JP6027749B2 - Oil-soluble antioxidant and method for producing the same - Google Patents

Description

The present invention relates to an oil-soluble antioxidant containing a water-soluble antioxidant component derived from a natural product, particularly catechins derived from green tea, and a method for producing the same.
More specifically, an edible fat or oil-containing food obtained by mixing a catechin derived from green tea, an aqueous phase containing water and a hydrophilic emulsifier, and an oil phase containing a medium-chain fatty acid triglyceride and a lipophilic emulsifier. The present invention relates to an oil-soluble antioxidant for use in water and a method for producing the same.

Antioxidants are food additives used for the purpose of preventing deterioration of food due to oxidation. As chemically synthesized products, disodium calcium ethylenediaminetetraacetate, erythorbic acid, dl-α-tocopherol, propyl gallate and the like are used.
As natural products, sesame extract, tea catechin, extracted tocopherol (derived from vegetable oil such as soybean, wheat germ oil, rapeseed oil), rosemary extract, gallic acid extracted from Nurde, γ-oryzanol extracted from rice bran, Cineol extracted from eucalyptus leaves and monosaccharide-amino acid complex (melanoidin) are used.

Coupled with the recent consumer boom in natural foods and natural products, natural product-derived antioxidants have attracted attention, especially catechins derived from green tea that have been ingested daily and have been confirmed to be safe since ancient times. Is attracting attention.
However, the use of catechins has been limited because they are water-soluble and insoluble in fats and oils, and because of their strong bitterness and astringency, they may impair the original taste of the food to be added.

Various techniques have been proposed to solve these problems and increase the application range and utility value as an antioxidant.
Patent Document 1 discloses (A) catechins of 1 to 40 weights as an oil-soluble antioxidant composition capable of uniformly solubilizing catechins, which have been restricted in use because they are insoluble in fats and oils, in fats and oils. Parts, (B) 1 to 40 parts by weight of water or / and alcohol, (C) 1 to 35 parts by weight of an emulsifier having 6 to 14 HLB, (D) 5 to 70 parts by weight of a polyglycerol condensed ricinoleic acid ester, and (E ) A composition containing 0.5 to 30 parts by weight of enzymatically decomposed lecithin, wherein the aqueous phase containing the components (A), (B), and (C) is solubilized in the component (D) An antioxidant composition characterized in that it is dispersed in an aqueous solution is proposed.

  Patent Document 2 discloses (A) non-polymer catechins 0.03 to 0.6 for the purpose of providing an emulsified beverage composition with reduced bitterness and astringency derived from non-polymer catechins. An emulsified beverage composition containing mass%, (B) liquid oil and fat, and (C) an emulsifier is disclosed.

  In Patent Document 3, polyphenols are added to polyhydric alcohol fatty acid esters in order to keep polyphenols stable for a long period of time and to provide a water-dispersible polyphenol preparation excellent in taste and bioabsorbability. A first step of micronization in the contained oil and fat, and a step of emulsifying the oil and fat containing the micropolyphenols obtained in the first step into an oil-in-water droplet type in the presence of a polyhydric alcohol fatty acid ester. A polyphenol preparation obtained by two steps has been proposed.

  Furthermore, in Patent Document 4, for the purpose of providing an emulsion-containing composition that contains catechin and the like and does not cause aggregation or the like and has excellent emulsion stability, (1) the number of carbon atoms of the oil-soluble component and the fatty acid is 18 An oil-in-water emulsion particle formed with an emulsifier containing a sucrose fatty acid ester that is less than (2), and (2) an emulsion-containing composition having a pH of 2.5 to 6.5, including catechins. ing.

However, although the purpose of dissolving catechins in fats and oils is achieved to some extent, practical techniques that reduce the bitter taste derived from catechins and satisfy all the conditions of high solubility in fats and oils and antioxidant power are still provided. Not.
For example, in the invention of Patent Document 1, solubilization of catechins in fats and oils is attempted by using in combination three types of emulsifiers, an enzymatically decomposed lecithin, an emulsifier having an HLB of 6 to 14, and a polyglycerin condensed ricinoleic acid. In this invention, enzymatically decomposed lecithin is essential for transparency, but in order to solubilize enzymatically decomposed lecithin, it is necessary to mix the mixture while heating. May reduce antioxidant capacity.

