Method of producing 2-hydroxy-4-methylselenobutyric acid as separate substance or as mixture with sulphur-containing analogue thereof, and use thereof in nutrition, particularly animal nutrition

FIELD: chemistry.

SUBSTANCE: method comprises the following steps: reaction of 3-methylselenopropion aldehyde of formula (I): with an alkali metal cyanide of formula M+CN-, preferably in the presence of an alkali metal bisulphite salt of formula M+HSO3-, where M denotes an alkali metal atom, in a polar protic solvent, to obtain 2-hydroxy-4-methylselenobutyronitrile of formula (II): , hydrolysis of the compound of formula (II) in the medium of hot concentrated sulphuric acid, in a polar protic solvent, to obtain the desirable compound of formula (IV): , or hydrolysis of the compound of formula (II) in the medium of hot concentrated sulphuric acid, in a polar protic solvent, to obtain a compound of formula (III): , which can be hydrolysed in the medium of hot concentrated strong acid to obtain a compound of formula (IV). The compound of formula (IV) can be converted to one of its salts after adding a physiologically acceptable base. The invention also discloses a method of preparing a mixture of 2-hydroxy-4-methylselenobutyric acid and 2-hydroxy-4-methylthiobutyric acid and use thereof, 2-hydroxy-4-methylselenobutyronitrile and use thereof, and a dietary composition.

EFFECT: invention simplifies production of 2-hydroxy-4-methylselenobutyric acid.

17 cl, 7 ex

 

The present invention relates to a method for producing 2-hydroxy-4-methylselenocysteine acid in the form of individual substances or in the form of a mixture with its sulfur-containing analogue, as well as its application in the food, in particular, in animal feed.

Selenium is an essential trace element for mammals and, in particular, for people. In the form of L(+)-selenocysteine or L(+)-Selenomethionine he is involved in the biosynthesis of selenoproteins, such as glutathioneperoxidase, thioredoxins and selenoprotein R. According to the FDA-RDA (Recommended dietary Management standards for sanitary supervision of food and drug administration of the USA), the daily requirement for selenium in humans varies from 10-30 µg for children up to 40-70 µg for teenagers adults, and these levels are especially high in women during pregnancy (65 mcg/day) and lactation (75 µg/day). The complementation (in addition to the norm) L(+)-Selenomethionine (2.7 mmol of selenium equivalent) of lactating women significantly increases the concentration of selenium in their milk.

In some situations, such as deficits, illness or exposure to radiation, the complementation of food selenium has been proven to be very useful. This is especially true in the case of children suffering from genetic diseases such as phenylketonuria or hyperphenylalaninemia who have own udate diet with low levels of proteins. In another area associated with vitamins selenium in organic form, such as L(+)-Selenomethionine, has protective effects against UV radiation in humans. Finally, L(+)-Selenomethionine protects against the harmful biological effects of high-energy ionizing radiation.

In the application for a French patent on the name of the same applicant (FR 2873376) for the first time disclosed 2-hydroxy-4-methylselenocysteine acid and its derivatives, as well as methods for their synthesis. Moreover, its sulfur-containing analogue of 2-hydroxy-4-meticiously acid, also known as liquid methionine, known as a precursor of methionine for animal nutrition (WO 9636598). For this application it is produced industrially in the scale of several hundred thousand tons per year.

Therefore, 2-hydroxy-4-methylselenocysteine acid precursor of L(+)-Selenomethionine, and 2-hydroxy-4-meticiously acid is the precursor of L(+)-Selenomethionine are compounds which are of exceptional interest in animal feed. Therefore, it is important to have easy ways of industrial synthesis, i.e. those that can be implemented on a large scale, the easiest way, the use and value of which are not significant obstacles.

The applicant has developed a method of synthesis that meets these criteria is which has many advantages over existing methods.

Thus, in the first aspect of the present invention relates to a method for producing 2-hydroxy-4-methylselenocysteine acid, characterized in that it involves the following stages:

interaction 3-methylselenocysteine formula (I):

,

with alkali metal cyanide of the formula M+CN-, preferably in the presence of a bisulfite salt of an alkali metal formula M+HSO3-where M represents an alkali metal atom, proton polar solvent,

obtaining compound 2-hydroxy-4-methylselenocysteine formula (II):

,

the compound of formula (II) hydrolyzing in an environment of hot concentrated strong acid, proton polar solvent to obtain compounds of formula (IV):

,

which can be converted into one of its salts after adding a physiologically acceptable base.

