TW201626903A - Method for stabilization of 2-O-α-D-glycosyl-L-ascorbic acid in acidic aqueous media - Google Patents

Abstract

The present invention has been made in an effort to provide a simple and widely used stabilization method for 2-O-α-D-glycosyl-L-ascorbic acid in an acidic aqueous medium. The present invention solves the above problems by providing a method for stabilizing 2-O-α-D-glycosyl-L-ascorbic acid in an acidic aqueous medium, which is characterized in that 2-O-α-D-glycosyl- L-ascorbic acid and a sugar alcohol selected from a carbon number of 4 to 6, a glycosyl fructose or a sugar alcohol thereof, a sugar trisaccharide, a sugar-based trehalose, a cinnamic acid derivative, a catechin or a gallic acid derivative, and tartaric acid One or two or more stabilizers coexisting with a salt thereof or an amino acid or a peptide.

Description

Method for stabilization of 2-O-α-D-glycosyl-L-ascorbic acid in acidic aqueous media

The present invention relates to a method for the stabilization of 2-O-α-D-glycosyl-L-ascorbic acid, and in particular to a method for the stabilization of 2-O-α-D-glycosyl-L-ascorbic acid in an acidic aqueous medium. .

L-ascorbic acid (vitamin C) has excellent physiological activity or antioxidant activity and has been used in various applications such as foods and drinks and cosmetics. In particular, in order to utilize this antioxidant effect, other substances or compositions which are easily oxidized are protected by oxidation, and are widely used for the purpose of suppressing browning or decomposition. On the other hand, L-ascorbic acid is an unstable compound and is easily oxidatively decomposed, and has a large problem of easily losing physiological activity.

In order to solve the problem of the L-ascorbic acid, the applicant as a co-applicant in Patent Document 1 discloses that a 2-D-glucose 2-O-α-D is bonded to the hydroxyl group at the 2nd position of L-ascorbic acid. -glycosyl-L- ascorbic acid. The 2-O-α-D-glycosyl-L-ascorbic acid is non-reducing and stable, and in vivo, has the original L-ascorbic acid which decomposes into L-ascorbic acid and D-glucose by living enzymes. The epoch-making nature of physiological activity. The applicant has established an industrial production method of the 2-O-α-D-glycosyl-L-ascorbic acid, which is supplied to the market in the form of a powder containing 2-O-α-D-glycosyl-L-ascorbic acid anhydrous crystals. It is sold as the product name "Asko fresh" (a product of the company, which is a product of the food and beverage products), and is sold as the product name "AA2G" (a product of the company). .

However, as described in Patent Document 2, 2-O-α-D-glycosyl-L-ascorbic acid is a compound having significant stability when compared with L-ascorbic acid, but is long in an aqueous solution in an acidic region. When stored, it is slowly decomposed, especially in acidic conditions below pH 5.0, which is particularly pronounced.

As a method for the stabilization of 2-O-α-D-glycosyl-L-ascorbic acid in the past, for cosmetic use, it is known to add a strong base substance to 2-O-α-D-glycosyl-L-ascorbic acid. A cosmetic (refer to Patent Document 3) or a cosmetic containing a basic amino acid (see Patent Document 4), a cosmetic containing a basic peptide (see Patent Document 5), and the like. However, the alkaline substance is an essential component, and it is based on the idea that the neutralization of 2-O-α-D-glycosyl-L-ascorbic acid itself is acidic, and the stability over time can be improved. Specifically, Patent Document 3 discloses a technique in which sodium hydroxide, calcium hydroxide, or the like, which is an inorganic strong alkali substance, is added so as not to become an acidic region. For Patent Documents 4 and 5, only the use of a basic substance is disclosed. Oil, B Alcohols, by the combined action of these multiple components, can improve specific examples of stability. These conventional stabilization methods use an alkaline substance as an essential component, and are sometimes limited by other components that must be further stabilized, and even if 2-O-α-D-glycosyl-L-ascorbic acid can be stabilized, The scope of use is also limited.

For example, a carbonated beverage, a citrus-containing seasoning, a convergent cosmetic, a hydrochloric acid-based detergent, an acidic preservative (benzoic acid-based, sorbic acid-based, etc.) is required to be an acidic component, and an alkaline substance cannot be used. A convenient method for the stabilization of 2-O-α-D-glycosyl-L-ascorbic acid, which must be an acidic acidic aqueous medium, is not disclosed at all.

Under such circumstances, if a means for stabilizing 2-O-α-D-glycosyl-L-ascorbic acid in an acidic aqueous medium can be established, 2-O- in various fields mainly including foods and drinks or cosmetics can be expected. The usefulness of α-D-glycosyl-L-ascorbic acid can be further widely used.

[Previous Technical Literature] [Patent Literature]

[Patent Document 1] JP-A-3-139288

[Patent Document 2] International Publication No. WO06022174

[Patent Document 3] JP-A-2001-199863

[Patent Document 4] JP-A-2006-188461

[Patent Document 5] JP-A-2008-088088

The present invention provides an acidification system for 2-O-α-D-glycosyl-L-ascorbic acid in an acidic aqueous medium, and an acidic water system containing 2-O-α-D-glycosyl-L-ascorbic acid. The method for producing a media composition, the acidic aqueous medium composition obtained by the production method, and the stabilizer for 2-O-α-D-glycosyl-L-ascorbic acid are problems.

In order to solve the above problems, the present inventors have repeated detailed studies on compounds for improving the stability of 2-O-α-D-glycosyl-L-ascorbic acid in an acidic aqueous medium, and found that 2-O-α- D-glycosyl-L-ascorbic acid and a sugar alcohol selected from (1) a sugar alcohol having 4 to 6 carbon atoms, (2) glycosyl fructose or a sugar alcohol thereof, (3) glucose trisaccharide, and (4) a glycosyl group One or more of trehalose, (5) cinnamic acid derivative, (6) catechin or gallic acid derivative, (7) tartaric acid or a salt thereof, and (8) amino acid or peptide When the stabilizer (hereinafter sometimes referred to as the "1) to (8) compound group is "the present stabilizer"), the 2-O-α-D-glycosyl-L-ascorbic acid may be unstable in the original place. The present invention was completed by stabilizing in an acidic aqueous medium.

That is, the present invention provides a method for the stabilization of 2-O-α-D-glycosyl-L-ascorbic acid in an acidic aqueous medium, characterized in that 2-O-α-D-glycosyl-L-ascorbic acid is used. And a sugar alcohol selected from the group consisting of a sugar alcohol having 4 to 6 carbon atoms, a glycosyl fructose or a sugar alcohol thereof, a glucose trisaccharide, a sugar-based trehalose, a cinnamic acid derivative, a catechin or a gallic acid derivative, tartaric acid or a salt thereof ,and One or two or more kinds of stabilizers of amino acids or peptides coexist, and the above problems are solved.

Further, in another aspect, the present invention provides a method for producing an acidic composition comprising stabilized 2-O-α-D-glycosyl-L-ascorbic acid, which comprises 2-for acidic aqueous media O-α-D-glycosyl-L-ascorbic acid and a sugar alcohol selected from the group consisting of a sugar alcohol having 4 to 6 carbon atoms, a glycosyl fructose or a sugar alcohol thereof, a glucose trisaccharide, a sugar-based trehalose, a cinnamic acid derivative, and a child The above-mentioned problem is further solved by a step in which a tea or a gallic acid derivative, tartaric acid or a salt thereof, and one or two or more kinds of stabilizers of an amino acid or a peptide coexist.

Further, the present invention further solves the above problems by providing an acidic composition containing 2-O-α-D-glycosyl-L-ascorbic acid obtained by the above production method.

Further, the present invention provides a stabilizer for improving the stability of 2-O-α-D-glycosyl-L-ascorbic acid in an acidic aqueous medium, which contains, as an active ingredient, a material selected from carbon numbers 4 to 6. Sugar alcohol, glycosyl fructose or its sugar alcohol, sugar trisaccharide sugar alcohol, sugar-based trehalose, cinnamic acid derivative, catechin or gallic acid derivative, tartaric acid or a salt thereof, and amino acid or peptide 1 The above problem can be solved by two or more types.

