WO2007080787A1

WO2007080787A1 - Coenzyme q10-containing water-soluble compositions

Info

Publication number: WO2007080787A1
Application number: PCT/JP2006/326016
Authority: WO
Inventors: Tsuyoshi Minemura; Hiroyuki Ikemoto
Original assignee: Nisshin Pharma Inc.
Priority date: 2006-01-12
Filing date: 2006-12-27
Publication date: 2007-07-19

Abstract

The invention provides coenzyme Q10-containing compositions which are free from synthetic emulsifiers such as glycerol fatty acid esters, polyglycerol fatty acid esters, organic acid monoglycerides or sucrose fatty acid esters and which contain coenzyme Q10 at high proportion and are excellent in the stability of coenzyme Q10 and the bioavailability thereof. Coenzyme Q10-containing liquid compositions are obtained by dispersing and emulsifying coenzyme Q10 in an aqueous fluid containing a water-soluble substance composed of starch octenylsuccinate and dextrin and sorbitol and/or propylene glycol. Further, coenzyme Q10-containing solid compositions are obtained by drying the liquid compositions, if necessary, together with a carrier.

Description

Specification

Coenzyme Q-containing water-soluble composition

Ten

Technical field

[0001] The present invention relates to an aqueous liquid containing coenzyme Q containing a water-soluble substance and a polyhydric alcohol.

Ten

Coenzyme Q obtained by dispersing and emulsifying in the body

10 Containing composition. More specifically, in the aqueous liquid containing octenyl succinate starch and dextrin water-soluble substance and sorbitol and z or propylene glycol as polyhydric alcohol, Coenzyme Q

It relates to a composition obtained by dispersing and emulsifying 10. The composition is Coenzyme Q

10 can be contained in a high content and has excellent stability and absorbability.

Background art

[0002] Coenzyme Q is present in higher animals known as ubidecarenone or coenzyme Q

10 10

It is a kind of coenzyme Q (molecular formula C H 0, molecular weight 863.36). Coenzym Q

59 90 4 10 As a coenzyme, it is known as a vitamin-like active substance that has the effect of improving oxygen utilization efficiency as well as having biological activity. Coenzyme Q works on congested tissues

Ten

It is thought that it has an action such as anti-oxidation and the like that stabilizes biological membranes, and clinically, it has a pharmacological effect in improving symptoms of angina pectoris, heart failure, ischemic heart disease, and muscular dystrophy. It is also reported to be effective in the prevention and treatment of hypertension, arteriosclerosis, heart disease, diabetes and periodontal diseases, as well as prevention of side effects of anticancer drugs and psychotropic drugs, recovery of fatigue and recovery of motor function. ing. Thus, Coenzyme Q has high physiological activity and is in vivo.

Ten

It is a highly safe substance that exists.

In recent years, Coenzyme Q has been approved for use as a food product,

Ten

It has attracted much attention as a material.

[0003] However, Coenzyme Q is a lipophilic solid having a low melting point and is hardly soluble in water. others

Ten

Therefore, Kokonzym Q has very low absorbability after oral intake. Coenzyme Q

Ten

No. 10 is unstable and has a problem that it is decomposed by light or the like to produce hydroquinone, ubichromenol or the like.

[0004] Polyglycerin fat is used as a composition with enhanced noavailability of Coenzyme Q. Coenzyme Q is an aqueous emulsion using a fatty acid ester as an emulsifier.

Ten

Mix with an aqueous solution containing a water-soluble polymer substance 3 times the weight of Im Q and spray-dry it.

Ten

A Coenzyme Q-containing composition obtained by drying has been proposed (JP 59-51214 A).

Ten

Issue gazette). In addition, fat-soluble substances such as Coenzyme Q can be added to glycerin fatty acid esters and shochus.

Ten

It has been proposed to produce a fat-soluble substance aqueous liquid by emulsifying with sugar fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene hydrogenated castor oil and the like, polyhydric alcohol and water (Japanese Patent Application Laid-Open No. 2000-1999). 212066). Furthermore, Coenzyme Q is mixed with oil phase components such as vegetable oils and fatty acid esters, polyhydric alcohols and dairy oils.

Ten

Producing emulsified composition containing Coenzyme Q using emulsifier such as serine fatty acid ester

Ten

It has been proposed to do so (Japanese Patent Laid-Open No. 2003-238396). However, since emulsifiers such as glycerin fatty acid esters and sucrose fatty acid esters are highly viscous liquid substances, a large amount of excipients are added to obtain a solid composition from an emulsion using these emulsifiers. Resulting in a drying process that not only limits the content of Coenzyme Q.

Ten

However, there is a disadvantage that operability is lowered due to problems such as staging. In addition, when these emulsifiers are used, depending on the form of the food or drink, the flavor and texture may be impaired. In addition, since many of these emulsifiers are synthetic products, their use may not be desired. JP-A 2003-238396 discloses water-soluble polymers such as starch, dextrin, and arabic gum as emulsifiers. Emulsified compositions using these water-soluble polymers instead of synthetic emulsifiers are manufactured. Coenzyme Q stable in this way

Whether it is possible to obtain an emulsion containing 10 is unknown.

[0005] On the other hand, without using a synthetic emulsifier such as glycerin fatty acid ester,

10 As a method of dispersing and emulsifying Coenzyme Q in the presence of organic acid,

Ten

There is a method of dispersing and emulsifying in an aqueous liquid containing water-soluble substances such as mud, agar, water-soluble corn fiber, starch, gelatin, xanthan gum, casein, and dextrin (Japanese Patent Laid-Open No. 2003-55203). The ability to provide stable products with high bioavailability by this method. Products with even higher Coenzyme Q content are desired.

Ten

[0006] Further, there is a method for producing an emulsified powder by adding processed starch, sugars and water to a fat-soluble substance, followed by drying, and an emulsified powder product containing about 52% of tocopherol acetate is disclosed. (Japanese Patent Laid-Open No. 11-196785). However, if this method is applied to Coenzyme Q,

Ten

The resulting composition is insufficient in terms of emulsion stability.

[0007] Therefore, without using a synthetic emulsifier such as glycerin fatty acid ester, it is possible to contain Coenzyme Q at a high content, and to improve the stability and bioavailability of Coenzyme Q.

