JP7360526B1 - Composition - Google Patents

Abstract

[Problem] To form a powder with few aggregates and excellent redispersibility in an aqueous medium, and furthermore, to form a powder with excellent redispersibility even under acidic conditions. Provides a composition that can be used. [Solution] The composition of the present invention includes a cannabinoid, a sucrose fatty acid ester, and a water-soluble polymer compound, and the sucrose fatty acid ester has an average degree of esterification of 1.00 to 1.15. . [Selection diagram] None

Description

The present invention relates to compositions containing cannabinoids.

Cannabinoids are contained in hemp leaves and seed coats, and are known to contain various components such as cannabidiol (CBD). Since cannabidiol has unique efficacy, it is widely applied in the food field, such as food additives, and the medical field, such as pharmaceutical preparations, and is a component with high utility value.

For example, Patent Document 1 proposes a solubilized product that combines curcumin and at least one cannabinoid, and such a solubilized product makes it possible to provide a mixture without turbidity when mixed with water. It is said that

Special Publication No. 2021-524271

However, cannabinoids, particularly cannabidiol, are difficult to powder, and, for example, there is a problem in that aggregates are likely to be mixed in the powder. In addition, once powdered, it is difficult to redisperse into an aqueous medium, so for example, when powder containing cannabinoids is used as an additive for food or pharmaceutical applications, the redispersibility is low. In some cases, uniform mixing was difficult.

The present invention has been made in view of the above, and it is possible to form a powder with few aggregates and excellent redispersibility in an aqueous medium. It is an object of the present invention to provide a composition that can form a powder with excellent redispersibility even when the powder is mixed.

As a result of intensive research to achieve the above object, the present inventors discovered that the above object could be achieved by using a specific sucrose fatty acid ester as an essential component together with a water-soluble polymer compound, and completed the present invention. I ended up doing it.

That is, the present invention includes, for example, the subject matter described in the following sections.
Item 1
Contains cannabinoids, sucrose fatty acid esters, and water-soluble polymer compounds,
The sucrose fatty acid ester has an average degree of esterification of 1.00 to 1.15.
Section 2
Item 2. The composition according to Item 1, wherein the water-soluble polymer compound is at least one selected from the group consisting of cellulose derivatives and polyvinylpyrrolidone.
Section 3
Item 3. The composition according to item 1 or 2, wherein the mass ratio of the sucrose fatty acid ester and the water-soluble polymer compound (sucrose fatty acid ester/water-soluble polymer compound) is 0.5 to 30.
Section 4
Item 3. The composition according to any one of Items 1 to 3, further comprising an oil or fat.
Section 5
5. The composition according to any one of items 1 to 4, further comprising a solvent.
Section 6
6. The composition according to item 5, wherein the solvent is an aqueous solvent.
Section 7
Item 5. The composition according to any one of Items 1 to 4, which is in powder form.
Section 8
Item 8. The composition according to any one of items 1 to 7, which is used for food, cosmetics, feed, or medicine.

The composition of the present invention can form a powder with few aggregates, and can also form a powder that has excellent redispersibility in an aqueous medium, and has excellent redispersibility even under acidic conditions. A powder can be formed.

Embodiments of the present invention will be described in detail below. Note that, in this specification, the expressions "contain" and "comprising" include the concepts of "containing", "containing", "consisting essentially of", and "consisting only".

1. Composition The composition of the present invention contains a cannabinoid, a sucrose fatty acid ester, and a water-soluble polymer compound, and the sucrose fatty acid ester has an average degree of esterification of 1.00 to 1.15. Since the composition of the present invention contains the specific sucrose fatty acid ester and a water-soluble polymer compound in a composition containing cannabinoids, it is possible to form a powder with few aggregates.

Furthermore, the composition of the present invention can form a powder that is excellent in redispersibility in an aqueous medium, and can also be formed into a powder that is excellent in redispersibility even under acidic conditions. As used herein, "acidic conditions" means that the pH of the emulsified composition is 7 or less, preferably 4 or less.

