Oral Compositions

Oral compositions with polyalkoxyflavonoids and chlorogenic acids in specific ratios address solubility issues, improving taste and clarity, thus increasing consumer appeal.

JP7610395B2Active Publication Date: 2025-01-08KAO CORP
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Patent Information

Application Number
JP2020186554
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Filing Date
2020-11-09
Publication Date
2025-01-08
Estimated Expiration
2040-11-09

AI Technical Summary

Technical Problem

Polyalkoxyflavonoids, such as nobiletin and tangeretin, have low water solubility, leading to roughness on the tongue and turbidity in beverages, which decreases consumer desire and necessitates amorphous solid dispersions for solubilization, offering limited improvement.

Method used

Formulating oral compositions with polyalkoxyflavonoids and chlorogenic acids in specific mass ratios to enhance solubility, suppressing roughness and turbidity.

Benefits of technology

The oral compositions improve solubility, reducing roughness on the tongue and turbidity in beverages, enhancing consumer acceptance and ease of use.

✦ Generated by Eureka AI based on patent content.

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Abstract

To provide an oral composition that contains a polyalkoxy flavonoid and achieves reduction in roughness on the tongue during oral ingestion and turbidity in beverage form.SOLUTION: An oral composition contains following components (A) and (B): (A) a polyalkoxy flavonoid represented by formula (1) of 3-50 mass% in solid content and (B) chlorogenic acids, the mass ratio between component (A) and component (B) [(B) / (A)] of 1-30. [In the formula, R1 is a hydrogen atom or a C1-6 alkyl group, R2, R3 and R4 independently represent a hydrogen atom or a C1-6 alkoxy group, R5 and R6 independently represent a C1-6 alkyl group].SELECTED DRAWING: None
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Description

[Technical field]

[0001] The present invention relates to oral compositions. [Background technology]

[0002] Polyalkoxyflavonoids such as nobiletin and tangeretin are found in extracts of citrus plants. They are useful ingredients that are expected to contribute to improving and supporting memory by extending neurites in the brain in response to nerve growth factor (NGF).

[0003] However, since polyalkoxyflavonoids have a solubility in water of less than 0.01 mg / mL, and are particularly low in water among poorly water-soluble polyphenols, it is difficult to effectively use them in foods, beverages, medicines, etc. Therefore, various techniques for solubilizing polyalkoxyflavonoids in water have been studied. For example, a method of dissolving nobiletin or a nobiletin-containing substance in a 20 to 90% by volume aqueous ethanol solution and drying the resulting solution to obtain a solid dispersion in which nobiletin is dispersed in an amorphous state (Patent Document 1), a method of mixing nobiletin or a nobiletin-containing substance with a water-soluble hesperidin derivative, melting the mixture by heating, and then cooling and solidifying the mixture to obtain a solid dispersion in which nobiletin is dispersed in an amorphous state (Patent Document 2), and a method of mixing nobiletin with a polypeptide and a polysaccharide, melting the mixture by heating, and then cooling and solidifying the mixture to obtain a solid dispersion in which nobiletin is dispersed in an amorphous state in the polypeptide and polysaccharide (Patent Document 3) are known. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2019-167336 A [Patent Document 2] JP 2018-131432 A [Patent Document 3] JP 2016-49105 A Summary of the Invention [Problem to be solved by the invention]

[0005] The present inventors have found that, when considering the application of polyalkoxyflavonoids to oral compositions, the low solubility of polyalkoxyflavonoids in water causes roughness on the tongue when polyalkoxyflavonoids are orally taken directly or in the form of instant beverages, which is an obstacle to continuous intake, and that when polyalkoxyflavonoids are taken in the form of packaged beverages, they are prone to become cloudy, which impairs the aesthetic appearance of the beverage, leading to a decline in consumer willingness to purchase them.Furthermore, the above-mentioned prior art requires the use of an amorphous solid dispersion in order to impart water solubility to polyalkoxyflavonoids, and has found that there is room for improvement in terms of more easily solubilizing polyalkoxyflavonoids in water.

[0006] The present invention aims to improve the solubility of polyalkoxyflavonoids in water, and more easily provide an oral composition that suppresses the roughness felt on the tongue when orally taken and the turbidity in beverage form that are caused by polyalkoxyflavonoids. [Means for solving the problem]

[0007] In view of the above-mentioned problems, the present inventors have conducted extensive research and have found that by incorporating a specific polyphenol in a specific mass ratio to a specific amount of polyalkoxyflavonoid, the solubility of the polyalkoxyflavonoid in water is improved, and the roughness on the tongue when taken orally and the cloudiness when made into a beverage can be suppressed.

