JP7216234B1 - emulsion composition - Google Patents

Abstract

The object of the present invention is to provide a composition that exhibits excellent dispersibility of cannabinoids even under acidic conditions, and in which oxidative deterioration of cannabinoids does not readily occur. The emulsified composition of the present invention is an emulsified composition containing a cannabinoid and a surfactant, wherein the surfactant contains an organic acid monoglyceride. The emulsified composition of the present invention is preferably an O/D emulsion obtained by emulsifying an oil phase with a D phase, the oil phase contains the cannabinoid, and the D phase contains an alcohol compound and the surfactant containing agents. [Selection figure] None

Description

The present invention relates to emulsion compositions.

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. In particular, cannabinoids such as cannabidiol have the problem that under acidic conditions, their dispersibility is significantly reduced and a large amount of aggregates are generated. When such clouding and aggregate generation occurs, it becomes difficult to apply cannabinoids to food and pharmaceutical applications, 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 it is an object of the present invention to provide a composition that exhibits excellent dispersibility of cannabinoids even under acidic conditions, and in which oxidative deterioration of cannabinoids does not readily occur.

The present inventors have made intensive studies to achieve the above object, and found that by emulsifying cannabinoids in the presence of a surfactant containing at least an organic acid monoglyceride, dispersibility of cannabinoids under acidic conditions can be improved. The present inventors have found that it can be improved, 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 emulsified composition comprising a cannabinoid and a surfactant,
The emulsified composition, wherein the surfactant contains an organic acid monoglyceride.
Item 2
O / D type emulsion obtained by emulsifying the oil phase in the D phase,
The oil phase contains the cannabinoid,
Item 2. The emulsified composition according to Item 1, wherein the D phase contains an alcohol compound and the surfactant.
Item 3
Item 3. The emulsified composition according to Item 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 polyglycerin fatty acid esters.
Item 4
Item 4. The emulsified composition according to item 3, wherein the sucrose fatty acid ester has an average degree of esterification of 1.0 to 1.3.
Item 5
Item 3. The emulsified composition according to Item 2, wherein the oil phase contains an edible oil.
Item 6
Item 6. The emulsified composition according to any one of Items 1 to 5, wherein the cannabinoid comprises cannabidiol.
Item 7
Item 7. The emulsified composition according to any one of Items 1 to 6, which is used for food, cosmetics, feed, or medicine.

The emulsified composition of the present invention has excellent dispersibility of cannabinoids even under acidic conditions, and the emulsified composition of the present invention is less susceptible 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 emulsified composition of the present invention is an emulsified composition containing a cannabinoid and a surfactant,
The surfactant contains an organic acid monoglyceride.

According to such an emulsified composition, it is possible to improve the dispersibility of cannabinoids even under acidic conditions, and the emulsified composition of the present invention is less susceptible to oxidative deterioration of cannabinoids.

As used herein, "under acidic conditions" means that the pH of the emulsified composition is 7 or less, preferably 4 or less. The pH of the emulsified composition can be measured with a commercially available pH meter.

Each component of the emulsified composition of the present invention will be described.

(cannabinoid)
In the emulsified composition of the present invention, cannabinoids include, for example, one or more of various compound groups contained in cannabinoids derived from cannabis (specifically, cannabidiol (CBD), tetrahydrocannabinol, etc.). can do.

In the emulsified composition of the present invention, the cannabinoid preferably comprises cannabidiol. In this case, the dispersibility of the oil phase in the D phase is likely to be improved, and oxidation deterioration is less likely to occur. Cheap.

In the emulsified composition of the present invention, the cannabinoid preferably contains 50% by mass or more of cannabidiol, more preferably 80% by mass or more, even more preferably 90% by mass or more, and particularly 95% by mass or more. preferable. 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.

(Surfactant)
In the emulsified composition of the present invention, the surfactant contains at least organic acid monoglyceride as described above. Since the surfactant contains an organic acid monoglyceride, the emulsified composition of the present invention has excellent dispersibility even under acidic conditions, and aggregates are less likely to occur.