10 10

There is still a high demand for a Coenzyme Q-containing composition that excels in spirit.

10 Disclosure of the invention

Problems to be solved by the invention

[0008] An object of the present invention is to use a high content of coenzyme Q without using a synthetic emulsifier such as glycerin fatty acid ester, polyglycerin fatty acid ester, organic acid monoglyceride, propylene glycol fatty acid ester, sorbitan fatty acid ester, and sucrose fatty acid ester. Amount

Ten

Coenzyme with excellent stability and absorbency of Coenzyme Q

Ten

Providing a Q-containing composition.

Ten

Means for solving the problem

[0009] The present inventors conducted extensive research to solve the above problems, and found that Cohenzym Q

Obtained by dispersing and emulsifying 1 in an aqueous liquid containing a water-soluble substance and a polyhydric alcohol

0

Even if the composition increases the content of Coenzyme Q, it has excellent stability and absorbency.

Ten

It has been found that a zyme Q-containing composition can be produced. In particular, otate as a water-soluble substance

Ten

It has been found that an excellent composition containing Coenzyme Q can be obtained by using succinic acid powder and dextrin in combination and using sorbitol and / or propylene glycol as the polyhydric alcohol. That is, the present invention

Ten

Disperse Coenzyme Q in an aqueous liquid containing a specific amount of sorbitol and Z or propylene glycol, as well as water-soluble substances such as succinate starch and dextrin

10 relates to a liquid composition containing Coenzyme Q obtained by emulsification. Including this Coenzyme Q

10 10 By drying the liquid composition, a solid composition containing Coenzyme Q can be obtained.

Ten

wear. In the case of drying, a carrier can be used as necessary.

[0010] The Coenzyme Q-containing composition of the present invention has a high Coenzyme Q content.

10 10

It is extremely bioabsorbing that Coenzyme Q is absorbed even when taken on an empty stomach. It is a highly irritating composition. Therefore, the Coenzyme Q-containing composition of the present invention

Ten

Are in various forms of food, feed, cosmetics and high-content coenzyme Q

Ten

Materials to be added · Can be applied in a very wide range as raw materials.

The invention's effect

[0011] According to the present invention, even without using a synthetic emulsifier such as glycerin fatty acid ester, the coenzyme Q is contained in a high content, and the stability and bioavailability of coenzyme Q are improved.

10 10

Offering Coenzyme Q-containing compositions that are superior in terms of retiability (absorbability, bioavailability, etc.)

Ten

Is done. The liquid composition of the present invention is long despite the high content of Coenzyme Q.

Ten

A good emulsified state is maintained even after storage for a period. In addition, even when the solid composition of the present invention is stored for a long period of time, the solubility or dispersibility in an aqueous liquid such as water does not deteriorate, and a fine and stable aqueous composition can be formed by adding to the aqueous liquid. It is suitable. These compositions have the characteristic that Coenzyme Q is reliably absorbed even on an empty stomach.

Ten

To do. For this reason, the composition of the present invention can be added to various forms of food, drink, cosmetics and feed to achieve high bioavailability with high coenzyme Q.

Ten

The

BEST MODE FOR CARRYING OUT THE INVENTION

[0012] The Coenzyme Q-containing liquid composition of the present invention comprises sorbitol and / or propylene.

Ten

It is prepared by dispersing and emulsifying Coenzyme Q10 in an aqueous liquid containing a specific amount of water-soluble substance such as glyceryl glycol, octenyl succinic acid powder and dextrin. Specifically, Coenzyme Q 1-50% by weight, sorbitol and

10 Z or resulting pro propylene da recall 0.01 to 10 mass ^_0/0, and dispersed and emulsified in an aqueous liquid containing a water-soluble substance 4 to 30 wt% consisting of Otateyurukohaku acid starch and dextrin and water 40-94 wt% Is an aqueous liquid.

[0013] The liquid composition containing Coenzyme Q is dried to contain Coenzyme Q.

10 10 Can be a solid composition. In the case of drying, a carrier can be used as necessary. When the Coenzyme Q-containing liquid composition is dried without using a carrier

Ten

Coenzyme Q-containing solid composition is Coenzyme Q 3-80% by weight, sorbitol

10 10

And Z or propylene glycol from 0.01 to 25 weight ^_0/0, and Okutenirukohaku San'ori Contains 19-96 mass% of water-soluble substance consisting of powder and dextrin. By putting this solid composition in water, the liquid composition before drying can be reproduced.

[0014] In the Coenzyme Q-containing liquid composition of the present invention, dispersed and emulsified Coenzyme Q

Ten

Dispersion containing particles, specifically Coenzyme Q 'The average particle size of the emulsified particles is 3 μm

10 10

Below, it is preferably 1 μm or less, more preferably 0.8 μm or less. The average particle size at the time of water dispersion is stably maintained when the liquid composition is stored for a long time.

[0015] Further, it is obtained by resuspending or dissolving a solid composition containing Coenzyme Q in an aqueous liquid.

Ten

Similarly, the average particle size of Coenzyme Q emulsified particles in the liquid composition

Ten

1 μm or less, more preferably 0.8 μm or less. This is the same whether the liquid composition is dried as it is or adsorbed or supported on a carrier. The average particle size is maintained stably even when the solid composition is stored for a long period of time and re-dissolved and re-dispersed in an aqueous liquid.

[0016] The content of Coenzyme Q in the composition of the present invention depends on the desired intake amount and the form of the composition.

Ten

The force that is appropriately determined according to the case of liquid. The range is 0.001 to 50% by mass, preferably 0.01 to about LO mass%. Further, when it is solid, for example, powder or granule, it is generally in the range of 0.01 to 80% by mass, preferably 0.5 to 60% by mass, for example about 50% by mass. The daily intake of Coenzyme Q is the age

Ten

The strength varies depending on body weight and health condition. Usually, it is 5 to 600 mgZ days, preferably 10 to 3 OOmgZ days for adults.

[0017] Dispersion of Coenzyme Q 'Water-soluble substances used in emulsification act as protective colloids

Ten

Then, Kokonzym Q is dispersed and emulsified as uniform and fine particles to reduce the emulsion.

