JP2002012785A - Yellow dye and dye preparation - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a yellow dye which is excellent in heat resistance and acid resistance, and to provide a drink or a food product using the yellow dye. SOLUTION: The yellow dye is extracted from one or more selected from madder (Rubia tinctorum) root, a tissue-culture cell of madder and a cultured capillary root of madder with water or a water-containing alcohol and thereafter is subjected to purification treatment so as to adjust the content of a ruberythric acid and/ or lucidin-3-primeveroside to 70% or more. The drink and the food product use the yellow dye.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention relates to a method for producing a novel composition comprising a ruberic acid and / or lucidin-3-primeveroside having a content of 70%.
% Of a yellow pigment, for example, a radish root having a high content of rubertophosphate and / or lucidin-3-primeveroside, a tissue culture cell material of the madder root and a hairy root culture. From the above, after extraction with water or water-containing alcohol, the content of the purified rubertophosphoric acid and / or lucidin-3-primeveroside is 70% or more, and the alizarin content is 10% or less. The present invention relates to a yellow pigment, a pigment preparation using the same, and food and drink.

[0002]

2. Description of the Related Art In recent years, demand for natural pigments as food pigments has been increasing. Methods for coloring food in yellow are well known in the art. For example, there is a method using carotenoid pigments such as annatto pigment, gardenia yellow pigment, carrot carotene, dunariella carotene, palm oil carotene, marigold pigment, safflower yellow pigment, red malt yellow pigment, turmeric pigment and the like.

[0003] However, these conventionally used pigments have serious drawbacks when used for coloring foods.

[0004] For example, when carotenoids such as carrot carotene, Dunaliella carotene, palm oil carotene and marigold pigments which are oil-soluble pigments are used in foods and the like which require water-soluble or water-dispersible pigments, these are used. Must be formulated into a water-dispersible emulsified pigment, but when this emulsified pigment is used in foods, turbidity is inevitably produced, and transparent coloring is impossible. In addition, these dyes also have a problem in stability, and in order to use them stably, it was necessary to use an antioxidant such as vitamin C in combination.

Further, among water-soluble dyes, annatto dyes,
Gardenia yellow spot, red yeast yellow spot, turmeric pigment, stability,
In particular, there is a problem with light resistance, and the addition of an antioxidant such as vitamin C, which has been conventionally used, does not sufficiently improve the stability of the pigment.

On the other hand, safflower yellow is relatively stable in light resistance and is widely used for coloring foods. However,
Safflower yellow pigment cannot be used in foods to which antioxidants such as vitamin C are added, because light resistance is extremely deteriorated. In recent years, foods that use antioxidants and foods that contain a large amount of vitamin C for the purpose of nutritional enhancement have been sold.
Natural pigments capable of coloring them stably and vividly in yellow have been desired.

Further, regarding yellow pigments, Japanese Patent Publication No. 59-5
No. 0706 and Japanese Patent Publication No. 59-50263 describe a method for producing a yellow pigment which does not cause greening using an extract of a gardenia fruit, and Japanese Patent Application Laid-Open No. 02-249490 discloses a method of culturing a microorganism belonging to the genus Monascus to produce a yellow pigment. A method for producing a water-soluble yellow pigment to be obtained, JP-A-04-153271, discloses a stabilized yellow pigment for condensing a carbohydrate with a hydroxyl group of a glycoside of a carotenoid pigment, and JP-A-05-032909 discloses a safflower yellow pigment. Discoloration inhibitors, JP-A-06-093199, and Gardenia yellow pigment discoloration inhibitors, JP-A-06-248193
Japanese Patent Application Laid-Open No. Hei 10-155190 discloses a method for producing a yellow pigment which comprises culturing a plant belonging to the genus Lactuca containing crocetin obtained by hydrolyzing crocin and collecting a yellow pigment from the resulting culture. 306224 describes a method for producing a safflower yellow pigment having high transparency by removing a browning component. However, these methods have not been sufficient to solve the above problems. Another example of a dye excellent in light fastness and heat resistance is madder dye. Although this dye was yellowish, it was a dark reddish yellow, and it was not possible to color clear yellow with this dye.

