WO2008010362A1 - Powder of vitamin e/proline complex and method of producing the same - Google Patents

Abstract

It is intended to find out and produce a powder which is in the form of an oil at room temperature, contains a large amount of vitamin E being fat-soluble and highly viscous, and has a high fluidity. It is found out that a powder containing a large amount of vitamin E and having a high fluidity can be obtained by blending vitamin E, proline and an organic solvent, stirring the resultant mixture at room temperature or under heating to thereby form a vitamin E/proline complex, distilling off the organic solvent and then drying.

Description

 Description: Vitamin E and proline complex powder and its manufacturing method Technical Field

 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 The present invention relates to a flowable powder and a method for producing the same. Background art

 Vitamin E, which is viscous and oily, is used for the primary prevention of coronary artery disease such as myocardial infarction (Lancet 356: 1213-1218, 2000 (Non-patent Document 1)) in human subjects. In contrast to the prevention of prostate cancer (J Natl Cancer Inst 90: 440-6, 1998 (Non-Patent Document 2)). In addition, suppression of the decline in the cognitive function of Alzheimer (Dimentia 1: 134-142, 1987 ( It is judged to be effective against non-patent literature 3)). There are many literatures that prevent diseases other than the above by taking vitamin E alone or in combination with vitamin C or zinc.

 However, vitamin E is oily at room temperature, and it is also fat-soluble and extremely viscous, so it must be devised when used in pharmaceuticals and foods.

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

Therefore, there are many patents for powdering vitamin E, such as emulsifiers, proteins such as gelatin and sodium caseinate, gums such as gum arabic, saccharides such as monosaccharides and disaccharides, sugar alcohols, saponins, modified starches and dextrins Patents for making emulsified powders by using single or complex polysaccharides (JP-A-60-0-178888-2 (Patent Document 1), JP-A-6-1-6001 No. 9 (Patent Document 2), JP-A-6 4-6 6 1 4 17 (Patent Document 3), JP-A 8-14 3 45 6 (Patent Document 4), JP-A-10 10 — 1 2 7 2 5 8 (Patent Document 5), Japanese Patent Laid-Open No. 1 1-1 9 3 No. 229 (Patent Document 6), JP-A 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 the disadvantage that it is difficult to obtain a powder containing a high amount of vitamin E, and that the fluidity of the powder becomes very poor when the content is high.

 Patent Document 1 Japanese Patent Application Laid-Open No. Sho 60-1 78 8 82

 Patent Document 2 Japanese Patent Application Laid-Open No. Sho 6 1 1 6 06 1 9

 Patent Document 3 Japanese Patent Application Laid-Open No. 64-6 14 1 7

 Patent Document 4 Japanese Patent Application Laid-Open No. 8-1 4 34 5 6

 Patent Document 5 Japanese Patent Application Laid-Open No. 1 0-1 27 2 58

 Patent Document 6 Japanese Patent Laid-Open No. 1 1 1 1 93 2 29

 Patent Document 7 Japanese Unexamined Patent Publication No. 2000-24 7 86 9

 Patent Document 8 Japanese Unexamined Patent Application Publication No. 2004-75 600

 Non-Patent Document 1 Lancet ^ 5: 1213-1218, 2000

 Non-Patent Document 2 J Natl Cancer Inst 90: 440-6, 1998

 Non-Patent Document 3 Dimentia 1; 134-142, 1987 Disclosure of the Invention

 An object of the present invention is to find and produce vitamin E that is oily at room temperature, fat-soluble and extremely viscous, and that has a high vitamin E content and good fluidity. As a result of intensive studies in order to achieve the above-mentioned problems, the present inventor formed a complex of vitamin E and proline by mixing vitamin E, proline and an organic solvent and stirring at room temperature to heating. The present inventors have found that a powder having a high vitamin E content and good fluidity can be obtained by distilling off the organic solvent and drying, thereby completing the present invention.

 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 weight ratio of proline to vitamin E is 1: 0.27 ~: 1: 0.67 (1) The vitamin E-containing powder according to (1),

 (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, the organic solvent is distilled off and dried.

 (4) The method for producing a vitamin E-containing powder according to (3), wherein the weight ratio of proline to vitamin E is 1: 0.27 to 1: 0.67

It is about.

 When the present inventor studied to select one of the food additives as a substance to be mixed with vitamin E when powdering vitamin E, it was determined that amino acids are preferable.

 However, as a result of repeated experiments with various 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 or purified from soybean or rapeseed seeds or palm oil, or synthetic vitamin E. d- _α- tocopheronole, d-j8-tocopheronole, d _ γ — Tocopheronole, d— δ — Tocopheronole, d— α— Tocotrienore, d— j3 _ Tocotrienole, d— One Tocotrieno One, d— δ — Toco Trieno One and d 1 — A mixture of 1 or 2 of 1 Tokofue mouths. 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. General properties include a structure with a heterocycle, weak sweetness, physiological activity such as lipolytic enzyme lipase activation, collagen synthesis promoting activity and epidermal cell growth promoting activity, and immediate effect Energy source.

