Polyphenol composition and method for producing the same

Abstract

To provide a polyphenol composition allowing specific polyphenols, being water-poorly-soluble compounds, to be dissolved at high concentration in a water-based solvent and enabling easy preparation of a highly transparent solution, and a method for producing the same.SOLUTION: The polyphenol composition of the present invention includes a water-poorly-soluble compound and a sucrose fatty acid ester, wherein the water-poorly-soluble compound is one polyphenol selected from the group consisting of flavones, flavanones, isoflavones, and flavonols, 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 polyphenol composition and a method for producing the same. [Background technology]

[0002] Polyphenols, such as flavones and isoflavones, are known to be active ingredients found in a wide variety of plants and are essential components in a variety of fields. For example, polyphenols are used in a wide range of fields, including beverages and foods, health foods, functional foods, cosmetics, nutritional supplements, and pharmaceutical preparations, and their effects are diverse.

[0003] Generally, polyphenols are poorly soluble in water, and when added as an aqueous solution, the polyphenol concentration (concentration of active ingredients) is limited. Therefore, in fields requiring the addition of polyphenols in solution, it is important to provide a highly soluble polyphenol solution. In other words, developing a technology for solubilizing various poorly water-soluble polyphenols in water is extremely important in fields such as food. For example, Patent Document 1 proposes a technology for solubilizing polyphenols by forming a complex between a polyphenol compound and a cyclodextrin compound. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Special Publication No. 2007-518750 Summary of the Invention [Problem to be solved by the invention]

[0005] However, even with the technology disclosed in Patent Document 1, there were problems in that it was difficult to easily solubilize polyphenols, which are poorly water-soluble compounds, and it was also difficult to prepare a highly concentrated and highly transparent solution.

[0006] The present invention has been made in view of the above, and aims to provide a polyphenol composition and a method for producing the same that can easily dissolve specific polyphenols, which are poorly water-soluble compounds, in an aqueous solvent and enable the easy preparation of a highly transparent solution. [Means for solving the problem]

[0007] As a result of extensive research to achieve the above-mentioned object, the inventors discovered that the above-mentioned object can be achieved by using specific polyphenols and specific sucrose fatty acid esters, 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 A poorly water-soluble compound; Sucrose fatty acid esters, Including, the poorly water-soluble compound is one polyphenol selected from the group consisting of flavones, flavanones, isoflavones, and flavonols; The polyphenol 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 polyphenol 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 polyphenol 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 polyphenol composition according to any one of Items 1 to 3, which is in powder form. Section 5 Item 5. A liquid composition comprising a solution of the polyphenol composition according to item 4 dissolved in an aqueous solvent. Section 6 1. A method for producing a polyphenol composition, comprising: The method includes a step of mixing a poorly water-soluble compound with a solubilizing agent containing a sucrose fatty acid ester, the poorly water-soluble compound is one polyphenol selected from the group consisting of flavones, flavanones, isoflavones, and flavonols; A method for producing a polyphenol composition, wherein the sucrose fatty acid ester has an average degree of esterification of 1.01 or more and 1.1 or less. Section 7 Item 7. The method for producing a polyphenol composition according to Item 6, wherein the solubilizing agent further contains at least one selected from the group consisting of surfactants and cyclodextrin compounds. Section 8 Item 8. The method for producing a polyphenol composition according to Item 7, wherein the surfactant comprises at least one selected from the group consisting of polyglycerin fatty acid esters and polyoxyalkylene sorbitan fatty acid esters. Section 9 Item 9. The method according to any one of Items 6 to 8, wherein the polyphenol composition obtained in the above step is the polyphenol composition according to any one of Items 1 to 5. [Effects of the Invention]

[0009] The polyphenol composition of the present invention allows specific polyphenols, which are poorly water-soluble compounds, to be easily dissolved in an aqueous solvent, making it possible to easily prepare a highly transparent solution.

[0010] The polyphenol composition obtained by the production method of the present invention allows specific polyphenols, which are poorly soluble compounds, to be easily dissolved in an aqueous solvent, making it possible to easily prepare a highly transparent solution. Therefore, the production method of the polyphenol composition of the present invention is suitable for producing the polyphenol composition of the present invention. 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. Polyphenol composition The polyphenol composition of the present invention comprises a water-insoluble compound and a sucrose fatty acid ester, wherein the water-insoluble compound is one polyphenol selected from the group consisting of flavones, flavanones, isoflavones, and flavonols, and the sucrose fatty acid ester has an average degree of esterification of 1.01 or more and 1.1 or less.

[0013] The polyphenol composition of the present invention allows specific polyphenols, which are poorly water-soluble compounds, to be easily dissolved in an aqueous solvent, thereby enabling the easy preparation of a highly transparent solution. Therefore, by using the polyphenol composition of the present invention, it is possible to obtain a highly concentrated yet highly transparent polyphenol-containing solution in a simple manner, and the polyphenol composition can be widely applied in various fields such as the food and pharmaceutical fields.

