JP2008024603A - Complex powder of vitamin e and proline and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain vitamin E that is oily at a normal temperature, lipid-soluble and has extremely high viscosity as powder having a high vitamin E content and excellent fluidity. <P>SOLUTION: Vitamin E is mixed with proline and an organic solvent, stirred at a room temperature or under heating to form a complex of vitamin E and proline, the organic solvent is distilling away and the complex is dried to give powder having a high vitamin E content and excellent fluidity. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  In the present invention, vitamin E and proline are stirred in an organic solvent to form a complex of vitamin E and proline, and the organic solvent is distilled off and dried to obtain a high vitamin E content and fluidity. The present invention relates to a good powder and a method for producing the same.

  Vitamin E, which is viscous and oily, is used for primary prevention of coronary artery disease such as myocardial infarction (Lancet 356: 1213-1218, 2000 (Non-Patent Document 1)) in human subjects. For prevention of prostate cancer (J Natl Cancer Inst 90: 440-6,1998 (Non-Patent Document 2)) and further suppression of decline in Alzheimer's cognitive function (Dimentia 1: 134-142,1987 (Non-Patent Document 2) 3)) is determined to be effective. There are a number of documents that have a preventive effect on diseases other than those mentioned above by ingesting vitamin E alone or in combination with vitamin C or zinc.

  However, vitamin E is oily at room temperature, and is fat-soluble and extremely viscous.

  An example is changing the form of vitamin E into powder, and by making it into powder, it can be easily mixed uniformly into pharmaceuticals and food materials, and is an extremely effective method for processing into products. is there.

  Therefore, there are many patents for powdering vitamin E, such as emulsifiers, proteins such as gelatin and sodium casein, gums such as gum arabic, saccharides such as monosaccharides and disaccharides, sugar alcohols, saponins, modified starches and dextrins, etc. Patents to make an emulsified powder by using these polysaccharides alone or in combination (Japanese Patent Application Laid-Open No. 60-178882 (Patent Document 1), Japanese Patent Application Laid-Open No. 61-60619 (Patent Document 2), Japanese Patent Application Laid-Open No. JP-A-61417 (Patent Document 3), JP-A-8-143456 (Patent Document 4), JP-A-10-127258 (Patent Document 5), JP-A-11-193229 (Patent Document 6), JP 2000-247869 (Patent Document 7), JP-A-2004-75600 (Patent Document 8)) and the like have been reported.

  However, any of the methods using emulsified powder has a drawback that it is difficult to obtain a powder containing a high amount of vitamin E, and further, the fluidity of the powder becomes very poor when the content is high.

Japanese Unexamined Patent Publication No. 60-178882 Japanese Patent Laid-Open No. 61-60619 JP-A-64-61417 JP-A-8-143456 Japanese Patent Laid-Open No. 10-127258 JP 11-193229 A JP 2000-247869 A JP 2004-75600 A Lancet 356: 1213-1218,2000 J Natl Cancer Inst 90: 440-6,1998 Dimentia 1: 134-142,1987

  An object of the present invention is to find and produce a vitamin E that is oily at room temperature, is fat-soluble and has extremely high viscosity, and has a high vitamin E content and good fluidity.

  As a result of intensive studies to achieve the above-mentioned problems, the present inventor blended vitamin E, proline and an organic solvent, and formed a complex of vitamin E and proline by stirring while stirring at room temperature or heating, By distilling off the organic solvent and drying, it was found that the powder had high vitamin E content and good fluidity, and the present invention was completed.

That is, the present invention
(1) A vitamin E-containing powder obtained by forming a complex by stirring vitamin E and proline in an organic solvent, distilling off the organic solvent and drying;
(2) The vitamin E-containing powder according to (1), wherein the weight ratio of proline to vitamin E is 1: 0.27 to 1: 0.67,
(3) A method for producing a vitamin E-containing powder characterized in that a complex is formed by stirring vitamin E and proline in an organic solvent, and the organic solvent is distilled off and dried.
(4) The weight ratio of proline to vitamin E is 1: 0.27 to 1: 0.67, and relates to the method for producing a vitamin E-containing powder according to (3).

  When the present inventor studied to select one kind of food additive as a substance to be mixed with vitamin E in powdering vitamin E, it was determined that an amino acid is preferable.

  However, as a result of repeating various experiments in a variety of amino acids, it was found that only proline can be powdered, and the present invention was completed.

  Vitamin E used in the present invention is natural vitamin E extracted from seeds such as soybean and rapeseed or palm oil or synthetic vitamin E, and is d-α-tocopherol, d-β-tocopherol, d-γ-tocopherol. , D-δ-tocopherol, d-α-tocotrienol, d-β-tocotrienol, d-γ-tocotrienol, d-δ-tocotrienol and dl-α-tocopherol. The vitamin E is oily at room temperature, and is fat-soluble and extremely viscous.