 The ratio of vitamin E and proline is Vitamin E: proline = 1 in weight conversion.

1-1: 10 is preferable, 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 the weight of vitamin E is 1 and proline is lower than 0.27 in terms of weight, the powder The fluidity of When vitamin E is 1 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 dissolve 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. Vitamin E, proline, and ethanol are placed in a tank equipped with a heating or heating device and stirred for a specified time while heating. After that, the ethanol is distilled off and then dried. Ethanol is distilled off using a general apparatus such as a distillation or vacuum distillation apparatus, and powder is dried 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 effective in the primary prevention of coronary artery disease such as myocardial infarction, prevention of prostate cancer, and suppression of decline in Alzheimer's cognitive function. Can be used for expected usage.

This specification includes the contents described in the specification and ^/ or drawings of Japanese Patent Application No. 2006-195602, which is the basis of the priority of the present application. Brief Description of Drawings

 Figure 1 shows a powder consisting of a complex of vitamin E and proline. BEST MODE FOR CARRYING OUT THE INVENTION

 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.

Example 1 Vitamin E (trade name: d-α-tocopherol Tama Seikagaku Co., Ltd.) 5 g, proline (trade name: L (1) monoproline Wako Pure Chemical Industries, Ltd.) 5 g, 180 ml of ethanol was weighed into an eggplant-shaped flask and heated at 75 ° C. for 3 hours. Subsequently, ethanol was distilled off under reduced pressure and then dried 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%.

Example 2

 Vitamin E (trade name: d—α-tocopherol, manufactured by Tama Seikagaku) 6 g, proline (trade name: L (1) —proline, manufactured by Wako Pure Chemical Industries, Ltd.) 4 g, 150 ml of ethanol was weighed into an eggplant flask and heated at 75 ° C for 3 hours. Subsequently, ethanol was distilled off under reduced pressure and then dried 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%.

Example 3

 Vitamin E (trade name: d— α-tocopherol Tama Seikagaku Co., Ltd.) 7 g, proline (trade name: L (1) monoproline, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g, 100 ml of ethanol was weighed into an eggplant flask and heated at 75 ° C. for 3 hours. Subsequently, ethanol was distilled off under reduced pressure and then dried 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%.

Example 4

Vitamin E (trade name: d-α-tocopherol Tama Seikagaku Co., Ltd.) 7.8 g, proline (trade name: L (1) monoproline Wako Pure Chemical Industries, Ltd. ) 2.2 g of ethanol 10 O m 1 was 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 pale yellow powder (FIG. 1). In this example, the ratio of vitamin E to proline is 1: 0.28 and the content of vitamin E is 78. /. Met.

[Comparative Example 1]

 Vitamin E (trade name: d— α-tocofol roll manufactured by Tama Seikagaku Co., Ltd.) 9.1 g, proline (trade name: L (1) monoproline, manufactured by Wako Pure Chemical Industries, Ltd.) ) 0.9 g of ethanol 5 O m 1 was 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 pale yellow powder, but the fluidity of the powder was not good.

 In this comparative example, the ratio of vitamin E to proline was 1: 0.099, and the content of vitamin E was 91%. Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Vitamin E (g) 5 6 7 7.8 9.1 Proline (g) 5 4 3 2.2 0.9 Ethanol (ml) 180 150 100 100 50

 White to light

2, Les =. 龄, Tou 白色 white power Light White to light White to light White to light

 After leaving Ta 'yellow powder yellow powder yellow powder yellow powder

^Λ¾ . Became. Became. Became. ^ ^b

 And † this.

 [Comparative Example 2]

 According to the formulation in Table 2, the same operation as in Example 3 was performed except that proline was replaced with 3 g of glycine, which is the same amino acid (trade name: glycine manufactured by Wako Pure Chemical Industries, Ltd.). did not become.

[Comparative Examples 3 to 16]

 According to the formulation in Table 2, proline is the same amino acid L-alanine (trade name: L

—Alalanine Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 3), or 4-aminobutyric acid (trade name: 4 Iminobuty products Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 4), or L-Serine (trade name: L-serine, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 5), or L Iparin (product name: L-parin, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g ( Comparative Example 6) or L-Threonine (trade name: L-Suleon, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example

7), or L-Sistine (Product name: L-Sistine Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 8), or L Ichiguchi Ishin (trade name: L Ichiguchi Ishin, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 9), or L-Lasparagin (product name: L-Isragin Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 1 0), or L monolysine (trade name: L monolysine Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 1 1), or L monoglutamic acid

(Product name: L-Glutamic acid, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 1 2) or L-histidine (Product name: L-histidine, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g ( Comparative Example 1 3), or L (1) One Fualarayun (trade name: L (1) One Ferrara Yun Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 14), or L (+) —Arginine

(Product name: L (+) —Arginine Wako Pure Chemical Industries, Ltd.) 3 g (Comparative Example 15) or L-tyrosine (Product name: L-tyrosine, Wako Pure Chemical Industries, Ltd.) 3 g The same operation as in Example 3 was performed except that (Comparative Example 16) was used, but none of the powders became powder.

