JP2000270807A - Fading preventing agent for anthocyanin-based coloring matter and food containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain both a fading preventing agent capable of significantly suppressing a fading phenomenon of an anthocyanin-based coloring matter and an anthocyanin-containing food in which the fading is significantly suppressed. SOLUTION: The characteristic of this fading preventing agent is to contain isochlorogenic acid or its salt as an active ingredient. The isochlorogenic acid is at least any one kind selected from the group consisting of 3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid and 3,4,5-tricaffeoylquinic acid.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an anti-fading agent for an anthocyanin dye and a food containing an anthocyanin dye containing the anti-fading agent. The present invention also relates to a new use of isochlorogenic acid.

[0002]

2. Description of the Related Art Anthocyanin dyes are widely used in the fields of foods, cosmetics, pharmaceuticals, and the like as water-soluble natural dyes that impart a red to purple-red color tone.

[0003] However, anthocyanin dyes are
It is unstable to oxygen, light and heat, and has the disadvantage that it rapidly discolors or discolors during processing or storage of foods due to these factors and other influences such as additives.

[0004] For this reason, various stabilizers and anti-fading agents have been studied and developed in order to eliminate the instability of the anthocyanin dyes and prevent the fading phenomenon.

[0005] For example, JP-A-58-65761 describes that chlorogenic acid and / or caffeic acid have an effect of preventing discoloration of anthocyanin-based dyes.

[0006]

However, the present inventors have confirmed that the effect of chlorogenic acid and / or caffeic acid on the fading of anthocyanin-based dyes is not sufficiently satisfactory. In fact, it was not possible to sufficiently prevent the discoloration of the hair.

An object of the present invention is to provide an anti-fading agent which can significantly suppress the fading phenomenon of anthocyanin dyes. A further object of the present invention is to provide an anti-fading agent having a significantly higher anti-fading effect of an anthocyanin dye than chlorogenic acid.

Another object of the present invention is to provide an anthocyanin-containing food in which the discoloration phenomenon is significantly suppressed by containing such a discoloration inhibitor.

[0009]

Means for Solving the Problems The inventors of the present invention have made intensive studies to achieve the above object, and found that dicaffeoylquinic acid (isochlorogenic acid) is excellent in fading anthocyanin-based dyes. Chlorogenic acid, which is significantly higher than the known chlorogenic acid. Furthermore, the present inventors have found that the isochlorogenic acid is particularly effective in preventing the fading phenomenon due to the heat treatment, and the effect is significantly higher than that of chlorogenic acid. The present invention has been developed based on such knowledge.

[0010] That is, the present invention is an anti-fading agent for anthocyanin-based dyes, comprising isochlorogenic acid or a salt thereof as an active ingredient. Further, the present invention is an anthocyanin-based dye-containing food, comprising the above-mentioned anti-fading agent for anthocyanin-based dyes.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The anti-fading agent for anthocyanin dyes of the present invention is characterized by containing isochlorogenic acid as an active ingredient. The isochlorogenic acid includes 3,5-dicaffeoylquinic acid represented by the formula (1), 3,4-dicaffeoylquinic acid represented by the formula (2), and 4,4 represented by the formula (3). Three isomers of 5-dicaffeoylquinic acid and 3,4,5 represented by the formula (4)
-Contains tricaffeoylquinic acid.

[0012]

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In the present invention, these can be used alone or as a combination of two or more as required.

As the salt of isochlorogenic acid, there may be mentioned water-soluble salts such as alkali metal salts such as sodium salt and potassium salt.

The isochlorogenic acid used may be a chemically synthesized product or a product obtained from a natural source. Isochlorogenic acid is generally widely present in plants such as sweet potato, tobacco leaf, pear leaf, apple pulp, etc., considering the content ratio, from the roots, stems, leaves, etc. of sweet potato. Easy to collect. The type of sweet potato is not particularly limited, but in addition to Beni Satsuma, Kokei No. 14, Beniazuma, Beniotome, Koganesengan, Satsumahikari, Satsumahikari, Benihayato, etc., purple sweet potato native to Ayamurasaki, Brazil
a batas, Lam .. Convolvlaceae), purple purple sweet potatoes such as purple Yamakawa, native to Tanegashima, purple purple, Chiran purple, Kiire purple and Nakamurasaki, and improved varieties thereof.

