JPS6045902B2 - Method for producing water-soluble curcumin complex - Google Patents

Description

BACKGROUND OF THE INVENTION Field of the Invention This invention relates to colorants for foods or the like, and more particularly, this invention relates to water-soluble curcumin-gelatin complexes and methods for their preparation.

Conventional technology Turmeric is a plant called Curcuma Longa L (CurcumaLOngaL).

It is used in foods for its coloring properties and, rarely, for its aroma. Glucumin is. "It is a compound present in turmeric, and the coloring property of turmeric is primarily due to glucumin. Dried turmeric rhizomes generally contain about 5% glucumin. Pulverized turmeric is extracted with an organic solvent. The glucmin and the fixed and volatile oils are separated from the cellulosic plant components of the rhizome to produce oleorange.

Typically, solvents such as isopropanol, ethanol, acetone, and ethylene dichloride, as well as other solvents, are used to prepare about 30% glucumin, about 30% volatile oil, about 30% fixed oil, and about A turmeric oleoresin containing 10% polysaccharide is produced. Oleoresin is used for pickles,
It is used in the food industry for coloring baked goods, poultry products, and as a seasoning for various other foods. The characteristic aroma and bitter taste of turmeric is due to the fixed oil and volatile oil portions of the powdered spice and oleoresin.

This aroma and bitter taste are sometimes undesirable in the final food product. Fixed and volatile oils are extracted from the oleoresin by extraction with organic solvents of a different type than those used in the production of oleoresin from the rhizomes, or by crystallization of glucmin from the oleoresin, typically by filtration or centrifugation. can be removed by physically separating them. The volatile oil-free product thus obtained is referred to as defatted turmeric or defatted turmeric. Glucumin is virtually insoluble in water. Since most food systems contain significant amounts of water, it is not possible to color these food systems with glucmin without using some kind of synthetic emulsifier. point 1
directed towards solving one or more problems.

In accordance with the present invention, there is provided a method for making a water-soluble glucmin product that provides a very clear yellow solution in water without the use of artificial emulsifiers.

The glucumin products of this invention are made by dissolving glucmin raw materials, typically defatted oleoresin made from turmeric and gelatin, in a solvent consisting of up to about 25% water and the balance acetic acid, preferably at an elevated temperature not exceeding about 90°C. Manufactured by The gelatin-curcumin complex is formed during mixing gelatin, glucumin raw material and solvent. In some cases, the solvent may be removed by distillation, spray drying or any other conventional means, resulting in a water-soluble dry product, which may be in the form of a powder, or may be mixed with salt, sugar, etc. They can be added to foods in the form of mixtures with soluble dispersants such as soluble dispersants. The complex contains up to about 15% glucumin by weight on a dry matter basis, and
Provides extremely transparent colored aqueous solutions without using artificial emulsifiers.

Other features and advantages of the invention will become apparent from the detailed description provided below.

DETAILED DISCLOSURE OF PREFERRED EMBODIMENTS GLUCUMIN SOURCE Glucumin from virtually any source can be used in accordance with the present invention.

Suitable lucumin sources include turmeric oleoresin, de-bittered or defatted turmeric oleoresin, or purified oleoresin. The higher the purity of the glucumin, the lower the aqueous solution of the glucumin complex, since certain oils and other substances found in turmeric oleoresin and other typical lucumin sources tend to cloud the solution. increases transparency. Gelatin as a complexing agent and choice of solvent Glucumin binds various proteins quite strongly.

However, not all protein-curcumin complexes are easily soluble in water. For example, Chitin does not dissolve in large amounts in water, and this forms a water-soluble glucmin complex that dissolves only to the extent that Chitin itself dissolves; therefore, this complex dissolves in a clear aqueous solution. I don't serve it. Gelatin, on the other hand, is a water-soluble protein and easily binds with glucmin to form a complex that is highly soluble in water. When gelatin is dissolved in water, it tends to absorb water and form a gel.