Alternatively, the method described above, the compound of formula (II) hydrolyzing in an environment of hot concentrated sulfuric acid, proton polar solvent to obtain compounds of formula (III):

,

the compounds of formula (III), which itself is hydrolyzed in an environment of hot concentrated strong acid with obtaining joint is of the formula (IV).

According to a preferred embodiment of the method according to the invention the reagent cyanide of an alkali metal selected from sodium cyanide, potassium cyanide and cyanide lithium.

The reaction is carried out in proton polar solvent such as, for example, water.

Subsequent reaction by which the compound of formula (IV) can be converted to its corresponding salt, carried out under standard conditions known to the person skilled in the field.

The method according to the present invention has the advantage that it does not require any complex reagents, such as ORGANOMETALLIC compounds or toxic agents, such as alkylating agents, as in the methods of the prior art (FR 2573376). In addition, it can be implemented on a large scale, in non-toxic solvents, such as, for example, water. In addition to the aspect of feasibility, these advantages are also significantly reduce the cost of application.

The compound of formula (I), which is used as the starting material for the application of the method according to the invention is known, and how to get it, in particular, described in the publication Synthesis, 1988, pages 616-619.

The advantage of the sulfur-containing analogue of the compounds of formula (IV)described above, 2-hydroxy-4-methylthiophenol acid, is widely known (see above), in particular, in the same area of supply.

Although the TES introduction of this compound and the compounds of formula (IV) has the obvious advantage in the context of the use and effectiveness. In order to meet the needs of industrial production, it is important to have both of these compounds in the mixture and, in addition, to control the relative content of both of these derivatives with respect to each other. Their introduction, either simultaneously or separately, as part of preparations in a certain ratio could also provide a significant advantage.

The applicant has shown that the method of receiving according to the present invention, described above, can be used for simultaneous receipt of a mixture of two sulfur and selenium compounds, which significantly improve industrial performance.

Thus, in the second aspect of the present invention relates to a method for producing a mixture of 2-hydroxy-4-methylselenocysteine acid and 2-hydroxy-4-methylthiophenol acid in a certain ratio, which is characterized by the fact that it involves the following stages:

interaction of a mixture of 3-methylselenocysteine formula (I) and 3-methylthiopropionate formula (Ia):

,

with alkali metal cyanide of the formula M+CN-, preferably in the presence of a bisulfite salt of an alkali metal formula M+HSO3-where M represents an alkali metal atom, proton polar solvent,

to obtain compounds is 2-hydroxy-4-methylselenocysteine formula (II) and 2-hydroxy-4-methylthiopyrimidine formula (IIa):

,

as a result of hydrolysis in the environment of hot concentrated strong acid, proton polar solvent, gives a mixture of the two expected compounds of formulas (IV) and (IVa):

,

which can be converted into their salts mixture after adding a physiologically acceptable base,

moreover, it should be understood that the relative content of both compounds (IV) and (IVa) are set at the beginning of the method, the relative amounts of the compounds (I) and (Ia) and continue throughout the above receipt.

In a preferred aspect, the reagent cyanide of an alkali metal selected from sodium cyanide, potassium cyanide and cyanide lithium.

The reaction is carried out in proton polar solvent such as, for example, water.

In the method according to the invention, as described above, the relative content of the two compounds of formulae (IV) and (IVa) control, and can be set depending on the intended application. In particular, the ratio between the compound (IV) and compound (IVa) is from 0.01% to 1% by weight and preferably from 0.05% to 0.5% by mass.

While obtaining the compounds of formulas (IV) and (IVa), respectively predecessors Selenomethionine and methionine, it is also possible to obtain a composition containing the mixture, because the handling of the panel is attached.

Thus, the aim of the present invention is also a composition, in particular a food composition containing as active ingredient a mixture of 2-hydroxy-4-methylselenocysteine acid of formula (IV) and 2-hydroxy-4-methylthiophenol acid of the formula (IVa) and physiologically acceptable medium. The ratio between the compound (IV) and compound (IVa) may, in particular, from 0.01% to 1.0% by weight and preferably from 0.05% to 0.5% by mass.

