JP2012077087A - Clathrate compound of stable astaxanthin with gamma-cyclodextrin, and food and drink, feed and medication including the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a clathrate compound of stable astaxanthin and/or ester thereof with γ-cyclodextrin; and to provide a liquid formulation, food and drink, feed, medication and cosmetic including the clathrate compound.SOLUTION: There is provided a clathrate compound method of stable astaxanthin and/or ester thereof with γ-cyclodextrin characterized by blending γ-cyclorextrin to astaxanthin and/or ester thereof at a ratio of 1:50 to 1:100. A liquid formulation, food and drink, feed, medication and cosmetic including the clathrate compound are also provided.

Description

  The present invention comprises a stable inclusion compound of astaxanthin and γ-cyclodextrin, characterized in that γ-cyclodextrin is blended at a specific ratio with astaxanthin, and a method for producing the same, and the inclusion compound The present invention relates to the use of liquids, foods and drinks, animal feeds, pharmaceuticals and cosmetics.

  Astaxanthin is a typical carotenoid contained in animals and plants. Red carotenoids are distributed in crustaceans such as krill, shrimp and crabs, body surface of red sea bream, salmon muscles, salmon muscles, and fish eggs such as salmon roe, yeast and algae. And is used as a color improver, a deep-fried agent, a food additive, and a cosmetic colorant for cultured seafood. Recently, it has been reported that astaxanthin has an anti-oxidant action (Nobuto Shimizu, Miki Wataru, Marine Carotenoid, Miki Wataru, Hoshiseisha Koseikaku, 1993), and further to food additives, etc. Applications have also been reported. However, since astaxanthin is a fat-soluble substance like other carotenoid pigments, there is a problem that solubility in a water-soluble solvent or addition to a water-soluble compound is poor. Recently, astaxanthin has become available in large quantities and at low cost by mass culture of astaxanthin-producing Haematococcus algae. However, astaxanthin contained in naturally derived extracts such as Haematococcus, astaxanthin free form, astaxanthin fatty acid monoester and astaxanthin fatty acid diester, in addition to impurities, glycerides such as monoglyceride, diglyceride and triglyceride, free fatty acid, or Since the ester derived from the free fatty acid is included, there is a problem that even when powdered by the conventional method, the red color of astaxanthin is faded at room temperature and the commercial value is lowered. For example, (1) JP-A-9-124470 discloses astaxanthin and / or an ester thereof as cyclo (cyclic) dextrin (α-cyclodextrin). , Β-cyclodextrin, γ-cyclodextrin) can be used to obtain a water-soluble powdered inclusion compound, (2) JP-A-10-155459 discloses astaxanthin ethyl Ester-containing drinks, nourishing tonics, and (3) Japanese Patent Application Laid-Open No. 2001-2569 include a cyclo (cyclic) dextrin (α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin). It is described that a powdery clathrate soluble in water can be obtained. However, a simple astaxanthin-cyclodextrin inclusion product cannot be obtained by simply mixing astaxanthin and cyclodextrin, and astaxanthin and γ-cyclodextrin can only be obtained by dissolving astaxanthin in ethanol and diluting with water. It was found that no inclusion compound was obtained. There is still no sufficient method for a stable inclusion compound of astaxanthin and γ-cyclodextrin and a method for producing the same, and a solution for the inclusion compound, particularly a method for obtaining a stable and clear solution by dissolving the powder.

JP-A-2-49091 Japanese Patent Laid-Open No. 2005-21098 JP 2003-64360 A

  It is an object of the present invention to provide a stable inclusion compound of astaxanthin and γ-cyclodextrin, foods and drinks, animal feeds, pharmaceuticals and cosmetics containing the inclusion compound.

  The present invention is an inclusion compound comprising astaxanthin and γ-cyclodextrin at a ratio of 0.5 to 100 parts by weight of γ-cyclodextrin with respect to 1 part by weight of astaxanthin.

