Methods of obtaining esters of stanlow/sterols

 

(57) Abstract:

The invention relates to an improved method of direct esterification of Stanlow/sterols interaction of stanol/sterols and acid taken in stoichiometric ratio, in the presence of a sufficient amount of catalyst, which can be acidic or basic, and in the presence of a sufficient amount of decolorizing agent, preferably activated carbon. The method is suitable for large-scale production of esters in high yield and eliminates the use of organic solvents or mineral acids. 3 S. and 17 C.p. f-crystals.

The technical field to which the invention relates

This invention relates to the production of individual esters of sterols and stanilov through highly efficient catalytic method in the presence of the agent decontamination color.

Background of invention

It is shown that the addition of the food rations of plant sterols, such as sitosterol, reduces cholesterol level in serum. Sterols reduce cholesterol due to malabsorption in the intestines of dietary cholesterol through Vitesse which is more effective in reducing the absorption of cholesterol in the intestine. Sitostanol not actually absorbed, so that after the consumption of it does not make any contribution to the concentration of Sterol in serum in vivo. Unfortunately, typical sterols and stanol insoluble in the micellar phase of the digestive tract and only sparingly soluble in oils and/or fats or water. Therefore, themselves free sterols or stanol are not optimal for use in a typical pharmaceutical or dietary dosage forms as a means to reduce cholesterol.

In U.S. patent No. 5502045 describes the transesterification of Stanlow ether fatty acids from edible oils with the formation of a wax-like mixture of esters of sterols with improved characteristics solubility in fats. Specifically, this patent describes the interesterification reaction of sitostanol fatty acids of methyl esters of edible oil, such as rapeseed oil, namely with the help of the interesterification reaction with a base as catalyst. This process is widely used in the food industry.

However, from a pharmaceutical point of view, the ways interesterification, resembles, have some obvious shortcomings. First of all, SOS is from, present in the edible oil used in the reaction. In addition, a by-product of this reaction is methanol would have to be carefully removed, and the use of methyl esters requires them to be used in large excess, which makes it difficult to recycle.

In German patent 2035069 describes a different approach - esterification of esters of Sterol fatty acids by way of non-food categories. In particular, as the reagent is thionyl chloride, the reaction produces Hcl released in the form of a gaseous by-product.

Such methods are not suitable for materials food category, and they are generally undesirable.

In the Japan patent 76-11113 describes the esterification of sterols or related vitamins without catalyst with obtaining esters of higher fatty acids.

However, this method uses a considerable molar excess of fatty acid, at least from 25% to 50%, which, in turn, requires the use of alkali cleaning process for the extraction of the obtained esters. Surplus fatty acids against stoichiometry and allocation methods result in products that have lost their color.

From the pharmaceutical point of view, there are necessa using mass food category. Individual compounds are more desirable than the mixture, for three main reasons: 1) it is possible to better control the composition and performance; 2) more feasible studies of the structure and activity; and 3) you can control the physico-chemical and chemical properties. These advantages of individual esters stanilov and sterols in the future will be discussed in more detail.

In addition, there is a need to esters of sterols and stanilov food categories that are light, when cooking with natural food color of attractive food. Also essential ways that reduce production losses and cost of equipment.

The invention

The present invention relates to a method of direct esterification of Stanlow or sterols using catalysts in the presence of the agent, decontamination color, with the formation of individual esters of Stanlow and sterols. The catalyst may be either a weak acid in the classical sense, or a Lewis acid, or a traditional alkaline substances. In the method proposed synthesis, which can be implemented in large-scale production of the esters stanol embodiment of the invention, free from organic solvents or mineral acids, and produce a limited number of products. Ultimately, this method is implemented a streamlined process that provides an opportunity to develop technology for individual esters of Stanlow and sterols with different physical and biological properties.

