Isoprenoid quinone-containing emulsion composition

Abstract

To provide an emulsion composition containing isoprenoid quinone that allows an isoprenoid quinone to be easily dispersed in water or the like, has excellent dispersion stability in the case of long-term storage, and can be used economically.SOLUTION: An emulsion composition contains (A) an isoprenoid quinone, (B) two or more polyglycerol fatty acid esters and lecithin, (C) a polyhydric alcohol, and (D) an aqueous phase component containing water.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an emulsified composition containing isoprenoid quinones, which is easily dispersible in water or the like and is economically usable. [Background technology]

[0002] Isoprenoid quinones, such as coenzyme Q10, which have a structure consisting of an isoprenoid side chain and a quinone skeleton, have high physiological activity. For example, there is a wide range of medical evidence reported on their role in preventing heart disease, high blood pressure, and arteriosclerosis. In addition, the health food market has grown in recent years, with numerous nutritional supplements being sold. A recent trend is the addition of functional health food ingredients to foods to help maintain and promote health.

[0003] However, because coenzyme Q10 is a highly crystalline, fat-soluble substance, when it is directly added to aqueous foods, especially beverages, it precipitates, resulting in poor bioavailability. For this reason, technologies have been proposed for compositions that improve the stability and absorbability of coenzyme Q10.

[0004] Patent Document 1 discloses an emulsion composition containing coenzyme Q10, phospholipids, polyglycerol fatty acid esters, and polyhydric alcohols. It is stated that this emulsion composition exhibits excellent emulsion stability even when stored at low temperatures for long periods by adjusting the blending ratio of phospholipids to coenzyme Q10 within a specified range. However, the emulsion composition described in Patent Document 1 exhibits poor emulsion stability when the coenzyme Q10 content is 20% by weight or more relative to the total emulsion composition, and does not fully address the issue of coenzyme Q10 stability. Furthermore, Patent Document 1 only describes an example of an emulsion composition containing 10% by weight of coenzyme Q10. However, at 10% by weight of coenzyme Q10 relative to the total emulsion composition, a large amount would be required to incorporate coenzyme Q10 into general foods, making it uneconomical.

[0005] Patent Document 2 discloses a water-soluble composition containing coenzyme Q10, a hydrophilic polyglycerol fatty acid ester, a lipophilic sucrose fatty acid ester, and an aqueous phase component. This coenzyme Q10-containing water-soluble composition contains a hydrophilic polyglycerol fatty acid ester, a lipophilic sucrose fatty acid ester, and coenzyme Q10, and is described as having excellent emulsion stability and high bioavailability even when stored for long periods at low to room temperatures by blending these components in a specified range. However, when the coenzyme Q10 content is 20% by weight or more relative to the total water-soluble composition, the composition takes a long time to disperse in water, resulting in a poor usability, and acid resistance and heat resistance are not taken into consideration.

[0006] Patent Document 3 discloses an emulsion composition comprising a polyglycerol fatty acid ester, a sucrose fatty acid ester, lecithin, and an organic acid monoglyceride. This emulsion composition contains a large amount of water-insoluble substances such as coenzyme Q10, and is described as having excellent alcohol resistance, heat resistance, acid resistance, and salt resistance. However, when a solution containing an acid or the like is prepared using this emulsion composition containing coenzyme Q10 and stored at room temperature for a long period of time, necking occurs, resulting in poor emulsion stability, and the emulsion cannot be maintained for a long period of time when added to general foods.

[0007] Patent Document 4 discloses a composition containing coenzyme Q10, lysolecithin, glycerin, and water. This composition contains a high concentration of coenzyme Q10, has excellent dispersibility in water, and is described as being able to be stored for a long period of time without undergoing changes such as separation or crystallization. However, because this technology differs from emulsion compositions, it takes time to disperse in water, resulting in a poor feel when used, and does not take into consideration acid resistance or heat resistance.

