JP5094466B2 - Curcumin composition with improved water dispersibility and stability to light - Google Patents

Description

  The present invention maintains a stable dispersion state in which particles containing curcumin do not settle or float, and can be easily dispersed in foods and drinks without requiring a special dispersing device, and is uncomfortable in added foods and drinks. The present invention also relates to a curcumin composition excellent in water dispersibility that exhibits high stability to light without exhibiting a good flavor and texture, and a food and drink containing the composition.

Curcumin ((1E, 6E) -1,7-bis (4-hydroxy-3-methoxyphenyl) -1,6-heptadiene-3,5-dione, C ₂₁ H ₂₀ O ₆ : molecular weight about 368.4 g / mol) Is a natural food color extracted from rhizomes of plant turmeric and is widely used as a spice and colorant for curry and the like. In recent years, curcumin has been widely used as a health food material that is expected to have anti-inflammatory, antitumor and antioxidant effects in tablets and capsules.

  However, curcumin is only ingested in a very small amount from a normal meal, it is difficult to expect a sufficient amount of the above action, and if it is ingested with capsules etc., it is cumbersome and lacks continuity, The drinker was very limited.

  Therefore, beverages and various foods to which curcumin is added have been proposed as a method for efficiently ingesting curcumin. Addition of curcumin to foods and drinks taken daily is significant because it raises the expectation of improving its action and facilitates continuous intake of curcumin.

  However, curcumin has extremely low solubility in water and oil, and its melting point is as high as about 183 ° C., so that there are significant restrictions on its use in foods and drinks. For example, curcumin is a crystal having a high melting point, and therefore has an unbearable unpleasant texture such as graininess and graininess in the food. Moreover, when added to water-based foods and drinks, curcumin, which is a pigment, is difficult to disperse uniformly, resulting in colored spots in food. In addition, curcumin has a low solubility, and when added to liquid foods such as beverages, it becomes a precipitate and adheres to the bottom of the container, greatly impairing the commercial value. Furthermore, even if heated above the melting point, after standing to cool, it recrystallizes inside the food and the above disadvantages occur, and many foods cannot be heated in the first place. There were significant restrictions on the use of such products.

  Further, when curcumin is dissolved using a solubilizer or the like, there is a problem that the stability to light is extremely deteriorated. That is, when a beverage or the like in which curcumin is dissolved is filled in a transparent container, the curcumin content may decrease with the passage of time due to irradiation light from a store shelf or the like. For this reason, these beverages and the like have to be filled in aluminum cans or the like with high light shielding properties, and the product containers have been limited.

  Therefore, there is a strong demand for improving dispersion stability, processing characteristics, flavor, texture, and light stability so that curcumin can be used in all foods and beverages.

The following are typical prior arts in the technical fields related to the present invention.
JP 2005-185237 A JP 2000-31578 A Special Table 2000-504216 JP-A-6-9479 JP 2005-328839 A

  According to a prior art search, Patent Document 1 discloses that a curcumin can be prepared in a solution by dissolving curcumin in a polysorbate in advance and then mixing the mixed solution with an aqueous solvent. However, when curcumin is solubilized, the light resistance becomes extremely poor, and the amount of solubilizer used for solubilization also becomes large, so that the flavor and texture of the added food and drink are deteriorated. There was a disadvantage. Further, since the amount of curcumin that can be solubilized by polysorbate is extremely small, a high concentration curcumin composition could not be obtained. Furthermore, since polysorbate is not permitted to be used for food as of January 1, 2008, there is a disadvantage that the use target is limited.

  Patent Document 2 discloses a turmeric-extracted alcohol obtained by immersing a dried original wild turmeric in a skin and extracting the turmeric component. However, also in this case, the deterioration of light resistance caused by dissolution of curcumin is observed. In addition, in order to sufficiently dissolve curcumin, the alcohol content of the alcoholic beverage must be increased, and the alcohol intake of humans inevitably increases significantly, which may endanger health. . Furthermore, there is a disadvantage that curcumin cannot be taken under the condition of being unable to drink alcoholic beverages or under the circumstances where alcoholic beverages cannot be drunk.

