JP3463308B2 - Antioxidant composition and method for producing the same - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an oil-soluble antioxidant composition capable of uniformly solubilizing catechins, whose use has been limited because they are insoluble in oils and fats, and a method for producing the same. .

[0002]

2. Description of the Related Art JP-A-63-134883 discloses a water-in-oil type lipophilic antioxidant obtained by emulsifying catechin using a lipophilic emulsifier. This antioxidant has an increased affinity for fats and oils without reducing the antioxidant power of catechin, and can be uniformly dispersed in fats and oils. However, since this lipophilic antioxidant is a water-in-oil type emulsion, it exhibits an emulsified state in fats and oils, which causes a problem that the fats and oils become cloudy.

[0003]

In order to solve the above problems, an object of the present invention is to easily solubilize catechins insoluble in fats and oils in the fats and oils without causing turbidity, and to have an excellent antioxidant effect. An oxidant composition is provided. Another object of the present invention is to propose a method for producing an antioxidant composition, which can easily and efficiently produce the above antioxidant composition.

[0004]

The present invention provides the following antioxidant composition and method for producing the same. (1) (A) catechins 1 to 40 parts by weight, (B) water or / and alcohol 1 to 40 parts by weight, (C) HLB 6 to 14 emulsifier 1 to 35 parts by weight, (D) polyglycerin condensation A composition comprising 5 to 70 parts by weight of ricinoleic acid ester and 0.5 to 30 parts by weight of (E) enzyme-decomposed lecithin, wherein the aqueous phase part contains the components (A), (B) and (C). Is an antioxidant composition in which the component (D) is dispersed in a solubilized state. (2) (A) catechins 1 to 40 parts by weight, (B) water or / and alcohol 1 to 40 parts by weight, and (C)
An aqueous phase part obtained by mixing 1 to 35 parts by weight of an emulsifier having an HLB of 6 to 14, 5 to 70 parts by weight of (D) polyglycerin condensed ricinoleic acid ester, and (E) 0.5 to 0.5 of enzymatically decomposed lecithin. A method for producing an antioxidant composition, which comprises mixing 30 parts by weight and dispersing the aqueous phase part in the component (D) in a solubilized state.

Examples of the catechins (A) used in the present invention include epicatechin, epigallocatechin, epicatechin gallate, epigallocatechin gallate and the like, and both synthetic products and natural extracts can be used. These can be used alone or in combination.

[0006] Natural extracts include non-fermented tea such as Japanese tea, semi-fermented tea such as oolong tea, fermented tea such as black tea, organic solvents such as ethanol, ethyl acetate, chloroform, hexane, water, and supercritical carbon dioxide. It is obtained by extracting with. The natural extract contains impurities such as saccharides in addition to catechins, but these impurities can be used without separation. If necessary, the solvent may be concentrated by distillation or the like, or purified by a commonly used purification method such as an HPLC method, a solvent fractionation method, or a column purification method. Further, as the natural extract, not only the one obtained by completely removing the extraction medium but also the one dissolved in the extraction medium can be used. However, in this case, it is necessary to remove the extraction medium such as ethyl acetate and chloroform, which is not preferable for food.

The content of catechins (A) in the antioxidant composition is 1 to 40 parts by weight, preferably 1 to 30 parts by weight, as catechins containing no impurities or extraction medium. When the content of catechins (A) is less than 1 part by weight, the function as an antioxidant is not sufficiently exhibited, and when it exceeds 40 parts by weight, the catechins are completely dissolved in the antioxidant composition. Therefore, a uniform antioxidant composition cannot be obtained.

As the component (B), water, alcohol, or a mixture of both is used. As the alcohol, alcohol that can be used in foods can be used, and ethanol is preferable. The content of water or / and alcohol (B) in the antioxidant composition is 1 to 40 parts by weight, preferably 5 to 35 parts by weight, which is an amount capable of completely dissolving catechins (A). When the content of water or / and alcohol (B) is less than 1 part by weight, it is difficult to completely dissolve the catechins (A), and when it exceeds 40 parts by weight, the antioxidant composition is sufficiently contained in the oil or fat. It becomes difficult to solubilize it.

As the emulsifier (C) having an HLB of 6 to 14 used in the present invention, various commercially available anionic, nonionic, cationic and amphoteric emulsifiers can be used. Especially when used for tetraglycerin monooleate, tetraglycerin monolaurate,
Preference is given to polyglycerin fatty acid esters such as hexaglycerin monooleate and hexaglycerin monolaurate, sucrose fatty acid esters and sorbitan fatty acid esters. The HLB is preferably 8 to 14.