  According to the present invention, a stable inclusion compound of astaxanthin and cyclodextrin could be provided. This product is easy to process and is useful for use in fields such as foods and drinks, animal feeds, pharmaceuticals, and health foods. In addition, since the inclusion compound of the present invention is easily dissolved in water and can be made into a uniform solution, it can be dissolved and used at the time of use or ingestion.

In the figure, (A) is astaxanthin (free form, synthetic product), (B) is γ-cyclodextrin, (C) is a powder obtained by kneading astaxanthin and γ-cyclodextrin at a molar ratio of 1: 3, and (D) is It is an XRD spectrum of a powder in which astaxanthin and γ-cyclodextrin are mixed at a molar ratio of 1: 3. The above (C) forms an inclusion compound. In the figure, (E) is a powder obtained by kneading astaxanthin and α-cyclodextrin at a molar ratio of 1: 3, (F) a powder obtained by mixing astaxanthin and α-cyclodextrin at a molar ratio of 1: 3, and (G) is an astaxanthin. It is the XRD spectrum of the powder which knead | mixed (beta) -cyclodextrin by molar ratio 1: 3, and the powder which mixed (F) astaxanthin and (beta) -cyclodextrin by molar ratio 1: 3. It indicates that no inclusion compound is formed.

  In this specification, astaxanthin is composed of at least one selected from the group of astaxanthin free form, astaxanthin fatty acid monoester, and astaxanthin fatty acid diester. The fatty acid ester is composed of at least one selected from the group of saturated fatty acids or unsaturated fatty acids having 2 or more carbon atoms.

  Astaxanthin may be a synthetic product and / or a natural product, but considering the safety of the living body, a natural product such as astaxanthin extracted from Haematococcus alga, Phaffia yeast or krill is preferred, and more preferably It is an astaxanthin extracted from Haematococcus alga bodies that are industrially available in large quantities and stably.

  When using astaxanthin oil derived from Haematococcus as astaxanthin, the content of γ-cyclodextrin is based on the content of astaxanthin in the oil and the weight of other impurities (main components are mono, di, and triglycerides). Usage can be set. Specifically, it is in the range of 0.5 to 100 parts by weight of γ-cyclodextrin with respect to 1 part by weight of astaxanthin, preferably in the range of 0.5 to 50 parts by weight, more preferably in the range of 1 to 50 parts by weight. It is.

  In the present invention, in addition to the above-described γ-cyclodextrin, α-cyclodextrin, β-cyclodextrin, δ-cyclodextrin as long as the stability of the inclusion compound of astaxanthin and γ-cyclodextrin and the solubility in water are not hindered. Dextrin and a known water-soluble cyclodextrin derivative may be added.

  Examples of water-soluble cyclodextrin derivatives include hydroxypropyl-β-cyclodextrin, methyl-β-cyclodextrin, monoacetyl-β-cyclodextrin, triacetyl-β-cyclodextrin, monochlorotriazyl-β-cyclodextrin And sulfobutyl ether-β-cyclodextrin, di-O-methyl-β-cyclodextrin, maltosyl-β-cyclodextrin and the like.

  The stable inclusion compound of astaxanthin and cyclodextrin of the present invention can be produced by blending water and at least one organic solvent at a specific ratio in a mixture of astaxanthin and γ-cyclodextrin.

  The organic solvent to be used is not particularly limited as long as it dissolves astaxanthin and astaxanthin oil, but is preferably easy to remove at the final stage of pulverization, for example, alcohols such as methanol, ethanol, butanol, and propanol , At least one selected from esters such as ethyl acetate, halogenated carbon hydrogen such as dichloromethane and chloroform, acetone, ether and the like. More preferably, it is a combination of ethanol and dichloromethane or chloroform which can be included in a short time.

  Examples of the inclusion method include a kneading method, a liquid phase mixing method, a solvent evaporation method, a coprecipitation method, and a freeze drying method. A kneading method, a liquid phase mixing method, and a solvent evaporation method that are easy to handle are preferable.

