JP2007111010A - Phytosterol-containing composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a phytosterol-containing composition in which a phytosterol is readily and uniformly dispersed in water and which neither crystallizes nor precipitates even in long-term preservation and has high stability. <P>SOLUTION: The composition comprises a phytosterol and a polyglycerol fatty acid ester obtained by esterifying a polyglycerol having ≤1,200 hydroxy value and ≥50% primary hydroxy group of the whole hydroxy group with a fatty acid as an essential components. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a plant sterol-containing composition having a high stability that is easily uniformly dispersed in water and that does not produce crystals or precipitates even when stored for a long period of time.

  Plant sterol is a general term for sterols contained in plants, and is contained in cell membranes of various plants regardless of grains, vegetables and fruits. Plant sterols have long been known to have a plasma cholesterol lowering action, and many reports have been made on their clinical effects. In recent years, the function and clinical effect of prostatic hypertrophy treatment has been scientifically proven, and it is a material that has received much attention as a functional food material. However, since plant sterol has a very high melting point (130 to 170 ° C.), is insoluble in water, and is only slightly soluble in oil, it is a substance that has extremely low versatility for use in food applications. Therefore, conventional plant sterol-containing foods are limited to edible fats and oils such as edible fats, dressings, and margarines that are used by suspending them in oil. There were drawbacks.

  Therefore, as a method for solving these problems, a technique for improving dispersibility in foods has been proposed. For example, a method for producing a plant sterol and a non-sterol emulsifier in an oil-in-water suspension (see, for example, Patent Document 1) has been proposed. However, the dispersion stability in the food ingredient is obtained only with oil and fat foods such as dressing and mayonnaise, and in fact, the stable dispersion in water-based beverages is insufficient. In addition, a plant sterol-containing water-soluble composition having a plant sterol, an emulsifier, an edible oil and fat, water, and having an HLB value of the emulsifier in the entire system of 12 or more, and a production method thereof (for example, see Patent Document 2), There has been proposed a method (for example, see Patent Document 3) and the like in which a mixture substantially consisting only of a sterol and an emulsifier is heated and dissolved, and mixed at high speed with an aqueous beverage to obtain a plant sterol dispersion. In the former, the sterol content in the composition is as low as several percent, and it is extremely difficult to take the recommended daily amount of 400 to 800 mg when desiring to lower plasma cholesterol, because the taste of food and drink is impaired. In addition, since it is essential to dissolve plant sterols in fats and oils, it is not fully satisfactory considering the need to refrain from taking excess fats and oils for those who aim to treat or prevent cholesterol-related diseases. . In addition, the latter method requires a special high-pressure homogenizer treatment in order to obtain stable water and a dispersion in a beverage, and is substantially stable in homogenizers, homomixers and the like that are generally used for beverage preparation. Since it cannot be made, industrial versatility is low. Furthermore, even if these methods are used, only the temporary solubility in the aqueous system is improved, and as a composition containing a plant sterol amount that can maintain a stable emulsification and solubilization state for a long period of time and a physiological effect can be expected. There was nothing that was fully satisfactory.

JP-A-11-146757 (page 2-13) JP 2002-291442 A (page 2-10) Japanese Patent No. 3535147 (page 2-17)

  The present invention has been made in view of the prior art, and contains a plant sterol having a high stability in which a plant sterol is easily and uniformly dispersed in water and does not produce crystals or precipitates even when stored for a long period of time. It is an object to provide a composition.

  As a result of intensive studies to solve the above-mentioned problems, the present inventors have used a special polyglycerin fatty acid ester having an excellent phytosterol crystal suppression effect, emulsification, and solubilization effect, thereby providing food, beverage, or cosmetics. A plant sterol containing an amount of plant sterol that has excellent acid resistance, salt resistance, and heat resistance required when added to sucrose, maintains a stable emulsification or solubilization state even during long-term storage, and can be expected to have a physiological effect. It has been found that a containing composition is obtained.

  The present invention has been completed on the basis of these findings, the gist of which is a polyglycerol having a plant sterol and a hydroxyl value of 1200 or less and a primary hydroxyl group of 50% or more of all hydroxyl groups. The present invention provides a plant sterol-containing composition comprising, as an essential component, a polyglycerol fatty acid ester obtained by esterifying a fatty acid.

  The present invention also provides a plant sterol-containing composition containing a polyhydric alcohol in the above composition, and a plant sterol composition in which the composition is an oil-in-polyol (O / D type) emulsion. It is to provide.

  Furthermore, this invention provides the food / beverage products or cosmetics containing the said composition. The present invention is described in detail below.

  Sterol is a general term for steroid alcohols widely distributed in animals and plants. The steroid is a compound having a steroid nucleus, that is, a perhydro-1,2-cyclopentanophenanthrene skeleton.

