Stabilizer for emulsion composition

Abstract

The present invention addresses the problem of providing a stabilizer and a stabilization method for an emulsion composition obtained by emulsification with a nonionic surfactant. The problem is solved by providing: a stabilizer for an emulsion composition obtained by emulsification with a nonionic surfactant, the stabilizer containing glycosyl naringenin as an active ingredient; and a stabilization method for an emulsion composition obtained by emulsification with a nonionic surfactant, the method including a step in which the stabilizer containing glycosyl naringenin as an active ingredient is mixed with and / or incorporated into a raw material for the emulsion composition, an intermediate thereof, and / or the produced emulsion composition.

Description

[Technical Field]

[0001] The present invention relates to a stabilizer for an emulsion composition, and more particularly to a stabilizer and a method for stabilizing an emulsion composition that contains glycosylnaringenin as an active ingredient and is emulsified using a nonionic surfactant. [Background technology]

[0002] An emulsified composition (emulsion) generally refers to a dispersion solution in which both the dispersoid and the dispersion medium are liquid, and usually refers to a water-in-oil or oil-in-water dispersion solution composed of an oily component and an aqueous component. A surfactant is generally used to emulsify the oily component and the aqueous component, and usually, when a large amount of surfactant is added, the emulsified state of the emulsified composition is maintained stably for a long period of time.

[0003] Emulsion compositions are used in a wide range of fields, including foods, cosmetics, quasi-drugs, and pharmaceuticals. However, particularly in emulsion compositions in the form of cosmetics, quasi-drugs, pharmaceuticals, etc. that are applied directly to the skin of humans or animals, a high content of surfactants can cause safety issues such as skin irritation, as well as physical property issues such as a deterioration in the feel when used. Against this background, there is a demand for a reduction in the surfactant content in emulsion compositions.

[0004] For example, Patent Document 1 discloses a method for improving the emulsifying power and usability of an emulsion composition without adding a surfactant by incorporating an alkyl-modified carboxy polymer and a sugar into the emulsion composition. Patent Document 2 discloses a method for controlling viscosity by adding a water-soluble synthetic polymer such as an acrylic acid-based polymer to the emulsion composition, thereby improving the stability and usability of the emulsion composition. Patent Document 3 discloses a method for improving the emulsifying power of an emulsion composition by incorporating an alkyl-esterified compound of a flavonoid glycoside into the emulsion composition. Patent Document 4 discloses a method for improving the emulsifying power and usability of an emulsion composition without adding a surfactant by incorporating a polyphenol glycoside into the emulsion composition.

[0005] However, when alkyl-modified carboxy polymers and sugars were combined, the skin irritation problem was resolved, but the emulsion stability was not fully satisfactory. Furthermore, when acrylic acid-based polymers were combined, the emulsion stability problem was resolved, but the feel upon use was not fully satisfactory. Regarding alkyl ester compounds of flavonoid glycosides, they essentially acted as surfactants themselves, and the feel upon use was also not fully satisfactory. Regarding polyphenol glycosides under surfactant-free conditions, the emulsion stability was not fully satisfactory, and further new technologies are desired. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Publication No. 8-217624 [Patent Document 2] Japanese Patent Application Laid-Open No. 2008-106043 [Patent Document 3] Japanese Patent Application Publication No. 2019-141825 [Patent Document 4] Japanese Patent Application Laid-Open No. 2012-82183 Summary of the Invention [Problem to be solved by the invention]

[0007] The present invention has been made in view of the above-mentioned conventional techniques, and an object of the present invention is to provide a stabilizer and a method for stabilizing an emulsion composition emulsified using a nonionic surfactant. [Means for solving the problem]

[0008] In order to solve the above problems, the inventors have made extensive research efforts and have unexpectedly discovered that by mixing and / or adding glycosyl naringenin to an emulsion composition emulsified using a nonionic surfactant, the emulsion state of the emulsion composition can be maintained stably for a long period of time, thereby completing the present invention.

[0009] That is, the present invention solves the above-mentioned problems by providing a stabilizer for an emulsion composition emulsified with a nonionic surfactant, which contains glycosyl naringenin as an active ingredient.The present invention also solves the above-mentioned problems by providing a method for stabilizing an emulsion composition emulsified with a nonionic surfactant, which comprises the step of mixing and / or incorporating a stabilizer containing glycosyl naringenin as an active ingredient into raw materials, intermediates, and / or the emulsion composition produced. [Effects of the Invention]

[0010] The present invention provides an emulsion composition having excellent stability over time. Furthermore, the surfactant content can be reduced, which improves formulation flexibility and reduces the risk of skin irritation, thereby improving safety.

[0011] The stabilizer of the present invention can be applied to humans or animals on a daily basis, safely, easily, and continuously without causing discomfort, and can be provided industrially at low cost. Such a stabilizer of the present invention is useful as a stabilizer that imparts stability to formulations. DETAILED DESCRIPTION OF THE INVENTION

[0012] The present invention relates to a stabilizer and a method for stabilizing an emulsion composition containing glycosylnaringenin as an active ingredient and emulsified using a nonionic surfactant.

[0013] "Glycosylnaringenin" as used herein is a type of flavanone and is a general term for glycosides whose aglycon is "naringenin," which has the structure shown in Chemical Formula 1 below. Representative compounds encompassed by "glycosylnaringenin" include "naringin" (Chemical Formula 2 below), which has a structure in which neohesperidose (α-rhamnosyl(1→2)glucose) is beta-bonded to the 7-OH group of naringenin, and "3"-α-glucosylnaringin" (Chemical Formula 3 below), which has a structure in which glucose is α-bonded to the 3-OH group (3" position) of the glucose residue in the neohesperidose of naringin.

[0014] Chemical formula 1: [ka]

[0015] Chemical formula 2: [ka]

[0016] Chemical formula 3: [ka]

[0017] Furthermore, the term "glycosylnaringenin" as used herein also includes "4'-α-glucosylnaringin" (chemical formula 4 below), which has a structure in which glucose is α-bonded to the OH group at the 4' position of naringin, and "3"-α-,4'-α-diglucosylnaringin" (chemical formula 5 below), which has a structure in which glucose is α-bonded to the OH groups at the 3' and 4' positions of naringin, as well as "purunin" (chemical formula 6 below), which has a structure in which glucose is β-bonded to the OH group at the 7' position of naringenin, and "narirutin" (chemical formula 7 below), which has a structure in which rutinose (α-rhamnosyl(1→6)glucose) is β-bonded to the OH group at the 7' position of naringenin.

[0018] Chemical formula 4: [ka]

[0019] Chemical formula 5: [ka]

[0020] Chemical formula 6: [ka]

[0021] Chemical formula 7: [ka]

[0022] Furthermore, the term "glycosylnaringenin" as used herein also includes α-maltosylnaringin, α-maltotriosylnaringin, α-maltotetraosylnaringin, α-maltopentaosylnaringin, α-glucosylprunin, α-maltosylprunin, α-maltotriosylprunin, α-maltotetraosylprunin, α-maltopentaosylprunin, α-glucosylnaringenin, α-maltosylnaringin, α-maltotriosylnaringin, α-maltotetraosylprunin, α-maltopentaosylprunin, α-glucosylnaringenin, α-maltosylnaringin, α-maltotriosylnaringin, α-maltotetraosylnaringin, α-maltopentaosylnaring ... and the like, which are obtained by further binding glycosyl groups to the above-mentioned prunin, naringin, 3"-α-glucosylnaringin, narirutin, 4'-α-glucosylnaringin, 3"-α-,4'-α-diglucosylnaringin.

