WO2017171023A1 - Beverage in which hesperidin precipitation has been inhibited - Google Patents

Beverage in which hesperidin precipitation has been inhibited Download PDF

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Publication number
WO2017171023A1
WO2017171023A1 PCT/JP2017/013647 JP2017013647W WO2017171023A1 WO 2017171023 A1 WO2017171023 A1 WO 2017171023A1 JP 2017013647 W JP2017013647 W JP 2017013647W WO 2017171023 A1 WO2017171023 A1 WO 2017171023A1
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beverage
ppm
hesperidin
rebm
juice
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PCT/JP2017/013647
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French (fr)
Japanese (ja)
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友之 西堀
聡一郎 浦井
彬子 和泉
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サントリーホールディングス株式会社
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Priority to JP2017547177A priority Critical patent/JPWO2017171023A1/en
Publication of WO2017171023A1 publication Critical patent/WO2017171023A1/en

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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/02Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/70Clarifying or fining of non-alcoholic beverages; Removing unwanted matter
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof

Definitions

  • the embodiment of the present invention relates to a beverage in which precipitation of hesperidin is suppressed.
  • Beverages containing orange juice tend to precipitate at the bottom of the container after about one month has passed since manufacture.
  • the precipitate is mainly a stack of pulp derived from orange juice, on which white precipitate is further accumulated. It is known that this white precipitate is caused by precipitation of hesperidin having low solubility contained in orange juice. The presence of the white precipitate looks bad and impairs the appearance of the beverage, resulting in a reduction in the commercial value of the beverage. In particular, in beverages filled in transparent containers such as PET bottles that have been widely used in recent years, the quality of the appearance has a great influence on the commercial value.
  • An object of the present invention is to provide a beverage in which the occurrence of precipitation due to hesperidin is suppressed.
  • the present inventors have surprisingly added hesperidin when Rebaudioside (hereinafter referred to as “Reb”) D and / or RebM is added. It has been found that precipitation of hesperidin is suppressed in beverages. Based on this finding, the present inventors have completed the present invention.
  • Reb Rebaudioside
  • the embodiment of the present invention is not limited to this, but the following conditions (A), (B) and (C): (A) containing RebD and / or RebM, (B) contains hesperidin, and (C) the beverage has a Brix (in terms of sucrose) of 3 to 15. Provide a beverage that meets the requirements.
  • a beverage in which precipitation of hesperidin is suppressed can be provided.
  • precipitation tends to proceed especially when sucrose or fructose is added to the beverage.
  • RebD and / or RebM are used in place of these saccharides, and the amount added can be very small. Therefore, the present invention not only effectively suppresses the formation of hesperidin precipitate, but also can provide a beverage having a lower calorie while exhibiting sweetness equivalent to that of sucrose and fructose.
  • FIG. 1 is a graph showing the effect of inhibiting hesperidin precipitation by the addition of RebA, RebD or RebM.
  • the beverage according to the embodiment of the present invention has the following conditions (A), (B) and (C): (A) containing RebD and / or RebM, (B) contains hesperidin, and (C) the beverage has a Brix (in terms of sucrose) of 3 to 15. It is a beverage that meets the requirements.
  • the beverage according to the embodiment of the present invention includes RebD and / or RebM.
  • Reb (Rebaudioside) is known as a sweetening component contained in stevia extract.
  • Stevia extract is extracted and purified from dried Stevia leaves.
  • Stevia is a perennial plant of Chrysanthemum that originates in Paraguay, South America, and its scientific name is Stevia Rebaudiana Bertoni.
  • Stevia contains ingredients that are about 300 times more sweet than sugar and is cultivated to extract these sweet ingredients and use them as natural sweeteners.
  • Reb RebA, RebB, RebC, RebD, and RebE are known.
  • the existence of various glycosides such as RebM described in JP 2012-504552 has been reported.
  • RebA is evaluated as a sweetener having high sweetness and good quality sweetness, and is widely used.
  • RebD and RebM can be obtained from the market or can be synthesized by an organic chemical method.
  • RebD and RebM can be separated and purified using stevia extract as a starting material.
  • RebD can be purified according to the method described in US8414949, and RebM can be purified according to the method described in Foods 2014, 3 (1), 162-175; doi: 10.3390 / foods 3010262. it can.
  • RebD and RebM may be analyzed by any method.
  • RebD and RebM can be analyzed by a high performance liquid chromatography analyzer (HPLC) set to the conditions described in JP-T-2012-504552.
  • HPLC high performance liquid chromatography analyzer
  • RebA may be included in the beverage according to the embodiment of the present invention.
  • RebA can be obtained from the market or can be synthesized by an organic chemical method.
  • RebA can be separated and purified using stevia extract as a starting material.