According to the present invention, by coexistence with a stabilizer, the 2-O-α-D-glycosyl group can be significantly improved in an acidic aqueous medium in which 2-O-α-D-glycosyl-L-ascorbic acid is initially unstable. -L-ascorbic acid stability, so far The usefulness of 2-O-α-D-glycosyl-L-ascorbic acid in an acidic aqueous medium which is not utilized can be widely used.

[Formation of the Invention]

The present invention relates to 2-O-α-D-glycosyl-L-ascorbic acid (hereinafter, simply referred to as "ascorbic acid 2-glucoside" in the present specification) and sugar alcohol, glycosyl fructose selected from carbon number 4 to 6. Or one or more of a sugar alcohol, a sugar trisaccharide sugar alcohol, a sugar-based trehalose, a cinnamic acid derivative, a catechin or a gallic acid derivative, a tartaric acid or a salt thereof, and an amino acid or a peptide A method for the stabilization of ascorbic acid 2-glucoside in acidic water-based media characterized by coexistence of Cheng An Dinghua.

The term "aqueous medium" as used in the present specification means a water which is soluble and can contain ascorbic acid 2-glucoside and a stabilizer, or a physiologically acceptable mixture of a water-soluble organic solvent and water. Examples of the organic solvent soluble in water include ethyl alcohol, isopropanol, propanol, behenyl alcohol, stearyl alcohol, isostearyl alcohol, cetyl alcohol, and lanolin alcohol. Alcohols such as fatty acid monohydric alcohols, sterols, polyhydric alcohols, and sugar alcohols. More specifically, for example, "Food Additive List 2010" (2010, published by Food Chemical News Co., Ltd.) or "Comparative Component Guide for Cosmetic Ingredients 2nd Edition" (2000, published by Fragrance Journal, Inc.) Classified as an alcohol.

Further, in the present specification, an acidic aqueous medium means an aqueous medium which does not reach pH 7.0. The stabilization method of the present invention is resistant to blood stasis When the acid 2-glucoside is present in an acidic aqueous medium, the effect is exhibited. However, when the pH is 6.0 or less, the effect is remarkably remarkable, and when it is in the range of pH 2.0 to 5.0, the effect is particularly exhibited. The stabilization method of the present invention can exert its effects well in any kind of material which makes the aqueous medium acidic, for example, citric acid, phosphoric acid, malic acid, gluconic acid, and Malay which are widely used in foods and drinks, cosmetics, and the like. Acids, aspartic acid, succinic acid, glucuronic acid, fumaric acid, glutamic acid, adipic acid, and these salts are widely practiced in acidic aqueous media containing sodium bicarbonate, hydrochloric acid, and the like.

In the present specification, the stabilization of ascorbic acid 2-glucoside refers to the condition that the stabilizer is kept at 100 ° C for 5 hours in an acidic aqueous medium, or in the coexistence of fructose glucose liquid sugar, and at the same time with the stabilizer. The residual ratio of ascorbic acid 2-glucoside after storage at 40 ° C for 4 weeks in the aqueous medium was higher than 5% when compared with the control group not containing the stabilizer. The concentration of the ascorbic acid 2-glucoside in the composition containing the acidic aqueous medium set in the present invention is not particularly limited to a sufficient amount for the purpose of addition, and is usually 0.0001 to 10% by mass, preferably 0.001 to 1 The range of mass %.

In the present specification, a sugar alcohol having 4 to 6 carbon atoms, which represents a sugar alcohol formed by reduction of a carbonyl group of a sugar having 4 to 6 carbon atoms constituting a sugar. Preferred examples of this include erythritol, threitol, arabitol, litprozil, iditol, galactitol, sorbitol, especially selected from erythritol and Lipitor. One or two of sorbitol and galactitol The above is particularly useful in the aspect of stabilizing ascorbic acid 2-glucoside in an acidic aqueous medium.

The glycosyl fructose or the sugar alcohol thereof referred to in the present specification means a sugar which is glucose-glycodated by glucose and a sugar alcohol which is reduced by sugar on fructose. Preferred examples of the sugar include sucrose, sucrose, lactulose, and sugar alcohols (for example, palatin which reduces palatinose), and particularly one or more selected from the group consisting of sucrose and palatin. It is useful to stabilize the ascorbic acid 2-glucoside in an acidic aqueous medium. Therefore, parakin is particularly useful for the stability of heat or acid as compared with sucrose.

The sugar alcohol of the glucose trisaccharide in the present specification means a sugar alcohol in which glucose is reduced as a trisaccharide constituting a sugar. Preferred examples of this include maltose sorbitol which has been reduced by pan sugar, maltosorbitol which has been reduced by isopanose, and maltotriitol which has been reduced by maltotriose. In particular, maltotriitol is particularly useful in the aspect of stabilizing ascorbic acid 2-glucoside in an acidic aqueous medium.

The glycosyl trehalose in the present specification means a sugar derivative having trehalose having a trehalose structure at the end. Preferred examples of this include sugar-based trehalose, maltose-based trehalose, and maltotriose-based trehalose, and in particular, maltose-based trehalose is determined by stabilizing ascorbic acid 2-glucoside in an acidic aqueous medium. Particularly useful. The sugar-based trehalose containing a relatively large amount of maltose-based trehalose can be prepared, for example, by the method described in the abstract of WO 040007472, and as a commercial product of the sugar-based trehalose, a "Hello index" (made by Hayashibara) Co., Ltd.), "Tornare" (Linyuan Manufacturing Co., Ltd.) Wait.

The cinnamic acid derivative in the present specification means an ester derivative having a cinnamic acid structure, a derivative having a phenolic hydroxyl group, or a dehydration condensation of a carboxyl group and a linear alcohol. Examples of the preferred examples include methyl cinnamate, ethyl cinnamate, butyl cinnamate, caffeic acid, and ferulic acid. In particular, one or more selected from the group consisting of caffeic acid and ferulic acid are used in an acidic aqueous medium. It is particularly useful to stabilize the ascorbate 2-glucoside.

The catechin or gallic acid derivative referred to in the present specification means an epimer or a hydroxy group of catechin having a catechin structure, and these gallic acid esters or those having a gallic acid structure. Examples of the preferred examples include epicatechin, gallocatechin, epicatechin gallate, gallic catechin gallate, and gallic acid, especially selected from One or more of gallocatechin and gallocatechin gallate are particularly useful in the case of stabilizing ascorbic acid 2-glucoside in an acidic aqueous medium.

The tartaric acid or a salt thereof in the present specification means tartaric acid containing a L form, a D form, and a mesogenic form, and a salt thereof. Preferred examples of this include tartaric acid, sodium tartrate, potassium tartrate, calcium tartrate, and magnesium tartrate. Particularly, tartaric acid is particularly useful in the case of stabilizing ascorbic acid 2-glucoside in an acidic aqueous medium.

In the present specification, the amino acid or peptide is one or more selected from the group consisting of a peptide linked to an α-amino acid and an α-amino acid thereof by peptide bonding. Preferred examples of the amino acid include cysteine, methionine, tryptophan, and lysine, each of which is a preferred example of the peptide. In particular, it is particularly useful from the viewpoint that one or more selected from the group consisting of cysteine and methionine can stabilize the ascorbic acid 2-glucoside in an acidic aqueous medium.

In the stabilization method of the present invention, it is preferable to mix ascorbic acid 2-glucoside which stabilizes ascorbic acid 2-glucoside in an acidic aqueous medium with the present stabilizer (the total amount when using a plurality of kinds), although Depending on the compound to be combined, it is usually in the range of 1:0.01 to 1:500 at a molar ratio, preferably a ratio of 1:0.05 to 1:20. When the molar ratio of the present stabilizer of ascorbic acid 2-glucoside is less than 0.01 times, a sufficient effect may not be obtained, and if it exceeds 500 times, the corresponding effect of the amount of use cannot be obtained, which is not preferable.

