JP2007016000A - Thioctic acid-containing composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a thioctic acid-containing composition capable of simply solubilizing thioctic acid in water or a hydrophilic material, without causing precipitation, nor separation, of the thioctic acid, even when stored for a long period, and having high stability. <P>SOLUTION: This thioctic acid-containing composition comprises the thioctic acid and an emulsifying agent having a HLB of ≥9. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a thioctic acid-containing composition that is easily solubilized and dispersed when added to water and has high storage stability.

  Thioctic acid is also called α-lipoic acid, Lipoic acid, 6,8-Thioctic acid, and the like, and is used for various pharmaceuticals including type II diabetes therapeutic drugs due to its specific physiological action. In Japan, it is possible to use it for food applications due to the review of the food category, and it is expected to be applied in the food and drink field. In addition, thioctic acid has been studied variously both in Japan and overseas, including the antioxidant properties of thioctic acid itself, and the regeneration function of vitamin C and vitamin E, which are widely known as antioxidants, It has been reported that glutathione, which is known to be involved in immunity and detoxification, is a compound with various functionalities such as the ability to increase intracellularity of glutathione. From these points, it is useful to improve the added value of food and drink. It is expected to be a new material. However, thioctic acid dissolves easily in organic solvents, but it is a compound that is usually very difficult to dissolve in water as it is, so it is very low in versatility for use in food applications, especially for beverage applications. Had the disadvantage of being severely restricted.

  Therefore, in applying thioctic acid having various functions and properties as described above to foods and drinks, adding thioctic acid powder as it is to foods and drinks, phenomena such as coalescence and heterogeneous dispersion are recognized, Since the value of processed foods and drinks is lost, it is indispensable to uniformly disperse thioctic acid in water.

  The most commonly performed method is considered to add an emulsifier and bring the thioctic acid into an emulsified state by physical action of an emulsifier or the like. However, this method has limitations and is not necessarily a general-purpose method. As long as a special device called an emulsifier is required, the use of the emulsifier becomes impossible when the viscosity of the dispersion medium is high. Furthermore, when the particle size of thioctic acid in the obtained emulsion is large or the particle size distribution is uneven, thioctic acid causes coalescence and separates from the dispersion medium, It will lose its value.

  As an attempt to make α-lipoic acid aqueous, a preparation using sulfite has been proposed. (For example, refer to Patent Document 1) However, this method has been difficult to apply to food.

  In contrast to the current situation, there is a method in which a preparation in which thioctic acid is dissolved in a soluble solvent and an emulsifier are mixed in advance and a preparation that is easily dispersed when added to water is prepared in advance. Conceivable.

  However, it has been pointed out as a problem that even in these methods, the preparation itself in which thioctic acid and an emulsifier are mixed is unstable, so that thioctic acid is separated during storage and does not become solubilized even when added to water. ing. Therefore, a preparation of thioctic acid must be prepared at the time of use, which is a great limitation in use.

JP2005-2096

  The present invention has been made in view of the above prior art, and can easily solubilize thioctic acid in water or a hydrophilic material, and is highly stable without precipitation or separation of thioctic acid even after long-term storage. It is an object to provide a thioctic acid-containing composition having properties.

  As a result of intensive studies to solve the above problems, the present inventors have found that a thioctic acid-containing composition comprising an thioctic acid and an emulsifier having an HLB of 9 or more can be easily solubilized and dispersed in water, and can be stored stably It was found that it is excellent in performance.

  The present invention is described in detail below.

  The thioctic acid-containing composition referred to in the present invention contains thioctic acid, is uniformly dispersed in water in a solubilized state, and has high storage stability. Solubilization is a state in which the particle diameter dispersed in water is usually 300 nm or less, preferably 100 nm or less, and almost transparent.

  Examples of the thioctic acid used in the present invention include generally used industrial synthetic products and extracts derived from natural ingredients, and these can be used alone or in combination. The purity is not particularly limited, but in order to achieve the present invention, it is desirable that the purity is 50% or more, preferably 70% or more, more preferably 90% or more.