Therefore, when the composition of the present invention is used as a powdered additive, it is possible to maintain a good dispersion state.

(cannabinoid)
The cannabinoids contained in the composition of the present invention include, for example, one or more of various compound groups (specifically, cannabidiol (CBD), tetrahydrocannabinol, etc.) contained in cannabinoids derived from hemp. can be used.

Preferably, the cannabinoid includes cannabidiol. In this case, it has excellent dispersibility in solvents, particularly aqueous solvents, is easily powderized, and is especially easy to apply to the food, cosmetic, feed, or pharmaceutical fields. The cannabinoid preferably contains cannabidiol in an amount of 50% by mass or more, 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 can also be only one type of cannabidiol.

Cannabinoids can be produced, for example, by known methods. Alternatively, commercially available cannabinoids can be applied to the compositions of the invention. Similarly, cannabidiol can be produced, for example, by known methods, or commercially available cannabidiol can be applied to the composition of the invention.

(Sucrose fatty acid ester)
As mentioned above, the sucrose fatty acid ester contained in the composition of the present invention has an average degree of esterification in the range of 1.00 to 1.15. That is, the average degree of esterification of the sucrose fatty acid ester is 1.00 or more and 1.15 or less. As a precautionary note only, as used herein, "sucrose fatty acid ester" means a compound formed by an esterification reaction of sucrose and fatty acid.

By containing the sucrose fatty acid ester with an average degree of esterification of 1.00 to 1.15 in the composition, when the composition is dispersed in a solvent (especially an aqueous solvent), the dispersibility of cannabinoids in the solvent is improved. Furthermore, even if the composition is a powder, it has excellent dispersibility in a solvent (especially an aqueous solvent), and even when the solvent (especially an aqueous solvent) is under acidic conditions.

If the average degree of esterification of the sucrose fatty acid ester exceeds 1.15, a large number of aggregates will be formed when the composition is powdered, and the dispersibility of the powder in a solvent will also deteriorate.

The average degree of esterification of the sucrose fatty acid ester is preferably 1.01 or more. Further, the average degree of esterification of the sucrose fatty acid ester is preferably 1.12 or less, more preferably 1.10 or less, and particularly preferably 1.08 or less.

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

Here, the meaning of each symbol in formula (1) is as follows.
Ns: number of OH groups in one molecule of sucrose 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 group of sucrose fatty acid ester Value MwSug: Molecular weight of sucrose MwFa: Average molecular weight of constituent fatty acids

X can be calculated by substituting the known Ns, Nx, Ny, OHV, MwSug, and MwFa into the above equation (1). Note that Ns, Nx, Ny, OHV, MwSug, and MwFa can be measured by known methods.

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

In the composition of the present invention, when a commercial product is used as the sucrose fatty acid ester, the value disclosed by the manufacturer, such as the manufacturer's guaranteed value or catalog value of the sucrose fatty acid ester, can be adopted as the value of the average degree of esterification. .

The type of sucrose fatty acid ester 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.

In the sucrose fatty acid ester, the type of 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 an unsaturated fatty acid, preferably a moiety derived from a saturated fatty acid.

In the sucrose fatty acid ester, the number of carbon atoms in the fatty acid moiety of the sucrose fatty acid ester is not particularly limited, and for example, the number of carbon atoms in the fatty acid moiety (including ester carbons) is 30 or less in order to easily improve the dispersibility of cannabinoids. It is preferably at most 25, more preferably at most 20, even more preferably at most 18, and particularly preferably at most 18. In addition, in terms of easily increasing the dispersibility of cannabinoids, the number of carbon atoms in the fatty acid moiety (including ester carbons) is preferably 8 or more, more preferably 10 or more, and even more preferably 12 or more. , 14 or more is particularly preferred. The fatty acid moiety in the sucrose fatty acid ester is preferably derived from, for example, lauric acid, palmitic acid, stearic acid, or the like.