Under physiologically acceptable medium in the context of the present invention involve the environment, in particular chosen from:

water, alcohol solution or oil,

water/oil or oil/water emulsions, microemulsions,

- water gel,

- dispersion of vesicles, microcapsules, microparticles or nanoparticles,

- solid medium consisting of one or more additives and/or excipients, which may be selected from vitamins, natural antioxidants, mineral salts, mono-, di - or polysaccharides, in particular, folic acid, vitamin B6, E or S, lactose, starch. This solid medium consisting of one or more additives and/or excipients as defined above and containing at least one of the compounds of General formula (I)may be prepared in the form of gelatin capsules, tablets or powder. Number of different components of these compositions is s, different from the compounds of formula (IV) and (IVa)are the quantities usually used for these applications.

As non-limiting examples only to illustrate, and which therefore can not in any way limit the scope of the invention, these environments can be a nutritious liquid, such as, for example, food, milk, fruit juices, syrups, and milk for infants, or parenteral solution, table salt, or in General any food, supplemented with selenium in a controlled way.

The invention also relates to the application of a mixture of 2-hydroxy-4-methylselenocysteine acid of formula (IV) and 2-hydroxy-4-methylthiophenol acid of the formula (IVa) as a food ingredient, additions or supplements.

The compound 2-hydroxy-4-methylselenocysteine formula (II):

,

is new and as such is part of the invention and its enantiomers.

In the context of the present invention as a physiologically acceptable reasons can be mentioned a non-limiting way, mineral bases such as the hydroxides of sodium, lithium, calcium, potassium, magnesium, ammonium or zinc carbonates of alkaline or alkaline earth metals, such as carbonates and bicarbonates of sodium, lithium, calcium, potassium, magnesium, AMM is of or zinc, or organic bases such as methylamine, Propylamine, trimethylamine, diethylamine, triethylamine, N,N-dimethylethanolamine, Tris(hydroxymethyl)aminoethane, ethanolamine, pyridine, picoline, dicyclohexylamine, morpholine, protein, lysine, arginine, histidine, N-methylglucamine, or more postname salts such as alkylphosphate salt, arylphosphonate salt, arylalkylamines salt, alkenylboronic, or Quaternary ammonium salts such as salts of Tetra-n-butylamine.

The compound of formula (II) used in the scope of the present invention as an intermediate compound in the synthesis in obtaining the compounds of formula (IV), which can be converted into a Selenomethionine. For example, the object of the invention is also the use of compounds of formula (II), as previously defined, or enantiomers as sources of Selenomethionine and/or selenium in humans or animals.

In addition, implies, in particular, the use of the compounds of the formula (II) as:

precursor L(+)-Selenomethionine, either directly or after enzymatic hydrolysis, oxidation and transamination in vivo;

or as:

sources of selenium to compensate for partial or complete deficiency of selenium;

or as:

- food ingredients, supplements or additives to manufacture the Oia food compositions for animal feed (more specifically for cattle, sheep, pigs, horses, cats and dogs, and poultry).

The following examples are offered merely as illustrations and are not able in any way to limit the scope of the invention.

Example 1: Obtaining 2-hydroxy-4-(methylsilane)butyronitrile

468 mg (3.1 mmol) of 3-methylselenocysteine (R.Dieden et L. Hevesi, Synthesis 1988, 616-619) are added to a solution of 291 mg (2.8 mmol) of sodium bisulfite in 1.2 ml of water. The mixture is vigorously stirred for 10 min at room temperature and then added 155 mg (3,16 mmol) of sodium cyanide. After 2 h stirring at room temperature, add 5 ml of dichloromethane and the organic phase discarded. The aqueous phase is extracted a second time with 5 ml dichloromethane. The organic phase is collected and then after drying (Na2SO4), filtration and evaporation obtain the desired compound as a colourless oil, which can be used as such in the next stage.

Rf(SiO2, cyclohexane/ethyl acetate, 50/50): 0,22.

NMR1H (CDCl3, 300 MHz): δ (m-1)=2.06 (s, 3H); 2.27 (m, 2H); 2.73 (m, 2H); 3.20 (bs, 1H, OH); 4.74 (t, J=8 Hz, α-H).

MS (mass spectrometry) (IE (ionization energy), 70 eV): m/z (%) = 179 (80, M+); 164 (90); 153 (100); 123 (50); 109 (80).

Example 2: Obtain D,L-2-hydroxy-4-methylselenocysteine acid by hydrolysis of 2-hydroxy-4-(methylsilane)butyronitrile

390 mg (2.1 mmol) of the compound described in Example 1, is added to a mixture of 1.7 ml of concentrated hydrochloric acid and 3.6 ml of water. The mixture is heated at reflux distilled for 6 h and then stirred for 14 h at room temperature. Then the aqueous phase is extracted with 3×10 ml tert-butyl methyl ether. After drying (Na2SO4), filtration and evaporation obtain the desired compound in the form of oil, which crystallizes on cooling.

