Caryophyllene composition, liquid composition, and method for solubilizing caryophyllene

Abstract

To provide a caryophyllene composition, a liquid composition, and a method for solubilizing caryophyllene, which have excellent solubility in solvents of β-caryophyllene, are less likely to precipitate in a dissolved state, are highly soluble even in low-temperature environments, and are highly resolubilizable even if precipitation does occur.SOLUTION: The caryophyllene composition of the present invention contains β-caryophyllene and a sucrose fatty acid ester. The sucrose fatty acid ester has a fatty acid moiety with 14 carbon atoms. The caryophyllene composition of the present invention has excellent solubility in solvents, is resistant to precipitation in a dissolved state, and exhibits excellent solubility even at low temperatures, and is highly resolubilizable even if precipitation does occur.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a caryophyllene composition, a liquid composition, and a method for solubilizing caryophyllene. [Background technology]

[0002] β-Caryophyllene is a bicyclic sesquiterpene compound known to be an active ingredient found in various plants. Recent research has indicated that β-caryophyllene may be used as an ingestible food additive and in oral or parenteral formulations (e.g., Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Special Publication No. 2008-514649 Summary of the Invention [Problem to be solved by the invention]

[0004] However, β-caryophyllene has poor solubility in water. Even if a homogeneous solution can be obtained by dissolving β-caryophyllene in a solvent using a solubilizing agent or the like, there is a problem in that precipitation, such as the formation of precipitates or separation, tends to occur during storage. This precipitation makes redissolution difficult, making it difficult to apply to various applications, such as food additives. Therefore, prompt improvement is required. In particular, in low-temperature environments, there is a problem in that a solution that was homogeneously dissolved at room temperature (25°C) is prone to precipitation. Therefore, it is important to make it difficult for β-caryophyllene to precipitate in a solvent even in low-temperature environments, and it is also important to develop technology that allows it to be easily redissolved even if it precipitates.

[0005] The present invention has been made in consideration of the above, and aims to provide a caryophyllene composition, a liquid composition, and a method for solubilizing caryophyllene, which have excellent solubility of β-caryophyllene in solvents, are less likely to precipitate when dissolved, and are highly soluble even in low-temperature environments, and are highly re-solubilizable even if precipitation does occur. [Means for solving the problem]

[0006] As a result of extensive research into achieving the above object, the present inventors have discovered that the above object can be achieved by using a specific sucrose fatty acid ester, and have thus completed the present invention.

[0007] That is, the present invention includes, for example, the subject matter described in the following sections. Item 1 Contains β-caryophyllene and sucrose fatty acid esters, A caryophyllene composition, wherein the sucrose fatty acid ester has a fatty acid moiety with 14 carbon atoms. Section 2 Item 1. The caryophyllene composition according to Item 1, further comprising a solvent. Section 3 Item 3. The caryophyllene composition according to Item 2, wherein the solvent is an aqueous solvent. Section 4 Item 1. The caryophyllene composition according to item 1, which is in powder form. Section 5 Item 5. The caryophyllene composition according to any one of Items 1 to 4, which is for use in food, cosmetics, feed, or medicine. Section 6 Item 5. A liquid composition comprising the caryophyllene composition according to item 4 dissolved in a solvent. Section 7 Item 7. The liquid composition according to Item 6, wherein the solvent is an aqueous solvent. Section 8 A method for solubilizing β-caryophyllene in a solvent using a sucrose fatty acid ester, comprising: A method for solubilizing caryophyllene, wherein the sucrose fatty acid ester has a fatty acid moiety with 14 carbon atoms. Section 9 Item 8. The liquid composition according to Item 6 or 7, which is for food, cosmetics, feed, or pharmaceutical use. [Effects of the Invention]

[0008] The caryophyllene composition of the present invention has excellent solubility of β-caryophyllene in solvents, is less likely to precipitate when dissolved, and has excellent solubility even in low-temperature environments, and even if precipitation does occur, has excellent re-solubility. DETAILED DESCRIPTION OF THE INVENTION

[0009]

[0023] In the present specification, the terms "contain" and "comprise" include the concepts of "contain," "comprise," "consist essentially of," and "consist only of."