[0014] (Poorly water-soluble compound) The polyphenol composition of the present invention contains at least a poorly water-soluble compound as an essential component. As described above, the poorly water-soluble compound is one polyphenol selected from the group consisting of flavones, flavanones, isoflavones, and flavonols.

[0015] Flavones refer to flavones or derivatives thereof. Similarly, flavanones, isoflavones, and flavonols refer to flavanones or derivatives thereof, isoflavones or derivatives thereof, and flavonols or derivatives thereof, respectively.

[0016] Flavones include, in addition to flavone, 5,7-dimethoxyflavone, 5,7,3',4'-tetramethoxyflavone, 5,7,3',4'-tetrahydroxyflavone, 3,5,7,3',4'-pentamethoxyflavone, 5,7,4'-trimethoxyflavone, 5,7,4'-trihydroxyflavone, 3,5,7-trimethoxyflavone, 5,6,7-trihydroxyflavone, 3,5,7,4'-tetramethoxyflavone, etc., and also include flavone glycosides. Among these, 5,7-dimethoxyflavone is preferred as the flavone because of its superior solubility in aqueous solvents.

[0017] Examples of flavanones include flavanone, hesperetin, hesperidin, homoeriodictyol, naringenin, eriodictyol, etc., as well as flavanone glycosides. Among these, hesperetin is preferred as the flavanone because of its superior solubility in aqueous solvents.

[0018] Examples of isoflavones include genistein, daidzin, daidzein, and genistin, as well as isoflavone glycosides. Daidzin and genistin refer to glycosides of daidzein and genistein, respectively. Genistein is a preferred isoflavone because of its superior solubility in aqueous solvents.

[0019] Flavonols include flavonols, quercetin, myricetin, kaempferol, etc., as well as flavonol glycosides such as rutin and tiliroside. Among these, rutin, quercetin, or myricetin is preferred as the flavonol because of its superior solubility in aqueous solvents. While tiliroside is known to be contained in rosehip extract, in the present invention, tiliroside is tiliroside derived from sources other than rosehip extract.

[0020] The poorly water-soluble compounds used in the present invention (i.e., the above-mentioned specific polyphenols) can be prepared by known methods, or can be obtained from commercial products (for example, reagents).

[0021] (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."

[0022] The polyphenol composition containing sucrose fatty acid ester S can easily solubilize poorly water-soluble compounds in aqueous solvents, thereby improving the filterability of the solution. Therefore, the sucrose fatty acid ester S contained in the polyphenol composition is a component that acts as a solubilizer for poorly water-soluble compounds.

[0023] If the average degree of esterification of the sucrose fatty acid ester is less than 1.01 or exceeds 1.1, it becomes difficult to solubilize the poorly water-soluble compound, making it difficult to obtain a highly transparent solution of the poorly water-soluble compound, and clogging is likely to occur when filtration is performed, resulting in reduced filterability.

[0024] 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.

[0025] In the present invention, the average degree of esterification of sucrose fatty acid esters can be calculated using 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)

[0026] 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

[0027] 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.

[0028] 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.

[0029] In the polyphenol 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 average degree of esterification.

[0030] 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.

[0031] 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.

[0032] In the sucrose fatty acid ester S, the number of carbon atoms in the fatty acid moiety is not particularly limited, and for example, in order to facilitate the solubilization of the poorly water-soluble compound, 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 the solubilization of the poorly water-soluble compound, 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, lauric acid, palmitic acid, stearic acid, etc.

[0033] Sucrose fatty acid esters exist in monoester, diester, and triester forms. The sucrose fatty acid ester S contained in the polyphenol composition may be any of these ester forms, or may contain not only one, but also 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.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] The polyphenol composition of the present invention may contain one or more sucrose fatty acid esters S.

[0040] The polyphenol 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.

[0041] (Ingredients other than sucrose fatty acid ester S) The polyphenol composition of the present invention may contain, in addition to the poorly water-soluble compound and sucrose fatty acid ester, a surfactant (excluding sucrose fatty acid ester), a cyclodextrin compound, and the like.

[0042] When the polyphenol composition of the present invention further contains at least one selected from the group consisting of the surfactant and the cyclodextrin compound, the water-insoluble compound is more easily solubilized. Therefore, in addition to the sucrose fatty acid ester S, the surfactant and the cyclodextrin compound are also components that can function as "solubilizers." Furthermore, when the polyphenol composition of the present invention contains the cyclodextrin compound, the polyphenol composition can be easily powdered, and a powder with a good appearance and no stickiness can be easily obtained.

[0043] The surfactant can be a wide range of surfactants other than sucrose fatty acid esters, and among these, polyglycerin fatty acid esters, polyoxyalkylene sorbitan fatty acid esters, etc. When the surfactant contains at least one selected from the group consisting of polyglycerin fatty acid esters and polyoxyalkylene sorbitan fatty acid esters, the poorly water-soluble compound can be particularly easily solubilized.

