JP7202440B1 - Composition, method for producing the same, and surfactant - Google Patents

Abstract

Kind Code: A1 A composition in which a cannabinoid can be easily dispersed in a solvent, is less likely to be colored even when dispersed in the solvent, and can enhance the dispersion stability of the cannabinoid in the solvent even at high temperatures; A method for producing the same and a surfactant are provided. A composition of the present invention comprises a cannabinoid and a sucrose fatty acid ester, and the sucrose fatty acid ester has an average degree of esterification of 1.00 to 1.15. INDUSTRIAL APPLICABILITY The composition of the present invention has excellent dispersibility of cannabinoids in solvents, is less likely to be colored even when dispersed in solvents, and has excellent dispersion stability in solvents even at high temperatures. [Selection figure] None

Description

TECHNICAL FIELD The present invention relates to a composition containing a sucrose fatty acid ester, a method for producing the same, and a surfactant containing a sucrose fatty acid ester.

Cannabinoids are found in cannabis leaves and seed coats and are known to have various components such as cannabidiol (CBD). Since cannabidiol has a unique effect, it is widely applied in the food field such as food additives and in the medical field such as formulations, and is a component with high utility value.

For example, U.S. Pat. No. 6,200,003 proposes a solubilizate combining curcumin and at least one cannabinoid, which makes it possible to give a clear mixture when mixed with water. and

Japanese Patent Publication No. 2021-524271

However, cannabinoids, especially cannabidiol, have poor dispersibility in aqueous solvents such as water. Dispersibility tends to decrease. When such clouding occurs, it becomes difficult to apply it to foods and formulations, and powderization becomes difficult.

The present invention has been made in view of the above, and can easily disperse cannabinoids in a solvent, is less likely to be colored even when dispersed in the solvent, and cannabinoids can be dispersed in the solvent even at high temperatures. An object of the present invention is to provide a composition capable of improving dispersion stability, a method for producing the same, and a surfactant.

As a result of intensive studies aimed at achieving the above object, the present inventors have found that the above object can be achieved by using a specific sucrose fatty acid ester as an essential component, and have completed the present invention.

That is, the present invention includes, for example, the subject matter described in the following sections.
Item 1
containing cannabinoids and sucrose fatty acid esters,
The composition, wherein the sucrose fatty acid ester has an average degree of esterification of 1.00 to 1.15.
Item 2
Item 2. The composition of Item 1, further comprising a solvent.
Item 3
Item 3. The composition of Item 2, wherein the solvent is an aqueous solvent.
Item 4
Item 1. The composition according to Item 1, which is in powder form.
Item 5
5. The composition of any one of Items 1-4, wherein the cannabinoid comprises cannabidiol.
Item 6
The composition according to any one of claims 1 to 5, which is used for food, cosmetics, feed, or medicine.
Item 7
A cannabinoid dispersing surfactant,
A cannabinoid-dispersing surfactant comprising a sucrose fatty acid ester having an average degree of esterification of 1.00 to 1.15.
Item 8
A method for producing a composition containing a cannabinoid and a sucrose fatty acid ester,
A method for producing a composition comprising a step of mixing a cannabinoid and a sucrose fatty acid ester having an average degree of esterification of 1.00 to 1.15.

The composition of the present invention can easily disperse the cannabinoid in the solvent, is less likely to be colored even when dispersed in the solvent, and enhances the dispersion stability of the cannabinoid in the solvent even at high temperatures. be able to.

In addition, by using the surfactant of the present invention, the cannabinoid can be easily dispersed in the solvent, and discoloration can be prevented even when dispersed. Moreover, by using the surfactant of the present invention, it is possible to obtain a dispersion in which cannabinoids are highly stable even at high temperatures.

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, embodiments of the present invention will be described in detail. In this specification, the expressions "contain" and "include" include the concepts of "contain", "include", "substantially consist of" and "consist only of".