Ten

It is to keep it constant. Examples of water-soluble substances include gum arabic, starch, gelatin, xanthan gum, casein, carmellose sodium (CMC sodium), guar gum, pullulan, carrageenan, polybulurpyrrolidone (PVP), polybulualcohol (PVA), and carboxyvinore polymer. And water-soluble polysaccharides derived from plants such as methinoresenorelose, ethinoresenorelose, hydroxypropenoresenorose, or bectin. However, in order to obtain a stable emulsion containing uniform and fine Coenzyme Q particles,

Ten

The combination of succinate starch and dextrin is optimal. [0018] Examples of the raw material starch of otaturucuccinic acid starch include starches such as tapio force starch, potato starch, corn starch, potato starch, rice starch, and wheat starch. Examples of dextrin include the aforementioned starch hydrolyzate and maltodextrin.

[0019] In the present invention, the content of the water-soluble substance, which is also otaturuccinate starch and dextrin, in the composition containing Koenzyme Q is the form of the composition (liquid or solid), Koenza

Ten

It depends on the content of im Q. In the case of liquid compositions, based on the weight of the composition, 4 to

Ten

The range is 30% by mass, preferably 10 to 20% by mass. Moreover, when it is a solid composition, it is the range of 19-96 mass%, Preferably it is 30-90 mass%. In addition, the mixing ratio of otaturuccinic acid starch and dextrin in the water-soluble substance is in the range of 5 to 95:95 to 5, preferably in the range of 25 to 80:75 to 20. Otaturkono, succinate starch and dextrin blending ratios outside this range will reduce the effectiveness of the combination of the two, resulting in a uniform, fine, stable emerald, that is, containing the desired coenzyme Q. A composition cannot be obtained.

Ten

[0020] Examples of the polyhydric alcohol include propylene glycol, polyethylene glycol, sugar alcohols (eg, sorbitol, erythritol, mannitol, xylitol, etc.), sugars such as glucose, fructose, sucrose, and maltose. And fine coenzyme Q

The most suitable for obtaining stable emulsions containing 10 are sorbitol and propylene glycol. Sufficient effects can be obtained by using sorbitol and propylene glycol for foods that use only pharmaceutical sorbitol and propylene glycol. These sorbitol and propylene glycol are usually used separately. These two types of polyhydric alcohols may be used in combination. The content of sorbitol, propylene glycol, or a mixture thereof depends on the form of the composition (liquid or solid), the content of Coenzyme Q, etc.

Ten

It is the range of 10 mass%, Preferably it is 0.5-5 mass%. In the case of a solid composition, it is in the range of 0.01 to 25% by mass, preferably 0.1 to 10% by mass.

In the present invention, in order to obtain a desired Coenzyme Q-containing composition,

Ten

Dispersion of Q Q's water-soluble substance consisting of octenyl succinate starch and dextrin And a combination of sorbitol and z or propylene glycol components. If one of these components is deleted or replaced with another component, the desired emulsion containing Coenzyme Q that is uniform, fine and stable in force can be obtained.

Ten

Or problems with storage stability of emulsion particles and Coenzyme Q absorption

Ten

There is a possibility of twisting.

[0022] When Coenzyme Q of the present invention is dispersed and emulsified, octenylcoha is used as a water-soluble substance.

Ten

Although succinate starch and dextrin are used, other water-soluble substances such as gum arabic may be added as long as the effects thereof are not hindered.

[0023] In producing the composition containing Coenzyme Q of the present invention, Coenzyme Q is treated with water.

10 10 Dispersed in liquid 'Before or after emulsification, to stabilize Coenzyme Q,

Ten

In addition, organic acids can be added to the aqueous liquid. Examples of organic acids include, for example, succinic acid, succinic acid, fumaric acid, lactic acid, darconic acid, malic acid, tartaric acid and salts thereof, preferably citrate, malic acid, tartaric acid or salts thereof or mixtures thereof. It is. Examples of the organic acid salt include sodium salt, potassium salt, magnesium salt, calcium salt and the like. The amount of organic acid added varies depending on the type of organic acid, but is generally in the range of 0.01 to 30% by mass, preferably 0.05 to 15% by mass, based on the mass of the liquid composition.

[0024] Therefore, when the organic acid is added, the liquid composition is Coenzyme Q 1-50 mass.

Ten

%, Sorbitol and Z or propylene glycol 0.01 to 10% by weight, water-soluble substance 4 to 30% by weight, organic acid 0.01 to 10% by weight and water 40 to 94% by weight. The solid composition with organic acid added is Coenzyme Q 3-80% by weight, sorbitol

Ten

Le and Z or propylene glycol from 0.01 to 25 weight ^_0/0, containing a water-soluble substance 19 to 96 mass% and 0.01 to 30 wt% organic acid. The composition added with the organic acid can be diluted or concentrated as it is to be used as a food material, cosmetic material or feed additive.

[0025] In the preparation of the composition containing Coenzyme Q, Coenzyme Q, which is a fat-soluble drug, is added.

10 10 Melted in advance and dispersed and emulsified in an aqueous liquid containing a specific polyhydric alcohol and a water-soluble substance to form a fine particle emulsion. For this reason, polyhydric alcohol It is preferable to prepare an aqueous solution of the water-soluble substance and preheat it. Coenzyme Q, which has been heated and melted in advance, is introduced into this aqueous solution, and then known means such as high

Ten

By using a pressure homogenizer and finely dispersing and emulsifying to a desired average particle size, a uniform and fine emulsion can be formed. These processes are performed at temperatures above the melting point of Coenzyme Q, for example about 45%.

It is preferable to carry out at 10 to 90 ° C, preferably 50 to 70 ° C. In addition, the Coenzyme Q drug substance is directly added and dispersed in an aqueous solution that has been pre-heated (about 45 to 90 ° C, preferably 50 to 70 ° C), and is dissolved in the solution, followed by emulsification.

Ten

You may let them. This method is preferable because it improves work efficiency and suppresses the loss of raw materials. Furthermore, during dispersion and emulsification of Coenzyme Q, Coenzyme Q is

10 Stabilize Coenzyme Q when preparing aqueous solutions that can be dissolved or mixed in edible oil

An organic acid may be added for the purpose of oxidation.