[0008] Patent Document 5 discloses a composition containing coenzyme Q10, a polyglycerol fatty acid ester, and glycerin. It is stated that this composition contains coenzyme Q10, has high storage stability, and is easily dispersible in water. When the coenzyme Q10 content of the entire composition is 20% by weight or more, the composition becomes highly viscous and takes a long time to disperse in water, resulting in a poor usability. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] Japanese Patent Application Laid-Open No. 2008-239580 [Patent Document 2] Re-table No. 2006-134970 [Patent Document 3] Japanese Patent Application Laid-Open No. 2008-245588 [Patent Document 4] Japanese Patent Application Laid-Open No. 2013-159556 [Patent Document 5] Patent No. 4644135 Summary of the Invention [Problem to be solved by the invention]

[0010] An object of the present invention is to provide an emulsion composition containing isoprenoid quinones, which can easily disperse isoprenoid quinones in water or the like, and which is excellent in storage stability and economical efficiency. [Means for solving the problem]

[0011] The present inventors have conducted extensive research to solve the above problems, and as a result have found that in an isoprenoid quinone-containing emulsion composition, by combining isoprenoid quinones (preferably 20 to 30% by weight), two or more types of polyglycerol fatty acid esters (preferably having an HLB of 10 to 15), lecithin, a polyhydric alcohol, and an aqueous phase component containing water, and by miniaturizing the emulsion particles, the emulsion composition is easily dispersed in water, etc., and is excellent in storage stability and economy, thereby completing the present invention.

[0012] That is, the present invention is an isoprenoid quinone-containing emulsion composition characterized by containing the following components (A), (B), (C) and (D). (A) Isoprenoid quinones (B) Two or more types of polyglycerol fatty acid ester and lecithin (C) Polyhydric alcohol (D) Aqueous phase components containing water

[0013] The polyglycerol fatty acid ester preferably has an HLB of 10 or more and 15 or less. Furthermore, the emulsion composition of the present invention preferably has an emulsion particle size of 100 nm or less.

[0014] In addition, the isoprenoid quinone-containing emulsion composition of the present invention contains 20 to 30% by weight of isoprenoid quinones, and two or more types of polyglycerol fatty acid ester and lecithin work together to emulsify the isoprenoid quinones and prevent crystallization.

[0015] Furthermore, by making the emulsified particles 100 nm or less, it is possible to easily disperse the emulsion in water, etc., and it is possible to prevent necking and precipitation even when stored for a long period of time. Furthermore, since the emulsion composition contains a high concentration of isoprenoid quinones, it only needs to be added in small amounts to foods and beverages, making it an economical emulsion composition. [Effects of the Invention]

[0016] According to the present invention, isoprenoid quinones are easily dispersed in water or the like, have excellent dispersion stability when stored for a long period of time, and can be used economically. DETAILED DESCRIPTION OF THE INVENTION

[0017] The isoprenoid quinones (A) used in the present invention are poorly water-soluble substances consisting of an isoprenoid side chain moiety and a quinone skeleton moiety, and examples thereof include ubiquinone, menaquinone, phylloquinone, and tocoquinone, with a representative component being the ubiquinone compound coenzyme Q10. There are no particular limitations on the method for producing isoprenoid quinones typified by coenzyme Q10, and those obtained by fermentation, synthesis, or extraction from plants or animals can be used.

[0018] The poorly water-soluble substance in the composition (preparation) is not limited to isoprenoid quinones, and may be combined with other types of poorly water-soluble substances, such as carotenoids, curcuminoids, and tocopherols.

[0019] The two or more polyglycerol fatty acid esters (B) used in the present invention are esters of polyglycerols having an average degree of polymerization of 5 or more and fatty acids having 8 to 22 carbon atoms. Examples of polyglycerols having an average degree of polymerization of 5 or more include hexaglycerol, octaglycerol, and decaglycerol. These can be used alone or in combination of two or more.

[0020] Examples of fatty acids having 8 to 22 carbon atoms include caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, erucic acid, etc. These may be used alone or in combination of two or more.

[0021] Preferred examples of the polyglycerol fatty acid ester used in the present invention include decaglycerol monolaurate, decaglycerol monomyristate, decaglycerol monopalmitate, decaglycerol monostearate, and decaglycerol monooleate. From the viewpoint of emulsion stability, these may be used alone, or more preferably in combination of two or more. In particular, a combination of decaglycerol monostearate and decaglycerol monopalmitate is preferred.

[0022] The polyglycerol fatty acid ester used in the present invention is not particularly limited, but from the viewpoint of emulsion stability, it can be made to have an HLB of preferably 10 or more, more preferably 12 or more. Here, HLB indicates the hydrophilic-hydrophobic balance used in the field of surfactants, and for example, the following calculation formula (Kawakami formula) can be used. HLB = 7 + 11.7 log(M W / M O ) where M W is the molecular weight of the hydrophilic group, M O is the molecular weight of the hydrophobic group. Alternatively, the HLB value listed in the catalogue may be used.