According to the stabilization method of the present invention, it has the advantage that since ascorbic acid 2-glucoside is stabilized in an acidic aqueous medium, ascorbic acid 2-glucoside or ascorbic acid 2-glucoside is decomposed by living enzymes. The ascorbic acid produced has functions such as vitamin C strengthening, anti-oxidation, freshness retention, color development, browning prevention, odor inhibition, anti-inflammatory, acne improvement, whitening effect, The aging prevention action, the biosynthesis promoting action such as collagen, the cell disorder suppressing action by ultraviolet rays, and the like can be sufficiently exhibited after the ascorbic acid 2-glucoside is stored in an acidic aqueous medium.

The present invention also provides a method for producing an acidic aqueous medium composition containing ascorbic acid 2-glucoside which is stabilized with ascorbic acid 2-glucoside. In order to cooperate with the purpose of using ascorbic acid 2-glucoside In the suitable acidic water medium selected, the ascorbic acid 2-glucoside and the present stabilizer can be used to achieve the stabilization effect, usually at a pH of less than 7.0 and preferably 6.0 or less, preferably 2.0 to 5.0. An acidic aqueous medium composition containing ascorbic acid 2-glucoside as a target can be produced at a molar ratio of from 1:0.01 to 1:500, preferably from 1:0.05 to 1:20. It is better.

The acidic aqueous medium composition containing ascorbic acid 2-glucoside obtained by the above production method is in a state in which part or all of ascorbic acid 2-glucoside contained in the composition is dissolved in an aqueous medium, and in the aqueous medium, only The amount of the stabilizer which can stabilize the ascorbic acid 2-glucoside is not particularly limited, and examples thereof include a liquid, a cream, a jelly, a paste, a gel, an emulsion, and a sheet. Shape, aerosol, spray, etc. Specific examples of the composition include a beverage having a water content of 80% by mass or more, a food or drink such as various foods, a cosmetic composition such as a lotion or a cosmetic liquid, a mouthwash, a mouth spray, and the like. An oral composition such as an oral dry prevention agent, a pharmaceutical composition such as a liquid preparation, or the like. Among them, a cosmetic composition such as a drink or the like, a lotion, a cosmetic liquid or the like is preferable, and a beverage is preferred. In the acidic aqueous medium composition containing ascorbic acid 2-glucoside of the present invention, in addition to ascorbic acid 2-glucoside and the present stabilizer, a component for use in foods, drinks, cosmetics, and pharmaceuticals may be further added. Further, in the acidic aqueous medium composition of the present invention, it may be dried by freeze drying, spray drying, or other conventional methods, and further formed into a desired shape such as a block, a flat surface, or a sheet, as necessary. Can also be used as a time of use The composition of the solution is utilized.

A preferred specific example of the acidic aqueous medium composition containing ascorbic acid 2-glucoside of the present invention is an acidic beverage. The acidic beverage in the present specification generally has a pH of less than 7.0, preferably 6.0 or less, preferably 2.0 to 5.0, and examples thereof include a carbonated nutritional drink, a guarana drink, and a milk. Frost soda, cola, soda, champagne carbonated drink, ginger soda, flash. Coffee (with carbonated coffee), soda (carbonated water), tea. Soda (with black carbonated tea), quinine water, beer-flavored beverage, cantaloupe soda, lemonade, root beer, carbonated beverages with juice, etc.; orange juice, apple juice, grape juice, grapefruit juice, pineapple juice Such as juice drinks; vegetable juice; lactic acid bacteria beverage; acetic acid beverage; citric acid beverage; fermented milk; sports drinks.

Further, for example, various seasonings such as salad dressing, edible vinegar, three cups of vinegar, powdered sushi vinegar, fruit vinegar, dip sauce, tomato sauce, kebab sauce, curry paste, compound seasoning, rice lin, and new rice lin; Ice cream, fruit smoothies and other freezing points; fruit syrup stains, ice honey and other syrups; jam, fruit sauce, syrup stains, brewed wine, distilled wine, blended wine, synthetic wine, wine, fruit wine, wine and other alcohol.

The food or drink as exemplified above can stabilize the ascorbic acid 2-glucoside by the present stabilizer even under acidic conditions, so that it can be enhanced with vitamin C, antioxidant, taste quality, freshness retention, and color development. It is advantageously used as a food or drink that promotes, prevents browning, and inhibits odor.

Another preferable specific example of the acidic aqueous medium composition containing ascorbic acid 2-glucoside as the present invention is a preservative which can be added to foods and drinks or cosmetics to prevent deterioration of these qualities. The storage material usually has a pH of less than 7.0, preferably 6.0 or less, preferably 2.0 to 5.0, and the ascorbic acid 2-glucoside is contained in an amount of 0.0001 to 10% by mass, preferably 0.001 to 1% by mass. This contains a present stabilizer in a ratio of from 1:0.01 to 1:500, preferably from 1:0.05 to 1:20. The preservation material can maintain long-term preservation by increasing the stability of ascorbic acid 2-glucoside. Moreover, since the stability of ascorbic acid 2-glucoside is improved, the anti-oxidation effect and the fading prevention effect of the ascorbic acid originally produced by the decomposition of ascorbic acid 2-glucoside or ascorbic acid 2-glucoside , can be played more stably. In addition, when the preservative is added, the final concentration of ascorbic acid 2-glucoside as the target food or drink or cosmetic is 0.0001 to 10% by mass, preferably 0.001 to 1% by mass.

When the anti-oxidation action of the free radical trapping energy of ascorbic acid produced by the decomposition of ascorbic acid 2-glucoside or ascorbic acid 2-glucoside is utilized, the object of receiving the antioxidant is only the substance which can avoid oxidation, Materials, products, and the like have effects, and examples thereof include cosmetics containing fruits, vegetables, foods, fats or waxes and derivatives thereof, surfactants, perfumes, and vitamins. Further, the unsaturated fatty acid contained in these may be discolored by oxidation, or may be odorized by release of metal odor or sulfur odor, and the preservation material of the present invention can be applied particularly to a composition containing an unsaturated fatty acid.

When the anti-ascorbic acid which is produced by the decomposition of ascorbic acid 2-glucoside or ascorbic acid 2-glucoside is used as a target, a tar type pigment (food red No. 2) which is a synthetic coloring material added to foods and drinks is usually used as a target. , edible yellow No. 4, edible cyan No. 1, etc.), inorganic pigments (titanium dioxide, ferric oxide), natural synthetic pigments (sodium iron chlorophyllin, β-carotene, copper chlorophyll, etc.) Beverage or other food or drink, or carminic acid, laconic acid, sunflower yellow, annatto, beetin, melanin, crocin, glucoside, anthocyanin, capsanthin, carotene, tomato Natural ingredients such as erythromycin, chlorophyll, delphinidin, cyanidin, mallow pigment, petunia, paeoniflorin, astaxanthin, myoglobin, lutein and the like. In addition, in addition to synthetic pigments (tar dyes) for cosmetics, leeks, red peony, carmine, peach red B, bengal rose red, acid red, lemon yellow, sunset yellow FCF, fast green FCF, bright blue FCF, indigo resin In addition to cosmetics such as red, cosmetics such as canthaxanthin, gardenia blue, gardenia yellow, comfrey, safflower, safflower yellow, rutin, quercetin, and curcumin, which contain natural pigments for cosmetics, may also be mentioned. For example, an exit red, an eye line, or the like can be used as an object of utilizing the function of preventing fading.