  Plant sterol is a mixture of sitosterol, which is present in the cell membrane of every plant, including double bond, stigmasterol, campesterol, brassicasterol, fucostosterol and stanol without double bond. The generic name is phytosterol. The plant sterol used in the present invention is not particularly limited. For example, grains such as soybeans, rice, wheat, sesame, fruits and vegetables such as radish, cabbage, apple, lettuce, and other sunflowers, rapeseed, palm, straw Extracts from fruit and bark of trees, refined products, etc. are mentioned. In addition, the type of plant raw material to be extracted is not particularly limited, but among them, plant sterols obtained by separation from scum and the like produced by the deodorizing process of vegetable oils, and sterols obtained as by-products in the production of pulp However, it is also suitable from the industrial supply aspect.

  Plant sterols are contained in plant cell membranes in a free form or in a form bound to fatty acids or sugars. The plant sterols used in the present invention do not have to be separated separately, and may be purified products, mixed products, or ester types, but may be used in a free form for the purpose of increasing the plant sterol content in the composition of the present invention. Is preferred.

  The polyglycerol fatty acid ester used in the plant sterol-containing composition of the present invention is esterified with a polyglycerol having a hydroxyl value of 1200 or less and a primary hydroxyl group of 50% or more of all hydroxyl groups and a fatty acid. It has one big feature.

  Due to the above characteristics, the polyglycerol fatty acid ester used in the plant sterol-containing composition of the present invention is excellent in imparting water dispersibility of the plant sterol and is used as a surfactant that suppresses crystallization. It is something that can be done. That is, conventional polyglycerin fatty acid esters and food surfactants have insufficient performance and cannot be replaced.

  The polyglycerol in the polyglycerol fatty acid ester refers to a substance having a hydroxyl group and an ether bond in the molecule with a glycerol skeleton obtained by dehydration condensation of glycerol as a basic unit.

  The polyglycerol in the polyglycerol fatty acid ester is a polyglycerol having a primary hydroxyl group of 50% or more of all the hydroxyl groups in the molecule, and the viewpoint of further improving the solubilization performance and emulsion stability of the resulting polyglycerol fatty acid ester. Therefore, the primary hydroxyl group is preferably 55% or more of polyglycerol, more preferably 60% or more of polyglycerol. Further, the upper limit value is not particularly defined, but is desirably 90% or less in order to maximize the effect. The proportion of primary hydroxyl groups in the total hydroxyl groups in the polyglycerol of the present application changes depending on the degree of condensation of the polyglycerols, and the types of polyglycerols that are generally distributed are tetra, penta, hexa, and deca. In consideration of this, the upper limit value is exemplified by tetraglycerin 70% or less, preferably 65% or less, pentaglycerin 75% or less, preferably 70% or less, hexaglycerin 80% or less, preferably 75 % Or less, 85% or less, preferably 80% or less for decaglycerin. Furthermore, the hydroxyl value of polyglycerol is 1200 or less, and 1100 or less is more preferable, and 1000 or less is more preferable from the viewpoint that the hydrophilicity (HLB) of the polyglycerol fatty acid ester can be adjusted according to the use. Further, from the viewpoint of workability and ease of esterification with a fatty acid, the hydroxyl value is preferably 770 or more.

  The proportion of primary hydroxyl groups among all hydroxyl groups is measured using a method of measuring a nuclear magnetic resonance spectrum (NMR) for carbon atoms. The hydroxyl value can be measured by a method known in the art.

In addition, the nuclear magnetic resonance spectrum (NMR) with respect to a carbon atom can be measured as follows. Polyglycerin 500 mg is dissolved in 2.8 ml of heavy water, and after filtration, ¹³ C-NMR (125 MHz) spectrum is obtained by gated decoupling. The peak intensity is proportional to the carbon number by the gate decoupled measurement method. The ¹³ C chemical shifts indicating the presence of primary hydroxyl groups and secondary hydroxyl groups are about 63 ppm for methylene carbon (CH ₂ OH) and about 71 ppm for methine carbon (CHOH), respectively. The abundance ratio of the primary hydroxyl group and the secondary hydroxyl group is calculated. However, the methine carbon (CHOH) indicating the secondary hydroxyl group overlaps with the methylene carbon peak further adjacent to the methine carbon bonded to the methylene carbon indicating the primary hydroxyl group, and the integral value of itself cannot be obtained. The integrated value is calculated from the signal intensity around 74 ppm of methylene carbon (CH ₂ ) adjacent to (CHOH).

  The method for preparing polyglycerol fatty acid ester of polyglycerol fatty acid ester used in the plant sterol-containing composition is not limited, but can be obtained, for example, by devising a synthetic method or by fractional purification from commercially available polyglycerol.

  For example, a synthesized polyglycerin or a commercially available polyglycerin is reacted with a reagent that selectively binds to a primary hydroxyl group, that is, a reagent that serves as a protective group for the primary hydroxyl group. Then, since the number of protective groups increases as the number of primary hydroxyl groups in one molecule of polyglycerol increases, the polarity of the polyglycerol decreases as a result. On the other hand, since a protective group is difficult to be introduced into polyglycerin containing a lot of secondary hydroxyl groups, the polyglycerin maintains its original high polarity. It is possible to separate the two using this difference in polarity. The polyglycerin after the separation can be subjected to a protecting group elimination treatment to obtain polyglycerin containing a large amount of primary hydroxyl groups.