[0010] In the numerical ranges described in stages in this specification, the upper or lower limit of a certain numerical range can be arbitrarily combined with the upper or lower limit of another numerical range. In the numerical ranges described in this specification, the upper or lower limit of the numerical range may be replaced with a value shown in an example or a value that can be unambiguously derived from an example. In addition, in this specification, numerical values ​​connected with "to" mean a numerical range that includes the numbers before and after "to" as the lower and upper limits.

[0011] 1. Caryophyllene Composition The caryophyllene composition of the present invention contains β-caryophyllene and a sucrose fatty acid ester, wherein the sucrose fatty acid ester has a fatty acid moiety with 14 carbon atoms.

[0012] The caryophyllene composition of the present invention exhibits excellent solubility of β-caryophyllene in solvents (particularly in aqueous solvents), and is less likely to precipitate in a dissolved state (i.e., less likely to produce precipitates). Furthermore, the caryophyllene composition of the present invention exhibits excellent solubility of β-caryophyllene in solvents even in low-temperature environments, meaning that precipitation is less likely to occur even when a solution of the caryophyllene composition of the present invention is stored in a low-temperature environment. Furthermore, even if precipitation occurs due to long-term storage of this solution, the precipitate can be easily redissolved, and the resolubility is excellent.

[0013] In this specification, "low temperature environment" means, for example, an environment of 10°C or below, and in particular, a low temperature environment can also mean an environment of 4°C or below.

[0014] (β-caryophyllene) The caryophyllene composition of the present invention contains β-caryophyllene as an essential component. The type of β-caryophyllene used in the present invention is not particularly limited. For example, β-caryophyllene extracted from various plants can be used in the caryophyllene composition of the present invention. The method for extracting β-caryophyllene from plants is also not particularly limited, and for example, any known extraction method can be widely used. The type of plant used to extract β-caryophyllene is also not particularly limited.

[0015] The β-caryophyllene contained in the caryophyllene composition of the present invention can also be obtained from a commercially available product sold as a reagent, etc. β-caryophyllene may inevitably contain isomers, derivatives, etc.

[0016] (sucrose fatty acid esters) The caryophyllene composition of the present invention contains, as an essential component, a sucrose fatty acid ester having a fatty acid moiety with 14 carbon atoms. The sucrose fatty acid ester is a component that can act as a solubilizing agent for dissolving β-caryophyllene.

[0017] Hereinafter, a sucrose fatty acid ester having a fatty acid moiety with 14 carbon atoms may be referred to as "sucrose fatty acid ester S."

[0018] A sucrose fatty acid ester is a compound having a chemical structure composed of sucrose and a fatty acid, and has a sucrose moiety and a fatty acid moiety in the molecule. Therefore, for example, a sucrose fatty acid ester means a compound formed by an esterification reaction between sucrose and a fatty acid.

[0019] The sucrose fatty acid ester S contains a sucrose fatty acid ester having a fatty acid moiety with 14 carbon atoms (RCOO-moiety, where R has 13 carbon atoms). The fatty acid moiety may be derived from a saturated fatty acid or an unsaturated fatty acid, and is preferably derived from a saturated fatty acid. That is, the sucrose fatty acid ester S is preferably a compound derived from a saturated fatty acid with 14 carbon atoms (i.e., myristic acid).

[0020] The average degree of esterification of the sucrose fatty acid ester S is not particularly limited, and is preferably, for example, 1 to 2. In this case, the caryophyllene composition of the present invention has higher solubility in solvents, is less susceptible to precipitation or separation, has better solubility in low-temperature environments, and is more likely to have improved resolubility. The average degree of esterification of the sucrose fatty acid ester S is more preferably 1.01 or more, more preferably 1.8 or less, even more preferably 1.5 or less, and particularly preferably 1.3 or less.

[0021] 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) / (1000×56.11)} / {1 / (MwSug+(MwFa-18)X)} (1)

[0022] Here, the meanings of the symbols in formula (1) are as follows: X: Average degree of esterification Ns: number of OH groups in one sucrose molecule Nx: Number of moles of OH groups in 1 g of sample (sucrose fatty acid ester) Ny: number of moles of sucrose fatty acid ester in 1 g of sample OHV: hydroxyl value of sucrose fatty acid ester MwSug: molecular weight of sucrose MwFa: average molecular weight of constituent fatty acids

[0023] The average degree of esterification X can be calculated by substituting known values ​​of Ns, Nx, Ny, OHV, MwSug, and MwFa into the above formula (1). Ns, Nx, Ny, OHV, MwSug, and MwFa can be measured by known methods.