The content of the emulsifier (C) in the antioxidant composition is 1 to 35 parts by weight, preferably 5 to 30 parts by weight.
When the content of the emulsifier (C) is less than 1 part by weight, when the antioxidant composition is dissolved in fats and oils, it becomes cloudy without being solubilized, and when it exceeds 35 parts by weight, clouding of the emulsifier when solubilized. Occurs.

The polyglycerin condensed ricinoleic acid ester (D) used in the present invention is obtained by an esterification reaction of condensed ricinoleic acid and polyglycerin mainly using castor oil as a raw material, and the degree of polymerization of polyglycerin is 2 -16, preferably 4-10, and the degree of condensation of ricinoleic acid is 2-16, preferably 2-10.

Specific examples thereof include tetraglycerin condensed ricinoleic acid ester, hexaglycerin condensed ricinoleic acid ester, and mixtures thereof. These can be used alone or in combination.

The content of the polyglycerin condensed ricinoleic acid ester (D) in the antioxidant composition is 5 to 70 parts by weight, preferably 10 to 50 parts by weight. When the content of the polyglycerin condensed ricinoleic acid ester (D) is less than 5 parts by weight, the antioxidant composition separates into two phases, and
When it exceeds 0 parts by weight, it becomes cloudy when the antioxidant composition is dissolved in fats and oils, and solubilization is difficult.

The enzymatically decomposed lecithin (E) used in the present invention
Is lecithin hydrolyzed with a hydrolase,
For example, various products such as natural lecithin decomposed with a hydrolase or fractionated product thereof can be used. Even if lecithin that is not enzymatically decomposed is used, the antioxidant composition targeted by the present invention cannot be obtained.

The content of enzymatically decomposed lecithin (E) in the antioxidant composition is 0.5 to 30 parts by weight, preferably 5 to 30 parts by weight.
Parts by weight. The content of enzymatically decomposed lecithin (E) is 0.
When the amount is less than 5 parts by weight, the antioxidant composition is not solubilized in oils and fats and remains as a water-in-emulsifier emulsifier, and the oils and fats dissolved therein become cloudy. Further, when it exceeds 30 parts by weight, the stability of the antioxidant composition is deteriorated such that the antioxidant composition is separated into two phases over time, and the antioxidant is added in the oil and fat to which the antioxidant composition is added. The composition may precipitate over time.

In the antioxidant composition of the present invention,
It is presumed that the emulsifier as the component (C) plays a role of increasing the compatibility between the catechins (A) and the polyglycerin condensed ricinoleic acid ester (D). It is also presumed that the polyglycerin condensed ricinoleic acid ester (D) plays a role of uniformly dispersing the catechins (A) in the oil and fat. Further, the enzymatically decomposed lecithin (E) reduces the surface activity of the water-in-emulsion emulsifier of the polyglycerin-condensed ricinoleic acid ester (D) and the catechins (A), and plays a role of forming a uniform solubilized product. Presumed.

Next, a method for producing the antioxidant composition of the present invention will be described. The antioxidant composition of the present invention comprises a polyglycerin condensation product and an aqueous phase obtained by mixing catechins (A), water or / and alcohol (B) and an emulsifier (C) having an HLB of 6 to 14. Produced by mixing ricinoleic acid ester (D) and enzymatically-decomposed lecithin (E) so as to have the above-mentioned content, and dispersing the solution forming the aqueous phase part in the component (D) in a solubilized state. it can.

In the production method of the present invention, it is important to mix and dissolve the components (A), (B) and (C), and the components (D) and (E) are added simultaneously with these three components. The composition intended by the present invention cannot be obtained even if a solution is prepared by mixing or a composition is prepared by mixing any one of the three components with the components (D) and (E). .

The water phase portion is preferably mixed with the component (D) to form a water-in-emulsifier type emulsion, and then the component (E) is added to solubilize the water phase portion and the component (E). After mixing
The component (D) may be mixed. Further, the water phase part, the component (D) and the component (E) can be mixed at the same time.