For example, when sweet potato is used as a starting material, isochlorogenic acid can be obtained, for example, from the method described in Japanese Society for Food Science and Technology, Vol. 43, No. 3, pp. 313-317 (1996). Specifically, first, the potato root, stem, leaves, etc. of the sweet potato are subjected to a heat treatment such as steaming, then dried, pulverized, extracted with a water-containing aqueous ethanol solution, and the obtained extract is optionally used. After concentration, the concentrated extract may be subjected to various column chromatography such as gel filtration and ion exchange to separate and purify isochlorogenic acid.

The isochlorogenic acid or a salt thereof used in the present invention does not necessarily have to be a pure product, but does not affect the taste or aroma of an object to which a discoloration inhibitor is applied, for example, cosmetics, foods or pharmaceuticals. Those that have been purified to a certain extent are preferred.

The anti-fading agent of the present invention may be composed of only isochlorogenic acid as long as it contains isochlorogenic acid or a salt thereof as an active ingredient. It may be in the form of a composition containing other additives. Diluents, carriers and additives are not particularly limited as long as they do not hinder the effects of the present invention, and include, for example, sucrose, glucose, dextrin, acacia, water, ethanol, propylene glycol, glycerin, starch syrup, and the like. Can be.

The form of the anti-fading agent of the present invention is not particularly limited, and it can be prepared in any form such as powder, granule, tablet, liquid, emulsion, paste and the like.

The anthocyanin-based dyes targeted by the present invention are flavonoid-based water-soluble dyes exhibiting red, blue and purple colors, and specifically include, for example, purple sweet potato dyes,
Red cabbage pigment, elderberry pigment, grape juice pigment, grape skin pigment, purple corn pigment, red radish pigment, perilla pigment, red rice pigment, cowberry pigment,
Gooseberry pigment, cranberry pigment, salmonberry pigment, sim blueberry pigment, strawberry pigment, dark sweet cherry pigment, cherry pigment, hibiscus pigment, huckleberry pigment, black currant pigment,
Blackberry pigment, blueberry pigment, plum pigment,
Examples include Whittleberry dye, Boysenberry dye, Mulberry dye, Purple potato dye, Raspberry dye, Red currant dye, Loganberry dye, and other anthocyanin dyes. These dyes may be used alone or in any combination of two or more.

The above-mentioned dyes may contain other dyes as long as the effect of the present invention is not impaired.

Examples of such dyes include quinone dyes such as cochineal dye, sicon dye, madder dye, and lac dye; flavonoid dyes such as oyster dye, carob dye, licorice dye, rosewood dye, sugar dye, and safflower yellow dye. Azaphilone pigments such as Beni-kouji pigment and Beni-ko-ji red pigment; carotenoid pigments such as carotenes and xanthophylls and other pigments such as safflower yellow pigment, turmeric pigment, sagi pigment, gardenia blue pigment, garden yellow pigment, gardenia red pigment, spirulina Suitable examples include natural dyes such as blue dyes and synthetic dyes such as tar dyes. In addition, although there is no restriction, as the tar dye,
For example, Food Red No. 2, Food Red No. 3, Food Red 40
No., Food Red No. 102, Food Red No. 104, Food Red No. 1
No. 05, Food Red No. 106, Food Yellow No. 4, Food Yellow No. 5
No. 1, Food Blue No. 1, Food Blue No. 2, Food Green No. 3, and the like. In contrast to the combined use of such a dye and an anthocyanin-based dye, the anti-fading agent of the present invention can exhibit not only the anthocyanin-based dye but also the anti-fading effect.

The anti-fading agent of the present invention can be widely applied to, for example, those containing the above-mentioned anthocyanin dyes. Such substances include, for example, foods, cosmetics, pharmaceuticals, quasi-drugs, feeds, and the like.

That is, the present invention provides an anthocyanin pigment-containing food, cosmetic, pharmaceutical, quasi-drug and feed containing isochlorogenic acid or a salt thereof as an anti-fading agent. As cosmetics, skin lotions, lipsticks, sunscreen cosmetics, make-up cosmetics, etc., as pharmaceuticals, various tablets, capsules, drinks, troches, gargles, etc., and as quasi-drugs, dentifrices, Examples include, but are not limited to, fresheners, bad breath preventives, etc., and examples of feed include various pet foods such as cat food and dog food, and ornamental fish or cultured fish.