  Patent Document 3 comprises a dispersion of a water-insoluble and / or hydrophobic natural dye in the form of an object of average size of 10 micrometers or less, wherein the object is at least one of the dyes in the absence of a surfactant. Disclosed is a formulation characterized in that it is dispersed in an aqueous phase comprising a hydrocolloid in an amount of 1% by weight and contains at least 5% by weight of water. According to this method, curcumin can be temporarily dispersed. However, particles having a size of 1 micrometer or less cannot be produced by pulverization without using a surfactant, or even if it can be produced, the particles immediately aggregate. I have. For this reason, it is difficult to stably disperse curcumin over a long period of time, and curcumin precipitates are formed due to changes over time of about 24 hours. The texture is getting worse.

  Patent Document 4 discloses a water-soluble curcumin-cyclodextrin complex characterized in that curcumin is dissolved in a mixed solvent of water and ethanol, adsorbed and included in cyclodextrin, and then ethanol is removed. A manufacturing method is disclosed. According to this method, a small part of curcumin could be stably dispersed, but it was not possible to suppress the precipitation due to the non-inclusion of curcumin.

  Patent Document 5 discloses a difficulty characterized in that it comprises means for dispersing an alcohol solution in which a hardly soluble component is dissolved in raw water and making the hardly soluble component fine particles, and means for binding the fine particles to an emulsifier. A solubilized solution of a soluble component is disclosed. According to this method, a very small amount of curcumin can be solubilized, but there is a disadvantage that a large amount of organic solvent must be used. In addition, there is a disadvantage that once solubilized curcumin settles with time.

  As described above, there has been no sufficiently satisfactory curcumin that can be added to foods and drinks, particularly water-based foods including beverages.

  The problem to be solved by the present invention is to make curcumin, which is difficult to dissolve in water, easy to disperse in water, so that it can be used in water-based foods and drinks, and can be stored for a long time. A curcumin composition having excellent water dispersibility that maintains high light stability without causing any precipitates and that does not adversely affect the texture or flavor of added foods and beverages. There is.

  As a result of diligent research for solving the above problems, the present inventors have determined the average particle diameter of particles containing curcumin (hereinafter, also referred to as “curcumin-containing particles”), thereby being excellent in water dispersibility, and The inventors have found that a curcumin composition having high stability to light can be obtained, and have completed the present invention.

  In the present invention, the curcumin-containing particles are present in a dispersed state having an average particle diameter of 210 nanometers or more and 420 nanometers or less by a laser light scattering method. When the curcumin-containing particles are not in a dispersed state but are solubilized, they lack light stability. Even in a dispersed state, if the average particle size is less than 210 nanometers, the stability is not sufficient. In addition, when the size of the curcumin-containing particles exceeds 420 nanometers, the particles are likely to precipitate over time even if dispersed.

  A first invention of the present invention is a curcumin composition containing curcumin-containing dispersed particles, an emulsifier, and an aqueous solvent, wherein the dispersed particles containing curcumin have an average particle diameter of 210 nanometers by a laser light scattering method. It is a curcumin composition characterized by being not less than meters and not more than 420 nanometers.

  The aqueous solvent as used in the present invention is a general term for water and a water-soluble solvent. Specifically, a water-based solvent, a water-soluble solvent only, a water-soluble solvent used in combination. is there. Moreover, the water-soluble solvent may use 1 type, or may use 2 or more types together.

  According to a second aspect of the present invention, in the first aspect, the emulsifier is selected from polyglycerin fatty acid ester having an HLB value of 9 or more, sucrose fatty acid ester having an HLB value of 9 or more, and modified lecithin 1 It is a curcumin composition which is a seed or a combination of two or more, wherein the aqueous solvent is one or a combination of two or more selected from water and glycerin.

  The modified lecithin is lecithin modified so that its hydrophilicity is improved. As the modified lecithin, enzymatically decomposed lecithin is preferably used.

  3rd invention of this invention is a curcumin composition whose polyglycerol fatty acid ester is a decaglycerol palmitic acid ester and / or a decaglycerol stearic acid ester in 2nd invention.

  A fourth invention of the present invention is a curcumin composition according to the first to third inventions, wherein the curcumin content is 1% by mass or more.

  According to a fifth aspect of the present invention, an emulsifier is dissolved or dispersed in an aqueous solvent, and then particles containing curcumin in the presence of the aqueous solvent in which the emulsifier is dissolved or dispersed have an average particle diameter of 210 nanometers by a laser light scattering method. It is a manufacturing method of the curcumin composition of the 1st thru / or the 4th invention characterized by grind | pulverizing so that it may become more than meter and 420 nanometer or less.