  Proline used in the present invention is one of 20 amino acids that are constituents of proteins that form the human body, and is a major component of collagen that constitutes the skin and the like. A general property is a structure having a heterocyclic ring, which exhibits weak sweetness, exhibits physiological activities such as lipolytic enzyme lipase activation, collagen synthesis promoting activity and epidermal cell proliferation promoting activity, and also has an immediate effect. It becomes an energy source.

  The ratio of vitamin E to proline is preferably vitamin E: proline = 1: 0.1 to 1:10 in terms of weight, more preferably vitamin E: proline = 1: 0.27 to 1: 0. 67. The object of the present invention is to obtain a powder having a high vitamin E content and good fluidity. When vitamin E is 1 and proline is lower than 0.27 in terms of weight, When the fluidity is deteriorated and vitamin E is 1 in weight conversion and proline is higher than 0.67, the content of vitamin E decreases.

  The organic solvent used in the present invention is alcohols such as methanol, ethanol, propanol and butanol, and any of them can be used as long as it dissolves vitamin E and proline. It is preferable to use ethanol.

  The amount of ethanol is preferably 10 times the amount (V / W) or more of the amount of vitamin E and proline charged.

  The powder having high vitamin E content and good fluidity of the present invention can be produced by the method described below, but is not limited thereto. A predetermined amount of vitamin E, proline and ethanol are put into a tank equipped with a heating or heating device and stirred for a predetermined time while heating, and then ethanol is distilled off and then dried. Evaporation of ethanol should be performed using a general apparatus such as distillation or vacuum distillation apparatus, and powder drying should be performed using a general apparatus such as spray drying, drum drying, belt drying or freeze dryer. Can do.

  The powder thus obtained has a high vitamin E content and good powder flowability. This powder is expected to have physiological functions because vitamin E is effective for primary prevention of coronary artery disease such as myocardial infarction, prevention of prostate cancer, and suppression of decline in Alzheimer's cognitive function. It can be adopted for the usage method.

  According to the present invention, a powder having a high vitamin E content and good fluidity can be produced, and a powder suitable for production of pharmaceuticals and foods can be obtained.

  Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited thereto.

  According to the composition in Table 1, 5 g of vitamin E (trade name: d-α-tocopherol manufactured by Tama Seikagaku Co., Ltd.), 5 g of proline (trade name: L (−)-proline, manufactured by Wako Pure Chemical Industries, Ltd.), 180 ml of ethanol was weighed into an eggplant type flask and heated at 75 ° C. for 3 hours. Subsequently, ethanol was distilled off under reduced pressure, followed by drying under reduced pressure to obtain 10 g of white to light yellow powder.

  In this example, the ratio of vitamin E to proline was 1: 1, and the content of vitamin E was 50%.

  According to the composition of Table 1, vitamin E (trade name: d-α-tocopherol manufactured by Tama Biochemical Co., Ltd.) 6 g, proline (trade name: L (−)-proline manufactured by Wako Pure Chemical Industries, Ltd.) 4 g, 150 ml of ethanol was weighed into an eggplant type flask and heated at 75 ° C. for 3 hours. Subsequently, ethanol was distilled off under reduced pressure, followed by drying under reduced pressure to obtain 10 g of white to light yellow powder.

  In this example, the ratio of vitamin E to proline was 1: 0.67, and the content of vitamin E was 60%.

  According to the composition of Table 1, vitamin E (trade name: d-α-tocopherol manufactured by Tama Biochemical Co., Ltd.) 7 g, proline (trade name: L (−)-proline manufactured by Wako Pure Chemical Industries, Ltd.) 3 g, 100 ml of ethanol was weighed into an eggplant type flask and heated at 75 ° C. for 3 hours. Subsequently, ethanol was distilled off under reduced pressure, followed by drying under reduced pressure to obtain 10 g of white to light yellow powder.

  In this example, the ratio of vitamin E to proline was 1: 0.43, and the content of vitamin E was 70%.

  7.8 g of vitamin E (trade name: d-α-tocopherol Tama Seikagaku Co., Ltd.), proline (trade name: L (-)-proline, manufactured by Wako Pure Chemical Industries, Ltd.) 2.2 g and 100 ml of ethanol were weighed into an eggplant type flask and heated at 75 ° C. for 3 hours. Next, ethanol was distilled off under reduced pressure and then dried under reduced pressure to obtain 10 g of white to light yellow powder (FIG. 1).

  In this example, the ratio of vitamin E to proline was 1: 0.28, and the content of vitamin E was 78%.