Sucrose fatty acid esters include monoesters, diesters, and triesters. The sucrose fatty acid ester contained in the composition of the present invention may be any of these esters, or may include not only one type, but also two or all of the esters. In other words, the sucrose fatty acid ester may contain one or more sucrose fatty acid esters selected from the group consisting of monoesters, diesters, and triesters.

The method for producing sucrose fatty acid ester is not particularly limited, and for example, a wide variety of known production methods can be employed. For example, sucrose fatty acid ester can be synthesized by a transesterification reaction between sucrose and fatty acid ester. Examples of fatty acid esters include methyl esters of fatty acids.

The sucrose used in the method for producing sucrose fatty acid ester may be synthesized, for example, by a known method, or may be obtained from a commercially available product. The sucrose may be recovered sucrose that was unreacted during the production of sucrose fatty acid ester (so-called "recovered sugar"). The form of 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, for example, by a known method, or may be obtained from a commercially available product.

The method for adjusting the average degree of esterification of sucrose fatty acid ester is also not particularly limited, and for example, a wide variety of known methods can be employed. For example, by adjusting various synthesis conditions such as the proportions of sucrose and fatty acids or their esters used in the production of sucrose fatty acid esters, the type of fatty acids, and the esterification reaction conditions, the average amount of sucrose fatty acid esters obtained can be adjusted. The degree of esterification can be controlled within a desired range.

In addition, by mixing two or more kinds of sucrose fatty acid esters having a known average degree of esterification and different average degrees of esterification, it is also possible to obtain a sucrose fatty acid ester controlled within a desired range. In this case, the average degree of esterification can be easily adjusted to a desired range based on the degree of esterification and the mixing mass ratio of each sucrose fatty acid ester.

In the composition of the present invention, the content ratio of sucrose fatty acid ester is not particularly limited. For example, when the composition is in the form of a powder, the dispersibility in a solvent tends to increase, so if the content of the sucrose fatty acid ester is 100 parts by mass or more when the total mass of cannabinoids in the composition is 100 parts by mass, It is preferably at least 300 parts by mass, even more preferably at least 500 parts by mass, particularly preferably at least 600 parts by mass, and preferably at most 5000 parts by mass, It is more preferably 3000 parts by mass or less, even more preferably 2000 parts by mass or less, and particularly preferably 1500 parts by mass or less.

The compositions of the present invention can include one or more sucrose fatty acid esters.

(Water-soluble polymer compound)
The water-soluble polymer compound contained in the composition of the present invention means a polymer compound that can be dissolved in water. For example, a water-soluble polymer compound can be a polymer compound that dissolves at least 0.1 part by mass in 100 parts by mass of water.

Examples of the water-soluble polymer compound that can be contained in the composition of the present invention include a wide range of known water-soluble polymer compounds, including cellulose derivatives, polyvinylpyrrolidone, and polyacrylic acid. or a salt thereof, polymethacrylic acid or a salt thereof, polyvinyl alcohol, polyalkylene oxide, polystyrene sulfonic acid or a salt thereof, and the like.

Among these, the water-soluble polymer compound is preferably at least one selected from the group consisting of cellulose derivatives and polyvinylpyrrolidone. In this case, even if the composition is a powder, aggregates are less likely to form, and the dispersibility in solvents (especially aqueous solvents) is better, even if the solvent (especially aqueous solvents) is under acidic conditions. It tends to have better dispersibility.

Examples of the cellulose derivatives include hydroxyalkylcellulose, and specific examples include hydroxymethylcellulose, hydroxyethylcellulose, and hydroxypropylcellulose.

The weight average molecular weight of the water-soluble polymer compound is not particularly limited, and can be, for example, in the range of 10,000 to 100,000.

The water-soluble polymer compound can be produced by a known method, or can be obtained from a commercially available product.

In the composition of the present invention, the content ratio of the water-soluble polymer compound is not particularly limited. For example, it is preferable that the mass ratio of the sucrose fatty acid ester to the water-soluble polymer compound is 0.5 to 30. That is, the composition of the present invention preferably has a value of "mass of sucrose fatty acid ester/amount of water-soluble polymer compound" of 0.5 to 30. In this case, even if the composition is a powder, aggregates are less likely to form, and the dispersibility in solvents (especially aqueous solvents) is better, even if the solvent (especially aqueous solvents) is under acidic conditions. It tends to have better dispersibility.