[0026] The specific water-soluble substance used in the present invention stably retains the fine emulsified particles of Coenzyme Q from the production of the composition of the present invention to the intake and absorption thereof.

Ten

As a result, it has the advantage of promoting uptake into the body.

[0027] When the Coenzyme Q-containing liquid composition of the present invention is dried and solidified, food and

Ten

Any dry / solid means commonly used in the manufacture of pharmaceutical preparations can be used. As an example, a fluidized bed that has been stirred by a fluidized bed granulation method, a stirring blade, or the like that is sprayed with the liquid composition of the present invention in a fluidized bed that is fluidized by a heated updraft as necessary. In addition to the stirring granulation method in which the liquid composition of the present invention is added dropwise or by spraying, freeze drying and the like are exemplified.

[0028] The liquid composition of the present invention can be solidified, for example, powdered, by subjecting it to a drying 'solidifying means such as spray drying, spray cooling, freeze drying, etc., without adding a carrier. A good solid composition capable of forming a fine and stable aqueous composition when dissolved or dispersed in an aqueous liquid can be obtained. If necessary, it may be adsorbed or supported on a carrier and solidified, for example, powdered. In this case, any ingestible carrier capable of adsorbing or supporting the liquid composition can be used. For example, microcrystalline cellulose, / 3-cyclodextrin, casein or a salt thereof, gelatin, dextrin, Various starches (eg, partially alpha starch, modified starch, etc.), gum arabic, Iryum seed gum, pectin, xanthan gum, guar gum, agar, pullulan and other plant gums, hydroxypropylcellulose (HPC), sugars (glucose, fructose, sucrose, lactose, reduced maltose, etc.), silicon dioxide, sugar alcohol (For example, glycerin, erythritol, mannitol, xylitol, etc.). In addition, the functionality and characteristics of the solid preparation to be obtained can be changed by appropriately selecting the carrier. For example, when dextrin or mannitol is used as a carrier, the Coenzyme Q-containing composition of the present invention or the

Ten

The water solubility of the food containing this can be further increased. On the other hand, when lactose or crystalline cellulose is used, a directly compressible composition having plastic deformability or a food containing the same can be obtained, such as a wearable tablet, a tablet, a dissolving tablet upon use, an effervescent tablet, etc. Can also be prepared as appropriate.

[0029] The amount of carrier in the solid composition is Coenzyme Q, sorbitol and

It is in the range of 10 to 800 parts by mass with respect to 100 parts by mass of the total mass of 10 Z or propylene glycol, the water-soluble substance and the organic acid used as necessary.

[0030] When a product such as food, cosmetics or feed is produced by blending the composition of the present invention, vitamins or the like can be suitably blended. Water-soluble vitamins include vitamin B group and vitamin C. Vitamin B group includes vitamin B derivatives, vitamin B, vitamin B

1 2

, Vitamin B, Vitamin B, and Piotin, Pantothenic acid, Nicotinic acid, Folic acid, etc.

6 12 13

Species vitamin B complex is included. Vitamin B derivatives include thiamine or its salts,

1

Physiological activity of vitamin B such as amine disulfide, fursultiamine or its salt, dicetiamine, bisbuthiamine, bisbenchamine, benfotiamine, thiamine monophosphate disulfide, sicothiamine, octothiamine, prosultiamine All chemistry with

1

Compounds are included. Examples of fat-soluble vitamins include vitamin E, vitamin D or derivatives thereof, vitamin K, vitamin K, vitamin Α, and β-carotene.

1 2

[0031] In the present invention, the amount of vitamins to be blended is appropriately determined according to the type, the form of the final product to be produced, and the amount of intake to be desired, but in the case of powder, granules, etc. The range is 0.001 to 30% by mass, preferably 0.01 to 10% by mass, for example, about 1% by mass. In the case of liquids and beverages, the range is 0.0001 to 10% by mass, preferably about 0.001 to 3% by mass. [0032] When various products are produced by blending the composition of the present invention, further minerals such as calcium, potassium, iron, zinc and yeast or their contents, L-carcin, creatine, a-lipoic acid , Glutathione, Glucuronic acid, Taurine, Collagen, Soy isoflavone, Lecithin, Peptide, Amino acids, γ-Aminobutyric acid, Diacylglycerol, DHA, EPA, Medium chain fatty acid triglyceride, Edible oils and fats, Kabusaicin, Chondroitin sulfate, Agaritas Extract, carrot extract, garlic extract, glucan, green juice, royal jelly, propolis, octacosanol, NADH, D-lipose, ceramide, hyaluronic acid, flavanjenol, pycnogenol, ma force, chitosan, garcinia extract, chondroitin, darcosamine, Caseinu Naturiu , Casein Kano Residencial © beam, adding nutrients or nutritional food material such as milk proteins such as casein magnesium 'may be added. In addition, flavor components such as sugar, protein, lipid, dietary fiber, sweetener, flavor, fruit juice, and other flavor components such as coffee flavor, matcha flavor, and milk flavor may be added and blended as appropriate.

[0033] As other ingredients, it is possible to add herbs such as yew leaf extract, grape seed extract, paralian extract, and herbal medicines such as ginseng, etc., such as Tochu tea, oolong tea, green tea, You may mix | blend black tea, nono, toggi tea, etc.

[0034] The form of the food containing the composition of the present invention includes functionalities such as tablets, tablet confectionery, chewable tablets, powders, capsules, granules, enteral nutrients, liquid foods such as enteral nutrients, and drinks. Food or nutritional supplements, tea drinks such as green tea, oolong tea and black tea, soft drinks, jelly drinks, sports drinks, milk drinks, carbonated drinks, fruit juice drinks, lactic acid bacteria drinks, fermented milk drinks, powdered drinks, cocoa drinks, refined drinks Beverages such as water, butter, mayonnaise, shortening, margarine, custard cream, dressings, breads, cooked rice, rice cakes, miso soup, tofu, milk, pasta, soups or sauces, confectionery such as biscuits and cookies, Examples include chocolate, candies, cakes, ice cream, chewing gum, tablets, and yogurt. The food of the present invention includes other food materials used in the production thereof, various nutrients, various vitamins, minerals, dietary fiber, various additives, such as taste ingredients, sweeteners, acidulants such as organic acids, stable It can be produced according to a conventional method by blending agents, flavors and the like.