  The emulsifier used in the present invention is a general term for compounds having a hydrophilic group and a lipophilic group in the same molecule, and is desirably hydrophilic. The degree of hydrophilicity and lipophilicity of the emulsifier is represented by HLB (Hydrophilic Lipophilic Balance), and in order to achieve the object of the present invention, it is desirable that it is HLB 9 or more, preferably 12 or more, more preferably 14 or more. If the HLB is smaller than 9, the thioctic acid cannot be finely dispersed in water, resulting in poor stability. The method for obtaining the HLB is not particularly limited, and various existing methods can be used. For example, in the case of an ester type emulsifier, it can be calculated from the saponification value and the acid value of the constituent fatty acid by the following formula.

HLB = 20 × (1-S / A)
S: Saponification value, A: Acid value of constituent fatty acid

  General emulsifiers with an HLB of 9 or more include synthetic emulsifiers such as polyglycerin fatty acid esters, sucrose fatty acid esters, sodium stearoyl lactate, calcium stearoyl lactate, polyoxyethylene derivatives, fatty acid salts, as well as enzymatically decomposed lecithin and hydrogenated enzymatic degradation. Lecithin derivatives obtained by chemical or enzymatic treatment of naturally occurring lecithins such as lecithin, hydroxylecithin, phosphatidylglycerol, phosphatidic acid, and acetylated lecithin, natural saponins such as soybean saponin and quillaja saponin Can be mentioned. In addition, as the origin of lecithins, those derived from plants such as soybean, rice, rapeseed, safflower and those derived from animals such as egg yolk and brain can be used.

  In particular, polyglycerol fatty acid esters are suitably used in the present invention because those having properties suitable for the purpose can be obtained by changing the condensation degree of polyglycerol, the type of fatty acid, and the degree of esterification.

  In the polyglycerin fatty acid ester used in the present invention, polyglycerin is not particularly limited, but preferably, in the polyglycerin composition, the condensation degree of glycerin is tri, tetra, penta, hexa, hepta, octa, nona. The content of one kind of polyglycerol selected from Deca is desirably 35% or more, more preferably 45% or more. This composition distribution can be analyzed by gas chromatography or liquid chromatography, and in particular, it can be easily analyzed by subjecting polyglycerin to a trimethylsilylated derivative followed by gas chromatography.

  In the polyglycerin fatty acid ester used in the present invention, the fatty acid is a substance containing, as a functional group, a carboxylic acid obtained by hydrolyzing fats and oils extracted from natural animals and plants and purifying with or without separation. There is no particular limitation. Alternatively, it may be a fatty acid obtained by chemically synthesizing petroleum or the like as a raw material. Alternatively, these fatty acids may be reduced by hydrogenation or the like, condensed fatty acids obtained by condensation polymerization of fatty acids containing hydroxyl groups, or polymerized fatty acids obtained by heat polymerization of fatty acids having unsaturated bonds. Good. The selection of these fatty acids may be appropriately determined in consideration of the desired effect. Specific examples of fatty acids used in the present invention include saturated or unsaturated fatty acids having 6 to 22 carbon atoms, that is, behenic acid, stearic acid, lauric acid, myristic acid, oleic acid, isostearic acid, palmitic acid, capric acid. , Caprylic acid, caproic acid, condensed ricinoleic acid, condensed 1,2-hydroxystearic acid, erucic acid, palmitooleic acid, linoleic acid, linolenic acid, octylic acid, octanoic acid, and ricinoleic acid having a hydroxyl group in the molecule 1,2-hydroxystearic acid and condensates thereof. Among these, fatty acids having 16 to 18 carbon atoms are particularly recommended from the viewpoint of emulsion stability.

  In addition, the emulsifier used in the thioctic acid-containing composition is not limited to polyglycerin fatty acid ester and sucrose fatty acid ester, and a combination of these may be used, or one or more of other emulsifiers may be used in combination. . Examples of such emulsifiers include monoglycerin fatty acid esters, polyglycerin fatty acid esters, organic acid monoglycerides, monoglyceride derivatives, propylene glycol fatty acid esters, sorbitan fatty acid esters, sodium stearoyl lactate, lecithin, quinaya extract, etc. Excellent polyglycerin fatty acid esters, sucrose fatty acid esters, and lecithin derivatives are preferred, and polyglycerin fatty acid esters can be most suitably used.