[0044] The polyglycerol fatty acid ester refers to a polyglycerol obtained by dehydration condensation of glycerol, to which a fatty acid is ester-bonded. 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, and decaglycerol monooleate. Among these, decaglycerol monomyristate, decaglycerol monolaurate, and decaglycerol monocaprylate are preferred as the polyglycerol fatty acid esters.

[0045] The polyoxyethylene sorbitan fatty acid ester refers to a compound in which a fatty acid is ester-bonded to polyoxyethylene sorbitan. The number of carbon atoms in the fatty acid in the polyoxyethylene sorbitan fatty acid ester is not particularly limited, and is, for example, 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.

[0046] 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.

[0047] The cyclodextrin compound may be cyclodextrin or a derivative thereof. 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-forms. Another example of a cyclodextrin derivative is "Cluster Dextrin" (registered trademark) from Glyco Nutrition Foods Co., Ltd.

[0048] (Polyphenol composition) The polyphenol composition of the present invention contains the above-mentioned poorly water-soluble compound and sucrose fatty acid ester S as essential components, and optionally contains at least one selected from the group consisting of the above-mentioned surfactant and the above-mentioned cyclodextrin compound.

[0049] In the polyphenol composition of the present invention, the content ratio of the poorly water-soluble compound to the sucrose fatty acid ester S can be, for example, as follows: When the polyphenol composition contains a surfactant and / or a cyclodextrin compound, the content of the sucrose fatty acid ester S can be 1 part by mass or more and 200 parts by mass or less per part by mass of the poorly water-soluble compound. In this case, the poorly water-soluble compound can be easily solubilized in an aqueous solvent. The content of the sucrose fatty acid ester S per part by mass of the poorly water-soluble compound is preferably 2 parts by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and particularly preferably 20 parts by mass or more, and preferably 100 parts by mass or less, more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, and particularly preferably 60 parts by mass or less.

[0050] On the other hand, when the polyphenol composition does not contain a surfactant or a cyclodextrin compound (particularly when the solubilizing agent consists solely of sucrose fatty acid ester S), the content of the sucrose fatty acid ester S can be 2 parts by mass or more and 500 parts by mass or less per part by mass of the poorly water-soluble compound. In this case, the poorly water-soluble compound can be easily solubilized in an aqueous solvent. The content of the sucrose fatty acid ester S per part by mass of the poorly water-soluble compound is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, even more preferably 30 parts by mass or more, and particularly preferably 50 parts by mass or more, and preferably 400 parts by mass or less, more preferably 300 parts by mass or less, even more preferably 250 parts by mass or less, and particularly preferably 200 parts by mass or less.

[0051] As described above, it is particularly preferable that the polyphenol composition of the present invention contains the poorly water-soluble compound, the sucrose fatty acid ester S, the surfactant, and the cyclodextrin compound, which makes it particularly easy to solubilize the poorly water-soluble compound and significantly improves filterability.

[0052] When the polyphenol composition of the present invention contains the sucrose fatty acid ester S, the surfactant, and the cyclodextrin compound, the content ratios of these 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, the surfactant, and the 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 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, particularly preferably 10% by mass or more, more preferably 45% by mass or less, even more preferably 40% by mass or less, and particularly preferably 30% by mass or less.

[0053] When the polyphenol composition of the present invention contains the sucrose fatty acid ester S, the surfactant, and the cyclodextrin compound, the content of the cyclodextrin compound is preferably 1% by mass or more and 70% by mass or less relative to the total mass M. The content of the cyclodextrin compound is more preferably 10% by mass or more, even more preferably 20% by mass or more, particularly preferably 30% by mass or more, more preferably 60% by mass or less, even more preferably 50% by mass or less, and particularly preferably 45% by mass or less relative to the total mass M.

[0054] When the polyphenol composition of the present invention contains the sucrose fatty acid ester S, the surfactant, and the cyclodextrin compound, the content of the surfactant is preferably 1% by mass or more and 70% by mass or less relative to the total mass M. The content of the surfactant is more preferably 10% by mass or more, even more preferably 20% by mass or more, particularly preferably 30% by mass or more, and more preferably 60% by mass or less, even more preferably 50% by mass or less, particularly preferably 45% by mass or less relative to the total mass M.

[0055] The polyphenol composition of the present invention contains the poorly water-soluble compound 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 the surfactant and / or cyclodextrin compound. The solubilizing agent may consist only of sucrose fatty acid ester S and the surfactant and / or cyclodextrin compound, but more preferably consists only of sucrose fatty acid ester S, the surfactant, and the cyclodextrin compound.

[0056] The polyphenol composition of the present invention may contain other components in addition to the poorly water-soluble compound, sucrose fatty acid ester S, surfactant, and cyclodextrin compound. The other components may be components that promote the solubilization of the poorly water-soluble compound, or may be additives other than solubilizers. Examples of other components include lecithin, Quillaja saponin, and the like, as well as known additives contained in various foods and various additives contained in various pharmaceuticals.