[0023] The content of the polyglycerol fatty acid ester is 1 to 30% by weight, more preferably 5 to 20% by weight, based on the total weight of the composition. If the blending amount is too small, the emulsion stability will be poor, and if the blending amount is too large, the foaming of the emulsion composition will be poor, the viscosity will increase, and the feel in use will be poor, which is undesirable.

[0024] The lecithin (B) used in the present invention has been widely used as an emulsifier in the food and cosmetics fields, and examples thereof include conventional lecithins extracted or separated from plants or animals. The source of lecithin is not particularly limited, and suitable sources include soybeans, rapeseed, and egg yolk. Other examples include enzymatically hydrolyzed lecithins, which are produced by subjecting lecithin to the action of phospholipase A2 to hydrolyze the ester bond at the β-position, thereby increasing the number of hydroxyl groups and thereby increasing the hydrophilic group. As a water-soluble emulsifier, it is preferable to use it in combination with other water-soluble emulsifiers from the viewpoint of emulsion stabilization.

[0025] The content of lecithin is 1 to 10% by weight, more preferably 1 to 5% by weight, based on the total weight of the composition. If the amount is too small, emulsion stability will be poor, and if it is too large, the flavor will be impaired, which is undesirable.

[0026] The isoprenoid quinone-containing emulsion composition of the present invention does not need to contain sucrose fatty acid esters, which are commonly used to prevent crystallization of dissolved coenzyme Q10. According to the present invention, two or more types of polyglycerol fatty acid esters and lecithin work together to emulsify isoprenoid quinones and prevent crystallization, so crystallization of isoprenoid quinones such as coenzyme Q10 can be prevented without using sucrose fatty acid esters.

[0027] The polyhydric alcohol (C) used in the present invention is not particularly limited, and examples thereof include glycerin, diglycerin, triglycerin, polyglycerin, etc. Glycerin is particularly preferred because it stably maintains fine emulsion particles. The content of the polyhydric alcohol is 30 to 70% by weight, more preferably 40 to 50% by weight, of the total weight of the composition.

[0028] The aqueous phase component (D) containing water used in the present invention may be any drinkable component, and its content is preferably 25% by weight or less, more preferably 20% by weight or less. If it exceeds 30% by weight, the content of isoprenoid quinones is limited, which is economically disadvantageous.

[0029] The isoprenoid quinone-containing emulsion composition of the present invention can be blended with known oil-soluble or water-soluble ingredients as long as the effects of the present invention are not impaired. Examples of oil-soluble ingredients include vegetable oils such as soybean oil, rapeseed oil, olive oil, and safflower oil, animal oils such as fish oil and egg yolk oil, medium-chain fatty acid oils, oil-soluble flavorings, fat-soluble vitamins (vitamins A, D, E, and K), coloring agents, specific gravity adjusters, and antioxidants. Examples of water-soluble ingredients include water-soluble vitamins (vitamin C), thickening polysaccharides, pH adjusters, and stabilizers.

[0030] The isoprenoid quinone-containing emulsion composition of the present invention can be produced by a known method, for example, by a production method comprising the following steps. Isoprenoid quinones (coenzyme Q10) and other oil-soluble ingredients, if necessary, are heated and dissolved while stirring with a mixer to form the oil phase. Similarly, water-soluble emulsifiers, glycerin, and other water-soluble ingredients are heated and dissolved while stirring with a mixer to form the water phase. Next, the oil phase is added to the prepared aqueous phase while stirring with a stirrer to emulsify. If necessary, the resulting emulsion is homogenized using a high-pressure emulsifier or the like to uniformly refine the emulsion particles.

[0031] The isoprenoid quinone-containing emulsion composition of the present invention can be obtained by a mechanical emulsification method using a common emulsifier. Examples of equipment that can be used in the mechanical emulsification method include a homomixer, an ultramixer, and a clearmix. Examples of high-pressure emulsifiers that can be used for the homogenization treatment include a high-pressure homogenizer, a microfluidizer, and a nanomizer.

[0032] By the above-mentioned emulsification method, the emulsion particle size of the isoprenoid quinone-containing emulsion composition of the present invention is adjusted to preferably 200 nm or less, more preferably 100 nm or less, and even more preferably 60 to 80 nm, from the viewpoint of emulsion stability.