  The sucrose fatty acid ester used in the present invention is a compound having a structure in which a fatty acid that is a lipophilic group and sucrose that is a hydrophilic group are combined. The constituent fatty acid of the sucrose fatty acid ester is a linear or branched saturated or unsaturated fatty acid having 8 to 22 carbon atoms, and may be a single product or a mixture thereof. The degree of esterification is not particularly limited, but a low degree of esterification and a high monoester content is preferable. The monoester content is preferably 85% or more, more preferably 90% or more. If the monoester content is less than 85%, precipitation or turbidity may occur during long-term storage when used in transparent or acidic foods and drinks.

  The lecithin derivative used in the present invention is obtained by chemically or enzymatically treating naturally-derived or chemically synthesized lecithins such as soybean, rice, rapeseed, safflower and egg yolk. Lecithin is a single compound or a mixture thereof having a structure in which a fatty acid residue and a phosphate residue, and choline, ethanolamine, inositol, serine and the like are bonded to a glycerin skeleton. Examples of lecithin derivatives include enzymatically decomposed lecithin, hydrogenated enzymatically decomposed lecithin, hydroxy lecithin, phosphatidylglycerol, phosphatidic acid, and acetylated lecithin.

  The method for preparing the thioctic acid-containing composition of the present invention is not particularly limited, but ethyl alcohol and / or for the purpose of improving handling properties, improving stability during water dispersion, and improving the storage stability of the composition itself. It is preferable to add a polyhydric alcohol such as propylene glycol or glycerin.

  Since the optimum ratio of the thioctic acid-containing composition changes when the respective types change, the range cannot be limited. However, the upper limit of thioctic acid is 30%, preferably 15%, and the lower limit is 1%. More preferably, the upper limit of the emulsifier having an HLB of 9 or more is 30%, preferably 10%, the lower limit is 5%, more preferably 15%, the upper limit of the alcohol is 90%, preferably 80%, and the lower limit is 50 %, More preferably 60%, the upper limit of polyhydric alcohol is 30%, preferably 15%, and the lower limit is 5%, preferably 10%. A thioctic acid-containing composition can be prepared even outside this range, but it is not preferable because stability during storage is significantly deteriorated.

  The thioctic acid-containing composition of the present invention can be used in foods and drinks and cosmetics that are desired to be easily solubilized and dispersed when added to water. In food and drink, for example, fruitless drinks, fruit drinks, vegetable drinks, lactic acid bacteria drinks, tea drinks, carbonated drinks, coffee drinks, soup drinks, alcoholic drinks, mineral drinks, vitamin drinks, drinks containing functional food ingredients, etc. Beverages, milk beverages, lactic acid bacteria beverages, fermented milk, condensed milk, concentrated milk, yogurt, ice cream, and other milk-based products, dessert foods such as jelly, bavaroa, pudding, chocolate, caramel, Examples include confectionery such as candy and snack foods, seasonings such as soup, sauce and dressing, cooked foods such as retort foods, and other instant foods.

  In cosmetics, for example, soaps, cleansings, shampoos, rinses and other cleaning products, skin lotions, emulsions, creams, packs, hair tonics, hair creams, and other basic cosmetics, set lotions, hair cosmetics and other finishing cosmetics, perfumes, Examples include fragrances such as lotions, and cosmetics used in the mouth such as dentifrices.

  Next, the present invention will be described in more detail based on examples, but the present invention is not limited only to such examples.

