A substance that lowers the level of cholesterol in the serum, and method thereof


(57) Abstract:

The invention relates to a substance that lowers the levels of cholesterol in serum and which is a complex ether-sitosterol and fatty acid or mixture of fatty acid ester, and method of its production. The substance can be used as such or added to food. 2 C. and 7 C.p. f-crystals, 4 PL.

The invention relates to a substance that lowers cholesterol levels, and how to obtain it.

High level of cholesterol in blood serum can be lowered by changing the metabolism of lipids in the intestine. In this case, the task may be hampered by the absorption of triglycerides, cholesterol or bile acids. In several studies it was observed that some plant sterols, such as sitosterol (24-ethyl-5-cholesten-3 b-ol) and its attached form b-sitosterol (24-ethyl-5a-cholestan-3 b-ol), reduce the levels of cholesterol in serum by reducing the absorption of dietary cholesterol from the intestine [1-25] the Use of plant sterols can be considered safe, since plant sterols are natural components of vegetable fats and oils. Themselves of plant sterols are not absorbed from ciasna associated with the reduction of cholesterol in the serum, in particular LDL cholesterol. The high value of cholesterol in serum is the most significant proof of the existence of the risk of coronary disease.

The degree of absorption of cholesterol depends on heredity, apoprotein E-phenotype. Apoprotein E is a protein that belongs to the lipoproteins of the blood serum and is involved in the transport of cholesterol in the system [26] For the alleles associated with the synthesis of apoprotein E, that is, lipoprotein, which affects the absorbance of known three types, E2, E3 and E4, which are combined in random pairs. Alleles can form a total of six different combinations. The higher the amount of subindexes, the better the absorption ability of cholesterol and the higher the level of cholesterol, in particular harmful LDL cholesterol in the serum [27] E4 allele is the most represented among hereditary factors Finn (Finns), so the ratio is almost double in comparison with many European populations [28] the Finns really are extremely sensitive to nutritional deficiencies and fat and high cholesterol food [29]

Cholesterol levels in the serum can be reduced by diet is, however, this path does not always lead to a satisfactory result. Other methods suitable for all, to achieve the reduction of cholesterol level in blood serum should be considered in comparison with these methods. The high concentration of fiber in the diet is a method with limited action. Lowering cholesterol effect of soluble fiber in food is based on the binding and removal of bile acids. Since the absorption of cholesterol is the main indicator of regulating the level of cholesterol in the serum is logical to seek to develop methods by which the absorption of cholesterol can be prevented or reduced.

Pollak showed that absorbed plant sterols lowered cholesterol levels in serum in men [1] The same has previously been observed in experimental animals [2,3] various studies have shown that large doses of plant sterols lower cholesterol levels in the serum, in the best cases, 10-20% [4,5] In these experiments were used in large quantities, up to 24 g/day, b-sitosterol in crystalline form [6] In some experiments, the level of cholesterol in the serum was significantly decreased even at lower davnym for lowering serum cholesterol [8] Drugs sitosterol have basically, good tolerability with long-term use [9]

Natural plant sterols are structurally related to cholesterol. The difference between the cholesterol molecule and a molecule of plant Sterol primarily found in the structure of the side chain of the basic skeleton. Ordinary food contains 100-300 mg per day of plant sterols. The majority of plant sterols in the diet is b-sitosterol and approximately one third of this campesterol. A small amount of saturated sitostanol also present in the products. Usually the concentration of campesterol in serum partly reflect the degree of cholesterol absorption [10-12] Changing amounts of plant sterols in the diet affects the level of serum cholesterol, but this area is still poorly understood. Plant sterols are poorly absorbed from the intestine. Plant sterols, which are limited absorbed in the system (less than 10% of sterols) [30-32] are excreted in the bile and through her with a chair. At the present time is easy to measure the levels of Sterol from food samples, serum or stool methods gas chromatography. Levels in the serum part depend on the quantities of plant sterols from food and part from the absorption efficiency of Stero the sorbed plant Sterol is allocated from the system with bile.