1. Composition The composition of the present invention comprises a cannabinoid and a sucrose fatty acid ester, and the sucrose fatty acid ester has an average degree of esterification of 1.00 to 1.15. The composition of the present invention contains the specific sucrose fatty acid ester, for example, when the composition of the present invention is dispersed in a solvent, or the composition of the present invention is a dispersion containing a solvent such as a solvent When , the cannabinoid can be easily dispersed in the solvent, and even when dispersed in the solvent, coloration is unlikely to occur. Moreover, the composition of the present invention can disperse the cannabinoids in the solvent even at high temperatures, and is unlikely to aggregate. It is possible to provide a dispersion liquid excellent in

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

Preferably the cannabinoid comprises cannabidiol. In this case, it is particularly excellent in dispersibility in a solvent, especially an aqueous solvent, is easily pulverized, and is particularly easy to apply in the fields of foods, cosmetics, feeds, or pharmaceuticals. The cannabinoid preferably contains 50% by mass or more of cannabidiol, more preferably 80% by mass or more, still more preferably 90% by mass or more, and particularly preferably 95% by mass or more. The cannabinoid can also be cannabidiol alone.

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 also be produced by known methods, or commercially available cannabidiol can be applied to the composition of the present invention.

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, as described above. 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 reminder, as used herein, "sucrose fatty acid ester" means an ester compound of sucrose and fatty acid.

By containing a sucrose fatty acid ester having 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 It is highly resistant to coloration even when dispersed in a solvent, and its dispersion stability in a solvent is excellent even at high temperatures.

If the average degree of esterification of the sucrose fatty acid ester exceeds 1.15, the dispersibility of the cannabinoid in the solvent is significantly reduced, and only a dispersion with poor dispersion stability is obtained, making it difficult to apply to various applications. In addition, it is difficult to obtain a powder suitable for food and pharmaceutical applications due to an increase in aggregates.

The average degree of esterification of the sucrose fatty acid ester is preferably 1.01 or more. 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 the sucrose fatty acid ester can be calculated by the following formula (1).
(Ns−X)=(Nx)/(Ny)
= {(OHV)/(1000 x 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 known Ns, Nx, Ny, OHV, MwSug and MwFa into the above equation (1). Ns, Nx, Ny, OHV, MwSug and MwFa can be measured by known methods.

As can be seen from the 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 with different degrees of esterification.

In the composition of the present invention, when using a commercial product 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. For example, a wide range of known sucrose fatty acid esters can be applied to the composition of the present invention.

The type of fatty acid moiety in the sucrose fatty acid ester is not particularly limited. The fatty acid moiety of the sucrose fatty acid ester may be a saturated fatty acid-derived moiety or an unsaturated fatty acid-derived moiety, preferably a saturated fatty acid-derived moiety.

In the sucrose fatty acid ester, the number of carbon atoms in the fatty acid moiety is not particularly limited. For example, the number of carbon atoms in the fatty acid moiety (including ester carbon) is preferably 30 or less in terms of facilitating the dispersibility of cannabinoids. It is more preferably 25 or less, even more preferably 20 or less, and particularly preferably 18 or less. In addition, the number of carbon atoms (including ester carbon atoms) in the fatty acid moiety is preferably 8 or more, more preferably 10 or more, and even more preferably 12 or more, in terms of facilitating the dispersibility of cannabinoids. , 14 or more. 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 esters contained in the composition of the present invention may be any of their esters, and may contain not only one type but also two or all of them. In other words, the sucrose fatty acid ester in the composition of the present invention may contain one or more sucrose fatty acid esters selected from the group consisting of monoesters, diesters and triesters.

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

Sucrose used in the method for producing sucrose fatty acid esters may be synthesized, for example, by a known method, or sucrose can be obtained from commercial products. Sucrose may be obtained by recovering unreacted sucrose 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.

Fatty acids used in the method for producing sucrose fatty acid esters, for example, may be synthesized by known methods, or fatty acids can be obtained from commercial products.

The method for adjusting the average degree of esterification of the sucrose fatty acid ester is also not particularly limited, and for example, widely known methods can be adopted. For example, by preparing various synthesis conditions such as the ratio of sucrose and fatty acids or esters thereof used in the production of sucrose fatty acid esters, the type of fatty acid, and the esterification reaction conditions, the average of sucrose fatty acid esters obtained The degree of esterification can be controlled within the desired range.