[0057] When the polyphenol composition of the present invention contains the above-mentioned other components, the content of the other components can be adjusted within a range that does not impair the effects of the present invention. Because poorly water-soluble compounds are easily solubilized in aqueous solvents, the total content of the poorly water-soluble compounds, sucrose fatty acid ester S, surfactant, and cyclodextrin compound contained in the polyphenol composition of the present invention 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 non-volatile content. 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.

[0058] The polyphenol composition of the present invention may consist solely of the poorly water-soluble compound, sucrose fatty acid ester S, and the surfactant and / or the 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.

[0059] The polyphenol composition of the present invention can easily solubilize an aqueous solvent and obtain a highly transparent solution. If the transparency of a solution containing a poorly water-soluble compound is impaired, its application to the food and pharmaceutical fields may be limited. However, the polyphenol composition of the present invention can easily obtain a highly transparent solution of a poorly water-soluble compound, and in addition, the solution has excellent filterability, making it suitable for use in the food and pharmaceutical fields.

[0060] Moreover, the poorly water-soluble compound can be made to have a higher concentration than before, which makes it possible to further enhance the efficacy of the poorly water-soluble compound.

[0061] Therefore, the polyphenol composition of the present invention can be used in a variety of applications, including those requiring various polyphenols. Specifically, the polyphenol composition of the present invention can be used for food, cosmetics, feed, pharmaceuticals, etc. As used herein, "food use" broadly encompasses beverages, supplements, health foods, functional foods, cosmetic foods, and animal feed for pets and other animals. Furthermore, as used herein, "feed use" broadly encompasses feeds that can be used in various livestock farming fields, including feeds used in aquaculture. As used herein, "medicinal use" encompasses not only pharmaceuticals for human consumption or administration, but also pharmaceuticals for animal consumption or administration. When the composition of the present invention is used for food, cosmetics, or pharmaceutical purposes, any of these applications includes those intended for cosmetic purposes. For example, the polyphenol composition of the present invention can be particularly suitably used as a food additive, feed additive, pharmaceutical additive, and cosmetic additive.

[0062] The polyphenol composition of the present invention may be in either solid or liquid form, preferably in solid form, and more preferably in powder form. The polyphenol composition of the present invention may also be in the form of tablets or granules. When the polyphenol composition of the present invention is in liquid form, it can be used after being subjected to an appropriate treatment such as powdering. The polyphenol composition can be used for the various applications described above, whether in solid (powder) or liquid form.

[0063] The method for solubilizing the polyphenol composition of the present invention in an aqueous solvent (more specifically, the method for solubilizing the poorly water-soluble compounds contained in the polyphenol composition of the present invention in an aqueous solvent) is not particularly limited. For example, the polyphenol composition of the present invention can be easily solubilized by mixing it with an aqueous solvent by an appropriate method. Examples of aqueous solvents include water, lower alcohols such as ethanol, and isopropyl alcohol. Among these, one selected from the group consisting of water and ethanol is more preferred, and water is particularly preferred.

[0064] When the polyphenol composition of the present invention is solubilized in an aqueous solvent, the amount of the polyphenol composition of the present invention used can be, for example, 0.01 to 0.05 parts by mass per 100 parts by mass of the aqueous solvent.

[0065] A liquid composition can be prepared by solubilizing the polyphenol composition of the present invention in an aqueous solvent. Such a liquid composition contains a solution of the polyphenol composition of the present invention dissolved in an aqueous solvent, and therefore can be expected to have the effects of the poorly water-soluble compound (polyphenol).

[0066] 2. Method for producing polyphenol composition The method for producing the polyphenol composition of the present invention is not particularly limited, and for example, a wide variety of known production methods can be used. In particular, it is preferable to produce the polyphenol composition of the present invention by a production method comprising the following step 1: Step 1: Mixing a poorly water-soluble compound with a solubilizing agent containing a sucrose fatty acid ester.

[0067] In the step 1, the poorly water-soluble compound is one polyphenol selected from the group consisting of flavones, flavanones, isoflavones, and flavonols, and the sucrose fatty acid ester has an average degree of esterification of 1.01 to 1.1. That is, in the step 1, a solubilizing agent containing the sucrose fatty acid ester S is used.

[0068] The poorly water-soluble compound used in step 1 is one polyphenol selected from the group consisting of flavones, flavanones, isoflavones, and flavonols. The poorly water-soluble compound used in step 1 is in a solid form, such as a powder.

[0069] The solubilizer used in step 1 contains at least a sucrose fatty acid ester S. The type of sucrose fatty acid ester S is the same as the sucrose fatty acid ester S contained in the polyphenol composition of the present invention. Therefore, the sucrose fatty acid ester S contained in the polyphenol composition of the present invention is derived from the sucrose fatty acid ester S contained in the solubilizer.

[0070] The solubilizing agent used in step 1 can contain, in addition to the sucrose fatty acid ester S, a surfactant (excluding sucrose fatty acid esters) and / or a cyclodextrin compound, etc. That is, the solubilizing agent can further contain at least one selected from the group consisting of surfactants and cyclodextrin compounds.