[0008] That is, the present invention provides the following [1] to [5]. [1] A composition for oral administration comprising the following components (A) and (B), wherein the mass ratio of component (A) to component (B) [(B) / (A)] is 1 to 30: (A) a polyalkoxyflavonoid represented by the following formula (1) in an amount of 3 to 50% by mass based on the solid content, and (B) Chlorogenic acids [2] A solid composition for oral administration comprising the following components (A) and (B), wherein the mass ratio of component (A) to component (B) [(B) / (A)] is 1 to 30: (A) 3 to 50% by mass of a polyalkoxyflavonoid represented by the following formula (1), and (B) Chlorogenic acids [3] A liquid composition for oral administration comprising the following components (A) and (B), wherein the mass ratio of component (A) to component (B) [(B) / (A)] is 1 to 30: (A) 0.03% by mass or more of a polyalkoxyflavonoid represented by the following formula (1), and (B) Chlorogenic acids [4] A method for suppressing roughness on the tongue caused by polyalkoxyflavonoids when orally ingested, comprising: the following components (A) and (B), wherein the components (A) and (B) are coexisting in a mass ratio of 1 to 30 [(B) / (A)]: (A) a polyalkoxyflavonoid represented by the following formula (1), and (B) Chlorogenic acids [5] A method for suppressing cloudiness in a beverage caused by polyalkoxyflavonoids, comprising: (A) a polyalkoxyflavonoid represented by the following formula (1), and (B) Chlorogenic acids

[0009] [ka]

[0010] [In the formula, R 1 is a hydrogen atom or C 1-6 R represents an alkyl group. 2 , R 3 and R 4 are each independently a hydrogen atom or C 1-6 R represents an alkoxy group. 5 and R 6 are mutually independent, C 1-6 represents an alkyl group. Effect of the Invention

[0011] The oral composition of the present invention has improved solubility of polyalkoxyflavonoid in water, thereby reducing the roughness on the tongue when taken orally and the cloudiness when made into a beverage. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] [Oral Composition] In this specification, "oral composition" refers to a composition that is unlikely to be harmful to human health and is taken orally in normal social life, and is not limited to administrative classifications such as food, medicine, quasi-drug, etc. Therefore, the oral composition of the present invention means a wide range of foods and drinks that constitute general foods, health foods (functional foods and drinks), health functional foods (specified health foods, nutrient functional foods, functional foods), quasi-drugs, medicines, etc. that are taken orally.

[0013] The composition for oral administration of the present invention contains, as component (A), a polyalkoxyflavonoid represented by the following formula (1).

[0014] [ka]

[0015] [In the formula, R 1 is a hydrogen atom or C 1-6 R represents an alkyl group. 2 , R 3 and R 4 are each independently a hydrogen atom or C 1-6 R represents an alkoxy group. 5 and R 6 are mutually independent, C 1-6 represents an alkyl group.

[0016] In formula (1), R 1 , R 5 and R 6 C in 1-6The alkyl group may be either linear or branched, so long as it has 1 to 6 carbon atoms. Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Among these, C 1-3 It is an alkyl group, more preferably a methyl group or an ethyl group, and further preferably a methyl group. Also, R 2 , R 3 and R 4 C in 1-6 The alkoxy group may be either linear or branched, so long as it has 1 to 6 carbon atoms. Specific examples include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group. Among these, C 1-3 An alkoxy group is preferable, a methoxy group or an ethoxy group is more preferable, and a methoxy group is even more preferable.

[0017] Among these, from the viewpoint of providing excellent physiological effects, component (A) is preferably one or more selected from nobiletin and tangeretin, and more preferably nobiletin.

[0018] Among the components (A), if nobiletin is contained, it will extend neurites in the brain in response to NGF, and therefore it is expected to contribute to the improvement and support of memory and the like. Therefore, the oral composition of the present invention can be used as an oral composition for improving memory, an oral composition for supporting memory, or an oral composition for extending neurites. These compositions may contain nobiletin as an active ingredient, or may contain chlorogenic acids, which are the component (B) described below, as an active ingredient, or may contain both nobiletin and chlorogenic acids as active ingredients. In addition, with regard to the memory improvement or memory support of the component (B) chlorogenic acids, the contents described in International Publication No. 2007 / 091613 (applicant: University of Tsukuba) and JP-A-2018-39797 (applicant: Kao Corporation) can be used.