Another preferred specific example of the acidic aqueous medium composition containing ascorbic acid 2-glucoside of the present invention is a lotion. The lotion is basically such that the pH is less than 7.0, preferably in the range of pH 4.0 to 6.0, and it is particularly preferable to show a relatively strong acidic pH-promoting lotion in the range of pH 4.0 to 5.0 in the lotion. Further, basic cosmetic materials such as a cosmetic liquid, an emulsion, a cream, an emulsifier, a cosmetic oil, and a mask can be mentioned; Makeup, bathing lotion, etc.; aerosol, such as foundation, lipstick, mascara, eye shadow, eyeliner, eyebrow pencil and nail polish; sunscreen, odor prevention agent, water worm therapeutic agent, antipruritic, Wound healing agent, cleaning agent, detergent, anti-inflammatory analgesic, acne treatment agent, dysentery agent, bactericidal disinfectant, whitening agent, ultraviolet ray preventive agent, etc. The acidic water-based media composition containing ascorbic acid 2-glucoside of the present invention A cosmetic composition of a preferred specific example. The acidic aqueous medium composition containing ascorbic acid 2-glucoside of the present invention or these cosmetic, external pharmaceutical, and external quasi-drugs mixed together can be stabilized by ascorbic acid 2-glucoside by the present stabilizer under acidic conditions. Therefore, even in the long-term preservation, it is also advantageous to use ascorbic acid 2-glucoside or ascorbic acid 2-glucoside to inhibit the inflammation, acne, whitening, aging prevention of ascorbic acid originally produced by decomposition of enzymes in vivo. It promotes the synthesis of living components such as collagen, and inhibits cell damage by ultraviolet rays.

Still another preferable specific example of the acidic aqueous medium composition containing ascorbic acid 2-glucoside of the present invention is an oral composition. The oral composition basically has a pH of less than 7.0, but is particularly excellent in the form of a liquid toothpaste provided by a relatively strong acidic solution, and also for an oral composition provided in a relatively weakly acidic solution. The stabilization effect of the present invention can be exerted, for example, it is also a liquid or pasty toothpaste in the range of pH 4.0 to 6.0 which is widely used in the field. Further, a toothpaste, a paste, a cream, a mouthwash, an oral moisturizer, a liquid, a gel, a paste, an ointment, a spray, or the like can be used as the acidic water system containing ascorbic acid 2-glucoside of the present invention. Better specifics of media composition The oral composition of the example is exemplified. The acidic aqueous medium composition containing ascorbic acid 2-glucoside of the present invention or the oral composition containing the same can also stabilize the ascorbic acid 2-glucoside by the present stabilizer under acidic conditions, so even after long-term storage, It is also advantageous to use the action of ascorbic acid originally produced by the decomposition of ascorbic acid 2-glucoside or ascorbic acid 2-glucoside, which is inhibited by ascorbic acid.

The stabilizer of the present specification is an active ingredient for improving the stability of ascorbic acid 2-glucoside in an acidic aqueous medium, and is represented by a sugar alcohol having a carbon number of 4 to 6, a glycosyl fructose or a sugar alcohol thereof, and a glucose three. a sugar alcohol, a sugar-based trehalose, a cinnamic acid derivative, a catechin or a gallic acid derivative, a tartaric acid or a salt thereof, and one or more compounds of an amino acid or a peptide, or the like, wherein As an active ingredient, it contains erythritol, Lipitor, sorbitol, galactitol, sucrose, palatin, maltotriose, maltosyl trehalose, caffeic acid, ferulic acid, gallic catechin It is better to have gallocatechin gallate, cysteine, methionine, tryptophan, lysine or collagen peptide.

Hereinafter, the present invention will be more specifically illustrated by the examples, but the present invention is not limited to the following examples.

[Example 1] <Method for stabilization of ascorbic acid 2-glucoside by saccharide in acidic water medium>

According to the prescription shown in Table 1, citric acid-citric acid at a concentration of 100 mM In the sodium buffer (pH 3.5), 3.0 mM (about 0.1% by mass) of ascorbic acid 2-glucoside (Linyuan Manufacturing Co., Ltd., reagent grade, purity: 99.9% by mass or more) and the present stabilizer ( 1) Sugar alcohols having a carbon number of 4 to 6 (erythritol, Lipitor, sorbitol, galactitol), (2) glycosyl fructose or its sugar alcohol (sucrose, palatin), (3) glucose Any one of trisaccharide sugar alcohol (maltotriose) (corresponding to test sample 1 to 7 in Table 1), an aqueous solution containing 30 mM, and the above buffer at the above concentration and the above-mentioned concentration of the above-mentioned ascorbic acid 2-glucose The glycoside trehalose prepared by the method described in Example 1 of the International Publication No. WO04071472, which is an intrinsic stabilizer, is an aqueous solution containing a solid concentration of 0.1% by mass (corresponding to the test of Table 1). Sample 8) After measuring the pH, each aqueous solution was filled in 3 ml of a screw cap test tube having a capacity of 3 ml, and heat-treated at 100 ° C for 5 hours. After the heat treatment, it was rapidly cooled in ice water, and the obtained sample was analyzed by high-speed liquid chromatography (HPLC), and the effect of the stabilization method of the present invention was examined by the residual ratio of ascorbic acid 2-glucoside described later. Further, as a comparative example, in place of the present stabilizer, α-cyclodextrin which is a monosaccharide glucose, a disaccharide maltose, a trivalent alcohol glycerin, or a cyclic oligosaccharide (corresponding to the comparative sample of Table 1) was prepared. 1 to 4) An aqueous solution containing a concentration of 30 mM was further used as a control group, and an aqueous solution containing only ascorbic acid 2-glucoside and citric acid-sodium citrate buffer was prepared in the same manner as described above, and the test sample 1 described above was prepared. In the same manner, pH measurement, heat treatment, and pH measurement and HPLC analysis after heat treatment were carried out in the same manner, and the residual ratio of ascorbic acid 2-glucoside was investigated. By the way, although detailed data is omitted, ascorbic acid 2-glucoside is in acid When stored in a water-based medium (near pH 3.5) at 25 ° C, the residual rate of about 8 weeks is about 80%, which can be confirmed by a preliminary investigation result. The heat treatment in the present example was carried out under the conditions of an accelerated test in which the ascorbic acid 2-glucoside was stored in an acidic aqueous medium (near pH 3.5) at 25 ° C for about 8 weeks. Further, the glycose-based trehalose sugar composition used in the present Example was 4.1% by mass of glycosyl trehalose, 52.5% by mass of maltose-based trehalose, 1.1% by mass of maltotriose-based trehalose, and 42.3% by mass of other sugars. .

The stabilization effect of ascorbic acid 2-glucoside of various sugars and sugar alcohols was quantified and evaluated by comparison of absorption peak areas detected by HPLC under the conditions shown below. That is, the absorption peak area (X) of ascorbic acid 2-glucoside detected in the aqueous solution before the heat treatment was determined, and the absorption of ascorbic acid 2-glucoside detected in the aqueous solution after heating at 100 ° C for 5 hours was obtained. The percentage of the peak area (Y) is {(Y/X) × 100} (%) as the residual ratio of ascorbic acid 2-glucoside. The results of these assessments are shown in Table 1.

<HPLC conditions>

Pipe column: CAPCELL PAK NH2 SG80 (4.6mm × 250mm, manufactured by Shiseido Co., Ltd.)

Dissolved solution: 20 mM potassium dihydrogen phosphate / acetonitrile (40/60), pH 2.0

Flow rate: 0.5ml/min

Column temperature: 35 ° C

Detection: UV245nm

Sample amount: 10μl

As shown in Table 1, it was found that for the heat treatment at 100 ° C for 5 hours, the residual rate of ascorbic acid 2-glucoside in the control without adding any sugar and sugar alcohol was 81%, and erythritol, Lipitor, sorbitol, galactose, sucrose, palatin, and maltotriose, each of which is added to the ascorbic acid 2-ascorbate glucoside at a molar ratio of 10 times in the molar ratio of 1 to 7, and in the glycosyl group Trehalose For the test sample 8 in which the ascorbic acid 2-ascorbate glucoside was added in the same amount by mass ratio, the residual rate of ascorbic acid 2-ascorbyl glucoside was 95 to 100% higher, which means erythritol, Lipu Toluene, sorbitol, galactose, sucrose, palatin, maltotriose and glycosyl trehalose can achieve a significant effect of stabilizing ascorbic acid 2-glucoside in an acidic aqueous solution. The results indicate glycosylglycans such as erythritol, Lipitor, sorbitol, and galactitol having a carbon number of 4 to 6, sugar glycosides such as sucrose or palatin, or sugar trisaccharides such as sugar alcohol and maltotriose. The sugar alcohol and sugar-based trehalose are useful as stabilizers for ascorbic acid 2-glucoside in an acidic aqueous medium.

