JP5968714B2 - Oil-soluble pigment preparation for food - Google Patents

Description

  The present invention relates to an oil-soluble dye preparation for food.

  2. Description of the Related Art Conventionally, water-based foods such as beverages, pickled seasonings, and fish paste products have been colored using oil-soluble pigments such as paprika pigments. As oil-soluble dye preparations suitable for coloring aqueous foods, for example, oil-in-water emulsion preparations or solubilized preparations containing oil-soluble dyes are known (Patent Documents 1 and 2).

  However, since a special emulsification facility or the like is required for producing the emulsion liquid preparation or the solubilized liquid preparation, it is indispensable to input a large amount of energy. Further, when an oil-soluble dye is emulsified or solubilized, there is also a problem that the original color tone is likely to change. For example, in the case of paprika dye, there is a tendency to change from red to orange to red-orange.

  On the other hand, as an oil-soluble dye preparation of a type different from either the emulsion liquid preparation or the solubilized liquid preparation, the oil-soluble dye for food contains 1% or more and 90% or less of one or more unsaturated fatty acid esters of polyglycerin. There has been proposed a food coloring composition characterized in that (Patent Document 3). A preparation of this type can be produced without an emulsification facility and the like, and can be colored in an aqueous food because it is dispersed in water, and it is favorable with little change from the original color tone of the pigment.

  However, when such a preparation is added to an aqueous food and colored using a stirrer or the like, the dispersibility of the pigment to the food differs depending on the stirring force (stirring speed), and the color tone of the food to be colored is different (hereinafter referred to as “colored food”). And the problem of color stability due to stirring). For example, in the case of a paprika pigment preparation, red orange food tends to be reddish when the stirring power is strong, and red food tends to be red when the stirring power is weak.

  Moreover, when a foodstuff is produced by adding this type of pigment preparation, there is a problem that the pigment adheres to a production apparatus such as a tank or a stirrer, which makes the washing difficult. Although the problem has been improved to some extent in the food coloring composition of Patent Document 3, further improvement is desired.

JP-A-10-120933 JP 2006-109792 A JP-A-8-238071

  An object of the present invention is a pigment preparation that imparts water-dispersibility to an oil-soluble pigment by incorporating an emulsifier in the oil-soluble pigment, and the pigment that adheres to the problem of color stability due to stirring and a food production apparatus, etc. It is an object to provide a food-grade oil-soluble pigment preparation with improved detergency.

As a result of intensive research in order to solve the above problems, the present inventors have found not only esters of polyglycerin having an average polymerization degree of 2 to 4 and unsaturated fatty acids, but also medium-chain fatty acid triglycerides and glycerin acetic acid fatty acid esters as oils. The present invention has been completed by finding that the above-mentioned problems can be solved by incorporating it in a soluble dye.
That is, the present invention comprises the following (1) and (2).
(1) (i) an oil-soluble dye, (ii) an ester of polyglycerin and an unsaturated fatty acid having an average degree of polymerization of 2 to 4, and (iii) a composition obtained by dissolving a medium-chain fatty acid triglyceride Oil-soluble pigment preparation for food.
(2) (i) oil-soluble dye, (ii) ester of polyglycerin having an average polymerization degree of 2 to 4 and unsaturated fatty acid, (iii) medium chain fatty acid triglyceride and (iv) glycerin acetic acid fatty acid ester A food-use oil-soluble pigment preparation, characterized by being a composition.

  The oil-soluble dye preparation for food of the present invention is excellent in all of water dispersibility, color tone stability by stirring, and detergency when coloring an aqueous food.