[0019] Component (A) may be a commercially available reagent or may be contained in the form of a plant extract containing polyalkoxyflavonoid. The plant is not particularly limited as long as it is one that is commonly used in the field of food and beverages, but for example, nobiletin is contained in Rutaceae plants. Examples of Rutaceae plants include Citrus depressa, Citrus unshiu, Citrus tangerina, Citrus erythrosa, Citrus aurantium, Citrus Natsudaidai, Citrus grandis, Citrus Junos, Citrus rericulata, Citrus limon, Citrus trifoliata, and Citrus medica L., which are all members of the Citrus genus. One or more kinds of plants can be used. Among them, lemon citrus, satsuma mandarin, and bitter orange are preferable. In addition, the plant extract may be a concentrate or a purified product thereof. The method and conditions of extraction, concentration, and purification are not particularly limited, and known methods and conditions can be adopted.

[0020] The content of component (A) in the solid content of the oral composition of the present invention is 3% by mass or more, preferably 4% by mass or more, more preferably 4.5% by mass or more, from the viewpoint of providing an excellent physiological effect, and is 50% by mass or less, preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 20% by mass or less, and even more preferably 8% by mass or less, from the viewpoint of suppressing roughness on the tongue when taken orally, suppressing turbidity when made into a beverage form, and suppressing the bitterness and astringency of the polyalkoxyflavonoid itself. The content of component (A) in the solid content of the oral composition of the present invention is 3 to 50% by mass, preferably 4 to 40% by mass, more preferably 4.5 to 30% by mass, even more preferably 4.5 to 20% by mass, and even more preferably 4.5 to 8% by mass. In this specification, the term "solid content" refers to the residue obtained by drying 1 g of a sample in an electric thermostatic dryer at 105°C for 3 hours and removing volatile substances, and the term "solid content amount" refers to the mass of the residue. In addition, the content of component (A) in this specification is defined based on the total amount of the compound represented by the above formula (1). Furthermore, the content of component (A) can be measured by an analytical method suitable for the condition of the measurement sample among commonly known measurement methods, for example, it can be analyzed by liquid chromatography. Specifically, the method described in the examples below can be mentioned. In addition, when measuring, the sample may be freeze-dried to fit the detection range of the device, or impurities in the sample may be removed to fit the separation ability of the device, and other appropriate treatments may be performed as necessary.

[0021] The oral composition of the present invention contains chlorogenic acids as component (B). Here, in the present specification, "chlorogenic acids" is a collective term for monocaffeoylquinic acids, i.e., 3-caffeoylquinic acid, 4-caffeoylquinic acid, and 5-caffeoylquinic acid, monoferuloylquinic acids, i.e., 3-feruloylquinic acid, 4-feruloylquinic acid, and 5-feruloylquinic acid, and dicaffeoylquinic acids, i.e., 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid. In the present invention, it is sufficient to contain at least one of the above nine types of chlorogenic acids.

[0022] Chlorogenic acids may be in the form of a salt, for example, salts with alkali metals such as sodium and potassium, salts with alkaline earth metals such as magnesium and calcium, salts with organic amines such as monoethanolamine, diethanolamine and triethanolamine, and salts with basic amino acids such as arginine, lysine, histidine and ornithine.

[0023] Component (B) may be contained in the form of a commercially available reagent or an extract of a plant containing chlorogenic acids. The plant is not particularly limited as long as it contains chlorogenic acids and is commonly used in the field of food and beverages, and examples thereof include sunflower seeds, unripe apples, coffee beans, Simon leaves, cones of pinaceae plants, seed shells of pinaceae plants, sugarcane and Nandina leaves, burdock, eggplant skin, plum fruit, coltsfoot, and grape plants. One or more types of plants can be used. Among them, coffee beans are preferred. The coffee beans may be green or roasted, but green coffee beans are preferred in terms of the chlorogenic acid content. The type of coffee tree may be any of Arabica, Robusta, Liberica, and Arabusta. The plant extract may be a concentrate or a purified product thereof. The method and conditions for extraction, concentration, and purification are not particularly limited, and known methods and conditions can be adopted. Furthermore, as the chlorogenic acids, commercially available preparations containing chlorogenic acids may be used, for example, Flavor Holder RC (Hasegawa Fragrance Co., Ltd.).

[0024] The content of component (B) in the solid content of the oral composition of the present invention is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, and even more preferably 80% by mass or more, from the viewpoint of suppressing roughness on the tongue when orally taken and suppressing turbidity when made into a beverage, and is preferably 97% by mass or less, more preferably 96% by mass or less, and even more preferably 95.5% by mass or less, from the viewpoint of suppressing bitterness and astringency of the oral composition. The content of component (B) in the solid content of the oral composition of the present invention is preferably 50 to 97% by mass, more preferably 60 to 96% by mass, even more preferably 70 to 96% by mass, and even more preferably 80 to 95.5% by mass. In this specification, the content of component (B) is defined based on the total amount of the above nine kinds. The content of component (B) can be measured by an analytical method suitable for the condition of the measurement sample among commonly known measurement methods, and can be analyzed by liquid chromatography, for example. Specifically, the method described in the Examples below can be mentioned. During measurement, the sample may be freeze-dried to fit the detection range of the instrument, or contaminants may be removed from the sample to fit the resolution of the instrument, or other appropriate processing may be performed as necessary.