  In this case, examples of the reagent that selectively reacts with the primary hydroxyl group include chlorotriphenylmethyl, isobutene, 1-tritylpyridinium tetrafluoroborate, and the like. As for polyglycerin having no secondary hydroxyl group other than 1,2-diol, a compound that forms acetonide with polyglycerin (for example, methyl isopropenyl ether, 2,2-dimethoxypropane, 2,2-diethoxypropane, Acetone, etc.) can also be used. Of these, chlorotriphenylmethane is preferred because of the ease of introduction and elimination of primary hydroxyl groups.

  The reaction ratio of polyglycerin and the reagent is appropriately adjusted according to the desired number of primary hydroxyl groups in polyglycerin, but it is preferable to use an excessive amount of the reagent in order to surely proceed the reaction. For example, the reagent is preferably used in an amount of 2 to 10 mol, more preferably 3 to 7 mol, per 1 mol of polyglycerol.

  The reaction between polyglycerin and the reagent is preferably performed at 5 to 30 ° C, more preferably 10 to 25 ° C, from the viewpoint of the progress of the reaction and the certainty of protection.

  After the reaction, post-treatment may be performed in the same manner as a normal chemical reaction. Organic solvents such as pyridine can be removed by distillation under reduced pressure.

  A method for fractionating the desired polyglycerol from the obtained reaction product can be achieved by utilizing the chemical and physical differences of the polyglycerol into which a protecting group has been introduced. For example, the target polyglycerol can be fractionated by a method such as distillation, vacuum distillation, molecular distillation using the difference in boiling points, or the target polyglycerol can be separated using the difference in solubility in water or an organic solvent. It can also be fractionated. For example, the target polyglycerin is fractionated by dispersing the reaction product in water and extracting it with an organic solvent immiscible with water (for example, chloroform, dichloromethane, petroleum ether, hexane, benzene, toluene, ether, ethyl acetate, etc.). can do. When this fractionation method is used, a solution of an inorganic salt such as water-containing ethanol, saline, or sodium sulfate solution can be used instead of water. It is preferable to fractionate the desired polyglycerol using water and ethyl acetate.

By removing the solvent after solvent extraction, a low-polarity polyglycerin derivative, that is, polyglycerin in which many protective groups are introduced in one molecule is obtained. Removal of the protecting group from this derivative can be carried out by a method used in general organic synthesis. For example, removal of the protecting group can be achieved by a method of allowing p-toluenesulfonic acid to act in methanol, a method of heating and stirring in an acetic acid aqueous solution, or the like. As an example, when a triphenylmethyl group is introduced into polyglycerin, a protective group is obtained by adding 2 to 3 times the amount of acetic acid aqueous solution to the obtained reaction product and stirring at 55 to 60 ° C. for 10 hours. Can be released.
Furthermore, the polyglycerin is prepared by condensing a glycerin derivative such as glycidol or epichlorohydrin to prepare a polyglycerin containing a large amount of primary hydroxyl groups, and mixing it with a commercially available polyglycerin to meet the purpose of the present invention. You may adjust the ratio of a secondary hydroxyl group and a secondary hydroxyl group.

  It is possible to prepare a polyglycerol having a hydroxyl value of 1200 or less by adjusting the polyglycerol reaction step as follows, for example. For example, when preparing using the glycerin polymerization method, the hydroxyl value decreases with the lapse of the polymerization reaction time. Therefore, by confirming the process of decreasing the hydroxyl value of the polyglycerol during the reaction, the polyglycerol having a hydroxyl value of 1200 or less can be obtained. Can be easily obtained.

  Fatty acids used in the present invention are particularly limited as long as they contain a carboxylic acid as a functional group obtained by hydrolyzing and extracting oils and fats extracted from natural animals and plants and purifying them with or without separation. is not. Alternatively, it may be a fatty acid obtained by chemically synthesizing petroleum or the like as a raw material. Alternatively, these fatty acids may be reduced by hydrogenation or the like, condensed fatty acids obtained by condensation polymerization of fatty acids containing hydroxyl groups, or polymerized fatty acids obtained by heat polymerization of fatty acids having unsaturated bonds. Good. The selection of these fatty acids may be appropriately determined in consideration of the desired effect. Specific examples of fatty acids used in the present invention include saturated or unsaturated fatty acids having 6 to 22 carbon atoms, that is, caproic acid, caprylic acid, octylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmito. Examples include oleic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, linolenic acid, behenic acid, erucic acid, ricinoleic acid having a hydroxyl group in the molecule, 12-hydroxystearic acid, and condensates thereof. Of these, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, and condensed ricinoleic acid are preferred in consideration of stabilization of plant sterols. More preferably, myristic acid, palmitic acid, stearic acid, and oleic acid are desirable.