As described above, there has been no conventional yellow pigment capable of coloring food and drink in a stable and clear yellow color and having excellent heat and light resistance.

[0009]

SUMMARY OF THE INVENTION An object of the present invention is to provide a yellow pigment which can be colored in a vivid yellow color and has excellent heat and light resistance, a pigment preparation using the yellow pigment, and food and drink. I do.

[0010]

Means for Solving the Problems The present inventor has made extensive studies in view of the above-mentioned problems, and as a result, it has been found that the content of rubertophosphoric acid and / or lucidin-3-primeveroside is 70% or more. Yellow pigment characterized by, for example,
Purification is performed after extraction with at least one of water or hydroalcohol from at least one of the roots of western radish, the tissue culture cells of western rape, and the hairy root culture, which have a high content of rubert phosphate and / or lucidin-3-primeveroside. Thereby, the content of the ruberic acid and / or lucidin-3-primeveroside is 70% or more, and further, the alizarin content is 10%.
By adjusting the following, it was found that a yellow pigment excellent in heat resistance and light resistance can be obtained, and by using this pigment, foods and drinks are colored in a clear yellow color excellent in heat resistance and light resistance. This led to the present invention.

The western madder of the present invention is a dicotyledonous plant of the genus Rubiaceae, which is a perennial plant widely distributed from temperate to tropical. It is well known that the dye contained is extracted with hot water and dyed in combination with a mordant.

When a liquid obtained by extracting ordinary madder with water or hydrous alcohol is used for food, its color tone can be colored only to dark reddish yellow. Since it contains a large amount of red pigment alizarin and the like in addition to the yellow pigment components such as rubertophosphoric acid and / or lucidin-3-primeveroside contained in western madder, it is difficult to obtain a bright yellow color tone. That's why. Further, according to the analysis of the inventor, the content of the rubert phosphate and / or lucidin-3-primeveroside in such an extract was such that it accounted for about 60% of the total pigment component contained.

According to the present invention, the western radish root, which is a raw material having a high content of the yellow component of ruber phosphate and / or lucidin-3-primeveroside, and the tissue culture cell culture and hairy root culture of the western radish are described. After selection, the liquid obtained by extraction from the western madder is filtered, co-precipitated or centrifuged to remove solids as necessary, and then directly or concentrated, and the adsorption resin, ion-exchange resin, function The polymer content of Rubert phosphoric acid is 70
% Or less, preferably 80% or more, alizarin 10% or less, preferably 5% or less by adjusting the yellow pigment,
It was possible to obtain a yellow pigment excellent in heat resistance and light resistance, which was not present in the past.

The adsorption treatment can be carried out according to a conventional method, for example, an adsorption treatment with silica gel or a porous ceramic; a styrene-based duolite S-861 (trade name: Duo)
lite, USA manufactured by Diamond Shamrock Co., Ltd., the same applies hereinafter), Duolite S-862, Duolite S-863 or Duolite S-866; aromatic Sepabeads SP70 (trademark, manufactured by Mitsubishi Chemical Corporation, hereinafter the same) ), Sepabeads SP700, Sepabeads SP825; Diaion HP10 (trademark, manufactured by Mitsubishi Chemical Corporation, the same applies hereinafter), Diaion HP20, Diaion HP21, Diaion HP40, and Diaion HP5
0; or Amberlite XAD-4 (trademark, manufactured by Organo,
The same applies hereinafter), Amberlite XAD-7, Amberlite XAD
Adsorption treatment using a synthetic adsorption resin such as -2000.

Also, the ion exchange treatment is not particularly limited, and a cation exchange treatment or an anion exchange treatment can be performed using a conventional resin according to a conventional method. For example, the cation exchange resin is not limited, but is Diaion SK 1B
(Trademark, manufactured by Mitsubishi Chemical Corporation, the same applies hereinafter), Diaion SK 102, Diaion SK 116, Diaion PK2
08, Diaion WK10, Diaion WK20, etc.
The anion exchange resin is not limited, but is Diaion SA 10A (trademark, manufactured by Mitsubishi Chemical Corporation, the same applies hereinafter).
, DIAION SA 12A, DIAION SA 20A, DIAION PA 306, DIAION WA10, DIAION WA20, and the like.