[0025] In the oral composition of the present invention, the mass ratio of component (A) to component (B) [(B) / (A)] is 1 or more, preferably 2 or more, more preferably 4 or more, even more preferably 12 or more, and even more preferably 16 or more, from the viewpoint of suppressing roughness on the tongue when orally taken, and from the viewpoint of suppressing bitterness and astringency of the oral composition, it is 30 or less, preferably 27 or less, more preferably 24 or less, even more preferably 22 or less, and even more preferably 21 or less. In the oral composition of the present invention, the mass ratio of component (A) to component (B) [(B) / (A)] is 1 to 30, preferably 2 to 27, more preferably 4 to 24, even more preferably 12 to 22, and even more preferably 16 to 21.

[0026] The oral composition of the present invention may be in any suitable form, either solid or liquid. Suitable embodiments of the oral composition of the present invention include, for example, a solid oral composition and a liquid oral composition described below.

[0027] [Solid composition for oral administration] The oral solid composition of the present invention is not particularly limited in shape as long as it is solid at room temperature (20°C ± 15°C), and examples thereof include various shapes such as powder, granules, tablets, rods, plates, and blocks. The oral solid composition of the present invention usually has a solid content of 95% by mass or more, preferably 97% by mass or more. The upper limit of the solid content is not particularly limited, and may be 100% by mass.

[0028] The solid composition for oral administration of the present invention contains a polyalkoxyflavonoid represented by the above formula (1) as component (A). The specific structure of the polyalkoxyflavonoid is as described above.

[0029] From the viewpoint of providing excellent physiological effects, the component (A) is preferably one or more selected from nobiletin and tangeretin, and more preferably nobiletin.

[0030] The content of component (A) in the oral solid composition of the present invention is 3% by mass or more, preferably 4% by mass or more, more preferably 4.5% by mass or more, from the viewpoint of providing an excellent physiological effect, and from the viewpoint of suppressing roughness on the tongue when orally taken and suppressing the bitterness and astringency of the polyalkoxyflavonoid itself, it is 50% by mass or less, preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 20% by mass or less, and even more preferably 8% by mass or less. The content of component (A) in the oral solid composition of the present invention is 3 to 50% by mass, preferably 4 to 40% by mass, more preferably 4.5 to 30% by mass, even more preferably 4.5 to 20% by mass, and even more preferably 4.5 to 8% by mass. The method of analysis of component (A) is as described above.

[0031] The solid composition for oral administration of the present invention contains chlorogenic acids as component (B). The specific composition of the chlorogenic acids is as described above.

[0032] The content of component (B) in the oral solid composition of the present invention is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, and even more preferably 80% by mass or more, from the viewpoint of suppressing roughness on the tongue when orally taken, and is preferably 97% by mass or less, more preferably 96% by mass or less, and even more preferably 95.5% by mass or less, from the viewpoint of suppressing bitterness and astringency of the oral solid composition. The content of component (B) in the oral solid composition of the present invention is preferably 50 to 97% by mass, more preferably 60 to 96% by mass, even more preferably 70 to 96% by mass, and even more preferably 80 to 95.5% by mass. The method of analysis of component (B) is as described above.

[0033] In the oral solid composition of the present invention, the mass ratio of component (A) to component (B) [(B) / (A)] is 1 or more, preferably 2 or more, more preferably 4 or more, even more preferably 12 or more, and even more preferably 16 or more, from the viewpoint of suppressing roughness on the tongue when orally taken, and is 30 or less, preferably 27 or less, more preferably 24 or less, even more preferably 22 or less, and even more preferably 21 or less, from the viewpoint of suppressing bitterness and astringency of the oral solid composition. In the oral solid composition of the present invention, the mass ratio of component (A) to component (B) [(B) / (A)] is 1 to 30, preferably 2 to 27, more preferably 4 to 24, even more preferably 12 to 22, and even more preferably 16 to 21.

[0034] The solid composition for oral administration of the present invention may contain, as desired, one or more additives such as sweeteners, acidulants, amino acids, proteins, vitamins, minerals, flavors, fruit juices, plant extracts, esters, colorants, emulsifiers, milk components, cocoa powder, seasonings, vegetable oils and fats, antioxidants, preservatives, pH adjusters, gelling agents, carriers, etc. The content of the additives may be appropriately set within a range that does not impair the object of the present invention.