  Esterification of polyglycerol and fatty acid is performed according to a method known in the art. For example, the esterification can be performed under normal pressure or reduced pressure in the presence of an alkali catalyst, an acid catalyst, or no catalyst. Moreover, the polyglycerol fatty acid ester which has various properties can be prepared by changing the mixing amount of polyglycerol and a fatty acid. For example, when obtaining a polyglycerin fatty acid ester for use in a hydrophilic surfactant, the polyglycerin and the fatty acid are charged by calculating the weight so as to be equimolar by calculation from the hydroxyl value of the polyglycerin and the molecular weight of the fatty acid. What is necessary is just to increase the number-of-moles of a fatty acid, when obtaining the polyglyceryl fatty acid ester for using for lipophilic surfactant. The resulting polyglycerol fatty acid ester may be further purified according to the usage requirements of the product used. The purification method may be any known method and is not particularly limited. For example, adsorption treatment with activated carbon or activated clay, deodorization treatment under reduced pressure using water vapor or nitrogen as a carrier gas, washing with acid or alkali, or molecular distillation. And may be purified.

  The polyglycerol fatty acid ester used in the plant sterol-containing composition of the present invention may be used alone or in combination with another surfactant from the viewpoint of improving the emulsion stability. For example, as the surfactant to be mixed, glycerin fatty acid ester, organic acid monoglyceride, monoglyceride derivative, propylene glycol fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene derivative, polyglycerin fatty acid ester (however, in the present invention) Nonionic surfactants (excluding polyglycerin fatty acid esters), amphoteric surfactants, anionic surfactants, cationic surfactants, lecithins, enzymatically decomposed lecithins, surfactants derived from natural products such as saponin, quilla extract, etc. Is mentioned. These may be used alone or in combination of two or more. Among them, it is preferable to use one or more of glycerin fatty acid ester, sucrose fatty acid ester and organic acid monoglyceride in combination. Furthermore, in consideration of stabilization when using plant sterols in beverages, the constituent fatty acids of the glycerin fatty acid ester are preferably stearic acid, isostearic acid, palmitic acid, oleic acid, and myristic acid, and the organic acid portion of the organic acid monoglyceride is the citric acid. Acid, succinic acid, and diacetyltartaric acid are desirable.

  In the plant sterol-containing composition of the present invention, of course, the composition is uniformly and stably dispersed in the food and drink for a long period of time, but by using a polyhydric alcohol, handling property, formulation stability, water Improves stability during dispersion. Although it does not specifically limit as a polyhydric alcohol in this case, it is a general term for the compound which has two or more hydroxyl groups in 1 molecule, Propylene glycol, glycerin, diglycerin, triglycerin, polyglycerin, sorbitol, xylitol, Maltitol, lactitol, sorbitan, xylose, arabinose, mannose, lactose, sugar, coupling sugar, glucose, enzyme starch syrup, acidified starch syrup, maltose starch syrup, maltose, isomerized sugar, fructose, reduced maltose starch syrup, reduced starch sugar starch syrup, Examples thereof include honey, fructose-glucose liquid sugar, and solutions thereof, and these may be used alone or in combination of two or more. Among these, propylene glycol, glycerin, diglycerin, triglycerin, and polyglycerin can be preferably used from the viewpoint of ease of preparation and stability, and further, from the viewpoint that propylene glycol and glycerin can be used in foods.

  Furthermore, by making the plant sterol-containing composition of the present invention a polyhydric alcohol-in-oil (O / D) emulsion, it can be easily dispersed in water and does not produce crystals or precipitates over time. It can be a thing. Therefore, plant sterol can be stably blended at a high concentration without deteriorating the commercial value of water-based foods such as beverages and cosmetics such as emulsions.

  The oil-in-polyhydric alcohol type (O / D type) emulsification in the present invention is obtained by dispersing an oil component in a polyhydric alcohol solution of a surfactant, and does not require a great mechanical force and is finely emulsified. Is possible. In the present invention, O / D type emulsification is effective for suppressing crystallization as well as fine emulsification of sterol, and it has been found that the stability is remarkably improved. Therefore, O / D type emulsification is recommended for the preparation of the present composition. .

  As a method for preparing the plant sterol-containing composition of the present invention, the above O / D type emulsification in which the polyglycerol fatty acid ester of the present invention is dissolved in a polyhydric alcohol to emulsify the plant sterol is recommended. The mixing method with a plant sterol is not particularly limited, and it can be obtained by emulsification using a stirring and emulsifying apparatus. For example, propeller type, anchor type, paddle type agitator, rotor / stator type emulsifier that can give stronger shearing force, mill type emulsifier with grinding function, high pressure nozzle type emulsifier that generates cavitation at high pressure , High-pressure collision emulsifiers that collide liquids under high pressure, and emulsify by impact force, shear force due to turbulent flow and cavitation, ultrasonic emulsifiers that generate cavitation with ultrasonic waves, membrane emulsification that uniformly emulsifies through pores Examples thereof include a static mixer that repeats a dispersed assembly of liquids in a machine and an element and uniformly mixes them. These can be used alone or in combination of two or more.

  Although it does not specifically limit as the compounding method of the plant sterol of this invention, Melting | fusing point of a plant sterol and a crystalline state change by melt | dissolving a plant sterol with monoglycerin fatty acid ester beforehand at high temperature, It is a paste-like also at normal temperature. Since the fluidity can be imparted, the stability of the preparation is improved. Moreover, when used for food and drink or cosmetics, dispersibility and storage stability are improved, which is preferable. The constituent fatty acid of the monoglycerin fatty acid ester is not limited, but preferably myristic acid, palmitic acid, stearic acid, oleic acid or a mixture thereof is desirable.