[0024] As can be seen from the above method for calculating the average degree of esterification, the sucrose fatty acid ester S in the present invention can be said to be an aggregate of sucrose fatty acid ester molecules having different degrees of esterification.

[0025] In the β-caryophyllene composition of the present invention, when a commercially available product is used as the sucrose fatty acid ester S, the value disclosed by the manufacturer, such as the manufacturer's guaranteed value or catalog value of the sucrose fatty acid ester, can be used as the value of the average degree of esterification.

[0026] Sucrose fatty acid esters exist in monoester, diester, and triester forms. The sucrose fatty acid ester S contained in the caryophyllene composition of the present invention may be any of these ester forms, or may contain not only one, but also two, or all of these ester forms. In other words, the sucrose fatty acid ester S may contain one or more sucrose fatty acid esters selected from the group consisting of monoester, diester, and triester forms.

[0027] The method for producing the sucrose fatty acid ester S is not particularly limited, and for example, a wide variety of known production methods can be used. For example, the sucrose fatty acid ester S can be synthesized by transesterification of sucrose with a fatty acid ester. An example of the fatty acid ester is the methyl ester of myristic acid.

[0028] The sucrose used in the method for producing sucrose fatty acid ester S may be synthesized by a known method, or sucrose may be commercially available. The sucrose may be unreacted sucrose recovered during the production of sucrose fatty acid esters (so-called "recovered sugar"). The sucrose may be in a solid state or in a solution state dissolved in a solvent. The fatty acid ester used in the method for producing sucrose fatty acid ester S may be synthesized by a known method, or fatty acids may be commercially available.

[0029] The method for adjusting the average degree of esterification of the sucrose fatty acid ester S is not particularly limited, and for example, a wide variety of known methods can be employed. For example, by adjusting various synthesis conditions, such as the ratio of sucrose and fatty acid or its ester used in the production of the sucrose fatty acid ester, the type of fatty acid, and the esterification reaction conditions, the average degree of esterification of the resulting sucrose fatty acid ester S can be controlled within a desired range.

[0030] Alternatively, two or more sucrose fatty acid esters having known average degrees of esterification and different average degrees of esterification may be mixed to obtain a sucrose fatty acid ester S having an average degree of esterification controlled within a desired range. In this case, the average degree of esterification can be easily adjusted to a desired range based on the esterification degree of each sucrose fatty acid ester and the mixing mass ratio.

[0031] The caryophyllene composition of the present invention may contain one or more sucrose fatty acid esters S.

[0032] The caryophyllene composition may contain sucrose fatty acid esters other than sucrose fatty acid ester S, as long as the effects of the present invention are not impaired. Of all the sucrose fatty acid esters contained in the caryophyllene composition of the present invention, the content of the sucrose fatty acid ester S is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 99% by mass or more. The sucrose fatty acid esters contained in the caryophyllene composition of the present invention may consist solely of sucrose fatty acid ester S.

[0033] (Caryophyllene Composition) The caryophyllene composition of the present invention contains β-caryophyllene and a sucrose fatty acid ester having a fatty acid moiety with a carbon number of 14. In the caryophyllene composition of the present invention, the content ratio of β-caryophyllene to the sucrose fatty acid ester S can be adjusted within an appropriate range.

[0034] For example, the content of sucrose fatty acid ester S per 100 parts by mass of β-caryophyllene contained in the caryophyllene composition can be 300 parts by mass or more, preferably 350 parts by mass or more, more preferably 400 parts by mass or more, even more preferably 450 parts by mass or more, and particularly preferably 500 parts by mass or more, in order to increase the solubility of β-caryophyllene in low-temperature environments and to facilitate redissolution even if β-caryophyllene precipitates. Furthermore, the content of sucrose fatty acid ester S per 100 parts by mass of β-caryophyllene contained in the caryophyllene composition is preferably 5,000 parts by mass or less, more preferably 3,000 parts by mass or less, even more preferably 2,000 parts by mass or less, and particularly preferably 1,000 parts by mass or less, in order to increase the solubility of β-caryophyllene in low-temperature environments and to facilitate redissolution even if β-caryophyllene precipitates.