When an antioxidant is added to edible oils or fat-containing foods, it must be transparent and finely and uniformly dispersed in the food without white turbidity in order to maintain the product value and good appearance of the product. Is required for antioxidants.
Therefore, the present inventor examined a method for transparently solubilizing catechins in fats and oils without using enzymatically degraded lecithin.

JP-A-6-279758 JP 2009-106187 A JP 2001-316259 A JP 2008-280256 A

  The problem of the present invention is that water-soluble antioxidant components derived from natural products that are insoluble in fats and oils, in particular, catechins derived from green tea can be uniformly and uniformly dispersed in fats and oils, and do not exhibit the bitter and astringent taste peculiar to catechins. An object of the present invention is to provide an antioxidant having an excellent antioxidant effect and a method for producing the same.

The present inventor has focused on reducing the particle size of catechin emulsions in order to disperse water-soluble catechins in oils and fats, and is an emulsifier excellent in hydrophilicity used for the preparation of the aqueous phase. And the combination of the kind of emulsifier excellent in the lipophilic property used for preparation of an oil phase part was examined earnestly.
As a result, it was found that even if lecithin was not used to enhance emulsifying power, it could be present in the state of fine particles having an average particle size of 120 nm or less in fats and oils and could be dispersed transparently in the fats and oils. Furthermore, it was found that the bitter taste of catechin is reduced while maintaining the antioxidant ability by dispersing in the fine particle state.
Based on these findings, the present inventor has completed an oil-soluble antioxidant.

That is, the present invention is as follows.
[1] An oil-soluble antioxidant containing a water-soluble antioxidant component derived from a natural product and having an average particle size of 40 to 120 nm that can be dispersed in oils and fats;
[2] A medium chain fatty acid triglyceride , a polyglycerin condensed ricinoleic acid ester, and a water phase part obtained by mixing a water-soluble antioxidant component derived from a natural product, a polyglycerin fatty acid ester having an HLB of 14 to 16 and water. The oil-soluble antioxidant, which is obtained by adding and emulsifying an oil phase part obtained by mixing
[3] The oil-soluble antioxidant described above further comprising a natural product-derived extracted tocopherol in the oil phase part;

[4] The oil-soluble antioxidant as described above, wherein the natural product-derived antioxidant component is a catechin derived from green tea;
[5] The polyglycerol fatty acid ester having an HLB of 14 to 16 is selected from the group consisting of decaglycerol monocaprylate, decaglycerol monocaprate, decaglycerol monolaurate, decaglycerol monomyristate and decaglycerol monooleate. And at least one oil-soluble antioxidant as described above;

[6] Edible oil or fat-containing food to which the oil-soluble antioxidant described above is added;
[7] A step of mixing a catechin derived from green tea, water and a polyglycerin fatty acid ester having an HLB of 14 to 16 to obtain an aqueous phase part,
A step of obtaining an oil phase part by mixing polyglycerin condensed ricinoleate, medium chain fatty acid triglyceride and optionally extracted tocopherol derived from natural products, and
A method for producing an oil-soluble antioxidant containing tea catechins, comprising adding 100 to 500 parts by mass of the oil phase part to 100 parts by mass of the water phase part.

  Even if a tea extract containing a high concentration of catechins is used, the product does not have a bitter taste, and it is uniformly dispersed with fine particles in edible oils and fat-containing foods, so that the transparency of the product can be maintained. Furthermore, it is possible to provide an oil-soluble antioxidant excellent in anti-oxidant power.

Hereinafter, the present invention will be described in detail according to embodiments.
[1] Oil-soluble antioxidant (1) Active ingredient of oil-soluble antioxidant The active ingredient of the antioxidant of the present invention is a water-soluble antioxidant ingredient derived from natural products, such as vitamin C, glutathione, polyphenol And catechins.
Among these, catechins derived from green tea are preferable. Specific examples of catechins include catechin (3,3 ′, 4 ′, 5,7-pentahydroxyflavan), epicatechin, epigallocatechin, gallocatechin, epigallocatechin gallate, and epicatechin gallate. However, a green tea extract rich in these catechins can be used.