Rf (SiO2, cyclohexane/ethyl acetate, 50/50+1% CF3COOH): 0,26.

NMR1H (CDCl3, 300 MHz): δ (m-1) = 2.02 (s, 3H, SeCH3); 2.08 (m, 1H); 2.22 (m, 1H); 2.70 (m (SIM.), 2H); 4.41 (dd, J=8 Hz, J=4 Hz, 1H, α-H).

Example 3: Obtaining D,L-2-hydroxy-4-methylselenocysteine acid amide

262 mg (1,47 mmol) 2-hydroxy-4-(methylsilane)butyronitrile described in Example 1, is added to a mixture of 0.13 ml of water and 0.5 ml of concentrated sulfuric acid. The mixture is heated to 45°C for 2 h and then add 5 ml of water and 5 ml of dichloromethane. The organic phase is discarded and the aqueous phase is extracted a second time in 5 ml of dichloromethane. The organic phase is collected and then after drying (Na2SO4), filtration and evaporation obtain 48 mg of the desired compound as a viscous colorless oil.

Rf(SiO2, cyclohexane/methanol, 90/10): 0,13.

NMR1H (CDCl3, 300 MHz): δ (million1) =2.06 (s, 3H, SeCH3); 2.08 (m, 1H); 2.30 (m, 1H); 2.75 (m (SIM.), 2H); 3.25 (bs, 1H, OH); 4.36 (dd, J=8 Hz, J=4 Hz, 1H, α-H); 5.5 (bs, 1H, NH2); 6.5 (bs, 1H, NH2).

MS (IC, NH): m/z (%) = 215 (40, M+NH4)+; 198 (100, M+NH4)+; 181 (20); 102 (25).

Example 4: the mixture according to the invention

Phase A: a mixture of 2-hydroxy-4-(methylthio)butyronitrile and 2-hydroxy-4-(methylsilane) butyronitrile.

,

120 mg (0.8 mmol) of 3-methylselenocysteine (R.Dieden and L. Hevesi, Synthesis 1988, 616-619) and 273 mg (2.5 mmol) of 3-methylthiopropionate added to a solution of 312 mg (3 mmol) of sodium bisulfite in 1.2 ml of water. The mixture is vigorously stirred for 10 min at room temperature and then added 164 mg (3.3 mmol) of sodium cyanide. After 2 h stirring at room temperature, add 5 ml of dichloromethane and the organic phase discarded. The aqueous phase is extracted a second time in 5 ml of dichloromethane. The organic phase is collected and then after drying (Na2SO4), filtration and evaporation gives a blend of 2-hydroxy-4-(methylthio)butyronitrile and 2-hydroxy-4-(methylsilane)butyronitrile in the ratio of 3:1 in the form of a yellowish oil, which can be used as such in the next stage.

NMR1H (CDCl3, 300 MHz): δ (m-1) = 2.06 (s, SeCH3); 2.16 (s, S3), 2.10-2.35 (m); 2.50-2.65 (m); 2.64-2.90 (m); 3.20 (bs, OH); 4.74 (t, J=8 Hz, 2-H, Se connection); 4.76 (t, J=8 Hz, 2-H, S link is).

Stage: Obtaining a mixture of D,L-2-hydroxy-4-methylselenocysteine acid and D,L-2-hydroxy-4-methylthiophenol acid.

105 mg of the product described on the stage And add to the mixture of 0.6 ml of concentrated hydrochloric acid and 1.3 ml of water. The mixture is heated at reflux distilled for 5 h and then the aqueous phase is extracted with 2×10 ml tert-butyl methyl ether. After drying (Na2SO4), filtration and evaporation gives a blend of 2-hydroxy-4-(methylthio)butyric acid and 2-hydroxy-4-(methylsilane)butyric acid in a ratio of 3:1 in the form of a yellowish oil.

ES (elektrorazpredelenie) (LC-MS (liquid chromatography - mass spectrometry): tR=1,69 min: 148,9 (M[C5H10O3S]-H+);

tR=2,24 min: 196,8 (M[C5H10O3Se]-H+).

