Tiliroside composition and method for producing the same

Abstract

To provide a tiliroside composition that allows easy dissolution in an aqueous solvent even in the presence of tiliroside derived from a rose hip extract within the composition, as well as a liquid composition containing the tiliroside composition and a method for producing the same.SOLUTION: The tiliroside composition of the present invention comprises a rose hip extract and a sucrose fatty acid ester, wherein the rose hip extract contains tiliroside, and the sucrose fatty acid ester has an average degree of esterification of 1.01 or more and 1.1 or less.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a tiliroside composition and a method for producing the same. [Background technology]

[0002] In recent years, rose hips, which contain various active ingredients such as vitamin C, folic acid, vitamin E, and carotenoids, have been used in various fields, including food, beverages, and cosmetics. In particular, tiliroside, a polyphenol contained in rose hips, has attracted attention as a valuable active ingredient.

[0003] In particular, tiliroside is known to have medicinal effects such as promoting fat metabolism and acting as an antidiabetic agent (see, for example, Patent Document 1), and for example, consuming foods containing rosehip-derived tiliroside can have the effect of reducing human body fat. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2007-176858 Summary of the Invention [Problem to be solved by the invention]

[0005] However, in the manufacturing process of foods containing rosehip-derived tiliroside, when the rosehip-derived tiliroside is dissolved in an aqueous solvent, tiliroside sometimes remains undissolved in the solution due to the low solubility of tiliroside in water.

[0006] The present invention has been made in view of the above, and aims to provide a tiliroside composition that can be easily dissolved in an aqueous solvent even when tiliroside is present in the composition, and a method for producing the same. [Means for solving the problem]

[0007] As a result of extensive research to achieve the above-mentioned objective, the inventors discovered that the above-mentioned objective can be achieved by using a rosehip extract containing tiliroside derived from rosehips and a specific sucrose fatty acid ester, and thus completed the present invention.

[0008] That is, the present invention includes, for example, the subject matter described in the following sections. Item 1 Rosehip extract, Sucrose fatty acid esters, Including, The rosehip extract contains tiliroside, A tiliroside composition, wherein the sucrose fatty acid ester has an average degree of esterification of 1.01 or more and 1.1 or less. Section 2 Item 1. The tiliroside composition according to Item 1, further comprising at least one selected from the group consisting of surfactants and cyclodextrin compounds. Section 3 Item 3. The tiliroside composition according to Item 2, wherein the surfactant comprises at least one selected from the group consisting of polyglycerin fatty acid esters and polyoxyalkylene sorbitan fatty acid esters. Section 4 Item 4. The tiliroside composition according to any one of Items 1 to 3, which is in powder form. Section 5 Item 4. The tiliroside composition according to any one of Items 1 to 3, which is in a liquid form. Section 6 Item 7. A liquid composition containing a solution of the tiliroside composition according to Item 4 dissolved in an aqueous solvent. A method for producing a tiliroside composition, comprising: The method includes a step of mixing a rosehip extract containing tiliroside with a solubilizer containing a sucrose fatty acid ester, A method for producing a tiliroside composition, wherein the sucrose fatty acid ester has an average degree of esterification of 1.01 or more and 1.1 or less. Section 8 Item 8. The method for producing a tiliroside composition according to Item 7, wherein the solubilizing agent further contains at least one selected from the group consisting of surfactants and cyclodextrin compounds. Section 9 Item 9. The method for producing a tiliroside composition according to Item 8, wherein the surfactant comprises at least one selected from the group consisting of polyglycerin fatty acid esters and polyoxyalkylene sorbitan fatty acid esters. Section 10 Item 10. The method according to any one of Items 7 to 9, wherein the result of the method is the tiliroside composition according to any one of Items 1 to 5. [Effects of the Invention]

[0009] The tiliroside composition of the present invention can be easily dissolved in an aqueous solvent even when tiliroside is present in the composition.

[0010] The tiliroside composition obtained by the production method of the present invention can be easily dissolved in an aqueous solvent, even if tiliroside is present in the composition. Therefore, the production method of the tiliroside composition of the present invention is suitable as a method for obtaining a tiliroside composition that is easily soluble in an aqueous solvent. DETAILED DESCRIPTION OF THE INVENTION

[0011]

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

[0012] 1. Tiliroside composition The tiliroside composition of the present invention comprises a rosehip extract and a sucrose fatty acid ester, wherein the rosehip extract contains tiliroside and the sucrose fatty acid ester has an average degree of esterification of 1.01 or more and 1.1 or less.

[0013] The tiliroside composition of the present invention can be easily dissolved in an aqueous solvent, even when tiliroside is present in the composition. Furthermore, the transparency of a solution containing the tiliroside composition can be improved. Therefore, the tiliroside composition of the present invention can be widely applied in various fields, including the food and pharmaceutical fields.

[0014] (Rosehip extract) The tiliroside composition of the present invention contains, as an essential ingredient, a rosehip extract containing at least tiliroside. Rosehip extract refers to a composition containing components extracted by, for example, subjecting at least one part selected from the group consisting of rose pseudocarp and seeds to a solvent extraction treatment. Specific examples of rosehip extract include an extract containing components extracted from rosehip seeds with a solvent, a diluted or concentrated solution thereof, or a dried product thereof. In the description herein, rosehip may sometimes be used as a concept encompassing both rose pseudocarp and seeds, and "rosehip seeds" refers to seeds extracted from rose pseudocarp.

[0015] The rosehip extraction method for obtaining the rosehip extract is not particularly limited, and a wide variety of known extraction methods can be used. Among them, it is preferable to use the rosehip extract obtained by the "extraction process step a" detailed in the section "2. Production method of tiliroside composition" below, and it is even more preferable to use the rosehip extract obtained by the extraction process step a and the later purification process step a.

[0016] Rose hip extract contains tiliroside as an essential component. In this specification, such tiliroside is also referred to as "rose hip-derived tiliroside."

[0017] Rosehip extract may contain components other than tiliroside, specifically components (impurities) extracted from rosehips other than tiliroside.

[0018] (sucrose fatty acid esters) The sucrose fatty acid ester contained in the composition of the present invention has an average degree of esterification in the range of 1.01 to 1.1. As a precaution, in this specification, "sucrose fatty acid ester" means a compound formed by an esterification reaction between sucrose and a fatty acid. Hereinafter, a sucrose fatty acid ester having an average degree of esterification of 1.01 to 1.1 will be referred to as "sucrose fatty acid ester S."

[0019] By including sucrose fatty acid ester S in the tiliroside composition, the tiliroside composition can be easily dissolved in an aqueous solvent even when tiliroside is present in the composition. Furthermore, the transparency of a solution containing the tiliroside composition can be improved. Therefore, the sucrose fatty acid ester S contained in the tiliroside composition is a component that acts as a solubilizer for rosehip extract, particularly for tiliroside. Furthermore, by including sucrose fatty acid ester S in the tiliroside composition, it becomes easier to obtain a good powder of the tiliroside composition.