 [Comparative Examples 1 7, 1 8]

 According to the composition of Table 2, proline is the same amino acid L-tributofan (trade name: L-tributophane manufactured by Wako Pure Chemical Industries, Ltd.) 4 g (comparative example 1 7), or L-cystine (trade name: L Iscystine Wako Pure Chemical Industries, Ltd.) 4 g (Comparative Example 1 8) The procedure was the same as in Example 2 except that the powder was not changed into powder.

Table 2

Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 Vitamin E (g) 7 7 7 7 7 Glycine 3)

L-alanine (g) ― 3 ― ― ―

4-aminobutyric acid (g) ― One 3 — One

L-Serine (g) ― ― 1 3 ―

L-linoline (g) ― ― 1 3 Ethanol (ml) 100 100 100 100 100 Ethanol was distilled off. State after drying Vitamin E and the amino acid were mixed and oily.

 Comparative Example 7 Comparative Example 8 Comparative Example 9 Comparative Example 10 Comparative Example 11 Vitamin E (g) 7 7 7 7 7

L One thread Nin (g) 3 1 — 1 1

L—Sistine (g) ― 3 One — One

L bite Ishin (g) ― ― 3 — One

L-asparagine (g) ― ― 1 3 ―

L-lysine (g) ― ― 1 3 Ethanol (ml) 100 100 100 100 100 Ethanol distilled off · State after drying Vitamin E and the amino acid were mixed and oily.

 Comparative Example 12 Comparative Example 13 Comparative Example 14 Comparative Example 15 Comparative Example 16 Vitamin E (g) 7 7 7 7 7

L—Glutamic acid (g) 3 — — — —

L-histidine (g) ― 3 — — —

L (―) One Fualanine (g) ― ― 3--

L (+) —Arginine (g) ― ―-3-

L-tyrosine (g) ― ― 1 3 Ethanol (ml) 100 100 100 100 100 Ethanol was distilled off · State after drying Vitamin E and the amino acid were mixed and oily.

 Comparative Example 17 Comparative Example 18

Vitamin E ( _g ) 6 6

 L tribute fan (g). 4 ―

 L-cystine (g) ― 4

Ethanore (ml) 150 150

Ethanol was distilled off. 'Dry state after drying' Vitamin E and the amino acid were mixed and oily. Instead of proline, it was tested whether 17 amino acids listed in Table 2 could form a complex with vitamin E. However, in any experiment, it was not possible to make a powder. E and proline were found to form a complex specifically into a powder.

[Experiment 1]

 Using the powder obtained in Example 4, measurement of physical properties such as vitamin E content in powder, repose angle, bulk density, tapping density and melting point was performed.

The measurement method of vitamin E content in powder is 40 times the amount of powder (VZW) Distribute with 50 vo 1% ethanol water and 20 times the amount of hexane (V / W), and evaporate the hexane to dry out to obtain a viscous oil. Powder that uses the amount of vitamin E obtained by quantifying the vitamin E content by the method described in the 7th edition and extracting the powder multiplied by the vitamin E content in the extracted oil. The value obtained by dividing the quantity by the 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 characteristic measuring instrument (manufactured by Tsutsui Chemical Co., Ltd.). The results are shown in Table 3. .

 The melting point of the powder is MI CRO MELT I NG PO I NT AP PARATU

Measurements were made using S (manufactured by Yanagimoto Seisakusho), and the results are shown in Table 3.

 Table 3

 Example 4 powder

Vitamin E content in powder (%) 78

Angle of repose (°) 39

Bulk density (gZml) 0.44

Tapping density (g / ml) 0.53

Melting point (° C) 63 ~ 65

 From the results in 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 gZm 1, a tapping density of 0.53 g Zm 1 and a melting point. It can be seen that the powder has a high vitamin E content and good fluidity at 63 to 65 ° C. Industrial applicability

 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.

 All publications, patents and patent applications cited herein are incorporated herein by reference in their entirety.

Claims

The scope of the claims 1. 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 claim 1, wherein the weight ratio of proline to vitamin E is from 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 method for producing a vitamin E-containing powder according to claim 3, wherein the weight ratio of proline to vitamin E is from 1: 0.27 to 1: 0.67.