JP2009029755A - Method for producing coenzyme q10 particle - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method capable of commercially producing fine coenzyme Q<SB>10</SB>particles similar to stock powder, having a high content and excellent in powdery material flow characteristics, efficiently, by simple equipment and with easy operation. <P>SOLUTION: This method for producing the coenzyme Q<SB>10</SB>particles comprises the following (1) and (2) processes. (1) A process of emulsifying and dispersing the coenzyme Q<SB>10</SB>with water in the presence of a surfactant and at the temperature of at or higher than the melting temperature of the coenzyme Q<SB>10</SB>and preparing an O/W emulsion, and (2) a process of cooling the O/W emulsion in the presence of a water soluble dispersant, while flowing by agitation, to the temperature of at or lower than the solidifying temperature of the coenzyme Q<SB>10</SB>to obtain solid particles. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

The present invention relates to a process for producing coenzyme Q ₁₀ particles. Coenzyme Q ₁₀ is excellent, food, food with nutrient function claims, food for specified health use, nutritional supplement, nutritional, animal drug, drink, feed, cosmetics, pharmaceuticals, therapeutic agents, is a compound useful as a prophylactic, etc. .

Coenzyme Q ₁₀ is an electron transport system components of the mitochondria in cells of a living body of a human, by repeating the oxidation and reduction in mitochondria, addition plays a function as a transfer component in the electron transport system, reduced coenzyme Q ₁₀ are known to have an antioxidant effect.

Of the coenzyme Q _10, oxidized coenzyme Q ₁₀ is, as a health food is in the United States and Europe, has been used as congestive heart failure drug in Japan, in recent years, health food in Japan, also used as a dietary supplement and cosmetics It is coming. In particular, health food, in the field of dietary supplements, products that oxidized coenzyme Q ₁₀ was soft capsules of has become the mainstream.

The coenzyme Q ₁₀ containing reduced coenzyme Q _10, rather than coenzyme Q ₁₀ alone conventional oxidized, or the like is excellent in oral absorbability, in recent years, has become their effectiveness is known.

Bulk powder of coenzyme Q ₁₀ is, for example, synthetic, fermentation, after obtaining coenzyme Q ₁₀ crude product by a method such as extraction from natural products, coenzyme Q ₁₀ sections of the effluent by chromatography concentrated It can be obtained by crystallization by crystallization. However, this way bulk powder coenzyme Q ₁₀ obtained is in the form of plate-like crystals, or needle-like crystals, aggregation of sticking or bulk powder to a solid surface is likely to occur, the powder flow properties Is known to be very bad. In the case of using coenzyme Q ₁₀ as a tablet applications or soft capsules applications, in order to ensure uniformity during preparation filling, it is necessary to make the maximum particle diameter is 300μm or less. Therefore to improve the bulk powder coenzyme Q _10, the development of technology that good particle powder flow characteristics can granulation has been desired fine.

Coenzyme of the enzyme Q _10, the granulation or granulation method oxidized coenzyme Q _10, for example in a fluidized bed apparatus or the like, while mixing the excipients oxidized coenzyme Q _10, spray coated with the coating material An example (Patent Document 1) is known. However, particles of oxidized coenzyme Q ₁₀ obtained in this way, since the material used for the excipients and coatings contain a large amount, not high oxidized coenzyme Q ₁₀ content in the particles .

Of coenzyme Q _10, the granulation method intended for the enzyme Q _10, and adding a high concentration liquid phase of reduced coenzyme Q ₁₀ in a poor solvent, a method of granulating (Patent Document 2) known However, it is difficult to produce fine particles by the granulation method, and additional facilities such as a tank for preparing a high concentration liquid phase and a pump for feeding the liquid are required.