On the other hand, in the case of comparing samples 1 to 4 in which glucose, maltose, glycerin, and α-cyclodextrin were mixed at 30 mM of the same concentration as the test sample, the residual ratio of ascorbic acid 2-glucoside was 80 to 84%. This is the same level as the control group, which means that these glucose, maltose, glycerol, and α-cyclodextrin cannot achieve the effect of stabilizing ascorbic acid 2-glucoside in an acidic aqueous medium.

[Embodiment 2] <Method for the stabilization of ascorbic acid 2-glucoside in an acidic water medium other than sugars>

According to the prescription shown in Table 2, a concentration of 3.0 mM (about 0.1% by mass) of ascorbic acid 2-glucoside was prepared in a citric acid-sodium citrate buffer (pH 3.5) having a concentration of 100 mM (Linyuan Manufacturing Co., Ltd., test Pharmacological grade, purity 99.9% by mass or more) and (5) cinnamic acid derivative (caffeic acid, ferulic acid), (6) catechin or gallic acid derivative (gallocatechin) And (7) any of tartaric acid or a salt thereof (tartaric acid) (corresponding to the test sample 9 to 12 in Table 2), an aqueous solution containing 0.3 mM, and a salt of a hydroxy acid as a comparative example. An aqueous solution containing sodium lactate, sodium gluconate, sodium benzoate (corresponding to Comparative Samples 5 to 7 of Table 2) at a concentration of 0.3 mM, under the same conditions as in Example 1 The heat treatment was carried out, and pH measurement and HPLC analysis were carried out in the same manner before and after the heat treatment, and the residual ratio of ascorbic acid 2-glucoside was examined. The results are shown in Table 2. Show.

As shown in Table 2, for the heat treatment maintained at 100 ° C for 5 hours, the residual rate of ascorbic acid 2-glucoside in the control (no addition) was 81%, and tartaric acid, caffeic acid, ferulic acid, and no In the test samples 9 to 12 in which the ascorbic acid 2-glucoside was combined with the molar ratio of the ascorbic acid 2-glucoside, the residual rate of the ascorbic acid 2-glucoside was 93 to 100%, which was confirmed to be remarkable. The effect of ascorbic acid 2-glucoside in tartaric acid, caffeic acid, ferulic acid and gallic catechin in acidic aqueous media. This result indicates that cinnamic acid derivatives such as caffeic acid, ferulic acid, catechin derivatives such as gallic catechin, and tartaric acid such as tartaric acid or a salt thereof can be used as the stability of ascorbic acid 2-glucoside in an acidic aqueous medium. The agent is useful.

On the other hand, in the comparative sample 5 to 7 in which calcium ascorbate 2-glucoside was mixed with calcium lactate or sodium gluconate or sodium benzoate, the residual ratio of ascorbic acid 2-glucoside was 80 to 81%, which was the same as the control group. This means that these calcium lactate, sodium gluconate, sodium benzoate and The stabilization effect of ascorbic acid 2-glucoside in an acidic aqueous medium is shown.

<Reference example: Effect on the stability of sucrose in acidic water-based media, erythritol, sorbitol and tartaric acid>

It is known that sucrose is a saccharide which binds glucose and fructose, and in the same manner as ascorbic acid 2-glucoside in which glucose and ascorbic acid are combined, under acidic conditions, glucoside linkage between dissimilar molecules becomes unstable and is easily decomposed. In Tables 1 and 2, it was determined whether the compound exhibiting a stabilization effect on ascorbic acid 2-glucoside showed a stabilization effect on sucrose. According to the formulation shown in Table 3, for the concentration of 3.0 mM sucrose, each red was prepared. An acidic aqueous solution containing sugar alcohol, sorbitol, and tartaric acid at a concentration of 30 mM and a concentration of 0.3 mM. Thereafter, the same heat treatment as in Examples 1 and 2 was carried out, and the solution after the heat treatment was also subjected to pH measurement and HPLC analysis to investigate the residual ratio of sucrose.

The sucrose stabilization effect of the three compounds was quantified and evaluated by comparison of the absorption peak areas detected by HPLC under the conditions shown below. That is, for the absorption peak area (X) of sucrose detected in the aqueous solution before the heat treatment, the percentage of the absorption peak area (Y) of the sucrose detected in the aqueous solution after heating at 100 ° C for 5 hours was determined {( Y/X) × 100} (%) as the residual ratio of sucrose. The results of these assessments are shown in Table 3.

<HPLC conditions>

Pipe column: Asahipak NH2P-50 4E, NH2P-50G 4A (4.6mm × 250mm, manufactured by Showa Denko Co., Ltd.)

Dissolved solution: acetonitrile / water (65/35)

Flow rate: 0.8ml/min

Column temperature: 40 ° C

Check out: RI

Sample amount: 10μl

It is known from Table 3 that in the case of sucrose, for the heat treatment at 100 ° C for 5 hours, the residual rate is 0% for the acidic solution in the control (no addition), and for the addition of erythritol, sorbitol or tartaric acid. The residual rate of sucrose in Reference Samples 1 to 3 was also lower at 0%, so it was not confirmed that erythritol, sorbitol, and tartaric acid could stabilize sucrose.

As described above, erythritol, sorbitol, and tartaric acid having an effect of stabilizing ascorbic acid 2-glucoside in an acidic aqueous medium have no stability effect on sucrose. It is known from erythritol, The stabilization of sorbitol and tartaric acid is not a general effect on all glucosidic linkages between dissimilar molecules, but a specific effect on ascorbic acid 2-glucoside.

[Example 3] <A method for the stabilization of ascorbic acid 2-glucoside by an amino acid in an acidic aqueous medium>

In the above-described Examples 1 and 2, a general liquid composition product can be produced under heating conditions maintained at 100 ° C for 5 hours, which is set as extremely harsh conditions as compared with the conditions exposed during circulation. In fact, the conditions which are produced are compared with the fructose glucose liquid sugar which is used in many cases, such as a refreshing drink, and the amino acid is used to detect the ascorbic acid 2-glucose in the acidic aqueous medium under mild conditions of 40 ° C for 4 weeks. The effect of the stability of glycosides. Ascorbic acid 2-glucoside (Linyuan Manufacturing Co., Ltd., trade name "Asko fresh") was prepared at a concentration of 3.0 mM (about 0.1% by mass) in a citric acid-sodium citrate buffer (pH 3.0) having a concentration of 100 mM. An aqueous solution of 15% by mass of fructose glucose liquid sugar (manufactured by Japan Corn Starch Co., Ltd., trade name "Haifurakuto M75C") was heated to 95 ° C, and then cooled to a liquid temperature of 85 ° C. (8) Amino acid (cysteine, methionine, tryptophan, lysine) and peptide (collagen peptide, manufactured by Nitta Gelatin Co., Ltd., as a local stabilizer) Any one of the names "Ikuosu HDR-50DR" (equivalent to the test sample of Table 4) 13 to 17) were contained in a concentration of 3.0 mM, and 150 g of each of the aqueous solutions was filled in a 350 mL-capacity polyester bottle. Thereafter, it was quenched in a water bath and stored at 40 ° C for 4 weeks, and the obtained sample was analyzed by HPLC, and the effect of the stabilization method of the present invention was examined from the residual ratio of ascorbic acid 2-glucoside. Further, as a comparative example, an aqueous solution containing an amino acid derivative of L-carnitine in an aqueous solution containing 3.0 mM as a control contains only an aqueous solution of ascorbic acid 2-glucoside, fructose glucose liquid sugar, and citric acid-sodium citrate buffer. The preparation was carried out in the same manner as described above, and then heating and storage treatment were carried out in the same manner, and pH measurement and HPLC analysis were carried out to investigate the residual ratio of ascorbic acid 2-glucoside.