Even large doses absorbed plant sterols are not evident in the level of serum plant Sterol. Values remain at a normal level, as in humans, the absorption of plant Sterol quickly saturated. The level of plant Sterol in the serum rises to dangerous in small cases of rare diseases, such as cerebrocortical xanthomata and sitosterolemia [33-35] in comparison with whom coronary artery disease is common. The manifestation of these diseases is only in a few cases per million. No cases of these diseases were not observed in Finland. High values of plant Sterol sometimes observed in patients suffering from certain diseases of the liver [36]

Studies of cholesterol metabolism showed that sitosterol inhibits the absorption of both endogenous and dietary cholesterol from the intestine [13,14] As a result, decreases the secretion of neutral steroids in the stool, which leads to the lack of cholesterol in the liver and, through it, to the low level of serum cholesterol. On the other hand, sitosterol has no effect on the absorption of bile acids [13]

On the basis of experiments on animals, it seems, [15-17] Similar results were obtained also for humans [37] Various plant sterols showed the effect of different paths on the absorption of cholesterol [19,38] Previous studies conducted on experimental animals, has created the impression that sitostanol is the most effective inhibitor of cholesterol absorption [38] and he almost absorbed. Further study without control of six of the subjects showed that free sitostanol (1.5 g per day) lowers serum cholesterol (predominantly LDL cholesterol) within four weeks by 15% during the interval of two weeks cholesterol values are returned to the original levels [20] most of the drugs of plant sterols contain a number of different plant sterols. The action of a mixture of plant sterols on cholesterol absorption changes, as well as their own absorption [21-23]

Subsequent research has mainly focused on the study of the effects on the effectiveness of lowering serum cholesterol levels form (crystalline, suspension, granule), which enter the plant sterols. Crystal plant sterols do not possess a high degree of solubility in the phase of micelles in the supply channel and therefore cannot effectively inhibit the absorption of cholesterol. Only oils and fats determine the degree of solubility of free sterols. Only in rest the l inhibited in the experiment the absorption of cholesterol by 82% while sitosterol, respectively, inhibited absorption by 50%

Some studies have used the fatty acid esters of sitosterol, such as sitosterol acetate or oleate or stigmasterol the oleate dissolved in fats. In experiments on rats "oil" of this kind, having a concentration of Sterol up to 8% reduces the absorption of cholesterol by 20-40% [22] When vysokochastotnoi diet (500 mg/day) the sitosterol oleate (2 g/day) dissolved in fat, reduces the absorption of cholesterol in subjects subjects on average 33% [25] In the same study, mixed with food sitosterol in a lower dose (1 g/day) reduced the absorption of cholesterol by 42%

Patent of Germany (Deutsches Patentamt, Offenlengungsschrift 2035069, January 28, 1971) refers to the addition of fatty acid esters of Sterol in the oil for cooking to reduce levels of serum cholesterol in humans. In this patent proposes to etherification of free sterols to use the method, in any case do not meet the requirements of preparing high quality food. According to the patent etherification conduct between the free Sterol and anhydride fatty acids when exposed perchloric acid as catalyst. The used catalyst and reagent may not be acceptable in the process of preparing a food product is>/P>Many of the reagents, which may not be acceptable as food or for food production, intended as an additive to food, were used to obtain fatty acid esters of sterols. Usually using, for example, chlorine [39] bromine [40] thionyl chloride [41] or anhydrite derivatives of fatty acids. Among the patented process only way Baltes/Deutsches Patentamt, Offenlengungsschrift 2248921, April 11, 1974 for the esterification of sterols present in oils and fats, by the method of chemical interesterification meets the criterion of cooking food. In the mentioned patent free Sterol and surplus fatty acid ester is added to a mixture of thoughts or fat, then all oily mixture praeteritorum well-known method of interesterification.

The proposal according to the present invention refers to the use of Sterol completely different kind to lower cholesterol levels in the serum. It includes esters of fatty acids 5a-saturated sterols, particularly the fatty acid esters of sitostanol (sitostanol 24-ethyl-5a-cholestan-3b-ol), which lower cholesterol in serum with special efficiency. These esters can be obtained or ispara fatty acids Cystoseira obtained by curing trading mixture of sitosterol (sitosterol 25-ethyl-5-cholesten-3b-ol). b-sitostanol can be obtained by previously known methods of curing cholesterol by curing b-sitosterol using Pd/C catalyst in an organic solvent [43] the Mixture was approved by the FDA (Cytellin, Eli, Lilly). In the reaction, the degree of cure reaches 99% of the Catalyst used in the conversion, is removed using a membrane filter, and the obtained sitostanol kristallisera, washed and dried. According to the invention b-sitosterol mixture, which contains approximately 6% of campestanol, atelevision different mixtures of esters of fatty acids are widely known methods of prettification [44-46] In the reaction can be used methyl ester mixture fatty acids of any vegetable oil. One example is a mixture of rapeseed oil and methyl ester, but acceptable are fatty acids containing about 2-22 carbon atoms. The method according to the invention for obtaining fatty acid esters of stanol differs from the previously patented ways that no other substances, in addition to free stanol, ether fatty acid or mixture of fatty acid ester and the catalyst used in the interesterification reaction. The catalyst can be any known katalysatoren the invention, in contrast to the way Baltes mentioned above, the grease itself is not praeteritorum. In this case, the fat part when cooking in fat or any other food will retain its natural properties. It was necessary to note further that praeteritorum the mixture can be added directly to fat-containing products, or used as such. As scanalatura part of the mixture is not absorbed, the energy content of the mixture of fatty acid ester and stanol is only 20-40% of the energy content of conventional thoughts or fat, depending on the composition of fatty acids. Thus the mixture can successfully be used also as substance reduce the energy content of food.