By the way, in a report for solidifying and granulating a general fat-soluble substance, a low-melting-point substance was melted in water at a temperature higher than the melting point and formed into droplets, and then cooled and solidified for granulation. There is an example (patent document 3).
JP 2006-213601 A JP 2004-130201 A JP-A-9-124405

As mentioned above, bulk powder of coenzyme Q ₁₀ because it has the form of a plate-like crystals, or needle-like crystals, static electricity is easily generated, thereby formulation device or the like, to the solid surface sticking and bulk powder of aggregation occurs, or decrease the work efficiency at the time of weighing, occurs adhesion to bulk powder containers and formulations device during tableting or during capsule filling, such as the formulation of coenzyme Q ₁₀ can not be smoothly productivity and operation There was a problem with sex.

Moreover, when the granulation method of the conventional coenzyme Q _10, in order to use a large amount of excipients, which cause a decrease in the content of coenzyme Q ₁₀ in the resulting particles, mixing the food and pharmaceutical applications, production There have been problems such as deterioration in efficiency and insufficient powder flow characteristics.

An object of the present invention is to provide a production method capable of efficiently industrially producing fine coenzyme Q ₁₀ particles having a high content and excellent powder flow characteristics like a bulk powder with simple equipment and simple operation. It is.

Result of intensive studies to solve the above problems, the coenzyme Q ₁₀ was emulsified and dispersed in water, soluble preparing a coenzyme Q ₁₀ was oil into O / W emulsions, the O / W emulsion while flowing in the presence sexual dispersing agents, coenzyme Q is cooled to solidification temperature of ₁₀ or less, by stirring as to obtain solid particles and dispersion conditions to operate the two different steps, the powder with a high content of excellent flow properties and yet fine coenzyme Q ₁₀ particles bulk powder par efficiently found that can be produced at industrially possible method, to complete the present invention.

That is, the present invention provides a water (1) coenzyme Q _10, at a temperature above the melting point of coenzyme Q ₁₀ in the presence of a surfactant and emulsified and dispersed to prepare an O / W emulsion, (2) the O Coenzyme Q ₁₀ comprising two steps of obtaining solid particles by cooling the / W emulsion with stirring in the presence of a water-soluble dispersant to below the solidification temperature of Coenzyme Q ₁₀ A method for producing particles. The present invention also relates to Dr. In the powder flow characteristics indicators CARR is 80 or more, about coenzyme _{Q 10} particles wherein the average particle diameter of spherical particles of 1 to 300 [mu] m.

Particles of coenzyme Q ₁₀ obtained by the present invention, the particle size is excellent in uniform powder flow properties, adhesion to the bulk powder containers and formulations device, aggregation hardly occurs in bulk powder, the filling of the device Are better. The manufacturing method of the present invention, by using a simple equipment, not only be carried out by a simple operation, the production of fine coenzyme Q ₁₀ particles coenzyme Q ₁₀ in high content and, and bulk powder par Is possible.

  Hereinafter, embodiments of the present invention will be described in detail.

Method for producing particles of coenzyme Q ₁₀ in the present invention is a method for producing coenzyme Q ₁₀ particles containing the following steps (1) and (2).

(1) and the coenzyme Q ₁₀ and water, at a temperature above the melting point of coenzyme Q ₁₀ in the presence of a surfactant and emulsified and dispersed to prepare an O / W emulsion.

(2) The O / W emulsion, the presence a water-soluble dispersing agent, and cooled to below the solidification temperature of the coenzyme Q ₁₀ while flowing a stirrer, obtaining a solid particle.

Coenzyme Q ₁₀ is an essential component which is distributed widely vivo, as described above, oxidized and reduced form are present. In the present invention, as a coenzyme Q _10, oxidized coenzyme Q _10, even when using any of the reduced coenzyme Q _10, it is possible to obtain an excellent particle powder flow characteristics. Of course, it may be a mixture of reduced coenzyme Q ₁₀ and oxidized coenzyme Q ₁₀ as a coenzyme Q _10. Although the production method of this invention can be applied to the any form, since the direction of reduced coenzyme Q ₁₀ than oxidized coenzyme Q _10, are superior in oral absorption and other pharmacological effects, coenzyme Q to apply the reduced coenzyme Q ₁₀ or oxidized coenzyme Q ₁₀ in a mixture of reduced coenzyme Q ₁₀ is generally preferred as _10. The mixing ratio of the oxidized coenzyme Q ₁₀ in the case where a mixture of reduced coenzyme Q ₁₀ is not particularly limited, preferably the ratio of reduced coenzyme Q ₁₀ in coenzyme Q ₁₀ is 20 wt% or more, more Preferably it is 40 weight% or more, More preferably, it is 60 weight% or more, Most preferably, it is 80 weight% or more. In the present specification, when described only a coenzyme Q _10, oxidized, irrespective of the reduced form, when both are mixed is also indicative of the total mixture.