[0035] Furthermore, animal feed such as livestock feed or pet food can be produced using the composition of the present invention as feed raw material or material, and can be ingested by animals such as livestock or pets. . Furthermore, the composition of the present invention can be applied to cosmetics such as creams, emulsions, lotions, lipsticks or lip balms as it is or in the same manner as pharmaceuticals.

[0036] Foods and feeds containing the composition of the present invention can efficiently ingest Coenzyme Q.

Ten

It can be taken easily and reliably anytime and anywhere. Also includes Coenzyme Q

10 Because the composition is easily soluble in water and excellent in taste, it is easy to take even for people who have difficulty swallowing the elderly as a food.

EXAMPLES Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to these examples.

Example

[0037] [Example 1]

Otaturus succinic acid powdered sodium (Matsuya Igaku Kogyo) 800g, dextrin (Matsutani Igaku Kogyo) 300g and sorbitol (Nikko Chemical) lOOg are added to purified water 4000g and heated to about 60 ° C. Add 800 g of Coenzyme Q (manufactured by Nisshin Faluma) and mix.

Ten

Further, it was passed through a high-pressure homogenizer (processing pressure 700 kgZcm ² , 3 times) to obtain a fine and uniform emmanent region.

The particle size of the dispersed emulsified particles containing Coenzyme Q in this emulsion is measured with the laser.

Ten

The 50% particle size was 0.31 μm when measured using a one-diffractive scattering type particle size distribution analyzer (MICROTRAC FRA; manufactured by Nikkiso Co., Ltd.).

Next, this emulsion was ejected into a hot air stream heated to 140 ° C. to remove water, and an orange powder composition containing 40% by mass of Coenzyme Q was obtained.

Ten

[0038] [Example 2]

Otaturosuccinic acid disintegrated sodium (Matsuya Igaku Kogyo) 800g, Dextrin (Matsutani Igaku Kogyo) 300g, Sorbitol (Niken Igaku) 60g and Malic acid 40g in about 4000g of purified water Heat to ° C. Coenzyme Q (manufactured by Nisshin Faluma) with 800g

Ten

The mixture was then mixed and further passed through a high-pressure homogenizer (processing pressure 700 kgZcm ² , 3 times) to obtain a fine and uniform emulsion.

The particle size of the dispersed emulsified particles containing Coenzyme Q in this emulsion is shown in Example 1.

Ten

When measured in the same manner, the 50% particle size was 0.41 μm. Next, from this emulsion, 40% by mass of Coenzyme Q was obtained in the same manner as in Example 1.

Ten

An orange powder composition was obtained.

[0039] [Example 3]

Otaturus succinic acid powdered sodium (Matsuya Chemical Co., Ltd.) 240g, dextrin (Matsutani Chemical Co., Ltd.) 120g and sorbitol (Niken Chemical Co., Ltd.) 24g are added to purified water 1200g and heated to about 60 ° C. Coenzyme Q (Nisshin Fualma) 416g was added to this and mixed.

Ten

When measured in the same manner, the 50% particle size was 0.39 Hm.

Next, from this emulsion, in the same manner as in Example 1, 52% by mass of Coenzyme Q was obtained.

Ten

An orange powder composition was obtained.

[0040] [Example 4]

Otaturus succinic acid disintegrated sodium (Matsuya Chemical Industry) 240g, dextrin (Matsuya Chemical Industry 80g), gum arabic (Ina Food Industry) 40g and sorbitol (Niken Chemical) 24g are added to purified water 1200g, approx. 60 ° Heat to C. Cohenzym Q (Nisshin Fu

10 Alma) 416 g was added and mixed, and further passed through a high-pressure homogenizer (treatment pressure 700 kgZcm 3 times) to obtain a fine and uniform emulsion.

Ten

When measured in the same manner, the 50% particle size was 0.48 m.

Ten

An orange powder composition was obtained.

[0041] [Example 5]

Otaturosuccinic acid disintegrated sodium (Matsuya Chemical Industry Co., Ltd.) 240g, dextrin (Matsutani Chemical Industry Co., Ltd.) 104g, Sorbitol (Niken Igaku Co., Ltd.) 24g and malic acid 16g in power of 1200g purified water! ] Warm up to about 60 ° C. Coenzyme Q (Nisshin Fualma) 416g

Ten

The mixture was then mixed and further passed through a high-pressure homogenizer (processing pressure 700 kgZcm ² , 3 times) to obtain a fine and uniform emulsion. The particle size of the dispersed emulsified particles containing Coenzyme Q in this emulsion is shown in Example 1.

Ten

When measured in the same manner, the 50% particle size was 0.44 m.

Ten

An orange powder composition was obtained.

[0042] [Example 6]

Otaturosuccinic acid disintegrated sodium (Matsuya Chemical Co., Ltd.) 240g, dextrin (Matsutani Chemical Industry Co., Ltd.) 100g, propylene glycol (Asahi Glass Co., Ltd.) 30g and malic acid 14g purified water 12 OOg, heated to about 60 ° C To do. Coenzyme Q (Nisshin Fualma) 416g

Ten

The mixture was added and mixed, and further passed through a high-pressure homogenizer (treatment pressure 700 kgZcm ² , 3 times) to obtain a fine and uniform emulsion.

Ten

When measured in the same manner, the 50% particle size was 0.51 μm.

Ten

An orange powder composition was obtained.

[0043] [Example 7]

400 g of the emulsion obtained in Example 5 was powdered in a fluidized bed using 2400 g of dextrin (manufactured by Sanwa Starch) as a carrier to obtain an orange-yellow powder to a granular powder composition.

[0044] [Example 8]

400 g of the emulsion obtained in Example 5 was powdered in a fluidized bed using 1800 g of dextrin (manufactured by Sanwa Starch) and 600 g of sorbitol (manufactured by Nikken Kasei) as a carrier. A powder composition was obtained.