  The mixing ratio of the plant sterol and the monoglycerin fatty acid ester is not particularly limited, but is preferably in the range of plant sterol 99: 1 to 1:99, more preferably 90:10 to 20:80.

  The mixing temperature of the plant sterol and the monoglycerin fatty acid ester is not particularly limited, but is preferably 80 to 180 ° C., more preferably 110 to 150 ° C., and still more preferably 120 to 140 from the viewpoint of uniformly mixing both substances. It is desirable to be carried out at ° C.

  The composition of the plant sterol-containing composition of the present invention is not particularly limited, and may be arbitrarily prepared according to the purity of the plant sterol used, the food or drink to be added, or the design of the cosmetic. The lower limit is preferably 0.1% or more, more preferably 1% or more, and most preferably 15%, from the viewpoint of physiological effects and the influence on the flavor when applied to food and drink. That's it. The upper limit is preferably 80% or less, more preferably 60% or less, from the viewpoint of emulsion stability. The polyglycerol fatty acid ester is preferably 0.01% to 60%, more preferably 1% to 40%. The polyhydric alcohol is preferably 1% to 99%, more preferably 10% to 80%.

  In order to improve the product value of the plant sterol-containing composition of the present invention, other additive materials may be added. For example, functional oils and fats such as vitamins and polyunsaturated fatty acids, antioxidants, minerals, and the like in addition to fragrances and pigments.

  The plant sterol-containing composition of the present invention can be used as a supplement to a living body of plant sterols by ingestion as it is orally. For example, there are solutions, tablets, powder formulations, capsules and the like intended for plant sterol intake. Therefore, the food / beverage products which comprise the composition of this invention are provided as 1 aspect of this invention.

  The food and drink comprising the composition of the present invention is particularly intended for humans, but does not exclude feed or pet food such as livestock and household pets. In the following, food and drink for humans will be described, but the food and drink of the present invention includes the above feed.

  It does not specifically limit as food / beverage products, What is necessary is just a food / beverage product containing the plant sterol containing composition of this invention. Examples of such foods and beverages include instant noodles, cup noodles, retort / cooked food, cooked canned food, microwave food, instant soup / stew, instant miso soup / soup, canned soup, freeze-dried food, carbonated drink, natural Fruit juice, juice drink, soft drink with fruit juice, fruit drink, fruit food with fruit grains, vegetable drink, soy milk / soy milk drink, coffee drink, tea drink, powdered drink, concentrated drink, sports drink, nutrition drink, alcoholic drink, etc. Beverages, bread, macaroni and spaghetti, noodles, cake mix, flour foods such as fried bread and bread crumbs, gyoza and spring rolls, caramel candy, chewing gum, chocolate, cookie biscuits, cake pie, snack crackers , Japanese confectionery, rice confectionery, bean confectionery, dessert confectionery, etc. , Soy sauce, miso, sauces, processed tomato seasonings, mirins, vinegars, sweeteners, fish sauce, Nyokumam basic seasonings, flavor seasonings, cooking mix, curry sauce, sauces, dressing, noodle soup, Compound seasonings such as spices, fats and oils such as butter, margarine and mayonnaise, milk and processed milk, milk beverages, yogurts, lactic acid bacteria beverages, cheese, ice cream, prepared milk powder, dairy products such as cream, frozen foods, semi-cooked foods Frozen foods, frozen foods such as cooked frozen foods, canned fish and pastes, fish ham and sausages, fish paste products, marine delicacies, marine dried foods, marine products such as boiled fish, livestock canned and pasted products, livestock ham and sausages, Processed livestock products such as livestock delicacies, canned agricultural products, canned fruits, jams and marmalades, pickles, boiled beans, agricultural products Things such, Serial such processed agricultural products, baby food, baby food, sprinkled, Ochazuke glue, supplements and the like can be exemplified.

  As one aspect of the present invention, a cosmetic product comprising the plant sterol-containing composition of the present invention is provided. The cosmetic is not particularly limited, and examples thereof include skin lotion, emulsion, shampoo, rinse, hair cosmetic, foundation, lipstick, and moisturizing cream.

  It does not specifically limit as content of the plant sterol containing composition of this invention in food-drinks or cosmetics. What is necessary is just to contain the composition of sufficient quantity for ingestion of a plant sterol, and what is necessary is just to determine suitably according to the composition of the food / beverage products or cosmetics to which this composition is applied, or the individual | substance ingestion of this product. The content of the composition is, for example, preferably 0.001% to 50%, more preferably 0.01% to 20%, and still more preferably 0.1% to 10% in terms of plant sterol in food and drink. %. If it is less than this range, the expected effect is difficult to obtain, and if the concentration exceeds this range, the properties of the food or drink may be affected.

  The food / beverage products or cosmetics of this invention can add the plant sterol containing composition of this invention with respect to an existing food / beverage products or cosmetics, for example. Moreover, when preparing those food-drinks or cosmetics, it can prepare by previously adding the composition of this invention to a use raw material, or mix | blending together in a preparation process. If the food / beverage products or cosmetics which can express the desired effect of this invention are obtained, it will not specifically limit about the addition time and addition method of the composition of this invention to this product.