In the composition of the present invention, it is more preferable that the mass ratio of the sucrose fatty acid ester to the water-soluble polymer compound (mass of sucrose fatty acid ester/amount of water-soluble polymer compound) is 2 or more, It is more preferably 4 or more, particularly preferably 5 or more, more preferably 25 or less, even more preferably 20 or less, and particularly preferably 15 or less.

The composition of the present invention can contain one or more water-soluble polymer compounds.

(Other ingredients)
The composition of the present invention can contain other components in addition to cannabinoids and sucrose fatty acid esters, as long as the effects of the present invention are not inhibited. For example, the composition of the present invention can also contain a surfactant other than the sucrose fatty acid ester. Such surfactants include, for example, a wide variety of known surfactants, such as sorbitan fatty acid esters, polyglycerol fatty acid esters, and the like.

The composition of the present invention can also contain fats and oils. In this case, the dispersibility of cannabinoids is easily improved, so that the composition of the present invention can be easily applied to various additives in the food field, cosmetic field, feed field, or pharmaceutical field.

Examples of fats and oils include edible fats and oils, and specific examples include synthetic fats and oils such as medium-chain fatty acid triglycerides represented by MCT oil, as well as cottonseed oil, castor oil, soybean oil, rapeseed oil, corn oil, olive oil, Examples include vegetable oils and fats such as palm oil, safflower oil, rice oil, sunflower oil, and sesame oil; animal oils and fats such as lard, beef tallow, milk fat, and fish oil. For example, a wide variety of commercially available oils and fats can be used. The fats and oils contained in the composition can be used alone or in combination of two or more.

When the composition of the present invention contains oil and fat, the content thereof is preferably 20 parts by mass or more, more preferably 40 parts by mass or more, based on 100 parts by mass of the total mass of cannabinoids, for example, It is more preferably 60 parts by mass or more, particularly preferably 80 parts by mass or more, and preferably 500 parts by mass or less, more preferably 400 parts by mass or less, and 300 parts by mass or less. It is more preferable that the amount is 200 parts by mass or less, and particularly preferably 200 parts by mass or less.

The composition of the present invention may contain other additives, such as 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 thereof is, for example, 50% by mass or less, preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably is 10% by mass or less, particularly preferably 1% by mass or less.

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

When the composition of the present invention is a dispersion, the composition of the present invention can further include a solvent. As such a solvent, an aqueous solvent is preferable since the dispersibility of cannabinoids (especially cannabidiol) is easily increased and it is easy to dry and powderize. Examples of the aqueous solvent include water and alcohol.

Examples of the alcohol component include lower alcohol compounds such as methanol, ethanol, and isopropanol, as well as polyhydric alcohol compounds such as glycerin.

Examples of the aqueous solvent include a mixed solvent of water and the lower alcohol compound and/or the polyhydric alcohol compound; There may be. When the aqueous solvent contains a mixture of lower alcohols and polyhydric alcohols, examples include lower alcohols methanol, ethanol, isopropanol, etc., and examples of the polyhydric alcohol compound include glycerin.

When the composition of the present invention is a dispersion liquid, the aqueous solvent more preferably contains at least an alcohol component such as a lower alcohol compound and a polyhydric alcohol compound. In this case, after the composition is powdered, the dispersibility of such powder in a solvent (especially an aqueous solvent) becomes better, even if the solvent (especially an aqueous solvent) is under acidic conditions. It is easy to become excellent.

When the aqueous solvent contains an alcohol component containing 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. For example, the proportion of the polyhydric alcohol to 100 parts by mass of the lower alcohol compound The content of the compound is 10 to 50 parts by mass.