[Ingredient (i)]
The oil-soluble pigment used as component (i) in the present invention is not particularly limited as long as it is a pigment that dissolves in fats and oils and can be used in foods. For example, carotenoids and chlorophylls (chlorophyll, copper chlorophyll, etc.) Is mentioned. Examples of carotenoids include those obtained by extraction and purification from animals and plants, and those obtained by fermentation or synthesis, and any of them can be preferably used. More specifically, for example, β-carotene, α-carotene, γ-carotene, β-apo-8'-carotenal, β-apo-10'-carotenal, β-apo-8'-carotene acid, citranaxanthin , Lycopene, zeaxanthin, cryptoxanthin, echinenone, 3-hydroxy-β-carotene, fucoxanthin, lutein, astaxanthin, canthaxanthin, capsanthin, capsorubin, bixin, crocetin and esters of hydroxyl group or carboxyl group-containing compounds of these groups, etc. Is mentioned. Examples of natural carotenoids containing the above carotenoids include annatto pigment, imo carotene, shrimp pigment, krill pigment, orange pigment, crab pigment, Dunaliella carotene, red pepper pigment (also known as paprika pigment), corn pigment, tomato pigment, carrot carotene , Palm oil carotene, Phaffia pigment, Beninoki powder, Hematococcus alga pigment, Marigold pigment and the like. The oil-soluble dye may be used alone or in any combination of two or more.

[Ingredient (ii)]
An ester of polyglycerin having an average polymerization degree of 2 to 4 and an unsaturated fatty acid used as component (ii) in the present invention is an esterification product of polyglycerin having an average polymerization degree of 2 to 4 and an unsaturated fatty acid, It is produced by a per se known esterification reaction or the like.

  As polyglycerol having an average polymerization degree of 2 to 4 as a raw material for producing component (ii), a small amount of acid or alkali is usually added to glycerol as a catalyst, and in any inert gas atmosphere such as nitrogen or carbon dioxide. For example, a mixture of polyglycerols having different degrees of polymerization obtained by heating at a temperature of about 180 ° C. or higher and causing a polycondensation reaction can be mentioned. Polyglycerin may be obtained using glycidol or epichlorohydrin as a raw material. After completion of the reaction, treatments such as neutralization, desalting, and decolorization may be performed as desired. Examples of the polyglycerin include those having an average degree of polymerization of 2 to 4, such as diglycerin (average degree of polymerization 2), triglycerin (average degree of polymerization 3), and tetraglycerin (average degree of polymerization 4).

  In the present invention, high-purity polyglycerin obtained by purifying the polyglycerin using a method known per se, such as distillation or column chromatography, and increasing the concentration of a single component is preferably used. Examples of such include high-purity diglycerin having a diglycerin content of about 50% or more, preferably about 80% or more.

  Examples of the unsaturated fatty acid used as a raw material for the production of component (ii) include palmitooleic acid, oleic acid, elaidic acid, linoleic acid, γ-linolenic acid, α-linolenic acid, arachidonic acid, ricinoleic acid, Examples thereof include condensed ricinoleic acid, and preferably a mixture of one or two or more fatty acids selected from the group of oleic acid, linoleic acid and α-linolenic acid. In particular, it is preferable to use a fatty acid mixture containing about 50% by mass or more, more preferably about 70% by mass or more of oleic acid.

  In the present invention, preferred examples of component (ii) include diglycerin fatty acid esters containing about 70% or more of monoesters. The outline of the production method is as follows. For example, in a normal reaction vessel equipped with a stirrer, a heating jacket, a baffle plate, etc., diglycerin and unsaturated fatty acid in a molar ratio of about 1: 0.8 to 1: 1.2, preferably about 1: 1. Then, sodium hydroxide is added as a catalyst and mixed with stirring. Under a nitrogen gas atmosphere, the water generated by the esterification reaction is removed from the system and heated at a predetermined temperature. The reaction temperature is usually in the range of about 180 to 260 ° C, preferably in the range of about 200 to 250 ° C. The reaction pressure is under reduced pressure or normal pressure, and the reaction time is about 0.5 to 15 hours, preferably about 1 to 3 hours. The end point of the reaction is usually determined by measuring the acid value of the reaction mixture and using an acid value of about 12 or less. The obtained reaction liquid is a mixture containing unreacted fatty acid, unreacted diglycerin, diglycerin monofatty acid ester, diglycerin difatty acid ester, diglycerin trifatty acid ester or diglycerin tetrafatty acid ester. After completion of the reaction, the obtained reaction solution is cooled to about 120 ° C. or higher and lower than 180 ° C., preferably about 130 to 150 ° C., and the catalyst is neutralized by adding an acid, preferably left for about 15 minutes to 1 hour, When unreacted diglycerol is separated into the lower layer, it can be removed to obtain a diglycerol fatty acid ester.