[0035] The type of the oral solid composition of the present invention is not particularly limited and can be appropriately selected according to the purpose. For example, instant drinks, dairy products such as cheese, frozen desserts such as ice cream, confectionery such as candy, gum, chocolate, cookies, bread, etc., noodles such as soba and udon, health, beauty and nutritional supplements such as supplements, medicines and quasi-drugs such as powders, tablets, granules, capsules, and lozenges, etc. can be mentioned.

[0036] Among these, supplements, powders, tablets, granules, and instant drinks are preferred. Oral solid compositions such as supplements, powders, tablets, and granules are in a form to be directly ingested, and are preferred embodiments of the present invention because they provide excellent physiological effects due to component (A) and / or component (B). In addition, an instant beverage is a preferred embodiment of the present invention, since it provides excellent physiological effects due to the components (A) and / or (B) when diluted with a liquid according to a prescribed method of use and orally ingested as a reconstituted beverage. The liquid is not particularly limited as long as it can be reconstituted into a beverage, and examples of the liquid include water, carbonated water, milk, soy milk, etc., and the temperature of the liquid does not matter. The dilution ratio may be in accordance with the prescribed method of use, and is usually 20 to 600 times by mass, preferably 80 to 600 times by mass. The reconstituted beverage prepared from the instant beverage according to the prescribed method of use can have the same configuration as the oral liquid composition described below in terms of the contents of the components (A) and (B), the mass ratio [(B) / (A)], and the pH in the reconstituted beverage.

[0037] The instant beverage may be, for example, a container filled in a bottle or the like, and a cupful is measured with a spoon or the like when consumed; a cup-type containing a single cupful; or a stick-type packaged in portions for each cupful. The volume of the cup is preferably 30 to 320 mL, and the content of the portioned package can be appropriately set to match the cup volume. The portioned package can be packaged in a packaging material made of aluminum vapor deposition film or the like. The container and packaging material may be filled with nitrogen gas, and packaging materials with low oxygen permeability are preferred in terms of maintaining quality.

[0038] [Oral liquid composition] The form of the oral liquid composition of the present invention is not particularly limited as long as it has fluidity at room temperature (20°C ± 15°C), and may be, for example, a concentrated form. Examples of the oral liquid composition of the present invention include RTD (drinks); concentrated drinks; dairy products such as yogurt, processed milk, and fermented milk; oils and fats and processed oils and fats such as salad oil, tempura oil, margarine, mayonnaise, shortening, whipped cream, and dressing; seasonings such as sauces and sauces; and health, beauty, and nutritional supplements such as drinks.

[0039] Among them, RTD (beverage) is preferable because it is easy to enjoy the effects of the present invention. RTD (beverage) may be a packaged beverage. The container is not particularly limited as long as it is a normal packaging container, and examples thereof include molded containers mainly composed of polyethylene terephthalate (so-called PET bottles), metal cans, paper containers combined with metal foil or plastic film, bottles, etc.

[0040] The oral liquid composition of the present invention contains a polyalkoxyflavonoid represented by the above formula (1) as component (A). The specific structure of the polyalkoxyflavonoid is as described above.

[0041] From the viewpoint of providing excellent physiological effects, the component (A) is preferably one or more selected from nobiletin and tangeretin, and more preferably nobiletin.

[0042] The content of component (A) in the oral liquid composition of the present invention is 0.03% by mass or more, preferably 0.04% by mass or more, from the viewpoint of providing an excellent physiological effect, and is preferably 1% by mass or less, more preferably 0.6% by mass or less, from the viewpoint of suppressing turbidity of the liquid and suppressing the bitterness and astringency of the polyalkoxyflavonoid itself. The content of component (A) in the oral liquid composition of the present invention is preferably 0.03-1% by mass, more preferably 0.04-0.6% by mass. The method for analyzing the content of component (A) is as described above.

[0043] The solid composition for oral administration of the present invention contains chlorogenic acids as component (B). The specific composition of the chlorogenic acids is as described above.

[0044] The content of component (B) in the oral liquid composition of the present invention is preferably 0.05% by mass or more, more preferably 0.1% by mass or more, even more preferably 0.2% by mass or more, even more preferably 0.4% by mass or more, and even more preferably 0.6% by mass or more, from the viewpoint of suppressing the turbidity of the liquid, and is preferably 2% by mass or less, more preferably 1.2% by mass or less, and even more preferably 0.8% by mass or less, from the viewpoint of suppressing the bitterness and astringency of the oral liquid composition. The content of component (B) in the oral liquid composition of the present invention is preferably 0.05 to 2% by mass, more preferably 0.1 to 1.2% by mass, even more preferably 0.2 to 1.2% by mass, even more preferably 0.4 to 1.2% by mass, and even more preferably 0.6 to 0.8% by mass. The method of analysis of the content of component (B) is as described above.