Example 5: obtain the compositions according to the invention

Example A: Gelatin capsules were obtained in a standard way according to the following composition:

L-2-hydroxy-4-methylselenocysteine acid0.2 mg
L-2-hydroxy-4-meticiously acid200 mg
Excipients* and encapsulation**
how much is required for gelatin capsules 1000 mg
(* corn starch, lactose, magnesium stearate, sodium lauryl sulfate,
** gelatin, titanium dioxide, dyes).

Example 5.8: Gelatin capsules were obtained in a standard way according to the following composition:

L-2-hydroxy-4-methylselenocysteine acid0.05 mg
L-2-hydroxy-4-meticiously acid50 mg
Excipients* and encapsulation**
as needed to gelatin capsules1000 mg
(* corn starch, lactose, magnesium stearate, sodium lauryl sulfate,
** gelatin, titanium dioxide, dyes).

Example 5.C: Gelatin capsules were obtained in a standard way according to the following composition:

L-2-hydroxy-4-methylselenocysteine acid10 mg
L-2-HYDR the XI-4-meticiously acid 10 mg
Wateras needed
up to 1000 mg

1. The method of obtaining 2-hydroxy-4-methylselenocysteine acid, characterized in that it comprises the stage of:
interaction 3-methylselenocysteine formula (I):
,
with alkali metal cyanide of the formula M+CN-, preferably in the presence of a bisulfite salt of an alkali metal formula M+HSO3-where M represents an alkali metal atom, proton polar solvent,
to obtain compounds 2-hydroxy-4-methylselenocysteine formula (II):
,
the compound of formula (II) hydrolyzing in an environment of hot concentrated hydrochloric acid, proton polar solvent, to obtain the expected compound of formula (IV):
,
or
the compound of formula (II) hydrolyzing in an environment of hot concentrated sulfuric acid in proton polar solvent to obtain compounds of formula (III):
,
which itself is hydrolyzed in an environment of hot concentrated strong acid to obtain the compounds of formula (IV), then
the compound of formula (IV) can the be converted into one of its salts after adding a physiologically acceptable base.

2. The method according to claim 1, characterized in that the cyanide is an alkali metal selected from sodium cyanide, potassium cyanide and cyanide lithium.

3. The method according to claim 1, characterized in that the proton polar solvent is a water.

4. The method according to claim 2, characterized in that the proton polar solvent is a water.

5. The method of obtaining a mixture of 2-hydroxy-4-methylselenocysteine acid and 2-hydroxy-4-methylthiophenol acid, wherein the stage includes:
interaction of a mixture of 3-methylselenocysteine formula (I) and 3-methylthiopropionate formula (Ia):
,
with alkali metal cyanide of the formula M+CN-, preferably in the presence of a bisulfite salt of an alkali metal formula M+HSO3-where M represents an alkali metal atom, proton polar solvent,
to obtain a mixture of 2-hydroxy-4-methylselenocysteine formula (II) and 2-hydroxy-4-methylthiopyrimidine formula (IIa):
,
- as a result of hydrolysis in the environment of hot concentrated strong acid, proton polar solvent, gives a mixture of the two expected compounds of formulas (IV) and (IVa):
,
which can be converted into their salts mixture after adding a physiologically acceptable the reason, moreover, the relative content of both compounds (IV) and (IVa) are set at the beginning of the method, the relative amounts of the compounds (I) and (Ia) and maintained throughout the above receipt.

6. The method according to claim 5, characterized in that the cyanide is an alkali metal selected from sodium cyanide, potassium cyanide and cyanide lithium.

7. The method according to claim 5, characterized in that the proton polar solvent is a water.

8. The method according to claim 6, characterized in that the proton polar solvent is a water.

9. The method according to claim 5, characterized in that the mass ratio of the compound (IV) to the compound (IVa) is from 0.01 to 1.0, preferably from 0.05 to 0.5.

10. The method according to claim 6, characterized in that the mass ratio of the compound (IV) to the compound (IVa) is from 0.01 to 1.0, preferably from 0.05 to 0.5.

11. The method according to claim 7, characterized in that the mass ratio of the compound (IV) to the compound (IVa) is from 0.01 to 1.0, preferably from 0.05 to 0.5.

12. The method according to claim 8, characterized in that the mass ratio of the compound (IV) to the compound (IVa) is from 0.01 to 1.0, preferably from 0.05 to 0.5.