[0020] If the average degree of esterification of the sucrose fatty acid esters is less than 1.01 or exceeds 1.1, it becomes difficult to solubilize the rosehip extract, and it tends to be difficult to obtain a highly transparent rosehip extract solution.

[0021] The average degree of esterification of the sucrose fatty acid ester S is preferably less than 1.1, more preferably 1.09 or less, even more preferably 1.08 or less, and particularly preferably 1.07 or less.

[0022] In the present invention, the average degree of esterification of sucrose fatty acid esters can be calculated from the following formula (1), and the average degree of esterification X of sucrose fatty acid esters can be estimated thereby. (Ns-X)=(Nx) / (Ny) ={(OHV) / (1000×56.11)} / {1 / (MwSug+(MwFa-18)X)} (1)

[0023] Here, the meanings of the symbols in formula (1) are as follows: 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

[0024] X can be calculated by substituting known values ​​of Ns, Nx, Ny, OHV, MwSug, and MwFa into the above formula (1). Note that Ns, Nx, Ny, OHV, MwSug, and MwFa can be measured by known methods.

[0025] 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.

[0026] When a commercially available product is used as the sucrose fatty acid ester S in the tiliroside composition of the present invention, the value disclosed by the manufacturer, such as the manufacturer's guaranteed value or catalog value for the sucrose fatty acid ester, can be used as the average degree of esterification.

[0027] The type of sucrose fatty acid ester S is not particularly limited as long as the average degree of esterification is within the above range, and for example, a wide range of known sucrose fatty acid esters can be applied to the composition of the present invention.

[0028] There is no particular limitation on the type of fatty acid moiety (RCOO-moiety) of the sucrose fatty acid ester S. The fatty acid moiety of the sucrose fatty acid ester S may be a moiety derived from a saturated fatty acid or an unsaturated fatty acid, and is preferably derived from a saturated fatty acid.

[0029] In the sucrose fatty acid ester S, the number of carbon atoms in the fatty acid moiety is not particularly limited. For example, in order to facilitate solubilization of the rose hip extract, the number of carbon atoms in the fatty acid moiety (including the ester carbon) is preferably 30 or less, more preferably 25 or less, even more preferably 20 or less, and particularly preferably 18 or less. In addition, in order to facilitate solubilization of the rose hip extract, the number of carbon atoms in the fatty acid moiety (including the ester carbon) is preferably 8 or more, more preferably 10 or more, even more preferably 12 or more, and particularly preferably 14 or more. The fatty acid moiety in the sucrose fatty acid ester is preferably derived from, for example, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, etc.

[0030] Sucrose fatty acid esters exist in monoester, diester, and triester forms. The sucrose fatty acid ester S contained in the tiliroside composition may be any of these ester forms, or may contain not only one, but two, or all of the 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.

[0031] 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 employed. For example, the sucrose fatty acid ester S can be synthesized by transesterification of sucrose with a fatty acid ester. Examples of the fatty acid ester include methyl esters of fatty acids.

[0032] 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 the form of a solid or a solution dissolved in a solvent. The fatty acid used in the method for producing sucrose fatty acid ester S may be synthesized by a known method, or sucrose may be commercially available.

[0033] 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, the average degree of esterification of the resulting sucrose fatty acid ester can be controlled within a desired range 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 S, the type of fatty acid, and the esterification reaction conditions.

[0034] Alternatively, two or more sucrose fatty acid esters having known average degrees of esterification and different average degrees of esterification can be mixed to obtain the sucrose fatty acid ester S. In this case, the average degree of esterification can be easily adjusted to a desired range based on the degree of esterification of each sucrose fatty acid ester and the mixing mass ratio.

[0035] Sucrose fatty acid ester S can also be obtained as a commercially available product. Examples of such commercially available products include sucrose fatty acid ester "DK Ester (registered trademark)" manufactured by Daiichi Kogyo Seiyaku Co., Ltd.

[0036] The tiliroside composition of the present invention may contain one or more sucrose fatty acid esters S.

[0037] The tiliroside composition of the present invention 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. Examples of other sucrose fatty acid esters include a wide range of known sucrose fatty acid esters.

[0038] (Ingredients other than sucrose fatty acid ester S) The tiliroside composition of the present invention may contain, in addition to the rosehip extract and sucrose fatty acid ester, a surfactant (excluding sucrose fatty acid ester) and / or a cyclodextrin compound.

[0039] When the tiliroside composition of the present invention further contains at least one selected from the group consisting of surfactants and cyclodextrin compounds, the rosehip extract is more easily solubilized. Therefore, in addition to sucrose fatty acid ester S, surfactants and / or cyclodextrin compounds are also components that can function as "solubilizers."

[0040] When the tiliroside composition of the present invention contains a surfactant, the surfactant can improve the solubility of the rosehip extract. Examples of surfactants include a wide range of surfactants other than sucrose fatty acid esters, and among these, polyglycerin fatty acid esters and polyoxyalkylene sorbitan fatty acid esters are preferred. When the surfactant contains at least one component selected from the group consisting of polyglycerin fatty acid esters and polyoxyalkylene sorbitan fatty acid esters, the solubilization of the rosehip extract is particularly facilitated.

[0041] Polyglycerol fatty acid esters refer to polyglycerols formed by dehydration condensation of multiple glycerol molecules, to which fatty acids are ester-bonded. The number of carbon atoms of the fatty acids in the polyglycerol fatty acid esters is not particularly limited, and is preferably 30 or less, more preferably 25 or less, even more preferably 20 or less, and particularly preferably 18 or less, and is preferably 8 or more, more preferably 10 or more, even more preferably 12 or more, and particularly preferably 14 or more. The number-average degree of polymerization of the polyglycerol moiety in the polyglycerol fatty acid esters is not particularly limited, and is preferably 25 or less, more preferably 20 or less, and is preferably 5 or more, more preferably 6 or more, and even more preferably 10 or more. For example, when the number of carbon atoms of the fatty acid is 14 or more and the number-average degree of polymerization of the polyglycerol moiety is 6 or more, the polyglycerol fatty acid ester tends to become a semi-solid (e.g., a waxy solid) or solid at room temperature (e.g., 25°C). Specific examples of polyglycerol fatty acid esters include pentaglycerol monocaprylate, hexaglycerol monocaprylate, decaglycerol monocaprylate, pentaglycerol monolaurate, hexaglycerol monolaurate, decaglycerol monolaurate, pentaglycerol monomyristate, hexaglycerol monomyristate, decaglycerol monomyristate, pentaglycerol monostearate, hexaglycerol monostearate, decaglycerol monostearate, pentaglycerol monooleate, hexaglycerol monooleate, decaglycerol monooleate, etc. Among these, preferred polyglycerol fatty acid esters are decaglycerol monomyristate, decaglycerol monolaurate, and decaglycerol monocaprylate.