In addition, the average degree of esterification is known, and by mixing two or more sucrose fatty acid esters with different average degrees of esterification, it is possible to obtain a sucrose fatty acid ester controlled to 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 contents of cannabinoids and sucrose fatty acid esters are not particularly limited. For example, from the viewpoint of easily improving the dispersion stability of cannabinoids in a solvent and easily exerting the effects of cannabinoids, the total mass of cannabinoids in the composition is 100 parts by mass. The amount is preferably 100 parts by mass or more, more preferably 300 parts by mass or more, still more preferably 500 parts by mass or more, particularly preferably 600 parts by mass or more, and 5000 parts by mass. It is preferably 3000 parts by mass or less, more preferably 2000 parts by mass or less, and particularly preferably 1500 parts by mass or less.

The composition of the present invention can contain other ingredients in addition to the cannabinoid and sucrose fatty acid ester, as long as the effects of the present invention are not inhibited. For example, the composition of the present invention may contain surfactants other than the sucrose fatty acid ester as long as the effects of the present invention are not inhibited. Examples of such surfactants include a wide range of known surfactants, such as sorbitan fatty acid esters and polyglycerin fatty acid esters. When containing other surfactants, the content may be, for example, 5 to 60 parts by mass, preferably 10 to 50 parts by mass, more preferably 100 parts by mass per 100 parts by mass of sucrose fatty acid ester. 15 to 40 parts by mass.

The composition of the present invention can contain various additives in addition to cannabinoids, sucrose fatty acid esters, and other surfactants. Examples of additives include various ingredients widely used in food applications and various ingredients widely used in pharmaceutical applications.

Specific additives include edible oil and alcohol. Preferred examples of edible oils include medium-chain fatty acid triglycerides represented by MCT oil, cottonseed oil, castor oil, and the like. Commercially available products, for example, can be widely used for MCT oil. The alcohol content is, for example, ethanol.

When the composition of the present invention contains edible oil, the content is preferably 20 parts by mass or more, more preferably 50 parts by mass or more, relative to 100 parts by mass of the total cannabinoid. , more preferably 100 parts by mass or more, particularly preferably 150 parts by mass or more, preferably 500 parts by mass or less, more preferably 400 parts by mass or less, and 300 parts by mass or less More preferably, it is particularly preferably 250 parts by mass or less.

When the composition of the present invention contains alcohol, the content is preferably 100 parts by mass or more, more preferably 500 parts by mass or more, relative to 100 parts by mass of the total mass of cannabinoids. , more preferably 1000 parts by mass or more, particularly preferably 1500 parts by mass or more, preferably 10000 parts by mass or less, more preferably 5000 parts by mass or less, and 3000 parts by mass or less is more preferable, and it is particularly preferable that it is 2000 parts by mass or less.

When the composition of the present invention contains components other than edible oil and alcohol, the content is, for example, 50% by mass or less, preferably 30% by mass or less, more preferably 30% by mass or less, relative to the total mass of the composition. It is 20% by mass or less, more preferably 10% by mass or less, and particularly preferably 1% by mass or less. The compositions of the present invention are

The composition of the present invention may be solid or liquid such as a dispersion.

When the composition of the invention is a dispersion, the composition of the invention may further contain a solvent. As such a solvent, an aqueous solvent is preferable because the dispersibility of cannabinoids (especially cannabidiol) is likely to increase. Examples of the aqueous solvent include lower alcohol compounds such as water, methanol, ethanol, and isopropanol, as well as polyhydric alcohol compounds such as glycerin. Solvents may be mentioned. The aqueous solvent is particularly preferably water, and in this case, the dispersibility of the cannabinoid and the dispersion stability at high temperatures are remarkably excellent.

When the composition of the present invention is a dispersion containing a solvent, the content ratio of the solvent to the cannabinoid and sucrose fatty acid ester is not particularly limited. For example, the content of cannabinoids and sucrose fatty acid esters with respect 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, 0.1 to 5 parts by mass It is more preferably 0.2 to 3 parts by mass, and particularly preferably 0.2 to 3 parts by mass.