As used herein, an organic acid monoglyceride means a compound obtained by bonding an organic acid to a hydroxy group of a monoglyceride compound (ester bond). Monoglyceride refers to a compound in which a fatty acid is ester-bonded to one of the three hydroxyl groups of glycerin, and can also be described as "monoglycerin fatty acid ester".

The type of organic acid monoglyceride is not particularly limited, and for example, a wide range of known organic acid monoglycerides can be used. Examples of the organic acid constituting the organic acid monoglyceride include various organic acids such as acetic acid, lactic acid, citric acid, succinic acid, and diacetyltartaric acid. The organic acid constituting the organic acid monoglyceride is preferably citric acid, succinic acid, or diacetyltartaric acid, more preferably diacetyltartaric acid, in that the dispersibility of the emulsified composition under acidic conditions is likely to be improved. .

Also, the type of monoglyceride that constitutes the organic acid monoglyceride is not particularly limited. Fatty acids constituting monoglycerides include various saturated fatty acids and unsaturated fatty acids, and specific examples include caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, and oleic acid. can be done. The fatty acid constituting the monoglyceride is preferably palmitic acid, stearic acid or oleic acid, more preferably stearic acid, in that the dispersibility of the emulsified composition under acidic conditions is easily improved.

In the emulsified composition of the present invention, specific examples of the organic acid monoglyceride include glyceryl lactate monostearate, glyceryl citrate monostearate, glyceryl succinate monostearate, glyceryl diacetyltartrate monostearate, and the like. The organic acid monoglyceride is preferably glyceryl diacetyl tartaric acid monostearate, since the dispersibility of the emulsified composition under acidic conditions is particularly likely to be improved.

In the emulsified composition of the present invention, the organic acid monoglyceride contained in the surfactant can be used singly or in combination of two or more.

The method for producing the organic acid monoglyceride is not particularly limited, and for example, the organic acid monoglyceride can be produced by a known production method. Organic acid monoglycerides can also be obtained from commercial products and the like.

The surfactant contained in the emulsified composition of the present invention may be the organic acid monoglyceride alone, or may contain a surfactant other than the organic acid monoglyceride. From the viewpoint of making it more difficult for cannabinoids to deteriorate due to oxidation, the surfactant contained in the emulsified composition of the present invention preferably contains a surfactant other than the organic acid monoglyceride. Hereinafter, the surfactant other than the organic acid monoglyceride is referred to as "surfactant S".

Surfactants S can include, for example, a wide range of known emulsifiers used for forming emulsions. In the present invention, the surfactant S can have a molecular weight of 200 or more.

Surfactants S can include, for example, sucrose fatty acid esters. 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 only, as used herein, "sucrose fatty acid ester" means a compound formed by an esterification reaction between sucrose and a fatty acid.

The sucrose fatty acid ester preferably has an average degree of esterification of 1.0 to 1.3. In this case, the dispersibility of cannabinoids is likely to be improved, and oxidative deterioration of cannabinoids is particularly difficult to occur, so the emulsified composition of the present invention is easily applied to the fields of foods, cosmetics, feeds, or pharmaceuticals. .

In the emulsified composition of the present invention, the sucrose fatty acid ester preferably has an average degree of esterification of 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.

For the average degree of esterification of sucrose fatty acid ester, the average degree of esterification X of 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 emulsified 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. can.

In the emulsified composition of the present invention, the type of fatty acid moiety (RCOO-site) of the sucrose fatty acid ester 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 emulsified composition of the present invention, the number of carbon atoms in the fatty acid moiety of the sucrose fatty acid ester is not particularly limited. is preferably 25 or less, 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.

Surfactant S is a synthetic surfactant such as sucrose fatty acid ester, sorbitan fatty acid ester, polyglycerin fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyglycerin condensed ricinoleic acid ester, propylene glycol fatty acid ester; , glycolipids, enzyme-treated egg yolks, saponins, plant sterols, non-synthetic surfactants such as milk fat globule membranes, and the like.