The functional polymer membrane in the present invention includes, for example, a membrane filter (MF) membrane, an ultrafiltration (UF) membrane, a reverse osmosis membrane and an electrodialysis membrane. Regarding the membrane material of such a functional polymer membrane, whether natural, synthetic or semi-synthetic, for example, cellulose, cellulose di-
-Or tri-acetate, polyamide, polysulfone, polystyrene, polyimide, polyacrylonitrile and the like.

Specifically, NTU-3150 film, NTU-3250 film, NTU
-3550 membrane, NTU-3800 UF membrane (Nitto Denko); Cefilt
-UF (manufactured by NGK); AHP-2013 membrane, AHP-3013 membrane, AHP-1
010 film (all made by Asahi Kasei), NTR-7250 film, NTR-7410 film, N
TR-7430 film, NTR-7450 film (Nitto Denko), AIP-301
3 film, ACP-3013 film, ACP-2013 film, AIP-2013 film, AIO-1010
A film such as a film (all manufactured by Asahi Kasei) can be used.

In the present invention, the supercritical gas extraction includes a method in which a liquid such as carbon dioxide, ethylene, propane, etc. is brought into contact with a red pigment extract in a closed system at a temperature and pressure higher than the critical point. .

Even if the above-mentioned various treatments are performed alone,
Further, two or more kinds may be arbitrarily combined, and the same processing may be repeatedly performed under the same or different conditions.

If necessary, the yellow pigment of the present invention can be diluted with a solvent such as alcohol, propylene glycol or glycerin and used as a preparation, or can be used as a powder with excipients such as dextrin or lactose. It is.

It is also possible to prepare a mixed dye preparation by mixing with other dyes. For example, when used in combination with a gardenia blue pigment, a spirulina blue pigment, and Food Blue No. 1, an excellent green mixed pigment preparation can be obtained.

When preparing the above-mentioned pigment preparation or mixed pigment preparation, and / or adding it to food or drink, an antioxidant can be used in combination for the purpose of further stabilizing the pigment. .

The antioxidant used in the present invention is not particularly limited, and examples thereof include those widely used as food additives, such as ascorbic acids such as L-ascorbic acid and salts thereof; erythorbic acid and Erythorbic acids such as salts thereof, sodium sulfite and pyrosulfite; tocopherols such as α-tocopherol and mixed tocopherol; dibutylhydroxytoluene (BH
T) and butylhydroxyanisole (BHA); ascorbic esters such as ascorbic acid palmitate; mallow flower extract, licorice oil extract, edible canna extract, clove extract, apple extract, essential oil-extracted fennel extract Stuff, horseradish extract, sage extract, seri extract, tea extract, dokudami extract, green coffee bean extract, sunflower seed extract, pimenta extract, grape seed extract, blueberry leaf extract, hego・
Ginkgo extract, pepper extract, balsam extract, bayberry extract, eucalyptus leaf extract, gentian root extract,
Extracts of various plants such as rutin extract (red soybean whole plant, enju, buckwheat whole plant extract) and rosemary extract; others, enzyme-treated rutin, rutin hydrolyzate (quercetin), enzyme-treated isoquercitrin, rapeseed oil Extract, rice bran oil extract, rice bran enzyme decomposed product, and the like, and preferably plant extracts such as bayberry extract, rutin extract, green coffee bean extract, and rosemary extract; enzyme-treated rutin; Enzyme-treated isoquercitrin and the like can be mentioned.

The proportion of the antioxidant to be added to the yellow pigment is as follows:
The ratio is not particularly limited as long as it enhances the fading prevention effect of the yellow dye, and can be appropriately selected and adjusted. Usually, with respect to the yellow pigment, the antioxidant is usually 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, more preferably 0.1 to 100 parts by weight.
It can be blended at a ratio of 10 parts by weight.

The present invention provides a yellow pigment excellent in heat resistance and light resistance, thereby providing colored foods, drinks, cosmetics, pharmaceuticals, quasi-drugs, and feeds.

