A method of processing betulin and its derivatives

 

(57) Abstract:

The invention relates to a method of processing betulin and its derivatives, for example Betulinol acid, betulin diacetate, and can be used in cosmetic, pharmaceutical and chemical, in particular in the manufacture of varnishes and paints industries. Processing of betulin and its derivatives carry out a preliminary treatment with emollients from the group of vegetable oils and alkyldiphenylamine silicones when the mass ratio of betulin or its derivative : emollients 1 : 0.6 to 1.5, followed by mixing with an organic solvent and carrying out the stage of emulsification and homogenization known methods. 3 table.

The invention relates to a method of processing betulin and its derivatives, for example Betulinol acid, betulin diacetate, and can be used in cosmetic, pharmaceutical and chemical, in particular the manufacture of varnishes and paints industries.

There is a method of processing a neutral compounds [RU, Pat. N 2080326, C 07 J 9/00, C 11 D 13/04 was investigated, 1997], which contains betulin and other biologically active substances by extraction with an organic solvent, namely, that neutral prophetic is a thief with subsequent crystallization, filtering and selection of betulin with subsequent selection of the "turns" from the filtrate sterols, polyprenols and squalene.

The disadvantage of this method is the use of water-alkaline solution, the presence of which is not allowed in cosmetics and pharmaceuticals, as well as use as a hydrocarbon solvent extraction of gasoline, petroleum ether, nefras etc.

A known method of extraction of betulin [RU Pat. N 2138508 C 07 J 53/00, 63/00, 1999] bark extraction working unitsperem with subsequent treatment with alkali, separating the resulting precipitate and the selection of the extract Betulinol known methods.

The disadvantage of this method is the use of alkali to obtain Betulinol. There is a method of obtaining betulin [RU Pat. N 2074867, C 08 H 5/04, C 07 J 53/00, 63/00, 1997] from the pre-treated birch bark extraction in an aqueous alcoholic alkaline environment, and as alcohol use methanol, ethanol, isopropanol.

However, the extract betulin obtained by a known method, is alkaline, and foods that have an alkaline reaction, it is unacceptable to use in cosmetics and pharmaceuticals, as they negatively deistviya emulsion of a solution of type oil-in-water, which can be easily introduced into any other emulsion, such as cosmetic, pharmaceutical, paint and varnish.

This task is solved by the fact that according to the proposed method of processing betulin and its derivatives, including treatment with an organic solvent, dry betulin or derivatives of betulin pre-treated with emollients - vegetable oil or alkyl-modified silicone. As emollient choose a substance from the group sunflower oil, soybean oil, olive oil, palm oil fraction with a melting point below 20 - 25oC, alkyl-modified silicones, such as acidisation with a melting point of approximately 20oC or stearamidomethyl, and betulin and emollient used in their mass ratio of 1 : 0,8-1,5; Betulinol acid and emollients - 1 : 0,8-1,5, betulin diacetate - 1 : 0,6 : 1,5.

The proposed method meets the criteria of "novelty" and "inventive step", because it provides the company with a high yield, and as a neutral emulsion of a solution of type oil-in-water, which can be directly used in the cosmetic, pharmaceutical, paint and other emulsify or slightly yellowish powder with an interval of melting point 251 - 252oC.

The method is carried out as follows. The reactor is placed 1 weight part of the dry betulin, add emollient selected from the specified group in the amount of 0.8 to 1.5 weight parts, mix, then add 2 weight parts of ethyl alcohol, again mix, then add 4 weight parts of distilled water and keep stirring until a homogeneous mass (stage emulsification). After completion of the emulsification, the emulsion is homogenized to achieve a homogeneous finely dispersed emulsion.

The emulsion obtained is ready for use in cosmetics and other products. The introduction of emollients less of 0.8 weight parts does not ensure complete wetting of betulin, resulting in an unstable emulsion mixed with solid particles. Introduction it is greater than 1.5 weight parts degrades the quality of the subsequently produced emulsion.

All examples are implemented by the given method and used by different emollients and its quantity.

The results are given in table. 1.

Examples 7 to 10.

For processing used Betulinol acid which is a white or slightly yellowish poll the reactor is placed 1 weight part of the dry Betulinol acid, add emollient selected from the specified group number of 0.8 to 1.5 weight parts, mix, then add 2 weight parts of ethyl alcohol, again mix, then add 4 weight parts of distilled water and keep stirring until a homogeneous mass (stage emulsification). After completion of the emulsification, the emulsion is homogenized to achieve a homogeneous finely dispersed emulsion.

The introduction of emollients less than 0.8 weight parts does not ensure full wetting Betulinol acid. Introduction it is greater than 1.5 weight parts degrades the quality of the subsequently produced emulsion. All examples are carried out in this procedure and used differ amuletum and its quantity.

The results are given in table. 2.

Examples 11 to 14.