Detailed description of the invention

In the present invention proposes a direct etherification of Stanlow and sterols through interaction stanol or Sterol and fatty acids using either acidic or basic catalyst. The most preferred starting material is sitostanol is made from industrial-sitosterol through hydrogenation reactions and commercially available from various sources, including from Raisio Corporation.

Acid, which include the associated salt involved in the interaction of the present invention, contain from 4 to 24 carbon atoms. Such acids include saturated acids, but preferred are unsaturated, including polyunsaturated acids.

Saturated fatty acids involved in the interaction really subjecttitle n is from about 12 to about 20. The term "fatty acid" is well known and accepted by experts in the field of technology, see, for example, Hawley's Condensed Chemical Dictionary, Eleven edition. The term includes ourselves acid and salts of these acids. To fatty acids include saturated acids such as stearic, butyric, lauric, palmitic and the like acids. In the present invention it is also possible to use unsaturated fatty acids, including polyunsaturated fatty acids. Suitable unsaturated fatty acids are oleic, linoleic, linolenic, docosahexanoic acid, linoleic acid with conjugated double bonds and the like acids. As described in U.S. patent 5554646, column 1, lines 44-48, linoleic acid with conjugated double bonds is a 9,11-octadecadienoic acid, 10,12-OCTA DECA diene acid and mixtures thereof. The present invention includes both linear and branched acid, preferably the acid with a linear chain structure.

In the present invention esters of sterols and stanilov have a General formula I

where it is assumed that R1includes aliphatic linear or branched carbon chain length of From about2includes aliphatic linear or branched carbon chain in the interval WITH a3-C15preferably - C6-C12and most preferably a group WITH a9. Preferably, R2is selected from groups (C1-C12)-alkyl, (C1-C8)-alkoxy, (C2-C8)-alkenyl, (C2-C8)-quinil, (C3-C8-cycloalkyl, halogen-(C2-C8)-alkenyl, halogen-(C2-C8)-quinil, where we mean that the halogen includes chlorine, fluorine, bromine, iodine, etc., the Alkyl group includes both the linear and branched chains of carbon atoms. Typical alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, hexyl, heptyl and the like groups. Alkyl groups can be halogenated with one, two, three or more halogen atoms.

The terms "alkenyl" and "quinil" includes branched and linear hydrocarbons containing at least one unsaturated bond.

Unsaturation at the atom WITH5gives the corresponding ester of a Sterol. Any stanol or Sterol having functional hidrocloro and sterols, you can atrificial according to the present invention.

Assume that R2has the same values that you set above.

To stanols which are capable of esterification according to the present invention, include, but are not limited to, sitostanol (see formula III), as well as other related compounds, including cholesterol, ergosterol, brassicasterol, avenasterol, alpha amyrin, collateral, lupeol and similar compounds.

For example, this method is also suitable for such sterols, such as sitosterol (unsaturated atom5as shown above (see formula III)).

The molar ratio of initial substances for the esterification reaction, namely stanol or Sterol and fatty acids, are provided at the stoichiometric level. In a highly preferred variant of embodiment of the invention the fatty acid is present in 5-10% excess to react whole stanol. Any excess of unreacted acid can be easily removed by treatment of the reaction product.

In the present invention can use any suitable catalyst. The catalyst may be a weak key, described in U.S. patent 5892068 included in the present description by reference. Suitable acid catalysts include toluensulfonate acid, methanesulfonate acid, sodium dihydrophosphate, sodium bisulfate, although mineral acids are not preferred. Suitable catalysts that can act as a Lewis acid, include iron chloride, iron oxide(3), magnesium oxide, manganese oxide, manganese chloride, Nickel chloride, tin oxide, tin chloride and zinc oxide and zinc chloride. Some substances the main character also act as catalysts for this reaction, such as sodium hydroxide. The amount of catalyst is usually sufficient, if it is 1 mol.% in relation to the number of reagents. It is implied that used here as the catalysts of the Lewis acid are compounds that are potential acceptors pairs of electrons. The amount of catalyst can be increased or decreased to provide the desired reaction rate, however, if the catalyst is too much, the result can be more intense than desirable, adverse reaction and its products. To another suitable as catalysts for the Lewis may act as a catalyst, moreover, the preferred catalyst is zinc oxide. The catalyst may be in the form of solids, liquids or gas.