  The tea here means the buds, leaves, and stems of the camellia tea tree (Camellia sinensis var.), Which can be used regardless of varieties or origins. It may have been pretreated. There are unfermented, semi-fermented, and fermented tea pretreatment methods, but because of the high content of catechins, green tea that is unfermented tea (sencha, gyokuro, kabusecha, bancha, tamamocha, matcha, hojicha, kettle Fried tea, tencha, etc.) are preferred.

  The green tea extract is preferably prepared by extracting tea with water and / or a water-soluble organic solvent. Examples of the water-soluble organic solvent include solvents such as methanol, ethanol, 2-propanol, and acetone. 1 type, or 2 or more types of mixtures can be used and it is used with the form of aqueous solution as needed. The solvent used for extraction is preferably water or an aliphatic alcohol having 2 to 4 carbon atoms such as ethanol, propanol, or butanol, and most preferably water, ethanol, or a mixture thereof from the viewpoint of safety to the human body and handleability. Although the quantity of the solvent used for extraction can be selected arbitrarily, generally 10-200 mass parts is used with respect to 1 mass part of tea, Preferably 15-25 mass parts is used. The temperature and time of extraction can be arbitrarily determined and are not particularly limited, but are suitable at 10 to 100 ° C. for 1 minute to 2 hours, preferably 5 minutes to 1 hour.

  The obtained extract is rich in catechins, and after removing insolubles, it can be concentrated and used as it is as a raw material for the emulsion, but the extract can be further purified with a synthetic adsorbent. . As the synthetic adsorbent used in the present invention, the matrix is styrene, such as Amberlite (registered trademark) XAD-16 (manufactured by Organo Corporation), styrene-divinylbenzene, such as Diaion (registered trademark) HP- 20 (Mitsubishi Chemical Corporation), acrylic, for example Diaion WK-10 (Mitsubishi Chemical Corporation), methacrylic, for example Diaion HP-2MG (Mitsubishi Chemical Corporation), acrylic ester, for example, amber Light XAD-7 (manufactured by Organo Corporation), amide-based, such as Amberlite XAD-11 (manufactured by Organo Corporation), dextran-based, such as Sephadex (registered trademark) G-25 (manufactured by Amersham Pharmacia Biotech), polyvinyl-based Used by Diaion FP-II (Mitsubishi Chemical Corporation) it can. In addition, the synthetic adsorbent treatment method in the present invention may be performed by a conventional method. For example, a method of feeding a tea extract at a constant flow rate to a synthetic adsorbent packed in a column, extraction, There is a method in which a synthetic adsorbent is added to an extract charged in a kettle and the synthetic adsorbent is separated after stirring for a certain time. There is no particular restriction on the method, and it can be selected according to the purpose.

  Extracts from which unnecessary flavor components derived from tea have been removed by purification with a synthetic adsorbent can be emulsified as they are, but they can also be separated by high-performance liquid chromatography using an octadecyl silica (ODS) column. It can also be used after purification.

  Further, the tea extract can be used as a concentrate by means of vacuum distillation concentration, freeze concentration or membrane concentration, or powdered by freeze drying or the like. Further, the extract may be formulated as follows. Generally dissolved in a (mixed) solvent such as water, ethanol, glycerin, propylene glycol, triethyl citrate, etc. at a suitable concentration (specifically, water / ethanol, water / ethanol / glycerin, water / glycerin, etc. In addition, dextrin, sucrose, pectin, chitin, etc. can be added to this as necessary, and these can be further concentrated to form a paste-like extract. (Dextrin etc.) can be added to form a powder by spray drying or the like, and various dosage forms can be adopted depending on the application.

In the present invention, the commercial product manufactured as described above (“TEA1030 GREEN TEA EXTRACT 70% CATECHINS (trade name)” manufactured by SYNTHITE INDUSTRIES LIMITED) (containing 70% catechins) is used as it is as an antioxidant component. Can do.
In addition, catechins and other water-soluble antioxidant components can be used in appropriate combination.