[0071] Here, the surfactant contained in the solubilizing agent is the same as the surfactant contained in the polyphenol composition of the present invention described above, and the cyclodextrin compound contained in the solubilizing agent is the same as the cyclodextrin compound contained in the polyphenol composition of the present invention described above. That is, the surfactant and cyclodextrin compound contained in the polyphenol composition of the present invention are derived from the surfactant and cyclodextrin compound contained in the solubilizing agent used in Step 1, respectively.

[0072] Therefore, the surfactant contained in the solubilizing agent is preferably a polyglycerin fatty acid ester, a polyoxyalkylene sorbitan fatty acid ester, etc. Furthermore, the cyclodextrin compound contained in the solubilizing agent may be cyclodextrin or a derivative thereof, such as α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, hydroxypropylated cyclodextrin, or Glyco Nutrition Foods Co., Ltd.'s "Cluster Dextrin" (registered trademark).

[0073] The solubilizing agent used in step 1 preferably contains sucrose fatty acid ester S, the surfactant, and / or the cyclodextrin compound, and more preferably contains sucrose fatty acid ester S, the surfactant, and the cyclodextrin compound. In these cases, solubilization of the poorly water-soluble compound in the resulting polyphenol composition becomes particularly easy. The solubilizing agent may consist only of sucrose fatty acid ester S, and the surfactant and / or the cyclodextrin compound, and more preferably consists only of sucrose fatty acid ester S, the surfactant, and the cyclodextrin compound.

[0074] The content ratios of the sucrose fatty acid ester S, the surfactant, and the 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, the surfactant, and the 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. 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, particularly preferably 10% by mass or more, more preferably 45% by mass or less, even more preferably 40% by mass or less, and particularly preferably 30% by mass or less.

[0075] In the solubilizing agent, the content of the cyclodextrin compound relative to the total mass M is preferably 1% by mass or more and 70% by mass or less. The content of the cyclodextrin compound relative to the total mass M is more preferably 10% by mass or more, even more preferably 20% by mass or more, particularly preferably 30% by mass or more, more preferably 60% by mass or less, even more preferably 50% by mass or less, particularly preferably 45% by mass or less.

[0076] In the solubilizing agent, the content of the surfactant relative to the total mass M is preferably 1% by mass or more and 70% by mass or less. The content of the surfactant relative to the total mass M is more preferably 10% by mass or more, even more preferably 20% by mass or more, particularly preferably 30% by mass or more, and more preferably 60% by mass or less, even more preferably 50% by mass or less, particularly preferably 45% by mass or less.

[0077] When the solubilizing agent does not contain the surfactant and / or the cyclodextrin compound, the solubilizing agent preferably contains 50% by mass or more, more preferably 70% by mass or more, even more preferably 90% by mass or more, and particularly preferably 95% by mass or more of sucrose fatty acid ester S. The solubilizing agent may consist solely of sucrose fatty acid ester S.

[0078] 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.

[0079] In step 1, the poorly water-soluble compound and the solubilizing agent are mixed. The mixing of the two can be carried out, for example, at a temperature in the range of 20 to 80°C. The mixing time is not particularly limited and can be set within an appropriate range depending on the temperature, for example, 10 minutes to 1 hour. When the solubilizing agent contains sucrose fatty acid ester S, the poorly water-soluble compound can be easily solubilized.

[0080] The method for mixing the poorly water-soluble compound with the powdery solubilizing agent or the solubilizing agent solution in step 1 is not particularly limited, and any known mixing means can be widely used. For example, the poorly water-soluble compound and the powdery solubilizing agent or the solubilizing agent solution can be mixed by stirring using a stirrer or the like, or by shaking or the like.

[0081] When mixing the poorly water-soluble compound and the solubilizing agent in step 1, the mixing ratio of the two can be determined depending on the content ratio of each component contained in the target polyphenol composition. For example, the amount of the poorly water-soluble compound used can be adjusted to 0.01 parts by mass or more and 10 parts by mass or less per 100 parts by mass of the solubilizing agent (solid content equivalent). In this case, the poorly water-soluble compound can be easily solubilized in an aqueous solvent. The amount of the poorly water-soluble compound used per 100 parts by mass of the solubilizing agent (solid content equivalent) is preferably 0.05 parts by mass or more, more preferably 0.1 parts by mass or more, even more preferably 0.15 parts by mass or more, particularly preferably 0.2 parts by mass or more, and preferably 5 parts by mass or less, more preferably 3 parts by mass or less, even more preferably 2 parts by mass or less, and particularly preferably 1.5 parts by mass or less.

[0082] The mixture (mixture) obtained by mixing the poorly water-soluble compound and the solubilizing agent in step 1 may be used as the polyphenol 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 20 to 80°C, for example. In particular, since the poorly water-soluble compound is solubilized by the 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.

[0083] The above separation procedure removes the insoluble matter from the mixture, yielding a solution, to which an antifoaming agent may be added if necessary, and the solution may be concentrated if necessary to obtain a solution or concentrate of the polyphenol composition. The concentration treatment may be carried out, for example, under reduced pressure at a temperature of about 20 to 50°C.