  Furthermore, the diglycerin fatty acid ester is molecularly distilled using, for example, a falling film molecular distillation apparatus or a centrifugal molecular distillation apparatus, or purified using a method known per se such as column chromatography or liquid-liquid extraction. Thus, a diglycerin fatty acid ester containing about 70% or more of a monoester body can be obtained.

  Examples of the ester of polyglycerin having an average polymerization degree of 2 to 4 and an unsaturated fatty acid include diglycerin unsaturated fatty acid ester (product name: Poem DO-100V; 70% by mass of polyglycerin having an average polymerization degree of 2 and oleic acid. Esters with fatty acid mixtures contained above; manufactured by Riken Vitamin Co., Ltd.) are commercially produced and sold, and can be used in the present invention.

[Ingredient (iii)]
The medium chain fatty acid triglyceride (hereinafter also abbreviated as MCT) used as component (iii) in the present invention is a single or two kinds of fatty acids having 6 to 12 carbon atoms such as caproic acid, caprylic acid, capric acid or lauric acid. Triglycerides composed of the above mixture and used alone or as a mixture of two or more thereof, the fatty acid is preferably a mixture of caprylic acid and capric acid and liquid at room temperature.

  Moreover, as MCT, Actor M-1 (product name; manufactured by Riken Vitamin Co., Ltd.), Actor M-2 (product name; manufactured by Riken Vitamin Co., Ltd.), Actor M-3 (product name: manufactured by Riken Vitamin Co., Ltd.), Actor M -4 (product name; manufactured by Riken Vitamin Co., Ltd.), Actor M-107FR (product name; manufactured by Riken Vitamin Co., Ltd.) and the like are commercially produced and sold, and can be used in the present invention.

[About component (iv)]
The glycerin acetic acid fatty acid ester used as component (iv) in the present invention is an esterification product of glycerin, acetic acid and fatty acid, for example, reaction of glycerin monofatty acid ester with acetic anhydride, or ester of glycerin, acetic acid and fatty acid. It can be obtained by a chemical reaction. The obtained reaction product is a mixture containing glycerin monoacetic acid monofatty acid ester, glycerin diacetate monofatty acid ester and the like. The fatty acid constituting the glycerin acetic acid fatty acid ester is not particularly limited as long as it is a saturated fatty acid derived from edible animal and vegetable oils and fats. For example, a linear saturated fatty acid having 6 to 24 carbon atoms (for example, caproic acid, caprylic acid) Capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, etc.), preferably saturated fatty acids having 10 to 14 carbon atoms. Industrially, it is preferable to use a fatty acid mixture containing about 90% by mass or more of one or two or more saturated fatty acids selected from saturated fatty acids having 10 to 14 carbon atoms.

  Moreover, as glycerol acetic acid fatty acid ester, for example, Poem G-002 (product name; manufactured by Riken Vitamin Co., Ltd.) and the like are commercially produced and sold, and can be used in the present invention.

  The oil-soluble dye preparation for food of the present invention includes, for example, the above (i) oil-soluble dye, (ii) ester of polyglycerin having an average polymerization degree of 2 to 4 and unsaturated fatty acid, (iii) medium-chain fatty acid triglyceride and ( iv) It can be produced by mixing glycerin acetic acid fatty acid ester and heating to, for example, about 60 to 90 ° C. to dissolve. In the present invention, (iv) the use of glycerin acetic acid fatty acid ester is optional, but if this is used, the problem of color tone stability by stirring and the detergency are further improved.