[0042] Polyoxyethylene sorbitan fatty acid ester refers to polyoxyethylene sorbitan to which a fatty acid is ester-bonded. The number of carbon atoms of the fatty acid in the polyoxyethylene sorbitan fatty acid ester is not particularly limited, and is preferably 30 or less, more preferably 25 or less, even more preferably 20 or less, particularly preferably 18 or less, and preferably 8 or more, more preferably 10 or more, even more preferably 12 or more, particularly preferably 14 or more. Specific examples of polyoxyethylene sorbitan fatty acid esters include polyoxyethylene sorbitan oleate, polyoxyethylene sorbitan stearate, and polyoxyethylene sorbitan laurate.

[0043] The HLB values ​​of the polyglycerol fatty acid ester and the polyoxyalkylene sorbitan fatty acid ester are preferably, for example, 11 to 19. In this case, the solubilization of the rose hip extract can be further promoted. In this specification, the HLB value means a value calculated by the Griffin method. The HLB values ​​of the polyglycerol fatty acid ester and the polyoxyalkylene sorbitan fatty acid ester are more preferably 12 to 18, and even more preferably 12.5 to 17.

[0044] On the other hand, the tiliroside composition of the present invention may be stored in powder form. From the viewpoint of enhancing the storage stability of the powder, the surfactant is preferably in a solid state such as a powder at room temperature (e.g., 25°C) or in a semi-solid state that is a solid but contains a solvent, and a solid state is more preferable. In other words, from the viewpoint of enhancing the storage stability of the powder of the tiliroside composition of the present invention, the surfactant is preferably not in a liquid state (including a viscous liquid) or a paste state at room temperature (e.g., 25°C). In terms of particularly enhancing the storage stability of the powder of the tiliroside composition of the present invention, it is also preferable that the tiliroside composition of the present invention does not contain a surfactant. Note that storage stability can mean, for example, that the powder is less likely to caking when stored in a high-humidity environment.

[0045] When the tiliroside composition of the present invention contains a cyclodextrin compound, the cyclodextrin compound can improve the solubility of the rosehip extract, facilitate powdering of the tiliroside composition, and facilitate obtaining a good powder with reduced stickiness. Examples of the cyclodextrin compound include cyclodextrin and its derivatives. Examples of cyclodextrin include α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin. Examples of cyclodextrin derivatives include compounds in which some groups of cyclodextrin are substituted with other substituents. Examples of such substituents include hydroxyalkyl groups having 2 to 4 carbon atoms and alkyl groups having 1 to 2 carbon atoms. Specific examples of cyclodextrin derivatives include hydroxypropylated cyclodextrin. In cyclodextrin derivatives, the cyclodextrin moiety may be any of α-, β-, and γ-cyclodextrin. Further, an example of a cyclodextrin derivative is "Cluster Dextrin (registered trademark)" manufactured by Glico Nutrition Foods Co., Ltd.

[0046] (Tiliroside composition) The tiliroside composition of the present invention contains rosehip extract and sucrose fatty acid ester S as essential ingredients, and optionally contains at least one selected from the group consisting of surfactants and cyclodextrin compounds.

[0047] In the tiliroside composition of the present invention, the content ratio of rosehip extract and sucrose fatty acid ester S can be, for example, as follows: That is, the content of sucrose fatty acid ester S can be 0.1 parts by mass or more and 100 parts by mass or less per 100 parts by mass of rosehip extract (solid content). In this case, the rosehip extract can be easily solubilized in an aqueous solvent, and the transparency of a solution containing the tiliroside composition can be improved. The content of sucrose fatty acid ester S per 100 parts by mass of rosehip extract (solid content) is preferably 1 part by mass or more, more preferably 2.5 parts by mass or more, even more preferably 5 parts by mass or more, even more preferably 7.5 parts by mass or more, and particularly preferably 9 parts by mass or more. Furthermore, the content of sucrose fatty acid ester S per 100 parts by mass of rosehip extract (solid content) is preferably 80 parts by mass or less, more preferably 70 parts by mass or less, even more preferably 60 parts by mass or less, and particularly preferably 50 parts by mass or less.

[0048] Furthermore, the surfactant content in the tiliroside composition of the present invention can be, for example, as follows: That is, the surfactant content may be 0 parts by mass or more, or may exceed 0 parts by mass, per 100 parts by mass of rosehip extract (solid content equivalent). Alternatively, the surfactant content may be 100 parts by mass or less. The surfactant content is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, and even more preferably 75 parts by mass or less, per 100 parts by mass of rosehip extract (solid content equivalent). In particular, when the tiliroside composition contains a surfactant, i.e., when the surfactant content is greater than 0 parts by mass, solubilization of the rosehip extract is more likely to occur.

[0049] On the other hand, in order to improve the storage stability of the powder of the tiliroside composition of the present invention, the content of surfactant is preferably 20 parts by mass or less, more preferably 10 parts by mass or less, and even more preferably 5 parts by mass or less, per 100 parts by mass of rosehip extract (solid content equivalent). Furthermore, the content of surfactant is preferably the same mass or less as the sucrose fatty acid ester S, more preferably 1 / 2 the mass or less, and even more preferably 1 / 3 the mass or less. In these cases, as mentioned above, the surfactant is preferably in a solid state such as a powder at room temperature. In order to improve the storage stability of the powder of the tiliroside composition of the present invention, the tiliroside composition of the present invention does not contain a surfactant (i.e., 0 parts by mass).

[0050] Furthermore, the content of the cyclodextrin compound in the tiliroside composition of the present invention can be, for example, as follows: That is, the content of the cyclodextrin compound may be 0 parts by mass or more, or even more than 0 parts by mass, per 100 parts by mass of rosehip extract (solid content equivalent). Alternatively, the content of the cyclodextrin compound may be 100 parts by mass or less. The content of the cyclodextrin compound is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, and even more preferably 75 parts by mass or less, per 100 parts by mass of rosehip extract (solid content equivalent). In particular, when the tiliroside composition contains a cyclodextrin compound, i.e., when the content of the cyclodextrin compound is greater than 0 parts by mass, solubilization of the rosehip extract is more likely to occur.

[0051] As mentioned above, the tiliroside composition of the present invention preferably contains rosehip extract, sucrose fatty acid ester S, a surfactant and / or a cyclodextrin compound. In this case, the inclusion of sucrose fatty acid ester S and a surfactant and / or a cyclodextrin compound in the tiliroside composition can improve the transparency of a solution in which the tiliroside composition is dissolved. In other words, the solubility of the tiliroside composition in aqueous solvents can be improved.

[0052] When the tiliroside composition of the present invention contains sucrose fatty acid ester S, a surfactant, and a cyclodextrin compound, the content ratios of these are not particularly limited. For example, the content ratio of sucrose fatty acid ester S relative to the total mass of sucrose fatty acid ester S, surfactant, and cyclodextrin compound (hereinafter referred to as "total mass M") is preferably 1% by mass or more and 50% by mass or less. The content ratio of sucrose fatty acid ester S relative to the total mass M is more preferably 3% by mass or more, even more preferably 5% by mass or more, and particularly preferably 10% by mass or more. Furthermore, the content ratio of sucrose fatty acid ester S relative to the total mass M is more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 25% by mass or less, and particularly preferably 20% by mass or less.