The polyglycerin fatty acid ester is a polyglycerin obtained by dehydration condensation of glycerin and ester-bonded with a fatty acid. Specific examples of polyglycerin fatty acid esters include pentaglyceryl monolaurate, hexaglyceryl monolaurate, decaglyceryl monolaurate, pentaglyceryl monomyristate, hexaglyceryl monomyristate, decaglyceryl monomyristate, pentaglyceryl monostearate, mono Hexaglyceryl stearate, decaglyceryl monostearate and the like include pentaglyceryl monolaurate, pentaglyceryl monomyristate and decaglyceryl monomyristate.

The surfactant S contained in the surfactant may be of one type alone, or may be of two or more types.

Surfactant S preferably contains at least one selected from the group consisting of sucrose fatty acid ester, sorbitan fatty acid ester and polyglycerin fatty acid ester (that is, in the emulsified composition of the present invention, the surfactant is an organic It preferably contains an acid monoglyceride and at least one selected from the group consisting of sucrose fatty acid esters, sorbitan fatty acid esters and polyglycerol fatty acid esters). In this case, in the emulsified composition of the present invention, the cannabinoids are easily dispersed, and the oxidative deterioration of the cannabinoids is less likely to occur. easy to apply to

Among them, the surfactant contained in the emulsified composition of the present invention particularly preferably contains an organic acid monoglyceride and a sucrose fatty acid ester. The surfactant may consist of organic acid monoglyceride and at least one selected from the group consisting of sucrose fatty acid ester, sorbitan fatty acid ester and polyglycerin fatty acid ester, or organic acid monoglyceride and sucrose fatty acid. It may consist only of an ester.

(Edible oils and fats)
The emulsified composition of the present invention may also contain edible fats and oils. In this case, the dispersibility of cannabinoids is likely to be improved, and oxidative deterioration is less likely to occur, so the emulsified composition of the present invention is particularly easy to apply in the fields of food, cosmetics, feed, or medicine.

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.

(Emulsified composition)
In the composition of the present invention, the contents of cannabinoid and organic acid monoglyceride are not particularly limited. For example, from the viewpoint of easily improving the dispersion stability of cannabinoids and easily exhibiting the efficacy of cannabinoids, the content of organic acid monoglyceride is 0.01 when the total mass of cannabinoids in the composition is 100 parts by mass. It is preferably at least 0.05 part by mass, more preferably at least 0.1 part by mass, particularly preferably at least 0.2 part by mass, and It is preferably 20 parts by mass or less, more preferably 10 parts by mass or less, even more preferably 5 parts by mass or less, and particularly preferably 3 parts by mass or less.

The emulsion composition of the present invention can 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.

In addition, when the composition of the present invention is in a form other than the O/D emulsion described later, the contents of the solvent, the cannabinoid and the surfactant are not particularly limited. For example, the cannabinoid content relative to 100 parts by mass of the solvent is preferably 5 to 85 parts by mass, more preferably 10 to 80 parts by mass, even more preferably 15 to 75 parts by mass, and 20 to 70 parts by mass. Parts by mass are particularly preferred. Further, the content of the surfactant with respect to 100 parts by mass of the solvent is preferably 1.5 to 16 parts by mass, more preferably 2 to 15 parts by mass, and 2.5 to 14 parts by mass. More preferably, it is particularly preferably 3 to 13 parts by mass.

The emulsified composition of the present invention is preferably an O/D emulsion in which an oil phase is emulsified into a D phase. That is, one embodiment of the emulsified composition of the present invention is an O/D type emulsified composition. More specifically, the emulsified composition of the present invention is an O/D emulsion obtained by emulsifying an oil phase with a D phase, the oil phase contains the cannabinoid, and the D phase contains an alcohol compound and It includes an O/D emulsion composition containing the surfactant. According to such an O/D emulsion composition, the dispersibility of the cannabinoid is particularly excellent, and the cannabinoid exhibits excellent dispersibility even under acidic conditions, and deterioration of the acid value is less likely to occur.