  The kneading method is, for example, using a kneader, a mortar, etc., adding water and the appropriate amount of the organic solvent to a mixture of astaxanthin or astaxanthin oil and γ-cyclodextrin, and kneading and mixing until a paste is obtained. It is.

  The liquid phase mixing method is a method in which astaxanthin or astaxanthin oil and γ-cyclodextrin are added to the organic solvent and water in a container such as a flask or a reaction kettle and vigorously stirred and mixed in the aqueous phase.

  The solvent evaporation method is a method of adding the organic solvent and water to astaxanthin or a mixture of astaxanthin oil and γ-cyclodextrin, and then distilling off the solvent under reduced pressure, using an apparatus capable of reducing pressure, such as a rotary evaporator. .

  The coprecipitation method is a method in which a solution obtained by dissolving astaxanthin or astaxanthin oil in the organic solvent is dropped into an aqueous solution of γ-cyclodextrin prepared to a desired concentration while stirring.

  The freeze-drying method is a method in which the organic solvent and water are added to astaxanthin or astaxanthin oil and γ-cyclodextrin, mixed and then freeze-dried to distill off the solvent.

  In order to prevent astaxanthin from decomposing and / or fading during the production of the inclusion compound of astaxanthin and γ-cyclodextrin, the temperature range for preparing the inclusion compound is preferably 80 ° C. or less. More preferably, it is 60 degrees C or less, More preferably, it is room temperature vicinity.

  The clathrate compound obtained by the production method of the present invention can be obtained as a more stable powder when the solvent is sufficiently removed.

  In the production method of the present invention, a more stable package of astaxanthin and γ-cyclodextrin is obtained by using γ-cyclodextrin in which 0.5 to 10 parts by weight of water is previously added to 1 part by weight of γ-cyclodextrin. A contact compound is obtained.

  When the clathrate compound is prepared using astaxanthin oil, a powder having higher stability can be obtained by the following method. Specifically, in a mixture of 1 part by weight of astaxanthin contained in astaxanthin oil and 0.5 to 100 parts by weight of γ-cyclodextrin, 1 part by weight of γ-cyclodextrin, methanol, ethanol, propanol, butanol, 0.5 to 10 parts by weight of at least one organic solvent selected from the group consisting of acetone, ether, ethyl acetate, dichloromethane and chloroform and 1 to 20 parts by weight of water are added, and the resulting clathrate is added from the organic solvent. This is a method of washing with at least one organic solvent selected from the group consisting of drying, drying, washing with a small amount of water, and drying. This is probably because the trace components that affect the stability of astaxanthin are removed by washing with the organic solvent and water.

  The inclusion compound of astaxanthin and γ-cyclodextrin according to the present invention includes conventional water-soluble sweeteners, fragrances, coloring agents, starches, alginic acid in powder production as long as they do not inhibit the formation of stable inclusion compounds. Disintegrants such as soda, excipients such as lactose, glycolose, sucrose, mannitol, erythritol, binders such as hydroxypropylcellulose and gelatin, plasticizers such as glycerin, and the like can be used.

  The stable inclusion compound of astaxanthin and γ-cyclodextrin of the present invention includes butylhydridotoluene, butylhydroxyanisole, vitamin E to prevent astaxanthin and / or its ester from being oxidatively decomposed in the air. (Tocopherol and tocotrienol or derivatives thereof), ascorbic acid, L-ascorbyl palmitate, L-ascorbate stearate, sodium ascorbate, gallic acid, ethoxyquin, glutathione, phytic acid, catechins, polyphenols, Natural and synthetic antioxidants such as flavonoids, carotenoids, xanthophylls, sesame extract, rosemary extract and the like may be added.

  The uniform and transparent liquid preparation containing the inclusion compound of astaxanthin and γ-cyclodextrin according to the present invention can be obtained by dissolving the inclusion compound in water or suspending the insoluble matter after the suspension. It can prepare by filtering using.