[0023] These glycosyl naringenins can be prepared by enzymatic methods. Fermentation and chemical synthesis can also be used, if necessary. When producing glycosyl naringenin, if economic efficiency is an issue, an enzymatic method using glycosyltransferases is advantageous. For example, methods disclosed in Japanese Patent Laid-Open Publication Nos. 04-13691 and 2007-284393 involve the action of glycosyltransferases, such as α-glucosidase, cyclomaltodextrin glucanotransferase, and α-amylase, on naringin in the presence of α-glucosyl sugar compounds, such as partial starch hydrolysates and maltooligosaccharides. This method typically produces a series of 3"-α-glycosylnaringin with a degree of glucose polymerization at the transferred moiety ranging from 1 to 5, in high yield. 3"-α-Glucosylnaringin can also be advantageously prepared by treating this series of 3"-α-glycosylnaringin with glucoamylase.

[0024] The degree of glucose polymerization of the glycosyl groups in glycosyl naringenin can be appropriately reduced by treating glycosyl naringenin with glucoamylase. On the other hand, the degree of glucose polymerization of the glycosyl groups in glycosyl naringenin can be advantageously increased by treating glycosyl naringenin with a glycosyltransferase such as cyclomaltodextrin glucanotransferase in the presence of a glycosyl donor such as a partial starch hydrolysate. Furthermore, if necessary, glycosyl naringenin can be advantageously modified by further transferring monosaccharides, disaccharides, oligosaccharides, or polysaccharides other than D-glucose to glycosyl naringenin.

[0025] Prunin can be prepared by treating naringin with rhamnosidase to remove rhamnose, as disclosed in Japanese Patent Application Laid-Open No. 2007-284393. Narirutin can be prepared by α-1,6-transferring rhamnose to prunin. These glycosyl naringins can also be prepared by fermentation, chemical degradation, or synthesis, as needed.

[0026] In the present invention, glycosyl naringenin can be used regardless of its origin, production method, purity, etc., as long as it can stabilize the emulsion composition. It does not necessarily have to be highly purified. As long as its effectiveness and safety are not affected, it may be in the form of an enzyme reaction solution itself, an unseparated composition containing glycosyl naringenin and other substances specific to the preparation method, or a partially purified or highly purified form. The purity of glycosyl naringenin used in the stabilizer for the emulsion composition of the present invention is typically 20% by mass or more, preferably 40% by mass or more, and more preferably 50 to 99.99% by mass, based on the solid content. High-purity products may also be high-purity glycosyl naringenin obtained through a crystallization process.

[0027] As described above, the glycosyl naringenin contained in the stabilizer of the present invention is typically in the form of a composition containing, as its main component, one or more compounds having a naringenin skeleton selected from (1) naringin and α-glycosyl naringin (e.g., α-glucosyl naringin), i.e., a glycosyl naringenin mixture, depending on its manufacturing method. It may also contain trace components such as (2) flavonoids, such as diosmin and neoponcirin, and (3) salts, which are derived from the raw materials used for manufacturing the stabilizer or are thought to be by-produced during the manufacturing process. The glycosyl naringenin mixture may also contain naringenin, the aglycone, to the extent that the desired effects of the present invention are not impaired. Furthermore, the stabilizer of the present invention may contain naringenin whose dispersibility in solvents such as water has been improved by known physical techniques, such as microparticulation, or known chemical techniques, such as particle coating or immobilization on microcarriers, to the extent that the desired effects of the present invention are not impaired.

[0028] The stabilizer of the present invention may contain a single compound within the glycosylnaringenin category; however, it is preferable to contain two or more compounds within the glycosylnaringenin category, as this synergistically enhances the stabilizing effect of glycosylnaringenin on emulsion compositions. From the standpoint of the strength of the emulsion stabilizing effect and high solubility in water, the stabilizer of the present invention preferably contains α-glycosylnaringin as the glycosylnaringenin, more preferably α-glucosylnaringin as the α-glycosylnaringin. Furthermore, stabilizers containing one or more α-glucosylnaringin selected from 3′-α-monoglucosylnaringin, 3′-α-,4′-α-diglucosylnaringin, and 4′-α-glucosylnaringin are preferred, as this more significantly achieves the desired effect of the present invention, i.e., the stabilizing effect on emulsion compositions.

[0029] The amount of glycosyl naringenin in the stabilizer of the present invention should be appropriately selected depending on the specific formulation and the balance with other ingredients, so long as the desired effects of the present invention are obtained. Although not particularly limited, the total glycosyl naringenin content per dry solid is typically 50% to 100% by mass, preferably 60% to 100% by mass, more preferably 70% to 100% by mass, even more preferably 80% to 100% by mass, and even more preferably 85% to 100% by mass. The upper limit of the glycosyl naringenin content per dry solid to be contained in the stabilizer of the present invention is typically 99% by mass, which allows for inexpensive and easy production in relatively large quantities industrially. To provide it at an even lower cost, the upper limit may be as low as 80% by mass, and even lower, down to 60% by mass or less. However, if the glycosyl naringenin content per dry solid of the glycosyl naringenin is low, it will inevitably be used in larger amounts than those with higher contents, which will result in complicated operations and poor handling. Therefore, the lower limit of the glycosyl naringenin content is generally 10% by mass or more, preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, and even more preferably 50% by mass or more.

[0030] In a preferred embodiment, the stabilizer of the present invention contains α-glycosylnaringenin as the glycosylnaringenin, more preferably α-glucosylnaringin as the glycosylnaringenin. In this case, the preferred content of α-glucosylnaringin in the glycosylnaringenin is typically 10% to 100% by mass, preferably 20% to 100% by mass, and more preferably 30% to 100% by mass, based on the dry solids. Furthermore, the upper limit of the α-glucosylnaringin content in the glycosylnaringenin contained in the stabilizer of the present invention is generally 100% by mass or less, as described above. However, from the perspective of providing the stabilizer of the present invention at a lower cost, a lower content of 99% by mass or less, more preferably 95% by mass or less, and even more preferably 90% by mass or less, which can be provided industrially in relatively large quantities at low cost and with ease, may be used. Furthermore, for the same reasons as for the glycosylnaringenin content in the glycosylnaringenin mixture described above, the lower limit of the α-glucosylnaringenin content is typically 10% by mass or more, preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, and even more preferably 50% by mass or more.

[0031] The emulsion compositions to which the stabilizer of the present invention can be added or contained are not particularly limited as long as they are emulsion compositions emulsified using a nonionic surfactant, and may be compositions for topical skin application or oral administration. The stabilizer of the present invention functions as a stabilizer for these emulsion compositions when added to or mixed with these emulsion compositions. The glycosyl naringenins used in the present invention possess, in addition to emulsion stabilizing activity, elastase activity inhibitory activity, anti-aging activity, anti-wrinkle (wrinkle improvement / prevention), anti-sagging (sagging improvement / prevention), slimming activity, blood circulation promoting activity, lipase activity inhibitory activity, radical scavenging activity, anti-inflammatory activity, whitening activity, lipid peroxide reduction in the body, inhibition of ascorbic acid reduction in the body, and active oxygen scavenging activity. Therefore, emulsion compositions, including compositions for topical skin application, containing the stabilizer of the present invention preferably contain an effective amount of one or more glycosyl naringenins having the above-mentioned activities.

[0032] The proportion of glycosyl naringenin in various emulsion compositions containing the stabilizer of the present invention is typically 0.001 to 20.0% by mass, preferably 0.01 to 10.0% by mass, and particularly preferably 0.05 to 5.0% by mass, based on the total mass of the composition. If the amount is less than 0.001% by mass based on the total mass of the emulsion composition, the emulsion stabilizing effect of glycosyl naringenin may not be fully exerted, which is undesirable. Conversely, if the amount exceeds 20.0% by mass, the emulsion stabilizing effect of glycosyl naringenin may not be fully exerted, which may undesirably impair the physical properties and pharmacological effects originally required of the emulsion composition to be incorporated. Furthermore, the blending ratio of glycosylnaringenin in various emulsion compositions is typically 0.002 to 40.0 parts by mass, preferably 0.02 to 20.0 parts by mass, and particularly preferably 0.1 to 10.0 parts by mass, of glycosylnaringenin relative to 1 mass of nonionic surfactant in the composition. If this blending amount is less than 0.002 parts by mass relative to the total mass of the emulsion composition, the emulsion stabilizing effect of glycosylnaringenin may not be fully exerted, which may be undesirable. Conversely, if it exceeds 40.0 parts by mass, the emulsion stabilizing effect of glycosylnaringenin may not be fully exerted, which may be undesirable, as it may impair the physical properties and pharmacological effects originally required of the emulsion composition to be blended.