[0053] When the tiliroside composition of the present invention contains a sucrose fatty acid ester S, a surfactant, and a cyclodextrin compound, the content of the cyclodextrin compound relative to the total mass M is preferably 5% by mass or more and 60% by mass or less. The content of the cyclodextrin compound relative to the total mass M is more preferably 8% by mass or more, even more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more. Furthermore, the content of the cyclodextrin compound relative to the total mass M is more preferably 55% by mass or less, even more preferably 50% by mass or less, and particularly preferably 45% by mass or less.

[0054] On the other hand, in order to improve the storage stability of the powder of the tiliroside composition of the present invention, the content ratio of the cyclodextrin compound relative to the total mass M is preferably 55% by mass or more, more preferably 60% by mass or more, and is preferably 85% by mass or less, more preferably 80% by mass or less.

[0055] When the tiliroside composition of the present invention contains a sucrose fatty acid ester S, a surfactant, and a cyclodextrin compound, the surfactant content relative to the total mass M is preferably 5% by mass or more and 60% by mass or less. The surfactant content relative to the total mass M is more preferably 8% by mass or more, even more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 30% by mass or more. The surfactant content relative to the total mass M is more preferably 55% by mass or less, even more preferably 50% by mass or less, and particularly preferably 45% by mass or less.

[0056] On the other hand, in order to improve the storage stability of the powder of the tiliroside composition of the present invention, the surfactant content relative to the total mass M is preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, and particularly preferably 5% by mass or less.

[0057] The tiliroside composition of the present invention contains a rosehip extract and a solubilizing agent, and may contain other ingredients as needed. Here, the solubilizing agent essentially contains sucrose fatty acid ester S, and optionally contains a surfactant and / or a cyclodextrin compound. The solubilizing agent may consist only of sucrose fatty acid ester S and a surfactant or cyclodextrin compound, or may consist only of sucrose fatty acid ester S, a surfactant, and a cyclodextrin compound.

[0058] The tiliroside composition of the present invention contains rosehip extract and sucrose fatty acid ester S as essential ingredients, and optionally contains a surfactant and / or a cyclodextrin compound, but may also contain other ingredients in addition to these. Examples of other ingredients include known additives contained in various foods and various additives contained in various pharmaceuticals.

[0059] When the tiliroside composition of the present invention contains the above-mentioned other ingredients, the content of these other ingredients can be adjusted within a range that does not impair the effects of the present invention. In this case, regardless of the presence or absence of a surfactant and / or a cyclodextrin compound in the tiliroside composition, the total content of rosehip extract, sucrose fatty acid ester S, surfactant, and cyclodextrin compound can be 50% by mass or more, preferably 60% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, and particularly preferably 95% by mass or more, based on the solid content of the tiliroside composition. In these cases, the surfactant is preferably at least one selected from the group consisting of polyglycerol fatty acid esters and polyoxyalkylene sorbitan fatty acid esters.

[0060] The tiliroside composition of the present invention may consist solely of rosehip extract, sucrose fatty acid ester S, and a surfactant and / or a cyclodextrin compound. In this case, the surfactant is preferably at least one selected from the group consisting of polyglycerin fatty acid esters and polyoxyalkylene sorbitan fatty acid esters.

[0061] The tiliroside composition of the present invention can be easily solubilized in aqueous solvents, and can also improve the transparency of a solution that the tiliroside composition is dissolved in. If the transparency of a solution containing rosehip extract is impaired, its application in the food and pharmaceutical fields may be limited, whereas the tiliroside composition of the present invention makes it easy to obtain a highly transparent rosehip extract solution, making it suitable for use in the food and pharmaceutical fields.

[0062] Therefore, the tiliroside composition of the present invention can be used in a variety of applications, and can be widely used in applications where tiliroside is required. Specifically, the tiliroside composition of the present invention can be used in foods such as health foods, cosmetics, feed, medicines, etc.

[0063] The tiliroside composition of the present invention may be in either solid or liquid form, preferably in solid form, and more preferably in powder form. Alternatively, the tiliroside composition of the present invention may be in the form of tablets or granules. When the tiliroside composition of the present invention is in liquid form, it can be used after being subjected to an appropriate process such as powdering. The tiliroside composition can be used for the various applications described above, whether in solid (specifically, powder) or liquid form. Furthermore, when the tiliroside composition of the present invention is in solid form (specifically, powder), a liquid composition containing a solution of the tiliroside composition dissolved in an aqueous solvent can also be used for the various applications described above.

[0064] The method for making the tiliroside composition of the present invention into a liquid form (more specifically, the method for solubilizing the rosehip extract contained in the tiliroside composition of the present invention in an aqueous solvent) is not particularly limited. For example, a liquid tiliroside composition can be obtained by mixing a mixture containing rosehip extract and sucrose fatty acid ester S with an aqueous solvent using an appropriate method. Examples of aqueous solvents include water, lower alcohols such as ethanol and isopropyl alcohol, and polyols such as glycerol.

[0065] 2. Method for producing tiliroside composition The method for producing the tiliroside composition of the present invention is not particularly limited, and for example, any known production method can be widely used. In particular, it is preferable to produce the tiliroside composition of the present invention by a production method comprising the following step 1: Step 1: Mixing a rosehip extract containing tiliroside with a solubilizing agent containing a sucrose fatty acid ester. In step 1, the sucrose fatty acid ester has an average degree of esterification of 1.01 or more and 1.1 or less. That is, in step 1, a solubilizing agent containing the above-mentioned sucrose fatty acid ester S is used.

[0066] (Rosehip extract used in step 1) The rosehip extract used in step 1 is produced by extracting rosehips with a solvent. Hereinafter, the step of extracting rosehips will be referred to as "extraction step a."

[0067] The rose hips used in the extraction step (a) may be, for example, crushed rose false fruits or cut rose false fruits. The rose hips may be dried or wet (raw) rose hips.

[0068] In the extraction process step a, a solvent (hereinafter referred to as "extraction solvent") is used for the extraction of rose hips. A wide variety of solvents, including polar and non-polar solvents, can be used as the extraction solvent. Examples of extraction solvents include water; alcohols such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, and 2-butanol; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate; ketones such as acetone; nitriles such as acetonitrile; hydrocarbons such as heptane and hexane; aromatic hydrocarbons such as benzene and toluene; and halogenated aliphatic hydrocarbons such as methylene chloride and chloroform.

[0069] Among these, alcohol, ethyl acetate, carbon dioxide, water, and a mixture of two or more thereof are preferably used as the extraction solvent. As the alcohol, lower alcohols such as ethanol, 1-propanol, 2-propanol, 1-butanol, and 2-butanol are more preferably used, and ethanol is even more preferred. Furthermore, the extraction solvent is also preferably a mixture of an alcohol such as ethanol and water. In this case, the mixing ratio is not particularly limited. The extraction solvent can be used alone or in combination of two or more.

[0070] The extraction method used in the extraction step (a) is not particularly limited, and can be performed by, for example, mixing powdered rosehip with the above-mentioned extraction solvent. The ratio of rosehip to extraction solvent is not particularly limited and can be adjusted as desired.