  In the liquid preparation, surfactants, dissolution aids and the like that are usually used in preparation of the liquid preparation may be added in an amount that does not affect the solubility of the clathrate compound. Examples of the surfactant include sucrose fatty acid ester, propylene glycol ester, glycerin fatty acid ester, sorbitan fatty acid ester, dextrin, and reduced dextrin.

  When the inclusion compound of the present invention is used as a food, drink, nutritional supplement, or functional food, the form conforms to the form used in ordinary drugs, such as tablets, powders, granules, capsules. The form of a drink agent can be illustrated. In order to balance nutrition, commonly used excipients, extenders, vitamins, fibers, proteins, amino acids, minerals, animal and plant extracts, sweeteners, flavors, stabilizers, pigments Etc. can be added.

  As the form of food and drink, processed milk, cheese, butter, margarine, fresh cream, ice cream, ice confectionery, pudding, dairy products, jelly, candy, drop, rice cake, caramel, chewing gum, castella, cake, donuts, biscuits, Crackers, snacks, french fries, potato chips, popcorn, rice cakes, dumplings, daifuku, soup, sausage, ham, bacon, meat products, seaweed, chikuwa, hanpen, fish products, spaghetti, pasta, gratin, paella, curry, sauce , Ketchup, dressing, pickles, carbonated drinks, fruit juice drinks, sports drinks, tea, coffee, cocoa, beer, liqueur, cocktail, medicinal liquor, etc. Further, it can be used as a refreshing beverage as a stable, uniform and clear red liquid.

  When used as a feed, it may be used as it is, but it is used as a raw material for commonly used animal and fish feeds such as corn, milo, fish meal, bran, salt, calcium carbonate, calcium phosphate, amino acids, vitamins. , Trace minerals, existing antioxidants, etc. may be blended.

  For use as a pharmaceutical, it is orally administered in a conventional manner, for example, in solid dosage forms such as tablets and powders, or liquid dosage forms such as syrups. It can also be used parenterally, for example, as a patch, ointment, injection, or suppository. The preparation of the drug itself can be performed according to a conventional method.

  The form of the cosmetic is not particularly limited. For example, skin care cosmetics such as emulsions, creams, lotions, packs, cleaning agents, makeup cosmetics such as foundations, eye shadows, mascaras, and lipsticks, dispersions, ointments, and external use. Cosmetics such as liquids and creams can be obtained. In addition, ingredients commonly used in skin preparations such as cosmetics and pharmaceuticals, such as water (including alkaline simple hot spring water, deep water, purified water, etc.), lower alcohols, polyhydric alcohols, fats and oils, waxes, mineral oils, fatty acids , Powder, metal soap, pH adjuster, surfactant, thickener, pigment, extract derived from plant or animal materials, vitamins, amino acids, hormones, bactericidal / disinfectant, keratolytic agent, enzyme , Refreshing agents, stabilizers, metal ion chelating agents, blood circulation promoters, essential oils, deodorants, moisturizers, astringents, antiseborrheic agents, cell activators, fragrances, and the like may be added.

  The present invention will be described in detail with reference to the following reference examples, examples and comparative examples.

Reference Example 1 Preparation of astaxanthin oil from Haematococcus algae:
Hematococcus algae were cultured by a known method to obtain an astaxanthin-containing hematococcus alga body. The alga bodies were separated from the culture broth and dried, then extracted with acetone. If necessary, insolubles were removed, and then acetone was distilled off under reduced pressure with an evaporator to obtain an astaxanthin extract (hereinafter referred to as astaxanthin oil). The astaxanthin content in the astaxanthin oil was quantified by an absorbance method (measurement wavelength: 475 nm, solvent acetone). The total amount of free staxanthin, astaxanthin fatty acid monoester and astaxanthin fatty acid diester in the oil was 15% by weight based on the total amount of oil. The composition of astaxanthin in the astaxanthin oil was free astaxanthin (6% by weight), astaxanthin fatty acid monoester (82% by weight) and astaxanthin fatty acid diester (12% by weight). The other components were 50% by weight of mono-, di- and triglycerides. However, the composition of the astaxanthin oil used in the present invention and the type of fatty acid are not particularly limited.