The O / D type emulsion is obtained by an emulsification method (referred to as a D phase emulsification method) using a surfactant phase, the so-called D phase (detergent phase), and the O phase (i.e. , oil phase) are dispersed as, for example, 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.

(O/D type emulsion)
The O/D emulsion, which is a preferred form of the emulsified composition of the present invention, will be described in detail below. The emulsified composition of the present invention can be an O/D emulsion obtained by emulsifying the oil phase into the D phase, as described above.

<Oil phase>
In the O/D emulsion, the oil phase contains at least the cannabinoid (preferably cannabidiol). The oil phase preferably contains the 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, so the emulsion composition of the present invention is particularly useful in the fields of food, cosmetics, feed, or medicine Easy to apply. The edible oil is preferably at least one selected from the group consisting of MCT oil, cottonseed oil and castor oil.

The content of cannabinoids and edible fats and oils in the oil phase is not particularly limited. For example, the content of edible oil is preferably 20 parts by mass or more, more preferably 30 parts by mass or more, and even more preferably 40 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 the surfactant, and particularly a phase that functions as a medium for dispersing the oil phase.

Phase D contains the surfactant, that is, the organic acid monoglyceride. As a result, the O/D type emulsion has excellent dispersibility even under acidic conditions, and aggregates are less likely to occur.

In terms of easily improving the dispersibility of the O/D emulsion under acidic conditions, even in the organic acid monoglyceride contained in the D phase, the organic acid constituting the organic acid monoglyceride is citric acid, succinic acid, It is preferably diacetyltartaric acid, more preferably diacetyltartaric acid, and the fatty acid constituting the monoglyceride is preferably palmitic acid, stearic acid or oleic acid, more preferably stearic acid.

Also in phase D, specific examples of organic acid monoglycerides include glyceryl lactate monostearate, glyceryl citrate monostearate, glyceryl succinate monostearate, glyceryl diacetyl tartrate monostearate, and the like. The organic acid monoglyceride is preferably glyceryl diacetyl tartaric acid monostearate, since the dispersibility of the O/D emulsion is particularly likely to be improved.

The organic acid monoglyceride contained in the surfactant can be used singly or in combination of two or more.

The surfactant contained in the D phase can be the organic acid monoglyceride alone, or the surfactant S can also be included. From the viewpoint that the oxidative deterioration of cannabinoids is less likely to occur, the surfactant contained in the D phase preferably contains the organic acid monoglyceride and the organic acid surfactant S.

Also in the D phase, the surfactant S is preferably at least one selected from the group consisting of sucrose fatty acid esters, sorbitan fatty acid esters and polyglycerol fatty acid esters. That is, the surfactant contained in Phase D preferably contains an organic acid monoglyceride and at least one selected from the group consisting of sucrose fatty acid esters, sorbitan fatty acid esters and polyglycerol fatty acid esters. Surfactant S more preferably contains a sucrose fatty acid ester (that is, the surfactant contained in phase D more preferably contains an organic acid monoglyceride and a sucrose fatty acid ester). In this case, the O/D emulsion has particularly excellent dispersibility even under acidic conditions, and is particularly resistant to oxidative degradation. The surfactant contained in the O/D emulsion may consist of organic acid monoglyceride and at least one selected from the group consisting of sucrose fatty acid ester, sorbitan fatty acid ester and polyglycerin fatty acid ester. , organic acid monoglyceride and sucrose fatty acid ester.

When the surfactant contained in the D phase contains sucrose fatty acid ester, the type of sucrose fatty acid ester is the same as described above. Therefore, the sucrose fatty acid ester contained in the D phase preferably has an average degree of esterification of 1.0 to 1.3, and the average degree of esterification of the sucrose fatty acid ester is 1.01 or more. is preferred. 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 addition, the number of carbon atoms in the fatty acid moiety of the sucrose fatty acid ester contained in the D phase is preferably 30 or less, more preferably 25 or less, in terms of easily increasing the dispersibility of cannabinoids. is more preferable, and 18 or less is particularly preferable. 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.

