren zur herstellung eines triterpenhaltigen oleogels
US20060239957A1 (en) * 2001-10-03 2006-10-26 Sederma Sas Cosmetic and dermopharmaceutical compositions for skin prone to acne
WO2007121352A3 (en) * 2006-04-13 2008-08-28 Univ Minnesota Therapeutic triterpenoids
US20100179219A1 (en) * 2006-08-17 2010-07-15 Wala-Heilmittel Gmbh Plane Tree Cream, Method for the Production Thereof and Use
US20110212218A1 (en) * 2009-11-04 2011-09-01 Upm-Kymmene Corporation Method for modulating animal digestive tract microbiota and feed composition comprising bark extract
US9352041B2 (en) 2009-11-24 2016-05-31 Birken Ag Use of an oleogel containing triterpene for healing wounds
US9468590B2 (en) 2009-12-10 2016-10-18 Neubourg Skin Care Gmbh & Co. Kg Emulsifier-free, polymer-stabilized foam formulations
JP2016210695A (ja) * 2015-04-30 2016-12-15 ポーラ化成工業株式会社 皮膚外用剤
WO2018017576A1 (en) * 2016-07-18 2018-01-25 Rolf Daniels Betulin-containing water-in-oil foams and compositions thereof
US11083733B2 (en) * 2018-01-04 2021-08-10 Amryt Research Limited Betulin-containing birch bark extracts and their formulation
US11097981B2 (en) 2016-08-09 2021-08-24 A.L.M. Holding Company Sterol blends as an additive in asphalt binder
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US11427697B2 (en) 2017-07-26 2022-08-30 A.L.M. Holding Company Use of sterols from animal waste as an additive in asphalt binder
US11542668B2 (en) 2017-02-02 2023-01-03 Ergon Asphalt & Emulsions, Inc. Sterol additive in asphalt pavement
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Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060239957A1 (en) * 2001-10-03 2006-10-26 Sederma Sas Cosmetic and dermopharmaceutical compositions for skin prone to acne
US7182963B2 (en) 2001-10-03 2007-02-27 Sederma Cosmetic and dermopharmaceutical compositions for skin prone to acne
WO2005011717A1 (fr) * 2003-07-03 2005-02-10 Greenpharma S.A. Utilisation de l’acide betulinique ou d’un extrait vegetal titre en acide betulinique seul ou en association pour des applications cosmetiques, nutraceutiques, veterinaires et pharmaceutiques
US8536380B2 (en) * 2004-06-22 2013-09-17 Birken Gmbh Triterpene-containing oleogel-forming agent, triterpene-containing oleogel and method for producing a triterpene-containing oleogel
WO2005123037A1 (de) * 2004-06-22 2005-12-29 Birken Gmbh Triterpenhaltiger oleogelbildner, triterpenhaltiges oleogel und verfahren zur herstellung eines triterpenhaltigen oleogels
US20070299285A1 (en) * 2004-06-22 2007-12-27 Scheffler Armin Triterpene-Containing Oleogel-Forming Agent, Triterpene-Containing Oleogel and Method for Producing a Triterpene-Containing Oleogel
US8828444B2 (en) * 2004-06-22 2014-09-09 Birken Ag Triterpene-containing oleogel-forming agent, triterpene-containing oleogel and method for producing a triterpene-containing oleogel
AU2005253732B2 (en) * 2004-06-22 2009-07-16 Birken Gmbh Triterpene-containing oleogel-forming agent, triterpene-containing oleogel and method for producing a triterpene-containing oleogel
AU2005253732C1 (en) * 2004-06-22 2010-01-21 Birken Gmbh Triterpene-containing oleogel-forming agent, triterpene-containing oleogel and method for producing a triterpene-containing oleogel