When the composition of the present invention is a dispersion containing an aqueous solvent, and the aqueous solvent contains an alcohol component such as a lower alcohol compound and a polyhydric alcohol compound, the content ratio of the alcohol component is, for example, less than the total mass of cannabinoids. It is preferably 100 parts by mass or more, more preferably 500 parts by mass or more, even more preferably 1000 parts by mass or more, and preferably 10000 parts by mass or less, based on 100 parts by mass. It is more preferably 5000 parts by mass or less, even more preferably 3000 parts by mass or less, and particularly preferably 2000 parts by mass or less.

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 cannabinoids and 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, and 0.1 to 5 parts by mass. Parts by weight are more preferable, and 0.2 to 3 parts by weight are particularly preferable.

When the composition of the present invention is a dispersion containing a solvent, the median diameter (D50) of such a dispersion is not particularly limited. For example, the median diameter (D50) of the dispersion liquid is preferably 1 to 150 nm, more preferably 1 to 100 nm, because the dispersion stability is likely to be good and the powdering described later can be easily performed. The thickness is more preferably 1 to 50 nm, even more preferably 1 to 20 nm. The median diameter (D50) of the dispersion liquid can be measured by dynamic light scattering 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 is 50% in the scattering intensity distribution.

The composition of the invention may be in powder form. In this case, the average particle size of the powder is not particularly limited. For example, the volume average particle diameter of the powder is preferably 0.1 to 500 μm, more preferably 1 to 150 μm, and more preferably 10 to 100 μm, since it can be suitably used as various additives. Particularly preferred. The volume average particle size of the powder can be measured using a particle size distribution measuring device (trade name: MT3000II, manufactured by Micro Track Bell Co., Ltd.). When the composition of the invention is a powder, such powder is, for example, composed of agglomerated particles.

Even when the composition of the present invention is a powder, it can contain the above-mentioned edible oil in the above-mentioned amount, and can also contain additives other than the edible oil. However, some or all of the above-mentioned aqueous solvents (for example, water and alcohol components such as lower alcohol compounds and polyhydric alcohol compounds) may volatilize during the powdering process. When the composition of the present invention is a powder, the content of lower alcohol compounds and polyhydric alcohol compounds contained in the powder is about 10 to 25% by mass.

When the composition of the present invention is a powder, the manufacturing method thereof is not particularly limited. For example, the composition of the present invention, which is a dispersion, can be powdered by drying the solvent using an appropriate method. . The method for drying the solvent is not particularly limited, and various known methods such as heat drying, spray drying, and freeze drying can be used. Therefore, one aspect of the present invention is 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 of cannabinoids dissolved in fat or oil.

Since the powder contains cannabinoids, specific sucrose fatty acid esters, and water-soluble polymer compounds, it has better dispersibility in solvents (especially aqueous solvents), and even if the solvent (especially aqueous solvents) is under acidic conditions. However, the dispersibility tends to be even better. 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, it is possible to increase the amount of powder added, that is, it is possible to increase the proportion (concentration) of cannabinoids than before, and compositions containing high concentrations of cannabinoids can be used. It is also possible to provide goods.

The composition of the present invention can be applied to various uses, and in particular, can be widely applied to uses to which compositions containing cannabidiol have been conventionally applied. Specifically, the composition of the present invention can be applied to food, cosmetics, feed, medicine, and the like. Regardless of whether the composition of the present invention is in the form of a dispersion or a powder, it can be used for the various purposes described above. In this specification, food products broadly include beverages, supplements, health foods, functional foods, foods for beauty purposes, feed for animals such as pets, and the like. Furthermore, in this specification, the term "for feed" broadly includes feeds that can be used in various livestock fields, and also includes feeds used for aquaculture. As used herein, "medicine" includes not only medicines to be taken or administered to humans, but also medicines to be taken or administered to animals. When the composition of the present invention is applied to food, cosmetics, or medicine, any of the uses includes those for cosmetic purposes.

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.