The strength of the gel is an inherent property of gelatin, and is determined by the strength of 1 gram plume (Gr'AmsblOOm). It is measured as J or 1 Bloom (BlOOm) and typically varies from about 50 Blooms for weak gels to about 350 Blooms for strong gels. Low-bloom gelatin has shorter protein chain lengths and is relatively more polar than high-bloom gelatin.

Therefore, low bloom gelatin dissolves more easily in water than higher bloom gelatin. Glucumin is relatively insoluble in water, but very soluble in acetic acid.

However, relatively low bloom strength gelatin is highly soluble in water but poorly soluble in acetic acid. High bloom gelatin is relatively well soluble in acetic acid. In accordance with this invention, it has been found that a solvent consisting of an aqueous solution of acetic acid is a mutual solvent for both low and high bloom gelatin and glucumin. As a practical fact, it has been determined that an upper limit of about 25% by weight of water in the solvent is required to achieve substantially complete dissolution of glucmin.

As shown in the examples below, if the solvent contains more than about 3 weight percent water, it must be mixed for an excessively long time in order to dissolve the glucumin. When water is present at about 3% by volume and more, the glucumin will not dissolve unless the mixing temperature is unacceptably high. According to this invention,
Upon mixing, the gelatin and glucumin raw materials are dissolved in a mutual solvent consisting of up to 25% by weight of water and the balance of acetic acid.

The complexation reaction occurs substantially simultaneously as the gelatin dissolves.

The formed complex is dissolved in an acetic acid aqueous solvent to produce a solution of the complex. Gelatin tends to form a gel when it absorbs water, so for most efficient dissolution, gelatin should be added to the solvent gradually with continued stirring. It is desirable, although not essential, to dissolve the glucmin source prior to adding gelatin, as the addition of gelatin increases the viscosity of the solution, which makes mixing relatively difficult.

Preferably, the mixing is carried out at an elevated temperature below 90'C.

9 using the preferred solvent of acetic acid and water (75%/25%)
When attempting to dissolve gelatin at temperatures above 0°C, gelatin begins to denature and lose solubility. Mixing is preferably carried out at a temperature of about 80°C using the preferred solvent system. It is also possible to carry out the mixing operation at lower temperatures, but the lower the temperature the longer the mixing time. Denaturation of gelatin is confirmed by the formation of an insoluble white precipitate.

The onset temperature of gelatin denaturation appears to depend primarily on the properties of the solvent system and less on the bloom strength of the gelatin. For example, gelatin dissolved in pure water is 100
Gelatin dissolved in a solvent of acetic acid (75% by weight) and water (25% by weight) shows a slight denaturation at temperatures above about 90°C. Therefore, the upper limit of mixing temperature in this invention is determined by the lowest denaturation temperature of gelatin in the chosen solvent system. This temperature can be easily determined experimentally. In a preferred solvent composition comprising about 75% by weight of acetic acid and about 25% by weight of water, up to about 1 part by weight of gelatin is dissolved in about 3 parts by weight of solvent.

Furthermore, it has been found that up to about 15% by weight of glucmin, based on the combined weight of gelatin and glucmin, can be complexed with gelatin. Differences in the bloom strength of gelatin have little, if any, effect on the proportion of glucmin that can be complexed with the gelatin. Of course, the ratio of glucumin to gelatin can be lowered even further if desired. Solvent Removal The curcumin-gelatin complex of this invention may be added to food products in the form of a solution in the acetic acid/water solvent used to form the complex, provided that the characteristic aroma of acetic acid is not considered detrimental to the final food product. can do.

A suitable example of using a curcumin-gelatin complex solution in water and acetic acid in diluted or undiluted form is the use in pickled products. However, in many cases it is desirable or necessary to bring the composite into a dry form, ie, to remove the solvent.

by various means including distillation, spray drying, drum drying, air drying or freeze drying, or any other conventional means.
Substantially complete solvent removal can be achieved. The dry, dried product thus obtained can then be ground and used as is, or optionally plated or mixed with a dispersing agent such as common salt or sugar.
Curcumin-gelatin complex can be used in a wide range of foods! These foods that can be introduced include gelatin desserts,
and dry foods such as cake mixes.