One of the most effective aspects of the present invention is that the reaction is carried out in undiluted environment, when the reaction mixture do not add any solvent, as the acid, in a preferred variant embodiment of the invention the fatty acid in the molten state, acts as a reactant and as a solvent.

Especially favorable is the implementation of the net reactions in vacuum, to remove water from the reaction mixture, which reaction takes place completely and increases the yield of the desired ester. As the water is not soluble in the product, to complete the reaction requires much less fatty acids.

The reaction temperature is from about 75 to about S. The preferred range is from about 100 to about 220C, and the most preferred is from about 140 to 180C. The reaction time may vary within wide limits, but for best results with the aim of saving the reaction should be carried out to completion. Usually requires a reaction time of over 12 hours way high output which is the reaction product of an ether. The method according to the present invention provides access to more than 90%, and preferably over 95%.

The interaction of the present invention is soft enough to get esters, which cannot be synthesized using methods previously described in the art. In particular, the present invention proposes a method of producing esters which are reaction products of DHA (CIS-4,7,10,13,16,19-docosahexaenoic acid) and CLA (octadecadienoic acid) with the above Sterol or stenolol. These reaction products are of particular interest, as it is reported that as DHA, and CLA have properties to reduce cholesterol. Therefore, a compound that contains a combination of stanol or Sterol with forming an ester functional group, which on hydrolysis gives another substance that restricts the action of cholesterol can be very useful. The combination of these functions would be favorable, since it is reported that DHA and CLA reduce Helena Sterol in the body through mechanisms other than products of type Sterol and stanol.

Below is the General formula of the ester products of interaction between CLA and Sterol or stanol, i.e. octadecadienoate-isomer.

More preferred octadecadienoate-sitosterol

Similarly, the following is the General formula of the ester products of interaction between DHA and Sterol or stanol, i.e. docosahexaenoate Sterol/stanol

and preferable

docosahexaenoate-sitosterol and

docosahexaenoate-sitostanol.

The present invention also proposes a method of reducing cholesterol in serum by introducing an effective amount of the ester of CLA and DHA to reduce cholesterol in serum. In a typical case, this amount is from about 1 to about 20 g/day, preferably from about 3 to about 15, and most preferably from about 6 to about 9 grams per day.

To highlight the obtained esters you can use the following three methods of selection.

Method A. To extract the ether stanol you can use the selection by extraction with water/organic solvent. Typical organic solvents are dichloromethane, chloroform or toluene. Uses a typical water/organic processing, when the air is extracted to the organic is based temperature and then add CH2Cl2. Then the solution is washed several times with aqueous solution Panso3. Salts of fatty acids are redistributed in the aqueous phase and can be removed easily. The remaining organic phase containing the selected ether, and then dried over anhydrous Na2SO4and discolor activated carbon. When extraction using light, chlorine-free organic solvents (i.e., hexane), observed the formation of an undivided emulsion. Pure ether extract in the form of white solids or oils after removal of the solvent on a rotary evaporator and subsequent cooling.

Method C. In preferred methods of allocation used in the case where the reaction is catalyzed by a weak acid, the esters dissolved in water (10-15% relative to the reaction mixture) is added to the amount (in moles) of sodium hydroxide, at least equal to the amount of acid, but not more than 10% molar excess. After careful mixing water and soap is poured. Then the substance discolor and deodorize using procedures common to the industry of edible oils. As most of the excess fatty acids after washing will ostabat the LASS="ptx2">

Way S. In accordance with the preferred allocation method used in the case of the use of basic catalysts and certain Lewis acids, obtained by the reaction of the ether distinguish using only water. The crude reaction mixture is washed with 10% water, which give separate within 1-2 hours and then drain. The obtained ether to remove paint and traces present soap then discolor bleaching clay for edible oils or bleaching agents based on silica and deodorize to remove excess fatty acids that are ready for re-use without additional processing.