(2) Manufacturing method of oil-soluble antioxidant In order to apply a water-soluble antioxidant derived from catechins to edible oils or oil-containing foods, it is treated with an emulsifier to give an emulsion. It is necessary.
In the present invention, in an edible oil or fat-containing food, a water phase part is prepared with a hydrophilic emulsifier for uniform fine dispersion in a transparent state, and added to the oil phase part separately prepared with a lipophilic emulsifier. To produce an oil-soluble antioxidant.

(A) Preparation of aqueous phase part Polyglycerin having preferably 60 to 360 parts by mass of distilled water (preferably 100 to 200 parts by mass) and HLB of 14 to 16 with respect to 100 parts by mass of catechins derived from green tea 10-80 parts by mass (preferably 30-50 parts by mass) of the fatty acid ester is mixed and sufficiently stirred with a mixer, and completely dissolved at a temperature of 30-50 ° C. to prepare an aqueous phase part.

The polyglycerin fatty acid ester is a polyglycerin obtained by dehydrating and condensing glycerin together with an ester bond of a fatty acid.
The polyglycerol fatty acid ester having an HLB of 14 to 16 is preferably selected from decaglycerol monocaprylate, decaglycerol monocaprate, decaglycerol monolaurate, decaglycerol monomyristate and decaglycerol monooleate. These are commercially available as hydrophilic surfactants or emulsifiers and can be used as they are.
Furthermore, citric acid, tartaric acid, malic acid, ascorbic acid, and the like can be added as necessary as a synergist for enhancing water solubility and enhancing emulsification.

Here, HLB is Hydrophilic-Lypophilic Balance, which is a relative numerical value of the ratio of hydrophilicity to lipophilicity possessed by a surfactant, and a surfactant having a large HLB value is A thing with a large hydrophilicity, on the contrary, a thing with small hydrophobicity (lipophilicity) is large.
For the nonionic surfactant, for example, the following formula is used.
HLB = 7 + 11.7log (Mw / Mo)
[Wherein, Mw represents the partial molecular weight of the hydrophilic group, and Mo represents the partial molecular weight of the lipophilic group]

(B) Preparation of oil phase part Polyglycerin-condensed ricinoleic acid ester 25-34,000 parts by mass (preferably 50-250 parts by mass) with respect to 100 parts by mass of medium-chain fatty acid triglyceride, and if necessary, antioxidant power In order to increase the viscosity, 0.2 to 53,000 parts by mass (preferably 10 to 110 parts by mass) of an extracted tocopherol derived from a natural product is mixed and sufficiently stirred with a mixer to prepare an oil phase part.

  As the medium chain fatty acid triglyceride, it is preferable to use a triglyceride of a fatty acid having 6 to 12 carbon atoms (caproic acid, caprylic acid, capric acid, lauric acid), and a commercially available product can be appropriately purchased and used.

  Polyglycerin condensed ricinoleic acid ester is also called PGPR, and is an emulsifier with strong lipophilicity in which polyglycerin obtained by polymerizing 2 to 10 mol of glycerin and condensed ricinoleic acid obtained by condensing 3 to 5 mol of ricinoleic acid are combined. The medium chain fatty acid triglyceride is used because it is a highly viscous liquid and not soluble in water but soluble in fats and oils.

Extracted tocopherol derived from natural products is a tocopherol obtained as a by-product when refining vegetable oils such as soybean oil, wheat germ oil, rapeseed oil, etc., and has the same antioxidant effect as synthetic dl-α-tocopherol. The extracted tocopherol is appropriately blended as necessary to enhance the antioxidant power.
Furthermore, an extracted tocopherol and other lipophilic antioxidant components can be used in appropriate combination.

(C) Emulsification 100 to 500 parts by mass (preferably 100 to 300 parts by mass) of the oil phase part is added to 100 parts by mass of the water phase part, and the oil-soluble antioxidant of the present invention is obtained. It is done.
The emulsification is preferably performed using a homomixer and stirring at 4,000 to 14,000 rpm for 20 to 40 minutes.

In contrast to the oil-soluble antioxidant of the present invention, other antioxidants, salt, fragrance, saccharide, colorant, emulsifier, preservative, seasoning, sweetener, color former within the scope of the present invention. In addition, additives such as a pH adjusting agent may be blended.
Moreover, the form of the oil-soluble antioxidant of the present invention is not particularly limited, and examples thereof include liquid, powder, and capsule.

