Composition

Abstract

To provide a composition that allows the formation of a powder exhibiting low levels of agglomeration, as well as excellent redispersibility in aqueous media, excellent redispersibility under acidic conditions, and improved transparency after redispersion, and also suppresses light-induced coloration.SOLUTION: A composition comprises a cannabinoid (A), a sucrose fatty acid ester (B), and a dextrin (C) having a cyclic structure, wherein the cyclic structure is composed of 10 to 500 glucose units.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to compositions comprising cannabinoids. [Background technology]

[0002] Cannabinoids are contained in the leaves and seed coats of hemp plants, and are known to contain various components such as cannabidiol (CBD). Cannabidiol has unique effects and is widely used in the food industry, such as food additives, and in the medical industry, such as pharmaceuticals, making it a highly useful component. Summary of the Invention [Problem to be solved by the invention]

[0003] However, cannabinoids, especially cannabidiol, are difficult to powderize, and once powderized, they have poor dispersibility in aqueous media. In addition, when the powder is redispersed, coloring due to light is likely to occur, and the storage environment and use environment may be limited. The present invention has been made in view of the above, and aims to provide a composition that has few aggregates, has excellent redispersibility in aqueous media, and can suppress coloring due to light. [Means for solving the problem]

[0004] As a result of extensive research into achieving the above-mentioned objective, the inventors discovered that the above-mentioned objective can be achieved by using dextrin having a cyclic structure as an essential component together with sucrose fatty acid ester, and thus completed the present invention.

[0005] That is, the present invention includes, for example, the subject matter described in the following sections. Item 1 A composition comprising a cannabinoid (A), a sucrose fatty acid ester (B) and a dextrin having a cyclic structure (C). Section 2 Item 2. The composition according to item 1, comprising 5 to 150 parts by mass of the dextrin having a cyclic structure (C) relative to 100 parts by mass of the sucrose fatty acid ester (B). Section 3 Item 3. The composition according to item 1 or 2, wherein the sucrose fatty acid ester has an average degree of esterification of 1.00 to 1.15. Section 4 Item 4. The composition according to any one of items 1 to 3, which is in a powder form. Section 5 5. The composition according to any one of items 1 to 4, which is for food, cosmetic, feed, or pharmaceutical use. Effect of the Invention

[0006] The composition of the present invention has few aggregates, has excellent redispersibility in aqueous media, and is capable of suppressing coloration due to light. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] Hereinafter, embodiments of the present invention will be described in detail. In this specification, the expressions "containing" and "comprise" include the concepts of "containing", "comprises", "consists essentially of" and "consists only of".

[0008] 1. Composition The composition of the present invention contains a cannabinoid (A), a sucrose fatty acid ester (B) and a dextrin (C) having a cyclic structure, and the cyclic structure is composed of 10 to 500 glucose units. The composition of the present invention contains the sucrose fatty acid ester (B) and the dextrin (C) having a cyclic structure in a composition containing a cannabinoid (A), so that a powder having less aggregates, excellent redispersibility in an aqueous medium, redispersibility under acidic conditions, and transparency after redispersion can be formed, and coloring due to light can be suppressed. In addition, the composition of the present invention can suppress coloring due to light even under acidic conditions. In this specification, "under acidic conditions" means that the pH of the emulsion composition is 7 or less, preferably 4 or less.

[0009] (Cannabinoids (A)) As the cannabinoid (A) contained in the composition of the present invention, for example, one or more of the various compound groups contained in hemp-derived cannabinoids (specifically, cannabidiol (CBD), tetrahydrocannabinol, etc.) can be used.

[0010] The cannabinoid (A) preferably contains cannabidiol. In this case, it has excellent dispersibility in a solvent, particularly an aqueous solvent, and is particularly applicable to the food, cosmetics, feed, or pharmaceutical fields. The cannabinoid (A) preferably contains 50% by mass or more of cannabidiol, more preferably 80% by mass or more, even more preferably 90% by mass or more, and particularly preferably 95% by mass or more. The cannabinoid (A) may be only cannabidiol.

[0011] Cannabinoid (A) can be prepared, for example, by known methods. Alternatively, commercially available cannabinoids can be applied to the composition of the present invention. Similarly, cannabidiol can be prepared, for example, by known methods, or commercially available cannabidiol can be applied to the composition of the present invention.

[0012] (Sucrose fatty acid ester (B)) The sucrose fatty acid ester (B) contained in the composition of the present invention is a compound formed by an esterification reaction between sucrose and a fatty acid.

[0013] In the sucrose fatty acid ester (B), the type of the fatty acid moiety (RCOO-moiety) of the sucrose fatty acid ester is not particularly limited. The fatty acid moiety of the sucrose fatty acid ester may be a moiety derived from a saturated fatty acid or a moiety derived from an unsaturated fatty acid, and is preferably derived from a saturated fatty acid.

