JP7202492B1 - O/D type emulsion composition - Google Patents

Abstract

The object of the present invention is to provide a composition in which cannabinoids are excellent in dispersibility and in which oxidative deterioration of cannabinoids is unlikely to occur. The O/D emulsified composition of the present invention is an O/D emulsified composition in which an oil phase is emulsified in a D phase, the oil phase contains a cannabinoid, and the D phase is Contains an alcohol compound and a surfactant. The oil phase preferably contains an edible oil, and the surfactant preferably contains a sucrose fatty acid ester. According to the O/D emulsion composition of the present invention, the dispersibility of cannabinoids can be improved, and the oxidative deterioration of cannabinoids is less likely to occur. [Selection figure] None

Description

The present invention relates to an O/D emulsion composition.

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

JP-A-6-145598

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 to foods and formulations, for example. In addition, since cannabinoids are easily oxidatively degraded, there has been a demand for technical development to suppress oxidative degradation in addition to improving dispersibility.

The present invention has been made in view of the above, and an object of the present invention is to provide a composition which is excellent in dispersibility of cannabinoids and in which oxidative deterioration of cannabinoids is less likely to occur.

The inventors of the present invention have conducted intensive studies to achieve the above objects, and found that the D-phase emulsification of cannabinoids can improve the dispersibility of cannabinoids. We have found that it can be suppressed, and have completed the present invention.

That is, the present invention includes, for example, the subject matter described in the following sections.
Item 1
An O/D emulsion composition obtained by emulsifying an oil phase in a D phase,
The oil phase contains cannabinoids,
The O/D emulsion composition, wherein the D phase contains an alcohol compound and a surfactant.
Item 2
Item 2. The O/D emulsion composition according to Item 1, wherein the oil phase contains an edible oil.
Item 3
Item 3. The O/D emulsion composition according to Item 1 or 2, wherein the surfactant contains a sucrose fatty acid ester.
Item 4
The O/D emulsion composition according to any one of Items 1 to 3, wherein the sucrose fatty acid ester has an average degree of esterification of 1.0 to 1.3.
Item 5
Item 5. The O/D emulsion composition according to any one of items 1 to 4, wherein the cannabinoid comprises cannabidiol.
Item 6
Item 6. The O/D emulsion composition according to any one of items 1 to 5, which is used for food, cosmetics, feed, or medicine.

The O/D emulsified composition of the present invention has excellent dispersibility of cannabinoids, and is less prone to oxidative deterioration of cannabinoids.

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".

The O/D emulsion composition of the present invention is obtained by emulsifying an oil phase into a D phase, the oil phase containing a cannabinoid, and the D phase containing an alcohol compound and a surfactant. According to such an O/D emulsion composition, the dispersibility of cannabinoids can be improved, and the oxidative deterioration of cannabinoids is less likely to occur.

O / D type emulsion is obtained by an emulsification method (referred to as D phase emulsification method) using a surfactant phase, so-called D phase (detergent phase), and O phase (i.e., oil phase ) is, for example, an emulsion dispersed as fine droplets. It is also known that a fine O/W emulsion can be obtained by mixing this O/D emulsion with an aqueous phase.

(oil phase)
In the O/D emulsion composition of the present invention, the oil phase contains at least cannabinoids. As cannabinoids, for example, one or more of various compound groups (specifically, cannabidiol (CBD), tetrahydrocannabinol, etc.) contained in hemp-derived cannabinoids can be used.

Among them, the cannabinoid preferably contains cannabidiol. In this case, the dispersibility of the oil phase in the D phase is likely to be improved, and oxidative deterioration is less likely to occur. Easy to apply in the field.

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 oil phase preferably contains an edible oil. In this case, the oil phase is particularly excellent in dispersibility in the D phase, and oxidative deterioration is less likely to occur. It is particularly easy to apply in the pharmaceutical field.

Edible oils include synthetic oils such as medium-chain fatty acid triglycerides represented by MCT oil, cottonseed oil, castor oil, soybean oil, rapeseed oil, corn oil, olive oil, palm oil, safflower oil, rice oil, sunflower oil. vegetable oils such as oil and sesame oil; and animal oils such as lard, beef tallow, milk fat and fish oil. As edible oils and fats, for example, commercially available products can be widely used. The edible oils and fats contained in the oil phase can be used alone or in combination of two or more.