(D) Properties of oil-soluble antioxidant The oil-soluble antioxidant of the present invention has an average particle size of 40 to 120 nm, and when added to fats and oils, it does not become cloudy and does not become cloudy. Transparency can be maintained.
In the present application, the average particle diameter is obtained by a dynamic light scattering method and a photon correlation method. In the dynamic light scattering method, measurement is performed by applying a laser beam to particles in Brownian motion and detecting the scattered light with a photomultiplier tube (PMT). In the photon correlation method, temporal fluctuations in the scattered light intensity (fluctuations in the number of photons of scattered light) are measured. In other words, the diffusion coefficient is obtained by grasping the random intensity fluctuations caused by the changing pattern of the diffusing particles with an accurate time scale (autocorrelation function), and the particle diameter is derived from the Einstein-Stokes equation. It is.

(3) Edible fats and oils or fat-containing foods The edible fats and oils for which the oil-soluble antioxidant of the present invention is used are fatty oil (liquid at normal temperature) and fat (solid at normal temperature).
Examples of fatty oils include salad oil, white squeezed oil, corn oil, soybean oil, sesame oil, rapeseed oil (canola oil), rice oil, coconut oil, coconut oil, safflower oil (safflower oil), palm kernel oil, coconut oil, cottonseed oil , Sunflower oil, camellia oil, olive oil, peanut oil, almond oil, avocado oil, hazelnut oil, walnut oil, grape seed oil, mustard oil, lettuce oil, fish oil (whale oil, salmon oil, liver oil).

Examples of fats include cocoa butter, palm oil, lard (tallow fat), het (beef tallow), chicken oil, rosin, sheep fat, horse fat, Schmalz, shortening, milk fat, butter, margarine, ghee, and hardened oil. .
Examples of the fat-containing food to which the oil-soluble antioxidant of the present invention is added include margarine, confectionery (chocolate, ice cream, etc.) and beverages containing the edible fat.

The amount of the oil-soluble antioxidant of the present invention added to the edible oil or fat-containing food is usually used so that it is contained by 0.01 to 10% by weight in the edible oil or fat-containing food, preferably It is used at 0.03 mass% to 5 mass%, more preferably 0.05 mass% to 3 mass%.
When the addition amount is less than 0.01% by mass, the antioxidant effect may not be sufficient, and when the addition amount exceeds 10% by mass, the bitterness and astringency of catechins may emerge.

  The oil-soluble antioxidant of the present invention may be added to foods before the production process of edible oils or fat-containing foods, during production, or used in products after production. However, it is not particularly limited.

EXAMPLES Next, although an Example is shown and this invention is demonstrated further more concretely, this invention is not limited to these Examples.
[Production Example 1] (Production of oil-soluble antioxidant)
(1) Water phase part Green tea extract powder (TEA1030 GREEN TEA EXTRACT 70% made by SYNTHITE INDUSTRIES LIMITED
14 g of CATECHINS (trade name) containing 70% catechins, 16 g of distilled water and 4 g of decaglycerin monolaurate (“SY Glyster ML750 (trade name)” manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.) were thoroughly stirred with a mixer. The aqueous phase was prepared by completely dissolving at 0 ° C.

(2) Oil phase part Polyglycerin condensed ricinoleic acid ester (“Sunsoft No.
818R (trade name) ") 26 g, 26 g of medium chain fatty acid triglyceride (" MM ester E7000 (trade name) "manufactured by PTMusium Mas) and tocopherol derived from soybean (" Emix 70L (trade name) "manufactured by Eisai Food Chemical Co., Ltd.) ) 14 g was added and sufficiently stirred and homogenized to prepare an oil phase part.

(3) Mixing of water phase part and oil phase part The oil phase part is added to the water phase part and mixed, and then emulsified with a homomixer ("TK Robotics" manufactured by Primics Co., Ltd.) at 12,000 rpm for 30 minutes. A soluble antioxidant was prepared.
Table 1 shows the components and amounts contained in the oil-soluble antioxidant obtained. In addition, the antioxidant composition of the cited reference 1 was described for the comparison.