Even when the composition of the present invention is a dispersion containing a solvent, it can contain the above-described edible oil and/or alcohol in the above-described amounts, and additives other than edible oil and alcohol can be added. can also contain

When the composition of the present invention is a solvent-containing dispersion, the median diameter (D50) of such dispersion is not particularly limited. For example, the median diameter (D50) of the dispersion liquid is preferably from 1 to 150 nm, more preferably from 1 to 100 nm, in that dispersion stability tends to be improved and powderization described later can be easily performed. It is more preferably 1 to 50 nm, and particularly preferably 1 to 20 nm. The median diameter (D50) of the dispersion can be measured by a dynamic light scattering method using a particle size analyzer (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.

When the composition of the present invention is a dispersion containing a solvent, it can be powdered by drying the solvent by an appropriate method. That is, the composition of the present invention may be in powder form. 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. Accordingly, one aspect of the present invention is a powder that is a dried product of the dispersion.

When the composition of the present invention is powder, 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, in that it can be suitably used as various additives. The volume average particle size of the powder can be measured using a particle size distribution analyzer (trade name: MT3000II, manufactured by Microtrack Bell). 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 aforementioned edible oil in the aforementioned amount, and can also contain additives other than edible oil. However, the alcohol content may volatilize during the powdering process.

As described above, the composition of the present invention contains a cannabinoid and a specific sucrose fatty acid ester, so when the composition of the present invention is dispersed in a solvent, or the composition of the present invention is the dispersion In this case, the cannabinoid can be easily dispersed in the solvent, and even if it is dispersed in the solvent, coloration is unlikely to occur. Moreover, the composition of the present invention can disperse the cannabinoids in the solvent even at high temperatures, and is unlikely to aggregate. Therefore, according to the composition of the present invention, it is possible to provide a dispersion of cannabinoids with excellent dispersion stability even at high temperatures. Conventionally, cannabinoids (especially cannabidiol) have sometimes deteriorated dispersion stability and become cloudy or precipitated when the dispersion reaches a high temperature state (for example, 60 ° C.), but the present invention The dispersion obtained from the composition has excellent dispersion stability of the cannabinoid even at high temperatures, is less likely to be colored, and has excellent storage stability.

In addition, since the composition of the present invention is excellent in the dispersion stability of cannabinoids when it is a dispersion, it is possible to increase the ratio (concentration) of cannabinoids compared to conventional compositions, and compositions containing cannabinoids at high concentrations can also be provided.

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 foods, cosmetics, feeds, pharmaceuticals, and the like. Whether the composition of the present invention is in the form of a dispersion or a powder, it can be used for the various uses described above. As used herein, the term "food" broadly includes beverages, supplements, health foods, functional foods, foods for beauty purposes, feeds for animals such as pets, and the like. Further, in the present specification, the term "for feed" broadly includes feeds that can be used in various livestock fields, and also includes feeds used in aquaculture. As used herein, the term “medicine” includes pharmaceuticals for administration or administration to humans as well as pharmaceuticals for administration or administration to animals. When the composition of the present invention is applied to foods, cosmetics or medicines, it includes cosmetic purposes in any of the uses.

As described above, the composition of the present invention can be particularly suitably used as, for example, food additives, feed additives, pharmaceutical additives, and cosmetic additives.

The method for producing the composition of the present invention is not particularly limited, and for example, it can be produced by various methods using cannabinoids and sucrose fatty acid esters. In particular, the composition of the present invention can be easily produced by the "composition production method A" described later.

2. Surfactant for dispersing cannabinoids The surfactant for dispersing cannabinoids of the present invention is a surfactant used for dispersing cannabinoids, and has an average degree of esterification of 1.00 to 1.15. including. Such a sucrose fatty acid ester is synonymous with the sucrose fatty acid ester contained in the composition of the present invention described above, and preferred embodiments are also the same.

In the surfactant of the present invention, the content of the sucrose fatty acid ester can be 50% by mass or more, preferably 70% by mass or more, more preferably 90% by mass or more, and particularly preferably 95% by mass or more. can do. The surfactant of the present invention may consist of only the sucrose fatty acid ester.