[0045] In the oral liquid composition of the present invention, the mass ratio of component (A) to component (B) [(B) / (A)] is 1 or more, preferably 2 or more, more preferably 4 or more, even more preferably 8 or more, still more preferably 12 or more, and still more preferably 16 or more, and in terms of suppressing the bitterness and astringency of the oral liquid composition, is 30 or less, preferably 27 or less, more preferably 24 or less, even more preferably 22 or less, and still more preferably 21 or less. In the oral liquid composition of the present invention, the mass ratio of component (A) to component (B) [(B) / (A)] is 1 to 30, preferably 2 to 27, more preferably 4 to 24, even more preferably 8 to 24, still more preferably 12 to 22, and still more preferably 16 to 21.

[0046] From the viewpoint of suppressing bitterness and astringency, the oral liquid composition of the present invention has a pH (20°C) of preferably 3 or more, more preferably 3.5 or more, even more preferably 4 or more, and preferably 7 or less, more preferably 6.8 or less, even more preferably 6.5 or less. The oral liquid composition of the present invention has a pH (20°C) of preferably 3 to 7, more preferably 3.5 to 6.8, even more preferably 4 to 6.5. The pH is measured with a pH meter after adjusting the temperature to 20°C.

[0047] The oral liquid composition of the present invention may be a tea or non-tea beverage, such as a soft drink, a carbonated drink, a tea beverage, a fruit juice beverage, a vegetable beverage, a dairy beverage, or an alcoholic beverage.

[0048] When the oral liquid composition of the present invention is a packaged beverage, it may be heat sterilized. The heat sterilization method is not particularly limited as long as it meets the conditions stipulated in the applicable laws and regulations (Food Sanitation Law in Japan). For example, the beverage may be filled into a container, sealed or sealed, and then sterilized, or the beverage may be sterilized in a sterilizer equipped with a thermometer or the like, or sterilized in a filter or the like, and then automatically filled into a container, sealed or sealed. More specifically, examples of the method include retort sterilization, high temperature short time sterilization (HTST method), and ultra-high temperature sterilization (UHT method). The container is as described above.

[0049] The oral liquid composition of the present invention has improved solubility of polyalkoxyflavonoid in water and excellent dispersibility, so that the turbidity of the liquid is suppressed. For example, when the content of component (A) in the oral liquid composition is adjusted to 0.05% by mass, the turbidity (OD660) of the packaged beverage can be 0.35 or less, preferably 0.31 or less, more preferably 0.2 or less, and even more preferably 0.2 or less. The lower limit of the turbidity (OD660) is not particularly limited, and may be 0. Here, in this specification, "turbidity" refers to the absorbance at a wavelength of 660 nm measured at 20°C using a spectrophotometer in a 90° transmission scattering comparison mode. Specifically, it can be measured by the method described in the Examples below. The lower the turbidity (OD660) value, the clearer the beverage.

[0050] The oral composition of the present invention can be produced according to a conventional method, and any suitable method can be used. For example, it can be produced by mixing components (A) and (B) and, if necessary, other components, and adjusting the content of component (A) and the mass ratio [(B) / (A)]. The order of mixing components (A) and (B) is not particularly limited, and they may be added and mixed in any order, or both may be added and mixed at the same time. As the mixing method, an appropriate method such as stirring or shaking can be adopted, and a mixing device may be used. The mixing method of the mixing device may be a container rotation type or a container fixed type. As the container rotation type, for example, a horizontal cylinder type, a V type, a double cone type, a cube type, etc. can be adopted. As the container fixed type, for example, a ribbon type, a screw type, a conical screw type, a paddle type, a fluidized bed type, a Phillips blender, etc. can be adopted. In addition, when the oral composition of the present invention is an oral solid composition, it may be granulated by a known granulation method. Examples of the granulation method include spray granulation, fluidized bed granulation, compression granulation, rolling granulation, stirring granulation, extrusion granulation, and powder coating granulation. The granulation conditions can be appropriately selected depending on the granulation method. In addition, when making into tablets, either wet tableting or dry tableting may be used, and a known compression molding machine can be used. Furthermore, in the case of a concentrated liquid, known concentration methods can be used, such as an atmospheric concentration method in which the solvent is evaporated at atmospheric pressure, a reduced pressure concentration method in which the solvent is evaporated at reduced pressure, and a membrane concentration method in which the solvent is removed by membrane separation.