[Test Example 1] (Measurement of average particle size and transparency)
The oil-soluble antioxidant of Production Example 1 was added to medium-chain fatty acid triglyceride so as to be 2%, and the mixture was slowly stirred at room temperature.
To the additive-free product as a control, medium chain fatty acid triglyceride was added to 2% instead of the oil-soluble antioxidant.
Moreover, the oil-soluble antioxidant having an average particle diameter of 60 to 230 nm is emulsified so as to have the respective average particle diameters by changing the rotation speed of the mixer when the water phase part and the oil phase part are mixed and emulsified. Made a state.
The average particle size was measured using a particle size meter ("ELS-Z2" manufactured by Otsuka Electronics Co., Ltd.).
As shown in Table 2, it was found that the average particle diameter was transparent at 60 nm and 120 nm.

[Test Example 2] (Sensory evaluation)
The oil-soluble antioxidant of Production Example 1 was added to corn oil so as to be 10%, and the mixture was slowly stirred at room temperature.
To the additive-free product as a control, medium-chain fatty acid triglyceride was added to 10% instead of the oil-soluble antioxidant.
Moreover, the oil-soluble antioxidant having an average particle diameter of 60 to 230 nm is emulsified so as to have the respective average particle diameters by changing the rotation speed of the mixer when the water phase part and the oil phase part are mixed and emulsified. Made a state.
Sensory evaluation of the taste of corn oil was conducted by six skilled panelists. Six people discussed and evaluated as follows. The results are shown in Table 2.
Evaluation scale ○: Astringency is not felt.
Δ: Slight astringency is felt
X: Astringency is felt.

[Test Example 3] (Measurement of absorbance)
The oil-soluble antioxidant of Production Example 1 was added to corn oil at 0.05% and stirred slowly at room temperature. To the additive-free product as a control, medium-chain fatty acid triglyceride was added to 0.05% instead of the oil-soluble antioxidant.
Moreover, the oil-soluble antioxidant having an average particle diameter of 60 to 230 nm is emulsified so as to have the respective average particle diameters by changing the rotation speed of the mixer when the water phase part and the oil phase part are mixed and emulsified. Made a state.
The turbidity of 660 nm was measured with a spectrophotometer (“V-560” manufactured by JASCO Corporation). The results are shown in Table 2.

  The absorbance at 660 nm is affected by the liquid color such as yellow or brown in the background. Therefore, when the background is yellow, the absorbance at 660 nm is 0.04 or less, and when the background is brown, It exhibits transparency at an absorbance of 660 nm of 0.14 or less.

[Test Example 4] (Measurement of antioxidant power)
The oil-soluble antioxidant of Production Example 1 was added to corn oil at 0.05% and stirred slowly at room temperature.
To the additive-free product as a control, medium-chain fatty acid triglyceride was added to 0.05% instead of the oil-soluble antioxidant.
Moreover, the oil-soluble antioxidant having an average particle diameter of 60 to 230 nm is emulsified so as to have the respective average particle diameters by changing the rotation speed of the mixer when the water phase part and the oil phase part are mixed and emulsified. Made a state.
Antioxidant titers were measured using an automatic oil / fat stability test apparatus ("Lancimat E679 type" manufactured by Shibata Scientific Instruments Co., Ltd.). The results are shown in Table 2.

  Antioxidant titer is the detection time of volatile component solution by oxidation of oil and fat of each sample, where 100 is the time for detection of volatile component solution by oxidation from the oil-free antioxidant additive product as a control. Represents. Therefore, a larger number means that oxidation is suppressed.

[Production Examples A1 to A6] (Examination of emulsifier in aqueous phase)
For the polyglycerin fatty acid ester of the hydrophilic emulsifier used in the water phase part, the oil-soluble antioxidants A1 to A6 are produced using a1 to a6 having different carbon chain lengths and HLBs, and the lipophilicity used in the oil phase part. The suitability of the combination with the emulsifier polyglycerol condensed ricinoleic acid ester (b1) was examined.