For processing used betulin diacetate, which is a white crystalline powder with an interval of melting point 223 - 224oC. the Method is as follows. The reactor is placed 1 weight part of betulin diacetate, add emollient selected from the specified group in the amount of 0.6 to 1.5 weight parts, mix, then add 2 weight parts of ethyl s homogeneous mass (stage emulsification). After completion of the emulsification, the emulsion is homogenized to achieve a homogeneous finely dispersed emulsion. The introduction of emollients less than 0.6 and more than 1.5 weight parts affects the amount received in the future of the emulsion. All examples are implemented by the given method and used by different emollients and its quantity.

The results are given in table. 3.

The resulting emulsion is a homogeneous mass that do not contain permanent impurities (determination was carried out according to GOST 291880).

The definition of colloidal stability and thermal stability was carried out according to GOST 291883.

The use of the invention allows to obtain an emulsion of natural betulin and its derivatives, suitable for further use in various cosmetic, pharmaceutical tools that will significantly improve the quality of creams, allowing you to reduce the content of synthetic emulsifiers, to increase the biological activity of the cream.

A method of processing betulin and its derivatives, characterized in that the company or its derivative is treated with emollients, selected from the group of vegetable oils or alkyldiphenylamine silicones, when the mass is

 

Same patents:

The invention relates to new biologically active chemical compound, specifically to 3,28-di-O-nicotinate betulin (1), formula

< / BR>
showing hepatoprotective and anti-HIV activity

The invention relates to the synthesis of allobetulin (19, 28-epoxy-oleana-3-Ola) isomerization of Betulinol(loop-20(29)-EN-3, 28-diol) in the presence of catalysts

The invention relates to 14,17-C2-bridged steroids of formula I, where R3- O, R6- Hor-(C1-C4)-alkyl, where R6and R7together form an additional bond; R7-or-(C1-C4)-alkyl, where R6and R6both H, or R9and R10each H or together form a bond, R11and R12each H or together form a bond, R13- CH3or2H5; R15- H or C1-C3-alkyl; R16and R16independently H, (C1-C3)-alkyl or C1-C4alkenyl or together form a (C1-C3-alkyliden; R15and R16together form a cyclewhere n = 1, and h - O and R16- N- H, (C1-C3)-alkyl,- H, (C1-C3)-alkyl,- H, (C1-C3)-alkyl or HE; except 14,17-ethano-19-norpregna-4-ene-3,20-dione

The invention relates to substituted derivatives of 19-norpregnane, methods of producing these compounds and pharmaceutical compositions containing them

Steroid compound // 2160279
The invention relates to extrenely steroids that are associated with neuroepithelial cells in the vomeronasal organ of the human body

The invention relates to organic synthesis

The invention relates to the field of chemical processing of birch bark (outer layer of birch bark)

The invention relates to extraction of valuable chemicals from waste timber, namely the allocation method betulin formula I from birch bark

FIELD: organic chemistry, steroids, pharmacy.

SUBSTANCE: invention describes unsaturated 14,15-cyclopropanoandrostanes of the general formula (I):

wherein R1 means hydrogen atom (H), hydroxy-group (OH); R2 means hydroxy-group (OH), hydrogen atom (H); R3 means hydrogen atom (H), (C1-C10)-alkyl at α- or β-position; R4 means halogen atom (F, Cl, Br) or pseudohalogen group (azide, rhodanide), hydroxy-group (OH), perfluoroalkyl; R5 means (C1-C4)-alkyl; if double bond is at 1,2-position then R4 can mean hydrogen atom (H). Also, invention relates to a method for preparing these compounds and pharmaceutical compositions containing these compounds. Compounds of the formula (I) are compounds eliciting gestagenic and/or androgenic effect.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

11 cl, 1 tbl, 9 ex

FIELD: chemical technology, natural materials, medicine, pharmacy.

SUBSTANCE: invention relates to the improved method for preparing betulin from betulinic acid that can be used in preparing anti-tumor and anti-HIV medicinal preparations. Method for preparing betulinic acid involves oxidation of betulin with chrome (VI) oxide in acetic acid to betulonic acid and reduction with sodium boron hydride to betulinic acid. Betulonic acid sodium salt is reduced to betulinic acid and reduction reaction is carried out at room temperature at the concentration of sodium boron hydride 1.0-6.0 wt.-%. Invention provides simplifying method for preparing betulinic acid, reducing its cost and enhancing ecological safety of the process of it producing.

EFFECT: improved preparing method.

1 cl, 4 ex

FIELD: organic chemistry, steroids, medicine, pharmacy.