Alternatively, it can be used in products other than food.
The complex exhibits a strong yellow color with excellent clarity underwater! Has color. No emulsifier is required to completely dissolve the complex in water. Specific examples will now be described to illustrate the implementation of the invention, but these examples are not intended to limit the scope of the invention.

(Example) Example 1 Turmeric A as a raw material for glucmin Turmeric Production of oleoresin Turmeric oleoresin is prepared using one or more of the following solvents: acetone, ethanol, methanol, isopropanol, ethylene dichloride, or hexane. It is a mixture of aroma components and pigment components obtained from turmeric (Curcuma Longa L.) through the extraction method used.

Typically, dried turmeric rhizomes are ground to a US standard 50 mesh size and loaded into a percolator for extraction with one or more of the solvents listed above.
Next, the mixture obtained as above was filtered and F
Solvent is removed by vacuum distillation until less than 30 ppm of solvent remains as required by DA.

The glucumin content of the oleoresin thus obtained varies depending on the choice of solvent and the glucumin content of the starting material. Commercially available glucmin is usually standardized to the desired glucmin content with food grade diluents. Preparation of defatted turmeric oleoresin 200 y of turmeric oleoresin containing 37.5% by weight of glucumin was mixed with 200 d of isopropanol at 0°C and filtered in a Buchner funnel fitted with #40 Whatman Oki paper. did.

The Okinawa cake was heated to 55℃ for 4 hours in a vacuum open.
It was dried in a vacuum of 29 inches Hg to obtain defatted turmeric powder 63y containing 94% glucumin. In all of the following examples, defatted turmeric/oleoresin was used as the raw material for glucumin, but turmeric/oleoresin may be used instead as the raw material for glucumin. However, the fixed and volatile oils present in undefatted oleoresin can cause slight turbidity in aqueous solutions and impart a faint turmeric odor to foods with subtle aromas colored by glucumin complex products. be.・12 Effect of solvent composition Low-bloom gelatin is relatively more polar than high-bloom gelatin, and is therefore less soluble in pure acetic acid.

On the other hand, glucmin dissolves very well in pure t-acid, but is relatively difficult to dissolve in water. In order to determine the optimal mutual solvent composition, the following compositions of solvents were evaluated: Acetic acid/
Water (weight/weight) 80%/20% 75%/25% 70%/30% 65%/33% The evaluation method was as follows.

60y of each solvent composition A was placed in a separate 150mL beaker equipped with a magnetic stirring bar, and 80y of each solvent composition was added while stirring.
The mixture was heated to 85 mC.

B Defatted turmeric produced by the method described in Example 1B (
1 g of glucmin (94%) is dissolved in the above solvent with stirring to obtain a clear yellow solution.

ClOO bloom gelatin 20y [Davi
s) Brand RJ. Gradually add Jl) to the mixture of step (B) with stirring until all the gelatin is dissolved.

Under the above conditions, both glucumin and gelatin are 80
%/20% solvent and 75%/25% solvent.

In the 70%/30% solvent system, 1.5 hours of stirring was required for the curcumin depletion to dissolve.

This time is considered too long for practical purposes. For 67%/33% solvent systems, the temperature should be increased to 95-1
Glucumin did not dissolve unless the temperature was raised to 00'C.

This solvent system is impractical because gelatin denaturation begins in this solvent system at about 90°C, as evidenced by the formation of a white insoluble precipitate. Under the above conditions, about 1 part by weight of gelatin is mixed with about 3 parts by weight of 75%/
25% soluble in solvent.

Example 3 Preparation of curcumin-gelatin complex As shown below, 100 bloom gelatin and 75
5% to 25% in 5% increments using a %/25% solvent system
A series of glucmin containing glucmin. A gelatin complex was prepared.