Although all three methods give the esters, with the same purity, the best output when extracting (>96%) is obtained according to method C. This method is also highly applicable for large scale synthesis because it gives a high-purity product without the use of dangerous solvents non-food categories. In this way also to a lesser extent, interact with the original substances, which improves the yield and reduces product loss. The method In the preferred method, as it also provides increased output compared to A. If both b and C Leggewie the invention provides a number of advantages over previously described methods. The present invention provides a method for the synthesis of practically pure individual esters of stanol and not mixtures of esters of stanol. Have in mind that when used herein, the expression “almost pure individual” means that the reaction product, i.e., the desired ester is a very significant part of the reaction product. In a typical case, the desired ester is the reaction product of at least 90 wt.%, preferably contained in an amount of at least about 98 wt.%, and if the reaction has ended completely in the amount of at least 99 wt.%. The present invention provides the ability to get essentially the only broadcast stanol (Sterol) content in the reaction product is less than 0.2 wt.% other esters. The previously described methods interesterification give a mixture of esters of Stanlow. For example, the previously described methods give a mixture of esters of Stanlow, often with a wide range of present esters of stanol (for example, a mixture of 4 esters in the ratio of 30, 30, 20, 20 wt.%). Also, for comparison, in the previously described methods of direct esterification use of dangerous toxic chemicals.

Such a product in the form of individual esters stenolol or sterols has several important advantages over mixtures of esters solee specific performance (i.e., the melting temperature, relative density, purity, structural type). This is because the properties of individual compounds can be controlled with greater precision than mixtures. Therefore, good performance and the quality of the individual esters easier to guarantee in comparison with mixtures of esters.

In addition, since the present invention provides the synthesis of individual esters of stanol or Sterol, you can set the relationship between structure and activity when changing the chain length fatty acids. To elucidate the relationship between structure and activity, which is critical for the conscious development of medicines, is feasible only with the study of individual compounds.

You can adjust the macroscopic physical and physiological properties of Sterol ester or stanol, since these properties depend on the used fatty acids. For example, the esterification of unsaturated fatty acids (i.e., oleic acid) can lead to low-melting solids or even liquid reaction products, while the saturated analogues (stearic acid) tend to form a more engineering high-melting solids the extent unexpected.

The present invention permits a choice of ether thus, in order to find desirable physical properties. Solid engineering substance is desirable in the manufacture of compressed tablets or activate the air stanol in baking products. Butter-like esters stenolol or sterols advantageously used in the production of soft gelatinising dosage forms or for inclusion in a dressing for salad or yogurt.

Another advantage of the present invention is the ability to add an appropriate amount of decontamination coloring agent during the reaction. In a typical case, the amount of deactivating the coloring agent is from about 0.05% to about 1 wt.% in relation to the total reaction mass; preferably from about 0.15 to about 0.5 percent; and most preferably from about 0.25 to about to 0.35 wt.%. Suitable agents, decontamination color, are carbon, coal and gas soot; bleaching clay for edible oils or bleach on the basis of silicon dioxide, such as from Trysil Grace Chemical, of which preferred is carbon or activated charcoal. Agent, decontamination color, prevents discoloration of the product is with stenolol or Sterol and acid.

The product obtained according to the present invention, is white, not containing odorous substances and other volatile substances the product with a mild flavor. Obtained as the reaction product of the ester stanol or Sterol ester has a color number on Gardner less than 8, typically less than about 6, preferably less than about 4, and most preferably less than approximately 3 on a scale of color Gardner. Dial color Gardner's well-known specialists in this field of technology. The reaction product is formed into a briquette, and the color of the block is compared with samples with a predefined color. Previously developed methods give a product with a higher color numbers. For example, the esters of Stanlow received in accordance with U.S. patent 5892068 had colour on Gardner from about 9 to about 12. Using the method described in Japan patent 76-11113, the products could have colored numbers on Gardner from about 10 to about 12.