The stabilization effect of ascorbic acid 2-glucoside of various amino acids was quantified and evaluated by comparison of the absorption peak areas detected by HPLC under the conditions shown below. That is, the area (X) of the absorption peak of ascorbic acid 2-glucoside detected in the aqueous solution before the start of storage in 40 ° C for 4 weeks after quenching in a water bath was determined in the aqueous solution after storage at 40 ° C for 4 weeks. Percentage of absorption peak area (Y) of ascorbic acid 2-glucoside {(Y/X) × 100} (%), as a residual rate of ascorbic acid 2-glucoside. The results of these assessments are shown in Table 4.

<HPLC conditions>

Pipe column: CAPCELL PAK NH ₂ SG80 (4.6mm × 250mm, manufactured by Shiseido Co., Ltd.)

Dissolution: 20 mM potassium dihydrogen phosphate / acetonitrile (50 / 50), pH 2.0

Flow rate: 0.5ml/min

Column temperature: 35 ° C

Detection: UV245nm

Sample amount: 10μl

As is clear from Table 4, for the preservation treatment at 40 ° C for 4 weeks, the residual rate of the ascorbic acid 2-glucoside of the control was 66%, and each of the cysteine, methionine, tryptophan, and lysine was used. Amine hydrochloride and collagen peptide The residual rate of ascorbic acid 2-glucoside in the test samples 13 to 17 prepared by the prescription of Table 4 for ascorbic acid 2-glucoside was 71 to 76% or more. Determination of cysteine, methionine, tryptophan, lysine and collagen peptides, especially cysteine, methionine, tryptophan and lysine in acidic aqueous solutions It can have the effect of stabilizing ascorbic acid 2-glucoside. As a result, it was found that cysteine, methionine, tryptophan, lysine and collagen peptide can be used as a stabilizer for ascorbic acid 2-glucoside in an acidic aqueous medium. By the way, although the detailed data is omitted, the phosphate buffer or the lactic acid buffer other than the citric acid-sodium citrate buffer has different effects, but it is confirmed by the acidity of the amino acid. The stabilization of ascorbic acid 2-glucoside in aqueous media.

On the other hand, when L-carnitine was added (Comparative Sample 8), the residual rate of ascorbic acid 2-glucoside was 68%, which was the same as the control, indicating that the amino acid derivative of L-carnitine was not stabilized in acidity. The effect of ascorbic acid 2-glucoside in aqueous media.

[Example 4] <Method for the stabilization of ascorbic acid 2-glucoside in an acidic water medium other than sugars>

According to the formulation shown in Table 5, in the same manner as in Example 3, (5) cinnamic acid derivative (caffeic acid, ferulic acid) as a present stabilizer was prepared for 3.0 mM ascorbic acid 2-glucoside. (6) catechin or gallic acid derivatives (epicate catechin, gallocatechin, epicatechin gallate, gallic catechin gallate, gallic acid) Any one (corresponding to the test sample 18 to 24 of Table 5) was obtained by the HPLC analysis of the sample containing the concentration of 3.0 mM in the same manner as in Example 3, and stored in a polyester bottle at 40 ° C for 4 weeks before and after storage for ascorbic acid. The residual rate of 2-glucoside was used to verify the effect of the stabilization method of the present invention. Further, as a comparative example, curcumin (corresponding to Comparative Sample 9 of Table 5) prepared as one of polyphenols was stored in an aqueous solution containing 3.0 mM, and then stored under the same conditions, and pH measurement and HPLC analysis were carried out to investigate ascorbic acid 2-glucose. The residual rate of glycosides. The results are shown in Table 5.

As shown in Table 5, for the preservation treatment stored at 40 ° C for 4 weeks, the residual rate of ascorbic acid 2-glucoside in the control group without any stabilizer was 66%, and caffeic acid and ferulic acid were used. , epicatechin, gallocatechin, epicatechin gallate, gallocatechin gallate and gallic acid for ascorbic acid 2-glucoside as shown in Table 5 In the test samples 18 to 24, the residual rate of ascorbic acid 2-glucoside was 71-80% higher, and it was judged that caffeic acid, ferulic acid, epicatechin, gallic catechin, and table. The catechin gallate, gallic catechin gallate, and gallic acid have an effect of stabilizing ascorbic acid 2-glucoside in an acidic aqueous medium. The result indicates a cinnamic acid derivative (caffeic acid, ferulic acid), catechin or gallic acid derivative (epicatechin, gallic catechin, epicatechin gallate, gallic acid) Catechin gallate and gallic acid can be used as a stabilizer for ascorbic acid 2-glucoside in an acidic aqueous medium.

On the other hand, when curcumin was added (Comparative Example 9), the residual ratio of ascorbic acid 2-glucoside was 65%, which was the same value as the control, indicating that curcumin, which is one of polyphenols, was not stabilized in acidic water-based media. of The effect of ascorbic acid 2-glucoside.

[Example 5] <Manufacture of lactic acid bacteria beverage with stabilized ascorbic acid 2-glucoside>

175 parts by mass of defatted powdered milk, 3 parts by mass of ascorbic acid 2-glucoside (Linyuan Manufacturing Co., Ltd., trade name "Asko fresh"), 5 parts by mass of maltotriol as the present stabilizer, and high in milk sucrose 50 parts by mass of powder (Linyuan Manufacturing Co., Ltd., trade name "milk fruit oligomerization") was dissolved in 1,500 parts by mass of water, and sterilized at 65 ° C for 30 minutes, and after cooling at 40 ° C, lactic acid bacteria were implanted according to the conventional method. 30 parts by mass of the starter was cultured at 37 ° C for 8 hours to obtain a lactic acid bacteria beverage containing stabilized ascorbic acid 2-glucoside.

This product not only stabilizes the lactic acid bacteria, but also promotes the proliferation of bifidobacteria and the function of the whole intestine. Since the ascorbic acid 2-glucoside can be stabilized by the present stabilizer, it is difficult to maintain the flavor well for a long period of time. Browning or odorous lactic acid bacteria beverage.

[Embodiment 6] <carbonated drink with juice>

95 parts by mass of mixed water, 10 parts by mass of fructose glucose liquid sugar, 4 parts by mass of grapefruit juice, 2 parts by mass of ascorbic acid 2-glucoside (Linyuan Manufacturing Co., Ltd., trade name "Asko fresh"), and as the present stability 0.2 parts by mass of sorbitol of the chemical agent and 0.8 parts by mass of carbon dioxide were blown to prepare a carbonated beverage (pH 2.7).

Since this product has been stabilized by ascorbic acid 2-glucoside, it is a delicious carbonated beverage which is difficult to produce browning or odor even if it is stored for a long period of time.

[Embodiment 7] <Beer>

Adding a beer brewing kit (Tokyu Hands Shopping Club, trade name "NB Beer Basic Set"), adding ascorbic acid 2-glucoside (100% of the solution for fermentation) (Linyuan Manufacturing Co., Ltd., The product name "Asko fresh") 2 parts by mass and 0.4 parts by mass of palatin as the present stabilizer, and mixed, and the beer is prepared according to the attached manual.

This product has been stabilized due to its ascorbic acid 2-glucoside, so even if it is stored for a long period of time, it is difficult to produce browning or odorous refreshing delicious beer.

[Embodiment 8] <Acetate Beverage>

10 parts by weight of apple cider vinegar, 6 parts by mass of rice vinegar, 2 parts by mass of citric acid, 2 parts by mass of malic acid, 38 parts by mass of isomerized sugar, and sweet enzyme treatment 0.7 parts by mass of chrysanthemum, 1 part by mass of sorbitol, 0.5 parts by mass of apple flavor, 2 parts by mass of apple juice (1/5 concentrated), 2-glucosinolate ascorbic acid (Linyuan Manufacturing Co., Ltd., trade name "Asko fresh") 0.2 mass In an amount of 0.2 parts by mass of tartaric acid as a stabilizer, 100 parts by mass of pure water was added to prepare an acetic acid beverage.

This product is an acetic acid beverage that enhances the action of vitamin C. Since the ascorbic acid 2-glucoside is stabilized by a stabilizer, it is expected that the physiological function from the strengthening of vitamin C can be sustained.