[0084] The solution or concentrate obtained as described above can be dried to obtain a powdered polyphenol composition. For example, any known drying method can be used. For example, spray drying can be used.

[0085] In specifying the inventions included in the present disclosure, the components (properties, structures, functions, etc.) described in each embodiment 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]

[0086] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples.

[0087] (raw materials) A polyphenol composition was prepared by selecting appropriate raw materials from the raw materials listed below.

[0088] <Poorly water-soluble compounds> 5,7-Dimethoxyflavone (Flavone, Fujifilm Wako Pure Chemical Industries, Ltd.) Hesperetin (flavanone, manufactured by Tokyo Chemical Industry Co., Ltd.) Genistein (isoflavone, manufactured by Tokyo Chemical Industry Co., Ltd.) Myricetin (flavonol, manufactured by Tokyo Chemical Industry Co., Ltd.) Rutin (flavonol, manufactured by Tokyo Chemical Industry Co., Ltd.) Quercetin (flavonol, manufactured by Tokyo Chemical Industry Co., Ltd.)

[0089] <Sucrose fatty acid ester S> Sucrose fatty acid ester A (esterification degree 1.01): Obtained according to Production Example 1a described below.

[0090] <Other sucrose fatty acid esters> Sucrose fatty acid ester a (esterification degree 1.4): Daiichi Kogyo Seiyaku Co., Ltd. "DK Ester F-110"

[0091] <Surfactant: Polyglycerol fatty acid ester> Polyglycerin fatty acid ester A: Decaglycerin monolaurate "SY Glystar ML-750" manufactured by Sakamoto Pharmaceutical Industry Co., Ltd.

[0092] <Cyclodextrin compounds> γ-Cyclodextrin: "CAVAMAX W8 Food" manufactured by CycloChem

[0093] (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.

[0094] Example 1a A polyphenol composition was prepared using raw materials selected from the formulation conditions shown in Example 1a in Table 1. Specifically, 5.31 mg of 5,7-dimethoxyflavone (a poorly water-soluble compound) was added to an aqueous solubilizer solution to obtain a mixed solution. The aqueous solubilizer solution used was prepared by mixing 49.92 g of water with 0.17 g of the solubilizer obtained in Production Example 1a, consisting of 0.33 g of sucrose fatty acid ester A, 0.33 g of polyglycerin fatty acid ester A, and 0.33 g of γ-cyclodextrin, as shown in Table 1.

[0095] The above mixture was heated at 60°C for 30 minutes, and then concentrated under reduced pressure at 40°C until the solid content reached 15% by mass. The resulting concentrate was spray-dried to obtain a powdered polyphenol composition.

[0096] (Comparative Example 1a) A powdered polyphenol composition consisting of only 5.31 mg of 5,7-dimethoxyflavone was prepared.

[0097] Example 2a A polyphenol composition was prepared by selecting raw materials shown in the formulation conditions of Example 2a in Table 1. Specifically, 15.10 mg of hesperetin (a poorly water-soluble compound) was added to an aqueous solubilizer solution to obtain a mixed solution. The aqueous solubilizer solution used was prepared by mixing 0.33 g of the solubilizer obtained in Production Example 1a, consisting of 0.66 g of sucrose fatty acid ester A, 0.67 g of γ-cyclodextrin, and 48.32 g of water, as shown in Table 1.

[0098] The above mixed solution was heated at 60°C for 30 minutes, and the resulting concentrated solution was spray-dried to obtain a powdered polyphenol composition.

[0099] (Comparative example 2a) A powdered polyphenol composition consisting of 15.10 mg of hesperetin alone was prepared.

[0100] Example 3a A polyphenol composition was prepared by selecting raw materials shown in the formulation conditions of Example 3a in Table 1. Specifically, 6.14 mg of genistein as a poorly water-soluble compound was added to an aqueous solubilizer solution to obtain a mixed solution. The aqueous solubilizer solution used was prepared by mixing 49.18 g of water with 0.20 g of the solubilizer obtained in Production Example 1a, consisting of 0.40 g of sucrose fatty acid ester A, 0.40 g of polyglycerin fatty acid ester A, and 0.40 g of γ-cyclodextrin, as shown in Table 1.

[0101] The above mixture was heated at 60°C for 30 minutes, then concentrated under reduced pressure at 40°C until the solid content reached 15% by mass. The resulting concentrate was spray-dried to obtain a powdered polyphenol composition.

[0102] (Comparative example 3a) A powdered polyphenol composition consisting of only 6.22 mg of genistein was prepared.

[0103] Example 4a A polyphenol composition was prepared by selecting raw materials shown in the formulation conditions of Example 4a in Table 1. Specifically, 5.11 mg of myricetin was added as a poorly water-soluble compound to a solubilizer aqueous solution to obtain a mixed solution. Here, as shown in Table 1, the solubilizer aqueous solution was prepared by mixing 0.17 g of sucrose fatty acid ester A obtained in Production Example 1a, 0.33 g of polyglycerin fatty acid ester A, and 0.33 g of γ-cyclodextrin, with 49.14 g of water.