[0014] In the sucrose fatty acid ester (B), the number of carbon atoms in the fatty acid moiety of the sucrose fatty acid ester is not particularly limited, and the number of carbon atoms in the fatty acid moiety (including ester carbon) is preferably 30 or less, more preferably 25 or less, even more preferably 20 or less, and particularly preferably 18 or less, in order to form a powder with fewer aggregates, better redispersibility in an aqueous medium, better redispersibility under acidic conditions, and better transparency after redispersion, and to further suppress coloration of the composition. In addition, the number of carbon atoms in the fatty acid moiety (including ester carbon) is preferably 8 or more, more preferably 10 or more, even more preferably 12 or more, and particularly preferably 14 or more, in order to form a powder with fewer aggregates, better redispersibility in an aqueous medium, better redispersibility under acidic conditions, and better transparency after redispersion, and to further suppress coloration of the composition. The fatty acid moiety in the sucrose fatty acid ester is preferably derived from, for example, lauric acid, palmitic acid, stearic acid, etc.

[0015] Sucrose fatty acid ester (B) exists in monoester, diester and triester forms. The sucrose fatty acid ester contained in the composition of the present invention may be any of these ester forms, and may contain not only one but also two or all of the ester forms. In other words, the sucrose fatty acid ester (B) may contain one or more sucrose fatty acid esters selected from the group consisting of monoester, diester and triester.

[0016] The average degree of esterification of the sucrose fatty acid ester (B) is preferably in the range of 1.00 to 1.15. That is, the average degree of esterification of the sucrose fatty acid ester (B) is preferably 1.00 or more and 1.15 or less. The average degree of esterification of the sucrose fatty acid ester (B) is preferably 1.01 or more. The average degree of esterification of the sucrose fatty acid ester (B) is preferably 1.12 or less, more preferably 1.10 or less, and particularly preferably 1.08 or less. When the average degree of esterification of the sucrose fatty acid ester (B) is within the above range, a powder having fewer aggregates and having excellent redispersibility in an aqueous medium, redispersibility under acidic conditions, and transparency after redispersion can be formed, and coloring of the composition can be further suppressed.

[0017] In the present invention, the average degree of esterification of the sucrose fatty acid ester (B) can be calculated as the average degree of esterification X of the sucrose fatty acid ester by the following formula (1). (Ns-X)=(Nx) / (Ny) ={(OHV) / (1000×56.11)} / {1 / (MwSug+(MwFa-18)X)} (1)

[0018] Here, the meanings of the symbols in formula (1) are as follows: Ns: number of OH groups in one sucrose molecule Nx: Number of moles of OH groups in 1 g of sample (sucrose fatty acid ester) Ny: number of moles of sucrose fatty acid ester in 1 g of sample OHV: Hydroxyl value of sucrose fatty acid ester MwSug: Molecular weight of sucrose MwFa: average molecular weight of constituent fatty acids

[0019] X can be calculated by substituting known values ​​of Ns, Nx, Ny, OHV, MwSug, and MwFa into the above formula (1). Note that Ns, Nx, Ny, OHV, MwSug, and MwFa can be measured by known methods.

[0020] As can be seen from the above method for calculating the average degree of esterification, the sucrose fatty acid ester (B) in the present invention can be said to be an aggregate of sucrose fatty acid ester molecules having different degrees of esterification.

[0021] In the composition of the present invention, when a commercially available product is used as the sucrose fatty acid ester (B), the value disclosed by the manufacturer, such as the manufacturer's guaranteed value or catalog value of the sucrose fatty acid ester, can be used as the average degree of esterification.

[0022] The type of sucrose fatty acid ester (B) is not particularly limited as long as the average degree of esterification is within the above range, and for example, a wide variety of known sucrose fatty acid esters can be applied to the composition of the present invention.

[0023] The method for producing the sucrose fatty acid ester (B) is not particularly limited, and for example, known production methods can be widely adopted. For example, the sucrose fatty acid ester can be synthesized by transesterification of sucrose and fatty acid ester. The fatty acid ester can be a methyl ester of fatty acid.

[0024] The sucrose used in the method for producing sucrose fatty acid ester (B) may be synthesized by a known method, or sucrose may be available as a commercially available product. The sucrose may be unreacted sucrose recovered during the production of sucrose fatty acid ester (so-called "recovered sugar"). The sucrose may be in a solid state or in a solution state dissolved in a solvent. The fatty acid used in the method for producing sucrose fatty acid ester may be synthesized by a known method, or fatty acid may be available as a commercially available product.

[0025] The method for adjusting the average esterification degree of the sucrose fatty acid ester (B) is not particularly limited, and for example, known methods can be widely adopted. For example, the average esterification degree of the obtained sucrose fatty acid ester can be controlled within a desired range by adjusting various synthesis conditions such as the ratio of sucrose and fatty acid or its ester used in the production of the sucrose fatty acid ester, the type of fatty acid, and the esterification reaction conditions.