(Method for preparing composition)
The method for producing the composition of the present invention is not particularly limited, and it can be produced by various methods using, for example, cannabinoids, sucrose fatty acid esters, and water-soluble polymer compounds. For example, a method may be mentioned in which a raw material liquid containing cannabinoids and a raw material liquid containing a sucrose fatty acid ester and a water-soluble polymer compound are mixed in random order. The raw material liquid containing cannabinoids can contain various oils, such as the above-mentioned edible oils and fats, among which medium-chain fatty acid triglycerides such as MCT oil, cottonseed oil, castor oil, etc. can be preferably used. For example, a wide variety of commercially available MCT oils can be used.

The usage ratio of cannabinoid and solvent is not particularly limited, and for example, the amount of solvent used can be 50 to 200 parts by mass, preferably 80 to 150 parts by mass, per 100 parts by mass of cannabinoid.

The raw material solution containing the sucrose fatty acid ester and the water-soluble polymer compound can contain a solvent, and examples thereof include the aforementioned aqueous solvents (for example, water, lower alcohol compounds, polyhydric alcohol compounds, etc.). The polyhydric alcohol compound can also be added after mixing a raw material liquid containing cannabinoids and a raw material liquid containing sucrose fatty acid ester and a water-soluble polymer compound. The ratio of the sucrose fatty acid ester and the solvent used is not particularly limited, and for example, the amount of the solvent used can be 50 to 200 parts by mass, and 80 to 150 parts by mass per 100 parts by mass of the sucrose fatty acid ester. It is preferable to do so. Further, the usage ratio of the water-soluble polymer compound and the solvent is not particularly limited, and for example, the usage amount of the solvent can be 50 to 200 parts by mass, and 80 to 200 parts by mass per 100 parts by mass of the water-soluble polymer compound. The amount is preferably 150 parts by mass.

For example, when mixing a raw material liquid containing a cannabinoid and a solvent, a raw material liquid containing a sucrose fatty acid ester and a solvent, and a raw material liquid containing a water-soluble polymer compound and a solvent, the temperature at the time of mixing is also particularly limited. For example, the temperature is 20 to 100°C, preferably 30 to 90°C, more preferably 40 to 80°C. The mixing method is not particularly limited either, and for example, a wide variety of known mixers can be used. The concentration can also be adjusted by further adding water or the like to the composition obtained as described above.

As mentioned above, the composition obtained by mixing the raw material liquid containing cannabinoids and the raw material liquid containing sucrose fatty acid ester and a water-soluble polymer compound is powdered by performing an appropriate drying process as necessary. can do.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the embodiments of these Examples.

(Manufacturing example 1)
In a 1 L flask equipped with a stirrer, a thermometer, a pressure reduction device, and a dimethyl sulfoxide (DMSO) reflux device, 400 g of DMSO and 34.2 g of sucrose were mixed and dissolved at 95°C. To this, 2.4 g of potassium carbonate and 15.0 g of methyl stearate as a fatty acid ester were added, and the mixture was reacted at 95° C. for 3 hours under a reduced pressure of 2 kPa. 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 200 g of methyl ethyl ketone, washed three times with 200 g of 10% saturated saline, and the solvent was distilled off under reduced pressure to obtain sucrose fatty acid ester A. The average degree of esterification of sucrose fatty acid ester A was 1.01.

(Manufacturing example 2)
Fatty acid ester B 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 degree of esterification of sucrose fatty acid ester B was 1.04.

(Manufacturing example 3)
Fatty acid ester C 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 degree of esterification of sucrose fatty acid ester C was 1.08.

(Manufacturing example 4)
Fatty acid ester D was obtained in the same manner as in Production Example 1 except that 13.6 g of methyl parimitate was used instead of methyl stearate. The average degree of esterification of sucrose fatty acid ester D was 1.01.

(Manufacturing example 5)
Fatty acid ester E 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 degree of esterification of sucrose fatty acid ester E was 1.01.

(Manufacturing example 6)
Fatty acid ester F was obtained in the same manner as in Production Example 1 except that the amount of methyl stearate used was changed to 17.9 g. The average degree of esterification of sucrose fatty acid ester F was 1.20.