When the oil phase contains edible fats and oils, the content is not particularly limited. For example, the content of edible oil is preferably 50 parts by mass or more, more preferably 60 parts by mass or more, and even more preferably 70 parts by mass or more, relative to the total mass of cannabinoids of 100 parts by mass. Also, it is preferably 300 parts by mass or less, more preferably 200 parts by mass or less, even more preferably 150 parts by mass or less, and particularly preferably 120 parts by mass or less.

The oil phase may contain components other than cannabinoids and edible oils and fats as long as the effects of the present invention are not inhibited, or the oil phase may contain only cannabinoids and edible oils and fats. Examples of components other than cannabinoids and edible oils and fats include, for example, various components contained in the oil phase of known O/D emulsions, such as fatty acids, waxes, and fat-soluble vitamins. .

(D phase)
Phase D is a phase containing an alcohol compound and a surfactant, and particularly a phase that functions as a medium for dispersing the oil phase.

Examples of the surfactant contained in the D phase include a wide range of various emulsifiers used in the D phase of known O/D emulsions. In the present invention, the surfactant has a molecular weight of 200 or more.

Examples of surfactants include sucrose fatty acid esters, and synthetic surfactants such as sorbitan fatty acid esters, polyglycerin fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyglycerin condensed ricinoleic acid esters, and propylene glycol fatty acid esters. Agents; Phospholipids, glycolipids, enzyme-treated egg yolks, saponins, plant sterols, non-synthetic surfactants such as milk fat globule membranes, and the like. The surfactant contained in the D phase can be used alone or in combination of two or more.

Among them, the surfactant contained in the D phase preferably contains a sucrose fatty acid ester. In this case, the oil phase is easily dispersed in the D phase, and the oxidative deterioration of cannabinoids is less likely to occur. Easy to apply in the field. The surfactant contained in phase D may be sucrose fatty acid ester alone.

The type of sucrose fatty acid ester is not particularly limited, and for example, a wide range of known sucrose fatty acid esters can be used. As a reminder, as used herein, "sucrose fatty acid ester" means an ester compound of sucrose and fatty acid.

In the present invention, the sucrose fatty acid ester preferably has an average degree of esterification of 1.0 to 1.3. In this case, the oil phase is particularly easily dispersed in the D phase, and oxidative deterioration of cannabinoids is particularly difficult to occur. , easy to apply in the pharmaceutical field.

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 1.25 or less, more preferably 1.2 or less, and particularly preferably 1.15 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 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. .

In the sucrose fatty acid ester, the type of fatty acid moiety (RCOO-site) is not particularly limited. The fatty acid portion of the sucrose fatty acid ester may be a saturated fatty acid-derived portion or an unsaturated fatty acid-derived portion, preferably a saturated fatty acid-derived portion.

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 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.

The content of the surfactant contained in the D phase is not particularly limited. For example, the content of the surfactant contained in the O/D type emulsified composition of the present invention is 5 parts by mass or more with respect to 100 parts by mass of the cannabinoid in terms of easily increasing dispersibility and easily suppressing oxidative deterioration. preferably 6 parts by mass or more, more preferably 7 parts by mass or more, preferably 50 parts by mass or less, more preferably 40 parts by mass or less, It is more preferably 35 parts by mass or less, and particularly preferably 30 parts by mass or less.

As the alcohol compound contained in the D phase, a wide range of alcohol compounds contained in the D phase of known O/D emulsions can be used. Examples of alcohol compounds include polyhydric alcohols and monoalcohols. In the present invention, the alcohol compound has a molecular weight of 40 or more and less than 200. The alcohol compound can, for example, serve as a bridge between the oil phase and the D phase.

The alcohol compound contained in phase D preferably contains at least a polyhydric alcohol. In this case, the oil phase is easily dispersed in the D phase, and the oxidative deterioration of cannabinoids is less likely to occur. Easy to apply in the field. The alcohol compound contained in phase D may be a mixture of polyhydric alcohol and monoalcohol, or the alcohol compound may be polyhydric alcohol alone.