In the O/D emulsion, the content of the organic acid monoglyceride contained in the D phase is not particularly limited. For example, the content of the organic acid monoglyceride contained in the O/D emulsion is 0.01 per 100 parts by mass of the cannabinoid, because the dispersibility of the cannabinoid under acidic conditions is likely to increase and oxidative deterioration is likely to be suppressed. It is preferably at least 0.05 part by mass, more preferably at least 0.1 part by mass, particularly preferably at least 0.2 part by mass, and It is preferably 20 parts by mass or less, more preferably 10 parts by mass or less, even more preferably 5 parts by mass or less, and particularly preferably 3 parts by mass or less.

In the O/D emulsion, the content of the surfactant S contained in the D phase is not particularly limited. For example, the content of the surfactant S contained in the O/D emulsion is 4 parts by mass or more with respect to 100 parts by mass of the cannabinoid, in that the dispersibility of the cannabinoid is likely to be increased and oxidative deterioration is easily suppressed. is preferably 5 parts by mass or more, more preferably 6 parts by mass or more, preferably 50 parts by mass or less, more preferably 40 parts by mass or less, and 30 parts by mass or less. It is more preferably not more than 20 parts by mass, and particularly preferably not more than 20 parts by mass. When the surfactant S is at least one selected from the group consisting of sucrose fatty acid esters, sorbitan fatty acid esters and polyglycerol fatty acid esters, the above upper and lower limits are particularly preferred.

In the O/D emulsion, the total content of surfactants contained in the D phase is not particularly limited. For example, the total content of surfactants contained in the O/D emulsion is 5 parts by mass or more with respect to 100 parts by mass of cannabinoids, because the dispersibility of cannabinoids is likely to increase and oxidative deterioration is easily suppressed. is 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, and 30 parts by mass or less. It is more preferably not more than 20 parts by mass, and particularly preferably not more than 20 parts by mass. When the surfactant S is at least one selected from the group consisting of sucrose fatty acid esters, sorbitan fatty acid esters and polyglycerol fatty acid esters, the above upper and lower limits are particularly preferred.

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 O/D emulsion, 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 to 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 emulsion is preferably 100 parts by mass or more, preferably 120 parts by mass or more, with respect to 100 parts by mass of the cannabinoid, in that the dispersibility is likely to increase. more preferably 140 parts by mass or more, preferably 1000 parts by mass or less, more preferably 800 parts by mass or less, and even more preferably 600 parts by mass or less, 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 20 parts by mass of the surfactant, and even more preferably 2 to 15 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)
The content of cannabinoids in the O/D emulsion is not particularly limited. For example, when the total mass of cannabinoids, edible fats and oils, surfactants and alcohol compounds is M, the content of cannabinoids is preferably 5% by mass or more, preferably 10% by mass or more, relative to the total mass M. 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, when the oil phase contains edible oil, the content is not particularly limited. For example, in the O/D emulsion, the content of edible fats and oils is preferably 5% by mass or more, more preferably 8% by mass or more, and 10% by mass or more, relative to the total mass M. is 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 is not particularly limited. For example, in the O/D emulsion, the surfactant content is preferably 0.5% by mass or more, more preferably 1% by mass or more, relative to the total mass M, and 10% by mass or more. It is preferably not more than 8% by mass, more preferably not more than 8% by mass, and further preferably not more than 6% by mass.

The O/D emulsion can contain other components 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 type emulsion contains the other component, the content ratio 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 emulsion composition of the present invention % or less, more preferably 10 mass % or less, and particularly preferably 1 mass % or less.