As a preferred manufacturing method, there is the following method. First, catechins (A) completely dissolved with water or / and ethanol (B) are mixed with an emulsifier (C) having an HLB of 6 to 14 and dissolved. Next, this mixed solution is used as an aqueous phase part, and polyglycerin condensed ricinoleic acid ester (D) is added to this to emulsify to form a water-in-emulsifier emulsion. The enzyme-decomposed lecithin (E) is added to this emulsion and sufficiently mixed to solubilize the emulsion to obtain the antioxidant composition of the present invention. Upon preparation, it may be heated, if necessary, or diluted with an oil or the like to reduce the viscosity.

In the case of the above production method, when the component (D) is added to the aqueous phase portion and emulsified, the catechins (A), water or / and alcohol (B) and HLB are 6 to 6.
An aqueous emulsifier-in-water emulsion in which the aqueous phase portion containing 14 emulsifiers (C) was included in the inner phase by the polyglycerin condensed ricinoleic acid ester (D) and the outer phase became the polyglycerin condensed ricinoleic acid ester (D). That is, a water-in-water emulsion of polyglycerin condensed ricinoleic acid ester is formed. By adding the enzyme-decomposed lecithin (E) to the emulsion, the surface activity of the emulsion is reduced and the emulsion is in a solubilized state, and a one-phase homogeneous composition is obtained.

The antioxidant composition thus obtained can be used as an antioxidant as it is or after diluted with oil or fat, added to the oil or fat. There is no limitation on the concentration to be added to the oil or fat, and it may be appropriately selected depending on the purpose of use and the effect, and for example, the concentration may be 0.0001 to 99% by weight. When added to oils and fats, the antioxidant composition of the present invention is transparently dissolved and does not become cloudy. In addition, no separation occurs even after long-term storage. Furthermore, the excellent antioxidant effect of catechins is exhibited.

[0023]

As described above, in the antioxidant composition of the present invention, a solution containing a specific amount of catechins, water or / and alcohol, and an emulsifier can be used in the presence of a specific amount of enzyme-decomposed lecithin. Since it is dispersed in the amount of polyglycerin condensed ricinoleic acid ester in a solubilized state,
Catechins insoluble in fats and oils can be easily solubilized in fats and oils without causing turbidity, and have an excellent antioxidant effect of catechins.

According to the production method of the present invention, the above antioxidant composition can be produced simply and efficiently.

[0025]

EXAMPLES The present invention will now be described in detail with reference to examples, but the present invention is not limited to these examples.

Example 1 10 g of theafuran 30A (trade name, containing tea extract manufactured by ITO EN Co., Ltd., containing 31.4% of catechins), 15 distilled water
g and 10 g of tetraglycerin monolaurate (SY Glister ML310, trade name, HLB = 10.3, manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.) are thoroughly stirred with a propeller mixer, heated to 50 ° C. while mixing, and completely dissolved. did. Add polyglycerin condensed ricinoleate (SY
35 g of Glister CR-ED (trade name, manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.) was added and sufficiently stirred and mixed to give a water-in-emulsifier emulsifier. 10 g of enzymatically decomposed lecithin (Elmizer A, trade name, manufactured by Kyowa Hakko Kogyo Co., Ltd.) was added to this water-in-emulsion emulsifier, and mixed again while heating to 50 ° C. to obtain 80 g of an antioxidant composition. It was

Tuna oil (manufactured by NOF CORPORATION, DHA =
24.7%, EPA = 7.1%, POV = 0) 100 g
To the above, 0.2 g of the above antioxidant composition was added and mixed. 5 g of this oil was collected in a 25 ml sample bottle,
Cover and leave in a constant temperature bath at 25 ° C for a certain period of time, then POV
Was measured according to the standard oil and fat analysis test method. The results are shown in Fig. 1.

EXAMPLE 2 0.2 g of the antioxidant composition obtained in Example 1 and 0.2 g of tocopherol (E oil 800, trade name, manufactured by Riken Vitamin Co., Ltd.) were added to the same tuna oil as in Example 1. 10
Added to 0 g. The POV of this oil was measured in the same manner as in Example 1. The results are shown in Fig. 1.

Comparative Example 1 The POV when tuna oil was used alone without adding an antioxidant to the same tuna oil as in Example 1 was measured in the same manner as in Example 1. The results are shown in Fig. 1.

COMPARATIVE EXAMPLE 2 To 100 g of tuna oil similar to that of Example 1 was added 0.2 g of only tocopherol (E oil 800 described above), and the POV of this oil was measured in the same manner as in Example 1. The results are shown in Fig. 1.