[0033] Examples of "nonionic surfactants" as used herein include ester types (polyhydric alcohol types) such as glycerin fatty acid esters, sorbitan fatty acid esters, and sucrose fatty acid esters, ether types such as polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, and polyoxyethylene polyoxypropylene glycols, ester-ether types such as fatty acid polyethylene glycols and fatty acid polyoxyethylene sorbitan, alkanolamide types such as fatty acid alkanolamides, and alkyl polyglucosides. The emulsion compositions targeted by the stabilizer of the present invention usually contain one or more of the above nonionic surfactants.

[0034] The mechanism by which glycosylnaringenin, contained as an active ingredient in the stabilizer of the present invention, exerts its stabilizing function on emulsion compositions emulsified using nonionic surfactants is not clear, but it is presumed that glycosylnaringenin enhances the action of the nonionic surfactant.

[0035] The stabilizer of the present invention is expected to not only improve the emulsion stability of emulsion compositions, but also to enhance the effects of nonionic surfactants in addition to the various physical property improving properties inherent to glycosylnaringenin contained as an active ingredient. Therefore, examples of emulsion compositions to which the stabilizer of the present invention can be added or contained include not only stabilizers, emulsifying aids, and physical property improvers, but also texture improvers, gloss improvers, water retention agents, humectants, viscosity improvers, quality improvers, excipients, adhesives, osmotic pressure regulators, flavor improvers, haze regulators, precipitation inhibitors, shelf life improvers, retention improvers, hardening regulators, flow regulators, viscoelasticity improvers, adhesion improvers, and the like. Examples of such agents include antioxidants, anti-browning agents, syneresis inhibitors, molding agents, shape retaining agents, refrigeration-resistant agents, freeze-resistant agents, ice crystal stabilizers, intestinal regulators, agents for improving smoothness in the throat, cleaning agents, detergents, dentifrices, fabric softeners, antistatic agents, disinfectants, solubilizing agents, dispersants, water repellents, foaming agents, foaming agents, antifoaming agents, moisturizing agents, penetrating agents, lubricants, surface treatment agents, spreading agents, lubricants, rust inhibitors, surface modifiers, flocculants, solubilizing agents, anti-fogging agents, lubricants, release agents, vulcanization accelerators, deinking agents, dust prevention agents, agents for treating oil spills, and fire extinguishing agents, and they can be advantageously used in various compositions such as foods, snacks, feed, cosmetics, quasi-drugs, pharmaceuticals, and industrial products.

[0036] The stabilizer of the present invention can be blended with known ingredients depending on the specific form of the composition to be added or mixed into. That is, when the stabilizer is in a form to be added to or contained in a composition for external use on skin or a composition for oral administration, one or more ingredients that can normally be used in such compositions can be blended within a range that does not impair the intended effect of the present invention.

[0037] When the emulsion composition containing the stabilizer of the present invention is a composition for external use on the skin, there is no particular limitation on the dosage form of the stabilizer to be contained, and the stabilizer of the present invention can be used in various dosage forms, such as an aqueous solution system, a solubilized system, an emulsion system, a dispersion system, a solid system, etc. Furthermore, there is no particular limitation on the form of the composition for external use on the skin to be contained by addition or mixing, and it is not restricted by legal classifications such as cosmetics, quasi-drugs, and pharmaceuticals under the Pharmaceutical and Medical Device Act, etc. As used herein, the term "topical skin composition" refers to cosmetics, quasi-drugs, and pharmaceuticals that are applied to the skin, outer skin such as the lips and scalp, and the oral cavity. Specific examples of such compositions include ointments, creams, emulsions, essences, beauty serums, toners, lotions, jellies, gels, packs, shampoos, rinses, hair treatments, masks, mascara, eyeliners, hair growth agents, hair growth agents, lipsticks, lip glosses, foundations, blushers, eye shadows, soaps, body soaps, bath additives, dentifrices, mouth fresheners, mouth freshening films, mouthwashes, and gargles.

[0038] The stabilizer of the present invention can also be added or mixed into topical skin compositions such as anti-wrinkle topical skin preparations, slimming topical skin preparations, blood circulation promoting topical skin preparations, lipase activity inhibiting topical skin preparations, anti-inflammatory topical skin preparations, radical scavenging topical skin preparations, whitening topical skin preparations, topical skin preparations for reducing lipid peroxides in the body, topical skin preparations for inhibiting reduction of ascorbic acid in the body, anti-aging topical skin preparations, topical skin preparations for preventing dullness of the skin or lips, topical skin preparations for the scalp, topical skin preparations for hair, anti-inflammatory topical skin preparations, makeup cosmetics, and topical skin preparations for massage, as long as they are emulsion compositions emulsified with a nonionic surfactant, as an agent for stabilizing the emulsion state.

[0039] Even when the stabilizer of the present invention is added to or mixed with an orally ingested composition, such as an emulsified composition, and used, as long as the composition is emulsified with a nonionic surfactant, the same effects can be obtained as when the stabilizer is added to or mixed with an external skin composition, also an emulsified composition, and used. The formulation of the orally ingested composition is not particularly limited, and the desired effects can be obtained by adding the stabilizer of the present invention to various formulations, such as aqueous solutions, solubilized systems, emulsions, dispersions, and solid systems. Furthermore, the form of the orally ingested composition to which the stabilizer of the present invention is added or mixed is not particularly limited, and is not limited to classifications such as foods and beverages, supplements, foods for specified health uses, functional foods, health foods, health supplements, health functional foods, dietary supplements, foods with nutritional claims, foods with functional claims, foods for specified health uses, foods for special dietary uses, quasi-drugs, and pharmaceuticals. Furthermore, the term "composition for oral ingestion" as used herein refers to a substance to be orally ingested as a food or beverage, etc., and includes those used for purposes such as whitening, skin beautification, slimming, promoting blood circulation, anti-inflammation, anti-aging, anti-wrinkle, anti-sagging, reducing lipid peroxides in the body, removing radicals, removing active oxygen, inhibiting the reduction of ascorbic acid in the body, reducing body fat, reducing visceral fat, recovering from fatigue, and reducing stress. When the stabilizer of the present invention is added to or mixed with an emulsion composition for oral ingestion to contain the stabilizer, the total amount of glycosylnaringenin is 0.001 to 20.0% by mass, preferably 0.01 to 10.0% by mass, and particularly preferably 0.05 to 5.0% by mass. However, when glycosylnaringenin is used for the purpose of enhancing the various physiological effects described above, the stabilizer of the present invention itself can also be advantageously used as the composition for oral ingestion. When an oral composition containing the stabilizer of the present invention is orally ingested, there is no particular limit to the daily intake amount as long as the emulsion stabilizing effect and other physiological functions are exerted. However, for a person weighing 50 kg, the daily intake amount should generally be 0.005 to 10 g, preferably 0.01 to 5 g, and particularly preferably 0.02 to 2.5 g of glycosylnaringenin in total.

[0040] The present invention will be further illustrated by the following experiments.

[0041] <Experiment 1: Effects of glycosylnaringenin and various surfactants on emulsion stability of emulsion compositions> Using a 3'-α-glucosylnaringin composition as glycosylnaringenin, emulsion compositions containing various surfactants were prepared, and tests were conducted to evaluate the emulsion stability.