[0071] The temperature in the above extraction process is not particularly limited. For example, when heating and refluxing are performed in the extraction process step a, the extraction temperature can be set arbitrarily depending on the boiling point of the extraction solvent, etc. The extraction process time is also not particularly limited, and the mixing time of the rose hips and the extraction solvent can be adjusted within an appropriate range depending on the ratio of rose hips to the extraction solvent, the temperature of the extraction process, etc. When mixing the rose hips and the extraction solvent, stirring with a stirrer or shaking can be performed as necessary.

[0072] In the extraction process step a, rosehips are mixed with an extraction solvent to obtain a mixture in which the rosehip extract is extracted into the extraction solvent. This mixture is then subjected to a separation procedure such as filtration or centrifugation to remove insoluble matter, thereby obtaining an extract in which the rosehip extract is dissolved. The extract thus obtained can be used as the rosehip extract. Alternatively, the rosehip extract thus obtained can be further subjected to a purification process. This purification process is referred to as "purification process step a."

[0073] In the purification step a, the rosehip extract obtained in the extraction step a is further purified. For example, the purification method may involve concentrating the rosehip extract obtained in the extraction step a by an appropriate method and filtering the resulting concentrate. If necessary, the concentrate may be diluted with an extraction solvent before filtering. In this case, the extraction solvent may be the same as or different from the solvent used in the extraction step a. It is preferable that the extraction solvent used in the purification step a is the same as the solvent used in the extraction step a, as this tends to improve the yield of the rosehip extract.

[0074] The concentrate or a mixture obtained by adding an extraction solvent to the concentrate as described above (hereinafter referred to as "concentrate, etc.") can be subjected to separation procedures such as filtration and centrifugation as necessary, thereby further removing insoluble matter and obtaining a more highly purified rosehip extract solution (the solvent is the extraction solvent). The temperature of the concentrate, etc., during the separation procedure is not particularly limited and may be, for example, 30°C or higher, 40°C or higher, 50°C or higher, or 90°C or lower, or 80°C or lower.

[0075] As described above, the rosehip extract used in step 1 can be obtained by extraction process step a, but a rosehip extract solution with higher purity can be obtained by performing purification process step a after extraction process step a. The obtained rosehip extract contains tiliroside derived from rosehips.

[0076] The rosehip extract obtained in the extraction process step a, or in the extraction process step a and purification process step a, is used in step 1. The rosehip extract obtained in the extraction process step a, or in the extraction process step a and purification process step a, is obtained in the form of a solution (rosehip extract liquid). In step 1, the rosehip extract may be used in the form of a solution, or, if necessary, the solution may be dried to form a solid (specifically, a powder) and used in step 1. Alternatively, the rosehip extract solution may be concentrated to form a concentrate or paste, and then used in step 1. In terms of reducing the number of steps, it is preferable to use the rosehip extract in the form of a solution (rosehip extract liquid) in step 1, and therefore, the following describes the case where the rosehip extract used is a solution.

[0077] (Solubilizer used in step 1) The solubilizing agent used in step 1 contains at least sucrose fatty acid ester S. Use of sucrose fatty acid ester S in step 1 can increase the yield of tiliroside in the tiliroside composition that is the result of the production method of the present invention. The sucrose fatty acid ester S used as the solubilizing agent in step 1 is the same as the sucrose fatty acid ester S described above for the tiliroside composition. Therefore, in the description of step 1, the description of the tiliroside composition can be referred to as necessary for configurations involving sucrose fatty acid ester S. The sucrose fatty acid ester S contained in the tiliroside composition of the present invention is derived from the sucrose fatty acid ester S contained in the solubilizing agent.

[0078] The solubilizing agent used in step 1 can contain a surfactant (excluding sucrose fatty acid esters) and / or a cyclodextrin compound in addition to the sucrose fatty acid ester S. That is, the solubilizing agent can further contain at least one selected from the group consisting of surfactants and cyclodextrin compounds.

[0079] Here, the surfactants that can be used as solubilizers in Step 1 are the same as those described for the tiliroside composition, and the cyclodextrin compounds that can be used in Step 1 are the same as those described for the tiliroside composition. Therefore, in the description of Step 1, reference can be made to the description of the tiliroside composition, if necessary, for configurations involving surfactants or cyclodextrin compounds.

[0080] When a surfactant is used as a solubilizing agent in step 1, the surfactant preferably includes at least one selected from the group consisting of polyglycerin fatty acid esters and polyoxyalkylene sorbitan fatty acid esters.

[0081] Furthermore, when a cyclodextrin compound is used as a solubilizing agent in Step 1, examples of the cyclodextrin compound include cyclodextrin and derivatives thereof, such as α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, hydroxypropylated cyclodextrin, and Glyco Nutrition Foods Co., Ltd.'s "Cluster Dextrin (registered trademark)."

[0082] The solubilizer used in step 1 contains sucrose fatty acid ester S as an essential component, and optionally also contains a surfactant and / or a cyclodextrin compound. The use of a solubilizer in step 1 makes it particularly easy to solubilize the rose hip extract in the resulting tiliroside composition, and also improves the transparency of the solution in which the tiliroside composition is dissolved. It also further increases the yield of tiliroside in the tiliroside composition that is the result of the production method of the present invention. The solubilizer may consist solely of sucrose fatty acid ester S and a surfactant or cyclodextrin compound, or it may consist solely of sucrose fatty acid ester S, a surfactant, and a cyclodextrin compound.

[0083] The content ratios of the sucrose fatty acid ester S, surfactant, and cyclodextrin compound in the solubilizer used in step 1 are not particularly limited. For example, the content ratio of the sucrose fatty acid ester S relative to the total mass of the sucrose fatty acid ester S, surfactant, and cyclodextrin compound in the solubilizer (i.e., the same as the aforementioned "total mass M") is preferably 1% by mass or more and 50% by mass or less. In the solubilizer, the content ratio of the sucrose fatty acid ester S relative to the total mass M is more preferably 3% by mass or more, even more preferably 5% by mass or more, and particularly preferably 10% by mass or more, and more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 25% by mass or less, and particularly preferably 20% by mass or less.

[0084] In the solubilizer, the content of the cyclodextrin compound relative to the total mass M is preferably 5% by mass or more and 60% by mass or less. The content of the cyclodextrin compound relative to the total mass M is more preferably 8% by mass or more, even more preferably 10% by mass or more, even more preferably 15% by mass or more, particularly preferably 20% by mass or more, and more preferably 55% by mass or less, even more preferably 50% by mass or less, particularly preferably 45% by mass or less.

[0085] On the other hand, in order to improve the storage stability of the powder of the tiliroside composition of the present invention, the content ratio of the cyclodextrin compound relative to the total mass M is preferably 55% by mass or more, more preferably 60% by mass or more, and is preferably 85% by mass or less, more preferably 80% by mass or less.