Preferably, it is a food. Examples of food include, but are not limited to, ice cream, ice milk,
Frozen desserts such as lacto ice, sherbet, frozen desserts, etc .; drinks such as milk drinks, lactic acid bacteria drinks, soft drinks containing fruit juice, carbonated drinks, juice drinks, powdered drinks, etc .; pudding, jelly, bavarois,
Desserts such as yogurt; gums such as chewing gum and balloon gum (plate gum, sugar-coated granular gum); hard candy (including bonbon, butterball, marble, etc.);
Soft candy (including caramel, nougat, gummy candy, marshmallow, etc.), caramels such as drop and toffee; pickles such as shallow pickles, salted pickles, bran pickles, pickled plums etc .; separate dressings, non-oil dressings, ketchup, sauces, sauces etc. Sauces; jams such as strawberry jam, blueberry jam, and marmalade; fruit wines such as red wine; and various processed foods such as various side dishes and kamaboko, fu, and rice fu.

Among them, weakly acidic to acidic foods are preferred. Specifically, pH 5 or less, preferably pH
It is a food having a pH of 4 or less, more preferably a pH of 3.5 or less.

In the production process of these foods, the compounding step of the anti-fading agent and the anthocyanin dye of the present invention and the order thereof are not particularly limited, but the anthocyanin dye, preferably an anthocyanin dye, is added in the presence of the anti-fading agent. In addition, it is desirable to mix fragrances and fragrances and to perform various treatments such as heat treatment.

For example, in the case of frozen desserts, milk dessert, cream, condensed milk, powdered milk, sugar, fruit, bean paste, etc. are added to the main ingredients, such as anti-fading agents, acids, emulsifiers and stabilizers, and then flavors are added. A method of preparing a liquid, adding and mixing an anthocyanin-based dye to the mixed liquid, then sterilizing and filling a container, cooling and freezing to prepare a final product can be mentioned. In the case of beverages, sugars, fruit juices, acids, etc. as main ingredients are added with an anti-fading agent, a stabilizer, and the like, and then a flavor and an anthocyanin pigment are added to the beverage, mixed, sterilized, cooled, and placed in a container. The method of filling can be mentioned. In the case of gums, sugar, glucose, an anti-fading agent, citric acid and the like are added to a heated and softened gum base, and then a fragrance and an anthocyanin pigment are added and kneaded. Next, a method of preparing a final product by adjusting the thickness to an appropriate value with a rolling roller, cooling to room temperature, and cutting the product can be given. In the case of jellies, the main ingredients sugar, starch syrup, anti-fading agent, citric acid and a coagulant (pectin, agar, gelatin, carrageenan, etc.) are mixed in an appropriate ratio, and the fragrance and anthocyanin-based pigment are contained therein. Then, after heating and dissolving, a method of filling in a container and cooling to prepare jelly as a final product can be mentioned. In the case of candies, for example, sugar, syrup, and the like, water is added to the main raw material, heated and dissolved, then left to cool, a discoloration inhibitor is added, and then a fragrance and an anthocyanin dye are added,
Molding and cooling to room temperature to prepare the final candy can be mentioned. In the case of pickles, vegetables, salt, sugar, sodium glutamate are used as the main raw materials, seasonings and anti-fading agents are added thereto to prepare pickles, and after adding flavor and anthocyanin pigment to the pickles, A method of filling a container, sterilizing and cooling to prepare a final product can be mentioned. In the case of dressings, vegetable oil, soy sauce, juice, sugar, juice, brewed vinegar, salt, etc. are the main raw materials, and an anti-fading agent, a stabilizer, an emulsifier, etc. are added thereto,
After adding and mixing a fragrance and an anthocyanin-based dye to the dressing solution, sterilizing and cooling, and then filling the container to prepare a final product.

The amount of the anti-fading agent of the present invention to be added to objects such as foods, cosmetics, pharmaceuticals, quasi-drugs, and feeds is not particularly limited as long as the amount of the anthocyanin dye contained therein can be prevented from fading. It is not limited, and can be appropriately selected and determined in consideration of the type of the object, the components contained therein, the content of the anthocyanin-based dye, and the like. For example, when the object is a food, the amount of the anti-fading agent to be added to the food may be in the range of 10 to 500 ppm in terms of isochlorogenic acid. The ratio of the anti-fading agent to the dye contained in the object is determined by the ratio of the amount of isochlorogenic acid to the absorbance (Abs) at the maximum absorption wavelength of the dye.
A ratio at which the ratio of absorbance at 5 nm is 1 or more can be given.