[0033] The emulsion particle size can be measured using a commercially available particle size distribution analyzer, etc. Known methods for measuring emulsion particles include optical microscopy, electron microscopy, laser diffraction, and dynamic light scattering, and devices based on each principle are commercially available. [Example]

[0034] The present invention will now be described in detail with reference to examples, but the present invention is not limited to these examples.

[0035] [Examples 1 to 3, Comparative Examples 1 to 3 ] As shown in Table 1, isoprenoid quinones and medium-chain fatty acid oils were mixed while stirring with a stirrer, and dissolved by heating (70 to 80°C) to obtain an oil phase. Similarly, polyglycerol fatty acid ester, enzymatically decomposed lecithin, and glycerin were dissolved while heating (70 to 80°C), and stirred and mixed with a stirrer to obtain an aqueous phase. The oil phase was added to the aqueous phase, emulsified with a homomixer, and homogenized at a pressure of 40 MPa using a high-pressure homogenizer to obtain an emulsion composition containing isoprenoid quinones (Examples 1 to 3, Comparative Examples 1 to 3). 3 These emulsion compositions were evaluated as follows. In the present examples and comparative examples, the polyglycerol fatty acid esters 1) to 3) in Table 1 were Decaglyn 1-OVEX (product name: decaglycerol monooleate), Decaglyn 1-SVEX (product name: decaglycerol monostearate), and Hexaglyn 1-SV (product name: hexaglycerol monostearate) (all manufactured by Nikko Chemicals), respectively, and the enzymatically hydrolyzed lecithin used was SLP Paste Lyso (product name: manufactured by Tsuji Oil Mills).

[0036] [Emulsification particle size] Examples 1 to 3 and Comparative Examples 1 to 3 The emulsion compositions obtained in step 1 were each diluted with ion-exchanged water to a concentration of 0.5% by weight, and the emulsion particle size (nm) was measured using a dynamic light scattering device (ELSZ-2, manufactured by Otsuka Electronics Co., Ltd.).

[0037] [Emulsification stability] Examples 1 to 3 and Comparative Examples 1 to 3 The emulsion composition obtained in step 1 was stored in a thermostatic chamber set at 40°C, and after 3 months, the change in emulsion particle size of the emulsion composition was measured, and the emulsion stability was evaluated based on the following criteria. ◎: The change in emulsion particle size is 20 nm or less. ◯: The change in emulsion particle size is 50 nm or less. △: The change in emulsion particle size is 50 nm or more, but no change in appearance such as precipitation or separation is observed. ×: Changes such as precipitation or separation are observed in appearance. In the present invention, "excellent emulsion stability" refers to an evaluation of ⊚ or ◯.

[0038] [Dispersibility in water] To 200 mL of ion-exchanged water, Examples 1 to 3 and Comparative Examples 1 to 3 1 g of the emulsion composition obtained in 1. was added to the mixture, stirred with a stirrer, and the state of dispersion was visually confirmed, and the dispersibility in water was evaluated based on the following criteria. ◎: Disperses uniformly within 20 seconds of stirring. ○: Disperses uniformly within 30 seconds of stirring. △: Uniformly dispersed within 60 seconds of stirring. ×: Undissolved material is visually confirmed after 60 seconds of stirring. In the present invention, "excellent dispersibility in water" refers to a material that has been evaluated as ⊚ or ◯.

[0039] [Heat resistance and acid resistance of dispersion liquid] The dispersions of Examples 1 to 3 and Comparative Examples 1 to 3 were each added to a citric acid / sodium citrate solution (for evaluating the acid resistance of the dispersion) or ion-exchanged water (for evaluating the heat resistance of the dispersion) adjusted to pH 3.0. 3 The emulsion composition obtained in step 1 was added and mixed to a concentration of 0.5% by weight, and the solution was heated until its temperature reached 85°C, and then heat sterilization was carried out for 30 minutes while maintaining that temperature. The solution was left at room temperature, and the change in emulsion particle size was measured, and the heat resistance and acid resistance of the dispersion were evaluated based on the following criteria. ◎: The change in emulsion particle size before and after heating is 20 nm or less. ◯: The change in emulsion particle size before and after heating is 50 nm or less. △: The change in emulsified particles before and after heating is 50 nm or more, but no oil floating or sediment is observed on the surface. ×: Oil floating or sediment was observed on the appearance before and after heating. ◎: The difference in emulsified particle size between the ion-exchanged water diluted solution and the acid diluted solution is 20 nm or less. ◯: The difference in emulsified particle size between the ion-exchanged water diluted solution and the acid diluted solution is 50 nm or less. △: The difference in emulsified particle size between the ion-exchange water diluted solution and the acid diluted solution is 50 nm or more, but no oil floating or sediment is observed on the exterior. ×: Oil floating or sediment was observed on the appearance of the diluted acidic solution. In the present invention, "excellent heat resistance and acid resistance of the dispersion" refers to a dispersion that is rated as ⊚ or ◯.