SUBSTANCE: invention relates to steroid compounds of the formula (1)

wherein --- means optional double bonds; R6 means hydrogen atom (H), =CH, -CH3 or -CH2-CH3; R7 means hydrogen atom (H), (C1-C4)-alkyl, (C2-C5)-alkenyl, or (C2-C5)-alkynyl; R11 means hydrogen atom (H), (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkylidene; E means 5-7-memberd ring formed with 16 and 17 carbon atoms at α,cis-position relatively to steroid structure and comprising possibly up to two double bonds. Compounds can be used in therapy and in methods for selective modification of activity of estrogen receptors.

EFFECT: improved method for modifying, valuable medicinal properties of compounds.

10 cl, 1 sch, 1 tbl, 1 ex

FIELD: chemical technology.

SUBSTANCE: invention relates to methods for preparing oleanolic acid used as a standard sample (comparison samples) in carrying out standardization of medicinal vegetable raw and phytopreparations comprising triterpene saponins - derivatives of oleanolic acid. For preparing oleanolic acid method involves sum of saponins extracted by alkaline extraction from sugar or table beet root crops followed by reprecipitation in acid medium and extraction of precipitate with ethanol, chloroform. Method provides preparing oleanolic acid of high purity degree from inexpensive and available raw.

EFFECT: improved preparing method.

2 cl, 3 ex

FIELD: organic chemistry, steroids, chemical technology.

SUBSTANCE: invention describes a method for preparing 3-keto-7α-alkoxycarbonyl-substituted ▵4,5-steroid of the formula (I): wherein is taken among or R3 means hydrogen atom (H), lower alkyl, lower alkoxy-group or cyano-group (CN); R21 means hydrogen atom (H) or alkyl; R26 means (C1-C4)-alkyl; R8 and R9 form in common heterocyclic ring system. Method involves interaction of an alkylating agent with 4,5-dihydro-5,7-lactone steroid of the formula (II): wherein R18 means (C1-C4)-alkyl or R18O-group taken in common form O,O-oxyalkylene bridge or keto-group and R3, R8 and R9 have above given values in the presence of a base. Compounds of the formula (I) are used as intermediate compounds in improved methods for synthesis of epoxymexerone.

EFFECT: improved preparing method.

56 cl, 42 tbl, 30 sch, 5 dwg, 89 ex

FIELD: medicine; pharmaceutical industry; perfumery-cosmetic industry; methods production of betulin.

SUBSTANCE: the invention is pertaining to the method of extraction of betulin from the wastes products of wood-processing, in particular, a birch bark processing and may be used in medicine, pharmaceutical and perfumery-cosmetic industries. The method provides for activation of a birch bark by the shock-acoustic impulses, an alkaline hydrolysis and an extraction of betulin by an alcohol. The operations are conducted simultaneously. The technical result of the invention is simplification of the method of the process, reduction of its duration and power input.

EFFECT: the invention ensures simplification of the method of the process, reduction of its duration and power input.

1 cl, 2 ex

FIELD: natural compounds, chemical technology.

SUBSTANCE: invention relates to the improved method for preparing biologically active substances from products of chemical processing vegetable biomass, in particular, to a method for preparing betulinic acid from betuline. Method is carried out by oxidation of betuline with chrome anhydride in acetic acid to betulonic acid, and reduction of betulonic acid with sodium boron hydride is carried out in diethyl ether solution being without its preliminary isolation. Invention provides enhanced yield, simplifying technology, decrease of the process time and decreasing set of solvents used.

EFFECT: improved preparing method.

1 cl, 1 ex

FIELD: chemistry of natural compounds, chemical technology, pharmaceutical industry.

SUBSTANCE: invention relates to the improved method for preparing betulinic acid from betulonic acid. Method is carried out by reduction of betulonic acid with sodium boron hydride in water. Method provides simplifying the process, declining cost of the process for preparing betulinic acid and enhancing ecological safety of the process. Invention can be used in producing antitumor and anti-HIV medicinal preparations.

EFFECT: improved preparing method.

1 cl, 2 ex

FIELD: fine organic synthesis, in particular production of triterpene compounds, betulin, useful in pharmaceutical and cosmetic industry.

SUBSTANCE: betulin is isolated from birch bark by extraction with neutral organic solvents, namely dioxan aqueous solution containing 0-20 mass % of water.

EFFECT: accelerated extraction process, increased yield of target product, decreased concentration of ester contaminants, and simplified betulin purification.

1 cl, 7 ex, 1 tbl

FIELD: natural substances technology.

SUBSTANCE: method of preparing extractive substances from ground birch bark comprises extraction and filtration of precipitated extract. Extraction is effected with extractant condensate sprinkling ground birch bark bed in presence of ascending vapors of the same extractant. Extractant is two-component mixture of water and low-boiling solvent having boiling point below 100°C. Product is isolated by bringing extractant condensate containing dissolved extract with contents of receiver. Once extraction is completed, solvent is removed with live steam.

EFFECT: reduced consumption of extractant, increased degree of extractant regeneration, simplified isolation of product, and reduced fire and explosion risk.

1 tbl, 2 ex

Up!