[0035] The caryophyllene composition of the present invention may contain components other than β-caryophyllene and sucrose fatty acid ester S, as long as the effects of the present invention are not impaired. Examples of other components include surfactants other than sucrose fatty acid esters, water-soluble polymers, oils and fats, and various additives. Examples of additives include components that can be found in the food, cosmetic, feed, or pharmaceutical fields.

[0036] The surfactant can be, for example, a wide variety of known surfactants, such as sorbitan fatty acid esters, polyglycerin fatty acid esters, etc. The oils and fats can be edible oils and fats, and specific examples thereof include synthetic oils and fats such as medium-chain fatty acid triglycerides, as well as vegetable oils and fats such as cottonseed oil, castor oil, soybean oil, rapeseed oil, corn oil, olive oil, palm oil, safflower oil, rice oil, sunflower oil, and sesame oil; and animal oils and fats such as lard, beef tallow, milk fat, and fish oil.

[0037] The total content of β-caryophyllene and sucrose fatty acid ester S contained in the caryophyllene composition of the present invention is not particularly limited. For example, the total content of β-caryophyllene and sucrose fatty acid ester S relative to the total amount of nonvolatile components contained in the caryophyllene composition of the present invention can be 50% by mass or more, preferably 60% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, and particularly preferably 95% by mass or more. The nonvolatile components contained in the caryophyllene composition of the present invention may consist solely of β-caryophyllene and sucrose fatty acid ester S.

[0038] The nonvolatile components contained in the caryophyllene composition of the present invention refer to components other than volatile components such as the solvent described below, particularly components other than the solvent. Accordingly, in this specification, the nonvolatile components include solid components and liquid substances that do not volatilize at room temperature (e.g., β-caryophyllene).

[0039] The caryophyllene composition of the present invention may be in a liquid or solid form. When the caryophyllene composition of the present invention is in a liquid form, it may further contain a solvent.

[0040] The type of solvent is not limited as long as it can dissolve β-caryophyllene. The solvent is preferably an aqueous solvent because it can easily dissolve β-caryophyllene.

[0041] Examples of aqueous solvents include water, lower alcohols, polyhydric alcohols, and mixtures thereof. Examples of lower alcohols include alcohol compounds having 1 to 3 carbon atoms, such as methanol, ethanol, and isopropanol, with ethanol being preferred. Examples of polyhydric alcohols include glycerin and sorbitol.

[0042] The aqueous solvent contained in the caryophyllene composition of the present invention is preferably water, ethanol, glycerin, sorbitol, or a mixed solvent thereof, and more preferably water, ethanol, or a mixed solvent thereof.

[0043] When the caryophyllene composition of the present invention contains a solvent, for example, the content of β-caryophyllene per 100 parts by mass of solvent can be 0.1 parts by mass or more, more preferably 1 part by mass or more, even more preferably 5 parts by mass or more, and particularly preferably 10 parts by mass or more, and is preferably 1000 parts by mass or less, more preferably 500 parts by mass or less, even more preferably 100 parts by mass or less, and particularly preferably 50 parts by mass or less.

[0044] When the caryophyllene composition of the present invention contains a solvent, the content of the nonvolatile components relative to the total mass of the solvent and nonvolatile components (100 parts by mass) is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, even more preferably 20 parts by mass or more, and preferably 30 parts by mass or more, and is preferably 500 parts by mass or less, more preferably 300 parts by mass or less, even more preferably 100 parts by mass or less, and particularly preferably 80 parts by mass or less.

[0045] When the caryophyllene composition of the present invention contains a solvent, the caryophyllene composition of the present invention is a solution or dispersion, preferably a solution. In particular, the caryophyllene composition of the present invention contains sucrose fatty acid ester S, which makes it highly soluble in solvents, less susceptible to precipitation or separation, and highly transparent. In particular, the composition is less susceptible to precipitation even in low-temperature environments, and therefore has excellent low-temperature solubility and low-temperature stability. Furthermore, even if a precipitate forms in the solution during long-term storage, the precipitate can be easily redissolved. That is, the precipitate is easily redissolved.

[0046] The redissolving method is not particularly limited, and for example, the redissolving can be easily achieved by applying heat. In this case, the temperature is not particularly limited, and is, for example, 20 to 100°C, preferably 30 to 90°C, and more preferably 40 to 80°C.