[Embodiment 9] <Liu Orange Juice>

50 parts by mass of orange juice, 0.1 parts by mass of citric acid, 5 parts by mass of granulated sugar, 0.1 parts by mass of ascorbic acid 2-glucoside (Linyuan Manufacturing Co., Ltd., trade name "Asko fresh"), and ferulic acid as a stabilizer 0.1 parts by mass, a suitable amount of fragrant and 46 parts by weight of water, and secondly, according to a common method, after being sterilized in a container, an orange juice product is obtained.

This product is stabilized by the stabilization of ascorbic acid 2-glucoside, which is enhanced by the action of vitamin C. It is a natural color of orange, which has a orange flavor and is not easily deteriorated over a long period of time. And the decomposition of orange juice.

[Embodiment 10] <Grapefruit Jelly>

6 parts by mass of erythritol as a stabilizer, 1.2 parts by weight of tranquilizer, 1 part by mass of grapefruit grit, 0.9 parts by mass of pH adjuster, 0.5 parts by mass of grapefruit juice (1/6 concentrated), ascorbic acid 2 - 2 parts by mass of glucoside (product name "Asko fresh" of Linhara Manufacturing Co., Ltd.), 0.04 parts by mass of enzyme-treated stevia, and 0.01 parts by mass of safflower yellow, 100 parts by mass of pure water was added to prepare grapefruit jelly.

This product stabilizes ascorbic acid 2-glucoside by a tranquilizer, which is a jelly that is enhanced by the action of vitamin C, and is expected to continue to exert physiological functions with vitamin C by ingestion.

[Example 11] <Save material>

19 parts by mass of ascorbic acid 2-glucoside (trade name "Asko fresh" of Hayashibara Manufacturing Co., Ltd.), 3 parts by mass of tartaric acid as a stabilizer, 5 parts by mass of sodium carbonate, and trehalose (product of Linyuan Manufacturing Co., Ltd.) 75 parts by mass of "Treha" was dissolved in 1000 parts by mass of water to prepare a solution-like preservation material.

This product is used as a preservative for the composition of food and beverage. It can be used by coating, dipping, spraying, injecting and mixing. Moreover, since this product contains trehalose, it can suppress the sourness or pungent taste of the ascorbic acid 2-glucoside which is a main component of a preservation material. Moreover, since the ascorbic acid 2-glucoside is stabilized by the stabilizer, the odor can be maintained even after long-term storage. Inhibition.

[Embodiment 12] <lotion>

8 parts by mass of squalane, 0.3 parts by mass of polyoxyethylene sorbitol tetraoleate, 34 parts by mass of sorbitol, and 0.001 parts by mass of amylopectin (trade name "Puruland" of Linyuan Manufacturing Co., Ltd.), ethyl 1 part by mass of alcohol, 0.5 parts by mass of sorbitol as a stabilizer, 2 parts by mass of ascorbic acid-2-glucoside (trade name "AA2G" of Linyuan Manufacturing Co., Ltd.), 0.1 mass part of astringent (rhomite), The lotion is prepared by mixing the preservative, the fragrance and the purified water in an appropriate amount.

This product is a lotion that has an excellent long-term preservation property for skin tension or color because it is suitable for the skin to be stabilized against ascorbic acid 2-glucoside.

[Example 13] <Beauty solution>

3 parts by mass of sorbitan sorbitan, 10 parts by mass of decamethylcyclopentaoxane, 8 parts by mass of isodecyl acid isodecyl, 0.5 parts by weight of perfluoropolyether, and 0.1 parts by mass of perfume 3 parts by mass of glycerin, 10 parts by mass of 1,2-propanediol, 3 parts by mass of ascorbic acid 2-glucosamine (trade name "AA2G" of Linyuan Manufacturing Co., Ltd.), and sodium citrate 0.5 mass A cosmetic solution is prepared in an amount of 0.5 parts by mass of tartaric acid as a stabilizer and an appropriate amount of water.

This product has been stabilized by ascorbic acid 2-glucoside, so it can be used as a sunscreen for long-term preservation and to prevent spots. Use of freckles, beautifying skin, and whitening beauty lotion.

[Embodiment 14] <emulsion>

0.5 parts by mass of polyoxyethylene behenyl ether, 1 part by mass of tetraoleic acid polyoxyethylene sorbitol, 1 part by mass of lipophilic glyceryl monostearate, 0.5 parts by mass of pyruvic acid, 0.5 parts by mass of behenyl alcohol, 1 part by weight of avocado oil, 1 part by mass of ascorbic acid 2-glycoside (trade name "AA2G" of Linyuan Manufacturing Co., Ltd.), 1 part by mass of erythritol as a stabilizer, vitamin E and preservative In the usual method, it is dissolved by heating, and 1 part by mass of L-lactate, 5 parts by mass of 1,3-butanediol, 0.1 part by mass of a carboxyvinyl polymer, and 85.3 parts by mass of purified water are added thereto, and further emulsified by a homogenizer, and further added. A suitable amount of perfume is stirred and mixed to produce an emulsion containing stabilized ascorbic acid 2-glucoside.

This product has been stabilized by ascorbic acid 2-glucoside, so it can be used as a sunscreen to prevent spots. Freckles, beautifying the skin, whitening lotion, can be used even if stored for a long period of time.

[Example 15] <Cosmetic Cream>

2 parts by mass of polyoxyethylene glycol monostearate, 5 parts by mass of self-emulsified monostearic acid glycerin, and 2 parts by mass of ascorbic acid 2-glucoside (Linyuan Manufacturing Co., Ltd., trade name "AA2G"), as stability 2 parts by mass of galactitol, 1 part by mass of paraffin wax, 10 parts by mass of tricaprylic glyceryl group and an appropriate amount of preservative, which are dissolved by heating according to a conventional method, and 2 parts by mass of L-lactic acid and 1,3-butyl are added thereto. 5 parts by mass of the diol and 66 parts by mass of purified water were emulsified by a homogenizer, and an appropriate amount of the flavor was further added and stirred to prepare a cream.

This product has anti-oxidation, and ascorbic acid 2-glucoside has been stabilized, it can be used as a high-quality sunscreen to prevent spots. Freckles, beautifying the skin, and whitening make-up cream can be used even if stored for a long period of time.

[Example 16] <Bathing agent>

21 parts by mass of sodium lactate, 8 parts by mass of sodium pyruvate, 5 parts by mass of ascorbic acid 2-glucoside (Linyuan Manufacturing Co., Ltd., trade name "AA2G"), 1 part by weight of ferulic acid as a stabilizer, and 40 mass of ethanol The mixture was mixed with 26 parts by mass of purified water and an appropriate amount of coloring materials and perfume to prepare a bathing agent.

This product can be diluted as 100 in the hot water of the bath to 10,000 times the use of bathing agent. Moreover, since this product has been stabilized by ascorbic acid 2-glucoside, it has a beautifying skin or whitening effect for a long period of time, and can be suitably diluted and used as a lotion water, lotion, and the like.

[Example 17] <liquid agent>

6 parts by mass of sodium chloride, 0.3 parts by mass of potassium chloride, 0.2 parts by mass of calcium chloride, 3.1 parts by mass of sodium lactate, 44 parts by mass of trehalose (Linyuan Manufacturing Co., Ltd., trade name "Treha"), as a stabilizer 2 parts by mass of palladium and 0.5 parts by mass of ascorbic acid 2-glucoside (trade name "AA2G" of Linyuan Manufacturing Co., Ltd.) are dissolved in 1,000 parts by weight of purified water, subjected to membrane filtration according to the usual method, and then sterilized in plastic. A liquid preparation was obtained after each of the containers was filled with 30 ml.

This product is a replenishing effect of vitamins, calories and minerals. It is used as an eye drop or injection for the stabilization of ascorbic acid 2-glucoside for the treatment of diseases caused by eye fatigue or severe muscle stiffness.