  • RebA can be purified according to the method described in JP-T 2009-517043.
  • RebA may be analyzed by any method, and can be analyzed by the same method as RebD and RebM as described above.
  • the content of various Rebs in the beverage according to the embodiment of the present invention is not particularly limited as long as the effect of the present invention is obtained.
  • the content of RebD can be, for example, 100 to 500 ppm in the beverage.
  • the content of RebD is preferably 120 ppm or more, 140 ppm or more, 150 ppm or more, 180 ppm or more, or 200 ppm or more, and preferably 480 ppm or less, 460 ppm or less, 450 ppm or less, 430 ppm or less, or 400 ppm or less.
  • the content of RebM can be, for example, 100 to 500 ppm in the beverage.
  • the content of RebM is preferably 120 ppm or more, 140 ppm or more, 150 ppm or more, 180 ppm or more, or 200 ppm or more, and preferably 480 ppm or less, 460 ppm or less, 450 ppm or less, 430 ppm or less, or 400 ppm or less.
  • the content of RebA can be, for example, 100 to 500 ppm in the beverage.
  • the content of RebA is preferably 120 ppm or more, 140 ppm or more, 150 ppm or more, 180 ppm or more, or 200 ppm or more, and preferably 480 ppm or less, 460 ppm or less, 450 ppm or less, 430 ppm or less, or 400 ppm or less.
  • ppm used in this specification means ppm of weight / volume (w / v) unless otherwise specified.
  • the total content in the beverage can be set within a required range, and set within a range that does not cause a problem in flavor. can do.
  • the total content in the beverage is 100 to 500 ppm, preferably 150 to 450 ppm, more preferably 200 to 400 ppm, and still more preferably 250 to 350 ppm. be able to.
  • the total content of two or more of RebA, RebD, and RebM in the beverage can be set within the required range in the same manner as described above, and there is no problem in flavor.
  • the total content in the beverage is 100 to 500 ppm, preferably 150 to 450 ppm, more preferably 200 to 400 ppm, and still more preferably.
  • the total content in the beverage is 100 to 500 ppm, preferably 150 to 450 ppm, more preferably 200 to 400 ppm, More preferably, it can be 250 to 350 ppm.
  • the mass ratio (the ratio of the RebM content to the RebD content (RebM / RebD)) is, for example, 0. 01 to 10, preferably 0.1 to 1.
  • the mass ratio (the ratio of the RebD content to the RebA content (RebD / RebA)) is, for example, 0. It is 01 to 40, and preferably 0.2 to 20.
  • the mass ratio (the ratio of the RebM content to the RebA content (RebM / RebA)) is, for example, 0. 01 to 10, preferably 0.05 to 5.
  • the beverage according to the embodiment of the present invention is not particularly limited, but the sweetness level can be adjusted so that an appropriate sweetness can be felt.
  • the sweetness level for example, the sucrose equivalent Brix of the beverage according to the embodiment of the present invention is 3 to 15, preferably 4 to 12, more preferably 8 to 12, and still more preferably 8 to 11. .
  • the Brix is less than 3, the sweetness derived from the stevia extract tends not to be sufficiently felt as a beverage taste.
  • the Brix exceeds 15, the sweetness becomes too strong and the flavor tends to deteriorate.
  • Brix in terms of sucrose can be calculated from the sweetness of Reb with respect to sucrose and the content of Reb.
  • RebA has a sweetness 300 times
  • RebD has a sweetness of 285 times
  • RebM has a sweetness of 285 times that of sucrose. Therefore, Brix in terms of sucrose can be calculated from a value obtained by multiplying the RebA content by 300 times, a value obtained by multiplying the RebD content by 285 times, and a value obtained by multiplying the RebM content by 285 times.
  • the amount of Brix equivalent to 1 in terms of sucrose is 33.3 ppm for RebA, 35.1 ppm for RebD, and 35.1 ppm for RebM.
  • the sucrose equivalent Brix of the beverage according to the embodiment of the present invention can be calculated from the contents of RebD and RebM (including RebA in some cases) as described above, but sweetness other than RebA, RebD and RebM When a scent is used, the Brix is expressed as a sum of sweetness levels of all sweeteners. At this time, Brix of the beverage of the present invention can be measured by, for example, a commercially available Brix meter.
  • Sweeteners other than RebA, RebD, and RebM are not particularly limited, and examples thereof include saccharides such as sucrose and fructose, and high-intensity sweeteners such as aspartame, sucralose, and acesulfame K.
  • sucrose When sucrose is used, its content in the beverage is, for example, 3 to 15% by weight, preferably 4 to 12% by weight, more preferably 8 to 11% by weight, but is not particularly limited thereto.