[0047] When the caryophyllene composition of the present invention contains a solvent, it may be further diluted with an aqueous solvent as appropriate for use in various applications. For example, it may be diluted to a concentration of 10% by mass or less, or even 1% by mass or less. As described above, the caryophyllene composition of the present invention has excellent solubility in solvents, and therefore remains highly soluble and transparent even when diluted. Furthermore, even if precipitates form over time after dilution, they can be easily redissolved by heating or the like.

[0048] When the caryophyllene composition of the present invention is in a solid form, for example, in a powder form, the powder can be easily dissolved in a solvent, particularly in a low-temperature environment, because it contains sucrose fatty acid ester S.

[0049] When the caryophyllene composition of the present invention is in a solid form such as a powder, a liquid composition containing caryophyllene can be formed by dissolving the composition in a solvent, for example, the aqueous solvent described above.

[0050] The method for producing the caryophyllene composition of the present invention is not particularly limited, and for example, any known method can be widely adopted. For example, the caryophyllene composition of the present invention can be prepared by blending a solution containing sucrose fatty acid ester S of β-caryophyllene with β-caryophyllene in a predetermined ratio. β-Caryophyllene can be emulsified in a solvent and then mixed with a solution containing sucrose fatty acid ester S, or liquid β-caryophyllene can be mixed with a solution containing sucrose fatty acid ester S. The solvent used for mixing can be the aqueous solvent described above.

[0051] The temperature at which mixing is carried out is not particularly limited, and is, for example, 20 to 100°C, preferably 30 to 90°C, and more preferably 40 to 80°C. The mixing method is also not particularly limited, and for example, a wide variety of known mixers can be used. The concentration can also be adjusted by adding a solvent such as an aqueous solvent to the composition obtained as described above.

[0052] When the caryophyllene composition of the present invention is in powder form, it can be prepared by mixing liquid β-caryophyllene and sucrose fatty acid ester S in a predetermined ratio, or it can be obtained by drying the liquid caryophyllene composition using an appropriate drying method. The drying method is not particularly limited, and various methods such as heat drying, spray drying, and freeze drying can be used.

[0053] The caryophyllene composition of the present invention can be used in a variety of applications, including a wide range of applications in which compositions containing cannabidiol have traditionally been used. Specifically, the caryophyllene composition of the present invention can be used in food, cosmetics, feed, pharmaceuticals, and the like. The caryophyllene composition of the present invention can be used in the various applications described above, regardless of whether it is in the form of a dispersion or a powder.

[0054] As used herein, "for food use" broadly encompasses beverages, supplements, health foods, functional foods, foods for cosmetic purposes, and animal feed for pets and other animals. Furthermore, as used herein, "for feed use" broadly encompasses feeds that can be used in various livestock farming fields, including feeds used in aquaculture. As used herein, "for pharmaceutical use" encompasses pharmaceuticals intended for administration to humans as well as pharmaceuticals intended for administration to animals. When the caryophyllene composition of the present invention is used for food, cosmetics, or pharmaceutical purposes, any of these uses includes those intended for cosmetic purposes.

[0055] From the above, the caryophyllene composition of the present invention can be particularly suitably used as, for example, a food additive, a feed additive, a pharmaceutical additive, and a cosmetic additive.

[0056] The present invention also encompasses a method for solubilizing β-caryophyllene in a solvent using a sucrose fatty acid ester. In such a method, the sucrose fatty acid ester is a sucrose fatty acid ester S, i.e., has a fatty acid moiety with 14 carbon atoms. The solvent is also the same as described above, and therefore, an aqueous solvent can be preferably used.

[0057] The solubilization method of the present invention can provide the caryophyllene composition of the present invention. Therefore, the method of the present invention allows β-caryophyllene to be easily dissolved in a solvent, and a solution with high solubility can be prepared even in a low-temperature environment. Furthermore, the resulting solution is less likely to produce precipitates, and even if precipitates do form, they can be easily redissolved.

[0058] In specifying the inventions included in the present disclosure, the components (properties, structures, functions, etc.) described in the embodiments of the present disclosure may be combined in any manner. In other words, the present disclosure includes all subject matter consisting of all combinations of the components that can be combined as described in this specification. [Example]

[0059] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples.