The food / beverage product or cosmetic containing the plant sterol-containing composition of the present invention contains a large amount of plant sterol, but since the plant sterol is stably emulsified or solubilized, white turbidity and crystals due to precipitation of the plant sterol Moreover, there is no precipitation, etc., sterol-derived roughness, and oiliness. Thus, according to the plant sterol-containing composition of the present invention, the plant sterol can be strengthened to foods and drinks or cosmetics without deteriorating the appearance, texture and feeling of use of the product.

  EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further more concretely, this invention is not limited only to this Example.

Preparation Example 1 Preparation of polyglycerin Sample: Great oil DE-1 (manufactured by Taiyo Kagaku: decaglycerin)
Great oil DE-2 (manufactured by Taiyo Kagaku: decaglycerin)
Great oil DI-1 (Taiyo Chemical Co., Ltd .: Diglycerin)
Reagents: Pyridine (manufactured by Wako Pure Chemical Industries), chlorophenylmethyl (manufactured by Wako Pure Chemical Industries, Ltd.)
Ethyl acetate (Wako Pure Chemical Industries, Ltd.)
Instruments: Thermometer, Dimroth, 3-neck flask, stirring device, decompression device, reflux device,
Separation funnel method;
Polyglycerin (Great Oil DE-1) and pyridine were added to a three-necked flask equipped with a thermometer, a Dimroth and a stirrer. To this was added chlorotriphenylmethyl, which is a reagent that selectively reacts with a primary hydroxyl group, and the mixture was stirred at 100 ° C. for 1 hour, returned to room temperature, and stirred for 24 hours. Further, most of the pyridine was removed from the reaction solution under reduced pressure. Water was added to the obtained reaction product, transferred to a separatory funnel, and extracted three times with ethyl acetate. The ethyl acetate layers were combined and concentrated. The obtained residue and acetic acid were added to a three-necked flask equipped with a thermometer, a Dimroth and a stirrer, and the mixture was heated to reflux for 8 hours to desorb the trimethylphenyl group. The above steps were repeated and purified polyglycerol was mixed to obtain a certain amount of polyglycerol B. Moreover, the same operation was performed also about Great oil DE-2 and Great oil DI-1, respectively, and polyglycerol C and D were obtained. Table 1 shows the hydroxyl value, primary hydroxyl group, and secondary hydroxyl group of the resulting polyglycerol.

  The hydroxyl value was calculated in accordance with the 7th edition Food Additives Official “Fats and Fats Test Method” or the standard fat and oil analysis test method.

Preparation Example 2
The residue obtained by concentrating the aqueous layer portion of Preparation Example 1 and acetic acid were added to a three-necked flask equipped with a thermometer, a Dimroth, and a stirrer and heated under reflux for 8 hours to desorb the trimethylphenyl group. The above steps were repeated and purified polyglycerol was mixed to obtain a certain amount of polyglycerol E. Table 1 shows the hydroxyl value, primary hydroxyl group, and secondary hydroxyl group ratio of the resulting polyglycerol.

Preparation Example 3 Preparation of polyglycerol fatty acid ester Sample: Polyglycerol, stearic acid, oleic acid, myristic acid, lauric acid listed in Table 1 Reagents: sodium hydroxide (Wako Pure Chemical Industries), phosphoric acid (Wako Pure Chemical Industries, Ltd.) )
Apparatus: Four-necked flask, decompression device with nitrogen gas injection, stirring device method;
The polyglycerin, fatty acid and sodium hydroxide listed in Table 1 were put into a four-necked flask and reacted at 250 ° C. while removing the produced water under a nitrogen stream, and after the reaction, phosphoric acid was added to obtain a polyglycerin fatty acid ester. . The prepared polyglycerol fatty acid ester is as shown in Table 2.

  The acid value was calculated according to the 7th edition Food Additives Official “Fats and Fats Test Method” or the Standard Oil and Fat Analysis Test Method.

Example 1 Preparation of plant sterol emulsion (1)
According to the blending ratio of formulation 1, using the polyglycerin fatty acid esters of preparations 1 to 12 described in Table 2, plant sterol emulsion formulations were prepared by the following method. In other words, glycerin (manufactured by Nippon Oil & Fats Co., Ltd.) was added with polyglycerin fatty acid ester separately heated and melted and heated to 80 ° C. or higher, and this was confirmed using a homomixer (manufactured by Special Machine Industries Co., Ltd.). The mixture was stirred at 5,000 rpm. A plant sterol (trade name “Phytosterol-FK” manufactured by Tama Seikagaku Co., Ltd .: phytosterol 90% or more) melted separately at 120 to 130 ° C. was added thereto and emulsified with a homomixer at 6,000 rpm. 6. The plant sterol emulsion preparation of comparative products 1-6 was obtained.

  Separately, a plant sterol emulsion preparation was prepared by the following method using the polyglycerin fatty acid ester of Preparation 3 described in Table 2 in accordance with the mixing ratio of Formulation 2. That is, a polyglycerol fatty acid ester separately heated and melted in glycerin was added and heated to 80 ° C. or higher, and this was stirred at 5,000 rpm while confirming the mixed state using a homomixer. Separately, plant sterol and monoglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., monomyristic acid glycerin ester) dissolved and mixed at 120 to 130 ° C. were added and emulsified with a homomixer at 6,000 rpm. A plant sterol emulsified preparation of Invention 7 was obtained.