The reaction product can be dissolved in oil and add to any food product that contains an oil component.

Another advantage of the present invention is to eliminate the need for expensive Soaps VM product. This improves the output, reducing loss and speeding up the conversion in the reactor. Another advantage of the reaction is the ease of recycling of the excess fatty acids without additional processing.

Another advantage of the present invention to provide a less colored product. Another advantage of the present invention is the use of a small excess of fatty acids. In other developments require large excess source of fatty acids, in order to bring the reaction to completion (often a molar relationship of fatty acids to stanol/Sterol are two to one). This makes clean-up, or treatment after the reaction, difficult and expensive. The use of a large excess reduces the amount of product obtained in this reactor, which increases capital costs and labor costs per pound of product.

Another advantage of the present invention is less reaction time, provide catalyzed reactions, compared with acatalasemia reactions when they are at the same temperature. In addition to reducing the time of reaction, the resulting product is also a good color. For example, for recataloging conditions, such as the amount of load and geometry of the reactor, can be carried out at significantly lower temperatures in C, and reaction time to completion is 13 hours. Usually the reaction time according to the present invention ranges from about 8 to about 15 hours, preferably from 10 to about 14, and most preferably from about 12 to about 13 hours.

It is implied that the term "acid" is used here to describe the acid that is used as the reagent comprises fatty acids, saturated and unsaturated, including polyunsaturated acids, as specified in this description. The following examples are intended to further explain the invention described in the claims, but the invention is not limited to the following examples.

Examples

Esters of Stanlow and fatty acids according to the invention receive through the esterification reaction catalyzed by the acid, as follows: stanol (10 mmol), fatty acid (12 mmol) and sodium bisulfate (0.12 mmol) are mixed undiluted in vacuum for 16 hours at 150C. The resulting esters stanilov emit from the use or the method described above as method A (case, when on the way And get glassy products, they can be turned into solid engineering of matter by cooling below 0C. Analysis by gas chromatography of the crude reaction product shows that the reactions take place more than 95%. The final treatment is carried out according to methods a or b, described above.

The results of the analysis of five representative esters of Stanlow described below. Also the results of analysis for air cholestanol as an additional sample.

Example 1

-Sitosterolemia get through interaction-sitostanol and stearic acid. As the catalyst used NaHSO4and stigmastanol allocate using the method As described above.

The results of the analysis of the selected stigmastadiene the following:

1H NMR (Dl3): (4,60 (quintet, 1H), 2,19 (t, 8, 2H), 1,88, (d, 12, 1H); IR (cm-1, CVG): 1739 (C=0), 1454 (m), 1388 (m), 1182 (s, s-0), 725 (m); elemental analysis for C47H86O2: calculated: C - 82,55%, N - 12,59%; found: C - At 82.70%, N - 12,50%; melting point (DSC - differential scanning calorimetry): 103-105C.

Example 2

-Sitosterolemia receive the 4 and stigmastanol allocate using the method described above.

The results of the analysis of selected compounds are shown below.

1H NMR (Dl3): (4,62 (quintet, 1H), 2,18 (t, 8, 2H), 1,88 (d, 12, 1H); IR (cm-1, CVG): 1739 (C=0), 1467 (m),1381 (m), 1176 (C-0), 718 (m); elemental analysis for C47H86O2: calculated: C - 82,55%, N - 12,59%; found: C - 82,31%, N 12,63%; so square (DSC): 101-S; % H2O (Karl Fischer) 0,73%.

Example 3

-Sitosterolaemia get through interaction-sitosterol and palmitic acid. As the catalyst used NaHS4and stigmastanol allocate using the method described above as method A. the results of the analysis of the selected stigmastanol below.