[0030]

EXAMPLES Hereinafter, the present invention will be described in detail with reference to the following examples and comparative examples, but the present invention is not limited to these examples. The unit of the prescription described below means g unless otherwise specified. Example 1 Shaved ice syrup liquid sugar 65 sugar 3 citric acid 0.25 carrageenan 0.3 salt 0.15 elderberry pigment 0.2 isochlorogenic acid 0.005 (3,4-dicaffeoylquinic acid) water Total 100.000 The above formulation was added and mixed to prepare a shaved ice syrup solution.

Experimental Example 1 A shaved ice syrup solution (comparative product 1) in which chlorogenic acid was added in place of isochlorogenic acid in the same manner as in Example 1 above to give an almost identical absorbance at the maximum absorption at 325 nm (comparative product 1), and shaved ice without both additives A syrup solution (comparative product 2) was prepared in the same manner as in Example 1.

Using the shaved ice syrup solution of Example 1 and a comparative product thereof, as a first experiment, these drinks were used in an amount of 20.
The “lightfastness” of the shaved ice syrup was tested by being left at 5 ° C. for 5 days under irradiation of 000 lux fluorescent light. As a second experiment, the "heat resistance" was tested by leaving these shaved ice syrups in a 50 ° C. thermostat for 14 days. The chromaticity of the syrup at the start was 100% (control), and the degree of fading was compared with the naked eye. Table 1 shows the results.

[0033]

[Table 1]

As is clear from Table 1, the shaved ice syrup solution of the present invention prepared by adding isochlorogenic acid showed significantly less discoloration after light irradiation and after heat treatment than Comparative Product 1 containing chlorogenic acid. It was suppressed and a clear red color was maintained.

Example 2 Acerola drink fructose dextrose liquid sugar 7.0 sugar 5.0 citric acid 0.4 1/5 acerola juice 4.4 acerolaph flavor 0.2 red cabbage dye 0.2 isochlorogenic acid 0.005 ( 3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid mixture and 4,5-dicaffeoylquinic acid mixture) water q.s. total 100.000 fructose-glucose and sugar sugars, citric acid, Acerola juice was used as a main raw material, to which isochlorogenic acid and acerola flavor were added, and then red cabbage pigment was added thereto, mixed and filled into a container to prepare an acerola beverage.

Experimental Example 2 An acerola drink (comparative product 3) in which chlorogenic acid was added in place of isochlorogenic acid in Example 2 to give almost the same absorbance at the maximum absorption at 325 nm (Comparative Product 3), and an acerola drink without both additives (Comparative product 4) was prepared in the same manner as in Example 2.

Using the acerola beverages of Example 2 and their comparative products, 1000
Leave for 3 days at 5 ° C under illumination of 0lux fluorescent light,
The "lightfastness" of the acerola beverage was tested. As a second experiment, these beverages were left in a thermostat at 50 ° C. for 7 days to test “heat resistance”. The degree of fading was visually compared with the chromaticity of the beverage at the start as 100% (control). Table 2 shows the results.

[0038]

[Table 2]

As is evident from Table 2, the acerola beverage of the present invention prepared by adding isochlorogenic acid, as in Experimental Example 1, had a greater effect than Comparative Product 3 containing chlorogenic acid.
Discoloration was significantly suppressed after light irradiation and after the heat treatment, and a clear red color was maintained. Although the fading phenomenon was suppressed at a high rate with respect to light, the fading phenomenon due to the heat treatment was almost completely suppressed. Anthocyanin dyes are known to be unstable to heat and light, especially in the presence of ascorbic acid. However, from this experiment, isochlorogenic acid imparts heat resistance and light resistance to anthocyanin dyes (particularly heat resistance). It has been found to significantly contribute to
Its effect was significantly higher than chlorogenic acid.

Example 3 Fruit Jelly (Peach Jelly) Fructose Glucose Liquid Sugar (75%) 20.0 1/5 Concentrated White Peach Juice 4.0 Carrageenan 1.0 Citric Acid 0.2 Peach Essence 0.1 Red Cabbage Dye 0.1 isochlorogenic acid 0.004 (3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid and 3,4,5-tricaffeoylquinic acid the mixture) water q.s. total 100.000 the above composition of acid added and mixed, dissolved by heating 80 ° C. 10 minutes, filled into cups, and cooled 5 ° C. 1 hour to make a fruit jelly.