(Example 1)
Raw material liquid 1 was obtained by mixing 0.1 g of cannabidiol (CBD, manufactured by Sigma-Aldrichs) and 0.1 g of MCT oil (trade name: Actor M-1, manufactured by Riken Vitamin Co., Ltd.) as an oil and fat at 70 ° C. Ta. In another container, as a surfactant, 1.2 g of sucrose fatty acid ester A obtained in Production Example 1, 1 g of ethanol, and hydroxypropyl cellulose (product name: CELNY-SSL), a water-soluble polymer compound, are added. (weight average molecular weight 40,000, manufactured by Nippon Soda Co., Ltd.) 0.2 g at 70°C to obtain raw material liquid 2. A mixture was obtained by mixing raw material liquids 1 and 2 and 0.3 g of glycerin at 70°C. 24 g of water was added to this mixture, and the mixture was frozen in a −50° C. ethanol cold bath, and then dried using a freeze dryer to obtain a powder.

(Example 2)
A composition was obtained in the same manner as in Example 1, except that the amount of water-soluble polymer compound (HPC-SSL) used was changed to 0.1 g, and the amount of glycerin used was changed to 0.4 g.

(Example 3)
A composition was obtained in the same manner as in Example 1, except that a mixture of 0.2 g of HPC-SSL and 0.1 g of polyvinylpyrrolidone (PVP) was used as the water-soluble polymer compound.

(Example 4)
A composition was obtained in the same manner as in Example 1 except that the amount of water-soluble polymer compound (HPC-SSL) used was changed to 0.3 g.

(Example 5)
A composition was obtained in the same manner as in Example 1 except that 0.2 g of HPC-L (weight average molecular weight 140,000, manufactured by Nippon Soda Co., Ltd.) was used as the water-soluble polymer compound.

(Example 6)
A composition was obtained in the same manner as in Example 1, except that the water-soluble polymer compound was changed to 0.1 g of HPC-L (manufactured by Nippon Soda Co., Ltd.) and the amount of glycerin used was changed to 0.4 g. Ta.

(Example 7)
A composition was obtained in the same manner as in Example 1 except that 0.2 g of PVP was used as the water-soluble polymer compound.

(Example 8)
A composition was obtained in the same manner as in Example 1, except that the water-soluble polymer compound was changed to 0.1 g of PVP and the amount of glycerin used was changed to 0.4 g.

(Example 9)
A composition was obtained in the same manner as in Example 1 except that 0.3 g of PVP was used as the water-soluble polymer compound.

(Example 10)
A composition was obtained in the same manner as in Example 1 except that the water-soluble polymer compound was changed to 0.25 g of PVP and the amount of glycerin used was changed to 0.35 g.

(Example 11)
A composition was obtained in the same manner as in Example 1, except that sucrose fatty acid ester A was changed to sucrose fatty acid ester B obtained in Production Example 2.

(Example 12)
A composition was obtained in the same manner as in Example 1, except that sucrose fatty acid ester A was changed to sucrose fatty acid ester C obtained in Production Example 3.

(Example 13)
A composition was obtained in the same manner as in Example 1, except that sucrose fatty acid ester A was changed to sucrose fatty acid ester D obtained in Production Example 4.

(Example 14)
A composition was obtained in the same manner as in Example 1, except that sucrose fatty acid ester A was changed to sucrose fatty acid ester E obtained in Production Example 5.

(Example 15)
A composition was obtained in the same manner as in Example 1 except that the amount of sucrose fatty acid ester A used was changed to 0.9 g.

(Example 16)
A composition was obtained in the same manner as in Example 1 except that the amount of sucrose fatty acid ester A used was changed to 1.5 g.

(Example 17)
A composition was obtained in the same manner as in Example 1 except that MCT oil was changed to cottonseed oil.

(Example 18)
A composition was obtained in the same manner as in Example 1 except that MCT oil was changed to castor oil.

(Comparative example 1)
A composition was obtained in the same manner as in Example 1, except that sucrose fatty acid ester A was changed to sucrose fatty acid ester F obtained in Production Example 6.