13. The compound 2-hydroxy-4-methylselenocysteine formula (II):
.

14. The use of the compounds of formula (II)described in article 16, as sources of Selenomethionine and/or selenium in humans and is in animals.

15. Food composition containing as active ingredient a mixture of 2-hydroxy-4-methylselenocysteine acid of formula (IV) and 2-hydroxy-4-methylthiophenol acid of the formula (IVa) and physiologically acceptable medium.

16. The composition according to item 15, wherein the mass ratio of the compound (IV) to the compound (IVa) is from 0.01 to 1.0, preferably from 0.05 to 0.5.

17. The application of a mixture of 2-hydroxy-4-methylselenocysteine acid of formula (IV) and 2-hydroxy-4-methylthiophenol acid of the formula (IVa) as a food ingredient, additions or supplements.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing [1,4]selenazino[2,3,4-i,j]quinolinium chlorides of general formula where R1 is phenyl, R2 is alkyl, phenyl or hydrogen, R1+R2 is cycloalkyl. The method involves reaction of the corresponding olefin with 8-quinoline selenenyl chloride in equimolar ratio in methylene chloride medium. The disclosed substances can be used in fine organic synthesis, in production of medicinal agents and biologically active substances.

EFFECT: efficient method of obtaining chlorides.

4 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to N,Se-substotuted of N'-1-(alkyl(hetero)aryl)-N'-1-(alkyl(hetero)aryl)isoselenourea: , where R1 represents alkyl, cycloalkyl, alkenyl, aryl; R2 - hydrogen or lower alkyl; R3, R4 can be similar or different and independently represent aryl, heteroaryl; R5 represents hydrogen or lower alkyl; m=0-2, n=1-3; X represents anion residue of inorganic or organic acid, symbol "*" means possibility of presence of chiral carbon atom.

EFFECT: obtaining N,Se-substotuted of N'-1-(alkyl(hetero)aryl)-N'-1-(alkyl(hetero)aryl)isoselenourea, possessing neuroprotective action.

8 ex

FIELD: medicine.

SUBSTANCE: invention refers to a new product in the form of solution for treatment of benign, virus, premalignant and malignant nonmetastasing skin affections, dysontogenetic lesions of visible mucous membranes, skin mycoses, wrinkle correction and senile pigment spots. The product represents a compound of general formula H2SeO3·x·[R-CXY-(CH2)m-COOH], where x=2-6 prepared from reaction of selenium dioxide and haloid carboxylic acids of general formula R-CXY-(CH2)m-COOH, where R = phenyl, alkyl of general formula CnH2n+1; n=1-5, X=H or Y, Y=F, CI, Br or J, m = 0-10. Besides, the invention concerns a product in the form of solution for treatment benign, virus, premalignant and malignant nonmetastasing skin affections, dysontogenetic lesions of visible mucous membranes, skin mycoses, wrinkle correction and senile pigment spots, containing 0.1-50 wt % of said product, 1-99 wt % of haloid carboxylic acids and the rest - water. Also the invention concerns method of treatment of various skin diseases, including topic applications of the product.

EFFECT: improved clinical effectiveness of the product and method of treatment.

6 cl, 3 dwg, 1 tbl, 68 ex

FIELD: chemistry.

SUBSTANCE: claimed invention relates to method of obtaining organic salts, which contain anions of bis(perfluoroalkyl)phosphinate and can be applied in organic synthesis. Difference of claimed method lies in the fact that it includes carrying out reaction of tris(perfluoroalkyl)phosphinoxide with alcohol and organic base, stronger than alcohol.

EFFECT: elaboration of new method of obtaining organic salts with properties of ionic liquids.

11 cl, 14 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to derivatives of butyric acid of the formula (I): wherein A means carboxyl or (C6-C18)-alkoxycarbonyl; B means ethylene group -CH2-CH2-; R1 means benzyl optionally substituted in phenyl ring, optionally substituted phenyl or optionally substituted pyridyl; Z represents sulfur (S) or selenium (Se) atom; n means a whole number = 0, 1 or 2; R2 represents radical chosen from optionally substituted phenyl, optionally substituted benzopyridine, optionally substituted benzothiazole, optionally substituted quinolyl, optionally substituted naphthyl, optionally substituted triazole and radical of the formula: Also, invention describes methods for synthesis of compounds of the formula (I) and pharmaceutical composition based on thereof. Compound can be used in preparing a medicine designated for treatment or prophylaxis of dyslipidemia and diabetes mellitus.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