Effect of fatty acid esters of b-sitosterol on the cholesterol absorption and serum cholesterol levels has not been previously investigated. In the study, which is based on this proposal examines how the concentration of plant Sterol serum depend on sitostanol, b-sitostanol 94% and campestanol 6% solid forms of sitostanol dissolved in rapeseed oil, as in (a) free and b) the form of ether fatty acids. The study design is shown in figure 1, powerup introduction rapeseed oil lasted for the entire test, other groups were administered the compound according to the invention, added to rapeseed oil.

Table. 1 shows that increasing the concentration of b-sitostanol in the diet lowers the concentration as b-sitosterol, and campesterol in the serum, but gives no clear changes in the concentration of serum b-sitostanol. The data also show that the absorption of sitostanol in a soluble form, for example in the form of esters of fatty acids, reduces the absorption of plant sterols is more effective than free b-sitostanol entered at the same dose. As fatty acid esters of b-sitostanol, it was additionally observed a clear effect of dose. This proves that b-sitostanol also inhibits the absorption of b-sitosterol and campesterol that can be seen by the decrease in their concentration.

Accordingly, there were also some changes caused by additions of stanol, concentrations of total and LDL serum cholesterol and cholesterol absorption. The control group consumed an ordinary rapeseed oil without additives stanol. Table. 2 shows that the absorption of cholesterol was significantly decreased from a mixture of ether fatty acid b-sitostanol (27,4%), even if the consumption stanol was relatively n is anola and ether fatty acid b-sitostanol on the concentration of cholesterol in serum compared with the control group shown in the table.3. The mixture of fatty acid ester of b-sitosterol lowers both total cholesterol and cholesterol more effectively than b-sitosterol. A mixture of ester of fatty acid b-sitostanol dissolved in rapeseed oil (3.2 g b-sitostanol/day) lowers total cholesterol by more than 9.5% and LDL cholesterol more than 11.6% compared with one of rapeseed oil. Accordingly, the ratio of HDL/LDL cholesterol increased significantly, from 0.32 to 0.52.

Studies clearly show that adding esters of fatty acid b-Cittanova to, for example, dietary fat, can be a significant advantage both in terms of natural nutrition, and treatment of hypercholesterinemia, because 1) the mixture reduces the levels of cholesterol in the serum, 2) the mixture does not increase the concentration of plant Sterol serum, 3) the mixture can be applied daily as a substitute of fat when cooking regular food even in large doses (0.2 to 20 g/day), and the consumption of fat is reduced.

Lipid changes caused by esters of fatty acids b-stanol noted in the research, very carefully considered from the point of view of their effect on health. The importance of the results emphasizes the prob is icnam nutrition. The research results show that during the diet with the introduction of stanol its level in the serum is not increased and that the other levels of plant sterols in serum are reduced. Thus, the mixture of ether b-stanol safe for those few individuals who can easily absorb all sterols and who have abnormalities in the secretion of sterols. Next daily replacement of fat reduces personal energy reserves, as of the effective connection of stanol was not absorbed, that is, it acts as a non-productive energy of the fat. There is no evidence that this mixture of ether b-stanol inhibits the absorption of lipid-soluble vitamins or levels of vitamins in the blood serum.

The application of a mixture of fatty acid ester of sitostanol as part of different fats or oils in the fat-containing products are extensively since the physical properties of the mixture can be easily modified by changing the fatty acid composition of the mixture. In addition, the composition of the fatty acid composition fatty acid ester b-stanol can be selected such that it contained a large number of monoenes or polyene, thanks to its effect on lowering levels of cholesterol in the reattaching the raw products, related to the regular food, and processes, mainly used in the food industry, there are no obstacles to production and use for the connection.