[0026] Alternatively, the average degree of esterification of the sucrose fatty acid ester may be controlled to a desired range by mixing two or more sucrose fatty acid esters having different average degrees of esterification, in which case the average degree of esterification of each sucrose fatty acid ester can be easily adjusted to a desired range based on the degree of esterification of each sucrose fatty acid ester and the mixing mass ratio.

[0027] In the composition of the present invention, the content ratio of sucrose fatty acid ester (B) is not particularly limited. For example, in terms of being able to form a powder with fewer aggregates, better redispersibility in an aqueous medium, better redispersibility under acidic conditions, and better transparency after redispersion, and being able to further suppress coloring of the composition, the content of sucrose fatty acid ester is preferably 100 parts by mass or more when the total mass of the cannabinoid (A) in the composition is 100 parts by mass, more preferably 200 parts by mass or more, even more preferably 300 parts by mass or more, particularly preferably 400 parts by mass or more, and preferably 3000 parts by mass or less, more preferably 2000 parts by mass or less, even more preferably 1500 parts by mass or less, and particularly preferably 1000 parts by mass or less.

[0028] The compositions of the present invention may contain one or more sucrose fatty acid esters.

[0029] (Dextrin having a cyclic structure (C)) The composition of the present invention contains a dextrin (C) having a cyclic structure, and the cyclic structure is composed of 10 to 500 glucose units.

[0030] The cyclic structure preferably has a structure in which a plurality of glucose molecules are bound by at least one type of bond selected from the group consisting of 1,4-glycosidic bonds and 1,6-glycosidic bonds. It is also preferable that the molecule has one cyclic structure.

[0031] The weight-average molecular weight of the dextrin (C) having a cyclic structure is not particularly limited, but is preferably from 10,000 to 1,000,000, and more preferably from 100,000 to 700,000, for example.

[0032] The dextrin (C) having a cyclic structure can be produced by a known method, and can also be obtained as a commercially available product.

[0033] An example of a commercially available product is Cluster Dextrin (registered trademark). Cluster dextrin is a dextrin having a cyclic structure produced by acting a branching enzyme on amylopectin, that is, a glucan having a cyclic structure produced by acting a glycosyltransferase on saccharides having α-1,4-glucosidic bonds and α-1,6-glucosidic bonds. More specifically, as described in the specification of Japanese Patent No. 3107358, it is a glucan having a degree of polymerization of 50 (n=50) or more and having an inner branched cyclic structure portion and an outer branched structure portion. Here, the inner branched cyclic structure portion is a cyclic structure portion formed by an α-1,4-glucosidic bond and an α-1,6-glucosidic bond, and the outer branched structure portion is a non-cyclic structure portion bonded to the inner branched cyclic structure portion.

[0034] The dextrin (C) having a cyclic structure has the cyclic structure (for example, the inner branched cyclic structure portion in the cluster dextrin) preferably composed of 10 to 500 glucose units, more preferably composed of 12 to 300 glucose units, and even more preferably composed of 15 to 200 glucose units.

[0035] In the dextrin (C) having a cyclic structure, each unit chain of the portion other than the cyclic structure (for example, the outer branched structure portion in the cluster dextrin) is preferably composed of an average of 5 to 50 glucose units, more preferably 8 to 30 glucose units, and even more preferably 10 to 20 glucose units.

[0036] The dextrin (C) having a cyclic structure is preferably composed of 30 to 5,000 glucose molecules, more preferably composed of 50 to 3,000 glucose molecules, and even more preferably composed of 60 to 1,000 glucose molecules.

[0037] The dextrin (C) having a cyclic structure has a specific structure and a high degree of polymerization as described above, and is different from general "cyclodextrins" in which 6 to 8 glucose molecules are bonded, such as α-cyclodextrin (n=6), β-cyclodextrin (n=7), and γ-cyclodextrin (n=8).

[0038] In the composition of the present invention, the content ratio of the dextrin (C) having a cyclic structure is not particularly limited. For example, the content ratio of the dextrin (C) having a cyclic structure is preferably 5 to 150 parts by mass, more preferably 10 to 100 parts by mass, further preferably 15 to 80 parts by mass, and particularly preferably 20 to 70 parts by mass, relative to 100 parts by mass of the sucrose fatty acid ester (B). By setting it within the above range, a powder with fewer aggregates and excellent redispersibility in an aqueous medium, redispersibility under acidic conditions, and transparency after redispersion can be formed, and coloring of the composition can be further suppressed.

[0039] For example, the content ratio of the dextrin (C) having a cyclic structure is preferably 10 to 1000 parts by mass, more preferably 30 to 800 parts by mass, further preferably 50 to 600 parts by mass, and particularly preferably 100 to 400 parts by mass, relative to 100 parts by mass of the cannabinoid (A). By setting the content within the above range, a powder having fewer aggregates, redispersibility in an aqueous medium, redispersibility under acidic conditions, and transparency after redispersion can be formed, and coloring of the composition is further suppressed.