  • fructose When fructose is used, the content in the beverage is, for example, 3 to 15% by weight, preferably 4 to 12% by weight, more preferably 8 to 11% by weight, but is not particularly limited thereto.
  • sweeteners such as sucrose and fructose
  • commercially available products can be used, and the form thereof may be powder or liquid (liquid sugar), and is not particularly limited.
  • “Wt%” used in this specification means weight% of weight / volume (w / v) unless otherwise specified.
  • HPLC high performance liquid chromatography
  • Hesperidin (C 28 H 34 O 15 ) is a compound having a flavonoid skeleton, and is a component often found in citrus fruits. Hesperidin is a component detected in lemon, orange, mandarin orange, yuzu, lime, ponkan, hassaku, kumquat, seeker, and the like, and has a slight bitter taste.
  • the content of hesperidin in the beverage according to the embodiment of the present invention is not particularly limited, and is, for example, 1 to 250 ppm.
  • the content of hesperidin in the beverage of the present invention is preferably 10 ppm or more, 50 ppm or more, 100 ppm or more, or 130 ppm or more, and preferably 230 ppm or less, 200 ppm or less, or 180 ppm or less.
  • the adjustment of the content of hesperidin in the beverage is not particularly limited, but can be performed by appropriately adjusting the amount of the naturally-derived material containing the component.
  • the amount of hesperidin in citrus fruits has been reported in, for example, Kinki Chugoku Shikoku Agricultural Research Center Research Report No. 5, 2005, Yoichi Nogata, “Research on Functional Components of Citrus Fruits and Their Effective Use”
  • the juice to be used can be selected and examined with reference to such materials.
  • orange juice is particularly preferable.
  • the content of hesperidin in the beverage according to the embodiment of the present invention can be measured using a known method such as high performance liquid chromatography mass spectrometry (LC-MS). For example, it can be measured under the following conditions.
  • LC-MS high performance liquid chromatography mass spectrometry
  • sample Beverages containing carbon dioxide gas remove carbon dioxide by a conventional method.
  • 10 g of the solution is weighed in the centrifuge tube (A).
  • the Brix of the sample is 20 ° Bx or more, weigh 5 g, and when the Brix is 40 ° Bx or more, weigh 2 g and dilute to 10 mL with distilled water for liquid chromatography.
  • centrifuge 3000 ⁇ g, 30 minutes, 20 ° C.
  • the supernatant is transferred to another centrifuge tube (B).
  • Centrifuge 3000 ⁇ g, 30 minutes, 20 ° C.
  • the supernatant collected in the centrifuge tube (B) is further centrifuged (3000 ⁇ g, 30 minutes, 20 ° C.), and the resulting supernatant is transferred to a 50 mL volumetric flask and made up with ethanol.
  • the well-mixed supernatant is filtered through a PTFE filter (Toyo Roshi Kaisha, ADVANTEC DISMIC-25HP 25HP020AN, pore size 0.20 ⁇ m, diameter 25 mm) previously washed with ethanol to obtain an analytical sample.
  • a PTFE filter Toyo Roshi Kaisha, ADVANTEC DISMIC-25HP 25HP020AN, pore size 0.20 ⁇ m, diameter 25 mm
  • HPLC apparatus Prominance series (manufactured by Shimadzu Corporation, system controller: SCL-10A, liquid pump: LC-20AD, online degassing apparatus: DGU-20A3, autosampler: SIL-20AC, column oven : CTO-20A, and UV / VIS detector: SPD-20A)
  • Mobile phase A 0.1% aqueous solution of formic acid
  • Mobile phase B acetonitrile
  • Flow rate 0.6 mL / min
  • Concentration gradient conditions 0.0 to 1.0 minutes (15% B) ⁇ 12.0 minutes (25% B) ⁇ 20.0 minutes (75% B) ⁇ 20.0 to 22.0 minutes (100% B) ), 3.0 minutes equilibration with initial mobile phase
  • Sample injection injection volume 5.0 ⁇ L Peak detection time: Although confirmation with a standard is required, it
  • the ratio of the content of RebD to the content of hesperidin is, for example, 0.01 to 10, preferably 0.1 to 5 More preferably, it is 0.5-2.
  • the ratio of the content of RebM to the content of hesperidin is, for example, 0.01 to 10, preferably 0.1 to 5 More preferably, it is 0.5-2.
  • the ratio of the content of RebA to the content of hesperidin is, for example, 0.01 to 10, preferably 0.1 to 5 More preferably, it is 0.5-2.
  • the beverage according to the embodiment of the present invention may contain fruit juice.
  • the type of fruit juice is not particularly limited.