[0042] <Experiment 1-1: Preparation of 3'-α-glucosylnaringin composition> Glycosylnarigenin was prepared according to the method described in Example 1 of JP-A-2002-199896. That is, 50 parts by mass of naringin and 200 parts by mass of dextrin DE8 were dissolved by heating in 500 parts by mass of water, adjusted to pH 7.0 with a 2N aqueous sodium hydroxide solution, and cyclodextrin glucanotransferase derived from Bacillus stearothermophilus (manufactured by Hayashibara Co., Ltd.) was added at 15 units per 1 g of dextrin, and the reaction was carried out at 68 °C for 48 hours. After completion of the reaction, the enzyme was inactivated by heating and then filtered to obtain a reaction solution containing α-glycosylnarigenin. Next, this reaction solution was adjusted to pH 4.5, and glucoamylase (trade name: Gluc-team (manufactured by Amano Pharmaceutical Co., Ltd.)) was added at 100 units per 1 g of dextrin, and the reaction was carried out at 55 °C for 24 hours to produce α-glucosylnarigenin from α-glycosylnarigenin. Then, α-glucosidase (trade name: Transglucosidase L <Amano> (manufactured by Amano Pharmaceutical Co., Ltd.)) was added at 1 mL per 1 g of α-glycosylnarigenin, and the reaction was carried out at 55 °C for 24 hours to decompose 3″-α-,4´-α-diglucosylnarigenin and 4´-α-glucosylnarigenin, respectively, to produce 3″-α-glucosylnarigenin and naringin. After completion of the reaction, the enzyme was inactivated by heating and then the reaction solution was filtered, and the resulting filtrate was passed through a column packed with a porous synthetic adsorbent at SV2 to adsorb α-glucosylnarigenin and naringin in the solution to the column, and the column was washed with water to remove glucose, salts, etc. that did not adsorb to the column. Next, an aqueous ethanol solution with a gradually increasing ethanol concentration was passed through the column to elute 3″-α-glucosylnarigenin and naringin, and the eluate was concentrated under reduced pressure and powdered to obtain an α-glucosylnarigenin composition. As a result of HPLC analysis, its composition (naringenin ratio (molar ratio)) was 70% for glucosylnarigenin (3″-α-glucosylnarigenin) and 30% for naringin. The HPLC analysis was carried out under the following conditions.

[0043] <HPLC analysis conditions> Column: 'CAPCELL PAK C18 UG 120' (manufactured by Shiseido Co., Ltd.) Eluent: water / acetonitrile / acetic acid = 80 / 20 / 0.01 (v / v) Detection: UV280nm Temperature: 40℃ Flow rate: 0.8mL / min

[0044] <Experiment 1-2: Preparation of test emulsion composition and emulsion stability test> 14.4 g of the α-glucosyl naringin composition obtained in Experiment 1-1 above was placed in a polypropylene container, and 985.6 g of ultrapure water was added and dissolved to prepare a 1.44 mass% α-glycosyl naringin composition aqueous solution, which was stored in a water bath heated to 80°C until use. Next, 10.5 g of liquid paraffin (trade name "Moresco White P-70 (manufactured by MORESCO Corporation)) as an oil component and 175 mg of various surfactants were added to another polypropylene container, and dissolved and mixed in a water bath heated to 80°C to prepare oil-surfactant mixtures, which were then stored in a water bath heated to 80°C until use. Thereafter, while heating the oil-surfactant mixture in an 80°C water bath, the above 1.44 mass% α-glycosyl naringin composition was gradually added to the water bath while stirring at 4,000 rpm using a Polytron homogenizer (PT2500E, shaft diameter φ12 mm) (manufactured by KINEMATICA). 24.3 g of an aqueous solution of glucosyl naringin composition was added. Then, while heating in an 80°C water bath, the mixture was stirred at 4,000 rpm for an additional 3 minutes. The stirred mixture was removed from the water bath and cooled at room temperature while continuing to stir at 4,000 rpm. When the temperature of the stirred mixture dropped to below 40°C, stirring was stopped and the test emulsion composition was used. An emulsion composition prepared in the same manner using ultrapure water instead of the 1.44% by mass aqueous solution of glucosyl naringin was used as a control composition. The compositions of the test emulsion composition and the control composition are shown in Table 1. The 11 surfactants used are shown in Table 2.

[0045] After preparation, the test emulsion compositions were allowed to stand at room temperature for 30 minutes, then transferred to a 30°C environment and allowed to stand for an additional hour, after which the emulsion stability of the test emulsion compositions was evaluated by visual observation. Emulsion stability was evaluated based on the presence or absence of separation between the oil and aqueous layers of the composition after standing for 1 hour in a 30°C environment. Test emulsion compositions that showed the same degree of separation as the control emulsion composition were rated as "X", and those that showed little separation and a good emulsification state were rated as "O". The results are shown in Table 2.

[0046] [Table 1]

[0047] [Table 2]

[0048] Emulsion compositions were prepared using combinations of glycosyl naringenin and 11 types of surfactants, and stability tests were conducted. Surprisingly, it was found that only nonionic surfactants combined with glycosyl naringenin provided significantly superior emulsion stability compared to corresponding control compositions prepared in the same manner but without the aqueous solution of α-glucosyl naringin composition. On the other hand, with ionic surfactants, whether anionic, cationic, or amphoteric, the emulsion compositions separated and had low emulsion stability, comparable to the corresponding control compositions prepared in the same manner but without the aqueous solution of α-glucosyl naringin composition.

[0049] That is, it was revealed that the α-glucosyl naringin composition enhances the stability of the emulsion composition only when a nonionic surfactant is used. This result indicates that the stabilizer of the present invention is effective as a stabilizer for emulsion compositions emulsified using a nonionic surfactant.

[0050] <Experiment 1-3: Preparation of test emulsion composition and emulsion stability test 2> The emulsion stability of nonionic surfactants was further investigated. As shown in Table 3, test emulsion compositions were prepared using the same method as in Experiment 1-2, except that the nonionic surfactants glyceryl oleate (trade name "NIKKOL MGO" (manufactured by Nikko Chemicals Co., Ltd.)) or glyceryl isostearate (trade name "NIKKOL MGIS" (manufactured by Nikko Chemicals Co., Ltd.)) were used as the surfactant.

[0051] After preparation, the test emulsion compositions were allowed to stand at room temperature for 30 minutes, then transferred to a 30°C environment and allowed to stand for 3 days, after which the emulsion stability of the test emulsion compositions was evaluated by visual observation. Emulsion stability was evaluated based on the presence or absence of separation between the oil and aqueous layers of the composition after standing for 3 days in a 30°C environment. Test emulsion compositions that showed the same degree of separation as the control emulsion composition were rated as "X", and those that showed little separation and a good emulsification state were rated as "O". The results are shown in Table 3.

[0052] [Table 3]

[0053] As shown in Table 3, emulsion compositions were prepared and stability tests were conducted using combinations of the α-glucosyl naringin composition with glyceryl oleate (No. 12) or glyceryl isostearate (No. 13), both of which are nonionic surfactants classified as glycerin fatty acid esters. As in Experiment 1-2, it was found that the emulsion stability was extremely superior to that of the corresponding control composition prepared in the same manner except that it did not contain the α-glucosyl naringin composition aqueous solution.

[0054] These results indicate that when an ester-type nonionic surfactant is used, the α-glucosyl naringin composition enhances the stability of the emulsion composition not only with the sorbitan fatty acid ester (sorbitan monostearate (No. 10)) shown in the results of Experiment 1-2 (Table 2) but also with glycerin fatty acid ester.

[0055] <Experiment 2-1: Effect of the mass ratio of glycosylnaringenin to surfactant on the stability of emulsion compositions> Using the α-glucosylnaringin composition prepared in Experiment 1-1 as glycosylnaringenin and the nonionic surfactant sorbitan monostearate as the surfactant, emulsion compositions with various mass ratios of nonionic surfactant to glucosylnaringenin were prepared, and tests were conducted to evaluate their stability.