As cosmetics, skin lotions,
Lipstick, sunscreen cosmetics, make-up cosmetics, etc., various tablets, capsules, drinks, lozenges, gargles, etc. as pharmaceuticals, dentifrices as quasi-drugs,
Examples include, but are not limited to, a mouth freshener, a bad breath preventing agent, and the like, and examples of the feed include various pet foods such as cat food and dog food, and ornamental fish or cultured fish.

[0027] Food and drink are preferred. Foods and drinks are not particularly limited as long as they have coloring, that is, those having a color. For example, frozen desserts such as sherbet and frozen desserts; drinks such as soft drinks containing fruit juice, carbonated drinks, fruit juice drinks, powdered drinks; jelly and yogurt, etc. Gums such as chewing gum and balloon gum (plate gum, sugar-coated granulated gum); chocolates such as chocolate having a flavor such as coated chocolate, strawberry chocolate, blueberry chocolate and melon chocolate; hard candy (bonbon, Caramels such as butterball, marble, etc., soft candies (including gummy candies, etc.), drops, toffee, etc .; shallow pickles, soy sauce pickles, salt pickles, miso pickles, cake pickles, koji pickles, bran pickles, pickled pickles, pickled pickles, Moromizuke, Umezuke, Fukujinzuke, Shibazuke, Gingerzuke, Chosenzuke Pickles such as plum pickled; separate dressing,
Non-oil dressings, sauces such as ketchup, sauce, sauces; jams such as strawberry jam, blueberry jam, marmalade, apple jam, apricot jam, preserves; fruit wine such as red wine; cherry, apricot, apple, strawberry pickled in syrup And various processed foods of the fruit for processing.

[0028]

EXAMPLES Hereinafter, the contents of the present invention will be specifically described with reference to the following experimental examples, examples, and comparative examples. However, the present invention is not limited to these. The units of the formulations described below are g unless otherwise specified, and% means% by weight.

[0029]

Example 1 Hot water 15 g was added to 100 g of dried western madder root.
After adding 00 ml and washing well, the mixture was extracted with 40% (V / V) hydroalcohol at 80 ° C. for 3 hours and filtered to obtain a western madder extract.

Next, the thus obtained western radish extract was applied to an adsorption resin (Tiyaion HP-21 (Mitsubishi Kasei Kogyo Co., Ltd.)
50% after adsorbing to 500 ml and washing the resin well
(V / V) The dye was eluted with 500 ml of alcoholic water to obtain a yellow dye A containing 83.3% rubertophosphoric acid in the total dye component.

[0031] Color tone with pH = 3 buffer using madder extract and madder yellow essence product

[Table 1] The color tone is obtained by calculating tristimulus values of a Hunter color system (Lab system) with a V-560 UV-visible spectrophotometer manufactured by JASCO, and converting lightness (L), saturation (Chroma), and hue (Hue) into transmitted light. Measured. The lightness (L) is brighter as the value is larger, and the hue (Hue) is (yellow orange) 0Y-5Y-10.
Y (= 0 GY) -5.0 GY (bright yellow) is shown, the larger the value of GY, the clearer the color, and the smaller the value of Y, the more orange. The chroma (Chroma) indicates that the larger the value, the more vivid.

As shown in Table 1, the yellow pigment A has a significantly clearer and brighter yellow color tone than the madder extract.

[0033]

[Experimental Example 1] Heat resistance and light fastness tests were performed using the yellow dye A (the present invention) and other yellow natural dyes (each Saneigen FFI Co., Ltd.) under the following conditions. . (Dyes used) 1 Yellow dye A (the present invention) 2 Safflower yellow dye 3. Gardenia yellow dye 4. Marigold dye 5. β-carotene 6. Turmeric dye 7. Red malt yellow dye (Light fastness test) Irradiation tester: Xenon long life fade meter XWL-75R (manufactured by Suga Test Machine) Integrated irradiation irradiance: 100, 200 Lngley (300)
(Heat resistance test) Storage temperature: 55 ° C Time: 1 to 2 weeks (Test results) (a) Light resistance test results Dye residual ratio (%), no vitamin C added

[Table 2] (B) Results of heat resistance test Dye residual rate (%), no vitamin C added

[Table 3] (C) Effect of vitamin C

[Table 4] Integrated illuminance: 100 Langley

[0034]

[Experimental example 2] Beverage containing lemon juice Formulation 1. Fructose glucose liquid sugar 1,250 (g) 3. citric acid 20 3.1 / 5 concentrated lemon juice 220 Lemon flavor 10 5. Yellow dye A 2.0 6. The total volume is adjusted to 10 liters with vitamin C 5.0 water.