While feeding concentration of coenzyme Q ₁₀ in the manufacturing method of the present invention is not particularly limited, from the viewpoint of productivity, the higher the charge density of coenzyme Q ₁₀ in water preferably, for example, in the above step (1), water ratio of coenzyme Q ₁₀ for the 1 wt% or more, and particularly preferably 5 wt% or more. On the other hand, if the charge density of coenzyme Q ₁₀ in water is 30 wt% or more, is difficult to control the particle diameter, he is difficult to obtain uniform particles, preferably less.

In the production method of the present invention, in order to prepare an oily substance of coenzyme Q10 as an O / W emulsion in the above step (1), it is preferable to carry out emulsification dispersion in the presence of a surfactant having an HLB of 6 or more. From the viewpoint of oil droplet dispersion formation in the aqueous phase, the HLB is more preferably 8 or more, and particularly preferably 10 or more. Moreover, as said surfactant, what can be used for foodstuffs or a pharmaceutical use is preferable, For example, glycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, and lecithin can be mentioned.
Examples of the glycerin fatty acid esters include monoglycerin fatty acid organic acid esters, monoglycerin fatty acid esters, and polyglycerin fatty acid esters. Specific examples of the monoglycerin fatty acid organic acid ester include monoglycerin stearic acid citrate, monoglycerin stearic acid acetate, monoglycerin stearic acid succinic acid ester, monoglycerin caprylic acid succinic acid ester, and monoglycerin stearic acid lactic acid. Examples include esters and monoglyceryl stearic acid diacetyltartaric acid esters. Examples of the monoglycerin fatty acid ester include monoglycerin laurate, monoglyceryl myristate, monoglycerin oleate, and monoglycerin stearate. Specific examples of polyglycerol fatty acid esters include triglycerol monolaurate, triglycerol monomyristate, triglycerol monooleate, triglycerol monostearate, pentaglycerol monomyristate, pentaglycerol trimyristin. Acid ester, pentaglycerin monooleate, pentaglycerin trioleate, pentaglycerin monostearate, pentaglycerin tristearate, pentaglycerin monostearate, hexaglycerin monocaprylate, hexaglycerin dicaprylate , Hexaglycerin monolaurate, hexaglycerin monomyristate, hexaglycerin Phosphorus monooleate, hexaglycerin monostearate, decaglycerin monolaurate, decaglycerin monomyristic acid, decaglycerin monooleate, decaglycerin monopalmitate, decaglycerin monostearate, decaglycerin distearin Acid ester etc. are mentioned.

  Examples of the sucrose fatty acid esters include those obtained by esterifying one or more hydroxyl groups of sucrose with fatty acids having 6 to 18, preferably 6 to 12 carbon atoms. Specific examples include sucrose palmitate and sucrose stearate.

  Examples of the sorbitan fatty acid esters include those obtained by esterifying one or more hydroxyl groups of sorbitans with fatty acids having 6 to 18 carbon atoms, preferably 6 to 12 carbon atoms. Specific examples include sorbitan monostearate, sorbitan monooleate, and the like.

  Examples of the lecithins include egg yolk lecithin, purified soybean lecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, sphingomyelin, dicetylphosphate, stearylamine, phosphatidylglycerol, phosphatidic acid, phosphatidylinositolamine, cardiolipin, ceramide phosphorylethanolamine, Examples thereof include ceramide phosphorylglycerol, lysolecithin, and mixtures thereof.

  Needless to say, two or more of the surfactants shown here may be used in combination.

  In step (1), the concentration at which these surfactants are added to the aqueous phase is not particularly limited, but is preferably included in a range where the concentration is 0.001 to 5% by weight, and more preferably the concentration. The range is 0.01 to 1% by weight.