[0056] <Preparation of test emulsion composition and emulsion stability test> Test emulsion compositions 1 to 12 were prepared using the same method as in Experiment 1, except that the final concentration of the α-glucosyl naringin composition obtained in Experiment 1-1 in the emulsion composition was 0.001 to 40% by mass (i.e., the final concentrations of the α-glucosyl naringin composition in test emulsion compositions 1 to 12 described below were adjusted to 0.001, 0.005, 0.01, 0.1, 1, 3, 4, 5, 10, 20, and 40% by mass, respectively), that the nonionic surfactant sorbitan monostearate (trade name "Rheodor AS-10V" (manufactured by Kao Corporation)) was used as the surfactant, and that the final concentration of the nonionic surfactant in the emulsion composition was 0.5% by mass. Control 1 was prepared using ultrapure water instead of the aqueous solution of the α-glycosyl naringin composition, and Control 2 was prepared using ultrapure water instead of the surfactant, with the final concentration of the α-glucosyl naringin composition being 0.5% by mass.

[0057] After preparation, the test emulsion compositions were allowed to stand at room temperature for 30 minutes, then transferred to a 30°C environment and allowed to stand for 4.5 hours before evaluation. To evaluate stability, the volume of the water in the aqueous layer that separated over time was visually measured according to the scale on the polypropylene container as an indicator of the emulsified state of the test emulsion compositions. The volume of the separated aqueous layer of the test emulsion compositions was calculated as a relative separation rate, assuming that the volume of the separated aqueous layer of the Control 1 composition was 100%. A relative separation rate of less than 60% was evaluated as "◎", a rate of 60% to less than 80% was evaluated as "◯", a rate of 80% to less than 100% was evaluated as "△", and a rate of 100% was evaluated as "X". The results are shown in Table 4.

[0058] [Table 4]

[0059] Emulsion compositions were prepared using the nonionic surfactant sorbitan monostearate as the surfactant, with the final concentration of the α-glucosyl naringin composition in the emulsion composition varied from 0 to 40% by mass. As a result, as shown in Table 4, the stability of the emulsion composition was good (evaluated as "◯" or "◎") when the final concentration of the α-glucosyl naringin composition in the emulsion composition was 0.001 to 20% by mass, and the mass ratio of glycosyl naringenin (i.e., the α-glucosyl naringin composition) to surfactant in the emulsion composition at this time was 1:0.002 to 40. Furthermore, the stability of the emulsion composition was significantly good (evaluated as "◎") when the final concentration of the α-glucosyl naringin composition in the emulsion composition was 1:5 to 5% by mass, and the mass ratio of glycosyl naringenin (i.e., the α-glucosyl naringin composition) to surfactant in the emulsion composition at this time was 1:2 to 10.

[0060] These results indicate that when the α-glucosyl naringin composition, i.e., glycosyl naringenin, is used in a ratio of 0.002 to 40 parts by mass, preferably 2 to 10 parts by mass, per 1 part by mass of nonionic surfactant, a significant stabilizing effect on the emulsion composition emulsified with the nonionic surfactant is exerted.

[0061] <Experiment 2-2: Effect of the mass ratio of glycosylnaringenin to surfactant on the stability of emulsion composition 2> Using the α-glucosyl naringin composition prepared in Experiment 1-1 as glycosyl naringenin and the nonionic surfactants glyceryl oleate or glyceryl isostearate as the surfactant, emulsion compositions containing the α-glucosyl naringin composition and nonionic surfactant in various mass ratios were prepared, and tests were conducted to evaluate their stability.

[0062] <Experiment 2-2-1: Preparation of test emulsion composition and emulsion stability test> Test emulsion compositions 13 to 20 using glyceryl oleate as the nonionic surfactant and test emulsion compositions 21 to 28 using glyceryl isostearate as the nonionic surfactant were prepared using the same method as that shown in Experiment 2-1, except that the final concentration of the α-glucosyl naringin composition obtained in Experiment 1-1 in the emulsion composition was 0.001 to 40% by mass (i.e., the final concentrations of the α-glucosyl naringin composition in test emulsion compositions 13 to 20 and 21 to 28 described below were adjusted to 0.001, 0.01, 0.1, 0.5, 1, 5, 10, and 20% by mass, respectively), and that the nonionic surfactants glyceryl oleate (trade name "NIKKOL MGO") or glyceryl isostearate (trade name "NIKKOL MGIS") were used as the surfactant. The controls were Control 1, in which ultrapure water was used instead of the α-glycosyl naringin composition aqueous solution, and Control 2, in which ultrapure water was used instead of the surfactant and the final concentration of the α-glucosyl naringin composition was 0.5% by mass.

[0063] After preparation, the test emulsion composition was allowed to stand at room temperature for 30 minutes, then transferred to a 30°C environment and allowed to stand for 3 days. To evaluate stability, the volume of the oil layer that separated over time was visually measured according to the scale on the polypropylene container as an indicator of the emulsified state of the test emulsion composition. The volume of the separated oil layer of the test emulsion composition was calculated as a relative separation rate, assuming that the volume of the separated oil layer of the composition of Control 1 was 100%. A relative separation rate of less than 60% was evaluated as "◎", a rate of 60% to less than 80% was evaluated as "◯", a rate of 80% to less than 100% was evaluated as "△", and a rate of 100% was evaluated as "X". The results are shown in Tables 5 and 6.

[0064] [Table 5]

[0065] [Table 6]

[0066] As shown in Table 5, emulsion compositions were prepared using the nonionic surfactant glyceryl oleate as the surfactant, with the final concentration of the α-glucosyl naringin composition in the emulsion composition being 0 to 20% by mass. The stability of the emulsion composition was found to be good (evaluated as "◯" or "◎") when the final concentration of the α-glucosyl naringin composition, in other words, glycosyl naringenin, in the emulsion composition was 0.001 to 20% by mass, and the mass ratio of glycosyl naringenin to surfactant in the emulsion composition was 1:0.002 to 40. Furthermore, the stability was found to be significantly good (evaluated as "◎") when the final concentration of glycosyl naringenin was 0.1 to 20% by mass, and the mass ratio of glycosyl naringenin to surfactant in the emulsion composition was 1:0.2 to 40.

[0067] Furthermore, as shown in Table 6, when emulsion compositions were prepared using the nonionic surfactant glyceryl isostearate as the surfactant and with a final concentration of α-glucosyl naringin in the emulsion composition of 0 to 20% by mass, the stability of the emulsion composition was found to be good (evaluated as "◯" or "◎") when the final concentration of α-glucosyl naringin in the emulsion composition, in other words, glycosyl naringenin, was 0.001 to 20% by mass, and the mass ratio of glycosyl naringenin to surfactant in the emulsion composition was 1:0.002 to 40. Furthermore, the stability was found to be significantly good (evaluated as "◎") when the final concentration of glycosyl naringenin was 0.01 to 20% by mass, and the mass ratio of glycosyl naringenin to surfactant in the emulsion composition was 1:0.02 to 40.

[0068] In other words, these results show that when the α-glucosyl naringin composition is used in a ratio of 0.002 to 40 parts by mass per 1 part by mass of nonionic surfactant, a stabilizing effect is exerted on the emulsion composition emulsified with the nonionic surfactant, which is consistent with the results obtained previously in Experiment 2-1.

[0069] <Experiment 3: Effect of glycosylnaringenin composition ratio on the stability of emulsion compositions> Emulsion compositions were prepared using glycosylnaringenin, which was a mixture of 3'-α-glucosylnaringin and naringin at various mass ratios, and tests were conducted to evaluate their stability.