[0040] (Other ingredients) The composition of the present invention may contain other components in addition to the cannabinoid (A), sucrose fatty acid ester (B), and dextrin having a cyclic structure (C) as long as the effect of the present invention is not inhibited. For example, the composition of the present invention may contain a surfactant other than the sucrose fatty acid ester (B). Such surfactants may include a wide range of known surfactants, such as sorbitan fatty acid esters and polyglycerin fatty acid esters.

[0041] The composition of the present invention may also contain fats and oils. In this case, the dispersibility of the cannabinoid (A) is improved, so that the composition of the present invention is easily applicable to various additives in the fields of food, cosmetics, feed, medicine, etc.

[0042] The fats and oils include edible fats and oils, specifically synthetic fats and oils such as medium-chain fatty acid triglycerides such as MCT oil, vegetable fats and oils such as cottonseed oil, castor oil, soybean oil, rapeseed oil, corn oil, olive oil, palm oil, safflower oil, rice oil, sunflower oil, sesame oil, and animal fats and oils such as lard, beef tallow, milk fat, and fish oil. For example, commercially available fats and oils can be widely used. The fats and oils contained in the composition can be one type alone or two or more types.

[0043] When the composition of the present invention contains oils and fats, the content ratio thereof is, for example, preferably 20 parts by mass or more, more preferably 40 parts by mass or more, even more preferably 60 parts by mass or more, and particularly preferably 80 parts by mass or more, per 100 parts by mass of the total mass of the cannabinoid (A), and is preferably 500 parts by mass or less, more preferably 400 parts by mass or less, even more preferably 300 parts by mass or less, and particularly preferably 200 parts by mass or less.

[0044] The composition of the present invention may also contain a water-soluble polymer. In this case, the dispersibility of the cannabinoid (A) is easily improved, so that the composition of the present invention is easily applied to various additives in the food, cosmetic, feed, or pharmaceutical fields. The water-soluble polymer compound in the present invention means a polymer compound that can be dissolved in water. For example, a polymer compound that dissolves in 100 parts by mass of water at 0.1 parts by mass or more can be considered as a water-soluble polymer compound.

[0045] Examples of the water-soluble polymer compound include a wide variety of known water-soluble polymer compounds, such as cellulose derivatives, polyvinylpyrrolidone, polyacrylic acid or a salt thereof, polymethacrylic acid or a salt thereof, polyvinyl alcohol, polyalkylene oxide, polystyrene sulfonic acid or a salt thereof, etc. Among these, the water-soluble polymer compound is preferably at least one selected from the group consisting of cellulose derivatives and polyvinylpyrrolidone.

[0046] The cellulose derivatives include, for example, hydroxyalkyl cellulose. Specifically, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxy Examples of the cellulose acetate include hydroxypropyl cellulose.

[0047] When the composition of the present invention contains a water-soluble polymer, the content ratio thereof is preferably, for example, 3 to 200 parts by mass per 100 parts by mass of the sucrose fatty acid ester (B) in the composition of the present invention, which tends to result in more excellent dispersibility and transparency of the composition.

[0048] The composition of the present invention may also contain an antioxidant. In this case, coloring of the composition is further suppressed, so that the composition of the present invention is easily applicable to various additives in the fields of food, cosmetics, feed, medicine, etc.

[0049] Examples of the antioxidant include ascorbic acid, gallic acid, α-tocopherol, and known extracts, and their derivatives can also be used. Among these, ascorbic acid and its derivatives are preferred because they can further suppress coloring of the composition.

[0050] Examples of ascorbic acid and its derivatives include L-ascorbic acid, D-ascorbic acid, L-ascorbic acid derivatives such as sodium L-ascorbate, calcium L-ascorbate, L-ascorbic acid stearate, and L-ascorbic acid palmitate, and D-ascorbic acid derivatives such as sodium D-ascorbate, calcium D-ascorbate, D-ascorbic acid stearate, and D-ascorbic acid palmitate. Among these, L-ascorbic acid and L-ascorbic acid derivatives are preferred, and L-ascorbic acid, sodium L-ascorbate, and calcium L-ascorbate are more preferred, since they can further suppress coloration of the composition and have better dispersibility and transparency.

[0051] When the composition of the present invention contains an antioxidant, the content ratio thereof is, for example, preferably 1 to 500 parts by mass, more preferably 3 to 300 parts by mass, even more preferably 5 to 200 parts by mass, and particularly preferably 7 to 150 parts by mass, relative to 100 parts by mass of the cannabinoid (A). The content ratio of the antioxidant is preferably 0.1 to 30 parts by mass, more preferably 0.2 to 20 parts by mass, even more preferably 0.3 to 15 parts by mass, and particularly preferably 0.4 to 10 parts by mass, relative to 100 parts by mass of the sucrose fatty acid ester (B). By setting it within the above range, the coloring of the composition can be further suppressed, and the dispersibility and transparency are more excellent.