Examples of polyhydric alcohols include compounds having two or more hydroxyl groups in the molecule, and examples thereof include glycerin and propylene glycol, and other polyglycerins such as diglycerin, triglycerin, and tetraglycerin; glucose, maltose, multi- saccharides such as tall, sucrose, fructose, xylitol, inositol, pentaerythritol, sorbitol, maltotriose, starch-decomposing sugar; Among them, the polyhydric alcohol is preferably one or more selected from the group consisting of glycerin, D-sorbitol and propylene glycol in terms of excellent oil phase dispersibility and easy suppression of acid value deterioration of cannabinoids. More preferably it contains glycerin. Polyhydric alcohols may be used singly or in combination of two or more.

A monoalcohol is a compound having one hydroxyl group in the molecule, and includes, for example, ethanol, isopropanol, etc., preferably ethanol. Monoalcohols may be used singly or in combination of two or more.

The content of the alcohol compound contained in the D phase is not particularly limited. For example, the content of the alcohol compound contained in the O/D emulsified composition of the present invention is preferably 100 parts by mass or more with respect to 100 parts by mass of the cannabinoid, and 125 parts by mass, in terms of easily increasing the dispersibility. It is more preferably 150 parts by mass or more, more preferably 1000 parts by mass or less, more preferably 800 parts by mass or less, and 600 parts by mass or less. is more preferable, and 500 parts by mass or less is particularly preferable.

When the alcohol compound contained in the D phase is a mixture of a polyhydric alcohol and a monoalcohol, the ratio of the two is not particularly limited. is preferably 15% by mass or less, more preferably 10% by mass or less.

In the D phase, the proportion of the alcohol compound and the surfactant present is not particularly limited as long as the effects of the present invention are not inhibited. It is preferably contained, more preferably 1 to 15 parts by mass of the surfactant, and even more preferably 2 to 10 parts by mass of the surfactant.

The D phase may contain components other than the alcohol compound and the surfactant as long as the effects of the present invention are not inhibited, or the D phase may consist of the alcohol compound and the surfactant only.

(O/D type emulsion composition)
The O/D type emulsified composition of the present invention is formed of the oil phase and the D phase.

In the O/D emulsion composition of the present invention, the cannabinoid content is not particularly limited. For example, when the total mass of cannabinoids, edible fats and oils, surfactants and alcohol compounds is S, the content of cannabinoids is preferably 5% by mass or more, preferably 10% by mass or more, relative to the total mass S. is more preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less.

In the O/D emulsion composition of the present invention, when the oil phase contains edible fats and oils, the content is not particularly limited. For example, in the O/D emulsion composition of the present invention, the content of the edible oil is preferably 5% by mass or more, more preferably 8% by mass or more, more preferably 10% by mass, relative to the total mass S % or more, preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 20% by mass or less.

The content of the surfactant in the O/D emulsion composition of the present invention is not particularly limited. For example, in the O/D emulsion composition of the present invention, the content of the surfactant is preferably 0.5% by mass or more, more preferably 1% by mass or more, relative to the total mass S. Also, it is preferably 10% by mass or less, more preferably 8% by mass or less, and even more preferably 5% by mass or less.

The O/D type emulsified composition of the present invention can contain other components other than cannabinoids, edible fats and oils, surfactants and alcohol compounds as long as the effects of the present invention are not inhibited. Examples of other ingredients include various ingredients widely used in food applications and various ingredients widely used in pharmaceutical applications. When the O/D emulsion composition of the present invention contains the other component, the content is, for example, 50% by mass or less, preferably 30% by mass or less, more preferably 20% by mass, relative to the total mass of the composition. Below, more preferably 10% by mass or less, particularly preferably 1% by mass or less.

In the O/D emulsion composition of the present invention, the average particle size of the oil droplets constituting the oil phase is not particularly limited. For example, the median diameter (D50) of the oil droplets constituting the oil phase is 2 μm or less. is preferably 1.8 μm or less, more preferably 1.5 μm or less, particularly preferably 1 μm or less, and preferably 0.1 μm or more, and 0.2 μm or more. and more preferably 0.3 μm or more. The median diameter (D50) means the particle diameter D50 at which the cumulative frequency is 50% in the scattering intensity distribution.

The average particle size of the oil droplets of the O/D emulsion composition of the present invention is a value measured by a laser diffraction scattering method using a particle size measuring device (trade name: SALD-2300, manufactured by Shimadzu Corporation). It means a value measured according to the method described in Examples in particular.

The O/D type emulsified 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. 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 O/D emulsified composition of the present invention can be particularly preferably used as, for example, food additives, feed additives, pharmaceutical additives, and cosmetic additives.