A 50077 equipped with a magnetic stirring bar! A 1 round bottom flask was charged with 60ml of solvent (75% acetic acid/25% water by weight) and heated to 80-85°C with stirring.

B. One quantity of defatted turmeric oleoresin was dissolved in the heated solvent with stirring until a clear yellow solution was obtained (5-10 minutes).

1y defatted oleoresin was used for the 5% product;
Use 2y oleoresin for 0% product and 15
3y oleoresin was used for the % product, and the same was true for other concentrations.

For the 20% sample, the defatted turmeric was completely dissolved.
It was necessary to heat the solvent to 100°C for complete dissolution, and for the 25% sample it was necessary to heat it to 105°C for complete dissolution.

ClOO bloom gelatin (Davis brand RJJ) 20
y was gradually added to the above solution while continuing to stir.

The temperature was carefully maintained between 80'C and 85°C.
) The solvent was removed from each solution by vacuum distillation under 20 mbar pressure until a viscous orange solution was obtained.

Each solution was completely dried in an open E-vacuum at 29 inches Hg vacuum at 50-60° C. for approximately 3 hours.

Using a pestle and mortar, measure each product using a U.S. standard #170
The mixture was ground through a mesh sieve.

Example 4 Analysis of Glucmin Loaded in Gelatin To determine the maximum amount of glucmin that can be complexed with gelatin, each of a series of aqueous solutions of the curcumin-gelatin product prepared in Example 3 was analyzed as follows. Absorption was measured using a spectrophotometer.

Add 0.01 of the 5% to 25% curcumin-gelatin product of Example 3 to each of five 250 ml volumetric flasks.
y was added and the volume was filled with distilled water. The 20% and 25% product solutions required heating to 70°C to 80°C to completely dissolve the product.

The visible spectrum was scanned between absorption modes from B3OO nm to 600 nm.

A cell with a 1 cm optical path was used, and distilled water was used for comparison.

I got the following results. The above data indicate that the maximum usage of glucmin is at a level of about 15% since the absorption level is essentially constant above about 15▼i.

Example 5 Effect of gelatin bloom strength This test was conducted to determine whether glucum loading differed depending on gelatin bloom strength.

Four types of curcumin-gelatin complexes were prepared by adding gelatin with bloom strengths of 100, 125, 180 and 250 to the reaction mixture such that the glucumin loading was 25% with respect to the total weight of gelatin and glucumin. Prepared. Spectroscopic analysis of each final product showed that in each case only about 15% of the final product was glucumin. Example 6 Gelatin desserts are food products in which a large number of coloring agents are used and transparency is an important property.

The clarity and tinting power of a 15% curcumin-gelatin complex product prepared in accordance with this invention was evaluated in comparison to unpigmented gelatin. The glucumin content of the final gelatin dessert was 5 ppm. A colored gelatin dessert was prepared as follows. KnOx Odorless Gelatin 8y Sugar 50y 15% Curcumin-Gelatin Product 0.017y, Water
Place the 4521 gelatin, sugar, and glucumin complex in a stew pot with water and continue stirring over low heat until all the gelatin is dissolved.

The stew pot was removed from the heat and the solution was poured into a glass niveaker and cooled until solidified. 5pp
At the usage level of m, the colored gelatin has a color similar to the commercially available lemon dessert [JeIlO 9], and the clarity of the cooled gelatin is the same as that of the uncolored gelatin dessert prepared in the same way. It was hot.

Example 7 Another use of the glucmin complex product of this invention is in baked goods.

As an example, a yellow cake was made using a commercially available white cake mix and the 15% curcumin-gelatin product prepared as described above and compared to a cake made using a commercially available yellow cake mix. The cake was made as follows.

White cake mix [LOvenFresh brand manufactured by AIdiFOOds]
250y egg white 31y water
150y 15% curcumin-gelatin product 0.041y (dry basis 25p
pm) Whisk all ingredients for 4 minutes and place in a lightly oiled cake pan.