  A sixth invention of the present invention is a curcumin-containing food or drink characterized by blending any one of the curcumin compositions of the first to fourth inventions.

  According to the present invention, it is possible to stably disperse in any food including beverages without causing curcumin deposits, and the texture and flavor of the added food and drink are not impaired. In addition, the addition can be easily dispersed without using a special apparatus or a large amount of an organic solvent, and the food production process can be simplified. Furthermore, according to this invention, since the stability with respect to the light of curcumin is excellent, content of curcumin in the added food / beverage products can be maintained over a long period of time.

  Embodiments of the present invention will be described below.

  The curcumin-containing particles used in the present invention are not particularly limited as long as they can be ingested by the human body, and are not limited by the source material or the production method. For example, 1 to 5% by mass of curcumin is contained in a dried product of plant turmeric rhizome, and it can be extracted from these coarsely pulverized products. In addition, extraction with hot water, extraction with an organic solvent, and supercritical extraction are known as the extraction method, but any method can be used and is not limited to the extraction method.

  The curcumin-containing particles used in the present invention are not particularly limited in purity, and may contain curcumin in the particles, but in order to prepare a composition with a higher concentration, the content of curcumin Is preferably 70% by mass or more, more preferably 90% by mass or more.

  It is important that the curcumin-containing particles in the present invention are prepared so that the average particle diameter by the laser light scattering method is 210 nanometers or more and 420 nanometers or less. Curcumin has a maximum absorption wavelength of about 420 nanometers, and if the average particle size of the curcumin-containing particles is smaller than 210 nanometers, which is a half of this maximum absorption wavelength, the stability to light tends to deteriorate. It is. On the other hand, when the average particle size of the curcumin-containing particles exceeds 420 nanometers, a precipitate is likely to be formed over time even if dispersed. A more preferable average particle size is 210 nm or more and 300 nm or less, and it is extremely desirable to prepare particles having a particle size of 210 nm or more and 250 nm or less, particularly for improving the stability to light and dispersion. .

  Such fine particles can be prepared by any method and any pulverizer. Examples thereof include pulverization using a jet mill, a hammer mill, a ball mill, and a bead mill.

  In the present invention, for example, pulverization by a wet pulverizer is practically preferable and advantageously employed. As such a wet pulverizer, for example, a bead mill that uses beads as a pulverization medium and pulverizes curcumin-containing particles suspended in water is practical. The pulverization conditions vary depending on the raw material state of the curcumin-containing particles, the material of the beads, the size of the beads, the filling rate of the beads, the mill operation conditions, etc. The optimum conditions can be easily found while examining

  An emulsifier is used to grind curcumin to 420 nanometers or less. A suitable emulsifier is not necessarily limited, but it is preferable to use 50% by mass or more of a polyglycerin fatty acid ester having an HLB value of 9 or more in order to sufficiently wet the surface of the highly hydrophobic curcumin-containing particles and the pulverized cross section. Further, in order not to deteriorate the flavor of the composition, it is most preferable to use 50% by mass or more of decaglycerin palmitate and / or decaglycerin stearate. In addition, the HLB value in this invention is a numerical value showing the balance of hydrophilic property and lipophilicity, and can be calculated | required by a calculated value or an emulsification test.

  It is desirable to combine these with other emulsifiers or dispersants in order to enhance electrostatic repulsion and to provide higher dispersion stability. Examples of other emulsifiers or dispersants include, but are not limited to, sucrose fatty acid esters having a HLB value of 9 or more, saponins, modified lecithins, sodium hexametaphosphate, and the like. Among them, modified lecithin, particularly enzyme-decomposed lecithin is particularly preferable because it effectively enhances dispersion stability and has little influence on flavor.

  The blending amount of the emulsifier in the present invention is not particularly limited as long as the dispersibility of the curcumin-containing particles can be sufficiently maintained, but is about 1/10 to the equivalent of the blending mass of the curcumin-containing particles. This is because if the blending mass of the emulsifier is 1/10 or less of the amount of curcumin, the dispersibility of the curcumin-containing particles cannot often be sufficiently maintained, and there is no particularly advantageous effect even if blending more than an equal amount. This is because, on the contrary, the flavor deterioration caused by the emulsifier is felt.