An O/W emulsion can be obtained by using the O/D emulsion composition of the present invention. The method for obtaining the O/W emulsion is not particularly limited. For example, the O/W emulsion can be obtained by mixing an aqueous solvent such as water with the O/D emulsion composition of the present invention. Such an O/W emulsion can also be applied to the various uses and additives described above.

The method for producing the O/D emulsion composition of the present invention is not particularly limited, and for example, the same production methods as those for known O/D emulsion compositions can be widely adopted. For example, an O/D emulsion composition of the present invention is obtained by adding an oil phase containing a cannabinoid to phase D prepared using an alcohol compound containing a surfactant and emulsifying (so-called D phase emulsification). Obtainable.

In the D-phase emulsification, it is preferable to add the oil phase containing the cannabinoid dropwise to the D-phase. In this case, for example, the oil phase is preferably added dropwise at a rate of 1 to 50 mass parts/minute, more preferably 5 to 25 mass parts/minute, per 100 mass parts of the total mass of the D phase.

In the D-phase emulsification, the temperature of the D-phase is not particularly limited, and can be appropriately set in consideration of the boiling point of the alcohol compound contained in the D-phase. For example, in phase D emulsification, the temperature of phase D can be 20-150°C, preferably 30-100°C. Moreover, the method of emulsifying by adding the oil phase to the D phase is not particularly limited, and a wide range of known emulsifying means can be employed in the present invention.

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.

(material)
An O/D type emulsified composition in which an oil phase is emulsified in a D phase was prepared by selecting an appropriate raw material from the raw materials shown below.

<Cannabinoids>
· Cannabidiol; CBD, manufactured by Sigma-Aldrichs

<Edible oils and fats>
・MCT oil; Product name: Actor M-1, manufactured by Riken Vitamin Co. ・Cottonseed oil ・Castor oil

<Surfactant>
- Sucrose fatty acid ester A (degree of esterification: 1.01): Obtained according to Production Example 1 described later.
- Sucrose fatty acid ester B (degree of esterification: 1.04): Obtained according to Production Example 2 described later.
- Sucrose fatty acid ester C (degree of esterification: 1.10): Obtained according to Production Example 3 described later.
- Sucrose fatty acid ester D (degree of esterification: 1.20): Obtained according to Production Example 4 described later.
・Sorbitan fatty acid ester; NOF "Polysorbate 80 (HX2)"
・ Polyglycerin fatty acid ester: Taiyo Kagaku "Sunsoft A-14E-C"

<Alcohol compound>
・Glycerin ・D-sorbitol ・Ethanol ・Propylene glycol

(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 16.5 g. The average degree of esterification of sucrose fatty acid ester C was 1.10.

(Production example 4)
A fatty acid ester D 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)
An O/D type emulsified composition was prepared by selecting the raw materials shown in Example 1 of the recipe in Table 1. Specifically, 15 g of cannabidiol and 15 g of MCT oil are mixed at 70 ° C. to obtain an oil phase, while 2 g of sucrose fatty acid ester A and 68 g of glycerin are mixed at 70 ° C. in another container. Phase D was obtained. The D phase is maintained at 70° C., the oil phase is added dropwise thereto over 5 minutes, and emulsified (D phase emulsification) by a homogenizer at a rotation speed of 7000 rpm for 3 minutes to obtain an O/D emulsion composition. Obtained.

(Examples 2 to 20)
O/D emulsion compositions were obtained in the same manner as in Example 1, except that the types and blending amounts of the raw materials were changed as shown in Table 1.

(Comparative example 1)
A composition was prepared by selecting the raw materials shown in Comparative Example 1 of the formulation shown in Table 1. Specifically, 2 g of sucrose fatty acid ester A and 68 g of D-sorbitol were mixed in a container at 70 ° C., 30 g of cannabidiol was added at once, and a composition was obtained without emulsifying the D phase. .

(Comparative example 2)
A composition was obtained in the same manner as in Comparative Example 1 except that the types and blending amounts of the raw materials were changed as shown in Table 1.

(Comparative Example 3)
A composition was obtained in the same manner as in Example 5, except that the oil layer was added to the D phase all at once, and the D phase was not emulsified.

(Evaluation method)
Each evaluation of the compositions obtained in Examples and Comparative Examples was performed according to the following procedures.