[0052] The composition of the present invention may contain other additives, for example, various additives widely used in food applications and various additives widely used in pharmaceutical applications. When the composition of the present invention contains other additives, the content ratio thereof is, for example, 50% by mass or less, preferably 30% by mass or less, more preferably 20% by mass or less, even more preferably 10% by mass or less, and particularly preferably 1% by mass or less, based on the total mass of the composition.

[0053] (Form of composition) The composition of the present invention may be in a liquid form such as a dispersion, or in a solid form such as a powder.

[0054] When the composition of the present invention is a dispersion liquid, the composition of the present invention can further contain a solvent.As such a solvent, it is preferable that it is an aqueous solvent, since it is easy to increase the dispersibility of cannabinoid (A) (especially cannabidiol).As the aqueous solvent, water and alcohol can be mentioned.

[0055] The alcohol component may include lower alcohol compounds such as methanol, ethanol, isopropanol, etc., as well as polyhydric alcohol compounds such as glycerin.

[0056] The aqueous solvent may be a mixed solvent of water and the lower alcohol and / or the polyhydric alcohol, or the aqueous solvent may be only the alcohol content of the lower alcohol and the polyhydric alcohol. When the aqueous solvent contains a mixture of a lower alcohol and a polyhydric alcohol, examples of the lower alcohol include methanol, ethanol, isopropanol, etc., and examples of the polyhydric alcohol include glycerin.

[0057] When the composition of the present invention is a dispersion, the aqueous solvent preferably contains at least an alcohol component such as a lower alcohol compound and a polyhydric alcohol compound, etc. In this case, the composition is likely to have better dispersibility and transparency.

[0058] When the aqueous solvent contains an alcohol content including a lower alcohol compound and a polyhydric alcohol compound, the ratio of the lower alcohol compound and the polyhydric alcohol compound is not particularly limited, and for example, the content ratio of the polyhydric alcohol compound is 10 to 50 parts by mass per 100 parts by mass of the lower alcohol compound.

[0059] When the composition of the present invention is a dispersion containing an aqueous solvent, and the aqueous solvent contains an alcohol content such as a lower alcohol compound and a polyhydric alcohol compound, the content ratio of the alcohol content is, for example, preferably 100 parts by mass or more, more preferably 500 parts by mass or more, and even more preferably 1000 parts by mass or more, relative to 100 parts by mass of the total mass of the cannabinoid, and is preferably 10,000 parts by mass or less, more preferably 5,000 parts by mass or less, even more preferably 3,000 parts by mass or less, and particularly preferably 2,000 parts by mass or less.

[0060] When the composition of the present invention is a dispersion containing a solvent, the total content of the solvent is not particularly limited. For example, the content of the cannabinoid and the sucrose fatty acid ester relative to 100 parts by mass of the solvent is preferably 0.01 to 20 parts by mass, more preferably 0.05 to 10 parts by mass, even more preferably 0.1 to 5 parts by mass, and particularly preferably 0.2 to 3 parts by mass.

[0061] When the composition of the present invention is a dispersion containing a solvent, the median diameter (D50) of the dispersion is not particularly limited. For example, the median diameter (D50) of the dispersion is preferably 1 to 150 nm, more preferably 1 to 100 nm, even more preferably 1 to 50 nm, and particularly preferably 1 to 20 nm, in terms of the fact that the dispersion stability is likely to be good and the powderization described below can be easily performed. The median diameter (D50) of the dispersion can be measured by a dynamic light scattering method using a particle size measuring device (trade name: nanoSAQLA, manufactured by Otsuka Electronics Co., Ltd.). The median diameter (D50) means the particle diameter D50 at which the cumulative frequency becomes 50% in the scattering intensity distribution.

[0062] The composition of the present invention may be a powder. In this case, the average particle size of the powder is not particularly limited. For example, the volume average particle size of the powder is preferably 0.1 to 500 μm, more preferably 1 to 150 μm, and particularly preferably 10 to 100 μm, in terms of being suitable for use as various additives. The volume average particle size of the powder can be measured using a particle size distribution measuring device (product name: MT3000II, manufactured by Microtrackbell Co., Ltd.). When the composition of the present invention is a powder, such a powder is composed of, for example, aggregated particles.

[0063] Even when the composition of the present invention is in the form of a powder, it may contain various additives. However, the aqueous solvent (e.g., water, and alcohols such as lower alcohol compounds and polyhydric alcohol compounds) may volatilize in part or in whole during the powdering process. When the composition of the present invention is in the form of a powder, the content of the lower alcohol compounds and polyhydric alcohol compounds in the powder is about 10 to 25% by mass.