I baked the cake at 3500F for 3 batches. In a similar manner, a yellow cake was made using Lowpen Fresh's yellow cake mix (manufactured by Algi Foods) without using the glucmin complex.

The color of the yellow cake made using the curcumin-gelatin product was the same as the color of the cake prepared from the commercially available yellow cake mix.

The dry, ground curcumin-gelatin product can be mixed with a dispersing agent such as common salt or sugar to produce a substantially uniform dispersion in a dry mix such as a cake mix or powdered soft drink.

The foregoing description is for a clear understanding of the invention and is not intended to limit the invention, and those skilled in the art will be able to envision many variations within the scope of the invention.

Claims (1)

[Scope of Claims] 1. A curcumin-containing ingredient and gelatin in an amount containing up to about 15% by weight of curcumin, based on the total dry weight of curcumin and gelatin, and up to about 25% by weight of water and acetic acid. A method for producing a water-soluble curcumin-gelatin food coloring agent, which comprises dissolving the water-soluble curcumin-gelatin food coloring agent in a solvent at a temperature lower than the denaturation initiation temperature of gelatin in the solvent. 2. The method of claim 1, wherein said solvent comprises about 75% by weight acetic acid and about 25% by weight water. 3. The method according to claim 1, wherein the curcumin-containing component is defatted turmeric oleoresin, turmeric oleosin, or purified curcumin. 4. The method of claim 1, wherein said solvent comprises about 75% by weight acetic acid and about 25% by weight water, and wherein said gelatin is present at about 1 part by weight for every 3 parts by weight of said solvent. 5. Claim 4 in which the mixing is carried out at a temperature lower than about 90°C.
The method described in section. 6. The method of claim 1, comprising the additional step of substantially removing said solvent to obtain a dry colorant. 7. The method of claim 1, wherein the curcumin-containing component is dissolved in the solvent before dissolving the gelatin in the solvent. 8. A curcumin-containing ingredient selected from the group consisting of defatted turmeric oleoresin, turmeric oleoresin, and purified curcumin and gelatin in an amount containing up to about 15% by weight of curcumin based on the total dry weight of curcumin and gelatin. in a solvent comprising up to about 25% by weight of water and acetic acid at a temperature below the denaturation onset temperature of gelatin in the solvent. . 9(a) A curcumin-containing ingredient selected from the group consisting of defatted turmeric oleoresin, turmeric oleoresin, and purified curcumin is dissolved in a solvent comprising about 75% by weight acetic acid and about 25% by weight water. , and (b) step (a
) by dissolving about 1 part of gelatin to about 3 parts of the solvent used in step (a) at a temperature lower than 90°C. 1. A method of making a water-soluble curcumin-gelatin colorant comprising: producing a colorant containing % by weight of curcumin. 10. The method of claim 9, comprising the additional step of substantially removing said solvent to obtain a dry colorant. 11. A curcumin-containing ingredient and gelatin in an amount containing up to about 15% by weight of curcumin based on the total dry weight of curcumin and gelatin in a solvent comprising up to about 25% by weight of water and acetic acid. A water-soluble curcumin-gelatin colorant produced by dissolving gelatin in a solvent at a temperature lower than its denaturation onset temperature. 12. The dry water-soluble curcumin-gelatin colorant of claim 11. 13 Foods are prepared by adding up to about 25% by weight of a curcumin-containing ingredient and gelatin in an amount containing up to about 15% by weight of curcumin based on the total dry weight of curcumin and gelatin.
a water-soluble curcumin-gelatin colorant prepared by dissolving it in a solvent comprising water and acetic acid at a temperature below the denaturation onset temperature of gelatin in the solvent. How to give. 14. The method of claim 13, wherein the food is in dry form and the colorant is dispersed in a dispersant. 15. The method of claim 13, wherein said water-soluble curcumin-gelatin colorant is in dry form.