  The content of components (i) to (iv) in 100% by mass of the oil-soluble pigment preparation for food of the present invention is not particularly limited. For example, (i) the oil-soluble pigment is usually about 10 to 60% by mass, preferably Is about 20 to 50% by mass, and (ii) an ester of polyglycerin having an average degree of polymerization of 2 to 4 and an unsaturated fatty acid is usually about 5 to 40% by mass, preferably about 10 to 30% by mass, iii) medium chain fatty acid triglyceride is usually about 5-60 mass%, preferably about 10-50 mass%, and (iv) glycerin acetic acid fatty acid ester is usually about 1-40 mass%, preferably about 5-30 mass%. It is.

  Moreover, in the said manufacture of the oil-soluble pigment preparation for foodstuffs of this invention, you may mix | blend edible fats and oils for the purpose of adjusting the viscosity of the preparation or adjusting the contents of components (i) to (iv). The edible fats and oils are animal and vegetable fats and oils suitable for edible use, transesterified oils, fractionated oils, etc., and it is preferable to add edible fats and oils that are liquid at room temperature (15 to 25 ° C.). Examples of such edible oils and fats include safflower oil, soybean oil, cottonseed oil, rice oil, rapeseed oil, olive oil and the like, as well as glycerin fatty acid diester and propylene glycol difatty acid ester. These edible fats and oils may be used alone or in any combination of two or more.

  In the oil-soluble pigment preparation for food of the present invention, as an optional component, for example, an antioxidant (for example, extracted tocopherol, ascorbyl palmitate, etc.) within a range not inhibiting the purpose and effect of the present invention. Etc. may be added.

  Although there is no particular limitation on the use target of the oil-soluble pigment preparation for food of the present invention, the preparation can color an aqueous food and has improved the problem of color stability due to stirring. It can be preferably used for the production of an aqueous food that can be colored in the kneading process. Examples of such water-based foods include beverages, desserts such as pudding, jelly, and yogurt, seasonings such as jams, soups, pickles, dressings, and sauces, and fish paste products such as fish sausage and kamaboko. Can be mentioned.

  There is no restriction | limiting in particular in the method of coloring a foodstuff using the oil-soluble pigment preparation for foodstuffs of this invention, It can implement by a itself well-known method. The amount of the oil-soluble dye preparation for food added to food varies depending on the kind of the dye, the color value of the preparation, the kind of food, etc., but is preferably about 0.01 to 5.0 mass with respect to 100 mass% of the food. %, More preferably about 0.02 to 3.0% by mass.

  Hereinafter, the present invention will be described more specifically based on examples, but the present invention is not limited thereto.

[Preparation of paprika dye preparation]
(1) Raw materials 1) Paprika pigment (Product name: Riquet color paprika AP-300; manufactured by Riken Vitamin Co., Ltd.)
2) Diglycerin unsaturated fatty acid ester (product name: Poem DO-100V; ester of polyglycerin having an average polymerization degree of 2 and a fatty acid mixture containing 70% by mass or more of oleic acid; manufactured by Riken Vitamin Co., Ltd.)
3) Sorbitan fatty acid ester (Product name: Poem O-80V; manufactured by Riken Vitamin Co., Ltd.)
4) Glycerol citrate fatty acid ester (Product name: Poem K-37V; manufactured by Riken Vitamin Co., Ltd.)
5) Decaglycerin unsaturated fatty acid ester (Product name: Poem J-0381V; ester of polyglycerin having an average polymerization degree of 10 and unsaturated fatty acid; manufactured by Riken Vitamin Co., Ltd.)
6) Medium chain fatty acid triglyceride (Product name: Actor M-1; manufactured by Riken Vitamin Co., Ltd.)
7) Glycerin acetic acid fatty acid ester (Product name: Poem G-002; manufactured by Riken Vitamin Co., Ltd.)
8) Rapeseed salad oil (Okamura Oil Co., Ltd.)

(2) Formulation of formulation Table 1 shows the composition of paprika pigment formulations 1 to 11 prepared using the above raw materials. Among these, the preparations 1 to 5 are examples according to the present invention, and the preparations 6 to 11 are comparative examples for them.