Example 1. A mixture of ether b-sitostanol was obtained according to the following scheme. 6 kg b-sitostanol, which was dried overnight at 60oC, atrificial 8.6 kg of a mixture of methyl ester of rapeseed oil. Pereeterifikacii carried out in the following way.

Mixture b-sitostanol and methyl ester of fatty acids of rapeseed oil is heated in the reaction vessel at 90-120oC in vacuum at 5-15 mm Hg. Drying continued for one hour, add 12 g of ateleta Na and the reaction continued for about another 2 hours the Catalyst destroy the addition to the mixture of the water. After separation of the phases molar phase is dried in vacuum.

The reaction is achieved 98% conversion. The obtained ether mixture may be used as additives to oils.

Instead of a mixture of esters of fatty acids of rapeseed oil can be used in the reaction of methyl ester or a mixture of the methyl esters of fatty acids of any vegetable oil, which contain about 2-22 carbon atoms.

Example 2. Before steam distillation of the rapeseed oil to it dobashi these fat mixture in an amount of 65%

The composition of mayonnaise following,

Fat mixture of 65.0

Thickener 2,0

Salt 1,0

Sugar 3,0

Vinegar (10 wt.) 3,0

Mustard 2,0

Water 24,0

Just 100,0

The mayonnaise was prepared by homogenization by a known method using a homogenizer Koruma.

In the preparation of mayonnaise had no trouble, and its properties are defined in terms of taste sensations, do not differ from the properties of the usual mayonnaise.

Example 3. Before steam distillation of the rapeseed oil is added a mixture of ether b-sitostanol obtained in example 1, 3 and 6 wt.

Canola oil, to which was added ether mixture is transparent at room temperature and no permanent turbidity was not observed when it was stored at low temperature.

Example 4. In the products according to examples 2 and 3 can also be used as oil other oils, such as sunflower, soybean, olive or corn.

Example 5. A mixture of ether b-sitostanol obtained in example 1, was added in amounts of 10 and 20 wt. for the fat part of the usual soft margarine (partially utverjdenie soybean oil 35, coconut oil 5, Raposa were analyzed (see table.4):

1) the mixture itself,

2) mix + 10% ether mix,

3) mix + 20% ether mixture.

Margarine, which contains 80% fat, was widely received in a known manner. Physical and sensory properties of margarine correspond to the properties of conventional Margarines.

The test for the study of the introduction given at the end of the description (figure 1).

Sources of information

1. Pollak, O. J. Reduction of blood cholesterol in man. Circulation, 7, 702-706, 1953.

2. Peterson, D. W. the Effect of soybean sterols in the diet on plasma and liver cholesterol in chicks, Pric. Soc. Exp. Biol. Med. 78, 143-147, 1951.

3. Pollak, O. J. Succesful prevention of experimental hyper-10 cholesterolemia and cholesterol atheroscleroses in the rabbit, Circulation, 7, 696-701, 1953.

4. Farquhar, J. W. and Sokolow, M. Response of serum lipids and lipoproteins of man to beta-sitosterol and safflower 15 oil A long term study. Circulation, 17, 890, 1956.

5. Grundy, S. M., Ahrens, E. H. Jr. and Davignon, J. The interaction of cholesterol absorption and cholesterol synthesis in man, J. Lipid Res. 10, 304, 1969.

6. Oster, P. Schlierf.G. Heuck, C. C. Greten, H. Gundert-Remy, U. Haase, W. Klose, G. Nothelfer, A. Raetzer, H. Schellenberg, B. und Schmidt-Gayk, H. Sitosterin bei familiare.n Hyperlipoproteinamie Typ II. Eine 25 randomisierte gekreuzte Doppelblindstudie, Dtsch. Med. Wschr. 101, 1308-1311, 1976.

7. Grundy, S. M. Dietary and drug regulation of cholesterol metabolism in man, pp. 127-159 in Lipid Pharmacology, Vol II, Eds: Paoletti, R and Glueck, C. J. Academic Press, New York, 1976.

8. Lees, A. M. Mok, H. Y. I. McCluskey, M. A. Grundy, S. M. Plant sterols as cholesterol lowering agents: clinical 35 tritosterin bei Hypercholesterinemien der Typen und II A II B, Munch. Med. Wschr. 120, 1575, 1969.