[0045] [Comparative Example 1]

Add 800g of Otatur Succinic acid powder (Matsuya Igaku Kogyo) and 400g of dextrin (Matsutani Igaku Kogyo) to 4000g of purified water, and heat to about 60 ° C. This is Coenzym Q

1

(Manufactured by Nisshin Faluma) Add 800 g and mix, and then add high pressure homogenizer (processing pressure 70

0

3 times) to obtain a fine and uniform emulsion.

Ten

When measured in the same manner, the 50% particle size was 0.33 μm. Next, the emulsion was ejected into a hot air stream heated to 140 ° C. to remove water, and an orange powder composition (solid preparation) containing 40% by mass of Coenzyme Q was obtained.

Ten

[0046] [Comparative Example 2]

Add 240g of Otatur Succinic Acid Powder (Matsuya Chemical Co., Ltd.) and 144g of Dextrin (Matsutani Chemical Co., Ltd.) to 1200g of purified water, and heat to about 60 ° C. This is Coenzym Q

1

(Nisshin Faluma) 416g was added and mixed, and then a high-pressure homogenizer (processing pressure 70)

0

3 times) to obtain a fine and uniform emulsion.

Ten

When measured in the same manner, the 50% particle size was 0.39 Hm.

Next, from this emulsion, Coenzyme Q was 52% by mass in the same manner as in Comparative Example 1.

Ten

An orange powder composition was obtained.

[0047] [Comparative Example 3]

Add 240g of Otatur Succinic acid powder (Matsuya Chemical Co., Ltd.) and 240g of dextrin (Matsutani Chemical Co., Ltd.) to 1200g of purified water, and heat to about 60 ° C. Coenzyme Q (manufactured by Nisshin Faluma) 320 g was added to this and mixed, and then a high-pressure homogenizer (processing pressure 70)

0

3 times) to obtain a fine and uniform emulsion.

Ten

When measured in the same manner, the 50% particle size was 0.45 m.

Next, from this emulsion, 40% by mass of Coenzyme Q was conducted in the same manner as in Comparative Example 1.

Ten

An orange powder composition was obtained.

[0048] [Comparative Example 4]

Sodium otaturuccinate starch (made by Matsutani Chemical Co., Ltd.) 800g, sorbitol (manufactured by Nikken Chemical Co., Ltd.) 360g and malic acid 40g were put into 4000g of purified water, about 60. Caro warm to C. Add 800 g of Coenzyme Q (Nisshin Faluma), mix, and further homogenize with high pressure.

Ten

1 (treatment pressure 700 kgZcm ² , 3 times) to obtain fine and uniform emulsion. The particle size of dispersed emulsified particles containing Coenzyme Q in this emulsion is shown in Example 1.

Ten

When measured in the same manner, the 50% particle size was 0.55 μm. Next, from this emulsion, 40% by mass of Coenzyme Q was conducted in the same manner as in Comparative Example 1.

Ten

An orange powder composition was obtained.

[0049] [Comparative Example 5]

Sodium otaturuccinate starch (manufactured by Matsutani Chemical Co., Ltd.) 800g, propylene glycol (manufactured by Asahi Glass) 360g and malic acid 40g are added to purified water 4000g and heated to about 60 ° C. Add 800g of Kokonzym Q (Nisshin Faluma), mix and add to high-pressure homogen

Ten

A finer and uniform emulsion was obtained by passing through a nizer (processing pressure 700 kgZcm ² , 3 times).

Ten

When measured in the same manner, the 50% particle size was 0.53 Hm.

Ten

An orange powder composition was obtained.

[0050] [Comparative Example 6]

Otaturosuccinic acid powdered sodium (Matsutani Chemical Co., Ltd.) I40g, dextrin (Matsutani Chemical Co., Ltd.) 200g, lactose (DMV Co., Ltd.) 140g is added to purified water 1400g and heated to about 60 ° C. Coenzyme Q (Nisshin Faluma) (320 g) was added to this and mixed.

Ten

A fine and uniform emulsion was obtained by passing through a homogenizer (treatment pressure 700 kgZcm ² , 3 times).

Ten

When measured in the same manner, the 50% particle size was 0.63 Hm.

Ten

An orange powder composition was obtained.

[0051] [Comparative Example 7]

Add 800 g of gum arabic (manufactured by Ina Food Industry), 340 g of dextrin (manufactured by Matsutani Chemical Co., Ltd.) and 60 g of glycerin to 4000 g of purified water, and heat to about 60 ° C. This is Coenzym Q

Ten

3 times) to obtain a fine and uniform emulsion.

The particle size of the dispersed emulsified particles containing Coenzyme Q in this emulsion is shown in Example 1. When measured in the same manner, the 50% particle size was 0.64 m.

Ten

An orange powder composition was obtained.

[0052] [Comparative Example 8]

Add 690 g of dextrin (Matsuya Chemical Co., Ltd.), 50 g of lecithin, 400 g of soybean oil, and 60 g of glycerin to 4000 g of purified water, and heat to about 60 ° C. Coenzyme Q (Nisshin Faar

Ten

800 g was added and mixed, and further passed through a high-pressure homogenizer (processing pressure 700 kgZcm ² , 3 times) to obtain a uniform emulsion.

Ten

When measured in the same manner, the 50% particle size was 0.72 m.

Ten

An orange powder composition was obtained. However, there were problems in terms of workability such as stickiness of oily components during spray drying of the emulsion, and the efficiency was not satisfactory.

[0053] [Comparative Example 9]

= 3--starch 740g, dextrin 400g and glycerin 60g are added to purified water 4000g and heated to about 60 ° C. Add 800 g of Coenzyme Q (Nisshin Faluma)

Ten

After mixing, the mixture was further passed through a high-pressure homogenizer (processing pressure 700 kgZcm ² , 3 times). However, immediately after the treatment, the force that formed the emulsion was separated immediately, and it was impossible to maintain a uniform emulsion.

[0054] [Comparative Example 10]

Dextrin (Matsutani Chemical Industry Co., Ltd.) 740g, sodium caseinate 400g, glycerin 60g, 4,000g of purified water, heat to about 60 ° C. Coenzyme Q (Nisshin Fualma)

Ten

800 g was added and mixed, and further passed through a high-pressure homogenizer (processing pressure 700 kgZcm ² , 3 times) to obtain a fine and uniform emulsion.