[0086] In the solubilizer, the surfactant content relative to the total mass M is preferably 5% by mass or more and 60% by mass or less. The surfactant content relative to the total mass M is more preferably 8% by mass or more, even more preferably 10% by mass or more, even more preferably 15% by mass or more, particularly preferably 30% by mass or more, and more preferably 55% by mass or less, even more preferably 50% by mass or less, and particularly preferably 45% by mass or less. As mentioned above, in order to improve the storage stability of the powder of the tiliroside composition of the present invention, the surfactant content relative to the total mass M is preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, and particularly preferably 5% by mass or less. It is also preferable that the solubilizer does not contain a surfactant.

[0087] The solubilizer used in step 1 may be in powder form or in solution form. For example, the solubilizer may be an aqueous solution or a solution using a mixed solvent of water and alcohol as the solvent. The mixed solvent is, for example, a mixture of water and ethanol. When the solubilizer used in step 1 is in solution, the concentration of the solubilizer is not particularly limited and can be, for example, 1 to 10% by mass. Various types of water can be used, such as distilled water, ion-exchanged water, deionized water, pure water, and electrolyzed water.

[0088] (Process 1) In step 1, rosehip extract and a solubilizer are mixed. More specifically, a solution of rosehip extract is mixed with a powdered solubilizer or a solution of the solubilizer. The mixing of the two can be carried out, for example, at a temperature range of 25 to 50°C. The mixing time is not particularly limited as long as the solubilizer is sufficiently dissolved in step 1, and can be set within an appropriate range depending on the temperature. When the solubilizer contains sucrose fatty acid ester S, the rosehip extract is easily solubilized.

[0089] The solid content concentration of the rosehip extract solution used in step 1 is not particularly limited, and is, for example, preferably 0.1 to 20% by mass, more preferably 0.5 to 10% by mass, and more preferably 1 to 5% by mass.

[0090] There are no particular limitations on the method for mixing the rosehip extract solution with the powdered solubilizer or solubilizer solution in step 1, and any known mixing method can be used. For example, the rosehip extract solution and the powdered solubilizer or solubilizer solution can be mixed by stirring using a stirrer or by shaking.

[0091] When mixing the rosehip extract and solubilizer in step 1, the mixing ratio of the two can be determined depending on the content ratio of each component contained in the desired tiliroside composition. For example, the amount of solubilizer added can be 50 parts by mass or more, calculated as solids (i.e., excluding solvent), per 100 parts by mass of rosehip extract (solids content). There are no particular limitations on the upper limit of the amount of solubilizer added, but it can be, for example, 400 parts by mass or less, 200 parts by mass or less, or 100 parts by mass or less. In this case, the rosehip extract can be easily solubilized in the aqueous solvent, and the transparency of the solution containing the tiliroside composition can be improved. The amount of sucrose fatty acid ester S added per 100 parts by mass of rosehip extract (solid content equivalent) is preferably 1 part by mass or more, more preferably 2.5 parts by mass or more, even more preferably 5 parts by mass or more, even more preferably 7.5 parts by mass or more, particularly preferably 9 parts by mass or more, and is preferably 80 parts by mass or less, more preferably 70 parts by mass or less, even more preferably 60 parts by mass or less, and particularly preferably 50 parts by mass or less.

[0092] The mixture (mixture) obtained by mixing the rosehip extract and solubilizing agent in step 1 may be used as the tiliroside composition of the present invention, or the obtained mixture may be further purified. For example, the mixture obtained in step 1 may be subjected to a separation procedure such as filtration or centrifugation. Filtration may be performed at a temperature ranging from 25 to 50°C, for example. In particular, since the rosehip extract is solubilized with a solubilizing agent containing sucrose fatty acid ester S in step 1, clogging during filtration of the mixture is suppressed, allowing for rapid filtration and significantly improved work efficiency.

[0093] The above separation procedure removes the insoluble matter from the mixture, yielding a solution to which an antifoaming agent can be added as needed, and the solution can be concentrated as needed to obtain a solution or concentrate of the tiliroside composition. The concentration treatment can be carried out, for example, under reduced pressure at a temperature of about 20 to 50°C.

[0094] The solution or concentrate obtained as described above can be dried to obtain a powdered tiliroside composition. A wide variety of known drying techniques can be used for the drying. Examples of drying techniques include spray drying, freeze drying, and vacuum drying.

[0095] 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]

[0096] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples.

[0097] (raw materials) Appropriate raw materials were selected from the raw materials shown below to prepare a tiliroside composition.

[0098] <Sucrose fatty acid ester S> Sucrose fatty acid ester A (esterification degree 1.01): Obtained according to Production Example 1a described below. Sucrose fatty acid ester B (esterification degree 1.03): Obtained according to Production Example 1b described below. Sucrose fatty acid ester C (esterification degree 1.05): Obtained according to Production Example 1c described below.

[0099] <Other sucrose fatty acid esters> Sucrose fatty acid ester a (esterification degree 1.2): Daiichi Kogyo Seiyaku Co., Ltd. "DK Ester (registered trademark) F-160"

[0100] <Surfactant: Polyglycerol fatty acid ester> Polyglycerin fatty acid ester A: Decaglycerin monolaurate "SY Glystar (registered trademark) ML-750" manufactured by Sakamoto Pharmaceutical Co., Ltd. (HLB 14.7, viscous liquid) Polyglycerin fatty acid ester B: Decaglycerin monocaprylate "SY Glystar (registered trademark) MCA-750" manufactured by Sakamoto Pharmaceutical Co., Ltd. (HLB 16.1, viscous liquid) Polyglycerin fatty acid ester C: Decaglycerin monomyristate "SY Glystar (registered trademark) MM-750" (HLB 15.7, semi-solid) manufactured by Sakamoto Pharmaceutical Co., Ltd.

[0101] <Surfactant: Polyoxyalkylene sorbitan fatty acid ester> Polyoxyalkylene sorbitan fatty acid ester A: CRODA's "Crillet 4" (polyoxyethylene sorbitan monooleate, viscous liquid) Polyoxyalkylene sorbitan fatty acid ester B: CRODA's "Crillet 3" (polyoxyethylene sorbitan monostearate, paste) Polyoxyalkylene sorbitan fatty acid ester C: "Crillet 1" manufactured by CRODA (polyoxyethylene sorbitan monolaurate, viscous liquid)

[0102] <Other surfactants> Diacetyl tartaric acid monoglyceride ester Sorbitol

[0103] <Cyclodextrin compounds> γ-Cyclodextrin: "CAVAMAX (registered trademark) W8 Food" manufactured by CycloChem Cluster Dextrin (registered trademark) manufactured by Glico Nutrition Foods Co., Ltd.

[0104] (Production Example 1a: Sucrose fatty acid ester A) In a 1 L flask equipped with a stirrer, thermometer, pressure reducer, and dimethyl sulfoxide (DMSO) reflux device, 400 g of DMSO and 34.2 g of sucrose were mixed and dissolved at 95°C. 2.4 g of potassium carbonate and 15.0 g of methyl stearate (as a fatty acid ester) were added, and the mixture was allowed to react for 3 hours at 95°C under a reduced pressure of 2 kPa. Subsequently, lactic acid was added for neutralization, and the DMSO was removed by distillation 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 saline, and the solvent was removed by distillation under reduced pressure to obtain sucrose fatty acid ester A. The average degree of esterification of sucrose fatty acid ester A was 1.01.