[0064] When the composition of the present invention is a powder, the method of manufacture is not particularly limited, and for example, the composition of the present invention, which is a dispersion, can be powdered by drying the solvent by an appropriate method. The method of drying the solvent is not particularly limited, and various known methods, such as heat drying, spray drying, and freeze drying, can be mentioned. Therefore, one embodiment of the present invention can be a powder that is a dried product of the dispersion. The powder obtained by such a method is, for example, a powder formed by drying an aqueous dispersion containing cannabinoids.

[0065] Since the powder contains a cannabinoid, a specific sucrose fatty acid ester, and a water-soluble polymer compound, it has better dispersibility in a solvent (particularly an aqueous solvent), and even if the solvent (particularly an aqueous solvent) is under acidic conditions, it is likely to have better dispersibility. That is, when the composition of the present invention is a powder, it has excellent redispersibility in an aqueous medium, and even under acidic conditions. Therefore, when the composition of the present invention is used as a powdered additive, it is possible to maintain a good dispersion state. In addition, by having the property of excellent redispersibility, the amount of powder added can be increased, that is, the proportion (concentration) of cannabinoid can be increased compared to the conventional case, and it is also possible to provide a composition containing a high concentration of cannabinoid.

[0066] The composition of the present invention can be applied to various applications, and in particular, can be widely applied to applications in which compositions containing cannabidiol have been used in the past. Specifically, the composition of the present invention can be applied to food, cosmetics, feed, or medicine. Regardless of whether the composition of the present invention is in the form of a dispersion liquid or a powder, it can be used for the above-mentioned various applications. In this specification, the term "food use" broadly includes beverages, supplements, health foods, functional foods, foods for beauty purposes, and animal feeds such as pets. In addition, in this specification, the term "feed use" broadly includes feeds that can be used in various livestock fields, and also includes feeds used in aquaculture. In this specification, the term "medicinal use" includes medicines for taking or administering to humans, as well as medicines for taking or administering to animals. When the composition of the present invention is applied to food, cosmetics, or medicine, any of these uses includes those for beauty purposes.

[0067] As described above, the composition of the present invention can be particularly suitably used as, for example, a food additive, a feed additive, a pharmaceutical additive, and a cosmetic additive.

[0068] (Method of preparing the composition) The method for producing the composition of the present invention is not particularly limited, and can be produced by various methods using, for example, cannabinoid (A), sucrose fatty acid ester (B) and dextrin having a cyclic structure (C). For example, a method of mixing a raw material solution containing cannabinoid (A) with a raw material solution containing sucrose fatty acid ester (B) and dextrin having a cyclic structure (C) in random order can be mentioned. In addition, a method of mixing a raw material solution containing cannabinoid (A) and dextrin having a cyclic structure (C) with a raw material solution containing sucrose fatty acid ester (B) in random order can be mentioned. In addition, a method of mixing a raw material solution containing cannabinoid (A) and sucrose fatty acid ester (B) with a raw material solution containing dextrin having a cyclic structure (C) in random order can be mentioned.

[0069] The ratio of the cannabinoid (A) to the solvent is not particularly limited. For example, the amount of the solvent used may be 50 to 200 parts by mass, and preferably 80 to 150 parts by mass, per 100 parts by mass of the cannabinoid (A).

[0070] The raw material solution containing the sucrose fatty acid ester (B) and the dextrin having a cyclic structure (C) may contain a solvent, and examples of the solvent include the above-mentioned aqueous solvents (e.g., water, a lower alcohol compound, and a polyhydric alcohol compound). The polyhydric alcohol compound may be added after mixing the raw material solution containing the cannabinoid (A) with the raw material solution containing the sucrose fatty acid ester (B) and the dextrin having a cyclic structure (C). The ratio of the sucrose fatty acid ester (B) to the solvent is not particularly limited, and for example, the amount of the solvent used may be 50 to 200 parts by mass, and preferably 80 to 150 parts by mass, per 100 parts by mass of the sucrose fatty acid ester (B). The ratio of the dextrin having a cyclic structure (C) to the solvent is not particularly limited, and for example, the amount of the solvent used may be 50 to 200 parts by mass, and preferably 80 to 150 parts by mass, per 100 parts by mass of the dextrin having a cyclic structure (C).

[0071] For example, when mixing a raw material liquid containing a cannabinoid (A) and a solvent, a raw material liquid containing a sucrose fatty acid ester (B) and a solvent, and a raw material liquid containing a dextrin having a cyclic structure (C) and a solvent, the temperature during mixing is not particularly limited, and is, for example, 20 to 100°C, preferably 30 to 90°C, and more preferably 40 to 80°C. The mixing method is also not particularly limited, and for example, a known mixer can be widely used. The concentration can also be adjusted by further adding water or the like to the composition obtained as described above. EXAMPLES

[0072] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the embodiments of these examples.