  Example 1 1.0 g of astaxanthin (synthetic product, manufactured by Sigma), 4.0 g of powdery γ-cyclodextrin (trade name DEXIPAL γ-100, manufactured by Shimizu Minato Sugar Co., Ltd.), ethanol-dichloromethane (volume ratio = 1: 1) 4 ml of the mixed solution and 4 ml of ion-exchanged water were placed in a mortar and mixed well with a pestle. After the organic solvent was volatilized, 4 ml of a mixed solution of ethanol-dichloromethane (volume ratio = 1: 1) was added again and mixed well. This operation was repeated three times to obtain a paste. The solvent added in the final stage was almost volatilized, and the residue of the wet powder was dried overnight under reduced pressure in a vacuum dryer.

  Example 2 1.0 g of astaxanthin oil obtained in Reference Example 1, 2.0 g of the above γ-cyclodextrin, 2 ml of a mixed solution of ethanol-dichloromethane (volume ratio = 1: 1) and 2 ml of ion-exchanged water were put in a mortar, and a pestle Mix well. After the organic solvent was volatilized, 2 ml of a mixed solution of ethanol-dichloromethane (volume ratio = 1: 1) was added again and mixed well. This operation was repeated three times to obtain a paste. The solvent added in the final stage was almost volatilized, and the residue of the wet powder was dried overnight under reduced pressure in a vacuum dryer.

  Example 3 After adding 4.0 g of the above-mentioned γ-cyclodextrin and 4.0 ml of water to a mortar and kneading well, 1.0 g of astaxanthin oil obtained in Reference Example 1 and ethanol-dichloromethane (like quality = 1: 1) 4.0 ml of the mixed solution was added and kneaded well. After the organic solvent was volatilized, 4 ml of a mixed solution of ethanol-dichloromethane (volume ratio = 1: 1) was added again and mixed well. This operation was repeated three times to obtain a paste. The solvent added in the final stage was almost volatilized, and the residue of the wet powder was dried overnight under reduced pressure in a vacuum dryer.

  Example 4 1.0 g of astaxanthin oil obtained in Reference Example 1, 4.0 g of the above-mentioned γ-cyclodextrin, 10 ml of water and 10 ml of a mixed solution of ethanol-dichloromethane (volume ratio = 1: 1) were placed in an eggplant type flask. The organic solvent was distilled off under reduced pressure using a rotary evaporator. After the solvent was distilled off, 10 ml of a mixed solution of ethanol-dichloromethane (volume ratio = 1: 1) was added again, and the mixture was heated to 60 ° C. and the organic solvent was distilled off under reduced pressure. This operation was repeated 4 times. Finally, water was completely distilled off, followed by drying overnight under reduced pressure in a vacuum dryer.

  Example 5 1.0 g of astaxanthin oil obtained in Reference Example 1, 5.0 g of the above-mentioned γ-cyclodextrin, 10 ml of water and 10 ml of a mixed solution of ethanol-dichloromethane (volume ratio = 1: 1) were placed in an eggplant type flask. The mixture was heated to 0 ° C. and refluxed for 3 hours. Centrifugation was performed, and the residue (solid content) was taken out and dried overnight in a vacuum dryer under reduced pressure.

  Example 6 1.0 g of astaxanthin oil obtained in Reference Example 1, 5.0 g of the above-mentioned γ-cyclodextrin, 10 ml of water and 10 ml of a mixed solution of ethanol-dichloromethane (volume ratio = 1: 1) were placed in an eggplant type flask. The mixture was heated to 0 ° C. and refluxed for 3 hours. After adding 10 ml of ethanol, the mixture was centrifuged, and the residue (solid content) was taken out. After this operation was repeated twice, it was dried overnight under reduced pressure in a vacuum dryer. 10 ml of water was added and the mixture was shaken for 30 minutes and centrifuged. After performing the same operation again, it was dried overnight in a vacuum dryer under reduced pressure.