(1) Manufacture of oil-soluble antioxidants Green tea extract powder (TEA1030 GREEN TEA EXTRACT 70% manufactured by SYNTHITE INDUSTRIES LIMITED)
14 g of CATECHINS (trade name) containing 70% catechins), 16 g of distilled water and 4 g of various hydrophilic emulsifiers were sufficiently stirred with a mixer and completely dissolved at 40 ° C. to prepare an aqueous phase part.
26 g of polyglycerin condensed ricinoleic acid ester (“Sunsoft No. 818R (trade name)” manufactured by Taiyo Kagaku Co., Ltd.), 26 g of medium chain fatty acid triglyceride (“MM ester E7000 (trade name)” manufactured by PTMusium Mas) and soybean-derived tocopherol 14 g (“Emix 70L (trade name)” manufactured by Eisai Food Chemical Co., Ltd.) was added and sufficiently stirred and homogenized to prepare an oil phase part.
The oil phase part is added to the aqueous phase part prepared previously and mixed, and then emulsified with a homomixer (“TK Robotics” manufactured by PRIMIX Corporation) for 30 minutes to obtain an oil-soluble antioxidant composition. It was.

(2) Evaluation method and evaluation results Whether the emulsion was stably emulsified was determined by visual observation after storage under abuse conditions (50 ° C, stored for 3 days). The results are shown in Table 3. A circle represents a uniform emulsified state, and a cross represents a non-emulsified state.
Moreover, the average particle diameter was measured using a particle size measuring instrument (“ELS-Z2” manufactured by Otsuka Electronics Co., Ltd.).
From the results in Table 3, it was revealed that a combination of a polyglycerol fatty acid ester having an HLB of 14 to 16 (a2) to (a6) and a polyglycerol condensed ricinoleic acid ester (b1) is suitable.

[Production Examples B1 to B4] (Examination of emulsifier in oil phase part)
For the lipophilic emulsifier used for the oil phase part, in addition to the polyglycerin condensed ricinoleic acid ester (b1), a commercially available lipophilic emulsifier having a small HLB value is selected and used (b2 to b4). A combination of hydrophilic emulsifier decaglycerin monolaurate ("SY Glister ML-750 (trade name)" manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.)) (a3), which produces soluble antioxidants B1 to B4 and is used in the aqueous phase We examined the suitability of.

(1) Manufacture of oil-soluble antioxidants Green tea extract powder (TEA1030 GREEN TEA EXTRACT 70% manufactured by SYNTHITE INDUSTRIES LIMITED)
CATECHINS (trade name) "contains 70% catechins" 14g, distilled water 16g and decaglycerin monolaurate ("SY Glister ML-750 (trade name)" manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.), carbon chain length is 12, HLB 14.8) 4 g was sufficiently stirred with a mixer and completely dissolved at 40 ° C. to prepare an aqueous phase.
26 g of various lipophilic emulsifiers were added to 26 g of medium-chain fatty acid triglyceride (“MM ester E7000 (trade name)” manufactured by PTMusium Mas) and 14 g of soybean-derived tocopherol (“Emix 70L (trade name)” manufactured by Eisai Food Chemical Co., Ltd.). The oil phase part was prepared by adding and sufficiently stirring and homogenizing.
The oil phase part is added to the aqueous phase part prepared previously and mixed, and then emulsified with a homomixer (“TK Robotics” manufactured by PRIMIX Corporation) for 30 minutes to obtain an oil-soluble antioxidant composition. It was.

(2) Evaluation method and evaluation results Whether the emulsion was stably emulsified was determined by visual observation after storage under abuse conditions (50 ° C, stored for 3 days). The results are shown in Table 4. A circle represents a transparent and uniform emulsified state, and a cross represents a non-emulsified state.
Further, the average particle size of the oil-soluble antioxidant was measured in the same manner as in Test Example 3.
From the results in Table 4, it was revealed that a combination with polyglycerin condensed ricinoleic acid ester (b1) is suitable as a lipophilic emulsifier.

[Production Examples 2 to 6] (Examination of blending amount of green tea extract and emulsifier)
In Production Example 1, an oil-soluble antioxidant was produced in the same manner except that the amount of each raw material added was changed.