<Presence or absence of precipitates and separation>
The composition immediately after production obtained in each example and comparative example was diluted 100 times with water to prepare a dispersion having a concentration of 1% by mass, and 15 g of the dispersion was sealed and stored in a 20 mL container. C., 25.degree. C. or 60.degree. After a predetermined period of time has passed since storage, the appearance of the dispersion was observed, and the presence or absence of precipitates and separation was evaluated according to the criteria below.
A: No deposit or separation was observed even after 30 days of storage.
B: Precipitate or separation was observed from 20 days to 30 days after storage.
C: Precipitate or separation was observed from 10 days to 20 days after storage.
D: A deposit or separation was observed by the 10th day of storage.
E: A deposit or separation was observed immediately after production.

<Median diameter (D50); immediately after production>
The composition immediately after production obtained in each example and comparative example was diluted 100 times with water to prepare a dispersion having a concentration of 1% by mass, and a particle size measuring device (trade name: SALD-2300, Shimadzu Corporation) was used. ), the median diameter of the dispersion (particle diameter at which the cumulative frequency reaches 50%: D50) was measured in an environment of 25°C.

<Chemiluminescence>
Chemiluminescence is "weak light generated when molecules in a reaction system change from an excited state to a ground state in a chemical reaction", and it captures material changes (oxidative degradation, chemical reaction) at the initial stage with high sensitivity. It is an analysis that can For this measurement, a chemiluminescence analyzer (CLA-FS4, manufactured by Tohoku Denshi Sangyo Co., Ltd.) and a temperature-enhanced sample chamber (CLS-SH1, manufactured by Tohoku Denshi Sangyo Co., Ltd.) were used. Using this measuring device, the compositions obtained in Examples and Comparative Examples were held at 20° C. for 20 seconds in an oxygen atmosphere with an oxygen flow rate of 50 mL/min, and then heated to 70° C. in 300 seconds ( 10° C./min) and held at 70° C. for 600 seconds before measuring.

<Backscattered light change rate>
The composition obtained in each example and comparative example immediately after production was diluted 100-fold with water to prepare a 1% by mass dispersion, and the backscattered light change rate was measured using this dispersion. The backscattered light change rate is a measurement of scattered reflected light and transmitted light, and the light intensity distribution in the height direction is obtained while moving the sample tube containing the dispersion liquid up and down. Some measure changes in particle size as changes in light intensity distribution. For this measurement, a Turbiscan LAb THErmo (manufactured by Eko Seiki Co., Ltd.) was used, and after standing the sample tube containing the dispersion in the apparatus at 25 ° C. for 30 minutes, the height range of 43 mm from the bottom of the sample tube At , scans were taken every 10 minutes and measured over 8 hours. From this measurement, measurements of the backscattered light change rate of creaming sites (38-43 mm height area) and sedimentation sites (1.3-3 mm height area) were recorded.

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 O/D emulsified compositions obtained in Examples are excellent in dispersibility of cannabinoids, and moreover, the oxidative deterioration of cannabinoids is less likely to occur. It was found from the results of the backscattered light change rate. In Comparative Examples 1 to 3, the dispersibility of the cannabinoid was poor because D-phase emulsification was not performed. In addition, it is also clear from the results of chemiluminescence measurement (under oxygen conditions) that the O/D emulsion compositions obtained in the examples are less prone to oxidative deterioration of cannabinoids than in the comparative examples. In addition, in the examples, in the chemiluminescence measurement, no peaks other than the oxidative degradation peculiar to CBD were observed, and it was also demonstrated that the stability was high.

Claims (6)

An O/D emulsion composition obtained by emulsifying an oil phase in a D phase,
The oil phase contains cannabinoids,
The O/D emulsion composition, wherein the D phase contains an alcohol compound and a surfactant. 2. The O/D emulsion composition according to claim 1, wherein said oil phase contains an edible oil. The O/D emulsion composition according to claim 1 or 2, wherein the surfactant contains at least one selected from the group consisting of sucrose fatty acid esters, sorbitan fatty acid esters and polyglycerol fatty acid esters . The O/D emulsion composition according to any one of claims 1 to 3, wherein the sucrose fatty acid ester has an average degree of esterification of 1.0 to 1.3. The O/D emulsion composition according to any one of claims 1 to 4, wherein said cannabinoid comprises cannabidiol. The O/D emulsion composition according to any one of claims 1 to 5, which is used for food, cosmetics, feed, or medicine.