  Comparative Example 1 1.0 g of astaxanthin oil obtained in Reference Example 1 and 2.0 g of the above γ-cyclodextrin were placed in a mortar and mixed well with a pestle.

  Comparative Example 2 1.0 g of astaxanthin oil obtained in Reference Example 1, 2.0 g of the above-mentioned γ-cyclodextrin and 2.0 g of water were placed in a mortar and mixed well with a pestle, and then overnight under reduced pressure in a vacuum dryer. Dried.

  Comparative Example 3 1.0 g of astaxanthin oil obtained in Reference Example 1, 2.0 g of the above-mentioned γ-cyclodextrin, 2.0 g of water and 2.0 ml of ethanol were put in a mortar, mixed well with a pestle, and the solvent was almost volatilized. After that, it was dried in a vacuum dryer under reduced pressure overnight.

  Comparative Example 4 1.0 g of astaxanthin oil obtained in Reference Example 1, 2.0 g of the above γ-cyclodextrin, 2.0 g of water and 2.0 ml of dichloromethane were placed in a mortar and mixed well with a pestle to volatilize most of the solvent. After that, the pressure was reduced with a vacuum dryer and dried overnight. Prepared with different solvents.

  Table 1 below shows a method for preparing powders of astaxanthin and γ-cyclodextrin obtained by the methods of Examples 1 to 6 and Comparative Examples 1 to 3, types of solvents, blending amount of γ-cyclodextrin with respect to astaxanthin, and stability. The result (residual rate) of the test is shown. In the table, γ-CD means γ-cyclodextrin, ET means ethanol, DM means dichloromethane, and the addition amount is shown by weight.

  The stability comparison test was performed by the method shown below. 10 mg of each test substance was placed in a capped test tube (10 ml), replaced with oxygen, sealed, heated at 80 ° C., and the astaxanthin content after 2 hours and 4 hours was measured. The content of astaxanthin in the clathrate was measured by an absorbance method (measurement length: 485 nm, solvent chloroform) after extraction with chloroform.

  From the results shown in Table 1, the clathrate compound obtained by the production method of the present invention was extremely stable with 83 to 99% of astaxanthin remaining after a severe test at 80 ° C. for 4 hours under oxygen substitution. On the other hand, in the powders prepared by the conventional methods of Comparative Examples 1 to 4, the content of astaxanthin after 4 hours was extremely low and unstable. From the XRD spectra of FIGS. 1 and 2, it can be seen that the inclusion compound of the present invention is not a simple mixture but forms an inclusion compound of astaxanthin and γ-cyclodextrin.

  The clathrate compound of the present invention is a stable powder and has the feature of being easily dissolved in water. The solubility and transparency of the clathrate compound of the present invention in water will be described below.

  Appropriate amount of each sample of the clathrate compound obtained in Examples 1-6 and the mixture obtained in Comparative Examples 1-4 is added to a desired amount of water and dissolved with a stirrer, ultrasonic shaker, etc. After centrifugation, the astaxanthin content in the supernatant was measured, and a solubility comparison test was performed.

  Test Examples B1 to B10 20 mg of each sample was added to 50 ml of water, subjected to ultrasonic shaking for 5 minutes, centrifuged, and the astaxanthin content in the supernatant was measured. The results are shown in Table 2. In the table, solubility means that ◯ is a state without precipitation, Δ is a state where a small amount of precipitation is generated, and X is a state where oil droplets are floating.

As is apparent from the results in Table 2 above, it can be seen that the inclusion compound of astaxanthin and γ-cyclodextrin obtained by the methods of Examples 1 to 6 of the present invention is very easily soluble in water. These solutions were left in a place not exposed to direct sunlight for 1 month at room temperature, but no fading was observed.