10. Tilvis, R. S. Miettinen, T. A. Serum plant sterols and their relation to cholesterol absorption. Am. J. Clin. Nutr. 43, 92-97, 1986.

11. Miettinen, T. A. Tilvis, R. S. Kesaniemi, Y. A. Serum plant sterols and cholesterol precursors reflect cholesterol absorption and synthesis in volunteers of a randomly selected male population, Am. J. Epidem. 131, (1), 20-31, 1990.

12. Farkkila, M. A. Tilvis, R. S. Miettinen, T. A. Regulation of plasma plant sterols levels in patients with gut resections, Scand. J. Clin. Lab. Invest. 48, 715-722, 1988.

13. Grundy, S. M. Mok, H. Y. I. Effects of low dose phyto-sterols on cholesterol absorption in man, pp. 112-118 in "Lipoprotein metabolism". Ed. Greten, H. Berlin, Heidelberg, New York: Springer-Verlag, 1976.

14. Kudchodkar, B. J. Horlick, L. Sodhi, H. S. Effects of plant sterols on cholesterol metabolism in man, Atherosclerosis, 23, 239, 1976.

15. lkeda, l. Tanaka, K. Sugano, M. Vahouny, G. V. Gallo l. L. Inhibition of cholesterol absorption in rats by plant sterols, J. Lipid Res. 29, 1573-1582, 1988.

16. Ikeda, l. Tanaka, K. Sugano, M. Vahouny, G. V. Gallo,

l. L. Discrimination between cholesterol and sitosterol for absorption in rats, J. Lipid Res. 29, 1583-1592, 1988.

17. Ikeda, l. Tanabe, Y. and Sugano, M. Effects of sitosterol and sitostanol on micellar solubility of cholesterol, J. Nutr. Sci. Vitaminol. 35, 361-369, 1989.

18. Ikeda, l. Sugano, M. Comparison of absorption and metabolism of beta-sitosterol and beta-sitostanol in rats, Atherosclerosis, 30, 227, 1978.

19. Sugano, M. Marioka, H. and Ikeda, l. A comparison of hypocholesterolemic activity of beta-sitosterol and beta-sitostanol in rats. J Nutr. 107, 2011-2019, 1977.

20. Heinemann, T. Leiss, O. von Bergman, K. Effects of low-dose sitostanol on serum cholesterol in patients with hypercholesterolemia, Atherosclerosis, 61, 219-223, 1986.

21. Lees, R. S. Lees, A. Mptx2">

22. Mattson, F. H. Volpenhein, R. A. and Erickson, B. A. Effect of plant sterol esters on the absorption of dietary cholesterol, J. Nutr. 107, 1139-1146, 1977.

23. Heinemann, T. Pietruck, B. Kullak-Ublick, G. von Bergman, K. Comparison of sitosterol and sitostanol on inhibition of intestinal cholesterol absorpiton. Agents Actions (Suppi), 26, 117-122, 1988.

24. Heinemann, T. Kullak-Ublick, G.-K. Pietruck, B. von Bergmann, K. Mechanisms of action of plant sterols on inhibition of cholesterol absorption, Eur. J. Clin. Pharmacol. 40 Suppi. l S50-S63, 1991.

25. Mattson, F. H. Grundy, S. M. Grouse, J. R. Optimizing the effect of plant sterols on cholesterol absorption in man. Am. J. Clin. Nutr. 35, 697-700, 1982.

26. Kesaniemi, Y. A. Ehnholm, C. Miettinen, T. A. Intestinal cholesterol absorption efficiency in man is related to apoprotein E phenotype, J. Clin. Invest. 80, 578-581, 1987.

27. Kesaniemi, Y. A. Miettinen, T. A. Metabolic epidemiology of plasma cholesterol, Ann. Clin. Res. 20, 26-31, 1988.

28. Ehnholm, C. et al. Apolipoprotein polymorphism in the Finnish population: gene frequencies and relation to lipoprotein concentrations, J. Lipid. Res. 27, 227-235, 1986.

29. Miettinen, T. A. Gylling, H. Vanhanen, H. Serum cholesterol response to dietary cholesterol and apoprotein E phenotype, Lancet, 2, 1261, 1988.

30. Gould, G. Absorbability of beta-sitosterol, Trans. N. Y. Acad. Sci. 2, 129, 1955.

31. Gould, R. G. Jones, R. J. LeRoy, G. W. Wissler, R. W. Taylor, C. B. Absorbability of beta-sitosterol in humans, Metabolism, 18, 652-662, 1969.