9 cl, 1 tbl, 81 ex

The invention relates to medicine and applies to new analogues of fatty acids of General formula (1), pharmaceutical compositions for and methods of treating or preventing obesity, hypertension, fatty infiltration of the liver, multiple metabolic syndrome nutritional compositions and method of improving the quality of such products as meat, milk and eggs

The invention relates to new compounds of the formula (I)

< / BR>
where AG represents a radical selected from formulas (a) and (b) below:

< / BR>
R1represents a halogen atom, -CH3CH2OR SIG7, -OR SIG7, СОR8, R2and R3taken together form a 5 - or 6-membered ring, R4and R5represent H, a halogen atom, a C1-C10-alkyl, R7represents H, R8represents H orX represents the radical-Y-C-, r' and r" is H, C1-C10alkyl, phenyl, Y represents S(O)nor SE, n = 0, 1, or 2, and salts of compounds of formula (I)

The invention relates to selenoorganicheskikh compounds, namely 1-methoxy-1-(2-chlorpheniramine)alkanal formula I

CH3-O-H-SEwhere R is methyl or isopropyl, exhibiting anti-inflammatory and antimicrobial activity

The invention relates to new biologically active compounds, specifically to hydrochloridum of aminosilanes aromatic series formula I

= CH-Se-Ar where R is methyl; R1is methyl or ethyl;

Ar - p-or-were, p-chlorophenyl or- naphthyl, showing a phosphate-protecting action

FIELD: food industry.

SUBSTANCE: invention relates to food industry and may be used for production of a functional food product immediately consumed as a medical and preventive food product. The functional food product consists of vegetable phospholipids, ascorbic acid, fat-soluble vitamins - vitamin E and β-carotene, sugar or its substitute, water-soluble vitamin B1, B2 and B6, ferric sulphate, a dry water-soluble extract of rosehips, a dry water-soluble extract of common licorice roots.

EFFECT: functional food product has high antitoxic properties.

1 tbl, 2 ex

FIELD: food industry.

SUBSTANCE: invention relates to food industry and may be used for production of a functional food product immediately consumed as a medical and preventive food product. The functional food product consists of vegetable phospholipids, ascorbic acid, fat-soluble vitamins - vitamin E and β-carotene, sugar or its substitute, ferric sulphate, flavonoids, a dry water-soluble extract of Karkade tea, a dry water-soluble extract of common licorice roots.

EFFECT: functional food product has high radioprotective properties.

1 tbl, 2 ex

FIELD: food industry.

SUBSTANCE: invention relates to a fermented product and such fermented product production method and may be used for metabolic syndrome prevention. The fermented product produced by way of addition of food microorganisms into grains of a crop selected from among barley, oat, rye, triticale, sorghum or a mixture thereof and the grains fermentation with such food microorganisms.

EFFECT: method allows to reduce carbohydrates content and increase that of beta-glucan in the fermented product.

17 cl, 3 tbl, 1 ex

FIELD: food industry.

SUBSTANCE: invention relates to food industry and refers to production of a dietary supplement intended for using in food products, primarily - for enrichment with iron. The method includes interaction of water solution of sodium lactate with concentration equal to 58.2-61.4 wt % with water solution of heptahydrate iron sulphate with concentration equal to 40-50 wt % (in the process of stirring) during 1.5-2.5 hours at a temperature of 35-45°C in carbon dioxide or hydrogen resulting in iron lactate crystals formation. The weight ratio between the water solutions of sodium lactate and iron sulphate is 1:(1.42-1.88). The produced iron lactate crystals are separated from the drinking water till complete absence of sulphates in The flush water. Then iron lactate crystals are dried under vacuum with depression equal to at least 94 kPa at a temperature no more than 70°C.

EFFECT: invention allows to produce an iron lactate dietary supplement with improved quality and a high product output.

1 tbl

FIELD: food industry.

SUBSTANCE: invention relates to food industry and refers to production of a dietary supplement intended for using in food products, primarily - for enrichment with iron. The method includes interaction of water solution of sodium lactate with concentration equal to 58.2-61.4 wt % with water solution of heptahydrate iron sulphate with concentration equal to 40-50 wt % (in the process of stirring) during 1.5-2.5 hours at a temperature of 35-45°C in carbon dioxide or hydrogen resulting in iron lactate crystals formation. The weight ratio between the water solutions of sodium lactate and iron sulphate is 1:(1.42-1.88). The produced iron lactate crystals are separated from the drinking water till complete absence of sulphates in The flush water. Then iron lactate crystals are dried under vacuum with depression equal to at least 94 kPa at a temperature no more than 70°C.