[0073] (Production Example 1) In a 1L flask equipped with a stirrer, a thermometer, a pressure reducing device, and a reflux device for dimethyl sulfoxide (DMSO), 400g of DMSO and 34.2g of sucrose were mixed and dissolved at 95°C. 2.4g of potassium carbonate and 15.0g of methyl stearate as a fatty acid ester were added thereto, and the mixture was reacted at 95°C for 3 hours under a reduced pressure of 2kPa. Subsequently, lactic acid was added to neutralize the mixture, and then DMSO was distilled off under reduced pressure. The obtained crude product was dissolved in 200g of methyl ethyl ketone, washed three times with 200g of 10% saturated saline, and the solvent was distilled off under reduced pressure to obtain sucrose fatty acid ester B1. The average degree of esterification of sucrose fatty acid ester B1 was 1.01.

[0074] (Production Example 2) Fatty acid ester B2 was obtained in the same manner as in Production Example 1, except that the amount of methyl stearate used was changed to 15.5 g. The average esterification degree of sucrose fatty acid ester B2 was 1.04.

[0075] (Production Example 3) Fatty acid ester B3 was obtained in the same manner as in Production Example 1, except that the amount of methyl stearate used was changed to 16.1 g. The average esterification degree of sucrose fatty acid ester B3 was 1.08.

[0076] (Production Example 4) Sucrose fatty acid ester B4 was obtained in the same manner as in Production Example 1, except that 13.6 g of methyl palmitate was used instead of methyl stearate. The average esterification degree of sucrose fatty acid ester B4 was 1.01.

[0077] (Production Example 5) Fatty acid ester B5 was obtained in the same manner as in Production Example 1, except that 10.8 g of methyl laurate was used instead of methyl stearate. The average esterification degree of sucrose fatty acid ester B5 was 1.01.

[0078] Example 1 0.15 g of cannabidiol (CBD, manufactured by Sigma-Aldrichs), 0.9 g of the sucrose fatty acid ester B1 obtained in Production Example 1, and 1 g of ethanol were mixed at 60°C to obtain raw material liquid 1. In a separate container, 0.4 g of dextrin having a cyclic structure (trade name: cluster dextrin, manufactured by Glico Nutrition Foods Co., Ltd.) and 8 g of water were mixed to obtain raw material liquid 2. Raw material liquids 1 and 2 were mixed at 60°C to obtain a mixture. This mixture was frozen in an ethanol low-temperature bath at -50°C, and then dried using a freeze dryer to obtain a powder.

[0079] Example 2 0.15g of cannabidiol (CBD, manufactured by Sigma-Aldrichs), 0.9g of sucrose fatty acid ester B1 obtained in Production Example 1, and 1g of ethanol were mixed at 60°C to obtain raw material liquid 1. In another container, 0.4g of dextrin having a cyclic structure (trade name: cluster dextrin, manufactured by Glico Nutrition Foods Co., Ltd.) and 8g of water were mixed to obtain raw material liquid 2. Raw material liquids 1 and 2 were mixed at 60°C, and then 0.05g of L-ascorbic acid (trade name: L(+)-ascorbic acid, manufactured by Nacalai Tesque Co., Ltd.) was further mixed to obtain a mixture. This mixture was frozen in an ethanol low-temperature bath at -50°C, and then dried using a freeze dryer to obtain a powder.

[0080] Example 3 A powder was obtained in the same manner as in Example 2, except that the amount of dextrin having a cyclic structure was changed to 0.2 g.

[0081] Example 4 A powder was obtained in the same manner as in Example 2, except that the amount of dextrin having a cyclic structure was changed to 0.6 g.

[0082] Example 5 A powder was obtained in the same manner as in Example 2, except that the amount of sucrose fatty acid ester B1 used was changed to 0.6 g.

[0083] Example 6 A powder was obtained in the same manner as in Example 2, except that the amount of sucrose fatty acid ester B1 used was changed to 1.2 g.

[0084] Example 7 A powder was obtained in the same manner as in Example 2, except that 0.9 g of sucrose fatty acid ester B2 obtained in Production Example 2 was used instead of sucrose fatty acid ester B1.

[0085] Example 8 A powder was obtained in the same manner as in Example 2, except that 0.9 g of sucrose fatty acid ester B3 obtained in Production Example 3 was used instead of sucrose fatty acid ester B1.

[0086] Example 9 A powder was obtained in the same manner as in Example 2, except that 0.9 g of sucrose fatty acid ester B4 obtained in Production Example 4 was used instead of sucrose fatty acid ester B1.

[0087] Example 10 A powder was obtained in the same manner as in Example 2, except that 0.9 g of sucrose fatty acid ester B5 obtained in Production Example 5 was used instead of sucrose fatty acid ester B1.

[0088] Comparative Example 1 A powder was obtained in the same manner as in Example 1, except that 0.4 g of α-cyclodextrin (product name: α-cyclodextrin, manufactured by Kanto Chemical Co., Ltd.) was used instead of the dextrin having a cyclic structure.