32. Salen, G. Ahrens, E. J. Grundy, S. M. Metabolism of beta-sitosterol in man, J. Clin. Invest. 49, 952-67, 1970.

33. Salen, G. Kwiterowich, P. O. Jr, Shefer, S. Tint, G. S. Horak, l. Shore, V. Dayal, B. Horak, E. Increased plasma cholestanol and 5 alpha - saturated plant sterol derivatives in subjects with sitosterolemia and xanthomatosis, J. Lipid Res. 26, 203-209, 1985.

35. Miettinen, T. A. Phytosterolemia, xanthomatosis and premature atherosclerosis desease: a case with high plant sterol absorption, impaired sterol elimination and low cholesterol synthesis, Eur. J. Clin. Invest. 10, 27-35, 1980.

36. Nikkila, K. Miettinen, T. A. Serum cholesterol precursors, cholestanol and plant sterols in PBC, Scand. J. Gastroenteri. 23, 967- 972, 1988.

37. Miettinen, T. A. Siurala, M. Bile salts, sterols, asterol esters, possesses anti-inflammatory properties and fatty acids in micellar and oil phases of intestinal contents during fat digestion in man, Z. Klin. Chem. Biochem. 9, 47-52, 1971.

38. Hassan, A. S. Rampone, A. J. Intestinal absorption and lymphatic transport of cholesterol and beta-sitostanol in the rat, J. Lipid Res. 20, 646-653, 1979.

39. Kuksis, A. Beveridge, J. M. R. J. Org. Chem, 25:1209, 1960.

40. Saroja, M. Kaimal, T. N. B. A convienent method of esterification of fatty acids. Preparation of alkyl esters, sterol esters, wax esters and trialcyiglycerols, Synthetic communications, 16, 1423-1430, 1986.

41. Prabhudesai, A. V. A simple method for the preparation of cholesteryl esters, Lipids, 12, 242-244, 1977.

42. Lentz, B. R. Barenholz, Y. Thompson, T. E. A simple method for the syntesis of cholesterol esters in high yield. Chemistry and Physics of Lipids, 15, 216-221, 1975.

43. Augustine, R. L. and Reardon Jr.E.J. The palladium catalyzed hydrogenation of cholesterol. Organic preparations and procedures 1(2), 107-109, 1969.

44. Sreenivasan, B. Interesterification of fats, J. Am. Oil Chemists' Soc. 55, 796-805, 1978.

45. Lo, Y. C. and Handel, A. P. Physical and chemical properties of randomly interesterified blends of soybean oil and tallow for use as margarine oils, J. Am. Oil Chemists' Soc. 60, 815-818, 1983.

46. Chobanov, D. Chobanova, R. Alterations in glyceride composition during interesterification of mixtures of sunflower oil with lard and tallow, J. Am. Oil Che acids or a mixture of esters of sitosterol and fatty acids2WITH22obtained by the esterification of sitostanol complex air2WITH22fatty acid or mixture of esters WITH2WITH22fatty acids in the presence of an interesterification catalyst at a temperature and a sufficient vacuum to obtain a transparent solution, where free-sitostanol completely dissolved in the above complex ester of fatty acids or mixtures of these esters of fatty acids, lowers the cholesterol level in the serum.

2. Substance under item 1, characterized in that the esterification is carried out at a temperature of from 90 to 100oWith in vacuum at 5 to 15 mm RT.article.

3. Substance on PP.1 and 2, characterized in that it is a fat-soluble form, obtained by the esterification of free-sitostanol complex ester of fatty acids or a mixture of esters of fatty acids.

4. Substance on PP.1 to 3, characterized in that it is added in the production of fat or other food products.

5. Substance on PP.1 to 3, characterized in that it is used as the main fat component or substitute fat.

6. Substance under item 5, characterized in that it is used as an additive in p is P CLASS="ptx2">

7. Substance on PP.1 to 3, characterized in that it can be used as part of a diet.

8. The method of obtaining the substance under item 1, characterized in that the free-sitostanol atrificial complex ester of fatty acids or a mixture of esters of fatty acids in the presence of an interesterification catalyst at a temperature and a sufficient vacuum to obtain a transparent solution, where free-sitostanol completely dissolved in a complex ester of fatty acids or mixtures of esters of fatty acids.

9. The method according to p. 8, characterized in that the reaction is carried out at a temperature of approximately 90 120oC and under vacuum of about 5 to 12 mm Hg.


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