[0051] When the oral composition of the present invention is a solid oral composition, it is possible to easily produce an oral solid composition that suppresses roughness on the tongue when taken orally, even without the step of dissolving component (A) in an aqueous ethanol solution during the production process. Also, when the oral composition of the present invention is a liquid oral composition, it is possible to easily produce a beverage that suppresses liquid turbidity, even without the step of dissolving component (A) in an aqueous ethanol solution during the production process. That is, from the viewpoint of easily producing an oral composition, it is preferable that the present invention does not include a step of dissolving component (A) in an aqueous ethanol solution during the production process.

[0052] When the oral composition of the present invention is a solid oral composition, it is possible to easily produce an oral solid composition that suppresses roughness on the tongue when taken orally, even if the manufacturing process does not include a step of heating and dissolving component (A). Also, when the oral composition of the present invention is a liquid oral composition, it is possible to easily produce a beverage that suppresses liquid turbidity, even if the manufacturing process does not include a step of heating and dissolving component (A). That is, from the viewpoint of easily producing an oral composition, it is preferable that the manufacturing process does not include a step of heating and dissolving component (A). Specifically, the heating temperature of component (A) is preferably less than 90°C, more preferably less than 50°C, and most preferably does not substantially include a heating step.

[0053] [Suppression method] The method of the present invention for suppressing roughness on the tongue during oral intake and cloudiness in a beverage form caused by polyalkoxyflavonoids is to make components (A) and (B) coexist in a ratio in which the mass ratio of component (A) to component (B) [(B) / (A)] is 1 to 30. This can improve the solubility of polyalkoxyflavonoids in water. A preferred embodiment is, for example, an embodiment in which chlorogenic acids are contained in an oral product containing polyalkoxyflavonoids. The contents of components (A) and (B) in the solid content of the oral product and the mass ratio [(B) / (A)] are as described above. Specific embodiments of components (A) and (B) and the oral product are also as described above. EXAMPLES

[0054] 1. Analysis of polyalkoxyflavonoids An Agilent Technologies high performance liquid chromatograph was used, equipped with a Chemicals Evaluation and Research Institute L-Column ODS-2 (4.6 mmφ×50 mm, 2 μm), and the gradient method was used at a column temperature of 40°C.

[0055] The analysis conditions are as follows. The sample injection volume was 10 μL, mobile phase A liquid was a 0.1 mass % aqueous trifluoroacetic acid solution, and B liquid was acetonitrile, and the liquids were delivered at 1.0 mL / min.

[0056] Concentration gradient conditions (volume%) Time Eluent A Eluent B 0 minutes 99% 1% 1 minute 99% 1% 4 minutes 5% 95% 5 minutes 5% 95% 5.01 minutes 99% 1% 6 minutes 99% 1%

[0057] Nobiletin was detected by quantifying absorbance at a wavelength of 320 nm. In addition to the above-mentioned method, nobiletin and tangeretin can also be analyzed using the method described in JP 2015-202065 A.

[0058] 2. Analysis of chlorogenic acids The analytical equipment used was HPLC. The model numbers of the components of the device are as follows: UV-VIS detector: SPD-20A (Shimadzu Corporation) Column oven: CTO-20AC (Shimadzu Corporation) Pump: LC-20AD (Shimadzu Corporation) Autosampler: SIL-20AC (Shimadzu Corporation) Column: Cadenza CD-C18, inner diameter 4.6 mm x length 150 mm, particle size 3 μm (Intact Co., Ltd.)

[0059] The analysis conditions are as follows. Sample injection volume: 10μL ·Flow rate: 1.0mL / min UV-VIS detector wavelength setting: 325nm Column oven temperature setting: 35℃ Eluent C: 50 mM acetic acid, 0.1 mM 1-hydroxyethane-1,1-diphosphonic acid, 10 mM sodium acetate, 5 (V / V)% acetonitrile solution Eluent D: Acetonitrile

[0060] Concentration gradient conditions (volume%) Time Eluent C Eluent D 0.0 minutes 100% 0% 10.0 minutes 100% 0% 15.0 minutes 95% 5% 20.0 minutes 95% 5% 22.0 minutes 92% 8% 50.0 minutes 92% 8% 52.0 minutes 10% 90% 60.0 minutes 10% 90% 60.1 minutes 100% 0% 70.0 minutes 100% 0%

[0061] 3-Caffeoylquinic acid: 5.3min 5-Caffeoylquinic acid: 8.8min 4-Caffeoylquinic acid: 11.6 min 3-Ferulacinic acid: 13.0 min 5-Ferulacinic acid: 19.9 min 4-Ferulacinic acid: 21.0 min 3,4-Dicaffeoylquinic acid: 36.6 min 3,5-dicaffeoylquinic acid: 37.4 min 4,5-dicaffeoylquinic acid: 44.2 min From the area% calculated here, the content (mass%) of chlorogenic acids was calculated using 5-caffeoylquinic acid (Tokyo Chemical Industry Co., Ltd.) as a standard substance.