On the other hand, powders obtained by the conventional methods of Comparative Examples 1 to 4 floated astaxanthin oil when only water was added, and only γ-cyclodextrin was dissolved in water.

  From the above results, the inclusion compound of astaxanthin and γ-cyclodextrin obtained by the production method characterized by blending γ-cyclodextrin at a specific ratio with the astaxanthin of the present invention is extremely stable against heat. It can also be seen that the inclusion compound is easily dissolved in water.

  Production Example 1 Inclusion compound of tablet Example 6 15 g Avicel 35 g Reduced maltose starch syrup 15 g Partially pregelatinized starch 10 g Light anhydrous silicic acid 2 g Sprayed lactose 20 g Sucrose fatty acid ester 3 g A 300 mg tablet was prepared.

  Production Example 2 Capsule Gelatin 70 g Glycerin 23 g Propyl paraoxybenzoate 1 g Water 6 g The soft capsule skin composed of the above ingredients was filled with the content of the inclusion compound 30% by weight of Example 6 and 70% by weight of coconut oil 300 mg Capsule.

  Production Example 3 Drink Agent Inclusion Compound of Example 6 2 g DL-Sodium Tartrate 0.1 g Liquid Sugar 800 g Citric Acid 12 g Vitamin C 10 g Vitamin E 30 g Fragrance 1.5 g Potassium Chloride 0.1 g Magnesium Sulfate 0.5 g Water was added to 10 L, and a drink was prepared according to a conventional method.

  Production Example 4 Cream Inclusion compound of Example 6 1 g Glycerin monosteric acid 7 g Propylene glycol 5 g Squalane 15 g Methyl paraoxybenzene 0.1 g Propyl paraoxybenzene 0.1 g Add water to the above ingredients to make 100 g, A cream was prepared according to a conventional method.

  Production Example 5 Soft Drink 2g Inclusion Compound 2g Liquid Sugar 1000g Citric Acid 16g Ascorbic Acid 2g Fragrance 15g The above ingredients were mixed with 10L of water, and a transparent soft drink was prepared according to a conventional method.

  Production Example 6 Cookies Inclusion compound of Example 6 2 g Milk 630 g Sugar 130 g Corn starch 130 g Salt 10 g The above ingredients were blended, and the cookies were baked according to a conventional method.

  Production Example 7 Inclusion Compound of Example 6 2 g Corn flour 300 g Wheat flour 300 g Fish flour 50 g Alfalfa meal 50 g Cassava meal 50 g Fusuma 50 g Soy flour 200 g The above ingredients were blended into pellets according to a conventional method to prepare chicken feed.

Claims (8)

An inclusion compound of astaxanthin and / or an ester thereof and γ-cyclodextrin, which is blended at a ratio of 0.5 to 100 parts by weight of γ-cyclodextrin to 1 part by weight of astaxanthin and / or an ester thereof. The inclusion compound according to claim 1, wherein the ester of astaxanthin is at least one selected from the group of astaxanthin fatty acid monoester and astaxanthin fatty acid diester. The inclusion compound according to claim 1 or 2, wherein the astaxanthin and / or its ester is an oil of astaxanthin and / or its ester extracted from Haematococcus alga. The inclusion compound according to any one of claims 1 to 3, which is blended in a proportion of 0.5 to 50 parts by weight of γ-cyclodextrin with respect to 1 part by weight of astaxanthin and / or an ester thereof. The inclusion compound according to any one of claims 1 to 3, which is blended in an amount of 1 to 5 parts by weight of γ-cyclodextrin with respect to 1 part by weight of astaxanthin and / or an ester thereof. The liquid agent containing the clathrate compound of any one of Claims 1-5. The food / beverage containing the clathrate compound in any one of Claims 1-5. Cosmetics containing the inclusion compound according to any one of claims 1 to 5.

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