As shown in FIG. 1, it is understood that the fats and oils of the examples do not increase in POV even if they are allowed to stand for a certain period of time, and that the antioxidant composition of the present invention has excellent antioxidant properties.

Example 3 10 g of Theafuran 70A (trade name, containing tea extract manufactured by ITO EN Co., Ltd., containing 79.6% of catechins), 20 distilled water
g, and tetraglycerin monolaurate (said SY
10 g of Glister ML310) was sufficiently stirred with a propeller mixer and heated to 50 ° C. while being mixed to completely dissolve it. To this solution, 40 g of polyglycerin condensed ricinoleate (SY GLISTAR CR-ED) was added and sufficiently stirred and mixed to obtain a water-in-emulsifier emulsion. 10 g of enzymatically decomposed lecithin (the above-mentioned Elmizer A) was added to this water-in-emulsifier emulsifier and mixed with heating to obtain 90 g of an antioxidant composition.

0.1 g of this antioxidant composition was added to corn oil 9
When added to 9.9 g and mixed and dissolved, it was transparently dissolved and stored at 30 ° C. for 15 days, but no precipitation or separation occurred, and it was suitable as an antioxidant.

Comparative Example 3 An antioxidant composition was prepared in the same manner as in Example 3 except that the enzyme-decomposed lecithin was not used. 0.1 g of this antioxidant composition
Was added to 99.9 g of corn oil and mixed. The fats and oils to which this antioxidant composition was added were cloudy and did not dissolve transparently. When this oil was stored at 30 ° C. for 10 days, a precipitate was generated and it was unsuitable as an antioxidant.

Examples 4 to 7 Antioxidant compositions were prepared according to the formulations shown in Table 1, and lard (Tocopherol [E Oil 400, manufactured by NOF CORPORATION) was used.
(Product name, manufactured by Riken Vitamin Co., Ltd.) 0.02% already added)
0.2% by weight was added, and its antioxidant property was measured based on the AOM test method (standard oil and fat analysis method 2.4.28.81-81). The results are shown in Table 2.

Comparative Example 4 The antioxidant properties of the lard used without adding an antioxidant to the lards used in Examples 4 to 7 were measured in the same manner as in Examples 4 to 7. The results are shown in Table 2.

Comparative Examples 5 to 9 Antioxidant compositions having the formulations shown in Table 1 were prepared, and Examples 4 to
0.2% by weight was added to lard as in Example 7, and its antioxidant property was measured in the same manner as in Examples 4 to 7. The results are shown in Table 2.

[0038]

[Table 1]

[0039]

[Table 2]

From Table 2, it can be seen that the antioxidant composition of the present invention is transparently solubilized in fats and oils and has an excellent antioxidant effect.

[Brief description of drawings]

FIG. 1 is a graph showing the results of Examples 1 and 2 and Comparative Examples 1 and 2.

Front page continued (72) Inventor Chuichi Takeo 21 Sagami-cho, Haibara-gun, Shizuoka Prefecture Itoen Central Research Institute (72) Inventor Toshio Kawasaki 21 Sagara-machi, Shizuoka Prefecture Itoen Central Research In-house (56) References JP 63-135483 (JP, A) JP 63-197528 (JP, A) (58) Fields investigated (Int.Cl. ⁷ , DB name) C09K 15/00-15 / 34 C11B 5/00 A23L 1/00-1/035

Claims (2)

(57) [Claims] 1. (A) 1 to 40 parts by weight of catechins, (B) 1 to 40 parts by weight of water or / and alcohol, (C) 1 to 35 parts by weight of an emulsifier having HLB of 6 to 14, (D) poly Glycerin condensed ricinoleic acid ester 5-5
70 parts by weight and (E) 0.5 to 30 parts by weight of enzymatically decomposed lecithin, wherein the aqueous phase part containing the components (A), (B) and (C) is ) An antioxidant composition characterized in that it is dispersed in a component in a solubilized state. 2. Mixing 1 to 40 parts by weight of (A) catechins, 1 to 40 parts by weight of (B) water or / and alcohol, and 1 to 35 parts by weight of an emulsifier having (C) HLB of 6 to 14 The resulting aqueous phase part and (D) polyglycerin condensed ricinoleic acid ester 5 to
70 parts by weight and (E) 0.5 to 30 parts by weight of enzymatically decomposed lecithin are mixed, and the aqueous phase part is dispersed in the component (D) in a solubilized state, and an antioxidant composition. Method of manufacturing things.