Since the surfactant of the present invention contains a sucrose fatty acid ester having an average degree of esterification of 1.00 to 1.15, it can be used as a surfactant when dispersing cannabinoids in a solvent. In particular, when the cannabinoid is dispersed in a solvent, particularly an aqueous solvent, in the presence of the surfactant of the present invention, the dispersibility of the cannabinoid in the solvent is excellent, and even if it is dispersed in the solvent, coloration is unlikely to occur. Dispersion stability in is excellent even at high temperatures.

Accordingly, the surfactants of the present invention are suitable for use in dispersing cannabinoids in solvents, particularly for dispersing cannabidiol in aqueous solvents.

The surfactant of the present invention can also contain surfactants other than the sucrose fatty acid esters, as long as the effects of the present invention are not inhibited. Examples thereof include sorbitan fatty acid esters and polyglycerol fatty acid esters. When the surfactant of the present invention contains a surfactant other than sucrose fatty acid ester, the content thereof is, for example, 5 to 60 parts by mass per 100 parts by mass of sucrose fatty acid ester, preferably It is 10 to 50 parts by mass, more preferably 15 to 40 parts by mass.

3. Method for producing a composition A method for producing the composition of the present invention (a composition containing a cannabinoid and a sucrose fatty acid ester) comprises a cannabinoid and a sucrose fatty acid ester having an average degree of esterification of 1.00 to 1.15. and mixing. Hereinafter, such a step will be referred to as step 1, and a manufacturing method including step 1 will be referred to as "manufacturing method A".

The cannabinoids and sucrose fatty acid esters having an average degree of esterification of 1.00 to 1.15 used in step 1 are synonymous with the cannabinoids and sucrose fatty acid esters contained in the composition of the present invention described above. Therefore, the cannabinoid used in step 1 is preferably cannabidiol.

The method of mixing the cannabinoid and the sucrose fatty acid ester in step 1 is not particularly limited. Examples thereof include a method of mixing solids such as powders, a method of mixing solids with raw material liquids such as solutions or dispersions, and a method of mixing raw material liquids.

For example, a method of mixing a raw material liquid containing a cannabinoid and a solvent with a raw material liquid containing a sucrose fatty acid ester and a solvent can be used. In this case, the solvent for dissolving or dispersing cannabinoids is not particularly limited, and known solvents used for dissolving or dispersing cannabinoids can be mentioned. Examples of such a solvent include various oils, for example, edible oils, among which medium-chain fatty acid triglycerides represented by MCT oil, cottonseed oil, castor oil, etc. can be preferably used. Commercially available products, for example, can be widely used for MCT oil.

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

The solvent for dissolving or dispersing the sucrose fatty acid ester is not particularly limited, and for example, a wide range of solvents used for dissolving or dispersing sucrose fatty acid esters can be mentioned. Examples of such solvents include lower alcohol compounds such as water, methanol, ethanol, and isopropanol, as well as polyhydric alcohol compounds such as glycerin. A mixed solvent can be mentioned. Among them, it is preferable to use a lower alcohol compound, and it is more preferable to use ethanol.

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

For example, when mixing a raw material solution containing a cannabinoid and a solvent, and a raw material solution containing a sucrose fatty acid ester and a solvent, the temperature during mixing is not particularly limited, for example, 20 to 100 ° C., preferably 30 to 90°C, more preferably 40-80°C. The mixing method is also not particularly limited, and for example, a wide range of known mixers can be used.

In the above production method A, for example, a solvent is further added to the mixture obtained by mixing the cannabinoid and the sucrose fatty acid ester in step 1 to prepare a dispersion containing the above-described cannabinoid and sucrose fatty acid ester. can. For example, by adding water to the mixture obtained by mixing the cannabinoid and the sucrose fatty acid ester in step 1, an aqueous dispersion containing the cannabinoid and the sucrose fatty acid ester is obtained. Moreover, in the manufacturing method A, the above-mentioned powder can be obtained by further subjecting the dispersion such as the aqueous dispersion to an appropriate drying treatment.

EXAMPLES 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.

(Production example 1)
400 g of DMSO and 34.2 g of sucrose were mixed and dissolved at 95° C. in a 1 L flask equipped with a stirrer, thermometer, vacuum device, and reflux device for dimethylsulfoxide (DMSO). 2.4 g of potassium carbonate and 15.0 g of methyl stearate as a fatty acid ester were added thereto and reacted at 95° C. for 3 hours under a reduced pressure of 2 kPa. Subsequently, after neutralization by adding lactic acid, DMSO was distilled off under reduced pressure. The resulting crude product was dissolved in 200 g of methyl ethyl ketone, washed three times with 200 g of 10% saturated brine, 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.