[0104] The above mixture was heated at 70°C for 30 minutes, then concentrated under reduced pressure at 40°C until the solid content reached 15% by mass. The resulting concentrate was spray-dried to obtain a powdered polyphenol composition.

[0105] (Comparative example 4a) A powdered polyphenol composition consisting of only 5.18 mg of myricetin was prepared.

[0106] Example 4b A polyphenol composition was prepared by selecting raw materials shown in the formulation conditions of Example 4b in Table 1. Specifically, 10.10 mg of rutin (a poorly water-soluble compound) was added to a solubilizer aqueous solution to obtain a mixed solution, which was prepared by mixing 0.17 g of the solubilizer obtained in Production Example 1a (sucrose fatty acid ester A), 0.33 g of polyglycerin fatty acid ester A, and 0.33 g of γ-cyclodextrin) with 49.16 g of water, as shown in Table 1.

[0107] The above mixture was heated at 50°C for 30 minutes, then concentrated under reduced pressure at 40°C until the solid content reached 15% by mass. The resulting concentrate was spray-dried to obtain a powdered polyphenol composition.

[0108] (Comparative example 4b) A powdered polyphenol composition consisting of 10.00 mg of rutin alone was prepared.

[0109] Example 4c A polyphenol composition was prepared by selecting raw materials shown in the formulation conditions of Example 4c in Table 1. Specifically, 10.10 mg of quercetin as a poorly water-soluble compound was added to a solubilizer aqueous solution to obtain a mixed solution, which was prepared by mixing 0.51 g of the solubilizer obtained in Production Example 1a, 1.00 g of polyglycerin fatty acid ester A, and 1.00 g of γ-cyclodextrin, with 47.52 g of water, as shown in Table 1.

[0110] The above mixture was heated at 80°C for 30 minutes, then concentrated under reduced pressure at 40°C until the solid content reached 15% by mass. The resulting concentrate was spray-dried to obtain a powdered polyphenol composition.

[0111] (Comparative Example 4c) A powdered polyphenol composition consisting of 10.00 mg of quercetin alone was prepared.

[0112] Example 5a A polyphenol composition was prepared using raw materials selected from the formulation conditions shown in Example 5a in Table 2. Specifically, 2.50 mg of 5,7-dimethoxyflavone (a poorly water-soluble compound) was added to an aqueous solubilizer solution to obtain a mixed solution. Here, the aqueous solubilizer solution used was prepared by mixing 0.37 g of the solubilizer consisting of sucrose fatty acid ester A obtained in Production Example 1a with 24.63 g of water, as shown in Table 2. The mixed solution was heated at 60°C for 30 minutes and then concentrated under reduced pressure at 40°C to a solids content of 15% by mass. The resulting concentrate was spray-dried to obtain a powdered polyphenol composition.

[0113] (Comparative example 5a) A powdered polyphenol composition was obtained in the same manner as in Example 5a, except that sucrose fatty acid ester A was changed to sucrose fatty acid ester a.

[0114] Example 6a A polyphenol composition was prepared by selecting raw materials shown in the formulation conditions of Example 6a in Table 2. Specifically, 5.00 mg of hesperetin (a poorly water-soluble compound) was added to an aqueous solubilizer solution to obtain a mixed solution. Here, the aqueous solubilizer solution was prepared by mixing 0.75 g of the solubilizer (sucrose fatty acid ester A) obtained in Production Example 1a with 24.24 g of water, as shown in Table 2. The mixed solution was heated at 60°C for 30 minutes and then concentrated under reduced pressure at 40°C to a solids content of 15% by mass. The resulting concentrate was spray-dried to obtain a powdered polyphenol composition.

[0115] (Comparative Example 6a) A powdered polyphenol composition was obtained in the same manner as in Example 6a, except that sucrose fatty acid ester A was changed to sucrose fatty acid ester a.

[0116] Example 7a A polyphenol composition was prepared by selecting the raw materials shown in the formulation conditions of Example 7a in Table 2. Specifically, 3.04 mg of genistein (a poorly water-soluble compound) was added to an aqueous solubilizer solution to obtain a mixed solution. Here, the aqueous solubilizer solution was prepared by mixing 0.45 g of the solubilizer (sucrose fatty acid ester A) obtained in Production Example 1a with 24.59 g of water, as shown in Table 2. The mixed solution was heated at 60°C for 30 minutes and then concentrated under reduced pressure at 40°C to a solids content of 15% by mass. The resulting concentrate was spray-dried to obtain a powdered polyphenol composition.

[0117] (Comparative Example 7a) A powdered polyphenol composition was obtained in the same manner as in Example 7a, except that sucrose fatty acid ester A was changed to sucrose fatty acid ester a.