In the O/D emulsion, the average particle size of the oil droplets forming the oil phase is not particularly limited. For example, the median diameter (D50) of the oil droplets constituting the oil phase is preferably 2 μm or less, more preferably 1.8 μm or less, under both acidic and non-acidic conditions. It is more preferably 1.5 µm or less, particularly preferably 1 µm or less, and preferably 0.1 µm or more, more preferably 0.2 µm or more, and 0.3 µm or more. is more preferred. 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 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.

The method for producing the O/D emulsion is not particularly limited, and for example, a production method similar to that for known O/D emulsion compositions can be widely adopted. For example, an O/D emulsion can be 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). .

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.

INDUSTRIAL APPLICABILITY The 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 emulsified composition of the present invention can be applied to uses such as foods, cosmetics, feeds, or pharmaceuticals, and the emulsified composition of the present invention is the O/D emulsion. is particularly suitable for these uses.

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

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

In specifying the inventions included in the present disclosure, each configuration (property, structure, function, etc.) described in each embodiment of the present disclosure may be combined in any way. That is, the present disclosure encompasses all subject matter consisting of any combination of each of the combinable features described herein.

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; organic acid monoglyceride>
・ Organic acid monoglyceride 1: “Poem W-60” manufactured by Riken Vitamin
・ Organic acid monoglyceride 2: “Poem K-30” manufactured by Riken Vitamin
・ Organic acid monoglyceride 3: “Poem B-30” manufactured by Riken Vitamin

<Surfactant; Surfactant S>
- 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 emulsion 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 an interface consisting of 0.2 g of organic acid monoglyceride 1 and 2 g of sucrose fatty acid ester A is placed in another container. Phase D was obtained by mixing the activator with 68 g of glycerin at 70°C. This D phase is kept at 70 ° C., the oil phase is added dropwise over 5 minutes, and emulsified with a homogenizer at a rotation speed of 7000 rpm for 3 minutes (D phase emulsification) to obtain an O / D type emulsion. An emulsified composition was obtained.

(Examples 2 to 20)
Emulsified 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 D 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.

(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.

<Median diameter (D50) under acidic conditions; immediately after production>
The composition immediately after production obtained in each example and comparative example was diluted 100 times with an aqueous citric acid solution having a pH of 3.4 to prepare a dispersion having a concentration of 1% by mass. -2300, manufactured by Shimadzu Corporation), 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 be done. 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, it can be seen that the O/D emulsions obtained in Examples showed no change in D50 under non-acidic conditions even under acidic conditions. Therefore, the emulsified compositions obtained in Examples were excellent in cannabinoid dispersibility even under acidic conditions. In addition, it was found from the results of precipitates and separation, and the rate of change in backscattered light that the emulsified compositions obtained in the examples are resistant to oxidative degradation of cannabinoids. Since the D-phase emulsification was not performed in Comparative Examples 1 to 3, the dispersibility of the cannabinoid was poor, and especially under acidic conditions, the generation of aggregates was remarkable. 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 emulsified composition comprising a cannabinoid and a surfactant,
The surfactant contains an organic acid monoglyceride,
The content of organic acid monoglyceride is 0.01 parts by mass or more and 20 parts by mass or less with respect to 100 parts by mass of the total mass of cannabinoids ,
O / D type emulsion obtained by emulsifying the oil phase in the D phase,
The oil phase contains the cannabinoid,
The emulsified composition, wherein the D phase contains an alcohol compound and the surfactant . 2. The emulsion composition according to claim 1, wherein the surfactant comprises at least one selected from the group consisting of sucrose fatty acid esters, sorbitan fatty acid esters and polyglycerol fatty acid esters. The emulsion composition according to claim 2 , wherein the sucrose fatty acid ester has an average degree of esterification of 1.0 to 1.3. 2. The emulsified composition according to claim 1 , wherein the oil phase contains an edible oil. 3. The emulsified composition of claim 1 or 2, wherein said cannabinoid comprises cannabidiol. 6. The emulsified composition according to claim 5 , which is used for food, cosmetics, feed, or medicine.