[0070] <Experiment 3-1: Preparation of Highly Purified 3"-α-Glucosylnaringin> The α-glucosyl naringin composition obtained in Experiment 1-1 was dissolved in a water / acetonitrile / acetic acid mixture (80 / 20 / 0.01 (v / v)). Using a method similar to the HPLC analysis conditions described above and a differential refractometer as a detector, the solution was passed through a C18 column to separate 3′-α-glucosyl naringin and naringin, and the 3′-α-glucosyl naringin fraction was collected. The fraction was then concentrated under reduced pressure and powdered to obtain a powdered 3′-α-glucosyl naringin purified preparation. HPLC analysis revealed that the purity of 3′-α-glucosyl naringin in the obtained purified preparation was 99.9% by mass.

[0071] <Experiment 3-2: Preparation of test emulsion composition and emulsion stability test> Test emulsion compositions 29 to 37 were prepared using the same method as in Experiment 2-1, except that glycosylnaringenin was prepared by mixing the purified 3′-α-glucosylnaringin preparation (purity 99.9% by mass) obtained in Experiment 3-1 with naringin (manufactured by ACROS Organics, purity 99.4% by mass) in the proportions shown in Table 7. Nine types of glycosylnaringenin mixtures with different mixing ratios were used, and the final concentration of the glycosylnaringenin mixture in the emulsion composition was fixed at 0.5% by mass. Control 1 was prepared by using ultrapure water instead of the glycosylnaringenin mixture.

[0072] After preparation, the test emulsion compositions were allowed to stand at room temperature for 30 minutes, then transferred to a 25°C environment and allowed to stand for 4.5 hours before evaluation. To evaluate emulsion stability, the volume of the aqueous layer that separated over time was measured visually according to the scale on the polypropylene container as an indicator of the emulsified state of the test emulsion compositions. The volume of the aqueous layer of the test composition was calculated as the relative separation rate when the volume of the separated aqueous layer of the control composition was taken as 100%. A relative separation rate of less than 60% was evaluated as "◎", a rate of 60% to less than 80% was evaluated as "◯", a rate of 80% to less than 100% was evaluated as "△", and a rate of 100% was evaluated as "X". The results are shown in Table 7.

[0073] [Table 7]

[0074] As shown in Table 7, test emulsion compositions were prepared using the nonionic surfactant sorbitan monostearate as the surfactant, and the mass ratio of 3"-α-glucosyl naringin to naringin was varied from 100:0 to 0:100. As a result, the stability of the emulsion compositions was improved, although to varying degrees, compared to Control 1 across the entire range of 3"-α-glucosyl naringin to naringin mass ratios from 100:0 to 0:100. In particular, when the mass ratio of 3"-α-glucosyl naringin to naringin was in the range of 100:0 to 9:91, the relative separation rate was evaluated as "Good" or "Excellent," demonstrating an excellent improvement in emulsion stability.

[0075] However, when the mass ratio of 3"-α-glucosyl naringin to naringin was 9:91 and 0:100, although the emulsion stability was improved as described above, precipitation of insoluble matter was observed after the evaluation, and as far as the test was concerned, the results were somewhat inferior in terms of quality as an emulsion composition product. On the other hand, when the mass ratio of 3"-α-glucosyl naringin to naringin was 15:85, no precipitation of insoluble matter was observed after the evaluation, and the emulsion stability was improved and the quality as an emulsion composition product was also satisfactory. If 3"-α-glucosylnaringin is taken as 1, then a mass ratio of 9:91 corresponds to 1:10.1, a mass ratio of 15:85 corresponds to 1:5.7, and a mass ratio of 100:0 corresponds to 1:0. Therefore, in order to improve emulsion stability while avoiding precipitation of insoluble matter, it was determined that the mass ratio of 3"-α-glucosylnaringin to naringin is preferably in the range of 1:0 to 1:10, more preferably in the range of 1:0 to 1:8, and even more preferably in the range of 1:0 to 1:6.

[0076] Furthermore, as shown in Table 7, when the mass ratio of 3'-α-glucosylnaringin to naringin was between 90:10 and 20:80, the relative separation rate was stably below 60% (determined as "◎"). This markedly improved stability of the emulsion composition compared to the case of 3'-α-glucosylnaringin alone (mass ratio 100:0) or naringin alone (mass ratio 0:100). These results suggest that the use of two or more types of glycosylnaringenin in combination is more effective than the use of one type alone. This indicates that the stabilizing effect of lingenin on the emulsion composition is synergistically enhanced, resulting in a significant improvement in emulsion stability. When 3"-α-glucosylnaringin is taken as 1, a mass ratio of 90:10 corresponds to a ratio of 1:0.1, and a mass ratio of 20:80 corresponds to a ratio of 1:4. Therefore, when 3"-α-glucosylnaringin and naringin are used in combination, it is preferable that the mass ratio of the two is in the range of 1:0.1 to 1:4, and it was concluded that significantly superior emulsion stability is exhibited.

[0077] <Experiment 3-3: Preparation of test emulsion composition and emulsion stability test 2> The mass ratios of glycosylnaringenin used in Experiment 3-2 to the purified 3'-α-glucosylnaringin preparation (purity 99.9% by mass) obtained in Experiment 3-1 and naringin (purity 99.4% by mass) were 100:0, 90:10, 75:25, 50:50, 33:67, 20:80, and 15:85 (the final concentration of the glycosylnaringenin mixture in the emulsion composition was fixed at 0.5% by mass). As the surfactant, sorbitan monostearate was replaced with the nonionic surfactant glyceryl oleate (trade name "NIKKOL MGO") or glyceryl isostearate (trade name "NIKKOL MGO"). Test emulsion compositions 38 to 44, which used glyceryl oleate as the nonionic surfactant, and test emulsion compositions 45 to 51, which used glyceryl isostearate as the nonionic surfactant, were prepared using the same method as in Experiment 3-2, except that glyceryl oleate (MGIS) was used as the nonionic surfactant. Control 1 was prepared by using ultrapure water instead of glycosylnaringenin.

[0078] After preparation, the test emulsion composition was allowed to stand at room temperature for 30 minutes, then transferred to a 30°C environment and allowed to stand for 7 days. To evaluate stability, the volume of the oil layer that separated over time was visually measured according to the scale on the polypropylene container as an indicator of the emulsified state of the test emulsion composition. The volume of the separated oil layer of the test emulsion composition was calculated as a relative separation rate, assuming the volume of the separated oil layer of the control composition as 100%. A relative separation rate of less than 60% was evaluated as "◎", a rate of 60% to less than 80% as "◯", a rate of 80% to less than 100% as "△", and a rate of 100% as "×". The results are shown in Tables 8 and 9.

[0079] [Table 8]

[0080] [Table 9]

[0081] As shown in Tables 8 and 9, test emulsion compositions were prepared and tested using glycosyl naringenin with a mass ratio of 3"-α-glucosyl naringin to naringin ranging from 100:0 to 15:85, and nonionic surfactants such as glyceryl oleate or glyceryl isostearate as the surfactant. The stability of the emulsion compositions was remarkably good (evaluated as "◎") across the entire range of mass ratios of 3"-α-glucosyl naringin to naringin tested (3"-α-glucosyl naringin to naringin mass ratios ranging from 100:0 to 15:85). Furthermore, no precipitation of insoluble matter was observed after testing. These results show that the stabilizer of the present invention exhibits the same tendency in emulsion compositions emulsified using a glycerin fatty acid ester-based surfactant as the nonionic surfactant as in emulsion compositions emulsified using a sorbitan fatty acid ester-based surfactant, and that significantly excellent emulsion stability is exhibited when the mass ratio of 3′-α-glucosyl naringin to naringin is at least in the range of 100:0 to 15:85, i.e., in the range of 1:0 to 1:6.