  Table 3 shows the component composition ratios of the plant sterol preparations of Formula 1 and Formula 2.

  The emulsion stability was stored at 25 ° C., and the number of days elapsed until the generation of crystals was confirmed.

Table 4 shows the emulsion stability results of the plant sterol emulsion preparation.

Test Example 1 Preparation of Acid Sugar Solution While stirring 87 g of water, 10.8 g of fructose glucose solution sugar, 0.18 g of citric acid, and 0.04 g of trisodium citrate, 2.0 g of the plant sterol emulsion preparation of Example 1 was mixed. Then, after heat sterilization at a temperature of 93 ° C., a colorless transparent plastic bottle was hot-packed and cooled to obtain a translucent to milky acid sugar solution containing plant sterols.

  The dispersion stability was stored at 37 ° C. for 14 days and visually confirmed.

  The results of dispersion stability in the acid sugar solution are shown in Table 5.

<Dispersion stability>
A: Translucent solution with no precipitation or aggregation (letters visible through 100 ml beaker)
○: It is a cloudy solution, and no precipitation or aggregation is observed. Δ: It is a cloudy solution, and fine aggregates are recognized. ×: A precipitation is recognized.

Example 2 Preparation of plant sterol emulsion preparation (2)
A plant sterol emulsion preparation was prepared by the following method using the polyglycerin fatty acid ester shown in Table 2 according to the blending ratio of formulation 3. That is, polyglycerin fatty acid ester separately heated and melted in propylene glycol was added and heated to 80 ° C. or higher, and this was stirred at 500 rpm while confirming the mixed state using a blade stirrer (manufactured by Tokyo Rika Kikai Co., Ltd.). Separately, plant sterol (trade name “Phytosterol-FK” manufactured by Tama Biochemical Co., Ltd .: phytosterol 90% or more) and monoglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., monostearic acid glycerin ester) are used in an amount of 120 to 130. What was melt | dissolved and mixed at (degreeC) was added, and it emulsified at 600 rpm using the blade stirrer, and obtained the plant sterol formulation of this invention products 8-11 and the comparative products 7-10.

  Separately, sucrose fatty acid ester (trade name “Ryoto Sugar Ester S-1170” manufactured by Mitsubishi Chemical Foods Co., Ltd.) was used instead of polyglycerin fatty acid ester, and the plant sterol of Comparative Product 11 was treated in the same manner. A formulation was obtained.

  Separately, a plant sterol preparation of Comparative Product 12 was obtained in the same manner except that sorbitan sugar fatty acid ester (trade name “Sunsoft No. 61S” manufactured by Taiyo Kagaku Co., Ltd.) was used instead of polyglycerol fatty acid ester. It was.

  Table 6 shows the component composition ratio of the plant sterol preparation of Formula 3.

   The emulsification stability was confirmed after 30 days at 37 ° C. and then stored for 5 days in a refrigerator.

  Table 7 shows the results of emulsion stability of the plant sterol emulsion preparation.

<Emulsification stability>
◎: No difference from immediately after preparation ○: Slight crystal precipitation on the surface △: Crystal precipitation (about 1 to 10% of emulsion preparation)
X: Crystal precipitation (over about 10% of emulsion preparation)
XX: Crystal precipitation (over about 50% of emulsion preparation)
◎ and ○ are acceptable products.

Test Example 2 Preparation of Coffee Beverage About 10 times weight of boiling water was added to 250 g of coffee beans (L value: 18), and Bx. 2500 g coffee extract of 2.5 was obtained. A coffee drink was prepared according to the ratio shown in the following formulation 4 using this extract and granulated sugar, milk, baking soda, and an emulsion stabilizer formulation for coffee (trade name “Sunsoft Super V-302” manufactured by Taiyo Kagaku Co., Ltd.). . To this coffee beverage, 1.0% of the inventive plant sterol emulsified preparation obtained in Example 2 and a comparative product were added, and then homogenized with a homogenizer (150 kg / cm ² ) and filled into a 190 ml can. This was sterilized at 121 ° C. for 30 minutes to obtain a canned coffee drink.

  About the preparation ratio of the coffee drink of prescription 4, it is as Table 8.

  The dispersion stability was stored at 55 ° C. for 8 weeks, then transferred to a beaker and visually confirmed.

  Table 9 shows the results of the dispersion stability in the coffee beverage.

<Dispersion stability>
(Double-circle): It disperse | distributes uniformly and does not recognize precipitation, aggregation, and oil floating.
○: Evenly dispersed, but slightly floating oil.
Δ: Precipitation and oil floating are observed. ×: White agglomerates are present, and precipitation and oil floating are recognized. ◎ and ○ are acceptable products.