(Production 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.

(Production 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.

(Production example 4)
Fatty acid ester D 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 degree of esterification of sucrose fatty acid ester D was 1.01.

(Production 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.

(Production 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)
A raw material liquid 1 was obtained by mixing 0.1 g of cannabidiol (CBD, manufactured by Sigma-Aldrich) and 0.1 g of MCT oil (trade name: Acta M-1, manufactured by Riken Vitamin) at 70°C. In another container, 1.2 g of sucrose fatty acid ester A obtained in Production Example 1 as a surfactant and 1 g of ethanol were mixed at 70° C. to obtain raw material liquid 2 . A mixture was obtained by mixing raw material liquids 1 and 2 at 70°C. A composition was obtained by adding 100 mL of water to the resulting mixture.

(Example 2)
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 3)
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 0.6 g.

(Example 4)
A composition was obtained in the same manner as in Example 1 except that the sucrose fatty acid ester A was changed to the sucrose fatty acid ester B obtained in Production Example 2.

(Example 5)
A composition was obtained in the same manner as in Example 1 except that the sucrose fatty acid ester A was changed to the sucrose fatty acid ester C obtained in Production Example 3.

(Example 6)
A composition was obtained in the same manner as in Example 1 except that the sucrose fatty acid ester A was changed to the sucrose fatty acid ester D obtained in Production Example 4.

(Example 7)
A composition was obtained in the same manner as in Example 1 except that the sucrose fatty acid ester A was changed to the sucrose fatty acid ester E obtained in Production Example 5.

(Example 8)
Except that the surfactant was changed to a mixture of 0.9 g of sucrose fatty acid ester A and 0.3 g of sorbitan fatty acid ester (NOF "Polysorbate 80 (HX2)") to obtain raw material solution 2. A composition was obtained in the same manner as in Example 1.

(Example 9)
A raw material solution 2 was obtained by changing the surfactant to a mixture of 0.9 g of sucrose fatty acid ester A and 0.3 g of polyglycerin fatty acid ester ("Sunsoft A-14E-C" manufactured by Taiyo Kagaku). A composition was obtained in the same manner as in Example 1 except for the above.

(Example 10)
A composition was obtained in the same manner as in Example 1, except that MCT oil was changed to cottonseed oil.

(Example 11)
A composition was obtained in the same manner as in Example 1, except that castor oil was used instead of MCT oil.

(Example 12)
The composition was prepared in the same manner as in Example 1 except that the surfactant was changed to a mixture of 0.9 g of sucrose fatty acid ester A and 0.3 g of sucrose fatty acid ester D to obtain raw material liquid 2. got

(Comparative example 1)
A composition was obtained in the same manner as in Example 1 except that the sucrose fatty acid ester A was changed to the 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 sucrose fatty acid ester A was changed to sorbitan fatty acid ester (manufactured by NOF "Polysorbate 80 (HX2)").

(evaluation)
The dispersion stability and high-temperature (60° C.) dispersion stability of the compositions obtained in each of the examples and comparative examples were evaluated based on the following evaluations of <transparency> and <presence or absence of precipitates and separation>.

<Transparency>
Immediately after production of the composition (aqueous dispersion) obtained in each example and comparative example, 15 g was sealed and stored in a 20 mL container, and stored at rest in an environment of 10 ° C., 25 ° C. or 60 ° C., After a predetermined period of time, the appearance was observed and the transparency was evaluated according to the criteria below.
A: It was transparent even after 45 days of storage.
B: White turbidity was observed from 21 days to 45 days after storage.
C: White turbidity was observed from 7 days to 21 days after storage.
D: White turbidity was observed from 3 days to 7 days after storage.
E: White turbidity was observed from 1 day to 3 days after storage.
F: White turbidity was observed from immediately after production to the first day of storage.
G: Cloudiness was observed immediately after production.