[0105] (Production Example 1b: Sucrose fatty acid ester B) Sucrose fatty acid ester B was obtained in the same manner as in Production Example 1a, except that the amount of methyl stearate used was changed to 15.3 g. The average esterification degree of sucrose fatty acid ester B was 1.03.

[0106] (Production Example 1c: Sucrose fatty acid ester C) Sucrose fatty acid ester C was obtained in the same manner as in Production Example 1a, except that the amount of methyl stearate used was changed to 15.6 g. The average degree of esterification of sucrose fatty acid ester C was 1.05.

[0107] (Production Example 2: Rosehip extract) Unground rosehip seeds were mixed with an extraction solvent consisting of ethanol and water, and the mixture was heated under reflux to perform an extraction process. The extract obtained by this extraction process was filtered through a filter cloth to obtain a filtrate (extraction process step a). The filtrate obtained was concentrated under reduced pressure to obtain a concentrate. The concentrate was then filtered through diatomaceous earth (Radiolite (registered trademark) #500, manufactured by Showa Chemical Industry Co., Ltd.), and an appropriate amount of water was added to obtain a liquid rosehip extract (purification process step a).

[0108] Example 1 A tiliroside composition was prepared using raw materials selected from the blending conditions shown in Example 1 in Table 1. Specifically, a powdered solubilizer was added to 0.75 parts by mass (solid content equivalent) of the rosehip extract obtained in Production Example 2 to obtain a mixed solution. Here, the solubilizer was prepared by mixing 0.28 parts by mass of sucrose fatty acid ester A obtained in Production Example 1a and 0.42 parts by mass of γ-cyclodextrin, as shown in Table 1.

[0109] The above mixed solution was heated to 40°C, and after visually confirming that no solubilizer remained undissolved, it was filtered through diatomaceous earth (Radiolite (registered trademark) #500 manufactured by Showa Chemical Industry Co., Ltd.) to obtain filtrate A. The obtained filtrate A was concentrated under reduced pressure, and the resulting concentrate was spray-dried to obtain a powdered tiliroside composition.

[0110] Example 2 As shown in Table 1, a powdered tiliroside composition was obtained in the same manner as in Example 1, except that 0.35 parts by mass of sucrose fatty acid ester A was used and 0.35 parts by mass of polyglycerin fatty acid ester A was used instead of γ-cyclodextrin.

[0111] Example 3 As shown in Table 1, sucrose fatty acid ester A, polyglycerin fatty acid ester A, and gamma-cyclodextrin were used as solubilizers, and a powdered tiliroside composition was obtained in the same manner as in Example 1, except that 0.07 parts by mass of sucrose fatty acid ester A, 0.35 parts by mass of polyglycerin fatty acid ester A, and 0.28 parts by mass of gamma-cyclodextrin were used.

[0112] Examples 4 to 8 As shown in Table 1, a powdered tiliroside composition was obtained in the same manner as in Example 3, except that the amount of solubilizer added was changed.

[0113] Example 9 As shown in Table 1, sucrose fatty acid ester A, polyglycerin fatty acid ester A, γ-cyclodextrin, and cluster dextrin (registered trademark) were used as solubilizers, and a powdered tiliroside composition was obtained in the same manner as in Example 1, except that the amounts of sucrose fatty acid ester A, polyglycerin fatty acid ester A, γ-cyclodextrin, and cluster dextrin (registered trademark) were 0.14 parts by mass, 0.28 parts by mass, 0.14 parts by mass, and 0.14 parts by mass of cluster dextrin (registered trademark).

[0114] Example 10 As shown in Table 2, sucrose fatty acid ester A, polyglycerin fatty acid ester B, and gamma-cyclodextrin were used as solubilizers, and a powdered tiliroside composition was obtained in the same manner as in Example 1, except that 0.14 parts by mass of sucrose fatty acid ester A, 0.28 parts by mass of polyglycerin fatty acid ester B, and 0.28 parts by mass of gamma-cyclodextrin were used.

[0115] Example 11 As shown in Table 2, a powdered tiliroside composition was obtained in the same manner as in Example 10, except that 0.28 parts by mass of polyglycerin fatty acid ester C was added instead of polyglycerin fatty acid ester B.

[0116] Example 12 As shown in Table 2, a powdered tiliroside composition was obtained in the same manner as in Example 10, except that 0.28 parts by mass of polyoxyalkylene sorbitan fatty acid ester A was added instead of polyglycerin fatty acid ester B.

[0117] Example 13 As shown in Table 2, a powdered tiliroside composition was obtained in the same manner as in Example 10, except that 0.28 parts by mass of polyoxyalkylene sorbitan fatty acid ester B was added instead of polyglycerin fatty acid ester B.

[0118] Example 14 As shown in Table 2, a powdered tiliroside composition was obtained in the same manner as in Example 10, except that 0.28 parts by mass of polyoxyalkylene sorbitan fatty acid ester C was added instead of polyglycerin fatty acid ester B.

[0119] Example 15 As shown in Table 2, a powdered tiliroside composition was obtained in the same manner as in Example 6, except that 0.14 parts by mass of sucrose fatty acid ester B was added instead of sucrose fatty acid ester A.

[0120] Example 16 As shown in Table 2, a powdered tiliroside composition was obtained in the same manner as in Example 6, except that 0.14 parts by mass of sucrose fatty acid ester C was added instead of sucrose fatty acid ester A.

[0121] Example 17 As shown in Table 2, a powdered tiliroside composition was obtained in the same manner as in Example 11, except that the amount of polyglycerin fatty acid ester C was changed to 0.14 parts by mass and the amount of γ-cyclodextrin was changed to 0.42 parts by mass.

[0122] Example 18 As shown in Table 2, a powdered tiliroside composition was obtained in the same manner as in Example 17, except that the amount of sucrose fatty acid ester A was changed to 0.21 parts by mass and the amount of polyglycerin fatty acid ester C was changed to 0.07 parts by mass.

[0123] Example 19 As shown in Table 2, a powdered tiliroside composition was obtained in the same manner as in Example 17, except that the amount of polyglycerin fatty acid ester C was changed to 0.07 parts by mass and the amount of γ-cyclodextrin was changed to 0.49 parts by mass.

[0124] Example 20 As shown in Table 2, a powdered tiliroside composition was obtained in the same manner as in Example 1, except that the amount of sucrose fatty acid ester A was changed to 0.14 parts by mass and the amount of γ-cyclodextrin was changed to 0.56 parts by mass.

[0125] (Comparative Example 1) As shown in Table 3, a powdered tiliroside composition was obtained in the same manner as in Example 1, except that 0.75 parts by mass of rosehip extract and 0.70 parts by mass of γ-cyclodextrin were blended.

[0126] (Comparative Example 2) As shown in Table 3, a powdered tiliroside composition was obtained in the same manner as in Comparative Example 1, except that 0.28 parts by mass of gamma-cyclodextrin, 0.28 parts by mass of polyglycerin fatty acid ester A, and 0.14 parts by mass of diacetyltartaric acid monoglyceride ester (other surfactant) were blended.