  Water is preferred as the aqueous solvent used in the present invention. At that time, it is preferable to add a polyhydric alcohol for the purpose of adjusting the interfacial tension and assisting the dissolution of the emulsifier. Examples of the polyhydric alcohol include propylene glycol, glycerin, maltitol, reduced syrup, lactitol, palatinit, erythritol, mannitol, sorbitol and the like, and these can be added alone or in combination of two or more. Among these, glycerin is most preferable for ensuring the fluidity of the composition.

  The blending amount of the aqueous solvent is not particularly limited, but is preferably equivalent to 10 times the blending mass of the curcumin-containing particles. This is because the handling of the composition is extremely deteriorated when the amount is equal to or less, and the concentration of curcumin in the composition is decreased when the amount is 10 times or more. Since curcumin hardly dissolves in water or glycerin, these aqueous solvents can be mixed in any amount, but a considerable amount dissolves in ethanol or propylene glycol. It is preferable that the compounding quantity of a solvent shall be 20 mass% or less with respect to the whole aqueous solvent.

  The curcumin content in the curcumin composition of the present invention is not particularly limited, but the preferred content is 1% by mass or more. This is because if it is 1% by mass or less, the curcumin concentration in the composition becomes thin, it is not practical.

  The curcumin composition of the present invention can be blended with a pH adjuster, a stabilizer, a preservative and the like that can be used in foods as long as the effects of the present invention are not hindered.

  The method for producing the curcumin composition of the present invention varies depending on the production machine and the like and is not particularly limited. For example, the curcumin composition is prepared largely from two steps as shown below. First, a step of mixing an emulsifier with an aqueous solvent, and a second step of mixing and pulverizing the mixture with curcumin-containing particles.

  In the first step of the present invention, a uniform mixture is prepared by adding an emulsifier to an aqueous solvent, heating and mixing with stirring. Here, the heating temperature is not particularly problematic as long as the emulsifier is uniformly dissolved or dispersed, but when decaglycerin palmitic acid ester and / or decaglycerin stearic acid ester is used, it is heated to 70 to 90 ° C. good. The stirring method is not particularly limited, but it is preferable to use propeller stirring, a homomixer, a homogenizer, or the like in order to shorten the processing time.

  In the second step of the present invention, the curcumin-containing particles are mixed with the mixture obtained in the first step and pulverized by a pulverizer. The pulverizing conditions are not particularly limited, but it is desirable to make maximum use of the capacity of the pulverizer to be used in order to shorten the processing time. The temperature conditions for pulverization are not particularly limited, but are preferably room temperature from the viewpoint of workability and simplicity in mixing and pulverization. Since pulverization often generates heat, it is preferable to cool appropriately so that the mixture obtained in the first step does not exceed the boiling point.

  The composition of the present invention obtained as described above may be used after mixing with excipients and spray drying or freeze drying.

  In addition, the curcumin composition of the present invention can be orally ingested as a food as it is, but beverages such as fruit juice drinks, tea, coffee, milk, milk drinks, lactic acid bacteria drinks and alcoholic drinks, jelly, gummy, ice cream, Sweets such as yogurt, jam, rice cake, gum, chocolate, cookies, biscuits and cakes, sugars such as sugar and honey, chickenpox, seasonings such as soy sauce and sauce, mayonnaise and dressing, soups such as corn soup and consommé soup It can also be added to various foods such as processed foods such as hams, sausages and rice cakes, pickles and noodles, bread and rice.

  EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further more concretely, this invention is not limited only to this Example.

[Example 1]
47.55 kg of purified water, 2 kg of decaglycerin stearate (HLB value 13.5), 1.5 kg of decaglycerin palmitate (HLB value 15.0) and enzyme-decomposed lecithin (trade name: Elmizer A, Kyowa Hakko Co., Ltd.) 2 kg was added and heated to 85 ° C. to dissolve, then cooled to 30 ° C., and 25 kg glycerin, 0.1 kg potassium carbonate and 0.05 kg sodium chloride were added and dissolved. Next, 21.8 kg of curcumin crystals (purity 95%) were dispersed in this mixed solution, and pulverized by a bead mill using zirconia beads having a diameter of 0.3 mm as a medium, and water containing about 20.7% by mass of curcumin was obtained. A highly dispersible curcumin composition A was obtained. The average particle size of the curcumin-containing particles according to the laser light scattering method of this product was 220 nanometers.