[0118] Example 8a A polyphenol composition was prepared by selecting the raw materials shown in the formulation conditions of Example 8a in Table 2. Specifically, 2.53 mg of myricetin was added as a poorly water-soluble compound to a solubilizer aqueous solution to obtain a mixed solution. Here, the solubilizer aqueous solution was prepared by mixing 0.37 g of the solubilizer consisting of sucrose fatty acid ester A obtained in Production Example 1a with 24.63 g of water, as shown in Table 2. The mixed solution was heated at 60 ° C for 30 minutes, and then concentrated under reduced pressure at 40 ° C to a solid content of 15% by mass. The concentrated solution thus obtained was spray-dried to obtain a powdered polyphenol composition.

[0119] (Comparative Example 8a) A powdered polyphenol composition was obtained in the same manner as in Example 8a, except that sucrose fatty acid ester A was changed to sucrose fatty acid ester a.

[0120] Example 8b A polyphenol composition was prepared by selecting the raw materials shown in the formulation conditions of Example 8b in Table 2. Specifically, 5.10 mg of rutin (a poorly water-soluble compound) was added to an aqueous solubilizer solution to obtain a mixed solution. Here, the aqueous solubilizer solution used was prepared by mixing 0.37 g of the solubilizer (sucrose fatty acid ester A) obtained in Production Example 1a with 24.63 g of water, as shown in Table 2. The mixed solution was heated at 60°C for 30 minutes, and then concentrated under reduced pressure at 40°C to a solids content of 15% by mass. The resulting concentrate was spray-dried to obtain a powdered polyphenol composition.

[0121] (Comparative Example 8b) A powdered polyphenol composition was obtained in the same manner as in Example 8b, except that sucrose fatty acid ester A was changed to sucrose fatty acid ester a.

[0122] Example 8c A polyphenol composition was prepared by selecting the raw materials shown in the formulation conditions of Example 8c in Table 2. Specifically, 2.55 mg of quercetin (a poorly water-soluble compound) was added to an aqueous solubilizer solution to obtain a mixed solution. Here, the aqueous solubilizer solution used was prepared by mixing 0.37 g of the solubilizer (sucrose fatty acid ester A) obtained in Production Example 1a with 24.62 g of water, as shown in Table 2. The mixed solution was heated at 60°C for 30 minutes, and then concentrated under reduced pressure at 40°C to a solids content of 15% by mass. The resulting concentrate was spray-dried to obtain a powdered polyphenol composition.

[0123] (Comparative Example 8c) A powdered polyphenol composition was obtained in the same manner as in Example 8c, except that sucrose fatty acid ester A was changed to sucrose fatty acid ester a.

[0124] <Solubility> The solubility of the polyphenol composition was evaluated by checking the presence or absence of turbidity in the solution. Specifically, 0.1 g of the powdered polyphenol composition obtained in each Example and Comparative Example was added to 99.9 g of water, irradiated with ultrasound for 5 minutes, and then kept at 25°C for 1 hour. The solubility was visually inspected and evaluated according to the following criteria. A: No turbidity B: Turbidity is observed

[0125] <Transmittance> The transmittance of the polyphenol composition solution was evaluated by measuring the transmittance of the solution at 660 nm. Specifically, 0.1 g of the powdered polyphenol composition obtained in each Example and Comparative Example was added to 99.9 g of water, irradiated with ultrasound for 5 minutes, and then held at 25°C for 1 hour to obtain a sample for measuring the transmittance at 660 nm. The transmittance of this sample at 660 nm was measured using a ratio beam spectrophotometer U-5100 (manufactured by Hitachi High-Tech Corporation).

[0126] Tables 1 and 2 show the blending conditions and evaluation results for producing the polyphenol compositions of each Example and Comparative Example, respectively.

[0127] The results in Tables 1 and 2 show that a polyphenol composition containing at least a poorly water-soluble compound and a specific sucrose fatty acid ester can be easily dissolved in an aqueous solvent, and a highly transparent solution can be obtained.

[0128] [Table 1]

[0129] [Table 2]

Claims

1. A poorly water-soluble compound; Sucrose fatty acid esters, Including, the poorly water-soluble compound is one polyphenol selected from the group consisting of flavones, flavanones, isoflavones, and flavonols; The polyphenol 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 polyphenol composition according to claim 1, further comprising at least one selected from the group consisting of surfactants and cyclodextrin compounds.

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

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

6. 1. A method for producing a polyphenol composition, comprising: The method includes a step of mixing a poorly water-soluble compound with a solubilizing agent containing a sucrose fatty acid ester, the poorly water-soluble compound is one polyphenol selected from the group consisting of flavones, flavanones, isoflavones, and flavonols; The method for producing a polyphenol composition, wherein the sucrose fatty acid ester has an average degree of esterification of 1.01 or more and 1.1 or less.

7. The method for producing a polyphenol composition according to claim 6, wherein the solubilizing agent further contains at least one selected from the group consisting of surfactants and cyclodextrin compounds.

8. The method for producing a polyphenol composition according to claim 7, wherein the surfactant comprises at least one selected from the group consisting of polyglycerin fatty acid esters and polyoxyalkylene sorbitan fatty acid esters.

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