[0127] (Comparative Example 3) As shown in Table 3, a powdered tiliroside composition was obtained in the same manner as in Comparative Example 2, except that 0.14 parts by mass of sorbitol (another surfactant) was added instead of diacetyltartaric acid monoglyceride ester.

[0128] Comparative Example 4 As shown in Table 3, a powdered tiliroside composition was obtained in the same manner as in Example 1, except that 0.75 parts by mass of rosehip extract, 0.14 parts by mass of sucrose fatty acid ester a, 0.28 parts by mass of polyglycerin fatty acid ester A, and 0.28 parts by mass of γ-cyclodextrin were combined.

[0129] (Comparative Example 5) As shown in Table 3, a powdered tiliroside composition was obtained in the same manner as in Comparative Example 1, except that 0.70 parts by mass of polyglycerin fatty acid ester A was added instead of γ-cyclodextrin.

[0130] <Transmittance> The transmittance (total light transmittance) of the tiliroside composition solution was evaluated by measuring the transmittance of the solution at a wavelength of 660 nm. Specifically, a sample was prepared by mixing 0.1 g of the powdered tiliroside composition obtained in each Example and Comparative Example with 99.9 g of water. The absence of any precipitate due to undissolved tiliroside composition was confirmed visually during sample preparation. Each of the above samples was then subjected to a ratio beam spectrophotometer U-5100 (manufactured by Hitachi High-Technologies Corporation) to measure the transmittance at a wavelength of 660 nm. It was determined that the higher the transmittance value, the higher the transparency of the solution and the higher the solubility of the tiliroside composition in aqueous solvents.

[0131] <Tiliroside yield> Accurately measure 1 mL of the pre-filtration mixture and filtrate A obtained in Examples 1 to 16 and Comparative Examples 1 to 5. Each was diluted to 10 mL with 50% by volume aqueous methanol, and then sonicated to dissolve, yielding two test solutions. These test solutions were measured using high-performance liquid chromatography under the following conditions to obtain the area values ​​of tiliroside. A calibration curve was also prepared using a tiliroside reference standard (manufactured by EXTRASYNTHESE SA). This calibration curve was also prepared using high-performance liquid chromatography under the following conditions. The tiliroside content before and after filtration was calculated from the area values ​​and the calibration curve for each Example and Comparative Example. The ratio of the tiliroside content after filtration to the tiliroside content before filtration was then calculated, and this ratio was defined as the tiliroside yield. It was determined that the higher the tiliroside yield, the higher the solubility of the tiliroside composition in aqueous solvents. That is, the solubility of the tiliroside composition in an aqueous solvent was determined based on the transmittance value and tiliroside yield value described above, and it was determined that the larger these values ​​were, the better the solubility. High-performance liquid chromatography conditions Column: Inertsil (registered trademark) ODS-3 (particle size 5 μm, inner diameter 4.6 mm, length 250 mm, manufactured by GL Sciences), Column temperature: 40℃ Developing solvent: 0.1% phosphoric acid aqueous solution / acetonitrile = 70 / 30 mixture, ·Flow rate: 1mL / min, Injection volume onto column: 20 μL Detector: UV spectrophotometer (wavelength 315 nm) Under the above conditions, the tiliroside peak was observed at a retention time of approximately 10 to 11 minutes.

[0132] <Appearance evaluation of powder (immediately after preparation)> Immediately after preparation of the tiliroside compositions obtained in each Example and Comparative Example, the appearance of the powder was checked visually and by touch, and the state of the powder was evaluated based on the following criteria. ≪Judgment criteria≫ A: The powder was not sticky and had a good appearance. B: The powder was slightly sticky but had no practical problems. C: The powder was sticky, causing poor handling. D: It did not turn into powder.

[0133] <Evaluation of powder appearance (storage stability)> 1 g of the tiliroside composition powder obtained in each Example and Comparative Example was placed in a PET / AL / PE laminated bag (Lamizip (registered trademark) AL-9, manufactured by Seisan Nippon Co., Ltd.), heat-sealed, and stored in an environment of 40°C and 75% RH for one month. After storage, the appearance of the powder was checked visually and by touch with a spatula, and the state of the powder was evaluated based on the following criteria. ≪Judgment criteria≫ A: No caking was observed and the storage stability was excellent. B: When crushed with a spatula, a slight amount of brittle solidification was observed, but the powder was practically acceptable. C: When crushed with a spatula, hard solidification was observed, causing a decrease in handleability. D: Completely solidified and extremely poor in storage stability.

[0134] Tables 1, 2, and 3 show the compounding conditions and evaluation results for producing the tiliroside compositions of each Example and Comparative Example, respectively. Note that blank spaces in Tables 1, 2, and 3 indicate that the raw material was not used.

[0135] The results in Tables 1, 2, and 3 demonstrate that tiliroside compositions containing at least rosehip extract and a specific sucrose fatty acid ester can be easily dissolved in aqueous solvents, yielding highly transparent solutions. It was also confirmed that the tiliroside compositions obtained in each Example had a high tiliroside yield. Furthermore, the tiliroside compositions obtained in the Examples generally had good powder appearance. Furthermore, a comparison of Examples 1 and 20 with the other Examples revealed that the storage stability of the powder was particularly improved when no surfactant was included. On the other hand, it was also revealed that, even when a surfactant was included, Examples 18 and 19 exhibited better storage stability as powders than Examples 2 to 17.

[0136] [Table 1]

[0137] [Table 2]

[0138] [Table 3]

Claims

1. Rosehip extract, Sucrose fatty acid esters, Including, The rosehip extract contains tiliroside, A tiliroside composition, wherein the sucrose fatty acid ester has an average degree of esterification of 1.01 or more and 1.1 or less.

2. The tiliroside composition according to claim 1, further comprising at least one selected from the group consisting of surfactants and cyclodextrin compounds.

3. The tiliroside composition according to claim 2, wherein the surfactant comprises at least one selected from the group consisting of polyglycerin fatty acid esters and polyoxyalkylene sorbitan fatty acid esters.

4. The tiliroside composition according to any one of claims 1 to 3, which is in powder form.

5. The tiliroside composition according to any one of claims 1 to 3, which is in a liquid form.

6. A liquid composition comprising a solution of the tiliroside composition according to claim 4 dissolved in an aqueous solvent.

7. A method for producing a tiliroside composition, comprising: The method includes a step of mixing a rosehip extract containing tiliroside with a solubilizer containing a sucrose fatty acid ester, The method for producing a tiliroside composition, wherein the sucrose fatty acid ester has an average degree of esterification of 1.01 or more and 1.1 or less.

8. 8. The method for producing a tiliroside composition according to claim 7, wherein the solubilizing agent further contains at least one selected from the group consisting of surfactants and cyclodextrin compounds.

9. 9. The method for producing a tiliroside composition according to claim 8, wherein the surfactant comprises at least one selected from the group consisting of polyglycerin fatty acid esters and polyoxyalkylene sorbitan fatty acid esters.

Images