[0060] (Production Example 1: Sucrose fatty acid ester A) In a 1 L flask equipped with a stirrer, thermometer, pressure reducing device, and dimethyl sulfoxide (DMSO) reflux device, 34.2 g of sucrose and 400 g of DMSO were mixed and dissolved at 95°C. To this was added 2.4 g of potassium carbonate and 13.3 g of methyl myristate as a fatty acid ester, and the mixture was reacted at 95°C for 3 hours under a reduced pressure of 2 kPa. After distilling off the solvent, the mixture was purified and dried to obtain sucrose myristate A (fatty acid moiety has 14 carbon atoms) with an average degree of esterification of 1.1.

[0061] (Production Example 2: Sucrose fatty acid ester B) Sucrose fatty acid ester B was obtained in the same manner as in Production Example 1, except that the amount of methyl myristate used was 12.2 g. The average degree of esterification of sucrose fatty acid ester B was 1.01.

[0062] (Production Example 3: Sucrose fatty acid ester C) Sucrose fatty acid ester C was obtained in the same manner as in Production Example 1, except that the amount of methyl myristate used was 14.5 g. The average degree of esterification of sucrose fatty acid ester C was 1.2.

[0063] (Production Example 4: Sucrose fatty acid ester a (fatty acid moiety carbon number: 12)) Sucrose fatty acid ester a was obtained in the same manner as in Production Example 1, except that 11.8 g of methyl laurate was used instead of methyl myristate. The average esterification degree of sucrose fatty acid ester a was 1.1.

[0064] Example 1 0.5 parts by mass of sucrose fatty acid ester A obtained in Production Example 1 and 0.4 parts by mass of ethanol were blended and mixed at 70°C to prepare raw material solution 1. This raw material solution 1 was mixed with 0.1 parts by mass of β-caryophyllene (manufactured by Tokyo Chemical Industry Co., Ltd.) at 70°C to obtain a caryophyllene composition.

[0065] Example 2 A caryophyllene composition was obtained in the same manner as in Example 1, except that the amount of sucrose fatty acid ester A obtained in Production Example 1 was changed to 0.7 parts by mass.

[0066] Example 3 A caryophyllene composition was obtained in the same manner as in Example 1, except that the amount of sucrose fatty acid ester A obtained in Production Example 1 was changed to 0.9 parts by mass.

[0067] Example 4 A caryophyllene composition was obtained in the same manner as in Example 1, except that sucrose fatty acid ester B obtained in Production Example 2 was used instead of sucrose fatty acid ester A obtained in Production Example 1.

[0068] Example 5 A caryophyllene composition was obtained in the same manner as in Example 1, except that sucrose fatty acid ester A obtained in Production Example 1 was replaced with sucrose fatty acid ester C obtained in Production Example 3.

[0069] (Comparative Example 1) A caryophyllene composition was obtained in the same manner as in Example 1, except that sucrose fatty acid ester A obtained in Production Example 1 was replaced with sucrose fatty acid ester a obtained in Production Example 4.

[0070] (Evaluation method) Evaluation samples were prepared using the caryophyllene compositions obtained in each Example and Comparative Example, and these evaluation samples were used to evaluate solubility in solvents (presence or absence of precipitation and presence or absence of separation), transparency, low-temperature stability (solubility at low temperatures), and re-solubility.

[0071] [Preparation of evaluation samples] The caryophyllene compositions obtained in each of the Examples and Comparative Examples were diluted with pure water to a concentration of 1% by mass of β-caryophyllene to obtain aqueous solutions. These aqueous solutions were used as evaluation samples.

[0072] [Presence or absence of precipitation (25℃)] 40 mL of the evaluation sample obtained as described above was placed in a 50 mL container, and the container was left to stand at 25°C for 1 hour. After this, the presence or absence of precipitates in the container was visually confirmed and evaluated according to the following criteria. Note that solidified material adhering to the wall of the container was also considered as precipitates. ≪Judgment criteria≫ A: No precipitate was observed and the solubility was good. B: A slight amount of precipitate was visible, and the solubility was poor. C: A large amount of precipitate was visible, and the solubility was extremely poor.

[0073] [Separation (25℃)] 40 mL of the evaluation sample obtained as described above was placed in a 50 mL container, and the container was left to stand for 1 hour in an environment of 25°C, after which the presence or absence of separation in the container was visually confirmed and evaluated according to the following criteria. The presence or absence of separation was confirmed by checking for the occurrence of layer separation and oil droplets in the container. ≪Judgment criteria≫ A: No separation was observed and the solubility was good. B: Separation was clearly visible, precipitate was observed, and solubility was poor.