[Comparative Example 1]
Curcumin composition B containing about 20.7% by mass of curcumin was obtained without pulverizing with a bead mill with the same formulation as in Example 1. The average particle size of the curcumin-containing particles by this laser light scattering method was 3600 nanometers.

[Comparative Example 2]
The grinding by the bead mill of Example 1 was performed using zirconia beads having a diameter of 2 millimeters as a medium to obtain a curcumin composition C containing about 20.7% by mass of curcumin. The average particle size of the curcumin-containing particles according to the laser light scattering method of this product was 860 nanometers.

[Comparative Example 3]
It is possible to add 789.5 g of glycerin and 10.5 g of curcumin crystals (purity 95%) to 200 g of decaglycerin oleate, solubilize by heating to 85 ° C. and stirring, and contain about 1% by mass of curcumin. A solubilized curcumin composition D was obtained.

《Light resistance test》
About the drink composition which added the curcumin composition obtained in Example 1 and Comparative Example 3, the light resistance test was implemented with the following method.

  1 g of curcumin composition A obtained in Example 1 was added to 999 g of water and mixed to obtain a beverage composition E containing 20 mg / 100 g of curcumin. The average particle size of the curcumin-containing particles by the laser light scattering method in the beverage composition E was 220 nanometers as in Example 1. Similarly, 20 g of the solubilized curcumin composition D obtained in Comparative Example 3 was added to 980 g of water and mixed to obtain a beverage composition F containing 20 mg / 100 g of curcumin. The average particle diameter of the curcumin-containing particles by the laser light scattering method in the beverage composition F was 60 nanometers. These beverage compositions were filled in a transparent glass container and sterilized at 95 ° C. for 10 minutes, and then stored in an environment at a temperature of 25 ° C. and an illuminance of 3000 LUX, and the curcumin content was measured over time.

  As a result, as shown in Table 1, the beverage composition F containing the solubilized curcumin composition D obtained in Comparative Example 3 had an accumulated illuminance of 1650 thousand (LUX · h) and only 67% of curcumin remained. On the other hand, beverage composition E blended with curcumin composition A obtained in Example 1 had 100% curcumin remaining at an integrated illuminance of 150,000 (LUX · h), and showed high stability to light.

  In Table 1, the integrated illuminance is a value obtained by multiplying the illuminance (LUX) by time (h), and the curcumin residual rate is when the curcumin content at the start, that is, when the integrated illuminance is 0 (LUX · h) is 100. The remaining rate (%).

<Dispersion stability test>
Example 1, Comparative Examples 1 to 3 Using the curcumin compositions obtained, a dispersion stability test was carried out by the following method.

  Water suspensions each containing 0.3% by mass of the curcumin composition obtained in Example 1 and Comparative Examples 1 to 3 were prepared, and the curcumin content was measured. Immediately thereafter, these were subjected to a centrifugal separation treatment under certain conditions, and the curcumin content in the suspension was measured after removing the resulting precipitate. The centrifugation treatment was performed at 2000 rpm for 10 minutes. And the precipitation rate was computed from the curcumin content measurement result before and behind the centrifugation process. As a result, as shown in Table 2, in Comparative Example 1 and Comparative Example 2, about 80% of the added curcumin was precipitated, whereas in Example 1, no curcumin precipitation was observed, and high dispersion stability was observed. It was confirmed that it had.

<< Dispersion stability and sensory test >>
Using the curcumin compositions obtained in Example 1 and Comparative Examples 1 to 3, dispersion stability and sensory tests were performed by the following methods.

  To 877 parts of water, 2.5 parts of citric acid, 0.5 part of sodium citrate and 120 parts of sugar were added and dissolved to obtain drinking water. 600 mg of the curcumin composition obtained in Example 1, Comparative Example 1 to Comparative Example 3 was added to 1 L of this drinking water in terms of curcumin, stirred and allowed to stand for 24 hours, and the dispersion state of the curcumin-containing particles was visually evaluated. . In addition, the taste and texture were evaluated by a panel of five people selected carefully. The results are shown in Table 3.