A lemon juice solution was prepared according to the above-mentioned formula, subjected to instant sterilization at 93 ° C. in a plate sterilizer, filled and cooled.
A soft drink containing lemon juice was prepared. The prepared soft drink showed a very clear yellow color, and even after storage at 40 ° C. for 3 months, almost no fading of the pigment was observed.

[0036]

[Experimental example 3] Lemon candy prescription 1. Sugar 600 (g) 2. 2. Candy syrup (75%) 400 Water 200 4. Citric acid 1.5 5.1 / 5 Lemon concentrated juice 20 6. Lemon flavor 2.0 2.0 7. Yellow dye A 1.0 Make up to 10 liters with water.

The above formulas 1, 2 and 3 were boiled down to 150 ° C., allowed to cool to 120 ° C., added with 4 to 7, mixed and molded to prepare lemon candy. This lemon candy showed a clear yellow color, and kept a clear yellow color even after storage at room temperature for 6 months.

[0038]

Experimental Example 4 A green pigment preparation was prepared by mixing 50 parts of yellow pigment A and 20 parts of gardenia blue pigment (manufactured by San-Ei Gen FFI Co., Ltd.), and the following green pigment preparation was used. Melon jelly was adjusted by prescription and manufacturing method.

Melon Jelly Formulation 1. Water 28 (g) 2. Pectin 1.3 3. Sugar 50 4. Citric acid 0.45. Syrup 50 Green pigment preparation 0.05 7. Melon spice 0.18. Enzyme-treated isoquercitrin 0.05 (Sammeline AO-1007, San-Ei Gen FFI Co., Ltd.)

After mixing 2, 3, and 5 with 1 and stirring and dissolving at 80 ° C. for 10 minutes, 4, 6, 7, and 8 are added, mixed, filled into a container, sterilized at 85 ° C. for 30 minutes, and meloned. The jelly was adjusted.

The prepared jelly exhibited a very clear yellow-green color, and no fading of the dye was observed even after storage at room temperature for 3 months.

[0042]

EFFECTS OF THE INVENTION The yellow pigment component of western madder, western madder root, which is a raw material having a high content of rubertophosphate, and a tissue culture cell and hairy root culture of western madder are selected, and the pigment extracted from the western madder is purified. And a content of rubertophosphoric acid and / or lucidin-3-primeveroside 7
By adjusting the amount to 0% or more, a clear yellow pigment is obtained, and by using this yellow pigment, food or drink can be colored in a clear yellow color having excellent heat and light resistance.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C09B 67/54 A23G 3/00 101 // A23G 3/00 101 A23L 1/06 A23L 1/06 2/02 B 2/02 2/00 MF term (reference) 4B014 GB06 GG07 GG09 GK05 GL03 4B017 LC01 LE10 LG02 LG04 LG15 LK08 LK11 LL01 LL07 LP01 LP12 LP14 LP15 4B018 LB01 LB08 MA07 MB05 MF01 4B041 LC02 LD02 LE08 LH05 A17 AB01 AC02 AD10C FA01

Claims (7)

[Claims] 1. The method of claim 1, wherein said is ruberic acid and / or lucidin-3-.
A yellow pigment having a content of primeveroside of 70% or more. 2. The method according to claim 1, wherein the yellow pigment is obtained by extracting from at least one of a western radish root, a cell culture cell culture of the western radish and a hairy root culture with water or a hydrous alcohol, and then performing a purification treatment. The yellow pigment according to claim 1, 3. The yellow pigment according to claim 2, wherein the alizarin content is 10% or less. 4. A pigment preparation comprising the yellow pigment according to claim 1. 5. The pigment preparation according to claim 4, further comprising an antioxidant. 6. A food or drink comprising the pigment preparation according to claim 4. 7. A food or drink containing an antioxidant and the yellow pigment according to claim 1.