In step (1) of the manufacturing method of the present invention, when preparing the coenzyme Q ₁₀ was oil into O / W emulsion, the temperature of coenzyme Q ₁₀ is melted, ie a temperature above the melting point of coenzyme Q ₁₀ There is a need. Coenzyme Q ₁₀ is sufficiently melted, to a state in which the solid component is not present, in the step (1), a mixture of coenzyme Q ₁₀ and water, at a temperature of 50 ° C. to 80 ° C. It is preferable to emulsify and disperse, and it is more preferable to emulsify and disperse under a temperature condition of 55 to 60 ° C.

The emulsification and dispersion carried out for preparing the O / W emulsion of the coenzyme Q _10, emulsifying dispersing machine are various general purpose, for example a homomixer, homodisperser, homogenizer, high pressure homogenizer, colloid mill, ultrasonic emulsifier, etc. Can be used.

In the production method of the present invention, the flow of the O / W emulsion of coenzyme Q ₁₀ prepared by the aforementioned method in step (1), in the next step (2), the added aqueous phase of the water-soluble dispersing agent It cooled while to obtain solid particles of coenzyme Q _10.

  Although it does not specifically limit as a water-soluble dispersing agent which can be used in the process (2) of the manufacturing method of this invention, The thing which can be used for foodstuffs or pharmaceuticals is preferable. Examples of such water-soluble dispersants include gum arabic, gelatin, agar, starch, pectin, carrageenan, casein, alginic acids, soy polysaccharides, pullulan, celluloses, and xanthan gum.

  Examples of the alginic acids include alginic acid, sodium alginate, potassium alginate and the like.

  The soybean polysaccharide is a water-soluble polysaccharide extracted from soybean and is composed of polysaccharides such as galactose, arabinose, galacturonic acid, xylose, full course, glucose, rhamnose and the like.

  Examples of the celluloses include crystalline cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxyethyl methyl cellulose, carboxymethyl cellulose, and methyl cellulose.

  Two or more of the water-soluble dispersants shown here can be used in combination.

  In step (2), the concentration at which the water-soluble dispersant is added to the aqueous phase is not particularly limited. The concentration is in the range of 0.005 to 3% by weight.

While in the present invention, in the step (2), maintaining the water-soluble dispersant, and added to the aqueous phase dispersed coenzyme Q _10, the coenzyme Q ₁₀ in the resulting particles in a high content, fine coenzyme Q ₁₀ particles excellent bulk powder par the powder flow properties can be obtained.

In the step (2) of the manufacturing method of the present invention, while maintaining the shape of the O / W emulsion prepared in step (1), it is necessary to solidify the coenzyme Q ₁₀ at a temperature below the melting point of coenzyme Q ₁₀ is there. In step (2), in order to solidify, which may be the melting point or less of coenzyme Q _10, from the viewpoint of the physical properties of the coenzyme Q ₁₀ particles obtained, it is preferred to cool to a temperature of 40 ° C. or less Furthermore, it is preferable to cool to a temperature of 35 ° C. or lower.

In the step (2), upon cooling the O / W emulsion, the cooling rate is too fast, the uniformity of the coenzyme Q ₁₀ particles obtained becomes low, since it becomes difficult to control the particle size, The cooling rate is preferably 0.5 ° C./min or less, and more preferably 0.2 ° C./min or less. The lower limit of the cooling rate is not particularly limited, but if the cooling rate is extremely slow, production problems such as increased generation of fine powder during particle generation, etc., the cooling rate is preferably 0.01 ° C./min or more, More preferably, it is 0.05 ° C./min or more.

In step (2) of the production method of the present invention, it is necessary to cool the O / W emulsion prepared in step (1) while maintaining the shape of the O / W emulsion. It is preferable that the required power per unit volume is 0.01 kW / m ³ or more, more preferably 0.05 kW / m ³ or more. But not limited stirred maximum power requirement especially when the power required is significantly larger, intensifies entrainment of bubbles from the liquid free surface in coenzyme Q ₁₀ solidifies, since a failure such as deformation occurs, stirring required The upper limit of power is preferably 1.5 kW / m ³ or less, more preferably 1.0 kW / m ³ or less.