[0089] Comparative Example 2 A powder was obtained in the same manner as in Example 1, except that 0.4 g of β-cyclodextrin (product name: β-cyclodextrin, manufactured by Kanto Chemical Co., Ltd.) was used instead of the dextrin having a cyclic structure.

[0090] Comparative Example 3 A powder was obtained in the same manner as in Example 1, except that 0.4 g of γ-cyclodextrin (product name: γ-cyclodextrin, manufactured by Kanto Chemical Co., Ltd.) was used instead of the dextrin having a cyclic structure.

[0091] (evaluation) The compositions (powders) obtained in each of the Examples and Comparative Examples were evaluated for appearance, average particle size, redispersibility, total light transmittance after redispersion, and coloration by the methods described below.

[0092] <Appearance evaluation of powder> The appearance of the powder obtained in each of the Examples and Comparative Examples was visually inspected and evaluated based on the following criteria. A: No agglomerates were observed and the powder was in good condition. B: A small amount of granular aggregates were observed, but the level was not problematic for practical use. C: Many aggregates and lumps were observed and powderization was not possible.

[0093] <Average particle size of powder> The volume average particle size (D50) of the powders obtained in each of the Examples and Comparative Examples was measured using a particle size distribution measuring device (product name: MT3000II, manufactured by Microtrackbell Co., Ltd.) For powders with an appearance rating of "C", the average particle size could not be measured.

[0094] <Evaluation of powder redispersibility> A water dispersion of the powder obtained in each Example and Comparative Example was prepared. Specifically, the powder was added to pure water stirred with a stirrer so that the CBD concentration was 0.1% by mass, and the solution was stirred for 3 minutes to prepare an aqueous solution. In addition, an acidic aqueous solution was prepared by using an aqueous citric acid solution (pH 3.4) instead of water. The obtained aqueous solution and acidic aqueous solution were left to stand for 5 minutes, and then visually observed to evaluate the redispersibility of the powder based on the following criteria. A: No precipitate was observed, and the redispersibility was very good. B: Precipitation was observed, and redispersibility was poor.

[0095] <Transparency> The total light transmittance of the aqueous solution and the acidic aqueous solution prepared for the powder redispersibility evaluation was measured at 25°C using a haze meter NDH4000 (manufactured by Nippon Denshoku Industries Co., Ltd.) and evaluated based on the following criteria. A higher total light transmittance indicates higher transparency. A: Total light transmittance was 95% or more. B: The total light transmittance was 90% or more and less than 95%. C: The total light transmittance was 85% or more and less than 90%. D: The total light transmittance was 80% or more and less than 85%. E: The total light transmittance was less than 80%.

[0096] <Coloring 1> The aqueous solution and acidic aqueous solution prepared in the same manner as in the powder redispersibility evaluation were irradiated with ultraviolet light (light source model: SX-UID502HUV, lamp type: ultra-high pressure UV lamp 500W, manufactured by Ushio Inc.) at 25°C for 30 minutes. After ultraviolet irradiation, the sample was placed in a colorimeter and the Hazen color number (APHA) was measured using a spectrophotometer SE6000 (manufactured by Nippon Denshoku Industries Co., Ltd.). The lower the APHA value, the less colored the sample was. A:APHA was less than 20. B: APHA was 20 or more and less than 40. C: APHA was 40 or more and less than 60. D: APHA was greater than 60 and less than 80. E:APHA was 80 or higher.

[0097] <Coloring 2> Except for changing the ultraviolet irradiation time to 60 minutes, the Hazen color number (APHA) was measured in the same manner as in Coloring 1. The evaluation was performed according to the same criteria as in Coloring 1.

[0098] Table 1 shows the composition conditions and evaluation results of each of the examples and comparative examples. Note that blank spaces in Table 1 indicate that the corresponding raw material was not used.

[0099] From the results in Table 1, it was found that the composition (powder) containing the cannabinoid (A), sucrose fatty acid ester (B) and dextrin having a cyclic structure (C) had few aggregates, was excellent in redispersibility in an aqueous medium, and was excellent in redispersibility even under acidic conditions. It was also found that the composition of the present invention was suppressed in coloration, and was excellent in dispersibility and transparency, and these effects were excellent even under acidic conditions.

[0100] [Table 1]

Claims

1. The present invention comprises a cannabinoid (A), a sucrose fatty acid ester (B), and a dextrin having a cyclic structure (C), A composition, wherein the cyclic structure is composed of 10 to 500 glucose units.

2. The composition according to claim 1, comprising 5 to 150 parts by mass of the dextrin having a cyclic structure (C) relative to 100 parts by mass of the sucrose fatty acid ester (B).

3. The composition according to claim 1 or 2, wherein the sucrose fatty acid ester (B) has an average degree of esterification of 1.00 to 1.

15.

4. 3. The composition according to claim 1 or 2, which is in powder form.

5. The composition according to claim 1 or 2, which is for food, cosmetic, feed or pharmaceutical use.

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