Ten

When measured in the same manner, the 50% particle size was 0.75 m.

Next, from this emulsion, 40% by mass of Coenzyme Q was conducted in the same manner as in Comparative Example 1. An orange powder composition was obtained.

[0055] [Comparative Example 11]

Add 800 g of dextrin (Matsuya Igaku Kogyo) and 400 g of sorbitol (Nikken Igaku) to 4 OOOg of purified water, and heat to about 60 ° C. Coenzyme Q (Nisshin Fualma) 800g

Ten

Were added and mixed, and further passed through a high-pressure homogenizer (processing pressure 700 kgZcm ² , 3 times) to obtain a fine and uniform emulsion.

Ten

When measured in the same manner, the 50% particle size was 0.49 m.

Ten

An orange powder composition (solid preparation) was obtained.

[0056] Test Example 1 Emulsion stability test

Examples 1 to 3 and 6 and Comparative Examples 1 to 5 and 11 Coenzyme Q-containing compositions 1

Ten

The dispersion was dispersed in OOmL, and the average particle size of the dispersion was measured using a laser diffraction / scattering particle size distribution measuring apparatus (MICROTRAC FRA; manufactured by Nikkiso Co., Ltd.). Also, the ease of dispersion in water was visually observed and evaluated. The results obtained are shown in Table 1 below. The average particle size m) is evaluated in the upper part, and the ease of dispersion is evaluated according to the following criteria, and the results are shown in the lower part.

: Disperses well

+: Dispersion takes time

+ +: Dispersion takes considerable time

(40 ° C glass bottle packaging)

[0057] [Table 1]

table 1

From the results shown in Table 1, in Examples 1 to 3 and 6 containing a combination of otaturuccinate starch and dextrin, and sorbitol and Z or propylene glycol, Comparative Examples 1 to 5 in which one of these combinations was replaced with another component The water dispersibility is very good compared to 11 In addition, the dispersion state was maintained well even during long-term storage. Furthermore, in the above Examples, the average particle size during water dispersion was maintained well during long-term storage. On the other hand, in Comparative Examples 1 to 5 and 11, an increase in the average particle size during water dispersion was observed during long-term storage, precipitation also occurred during storage for 6 weeks, and water dispersibility after long-term storage may be problematic. Indicated.

From the above, the composition of the present invention contains a high content of Coenzyme Q.

Ten

Regardless, it was confirmed that even after long-term storage, the water dispersibility was extremely excellent, and the average particle size at the time of water dispersion was also stably maintained.

[0059] Test Example 2 Coenzyme Q Stability Test

Ten

Residual rate of Coenzyme Q for each of the yarns of Examples 1 to 3 and Comparative Examples 1 and 2

10 measured. The results are shown in Table 2.

1) Storage conditions

Storage temperature 50 ° C, Glass bottle airtight container, 0 ~ 6 weeks storage

2) Measuring method It implemented on the following conditions using HPLC.

Detector; UV absorption photometer (measurement wavelength: 275nm)

Column; Hypersil ODS— 5 4.6mm X 15cm

Mobile phase: methanol Z absolute ethanol (13: 7)

50 ° C glass bottle packaging (starting rate is 100%, remaining rate%)

[0060] [Table 2]

Table 2

From the results of Table 2, in Examples:! To 3, Coenzyme Q in the composition was stably retained with little decomposition even during long-term storage. On the other hand, in Comparative Examples 1 and 2, 4 after storage The remaining rate of Coenzyme Q starts to decrease from week, and after six weeks, Coenzyme Q

10 10 About 10% was lost, indicating a problem with storage stability. In view of these facts, the composition of the present invention has a high content of coenzyme Q, although it contains a high content of coenzyme Q.

Ten

It was confirmed that the storage stability of Nzyme Q is remarkably excellent.

Ten

Test Example 3 Absorbency test

The powder containing Coenzyme Q obtained in Example 1 and Comparative Example 2 was used as a node capsule.

Ten

Filled and tested for absorbency. Specifically, each group of 3 (male) beagle dogs was given a single dose of 90 mg Zdog as Coenzyme Q. After administration

Ten

Blood is collected at regular intervals up to 24 hours to estimate the Coenzyme Q concentration in plasma over time.

Ten

Investigated the transfer. The beagle dogs were fasted after 5 pm the previous day, and only water was ingested. On the day of the test, capsules were forcibly administered together with 10 mL of water without feeding in the morning.

Coenzyme Q was measured using HPLC under the following conditions. There is acid in the serum.

Ten

Since there is a type and reduced type Coenzyme Q, the total of both was calculated.

Ten

Column: Nucleosil 5C18 4.6mm water 25cm

Mobile phase: Ethanol: Acetonitrile (55:45)

'. lmL, mm

Detector: UV spectrophotometer 275nm

Temperature: 35 ° C

Injection volume: 5; z L

From the obtained Coenzyme Q blood concentration, the highest blood pharmacokinetic parameter was obtained.

Ten

The concentration, the time to reach the maximum blood, and the area under the blood concentration one hour curve were determined.

. The results are shown in Table 3 below.

[Table 3] _ 3

(Mean soil S. D)

Cmax (y g / rnl) Maximum blood level

tmax (hr) Time to reach maximum blood

AUC (0 → t) (g / hr / ml) Area under the blood one hour curve

[0063] As a result of these absorbability tests, the composition of Example 1 was more reliable than the composition of Comparative Example 2 in terms of the plasma concentration of Coenzyme Q even when administered orally under fasting. High concentration

Ten

It was confirmed that Coenzyme Q was absorbed into the body. From these, the present invention

Ten

It has been clarified that this composition is remarkably excellent in noavailability.

[0064] [Example 9]

430 g of soybean oil (manufactured by Yoshihara Seisakusho) and 20 g of glycerin fatty acid ester (manufactured by Riken Vitamin) were mixed, heated to about 65 ° C and dissolved. Thereafter, the mixture was cooled to room temperature, and 50 g of the powder composition 150 of Example 2 was added and stirred to prepare a filling liquid. Using this filling solution, 300 mg of soft capsules per capsule were prepared by a conventional soft capsule manufacturing method. This capsule contained 30 mg of Coenzyme Q.