In the production method of the present invention, the preparation method of the surfactant in preparing the O / W emulsion in the step (1) and the preparation method of the water-soluble dispersant in the step (2) are coenzyme Q _10. The O / W emulsion can be prepared, and there is no particular limitation as long as the O / W emulsion is cooled and fine solid particles are obtained. In the step (1), the surfactant and the water-soluble dispersion are used. It is also possible to charge the agent together.

In the production method of the present invention, the coenzyme Q _{10 is used in} the O / W emulsion preparation step (step (1)) and the cooling step (step (2)) for obtaining coenzyme Q ₁₀ solid particles. The combination of apparatuses is not limited, and if these two independent processes can be carried out, for example, it is also possible to carry out with a single apparatus in which an emulsifying disperser is combined with an external circulation line of a stirring tank. .

In the manufacturing method of this invention, this manner coenzyme Q ₁₀ solid particles obtained, for example, centrifugation, pressure filtration, filtration under reduced pressure or the like solid-liquid separation by further performs cake optionally washed, Furthermore, it is obtained as dry particles by performing a drying process such as vacuum drying.

In particular, reduced coenzyme Q ₁₀ is oxidized by molecular oxygen, since the oxidized coenzyme Q ₁₀ tends to-produced, in the present invention, reduced coenzyme Q ₁₀ and reduced coenzyme Q as a coenzyme Q _{10 10} the case of using a mixture of oxidized coenzyme Q _10, the series of operations is preferably carried out under an oxygen atmosphere. The deoxygenated atmosphere can be achieved by substitution with an inert gas, reduced pressure, boiling, or a combination thereof. Examples of the inert gas include nitrogen gas, helium gas, argon gas, hydrogen gas, and carbon dioxide gas, preferably nitrogen gas.

Coenzyme Q ₁₀ particles obtained by the production method of the present invention are excellent particle powder flow characteristics spherical. Specifically, Dr. It is a coenzyme Q ₁₀ particle having a powder flow characteristic index of CARR of 80 or more. From the viewpoint of the powder flow properties, its index is preferably higher, by properly selecting the preferred production conditions, it is possible to obtain more than 80 coenzyme Q ₁₀ particles. As of coenzyme Q ₁₀ bulk powder obtained by a known crystallization method, Dr. If the powder flow properties index CARR is below 50, the fluidity is deteriorated, or worsening efficiency at transfer of coenzyme Q ₁₀ particles, or the like device filled can not be smoothly, productivity and operability issues is there.

  In addition, Dr. The powder flow characteristic index of CARR is an index that comprehensively evaluates the angle of repose, compressibility, spatula angle, and uniformity of particles, and is defined in CHENICAL ENGINEERING-January 18, 1965. Dr. Table 1 shows the definition of the CARR powder flow characteristic index.

The shape of coenzyme Q ₁₀ particles obtained by the production method of the present invention is spherical as mentioned above. The average particle size is not particularly limited depending on the stirring speed and cooling rate during production, and can be appropriately prepared. However, when used as a tableting application or a soft capsule application, the average particle diameter should be 1 to 300 μm. preferable. When the average particle diameter of the coenzyme Q ₁₀ particles exceeds 300 μm, for example, there is a problem that the filling amount is not uniform at the time of tableting or soft capsule filling.

In the production method of the present invention, since no excipient or coating agent for granulation is required in addition to a trace amount of surfactant or water-soluble dispersant, coenzyme Q in the resulting coenzyme Q ₁₀ particles is not necessary. ₁₀ content is high, for example, 90 wt% or more coenzyme _{Q 10} content in the particles, more preferably 95 wt% or more. The higher the content of coenzyme Q ₁₀ in the particles, when mixed in food and pharmaceutical applications, improved production efficiency, also preferred because the degree of freedom in the design of the formulation is increased. However, it does not exclude adding or mixing excipients or coating the coenzyme Q ₁₀ particles obtained by the production method of the present invention as necessary.