1H NMR (Dl3): (4,68 (quintet, 1H), 2,24 (t, 8, 2H), 1,95 (d, 12, 1H); IR (cm-1, CVG): 1739 (C=0), 1460 (m), 1394 (m), 1176 (C-0), 725 (m); elemental analysis for C45H82O2: calculated: C - 82,57%, N - 12,54%; found; C - 82,59%, N - 12,53%; melting point (DSC): 102-S.

Example 4

-Sitostanol get through interaction-sitostanol and oleic acid. As the catalyst used NaHSO4and the stigma is so.

1H NMR (Dl3): (5,27 (m, 2H), 4,62 (quintet, 1H), 2,23 (t, 8, 2H); IR (cm-1clean): 1739 (C=0), 1461 (m), 1387 (m), 1176 (C-0), 1010 (m), 718 (m); elemental analysis for C47H84O2: calculated: C - 82,80%, N of 12.33%; found: C - 82,98%, N - 12,36%; melting point (DSC): 41-S.

Example 5

Cholesterolemia get through interaction cholesterol and oleic acid. As the catalyst used NaHSO4and cholesterolemia allocate using the method described as method A. the results of the analysis are given below.

1H NMR (Dl3): (and 5.30 (m, 2H) and 4.65 (quintet, 1H), 2,22 (t, 8, 2H); IR (cm-1clean): 1725 (C=0), 1454 (s), 1367 (m), 1168 (m, 0), 1003 (m), 711 (m); elemental analysis for C45H80O2: calculated: C - 82,67%; N - 12,25%; found: C - 82,64%; N - 12,34%; melting point (DSC): 20-25S.

Examples

The interaction of the white oil of cinnamon and stanol by way interesterification gives a mixture of products with the following approximate reproducible distribution by weight:

Stanolone 67%,

Stenolineart 19%,

Stenolineart 9%,

Stenopelmatus 3%

Example 6

The interaction is performed with atora. Before the beginning of the reaction, add 0.2% activated charcoal. The mixture is heated to C, and see the appearance of water in the refrigerator. The reaction mixture is heated to C, and when the amount of fatty acids ceases to decrease, add water and then separated from the mixture. Then register that product color corresponds to about 8 on a scale of Gardner.

Example 7

Repeat the procedure of example 6 without coal, and the color washed out of the product complies with the 11+.

Example 8

Repeat the procedure of example 6, using as a catalyst of 0.2% zinc oxide. The product has 9 color on the Gardner scale. Examples 7 and 8 show the ease of use in the present invention the agent, decontamination color. To further improve the color can easily be achieved by changing the number of used decontamination coloring agent, and other process variables.

Example 9

Repeat the reaction used in example 6, but without catalyst. The reaction does not occur until temperatures above 200C, and to complete the reaction requires more than 10 hours at C or higher temperatures. This shows the advantage of the catalysts described here, whereby the reaction p is Manolov/sterols, consisting in the interaction of stanol/Sterol formula

and acid taken in stoichiometric or near stoichiometric ratio in the presence of a sufficient amount of a catalyst and a sufficient amount of decolorizing agent, with the formation of almost pure individual corresponding complex ester stanol/Sterol formula

where R1represents a carbon chain length of FROM about5-C25;

R2represents a carbon chain length of FROM about3-C15and indicates an optional double bond.

2. The method according to p. 1, where the reaction is performed in a neat environment with acid, acting as a solvent.

3. The method according to p. 1, where the catalyst is the substance of the main character in the water.

4. The method according to p. 3, where the catalyst is zinc oxide.

5. The method according to p. 1, where the corresponding ester of stanol/Sterol receive not less than about 98 wt.%.

6. The method according to p. 1, where R1in complex ester stanol/Sterol has a value of approximately C12-C21.

7. The method according to p. 1, where the reaction temperature is about 100 - Weg complex ester stanol/Sterol provide a way to fully water-based.