(3) Preparation method of preparation Based on the mixing ratio of raw materials shown in Table 1, a predetermined raw material is placed in a 500 mL glass beaker, dissolved by heating to 60 ° C while stirring with a glass rod, and then cooled to room temperature. Then, paprika pigment preparations 1 to 11 were prepared. The preparation amount of each preparation was 400 g. In addition, since the decaglycerin unsaturated fatty acid ester used for the paprika pigment preparation 10 was not completely dissolved even when heated and stirred, the paprika pigment formulation 10 could not be prepared.

[Test example]
(1) Coloring of simulated seasoning liquid 800 g of an uncolored simulated seasoning liquid (simulating a seasoning liquid used for pickles such as kimchi) prepared with the formulation shown in Table 2 was placed in a 1 L glass beaker. 4 g each of paprika pigment preparations 1 to 11 (excluding paprika pigment formulation 10) were added and a blade-type stirrer (product name: Three-One Motor; model: FBL-600; manufactured by HEIDON; one stage of 38 mm diameter three-blade type stirring blades) Wearing) at a speed “weak” (rotation speed 150 rpm) for 1 hour. Moreover, it implemented similarly about speed "strong" (rotation speed 400rpm).

(2) Evaluation of water dispersibility In the evaluation of water dispersibility, when the paprika pigment preparation was added to the simulated seasoning liquid in (1) and stirred at a speed of “weak”, the time required for dispersion was measured. When uniformly dispersed within a minute, stirring was stopped and the presence or absence of separation of the paprika pigment preparation over time was observed. The results were symbolized according to the following evaluation criteria.
<Evaluation criteria>
○: Dispersed uniformly within 10 minutes. No separation was observed after the stirring was stopped.
Δ: Dispersed uniformly within 10 minutes. Separation was gradually observed after the stirring was stopped.
X: It did not disperse | distribute even if 10 minutes passed.

(3) Evaluation of color tone stability by stirring The color tone of the simulated seasoning liquid colored in (1) above is measured with a color difference meter (product name: SE2000; manufactured by Nippon Denshoku Industries Co., Ltd.), and the hue is expressed in the Munsell color system. Regarding the numerical value of “Munsell H”, the difference between the simulated seasoning liquid colored at the speed “weak” and the simulated seasoning liquid colored at the speed “strong” was symbolized according to the following evaluation criteria. The smaller this difference is, the closer the hues of both are, and the better the tone stability by stirring. In addition, when the evaluation result of the water dispersibility in the above (2) was “Δ” or “×”, the entire simulated seasoning liquid was not uniformly colored, and thus “not evaluated” was set.
<Evaluation criteria>
A: Munsell H difference <0.5
○: 0.5 ≦ Munsell H difference <1.0
Δ: 1.0 ≦ Munsell H difference <1.5
×: 1.5 ≦ Munsell H difference −: Evaluation not possible

(4) Evaluation of detergency In a 1 L glass beaker containing 700 mL of hot water at 50 ° C., the stirrer of the stirrer used in (1) was put on the stirrer and stirred for 1 minute at a speed of “weak” And washed. After washing, the amount of paprika pigment adhering to the stirring blade was symbolized according to the following evaluation criteria.
<Evaluation criteria>
◎: No adhesion is observed ○: Slight adhesion is observed △: Slight adhesion is observed ×: Almost no change from before washing

(5) Results Table 3 shows the evaluation results of the above (2) to (4).

  From the results of Table 3, the paprika pigment preparations 1 to 5 of the present invention are the comparative preparations (paprika pigment formulations 6 to 11) in any of the evaluation items of water dispersibility, color tone stability by stirring, and detergency. It is clear that it is superior.

Claims (2)

(I) an oil-soluble dye, (ii) an ester of polyglycerin having an average degree of polymerization of 2 to 4 and an unsaturated fatty acid , (iii) a medium-chain fatty acid triglyceride, and (iv) a glycerin acetic acid fatty acid ester. A food-use oil-soluble dye preparation characterized by being. (I) an oil-soluble dye, a (ii) an ester of an average polymerization degree of 2 to 4 of the polyglycerol unsaturated fatty acid, a composition obtained by dissolving the medium chain fatty acid triglyceride and (iv) glycerol acetic fatty ester (iii) A method for producing an aqueous food comprising the step of using and coloring .