The score of flavor and texture in Table 3 is the total score of the five panels scored according to the following criteria.
<Sensory evaluation criteria>
Does not feel flavor deterioration or texture change compared to additive-free: 3 points Feels slightly flavor deterioration or texture change compared to additive-free: 2 points Significant flavor deterioration or food compared to additive-free Feel the change of feeling: 1 point

<< Additional test to food and drink >>
The curcumin composition obtained in Example 1 was added to various foods and drinks by the following method to confirm the versatility of the composition.

[Example 2]
0.3 g of curcumin composition A obtained in Example 1 was mixed with 99.7 g of commercially available milk to obtain milk containing about 61 mg / 100 g of curcumin. The milk did not show any separation of curcumin even after sterilization at 90 ° C. for 10 minutes, and could be drunk without any discomfort. In addition, this product did not change at all after storage for 30 days, and did not change the original properties.

[Example 3]
0.3 g of the curcumin composition A obtained in Example 1 was mixed with 99.7 g of the commercially available fruit juice beverage to obtain a fruit juice beverage containing about 61 mg / 100 g of curcumin. This fruit juice drink was completely free from curcumin separation even after sterilization at 90 ° C. for 10 minutes, and could be drunk without any discomfort. In addition, this product did not change at all after storage for 30 days, and did not change the original properties.

[Example 4]
0.3 g of the curcumin composition A obtained in Example 1 was mixed with 99.7 g of the commercially available soymilk drink to obtain a soymilk drink containing about 61 mg / 100 g of curcumin. This soymilk beverage was not separated from curcumin even after sterilization at 90 ° C. for 10 minutes, and could be drunk without problems. In addition, this product did not change at all after storage for 30 days, and did not change the original properties.

[Example 5]
One portion of commercially available powdered corn soup is dissolved in 149.7 g of water heated to 95 ° C. and 0.3 g of the curcumin composition obtained in Example 1 is mixed to obtain a corn soup containing about 61 mg / 150 g of curcumin. It was. No separation of curcumin was observed in this corn soup and it was possible to drink without any problems.

[Example 6]
99 g of commercially available mayonnaise was mixed with 1 g of the curcumin composition obtained in Example 1 to obtain mayonnaise containing about 207 mg / 100 g of curcumin. In this mayonnaise, no separation of curcumin was observed, and the flavor and texture could be used without any problems. In addition, this product did not change at all after storage for 30 days, and did not change the original properties.

[Example 7]
0.75 g of the curcumin composition obtained in Example 1, 95 g of sugar and 5 g of powdered gelatin were added to 249.25 g of the fruit juice and dissolved by boiling. This was poured into a container and allowed to cool and harden to obtain a jelly containing about 155 mg / 350 g of curcumin. In this jelly, there was no separation of colored spots or curcumin, and it was possible to eat without problems. In addition, this product did not change at all after storage for 30 days, and did not change the original properties.

  As described above, since the curcumin composition which is the product of the present invention can be added in an aqueous system, there is no difficulty in preparing the composition-containing food and drink, and the versatility of the composition to food and drink can be confirmed. It was.

Claims (4)

Dispersed particles containing curcumin crystals , an emulsifier, and a curcumin crystal composition containing an aqueous solvent, wherein the average particle size of the dispersed particles containing curcumin crystals is 210 nm or more and 300 nm or less by a laser light scattering method And the emulsifier is decaglycerin palmitate and / or decaglycerin stearate having an HLB value of 9 or more, and sucrose fatty acid ester, saponin, modified lecithin and sodium hexametaphosphate having an HLB value of 9 or more. A curcumin crystal composition, which is a combination of one or more selected from Curcumin crystalline composition according to claim 1, wherein the content of curcumin crystals is not less than 1 wt%. The emulsifier is dissolved or dispersed in an aqueous solvent, and then the particles containing curcumin crystals in the presence of the aqueous solvent in which the emulsifier is dissolved or dispersed have an average particle size of 210 nanometers or more and 300 nanometers or less by the laser light scattering method. The method for producing a curcumin crystal composition according to claim 1 or 2, wherein the pulverization is carried out as described above. A curcumin-containing food or drink comprising the curcumin crystal composition according to claim 1 or 2 .