Example 1
Triglycerin monostearate (manufactured by Taiyo Kagaku Co., Ltd., HLB value 10, triglycerin 45% in polyglycerin composition) as an emulsifier with an HLB of 9 or more was added to 20 g of ethyl alcohol (Japan Alcohol Sales Co., Ltd.) ), 60 g of ethyl alcohol content 99% or more) and 10 g of glycerin (manufactured by NOF Corporation) as a polyhydric alcohol were added and dissolved by stirring. To this was added 10 g of thioctic acid (trade name: Lipoec, manufactured by Cognis Japan Co., Ltd., content of 99% or more) and solubilized by a stirring operation to obtain a thioctic acid-containing composition. 0.2 g of this thioctic acid-containing composition was taken, and 99.8 g of water was added to prepare a 0.2% aqueous dispersion.

Example 2
As an emulsifier with an HLB of 9 or more, 20 g of pentaglycerin monomyristate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, pentaglycerin 45% in the polyglycerin composition) ), 60 g of ethyl alcohol content 99% or more) and 10 g of glycerin (manufactured by NOF Corporation) as a polyhydric alcohol were added and dissolved by stirring. To this was added 10 g of thioctic acid (trade name: Lipoec, manufactured by Cognis Japan Co., Ltd., content of 99% or more) and solubilized by a stirring operation to obtain a thioctic acid-containing composition. 0.2 g of this thioctic acid-containing composition was taken, and 99.8 g of water was added to prepare a 0.2% aqueous dispersion.

Example 3
19.8 g of pentaglycerin monomyristate (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, 45% of pentaglycerin in polyglycerin composition) as an emulsifier with an HLB of 9 or more and DK which is a sucrose fatty acid ester Esters SS (Daiichi Kogyo Seiyaku Co., Ltd., HLB value 19.0, monoester content 95%) 0.2g, ethyl alcohol (Nihon Alcohol Sales Co., Ltd., ethyl alcohol content 99% or more) 60g and many 10 g of glycerin (manufactured by Nippon Oil & Fats Co., Ltd.) was added as a monohydric alcohol and dissolved by stirring. To this was added 10 g of thioctic acid (trade name: Lipoec, manufactured by Cognis Japan Co., Ltd., content of 99% or more) and solubilized by a stirring operation to obtain a thioctic acid-containing composition. 0.2 g of this thioctic acid-containing composition was taken, and 99.8 g of water was added to prepare a 0.2% aqueous dispersion.

Example 4
As an emulsifier having an HLB of 9 or more, 19.5 g of pentaglycerin monomyristate (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, 45% of pentaglycerin in polyglycerin composition) and enzymatically decomposed lecithin (trade name: Sun lecithin A, manufactured by Taiyo Kagaku Co., Ltd., 0.5 g of HLB value 12.0), 60 g of ethyl alcohol (manufactured by Nippon Alcohol Sales Co., Ltd., ethyl alcohol content 99% or more) and glycerin (Nippon Yushi) as polyhydric alcohol 10 g) was added and dissolved by stirring. To this was added 10 g of thioctic acid (trade name: Lipoec, manufactured by Cognis Japan Co., Ltd., content of 99% or more) and solubilized by a stirring operation to obtain a thioctic acid-containing composition. 0.2 g of this thioctic acid-containing composition was taken, and 99.8 g of water was added to prepare a 0.2% aqueous dispersion.

Comparative Example 1
As an emulsifier with an HLB of less than 9, diglycerin monostearate, a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 7, diglycerin 45% in polyglycerin composition), 20 g of ethyl alcohol (Japan Alcohol Sales Co., Ltd.) ), 60 g of ethyl alcohol content 99% or more) and 10 g of glycerin (manufactured by NOF Corporation) as a polyhydric alcohol were added and dissolved by stirring. To this was added 10 g of thioctic acid (trade name: Lipoec, manufactured by Cognis Japan Co., Ltd., content of 99% or more) and solubilized by a stirring operation to obtain a thioctic acid-containing composition. 0.2 g of this thioctic acid-containing composition was taken, and 99.8 g of water was added to prepare a 0.2% aqueous dispersion.