[0062] 3. Turbidity (OD660) measurement The polyalkoxyflavonoid concentration of the sample was adjusted to 0.05% by mass, and the absorbance at a wavelength of 660 nm was measured at 20° C. using a spectrophotometer (U2810, manufactured by Hitachi) in a 90° transmission scattering comparison mode.

[0063] 4. pH Measurement The temperature was adjusted to 20° C., and the pH was measured using a pH meter (HORIBA compact pH meter, manufactured by Horiba, Ltd.).

[0064] Examples 1 to 5 and Comparative Example 1 An instant beverage was obtained by uniformly mixing each component in the proportions shown in Table 1. The obtained instant beverage was analyzed and subjected to a sensory evaluation by the following method. The results are shown in Table 1.

[0065] Sensory evaluation 1 A sensory test was conducted by a panel of five experts on the "roughness on the tongue when orally taken" of each reconstituted beverage, which was prepared by diluting each instant beverage with water at 20°C so that the component (A) was 0.05% by mass after dilution. The sensory test was conducted after each expert panel agreed to use the following evaluation criteria for "roughness on the tongue when orally taken". The final evaluation was then determined by discussion based on the scores determined by each expert panel.

[0066] Evaluation criteria for roughness on the tongue during oral ingestion Rating 5: No roughness felt (corresponding to Example 5). 4: Not very rough feeling. 3: Feels slightly rough. 2: It feels rough. 1: Strongly rough feeling (corresponding to Comparative Example 1).

[0067] [Table 1]

[0068] Examples 6 to 10 and Comparative Example 2 The components were mixed in the proportions shown in Table 2, then sterilized at ultra-high temperature for 30 seconds (UHT sterilization, 98°C, 30 seconds), and filled into transparent PET bottles to prepare packaged beverages. The resulting packaged beverages were then analyzed and their turbidity was measured. The results are shown in Table 2.

[0069] [Table 2]

[0070] Example 11 and Comparative Example 3 A powder composition for oral administration was obtained by mixing the components in the proportions shown in Table 3. The obtained powder composition for oral administration was subjected to analysis and sensory evaluation. The results are shown in Table 3.

[0071] Sensory evaluation 2 After 0.1 g of each oral powder composition was placed in the mouth, it was dissolved in the mouth by saliva and completely disappeared. A sensory test was conducted by five expert panelists regarding "roughness on the tongue when taken orally". The sensory test was conducted after each expert panel agreed to use the following evaluation criteria for "roughness on the tongue when taken orally". The final evaluation was then determined by discussion based on the scores determined by each expert panel.

[0072] Evaluation criteria for roughness on the tongue during oral ingestion Rating 5: No roughness felt. 4: Not very rough feeling. 3: Feels slightly rough. 2: It feels rough. 1: There is a strong feeling of roughness.

[0073] [Table 3]

[0074] Tables 1 to 3 show that by incorporating chlorogenic acids in a specific mass ratio relative to polyalkoxyflavonoid, the solubility of polyalkoxyflavonoid in water is increased, and the roughness on the tongue when taken orally and the cloudiness when made into a beverage can be suppressed.

Claims

1. The following components (A) and (B): (A) 4 to 40% by mass of nobiletin, and (B) Monocaffeoylquinic acid 60 to 96% by mass Contains The mass ratio of component (A) to component (B) [(B) / (A)] is 1 to 30; Oral solid composition.

2. The following components (A) and (B): (A) 0.04 to 0.6% by mass of nobiletin, and (B) Monocaffeoylquinic acid 0.05 to 2% by mass Contains The mass ratio of component (A) to component (B) [(B) / (A)] is 1 to 30; Oral liquid composition.

3. The following components (A) and (B): (A) 4 to 40% by mass of nobiletin, and (B) Monocaffeoylquinic acid 60 to 96% by mass and a mass ratio of component (A) to component (B) [(B) / (A)] is 1 to 30.

4. The following components (A) and (B): (A) nobiletin 0.04 to 0.6 mass %, and (B) Monocaffeoylquinic acid 0.05 to 2% by mass and a mass ratio of component (A) to component (B) [(B) / (A)] is 1 to 30.

Citation Information

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