Table 5 shows the amount of each raw material added, the average particle size of the obtained oil-soluble antioxidant, and the evaluation results of the emulsified state immediately after production and after storage at 50 ° C. for 3 days. In addition, (circle) mark represents the transparent and uniform emulsified state, and x mark represents the state which is not emulsified.
From the results in Table 5, 7-18% of green tea extract (5-13% as catechin concentration), 2-5% of decaglycerol monolaurate, 13 of polyglycerol condensed ricinoleate in oil-soluble antioxidant It was revealed that the addition of ˜34% is suitable for the stability of emulsification.

  Water-soluble antioxidant components derived from natural products that are insoluble in fats and oils, especially catechins derived from green tea, can be uniformly and transparently dispersed in edible fats and oil-containing foods, and without exhibiting the bitter and astringent taste peculiar to catechins, Furthermore, the oil-soluble antioxidant excellent in the antioxidant effect and the manufacturing method thereof can be provided.

Claims (11)

Catechins that are water-soluble antioxidant components derived from natural products as water phase components, polyglycerin fatty acid esters and water having 14 to 16 HLB, and fatty acid triglycerides and polyglycerin having 6 to 12 carbon atoms as oil phase components An oil-soluble antioxidant that is an emulsion containing a condensed ricinoleic acid ester and has an average particle size of catechin emulsion particles of 40 to 120 nm and can be transparently dispersed in fats and oils. The water phase component is composed of 10 to 80 parts by mass of polyglycerin fatty acid ester having an HLB of 14 to 16 and 60 to 360 parts by mass of water with respect to 100 parts by mass of catechins, and the oil phase component has 6 to 12 carbon atoms. The oil-soluble antioxidant according to claim 1, comprising 25 to 34,000 parts by mass of a polyglycerol condensed ricinoleic acid ester with respect to 100 parts by mass of a certain fatty acid triglyceride. Furthermore, the oil-soluble antioxidant of Claim 1 or 2 in which the extraction phase tocopherol derived from a natural product is contained in an oil phase component .   The oil-soluble antioxidant according to claim 3, wherein the blending amount of the natural product-derived extracted tocopherol is 0.2 to 53,000 parts by mass with respect to 100 parts by mass of the fatty acid triglyceride having 6 to 12 carbon atoms. .   The oil-soluble antioxidant according to any one of claims 1 to 4, wherein the water-soluble antioxidant component derived from a natural product is a catechin derived from green tea.   The polyglycerin fatty acid ester having an HLB of 14 to 16 is at least one selected from the group consisting of decaglycerin monocaprylate, decaglycerin monocaprate, decaglycerin monolaurate, decaglycerin monomyristate, and decaglycerin monooleate. The oil-soluble antioxidant according to any one of claims 1 to 5, which is a seed. Edible fats or fat-containing food containing the oil-soluble antioxidant according to any one of claims 1 to 6. A step of obtaining a water phase part by mixing catechins derived from green tea, water and a polyglycerin fatty acid ester having an HLB of 14 to 16,
Mixing a polyglycerin-condensed ricinoleate and a fatty acid triglyceride having 6 to 12 carbon atoms to obtain an oil phase, and
A method for producing an oil-soluble antioxidant containing tea catechins, comprising adding 100 to 500 parts by mass of the oil phase part to 100 parts by mass of the water phase part. The water phase part is prepared by mixing 10 to 80 parts by mass of polyglycerol fatty acid ester having an HLB of 14 to 16 and 60 to 360 parts by mass of water with respect to 100 parts by mass of catechins, and the oil phase part is carbon. Prepared by mixing 25 to 34,000 parts by mass of polyglycerol condensed ricinoleic acid ester with respect to 100 parts by mass of fatty acid triglyceride having a number of 6 to 12.
The manufacturing method of the oil-soluble antioxidant of Claim 8.   The method for producing an oil-soluble antioxidant according to claim 8 or 9, wherein an extracted tocopherol derived from a natural product is further mixed in the step of obtaining an oil phase part.   The oil-soluble antioxidant according to claim 10, wherein the blending amount of the natural product-derived extracted tocopherol is 0.2 to 53,000 parts by mass with respect to 100 parts by mass of the fatty acid triglyceride having 6 to 12 carbon atoms. Manufacturing method.