[Embodiment 18] <oral gavage nutrient>

20 parts by mass of crystalline α-maltose, 1.1 parts by mass of glycine, 0.18 parts by mass of sodium glutamate, 1.2 parts by mass of salt, and citric acid 1 were prepared. Parts by mass, 0.4 parts by mass of calcium lactate, 0.1 parts by mass of magnesium carbonate, 0.1 parts by mass of ascorbic acid 2-glucoside (Linyuan Manufacturing Co., Ltd., trade name "AA2G"), 0.1 parts by mass of sucrose as a stabilizer, and thiamine a complex of 0.01 parts by mass and 0.01 parts by mass of riboflavin. 24 g of each complex was filled in a laminated aluminum pouch, and after heat sealing, an oral gavage nutrient was prepared.

The oral gavage nutrient is dissolved in a bag of about 100~500ml of sterilized water, and is used as an oral nutrient replenishment solution for ascorbic acid 2-glucoside or a nutrient replenishment solution for nasal cavity, stomach, intestine, etc. use.

[Embodiment 19] <Ointment>

Will be sodium acetate. 1 part by mass of the trihydrate salt, 4 parts by mass of calcium lactate and 10 parts by mass of glycerin are uniformly mixed, and the mixture is added to 50 parts by mass of petrolatum, 10 parts by mass of wood wax, 10 parts by mass of lanolin, 14.5 parts by mass of sesame oil, and 2 - ascorbic acid. A mixture of 1 part by mass of glucoside (trade name "AA2G" of Linyuan Manufacturing Co., Ltd.) and 1 part by mass of maltotriol as a stabilizer was further uniformly mixed to produce an ointment.

This product has anti-oxidation energy, and its anti-ascorbic acid 2-glucoside has high stability even in acidic water-based media. It can be used as a high-quality sunscreen, beautifying skin agent, whitening agent, etc., and further as a healing agent for trauma and fire injury. And advantageously used.

[Example 20] <Liquid toothpaste>

10 parts by mass of glycerin, 3 parts by mass of 1,3-propanediol, 5 parts by mass of low molecular weight cold weather, 0.2 parts by mass of polyoxyethylene hardened castor oil, 0.5 parts by mass of Lipitor as stabilizer, and 2-glucose ascorbate 1 part by mass of glycosides (trade name "AA2G" of Linyuan Manufacturing Co., Ltd.), 0.05 parts by mass of cetylpyridinium chloride, 0.05 parts by mass of 1-menthol, 0.05 parts by mass of tranexamic acid, 0.02 by mass of sodium saccharin A liquid toothpaste (pH 4.5) was prepared by mixing 0.01 parts by mass of methylparaben, 0.05 parts by mass of perfume, and an appropriate amount of citric acid according to a usual method.

This product has high stability of ascorbic acid 2-glucoside and can be advantageously used as a toothpaste with excellent antibacterial action.

[Example 21] <安定化剂>

The saccharide containing a saccharide-like α,α-trehalose-based saccharide derivative (trade name "Hello index" of Linyuan Manufacturing Co., Ltd.) 70 parts by mass of the saccharide-containing α,α-trehalose-containing saccharide derivative was dissolved in 200 parts by mass of water. The powder stabilizer is prepared by spray drying according to a conventional method.

This product can be advantageously used as a stabilizer for improving the stability of ascorbic acid 2-glucoside contained in an acidic aqueous medium. This product pair An acidic aqueous medium containing ascorbic acid 2-glucoside starting from a food or drink can be advantageously used by mixing. By coexisting the present stabilizer, the ascorbic acid 2-glucoside can be stabilized, so that ascorbic acid 2-glucoside can be stably stored for a long period of time in an acidic aqueous medium.

[Industrial availability]

The present invention is capable of remarkably improving the stability of ascorbic acid 2-glucoside in an acidic aqueous medium by adding a specific compound to ascorbic acid 2-glucoside. Further, an acidic aqueous medium composition using the method and a method for producing the same are provided. With the expansion of the use range of ascorbic acid 2-glucoside, the industrial usefulness of the present invention has also increased.

Claims (19)

A method for the stabilization of 2-O-α-D-glycosyl-L-ascorbic acid in an acidic aqueous medium, characterized in that 2-O-α-D-glycosyl-L-ascorbic acid is selected from the following ( 1) ~ (8) one or more of the stabilizers coexisted; (1) a carbon number of 4 to 6 sugar alcohol; (2) glycosyl fructose or its sugar alcohol; (3) glucose three Sugar sugar alcohol; (4) sugar-based trehalose; (5) cinnamic acid derivative; (6) catechin or gallic acid derivative; (7) tartaric acid or a salt thereof; and (8) amino acid or peptide . The method of stabilization of claim 1, wherein the (1) carbon sugar having 4 to 6 carbon atoms is one or more selected from the group consisting of erythritol, Lipitor, sorbitol, and galactitol. The method for stabilization according to claim 1, wherein the (2) glycosyl fructose or a sugar alcohol thereof is one or more selected from the group consisting of sucrose and palatin. The method for stabilization according to claim 1, wherein the sugar alcohol of the aforementioned (3) glucose trisaccharide is maltotriitol. The method of claim 1, wherein the (4) glycosyl trehalose is one or more selected from the group consisting of glycosyl trehalose, maltosyl trehalose, and maltotriosyl trehalose. The method for stabilization of claim 1, wherein the aforementioned (5) cinnamic acid The derivative is one or two selected from the group consisting of caffeic acid and ferulic acid. The method for stabilization according to claim 1, wherein the (6) catechin or gallic acid derivative is one or two selected from the group consisting of gallocatechinin and gallocatechin gallate. . The method for stabilization according to claim 1, wherein the aforementioned (7) tartaric acid or a salt thereof is tartaric acid. The stabilization method according to claim 1, wherein the (8) amino acid or peptide is one or more selected from the group consisting of cysteine, methionine, tryptophan, lysine, and collagen peptide. . The stabilization method according to any one of claims 1 to 9, wherein the 2-O-α-D-glycosyl-L-ascorbic acid is coexisted with the aforementioned stabilizer at a molar ratio of 1:0.01 to 1:500. By. The stabilization method according to any one of claims 1 to 10, wherein the pH of the acidic aqueous medium is from 2.0 to 5.0. A method for producing an aqueous medium acidic composition containing stabilized 2-O-α-D-glycosyl-L-ascorbic acid, which comprises containing 2-O-α-D-glycosyl groups in an acidic aqueous medium -L-ascorbic acid and a step of coexisting with a stabilizer selected from one or more of the following (1) to (8); (1) a sugar alcohol having 4 to 6 carbon atoms; (2) Glycosyl fructose or a sugar alcohol thereof; (3) a sugar alcohol of glucose trisaccharide; (4) a sugar-based trehalose; (5) a cinnamic acid derivative; (6) a catechin or a gallic acid derivative; (7) tartaric acid or a salt thereof; and (8) an amino acid or a peptide. The method of claim 12, wherein the mixing ratio of 2-O-α-D-glycosyl-L-ascorbic acid to one or more selected from the group consisting of the stabilizers is 1:0.05 to 1 molar ratio. :20. The production method of claim 12 or 13, wherein the pH of the acidic aqueous medium is from 2.0 to 5.0. An acidic aqueous medium composition containing 2-O-α-D-glycosyl-L-ascorbic acid, which is obtained by the production method according to any one of claims 12 to 14. The composition of claim 15 which is a beverage. The composition of claim 15 is a preservation material. The composition of claim 15 which is a lotion. An stabilizer for improving the stability of 2-O-α-D-glycosyl-L-ascorbic acid in an acidic aqueous medium, characterized in that it contains one or two selected from the following (1) to (8) Any of the above as an active ingredient: (1) a sugar alcohol having 4 to 6 carbon atoms; (2) a glycosyl fructose or a sugar alcohol thereof; (3) a sugar alcohol of glucose trisaccharide; (4) a sugar-based trehalose; a cinnamic acid derivative; (6) a catechin or a gallic acid derivative; (7) tartaric acid or a salt thereof; (8) Amino acids or peptides.