EFFECT: invention allows to produce an iron lactate dietary supplement with improved quality and a high product output.

1 tbl

FIELD: food industry.

SUBSTANCE: invention relates to food industry and may be used for production of a functional food product immediately consumed as a medical and preventive food product. The functional food product consists of vegetable phospholipids, ascorbic acid, fat-soluble vitamins - vitamin E and β-carotene, sugar or its substitute, ferric sulphate, flavonoids, a dry water-soluble extract of Karkade tea, a dry water-soluble extract of common licorice roots.

EFFECT: functional food product has high antitoxic properties.

1 tbl, 2 ex

FIELD: food industry.

SUBSTANCE: invention relates to food industry, namely - methods for production of milk-containing food products. The method may be used for preparation of preventive-purpose products for improvement of immunity with individuals belonging to different age groups. During production of the fermented milk-containing oat food product the oat mixture to be fermented is prepared by way of mixing water-diluted milk with extruded oatmeal with particle size equal to (50-300)*10-6 cm in an amount of 100 g per 1000 ml of the milk-containing base with weight content of water in the mixture not in excess of 49%. The mixture to be fermented is pasteurised at a temperature of 75°C - 85°C during 8-10 min and cooled to a fermentation temperature. One introduces a starter into the mixture and proceeds with fermentation during 3-5 hours at a temperature of 32°C - 42°C and cooling to 6°C - 2°C. One performs food fillers introduction, stirring and cooling.

EFFECT: method allows to produce a product with pleasant taste and preventive medical properties, enriched with proteins containing highly bioavailable essential amino acids.

4 cl, 4 ex

FIELD: medicine.

SUBSTANCE: group of inventions refers to medicine, namely gastroenterology and nutritional science, and may be used for treating and preventing metabolic and digestive disorders and related pathological conditions. That is ensured by introducing a food combination which contains mechanically processed grain shorts and meat or a dried product specified in the following group: fruit, vegetables, berries or any their combination.

EFFECT: using the given inventions enables higher therapeutic effect in metabolic and digestive disorders ensured by their normalisation.

20 cl, 6 ex

FIELD: food industry.

SUBSTANCE: proposed inventions group relates to a fermented and pasteurised liquid natural product, to its production method, application and to a container for the product storage. The fermented and pasteurised liquid natural product is produced based on fruit, vegetables, leguminous crops, herbs and/or nuts, contains living probiotic microorganisms in an amount of 105 - 1015 cells/ml and an excessive portion of non-living probiotic microorganisms. The method for production of fermented and pasteurised liquid natural product consists in addition of probiotic microorganisms (both for living and non-living) into the product fermented and pasterurised liquid base immediately prior to consumption. The produced product may be consumed both for oral and for external application, for example, for body wraps or compresses.

EFFECT: proposed inventions group usage will allow to enhance activation of the immune system.

32 cl, 1 dwg, 1 ex

FIELD: food industry.

SUBSTANCE: invention relates to production of a biologically active food additive and may be used for preventive alimentation. Milled horseradish root is infused in water during no less than 24 hours at a ratio of S: L = 1: (4.5 -5.0). The water extract is subjected to vacuum sublimation dehydration. Produced sublimated horseradish root powder in an amount of 25-35 g is mixed with 900-1100 g of natural floral honey. One introduces (while thoroughly stirring) magnolia vine oil into the mixture in an amount of 35-45 drops per 1000 g of the mixture.

EFFECT: simple mixing of the initial components, in a strictly specified ratio without modification of their chemical composition allows to enhance efficiency of the biologically active food additive impact on the immune system and to strengthen antiviral activity.

2 ex

FIELD: food raw and industry.

SUBSTANCE: invention relates, in particulate, to new nutrient sources of trace elements with using the milk proteins hydrolyzate enriched with trace elements. The nutrient chelate complex comprising the milk proteins hydrolyzate and trace elements bound to chelate compounds comprises trace elements in the range of concentrations 1-30 mg/g being from that at least 90% are in an organic form. Invention provides the preparing the nutrient source of trace elements with high assimilability of its components, improved functional properties and reduced adverse unfavorable effect in overdosing due to the elevated content of trace elements in organic form in its composition.

EFFECT: valuable properties of complex.

3 cl, 6 ex

Up!