[0082] The present invention will be specifically described below based on examples, but the present invention is not limited to these examples. [Example]

[0083] <Stabilizer for emulsion composition> Glycosyl naringenin was prepared according to the method described in Example 1 of JP 2002-199896 A. Specifically, 50 parts by weight of naringin and 200 parts by weight of DE8 dextrin were dissolved in 500 parts by weight of water with heating, adjusted to pH 7.0 with 2N aqueous sodium hydroxide, and 15 units of Bacillus stearothermophilus cyclodextrin glucanotransferase (Hayashibara Co., Ltd.) per gram of dextrin were added. The mixture was then reacted at 68°C for 48 hours. After the reaction was completed, the enzyme was heat-inactivated and filtered to obtain an α-glycosyl naringin-containing solution. The reaction mixture was then filtered, and the filtrate was passed through a column packed with a porous synthetic adsorbent, trade name Diaion HP-10 (sold by Mitsubishi Chemical Industries, Ltd.), at SV2. After washing the column with water, 50% by volume of ethanol was passed through it. The eluate was concentrated to remove the solvent and then powdered to obtain an α-glycosylnaringin preparation. HPLC analysis revealed that its composition (naringenin ratio (molar ratio)) was 74% glucosylnaringin (13% 3′-α-glucosylnaringin, 61% total of 3′-α-,4′-α-diglucosylnaringin and 4′-α-glucosylnaringin) and 26% naringin. This product can be suitably used as a stabilizer for emulsion compositions. [Example]

[0084] <Stabilizer for emulsion composition> The α-glycosyl naringin preparation obtained in Example 1 of the present specification was dissolved in water at 1% by mass, adjusted to pH 4.5, and 100 units of glucoamylase (trade name: Glucozyme (Amano Pharmaceutical Co., Ltd.)) was added per gram of the preparation, followed by a 24-hour reaction at 55°C. After filtering the reaction solution, the filtrate was passed through a column packed with a porous synthetic adsorbent (trade name: Diaion HP-10 (Mitsubishi Chemical Industries, Ltd.)) at SV2. As a result, the α-glycosyl naringin and unreacted naringin in the solution were adsorbed to the porous synthetic adsorbent, while glucose, salts, etc., were eluted without being adsorbed. The column was then washed with water, and then passed through a solution containing aqueous ethanol at gradually increasing concentrations. The α-glycosyl naringin fraction was collected, concentrated under reduced pressure, and powdered to obtain the α-glycosyl naringin preparation. HPLC analysis revealed that the composition (naringenin ratio (molar ratio)) was 72% glucosylnaringin (62% 3"-α-glucosylnaringin, 7% 3"-α-,4'-α-diglucosylnaringin, and 3% 4'-α-glucosylnaringin), and 28% naringin. This product can be suitably used as a stabilizer for emulsion compositions. [Example]

[0085] <Emulsion> 0.5 parts by weight of polyoxyethylene behenyl ether, 1 part by weight of polyoxyethylene sorbitol tetraoleate, 1 part by weight of lipophilic glyceryl monostearate, 0.5 parts by weight of pyruvic acid, 0.5 parts by weight of behenyl alcohol, 1 part by weight of avocado oil, 1 part by weight of the α-glucosyl naringin composition obtained in Experiment 1-1, and an appropriate amount of vitamin E and preservatives were heated and dissolved according to a conventional method, to which 1 part by weight of sodium L-lactate, 5 parts by weight of 1,3-butylene glycol, 0.1 parts by weight of carboxyvinyl polymer, and 85.3 parts by weight of purified water were added, and the mixture was emulsified using a homogenizer. An appropriate amount of fragrance was further added and mixed with stirring to produce an emulsion. This product can be advantageously used as a sunscreen, skin beautifier, whitening agent, etc., and is an emulsion with excellent stability and usability as an emulsion composition. Furthermore, the glycosylnaringenins contained in this product, such as α-glucosylnaringin, absorb ultraviolet rays, increase blood flow to the skin, suppress the generation of active oxygen and lipid peroxides, and strengthen capillaries, thereby inhibiting and improving the occurrence of wrinkles, expression wrinkles, and sagging skin, and inhibiting and improving skin aging, so it can be used to maintain firm, non-dull skin. [Example]

[0086] <Lotion> Stearic acid 2 parts by weight, cetyl alcohol 1.5 parts by weight, petrolatum 4 parts by weight, squalane 5 parts by weight, glycerol tri-2-ethylhexanoate 2 parts by weight, non-ionic surfactants: polyoxyethylene behenyl ether 2 parts by weight, dipropylene glycol 5 parts by weight, polyethylene glycol 1500 A lotion was prepared by mixing 3 parts by weight of 3"-α-glucosylnaringin, 1 part by weight of triethanolamine, 1 part by weight of the purified 3"-α-glucosylnaringin preparation obtained in Experiment 3-1, 73.5 parts by weight of purified water, and appropriate amounts of preservatives and fragrance, and emulsifying in a conventional manner. This product can be advantageously used as a sunscreen, skin beautifier, skin whitening agent, etc., and is a lotion with excellent stability and usability as an emulsion composition. Furthermore, since glycosylnaringenin absorbs ultraviolet rays, increases blood flow to the skin, suppresses the generation of active oxygen and lipid peroxides, and strengthens capillaries, this product has the effects of inhibiting and improving the occurrence of wrinkles, expression wrinkles, and sagging of the skin, and inhibiting and improving skin aging, and therefore can be used to maintain firm, non-dull skin. [Example]

[0087] <Lotion> A lotion was prepared by mixing 1 part by weight of microcrystalline wax, 2 parts by weight of beeswax, 2 parts by weight of lanolin, 20 parts by weight of liquid paraffin, 10 parts by weight of squalane, 7 parts by weight of propylene glycol, 5 parts by weight of palm kernel fatty acid diethanolamide as a nonionic surfactant, 5 parts by weight of the stabilizer of the present invention obtained in Example 1, 68.5 parts by weight of purified water, and appropriate amounts of preservatives and fragrance, followed by emulsification according to a conventional method. This product can be advantageously used as a sunscreen, skin beautifier, skin whitening agent, etc., and is a lotion with excellent stability and usability as an emulsion composition. Furthermore, this product contains glycosylnaringenin, which absorbs ultraviolet rays, increases blood flow in the skin, suppresses the generation of reactive oxygen species and lipid peroxides, and strengthens capillaries, thereby inhibiting and improving the occurrence of wrinkles, expression wrinkles, and sagging, and inhibiting and improving skin aging. Therefore, it can be used to maintain firm, non-dull skin. [Example]

[0088] <Cream> A cream was prepared by mixing 8 parts by weight of stearic acid, 4 parts by weight of stearyl alcohol, 6 parts by weight of butyl stearate, 5 parts by weight of propylene glycol, 2 parts by weight of glycerol monostearate as a nonionic surfactant, 0.4 parts by weight of potassium hydroxide, 5 parts by weight of the stabilizer of the present invention obtained in Example 2, 69.6 parts by weight of purified water, and appropriate amounts of preservatives and fragrances, followed by emulsification according to a conventional method. This product can be advantageously used as a sunscreen, skin beautifier, skin whitening agent, etc., and is a cream with excellent stability and usability as an emulsion composition. Furthermore, this product contains glycosylnaringenin, which absorbs ultraviolet rays, increases blood flow in the skin, suppresses the generation of reactive oxygen species and lipid peroxides, and strengthens capillaries, thereby inhibiting and improving the occurrence of wrinkles, expression wrinkles, and sagging, and inhibiting and improving skin aging. Therefore, it can be used to maintain firm, non-dull skin. [Example]