Ten

[Example 10]

L-Carthine L-Tartrate 100g, Crystalline cellulose (Asahi Kasei) 260g, Lactose (DM V) 80g, HPC (Nippon Soda) (hydroxypropylcellulose) 10g are mixed and kneaded with 80mL of ethanol. Knead for 5 minutes using the usual method. After kneading, sieve through 10 mesh and dry at 50 ° C in a dryer. After drying, the particles were sized to obtain granules. To this condylar granule, 150 g of the powder composition of Example 2 was added and mixed to produce a granule containing Coenzyme Q.

Ten

I got a product. This granule is packaged in a stick of 1.2g / pack, and Coenzyme Q in one stick

A granule containing 120 mg of 10 was obtained.

[Example 11]

Chengic acid (manufactured by Tanabe Seiyaku) 1.0g, glucose solution (manufactured by Nippon Food Processing Industry) 200g, purified water 64 The mixture was dissolved in 9 g with stirring at room temperature, and adjusted to pH 3.0 to 3.5. Thereto, 150 g of the powder composition of Example 2 was added and dissolved to obtain a uniform beverage composition containing Coenzyme Q.

Ten

[0067] [Example 12]

225 g of the powder composition of Example 2, 15 g of vitamin B, 30 g of L-carthine L-tartrate,

1

390 g of crystalline cellulose (manufactured by Asahi Kasei), 230 g of lactose 200M (manufactured by DMV), and 10 g of kenic acid (manufactured by Tanabe Seiyaku) were sieved with 16 mesh to obtain a powder. Fill this powder into a No. 2 node capsule with about 300 mg per capsule (containing 30 mg of Coenzyme Q per l capsule).

Ten

Nzyme Q

A 10-containing capsule was obtained.

[Example 13]

Mix 120g of flour (strong flour) and 2g of dry yeast. In addition, 2.5 g of powder composition of Example 2, 20 g of sugar, 3 g of salt, and 6 g of skim milk powder are dissolved in 70 g of hot water, add 1 egg and mix well, 8 g of malic acid is added thereto, and Mix. Add this to flour and knead well by hand, then add about 40 g of butter and knead well to make 20 rolls. Next, after fermenting, the egg was coated on the surface and baked in an oven at 180 ° C for about 12 minutes to produce a roll. This bread roll contained about 50 mg of Coenzyme Q per piece.

Ten

[0069] [Example 14]

1.5 g of the powder composition of Example 2 was dissolved in 1 L of oolong tea to obtain a beverage. About 100mg of coenzyme Q was contained per 100m.

Ten

Industrial applicability

[0070] According to the present invention, even without using a synthetic emulsifier such as glycerin fatty acid ester, the coenzyme Q is contained in a high content, and the stability and bioavailability of coenzyme Q are improved.

10 10

Coenzyme Q, which is excellent in terms of re-tability (absorbability, bioavailability, etc.)

10 containing compositions are provided. The liquid composition of the present invention is Coenzyme Q

Despite the high content of 10, good emulsification is maintained even after long-term storage. In addition, even when the solid composition of the present invention is stored for a long period of time, the solubility or dispersibility in an aqueous liquid such as water does not deteriorate, and a fine and stable aqueous composition can be formed by adding to the aqueous liquid. It is suitable. These compositions have the characteristic that Coenzyme Q is reliably absorbed even on an empty stomach.

Ten

To do. For this reason, the composition of the present invention is added to various forms of food and drink, cosmetics and feed. Caro 'can be formulated, and Coenzyme Q's high bioavailability is achieved.

Ten

The

Claims

The scope of the claims

[1] Coenzyme Q is a water-soluble substance that also contains octenyl succinate starch and dextrin.

Ten

Dispersed in an aqueous liquid containing sorbitol and z or propylene glycol

• Coenzyme Q 1-50% by weight, sorbitol and emulsified

10 Z or profile propylene glycol 0.01 to 10 mass ^_0/0, the water-soluble substance 4 to 30 weight ^_0/0 and water 40-94 Koenzaimu Q-containing liquid composition containing mass%.

Ten

[2] Coenzyme Q is a water-soluble substance that also contains octenyl succinate starch and dextrin.

Ten

Dispersed in an aqueous liquid containing sorbitol and z or propylene glycol

'Emulsified, Koenzaimu Q 1 to 50 weight ^_0/0, sorbitol and Z or propylene grayed

Ten

Coenzyme Q containing liquid composition containing 0.01 to 10% by weight of water, 4 to 30% by weight of water-soluble substance and 40 to 94% by weight of water, and obtained by drying this

Ten

Q

10 containing solid composition.

[3] Koenzaimu Q 3 to 80 weight ^_0/0, sorbitol and Z or propylene glycol

Ten

0.01 to 25 weight ^_0/0, and Otatenirukohaku acid starch and dextrin mosquitoes also water-soluble substance 19 to 96 Koenzaimu Q-containing solid composition of claim 2 containing mass%.

Ten

[4] The Koenzaimu Q 1 to 50 weight ^_0/0, sorbitol and

10 Z or propylene glycol 0.01 to 10% by weight, consisting of dispersing and emulsifying in an aqueous liquid containing 4 to 30% by weight of a water-soluble substance that also becomes octenyl succinate starch and dextrin and 40 to 94% by weight of water, A method for producing a liquid composition containing Coenzyme Q.

Ten

[5] The Koenzaimu Q 1 to 50 weight ^_0/0, sorbitol and Z or propylene glycol

Ten

Disperse and emulsify in an aqueous liquid containing 0.01 to 10% by mass of water-soluble substance 4 to 30% by mass of octenyl succinate starch and dextrin and 40 to 94% by mass of water to obtain a zyme Q-containing liquid composition Cohenzyme Q content, consisting of drying this

10 10 A method for producing a solid composition.

[6] Koenzaimu Q-containing solid composition, Koenzaimu Q 3 to 80 weight ^_0/0, sorbitol

10 10

And Z or method according to claim 5 Propylene glycol 0.01 to 25 weight ^_0/0, and containing a water-soluble substance 19 to 96% by weight consisting of Otateyurukohaku acid starch and dextrin. [7] A food, cosmetic or feed comprising the composition according to any one of claims 1 to 3.