The coenzyme Q ₁₀ particles obtained by the production method of the present invention can be filled into tablets and soft capsules as they are, and can also be dissolved and mixed in compatible fats and oils. It can be processed and used in the same manner as ₁₀ bulk powder.

Next, the present invention will be specifically described with reference to examples. In the examples and comparative examples, oxidized coenzyme Q ₁₀ (raw powder) and reduced coenzyme Q ₁₀ (raw powder) manufactured by Kaneka Corporation were used as raw materials for the coenzyme Q ₁₀ particles. The content of coenzyme Q ₁₀ in the particles in the examples were determined by the following HPLC analysis, the content of coenzyme Q ₁₀ obtained are not intended to define the limits of the content in the present invention.

(HPLC analysis conditions)
Column: SYMMETRY C18 (manufactured by Waters) 250 mm (length) 4.6 mm (inner diameter), mobile phase; C ₂ H ₅ OH: CH ₃ OH = 4: 3 (v: v), detection wavelength: 210 nm, flow rate: 1 mL / min, retention time of reduced coenzyme Q10; 9.1min, retention time of oxidized coenzyme _{Q 10; 13.3min.}

Example 1
500 mL of ion-exchanged water containing 0.01% by weight of decaglycerin monooleate (manufactured by Riken Vitamin, Poem J-0381V) is heated to 55 ° C., and 30 g of oxidized coenzyme Q ₁₀ (raw powder) is added. in a state in which coenzyme Q ₁₀ is sufficiently melted, emulsified and dispersed by a homogenizer, to prepare an O / W emulsion of oxidized coenzyme Q _10. Subsequently, the O / W emulsion was charged into a separable flask with a stirrer having an internal volume of 1000 mL, and an aqueous gum arabic solution was added so that the gum arabic concentration in the liquid was 1% by weight. Then, stirring was performed using a disk turbine blade (power required for stirring per unit volume: 0.34 kW / m ³ ). Thereafter, the O / W emulsion was cooled to 35 ° C. at a cooling rate of 0.2 ° C./min with the stirring condition, and then subjected to suction filtration and vacuum drying to obtain coenzyme Q ₁₀ particles. Coenzyme _{Q 10} content of the resulting particles was 99.4 wt%. The resulting coenzyme Q ₁₀ particles microscope was observed with (Keyence digital microscope VH-6200, hereinafter the same), has been a spherical particles having a mean particle size of about 42 .mu.m. The obtained reduced coenzyme Q ₁₀ particles a scanning electron microscope was observed with (Hitachi S-800, hereinafter SEM hereinafter), spherical particle shape as shown in FIG. 1 was observed . Further, the obtained coenzyme Q ₁₀ particles Powder Tester (Hosokawa Micron Powder Tester PT? R type, hereinafter the same) by, were evaluated in the powder flow properties, Dr. The powder flow characteristic index of CARR was 83.5, and the degree of flow characteristic was “Good”.

(Example 2)
Using reduced coenzyme Q _{10 (bulk} powder) 30 g instead of oxidized coenzyme Q _10, all under operation by a nitrogen atmosphere, and the other reduced coenzyme Q by the same method and conditions as in Example 1 _Ten particles were obtained. Reduced coenzyme _{Q 10} content of the resulting particles was 99.2 wt%. The resulting reduced coenzyme Q ₁₀ particles were observed under a microscope, has been a spherical particles having a mean particle size of about 28 .mu.m. Furthermore, the resulting reduced coenzyme Q ₁₀ particles powder tester, were evaluated in the powder flow properties, Dr. The powder flow characteristic index of CARR was 81.0, and the degree of flow characteristic was “Good”.

(Comparative Example 1)
Observation of the oxidized coenzyme Q ₁₀ bulk powder used as a raw material of Example 1 a microscope, was a crystalline form having an average particle diameter of about 40 [mu] m. Further, observation of the oxidized coenzyme Q ₁₀ bulk powder in SEM, plate-like crystal form as shown in FIG. 2 was observed. Further, when the powder tester oxidized coenzyme Q ₁₀ bulk powder, were evaluated in the powder flow properties, Dr. The powder flow characteristic index of CARR was 41.0, and the degree of flow characteristic was “Poor”.