[0040] [Dispersion stability] The above-prepared Examples 1 to 3 and Comparative Examples 1 to 3 The acidic diluted solution of the emulsion composition obtained in step 1 was stored in a thermostatic chamber set at 25°C, and after 3 months, the change in the emulsion particle size of the acidic diluted solution of the emulsion composition was measured, and the dispersion stability was evaluated based on the following criteria. ◎: The change in emulsion particle size is 20 nm or less. ◯: The change in emulsion particle size is 50 nm or less. △: The change in emulsion particle size is 50 nm or more, but no change in appearance such as precipitation or separation is observed. ×: Changes such as precipitation or separation are observed in appearance. In the present invention, "excellent dispersion stability" refers to a dispersion that is evaluated as excellent or excellent.

[0041] [Economics] Examples 1 to 3 and Comparative Examples 1 to 3 The coenzyme Q10 content in the emulsion composition obtained in step 1 was used as the basis for the evaluation. ◎: Coenzyme Q10 content is 21% by weight or more. ◯: Coenzyme Q10 content is 15% by weight or more and less than 21% by weight. △: Coenzyme Q10 content is 10% by weight or more and less than 15% by weight. ×: Coenzyme Q10 content is less than 10% by weight. In the present invention, "excellent in economy" refers to the above evaluation of ⊚ or ◯.

[0042] [comprehensive evaluation] Taking into consideration the evaluation results of the emulsion stability, water dispersibility, heat resistance and acid resistance of the dispersion, dispersion stability, and economic efficiency, a comprehensive evaluation was made according to the following criteria. ◎: Very good ○:Good △: Slightly bad ×: Bad

[0043] [Table 1]

[0044] As is clear from Table 1, Examples 1 to 3, in which two types of polyglycerol fatty acid esters with an HLB of 10 to 15 were blended with lecithin to prepare emulsion particle sizes of 100 nm or less, showed a clear dispersion stabilization effect and were economically advantageous.

[0045] The isoprenoid quinone-containing emulsion composition of the present invention has been described based on the above embodiment, but it goes without saying that it is not limited to the above embodiment and can include various modifications, changes, and improvements to the various disclosed elements (including each element of each claim, each element of each embodiment or example, each element of each drawing, etc.) within the scope of the present invention and based on the basic technical idea of ​​the present invention. Furthermore, various combinations, substitutions, and selections of the various disclosed elements (including each element of each claim, each element of each embodiment or example, each element of each drawing, etc.) are possible within the scope of the claims of the present invention.

[0046] Further problems, objects and developments of the present invention will become apparent from the entire disclosure of the present invention, including the claims.

[0047] For numerical ranges set forth herein, it should be understood that any numerical value or subrange included within that range is specifically set forth unless expressly stated otherwise.

Claims

1. The isoprenoid quinone-containing emulsion composition contains (A) isoprenoid quinones, (B) two or more types of polyglycerol fatty acid ester and lecithin, (C) a polyhydric alcohol, and (D) an aqueous phase component containing water, and has an emulsion particle size of less than 100 nm. The emulsion composition has excellent emulsion stability at high temperatures of 25°C or higher, dispersibility in water, heat resistance and acid resistance of the dispersion, dispersion stability, and economy.

2. 2. The isoprenoid quinone-containing emulsion composition according to claim 1, wherein the content of the isoprenoid quinone in (A) is 20 to 30% by weight based on the total weight of the composition.

3. 3. The isoprenoid quinone-containing emulsion composition according to claim 1, wherein the polyglycerol fatty acid ester (B) has an HLB of 10 or more and 15 or less.

4. 4. The isoprenoid quinone-containing emulsion composition according to claim 1, wherein the isoprenoid quinone (A) is coenzyme Q10.

5. The isoprenoid quinone-containing emulsion composition according to any one of claims 1 to 4, which does not contain a sucrose fatty acid ester.

6. The isoprenoid quinone-containing emulsion composition according to any one of claims 1 to 5, wherein the two or more polyglycerol fatty acid esters (B) are a combination of decaglycerol monostearate and decaglycerol monooleate.

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