US20090136566A1 (en) * 2006-04-13 2009-05-28 Regents Of The University Of Minnesota Therapeutic triterpenoids
WO2007121352A3 (en) * 2006-04-13 2008-08-28 Univ Minnesota Therapeutic triterpenoids
US20100179219A1 (en) * 2006-08-17 2010-07-15 Wala-Heilmittel Gmbh Plane Tree Cream, Method for the Production Thereof and Use
US20110212218A1 (en) * 2009-11-04 2011-09-01 Upm-Kymmene Corporation Method for modulating animal digestive tract microbiota and feed composition comprising bark extract
US9827214B2 (en) 2009-11-24 2017-11-28 Amryt Research Limited Use of an oleogel containing triterpene for healing wounds
US9352041B2 (en) 2009-11-24 2016-05-31 Birken Ag Use of an oleogel containing triterpene for healing wounds
US9468590B2 (en) 2009-12-10 2016-10-18 Neubourg Skin Care Gmbh & Co. Kg Emulsifier-free, polymer-stabilized foam formulations
JP2016210695A (ja) * 2015-04-30 2016-12-15 ポーラ化成工業株式会社 皮膚外用剤
US11912874B2 (en) 2016-06-10 2024-02-27 A.L.M. Holding Company Crude sterol as an additive in asphalt binder
US11168214B2 (en) 2016-06-10 2021-11-09 A.L.M. Holding Company Method for identifying the extent of aging in an asphalt
US11760882B2 (en) 2016-06-10 2023-09-19 A.L.M. Holding Company Method for identifying the extent of aging in an asphalt
WO2018017576A1 (en) * 2016-07-18 2018-01-25 Rolf Daniels Betulin-containing water-in-oil foams and compositions thereof
US11667570B2 (en) 2016-08-09 2023-06-06 A.L.M. Holding Company Sterol blends as an additive in asphalt binder
US11097981B2 (en) 2016-08-09 2021-08-24 A.L.M. Holding Company Sterol blends as an additive in asphalt binder
US11542668B2 (en) 2017-02-02 2023-01-03 Ergon Asphalt & Emulsions, Inc. Sterol additive in asphalt pavement
US11427697B2 (en) 2017-07-26 2022-08-30 A.L.M. Holding Company Use of sterols from animal waste as an additive in asphalt binder
US11718756B2 (en) 2017-10-20 2023-08-08 A.L.M. Holding Company Asphalt emulsion surface treatment containing sterol
US11266660B2 (en) 2018-01-04 2022-03-08 Amryt Research Limited Betulin-containing birch bark extracts and their formulation
US11826374B2 (en) 2018-01-04 2023-11-28 Amryt Research Limited Betulin-containing birch bark extracts and their formulation
US11083733B2 (en) * 2018-01-04 2021-08-10 Amryt Research Limited Betulin-containing birch bark extracts and their formulation

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EE200200552A (et) 2004-04-15
EP1267900B1 (de) 2004-04-21
PT1267900E (pt) 2004-08-31
EA013736B1 (ru) 2010-06-30
EA200501002A1 (ru) 2006-02-24
CN100518748C (zh) 2009-07-29
DE50102055D1 (de) 2004-05-27
AU2001242517A1 (en) 2001-10-08
EP1267900A1 (de) 2003-01-02
NO20024591D0 (no) 2002-09-25
PL356723A1 (en) 2004-06-28
WO2001072315A9 (de) 2002-10-24
EA200200983A1 (ru) 2003-04-24
CA2404147A1 (en) 2001-10-04
WO2001072315A1 (de) 2001-10-04
CN1426305A (zh) 2003-06-25
EE04931B1 (et) 2007-12-17
DK1267900T3 (da) 2004-08-02
US7482383B2 (en) 2009-01-27
NO20024591L (no) 2002-11-11
TR200401400T4 (tr) 2004-07-21
CA2404147C (en) 2016-07-12
PL202948B1 (pl) 2009-08-31
US20070231418A1 (en) 2007-10-04
NO329922B1 (no) 2011-01-24

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