[0089] <Cream> A cream was produced by mixing 6 parts by weight of stearyl alcohol, 2 parts by weight of stearic acid, 4 parts by weight of hydrogenated lanolin, 9 parts by weight of squalane, 10 parts by weight of octyldodecanol, 6 parts by weight of 1,3-butylene glycol, 4 parts by weight of polyethylene glycol 1500, 5 parts by weight of polyoxyethylene behenyl ether as a nonionic surfactant, 5 parts by weight of the α-glucosyl naringin composition obtained in Experiment 1-1, 49 parts by weight of purified water, and appropriate amounts of preservatives and fragrance, and emulsifying the mixture according to a conventional method. This product can be advantageously used as a sunscreen, skin beautifier, skin whitening agent, etc., and is a cream with excellent stability and usability as an emulsion composition. Furthermore, glycosylnaringenin in this product absorbs ultraviolet rays, increases blood flow in the skin, suppresses the generation of active oxygen and lipid peroxides, and strengthens capillaries, thereby inhibiting and improving the occurrence of wrinkles, expression wrinkles, and sagging skin, as well as inhibiting and improving skin aging, so it can be used to maintain firm, non-dull skin. [Example]

[0090] <Cream> 5 parts by mass of cetyl alcohol, 3 parts by mass of stearic acid, 5 parts by mass of petrolatum, 10 parts by mass of squalane, 7 parts by mass of glycerol tri-2-ethylhexanoate, 5 parts by mass of dipropylene glycol, 5 parts by mass of glycerin, 2 parts by mass of propylene glycol monostearate, 2 parts by mass of POE(20) cetyl alcohol ether and 2 parts by mass of palm kernel fatty acid diethanolamide as nonionic surfactants, 1 part by mass of triethanolamine, 5 parts by mass of the purified 3'-α-glucosylnaringin sample obtained in Experiment 3-1, 49 parts by mass of purified water, and appropriate amounts of preservatives and fragrances. The ingredients were mixed and emulsified according to conventional methods to produce a cream. This product can be advantageously used as a sunscreen, skin beautifier, skin whitening agent, etc., and is a cream with excellent stability and usability as an emulsion composition. Furthermore, glycosylnaringenin absorbs ultraviolet rays, increases blood flow in the skin, suppresses the generation of active oxygen and lipid peroxides, and strengthens capillaries, thereby inhibiting and improving the occurrence of wrinkles, expression wrinkles, and sagging skin, and inhibiting and improving skin aging, so it can be used to maintain firm, non-dull skin. [Example]

[0091] <Cream> 2 parts by weight of polyoxyethylene glycol monostearate, 5 parts by weight of self-emulsifying glycerin monostearate, 1 part by weight of liquid paraffin, 10 parts by weight of glyceryl trioctanoate, and an appropriate amount of preservative were heated and dissolved in a conventional manner, to which 2 parts by weight of the stabilizer of the present invention obtained in Example 1, 2 parts by weight of L-lactic acid, 5 parts by weight of 1,3-butylene glycol, and 66 parts by weight of purified water were added, and the mixture was emulsified in a homogenizer. An appropriate amount of fragrance was then added and mixed by stirring to produce a cream. This product can be advantageously used as a sunscreen, skin beautifier, skin whitening agent, etc., and is a cream with excellent stability and feel as an emulsion composition. Furthermore, glycosylnaringenin in this product absorbs ultraviolet rays, increases blood flow in the skin, suppresses the generation of active oxygen and lipid peroxides, and strengthens capillaries, thereby inhibiting and improving the occurrence of wrinkles, expression wrinkles, and sagging skin, as well as inhibiting and improving skin aging, so it can be used to maintain firm, non-dull skin. [Example]

[0092] <Lipstick> A lipstick was prepared by heating and dissolving 3.5 parts by weight of titanium dioxide, 0.5 parts by weight of Red No. 201, 2 parts by weight of Red No. 202, 0.05 parts by weight of Red No. 223, 8 parts by weight of candelilla wax, 30 parts by weight of castor oil, 20 parts by weight of cetyl 2-ethylhexanoate, 4 parts by weight of ceresin, 2 parts by weight of carnauba wax, 11 parts by weight of lanolin, 40 parts by weight of diglyceride isostearate, 1 part by weight of polyoxyethylene (25) polyoxypropylene (20) 2-tetradecyl ether, 1 part by weight of glycerin, 2 parts by weight of glycosyl trehalose (trade name "Tornare" (Hayashibara Co., Ltd.)), 1 part by weight of the stabilizer of the present invention obtained in Example 2, and 4 parts by weight of purified water according to a conventional method. This product was a lipstick with excellent stability and feel as an emulsion composition. Furthermore, this product contains glucosyl naringin, which absorbs ultraviolet rays, increases blood flow to the lips and surrounding areas, inhibits the generation of reactive oxygen species and lipid peroxides, and strengthens capillaries, resulting in good color development, inhibiting and improving the appearance of wrinkles and expression lines on the lips and surrounding areas, and long-lasting effects of inhibiting and improving lip aging, making it suitable for maintaining firm, flawless lips. Furthermore, because this product contains glycosyl trehalose, it provides a glossy, non-sticky finish when applied to the lips, ensuring excellent makeup retention and a comfortable feel. Furthermore, the antioxidant and anti-inflammatory properties of glycosyl trehalose and glycosyl naringenin prevent roughness or inflammation when applied to the lips, making it extremely safe, with no odor or deformation observed even when left at high temperatures for extended periods. [Industrial Applicability]

[0093] The stabilizer for emulsion compositions of the present invention is effective for emulsion compositions emulsified using a nonionic surfactant, and can significantly improve the emulsion stability. Furthermore, emulsion compositions containing the stabilizer of the present invention have an extremely excellent feel when used, and can be advantageously used in various fields such as food, cosmetics, quasi-drugs, pharmaceuticals, and industrial products. Furthermore, when the stabilizer of the present invention is used, the surfactant content can be reduced, thereby improving formulation flexibility and reducing the risk of skin irritation and other problems, thereby increasing safety, which is of great industrial significance.

Claims

1. A stabilizer for an emulsion composition emulsified using a nonionic surfactant, which contains glycosylnaringenin as an active ingredient.

2. 2. The stabilizer according to claim 1, wherein the glycosylnaringenin is one or more members selected from the group consisting of naringin, 3'-α-glucosylnaringin, 3'-α-,4'-α-diglucosylnaringin, 4'-α-glucosylnaringin, prunin, and narirutin.

3. 3. The stabilizer according to claim 1, wherein the mass ratio of 3'-α-glucosylnaringin to naringin in the glycosylnaringenin is in the range of 1:0 to 1:

10.

4. 4. The stabilizer according to claim 1, wherein the nonionic surfactant is an ester surfactant, an ether surfactant, an amide surfactant, an ester ether surfactant, or an alkyl polyglucoside surfactant.

5. 5. The stabilizer according to claim 4, wherein the ester surfactant is a glycerin fatty acid ester surfactant, a sorbitan fatty acid ester surfactant, or a sucrose fatty acid ester surfactant.

6. A stabilizer as described in claim 4, wherein the ester ether type surfactant is a polyoxyethylene type surfactant.

7. A stabilizer as described in claim 6, wherein the polyoxyethylene type surfactant is a fatty acid polyethylene glycol type surfactant or a fatty acid polyoxyethylene sorbitan type surfactant.

8. A stabilizer as described in claim 4, wherein the ether type surfactant is a polyoxyethylene type surfactant.

9. 9. The stabilizer according to claim 8, wherein the polyoxyethylene surfactant is a polyoxyethylene alkyl ether surfactant, a polyoxyethylene alkyl phenyl ether surfactant, or a polyoxyethylene polyoxypropylene glycol surfactant.

10. A stabilizer described in any one of claims 1 to 9, which is used so that the glycosyl naringenin is contained in a ratio of 0.002 to 40 parts by mass per 1 part by mass of the nonionic surfactant used in the emulsion composition.

11. A method for stabilizing an emulsion composition emulsified using a nonionic surfactant, the method comprising the step of incorporating the stabilizer according to any one of claims 1 to 10 into a raw material, intermediate product, and / or manufactured emulsion composition of the emulsion composition.

12. The stabilization method according to claim 11, wherein the stabilizer is contained in an amount of glycosylnaringenin of 0.002 to 40 parts by mass per part by mass of the nonionic surfactant contained in the emulsion composition.

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