Comparative Example 2
Diglycerin monostearate which is a polyglycerin fatty acid ester as an emulsifier with an HLB of less than 9 (manufactured by Taiyo Kagaku Co., Ltd., HLB value 7, diglycerin 45% in the polyglycerin composition) and DK which is a sucrose fatty acid ester Ester F-50 (Daiichi Kogyo Seiyaku Co., Ltd., HLB value 6.0, monoester content 30%) 0.2 g, ethyl alcohol (Japan Alcohol Sales Co., Ltd., ethyl alcohol content 99% or more) 60 g And 10 g of glycerin (manufactured by NOF Corporation) as a polyhydric alcohol was added and dissolved by stirring. To this was added 10 g of thioctic acid (trade name: Lipoec, manufactured by Cognis Japan Co., Ltd., content of 99% or more) and solubilized by a stirring operation to obtain a thioctic acid-containing composition. 0.2 g of this thioctic acid-containing composition was taken, and 99.8 g of water was added to prepare a 0.2% aqueous dispersion.

Test example 1
The state of the 0.2% aqueous dispersion of the thioctic acid-containing composition obtained in Examples 1 to 4 and Comparative Examples 1 and 2 was visually confirmed. Moreover, after each composition was stored at 37 ° C. for 30 days, the state of the composition was compared with that before storage.
The results are shown in Table 1.

  From the above results, the thioctic acid-containing composition of the present invention was uniformly solubilized and dispersed when dispersed in water, and the storage stability of the composition was also excellent.

Test example 2
Dissolve 8% granulated sugar, 0.12% citric acid and 0.03% trisodium citrate in 91.65% water to obtain Bx. An acid sugar solution of 8.2, pH: 3.1 was prepared. 0.2% of each of the thioctic acid-containing compositions obtained in Example 1 and Comparative Example 1 was added to the acid sugar solution, and after heat sterilization at a temperature of 93 ° C., the plastic bottle was filled with a hot pack and then cooled. A thioctic acid-containing beverage was obtained. The sample containing the thioctic acid-containing composition of Example 1 was uniformly solubilized and dispersed, whereas the sample containing the thioctic acid-containing composition of Comparative Example 1 was clouded and precipitates were observed.

  From the above results, it has been clarified that the thioctic acid-containing composition of the present invention can be uniformly solubilized and dispersed in a beverage, and thus a highly stable beverage can be prepared.

Test example 3
A lotion was prepared by mixing 25% ethyl alcohol, 2% glycerin, 0.3% potassium hydroxide, an appropriate amount of fragrance, and 72.5% water. After 0.2% of the thioctic acid-containing composition obtained in Example 1 and Comparative Example 1 was added to and mixed with the lotion, the bottle was filled into a thioctic acid-containing lotion. The sample containing the thioctic acid-containing composition of Example 1 was uniformly solubilized and dispersed, whereas the sample containing the thioctic acid-containing composition of Comparative Example 1 was clouded and precipitates were observed.

  From the above results, it has been clarified that the thioctic acid-containing composition of the present invention can be solubilized and dispersed uniformly in the skin lotion, so that a highly stable skin lotion can be prepared.

  According to the present invention, it is possible to prepare a thioctic acid-containing composition that is excellent in storage stability and can be uniformly solubilized and dispersed in water.

Claims (7)

A thioctic acid-containing composition comprising an emulsifier having thioctic acid and HLB of 9 or more. The thioctic acid-containing composition according to claim 1, wherein the emulsifier having an HLB of 9 or more is a polyglycerin fatty acid ester. The polyglycerin fatty acid ester is a polyglycerin fatty acid ester in which the content of one kind of polyglycerin selected from tri, tetra, penta, hexa, hepta, octa, nona and decaglycerin is 35% or more in the polyglycerin composition. The thioctic acid containing composition of Claim 1 or Claim 2. The thioctic acid-containing composition according to any one of claims 1 to 3, comprising ethyl alcohol. The thioctic acid-containing composition according to any one of claims 1 to 4, comprising a polyhydric alcohol. Food-drinks containing the thioctic acid containing composition in any one of Claims 1-5. Cosmetics comprising the thioctic acid-containing composition according to any one of claims 1 to 5.