Example 4 Strawberry Sorbet Sugar 15.0 Powdered Cane Sugar 7.5 Hardened Coconut Oil 1.0 Skim Milk Powder 1.0 1/5 Concentrated Strawberry Juice 4.0 Strawberry Flavor 0.1 Grape Juice Pigment 0.22 Isochlorogen acid 0.007 (3,4-mixture of dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid) water q.s. total 100.000 skim milk, sugar, powdered starch syrup, a fruit juice as a main raw material, which Then, isochlorogenic acid, hydrogenated coconut oil, and flavor were added to a mixed solution, and a grape juice pigment was added to the mixed solution and mixed. Thereafter, the container was sterilized, cooled and frozen, filled in a container, cooled to 0 ° C. or lower, and frozen to produce a strawberry sorbet.

Example 5 Acerola Gum Gum Base 100 Purified Glucose 288.95 Powdered Sugar 100 Citric Acid 0.5 Acerola Flavor 5.0 Red Radish Dye 1.0 Isochlorogenic Acid 0.05 (3,5-dicaffeoylquinic acid) and 4,5-cafe mixtures oil quinic acid) mixing components other than red radish pigment of water q.s. total 500.00 the above formulation was softened by heating, added red radish pigment, kneading Then, the mixture was adjusted to an appropriate thickness with a rolling roller, cooled to room temperature, and cut to produce acerola gum.

Example 6 Hard candy A mixture of 20 g of water, 60 g of sugar and 40 g of starch syrup was heated at 150 ° C.
And heat to 100 g
Cool until grape skin pigment 0.1 g, citric acid 0.5
g, acerola flavor and 0.15 g of isochlorogenic acid (4,5-dicaffeoylquinic acid) were added, and after molding, the mixture was cooled to room temperature to prepare a hard candy.

Example 7 Bonito-flavored plum Plum vinegar 42.0 Sugar 4.0 Fructose-glucose liquid sugar 20.0 Citric acid 1.0 Sodium glutamate 0.5 Bonito extract 1.0 Purple corn pigment 0.3 Isochlorogenic acid 0 .006 (3,5 mixture of dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid) plum 50.0 was added mixing water qs total 150.00 the above formulation, prepared plum bonito flavor did.

Example 8 Plum Dressing Brewed Vinegar 5.0 Sugar 3.0 Salt 2.6 Soy Sauce 5.0 Apple Cider Vinegar 5.0 Lemon Juice 3.0 Sodium Glutamate 0.5 Kombu Extract 1.0 Bonito Extract 1.0 plum 3.0 Shisooiru 0.05 malic acid 0.4 perilla pigment 0.2 isochlorogenic acid 0.008 (3,5-dicaffeoylquinic acid) corn salad oil 40.0 water qs total 100.000 above After adding and mixing the components, sterilization and cooling were performed, followed by filling in a container to prepare a plum dressing.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI theme coat ゛ (Reference) A23L 1/22 A23L 1/22 D 1/24 1/24 A 2/58 2/02 A 2/02 2 / 00 M (72) Inventor Mitsumi Kawamoto 1-1-11 Miwa-cho, Toyonaka-shi, Osaka F-term (reference) 4F014 GB06 GB18 GB21 GG05 GK05 GL04 GY02 4B017 LC01 LG01 LK08 LL09 4B018 LB01 LB03 LB08 LB09 MA02 MB02 MC04 MD10 MF01 MF06 4B035 LC16 LE02 LE03 LE04 LG04 LG32 LP21 LP22 4B047 LB02 LB09 LE01 LG06 LG08 LG39 LP01

Claims (3)

[Claims] 1. An anti-fading agent for an anthocyanin dye, comprising isochlorogenic acid or a salt thereof as an active ingredient. 2. The method of claim 1, wherein the isochlorogenic acid is 3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, and 3,4,5-tricaffeoylquinic acid. The anti-fading agent for an anthocyanin dye according to claim 1, which is at least one selected from the group consisting of: 3. An anthocyanin pigment-containing food, comprising the anti-fading agent for anthocyanin pigment according to claim 1 or 2.