<Presence or absence of precipitates and separation>
Immediately after production of the composition (aqueous dispersion) obtained in each example and comparative example, 15 g was sealed and stored in a 20 mL container, and stored at rest in an environment of 10 ° C., 25 ° C. or 60 ° C., After a predetermined period of time, the appearance was observed and the presence or absence of precipitates and separation was evaluated according to the following criteria.
A: No deposit or separation was observed even after 45 days of storage.
B: Precipitate or separation was observed from 21 days to 45 days after storage.
C: Precipitate or separation was observed from 7 days to 21 days after storage.
D: Precipitate or separation was observed from 3 days to 7 days after storage.
E: Precipitate or separation was observed from 1 day to 3 days after storage.
F: A deposit or separation was observed immediately after production and up to the first day of storage.
G: Precipitates or separation was observed immediately after production.

<Coloring>
15 g of the composition (aqueous dispersion) obtained in each example and comparative example was sealed and stored in a 20 mL container immediately after production, and stored at 10 ° C. or 25 ° C. in an environment for a predetermined period of time. After that, the appearance was observed and the presence or absence of coloring was evaluated according to the following criteria.
A: Colorless even after 45 days of storage.
B: Coloring was observed from 21 days to 45 days after storage.
C: Coloring was observed from 7 days to 21 days after storage.
D: Coloring was observed from 3 days to 7 days after storage.
E: Coloring was observed from 1 day to 3 days after storage.
F: Coloring was observed from immediately after production to the first day of storage.
G: Coloring was observed immediately after production.

<Median diameter (D50); immediately after production>
The composition (aqueous dispersion) immediately after production obtained in each example and comparative example was measured by a particle size measuring device (trade name: nanoSAQLA, manufactured by Otsuka Electronics Co., Ltd.) with a median diameter (accumulated frequency of 50%). Particle diameter: D50) was measured in an environment of 25°C.

<Median diameter (D50); 7 days after production>
Immediately after production of the composition (aqueous dispersion) obtained in each example and comparative example, 15 g of the composition (aqueous dispersion) was sealed and stored in a container with a capacity of 20 mL. D50) was measured using a particle size analyzer (trade name: nanoSAQLA, manufactured by Otsuka Electronics Co., Ltd.).

<Measurement of volume average particle size of powder>
The compositions (aqueous dispersions) obtained in Examples and Comparative Examples were freeze-dried at −50° C. using a freeze dryer (trade name: FDU-1100, manufactured by EYELA) to obtain powder. rice field. The particle size of the obtained powder was measured with a particle size distribution analyzer (trade name: MT3000II, manufactured by Microtrack Bell).

Table 1 shows the compounding conditions (all units are in grams) of the compositions of Examples and Comparative Examples, and the evaluation results. A blank in Table 1 means that the raw material was not used.

From the results in Table 1, the composition (aqueous dispersion) containing cannabinoids and sucrose fatty acid esters with a specific range of esterification degree has excellent dispersibility of cannabinoids, is less likely to be colored, and is in a high temperature state. However, the dispersion stability was excellent and coloration was less likely to occur. In addition, even at high temperature, the change in particle size (D50) was small and the storage stability was excellent. Furthermore, it was also found that the powder obtained from the aqueous dispersion has less agglomeration and a smaller volume average particle size.

Claims (8)

containing cannabinoids and sucrose fatty acid esters,
The composition, wherein the sucrose fatty acid ester has an average degree of esterification of 1.00 to 1.15. 2. The composition of claim 1, further comprising a solvent. 3. The composition of claim 2, wherein said solvent is an aqueous solvent. 2. The composition of claim 1, which is in powder form. A composition according to any preceding claim, wherein said cannabinoid comprises cannabidiol. The composition according to any one of claims 1 to 5, which is used for food, cosmetics, feed, or medicine. A cannabinoid dispersing surfactant,
A cannabinoid-dispersing surfactant comprising a sucrose fatty acid ester having an average degree of esterification of 1.00 to 1.15. A method for producing a composition containing a cannabinoid and a sucrose fatty acid ester,
A method for producing a composition comprising a step of mixing a cannabinoid and a sucrose fatty acid ester having an average degree of esterification of 1.00 to 1.15.