[Comparative Example 1]
According to the composition of Table 1, 9.1 g of vitamin E (trade name: d-α-tocopherol manufactured by Tama Seikagaku Co., Ltd.), proline (trade name: L (−)-proline, manufactured by Wako Pure Chemical Industries, Ltd.) 0.9 g and 50 ml of ethanol were weighed into an eggplant type flask and heated at 75 ° C. for 3 hours. Next, ethanol was distilled off under reduced pressure, and then dried under reduced pressure to obtain 10 g of white to light yellow powder, but the fluidity of the powder was not good.

  In this comparative example, the ratio of vitamin E and proline was 1: 0.099, and the content of vitamin E was 91%.

[Comparative Example 2]
According to the composition in Table 2, the same operation as in Example 3 was performed except that proline was replaced with 3 g of glycine (trade name: glycine, manufactured by Wako Pure Chemical Industries, Ltd.), which is the same amino acid. It was.

[Comparative Examples 3 to 16]
According to the composition of Table 2, 3 g of L-alanine (trade name: L-alanine manufactured by Wako Pure Chemical Industries, Ltd.), which is the same amino acid as proline, (comparative example 3), or 4-aminobutyric acid (trade name: 4- Aminodairy product Wako Pure Chemical Industries, Ltd. 3 g (Comparative Example 4), or L-serine (trade name: L-Serine Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 5), or L-valine (Trade name: L-valine manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 6), or L-threonine (trade name: L-threonine manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 7), Alternatively, L-cysteine (trade name: L-cysteine manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 8), or L-leucine (trade name: L-leucine manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (comparative) Example 9) or L-asparagine (trade name: L-asparagine, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 1) ) Or L-lysine (trade name: L-lysine, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 11), or L-glutamic acid (trade name: L-glutamic acid, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 12) or L-histidine (trade name: L-histidine, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 13), or L (-)-phenylalanine (trade name: L (-)-phenylalanine Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 14), or L (+)-Arginine (trade name: L (+)-Arginine, Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 15), or The same operation as in Example 3 was performed except that 3 g of L-tyrosine (trade name: L-tyrosine, manufactured by Wako Pure Chemical Industries, Ltd.) (Comparative Example 16) was used, but none of the powders became powder.

[Comparative Examples 17 and 18]
According to the composition of Table 2, 4 g of L-tryptophan (trade name: L-tryptophan, manufactured by Wako Pure Chemical Industries, Ltd.) which is the same amino acid as proline (Comparative Example 17), or L-cystine (trade name: L-cystine) The same operation as in Example 2 was performed except that 4 g (Comparative Example 18) was changed to 4 g (Comparative Example 18) manufactured by Wako Pure Chemical Industries, Ltd.

  An experiment was conducted to determine whether a complex with vitamin E could be formed using 17 kinds of amino acids listed in Table 2, instead of proline. And proline were found to form a complex specifically into a powder.

[Experiment 1]
Using the powder obtained in Example 4, the vitamin E content in the powder was measured, and the physical properties such as the angle of repose, the bulk density, the tapping density and the melting point were measured.

  The method for measuring the vitamin E content contained in the powder is to use 40 volumes (V / W) of 50 vol% ethanol water and 20 volumes (V / W) of hexane for the powder. Since a viscous oil is obtained when dried and dried, the vitamin E content of this oil is quantified by the method described in the 7th edition of the Food Additives Standard, and the amount of oil obtained by extracting the powder is extracted into the extracted oil. The value obtained by multiplying the amount of vitamin E obtained by multiplying the amount of vitamin E by the amount of powder used at the time of extraction as a percentage is the vitamin E content in the powder. The results are shown in Table 3.

  Furthermore, in order to investigate the fluidity of the powder, the angle of repose, the bulk density, and the tapping density were measured using an ABD powder property measuring instrument (manufactured by Tsutsui Chemical Co., Ltd.), and the results are shown in Table 3.

  The melting point of the powder was measured using MICRO MELTING POINT APPARATUS (manufactured by Yanagimoto Seisakusho Co., Ltd.), and the results are shown in Table 3.

  From the results of Table 3, the powder of the present invention of Example 4 has a vitamin E content of 78%, an angle of repose of 39 °, a bulk density of 0.44 g / ml, a tapping density of 0.53 g / ml, and a melting point of 63. It can be seen that the powder is ˜65 ° C., has a high vitamin E content, and has good fluidity.

The figure which shows the powder which consists of a composite_body | complex of vitamin E and proline.

Claims (4)

  Vitamin E-containing powder obtained by forming a complex by stirring vitamin E and proline in an organic solvent, distilling off the organic solvent and drying.   The vitamin E-containing powder according to claim 1, wherein the weight ratio of proline to vitamin E is 1: 0.27 to 1: 0.67.   A method for producing a vitamin E-containing powder, wherein a complex is formed by stirring vitamin E and proline in an organic solvent, and the organic solvent is distilled off and dried.   The method for producing a vitamin E-containing powder according to claim 3, wherein the weight ratio of proline to vitamin E is 1: 0.27 to 1: 0.67.

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