Test Example 3 Preparation of sour milk beverage 88.5 g of water, 7.2 g of granulated sugar, and 0.3 g of pectin were dissolved by heating, and 4.0 g of defatted sweetened milk was mixed with the product cooled to 20 to 30 ° C. While stirring the solution, the pH was adjusted to 3.8 with a 50% aqueous solution of citric acid, and the inventive product obtained in Example 2 and a comparative plant sterol emulsion 1.5% were mixed. This beverage was homogenized with a homogenizer (150 kg / cm ² ), sterilized by heating at a temperature of 93 ° C., filled in a 350 ml plastic bottle and cooled to obtain an acid milk beverage.
The dispersion stability was stored at 37 ° C. for 2 months and visually confirmed.
<Dispersion stability>
(Double-circle): It disperse | distributes uniformly and does not recognize precipitation, aggregation, and oil floating.
○: Although uniformly dispersed, slight precipitation is observed.
Δ: Although dispersed, precipitation and aggregation are observed.
X: It is non-uniform | heterogenous and precipitation, aggregation, and oil floating are recognized.
◎ and ○ are acceptable products.

Moreover, about the acid milk drink preserve | saved for two months at 37 degreeC, the sensory evaluation was performed by 10 panelists who were well trained about the change of the flavor, and the degree of roughness. As a reference for comparison, a sample stored in a refrigerator at 5 ° C. was used, and the difference with respect to this was shown by a numerical value.
In addition, the score of evaluation in Table 10 is an average score of each panel scored according to the following criteria.
<Sensory evaluation>
Equivalent to refrigerated sample (no change): 5 points Slightly changed compared to refrigerated sample: 4 points Slightly changed compared to refrigerated sample, feel rough: 3 points Significantly changed compared to refrigerated sample And feels rough: 2 points Significantly changes compared to refrigerated samples and feels rough: 1 point

  Table 10 shows the dispersion stability in the sour milk beverage and the sensory evaluation results.

Test Example 4 Preparation of emulsion (emollient cream) An emulsion was prepared according to the ratio shown in Formulation 5. Propylene glycol, glycerin and triethanolamine were added to purified water and mixed by heating to obtain an aqueous phase. Further, other components were mixed at 70 ° C., and this oil phase part was added to the aqueous phase part for preliminary emulsification. 5.0% of the plant sterol emulsion preparation of the present invention and comparative product obtained in Example 2 were added thereto, and then uniformly emulsified with a homomixer. After emulsification, the emulsion was cooled to 30 ° C. to obtain an emulsion. .

  About the preparation ratio of the emulsion (emollient cream) of the prescription 5, it is as Table 11.

  The dispersion stability was stored at 50 ° C. for 1 month and visually confirmed.

  Table 12 shows the results of the dispersion stability of the emulsion.

<Dispersion stability>
(Double-circle): It disperse | distributes uniformly and does not recognize precipitation, aggregation, and oil floating.
○: Although uniformly dispersed, slight precipitation is observed.
Δ: Dispersed, but precipitation, aggregation, and oil floating are observed.
X: It is non-uniform | heterogenous and precipitation, aggregation, and oil floating are recognized.
◎ and ○ are acceptable products.

Examples of the present invention and the target product are as follows.
(1) A plant sterol and a polyglycerin fatty acid ester obtained by esterifying a polyglycerin having a hydroxyl value of 1200 or less and a primary hydroxyl group of 50% or more of all the hydroxyl groups and a fatty acid are contained as essential components. A plant sterol-containing composition.
(2) The plant sterol-containing composition according to (1), wherein the primary hydroxyl group of polyglycerol is 55% or more.
(3) The plant sterol-containing composition according to (1), wherein the primary hydroxyl group of polyglycerol is 60% or more.
(4) The plant sterol composition according to any one of (1) to (3), wherein the composition is an oil-in-polyol (O / D type) emulsion.
(5) The plant sterol composition according to any one of (1) to (4), wherein the polyhydric alcohol is glycerin.
(6) The plant sterol composition according to any one of (1) to (4), wherein the polyhydric alcohol is propylene glycol.
(7) The plant sterol composition according to the above (1) to (6), wherein plant sterol and monoglycerin fatty acid ester are dissolved in advance at high temperature.
(8) The plant sterol composition according to the above (1) to (7), wherein the blending amount of the plant sterol is 15% or more.
(9) Food / beverage products containing the plant sterol containing composition in any one of said (1)-(8).
(10) A cosmetic comprising the plant sterol-containing composition according to any one of (1) to (8).

  As shown in the above test examples, the plant sterol-containing composition of the present invention prepared with a specific polyglycerin fatty acid ester crystallizes, precipitates, etc., a plant sterol that could not be stably dispersed conventionally. It is clear that it can be added to foods and beverages or cosmetics without causing any problems.

Claims (4)

A plant comprising, as an essential component, a plant sterol and a polyglycerol fatty acid ester obtained by esterifying a polyglycerol having a hydroxyl value of 1200 or less and a primary hydroxyl group of 50% or more of all hydroxyl groups and a fatty acid. A sterol-containing composition. The plant sterol composition according to claim 1, wherein the composition is an oil-in-polyol (O / D) emulsion. The food-drinks containing the plant sterol containing composition of Claim 1 or Claim 2. A cosmetic comprising the plant sterol-containing composition according to claim 1 or 2.