[0074] [Transparency (25℃)] The total light transmittance of the evaluation sample obtained as described above was measured at 25°C, and the measured value was used to evaluate the sample according to the following criteria. The total light transmittance was measured using a haze meter NDH4000 (manufactured by Nippon Denshoku Industries Co., Ltd.). ≪Judgment criteria≫ A: The total light transmittance was 95% or more, and the transparency was high. B: The total light transmittance was 80% or more and less than 95%, and the transparency was acceptable for practical use. C: The total light transmittance was less than 80%, and the transparency was poor.

[0075] [Presence or absence of precipitation at low temperatures (4°C)] 40 mL of the evaluation sample obtained as described above was placed in a 50 mL container, and the container was left to stand at 4°C for 1 hour. After this, the presence or absence of precipitates in the container was visually confirmed and evaluated according to the following criteria. Note that solidified material adhering to the wall of the container was also considered as precipitates. ≪Judgment criteria≫ A: No precipitate was observed and the solubility was good. B: A slight amount of precipitate was visible, and the solubility was poor. C: A large amount of precipitate was visible, and the solubility was extremely poor.

[0076] [Separation at low temperatures (4°C)] 40 mL of the evaluation sample obtained as described above was placed in a 50 mL container, and the container was left to stand for 1 hour in an environment of 4°C, after which the presence or absence of separation in the container was visually confirmed and evaluated according to the following criteria. The presence or absence of separation was confirmed by checking for the occurrence of layer separation and oil droplets in the container. ≪Judgment criteria≫ A: No separation was observed and the solubility was good. B: Separation was clearly visible, precipitate was observed, and solubility was poor.

[0077] [Transparency at low temperatures (4℃)] The total light transmittance of the evaluation sample obtained as described above was measured at 4°C, and the sample was evaluated based on the measured value according to the following criteria. The total light transmittance was measured using a haze meter NDH4000 (manufactured by Nippon Denshoku Industries Co., Ltd.). ≪Judgment criteria≫ A: The total light transmittance was 95% or more, and the transparency was high. B: The total light transmittance was 80% or more and less than 95%, and the transparency was acceptable for practical use. C: The total light transmittance was less than 80%, and the transparency was poor.

[0078] [Resolubility] 40 mL of the evaluation sample obtained as described above was placed in a 50 mL container, and the container was left standing at 4°C for 24 hours to precipitate the solids in the solution. After the solids were precipitated, the container was again heated at 70°C for 1 hour, and the condition inside the container was visually inspected and evaluated according to the following criteria. ≪Judgment criteria≫ A: Uniformly dissolved, with good re-solubility. B: Undissolved matter (solid content) was visible, and re-solubility was poor.

[0079] Table 1 shows the compounding conditions for the caryophyllene compositions of each Example and Comparative Example, as well as the evaluation results for each composition. Note that blank spaces in Table 1 indicate that the raw material was not used.

[0080] Table 1 shows that the caryophyllene compositions obtained in the examples have excellent solubility in β-caryophyllene solvents (water and ethanol mixed solvents), are less likely to precipitate in the dissolved state, and have excellent solubility even in low-temperature environments. Furthermore, even if precipitation does occur, the caryophyllene compositions can be easily dissolved by heating, and have excellent resolubility.

[0081] [Table 1]

Claims

1. Contains β-caryophyllene and a sucrose fatty acid ester, A caryophyllene composition, wherein the sucrose fatty acid ester has a fatty acid moiety having 14 carbon atoms.

2. 10. The caryophyllene composition of claim 1, further comprising a solvent.

3. 3. The caryophyllene composition of claim 2, wherein the solvent is an aqueous solvent.

4. 10. The caryophyllene composition of claim 1, in powder form.

5. The caryophyllene composition according to any one of claims 1 to 4, which is for use in food, cosmetics, feed, or medicine.

6. A liquid composition comprising the caryophyllene composition according to claim 4 dissolved in a solvent.

7. The liquid composition according to claim 6 , wherein the solvent is an aqueous solvent.

8. A method for solubilizing β-caryophyllene in a solvent using a sucrose fatty acid ester, comprising: A method for solubilizing caryophyllene, wherein the sucrose fatty acid ester has a fatty acid moiety having 14 carbon atoms.

Images