(Comparative Example 2)
Observation of the reduced coenzyme Q ₁₀ bulk powder used as a raw material for Example 2 a microscope was a finely divided with an average particle size of about 45 [mu] m. In addition, Dr. reduced coenzyme Q ₁₀ bulk powder by the powder tester, were evaluated in the powder flow properties The powder flow characteristic index of CARR was 48, and the degree of flow characteristics was “Poor”.

(Comparative Example 3)
A separable flask with an internal volume of 1000 mL equipped with a stirrer was charged with 10 g of oxidized coenzyme Q ₁₀ (raw powder) and 200 mL of 99.5% ethanol, and 3 mL of high oleic safflower oil was added as an auxiliary solvent at 45 ° C. Then, it was cooled to 10 ° C. at a cooling rate of 0.2 ° C./min while rotating and stirring at 150 rpm using a Max Blend blade. Suction filtration, coenzyme _{Q 10} content of the obtained coenzyme _{Q 10} particles by vacuum drying was 99.5 wt%. The resulting coenzyme Q ₁₀ particles were observed under a microscope, has been a spherical aggregation crystals of an average particle size of about 130 .mu.m. Further, the resulting coenzyme Q ₁₀ particles powder tester, were evaluated in the powder flow properties, Dr. The powder flow characteristic index of CARR was 74.5, and the degree of flow characteristic was “Fair”.

Coenzyme _{Q 10} particles obtained in Example 1-2 in Table 2, and the average particle size of coenzyme _{Q 10} bulk powder and coenzyme _{Q 10} particles of Comparative Examples 1 to 3, coenzyme _{Q 10} content, flour The evaluation results of body flow characteristics are shown.

2 is a SEM photograph of coenzyme Q ₁₀ particles of the present invention obtained in Example 1. Is an SEM photograph of coenzyme _{Q 10} bulk powder of Comparative Example 1.

Claims (11)

Following (1) and containing the steps of (2), method for producing coenzyme _{Q 10} particles.
The (1) and the coenzyme Q ₁₀ and water, and emulsified and dispersed at a temperature higher than the melting point of coenzyme Q ₁₀ in the presence of a surfactant to prepare an O / W emulsion (2) The O / W emulsion, water sex dispersant presence, by cooling to below the solidification temperature of the coenzyme Q ₁₀ while flowing a stirrer, obtaining a solid particle In step (1), The process according to claim 1 ratio of coenzyme Q ₁₀ relative to water is 1 wt% or more.   The method according to claim 1 or 2, wherein the ratio of the surfactant to water in the step (1) is 0.001 to 5% by weight.   The surfactant is at least one selected from the group consisting of glycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, and lecithins having an HLB of 6 or more. 4. The production method according to any one of 3 above.   The manufacturing method according to any one of claims 1 to 4, wherein a ratio of the water-soluble dispersant to water in the step (2) is 0.001 to 10% by weight.   The water-soluble dispersant is at least one selected from the group consisting of gum arabic, gelatin, agar, starch, pectin, carrageenan, casein, alginic acids, soy polysaccharides, pullulan, celluloses, and xanthan gum. The manufacturing method according to any one of claims 1 to 5.   The cooling rate in a process (2) is 0.01-0.5 degreeC / min, The manufacturing method of any one of Claims 1-6 characterized by the above-mentioned. The stirring at the time of cooling in the step (2) is performed under the condition that the power required for stirring per unit volume is 0.01 to 1.5 kW / m ^3. Manufacturing method. The process according to any one of claims 1 to 8, coenzyme Q ₁₀ is equal to or those containing reduced coenzyme Q _10. Spherical particles having an average particle diameter of 1 to 300 μm, and Dr. Coenzyme Q ₁₀ particles, wherein the powder flow characteristic index of CARR is 80 or more. Produced by the process according to any one of claims 1 to 9, coenzyme Q ₁₀ particles of claim 10, wherein.