10. The method according to p. 1 wherein the decolorizing agent is coal or charcoal.

11. The method according to p. 1, where the amount of the decolorizing agent is about 0.05 to 1 wt.% in relation to the total reaction mass.

12. The method of obtaining esters of Stanlow/sterols, consisting in the interaction of stanol/Sterol formula

and polyunsaturated fatty acids with carbon chain length FROM6-C24taken in stoichiometric or near stoichiometric ratio in the presence of a sufficient amount of a catalyst and a sufficient amount of decolorizing agent, which results in almost pure individual corresponding complex ester stanol/Sterol.

13. The method according to p. 12, where the reaction is performed in a neat environment with polyunsaturated fatty acid acting as a solvent.

14. The method according to p. 12, where the catalyst is a Lewis acid.

15. The method according to p. 14, where the Lewis acid is zinc oxide.

16. The method according to p. 12, where the corresponding ester of stanol/Sterol receive not less than about 98 wt.%.

17. The method according to p. 12, where the temperature Rea is about on p. 12, where the selection of the appropriate complex ester stanol/Sterol provide a way to fully water-based.

20. The method of obtaining esters of Stanlow/sterols, consisting in the interaction of stanol/Sterol formula

and acid taken in stoichiometric or near stoichiometric ratio in the presence of a sufficient amount of catalyst is a Lewis acid and, optionally, a sufficient number of decolorizing agent, with the formation of almost pure individual corresponding complex ester stanol/Sterol formula

where R1represents a carbon chain length of FROM about3-C24;

R2represents a carbon chain length of FROM about3-C15and indicates an optional double bond.

Priority items:

21.06.1999 - PP. 1-20;

15.12.1998 - PP.1-20;

25.08.1998 - PP.1, 2, 5-9.

 

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3 cl, 3dwg, 1 tbl

FIELD: veterinary.

SUBSTANCE: claimed is method, which allows to separate from pregnant horse urine by hard-phase extraction mixture of conjugated estrogens, depleted of phenol urine components and non-conjugated lipophilic compounds from group including non-conjugated flavonoids, non-conjugated isoflavonoides, non-conjugated norisoprenoids, non-conjugated steroids, first of all, androstane and preganane steroids, and comparable with them non-conjugates compounds.

EFFECT: improved method of obtaining extract, containing natural mixture of conjugated horse estrogens.

16 cl, 3 ex, 2 tbl

FIELD: chemistry.

SUBSTANCE: described is a method of producing 7,8-dihydro-analogues of ecdysteroids via catalytic hydrogenation of ecdysteroids in methanol solution containing 1:6-fold excess Na metal in the presence of a Pd/C catalyst (1:1 to the weight of the substrate).

EFFECT: obtained 7,8-dihydro-analogues of ecdysteroids are structurally similar to castasterone type brassinosteroids - highly active phytohormones, plant growth and development stimulants.

3 cl, 4 ex

FIELD: chemistry.

SUBSTANCE: method of producing moronic acid involves treating 3β,28-diacetoxyolean-18(19)-ene with an alcoholic solution of an alkali while boiling, followed by separation of the formed 3β,28-dihydroxyolean-18(19)-ene, which is treated with a Jones reagent with molar ratio of 3β,28-dihydroxyolean-18(19)-ene to Jones reagent equal to 1:10 in acetone, mixing the reaction mixture for 4-5 hours at temperature of 0 - +5°C and separating the end product, where 3β,28-diacetoxyolean-18(19)-ene is obtained by reacting allobetulin with acetic acid anhydride in the presence of a catalytic amount of perchloric acid with molar ratio allobetulin: acetic anhydride: perchloric acid equal to 1:100:0.1, while boiling for 15-20 hours and then separating the product.

EFFECT: high efficiency of use.

2 cl, 1 ex

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