(Comparative example 2)
A composition was obtained in the same manner as in Example 1, except that the surfactant was changed to 1.2 g of sorbitan fatty acid ester ("Polysorbate 80 (HX2)" manufactured by NOF Corporation).

(Comparative example 3)
A composition was obtained in the same manner as in Example 1, except that the surfactant was changed to 1.2 g of polyglycerin fatty acid ester ("Sunsoft A-14E-C" manufactured by Taiyo Kagaku).

(evaluation)
The appearance, average particle diameter, redispersibility, and total light transmittance after redispersion of the compositions (powders) obtained in each Example and Comparative Example were evaluated by the following methods.

<Powder appearance evaluation>
The appearance of the powder obtained in each Example and Comparative Example was visually observed and evaluated based on the following criteria.
A: No aggregates were observed, and the powder was good.
B: Slight granular aggregates were observed, but at a level that caused no practical problems.
C: Many aggregates and lumps were observed, and powdering was not possible.

<Average particle size of powder>
The volume average particle size (D50) of the powder obtained in each Example and Comparative Example was measured using a particle size distribution measuring device (trade name: MT3000II, manufactured by Micro Track Bell Co., Ltd.). It should be noted that the average particle diameter of the powder whose appearance evaluation was "C" could not be measured.

<Evaluation of redispersibility of powder>
An aqueous dispersion of the powder obtained in each Example and Comparative Example was prepared. Specifically, a sample was prepared by adding powder to a citric acid aqueous solution (pH 3.4) that was being stirred with a stirrer so that the CBD concentration was 0.1% by mass, and stirring for 3 minutes. The obtained sample was visually observed and the redispersibility of the powder was evaluated based on the following criteria.
A: No precipitate was observed, and very good redispersibility was observed.
B: Precipitates were observed, and redispersibility was poor.

<Total light transmittance>
The total light transmittance of samples prepared for powder redispersibility evaluation was measured at 25° C. using a hazemeter NDH4000 (manufactured by Nippon Denshoku Kogyo Co., Ltd.), and evaluated based on the following criteria.
A: Total light transmittance was 95% or more.
B: Total light transmittance was 90% or more and less than 95%.
C: Total light transmittance was 85% or more and less than 90%.
D: Total light transmittance was 80% or more and less than 85%.
E: Total light transmittance was less than 80%.

<Total light transmittance>
A sample was prepared by redispersing the powder obtained in each example and comparative example in a citric acid aqueous solution with a pH of 3.4, and the total light transmittance was measured at 25°C using a haze meter NDH4000 (manufactured by Nippon Denshoku Industries). and evaluated based on the following criteria.
A: Total light transmittance was 95% or more.
B: Total light transmittance was 90% or more and less than 95%.
C: Total light transmittance was 85% or more and less than 90%.
D: Total light transmittance was 80% or more and less than 85%.
E: Total light transmittance was less than 80%.

Table 1 shows the formulation conditions and evaluation results of the compositions of each Example and Comparative Example. Note that a blank column in Table 1 means that the raw material was not used.

From the results in Table 1, the composition (powder) containing at least a cannabinoid, a specific sucrose fatty acid ester, and a water-soluble polymer compound has fewer aggregates and is also excellent in redispersibility in an aqueous medium. It was also found that it has excellent redispersibility even under acidic conditions.

Claims (6)

Contains cannabinoids, sucrose fatty acid esters, and water-soluble polymer compounds,
The sucrose fatty acid ester has an average degree of esterification of 1.01 to 1.15,
The water-soluble polymer compound is at least one selected from the group consisting of cellulose derivatives and polyvinylpyrrolidone,
A composition in which the mass ratio of the sucrose fatty acid ester and the water-soluble polymer compound (sucrose fatty acid ester/water-soluble polymer compound) is 0.5 to 30. The composition according to claim 1, further comprising an oil or fat. The composition according to claim 1 or 2, further comprising a solvent. 4. The composition of claim 3, wherein the solvent is an aqueous solvent. The composition according to claim 1 or 2, which is in powder form. The composition according to claim 1 or 2, which is used for food, cosmetics, feed, or medicine.