  • fruit juice of citrus fruits such as orange juice, grapefruit juice, mandarin juice, mandarin juice, apple juice, grape juice, peach juice, strawberry juice, banana juice, cherry juice, melon Fruit juice, watermelon juice, mango juice, papaya juice, kiwi juice, Japanese pear juice, pear juice, oyster juice, ume juice, muscat juice, pineapple juice, passion fruit juice, guava juice, apricot juice, plum juice, cranberry juice, Pomegranate juice can be mentioned.
  • the drink which concerns on embodiment of this invention can contain 1 type, or 2 or more types of fruit juice.
  • citrus fruit juice is preferable, and orange juice is particularly preferable.
  • fruit juice can be used regardless of manufacturing methods, such as straight fruit juice and concentrated fruit juice. In view of good handling, concentrated reduced fruit juice is preferable.
  • the fruit juice ratio can be 1 to 100%.
  • the fruit juice ratio is preferably 1 to 100%, more preferably 10 to 100%. It can be said that a higher fruit juice ratio is preferable in order to exert the effect of inhibiting the precipitation of hesperidin.
  • the “fruit juice ratio” refers to the relative concentration when straight juice obtained by squeezing fruit juice is taken as 100%.
  • Yuzu and Sudachi may use 4.3 and 6.6, respectively, as the acidity standard (citric acid equivalent) (%).
  • the method for calculating the fruit juice rate is, for example, that the standard of acidity of lime juice in JAS standards is 6% in terms of citric acid. Therefore, when 6% by weight of concentrated lime juice with an acidity of 30% is blended in the beverage, fruit juice The rate is 30%.
  • the fruit juice ratio can be calculated by converting the fruit juice not described above into a relative concentration when straight fruit juice is 100%. For example, when 5% by weight of double concentrated fruit juice is used in a beverage, the juice rate of the beverage is 10%.
  • the fruit juice ratio is a sum of the fruit juice ratios of all the fruit juices calculated based on the above.
  • the fruit juice ratio obtained by this calculation usually corresponds to the ratio of the fruit juice shown in the beverage container (the numerical value indicated as “fruit juice ⁇ %”).
  • polyphenols such as catechins, plant extracts, caffeine, cinnamaldehyde, caramel color, and sweeteners (sugar, isomerized liquid sugar) , Sugars such as aspartame, sucralose, and acesulfame K), flavorings, acidulants (citric acid, tartaric acid, malic acid, phosphoric acid, lactic acid), colorants, fruit juice, fruit puree, milk , Dairy products, other flavors, and fortifiers (vitamins, calcium, minerals, amino acids), and the like may be further included. You may mix
  • the type of beverage is not particularly limited and may be any of carbonated beverage, non-carbonated beverage, alcoholic beverage, non-alcoholic beverage, nutritional beverage, functional beverage, and the like.
  • the method is not particularly limited, and carbon dioxide may be generated in the beverage by fermentation, or artificially carbon dioxide. May be injected into the beverage.
  • the gas pressure the temperature is 20 ° C., for example, 1.0 ⁇ 3.0 kgf / cm 2, preferably 1.2 ⁇ 2.0 kgf / cm 2, more preferably 1.5 ⁇ It can be 1.8 kgf / cm 2 .
  • Carbon dioxide gas can be added using methods known to those skilled in the art.
  • the carbon dioxide pressure in the beverage can be measured, for example, using a gas volume measuring device GVA-500A manufactured by Kyoto Electronics Industry.
  • the beverage according to the embodiment of the present invention is not particularly limited, but can be packed in a container.
  • a container of any form / material can be used.
  • a container such as a bottle, a can, a barrel, or a plastic bottle may be used.
  • the method for filling the beverage container is not particularly limited.
  • a method for suppressing precipitation of hesperidin is provided.
  • a method according to an embodiment of the present invention is a method for suppressing precipitation of hesperidin in a beverage, The following steps (A), (B) and (C): (A) A step of blending RebD and / or RebM, (B) a step of blending hesperidin, and (C) a step of adjusting Brix (converted to sucrose) of the beverage to 3 to 15, Is the above method.
  • various elements such as the types of ingredients in the beverage and their contents are as described above for the beverage of the present invention, or are obvious from them.
  • the method of this invention can also include the process of mix
  • various processes may be performed simultaneously, may be performed separately, and the order of processes may be changed. The timing of various processes can be adjusted as appropriate according to the situation.
  • a beverage sample was prepared as follows.
  • Concentrated orange fruit juice was added to pure water so that the fruit juice ratio would be 100% to prepare a beverage sample containing only fruit juice. At this time, the content of hesperidin in the beverage sample was 140 ppm.
  • sucrose type liquid sugar ES67B, manufactured by Dainippon Meiji Sugar Co., Ltd.
  • fructose glucose liquid so as to have the content shown in the table below.
  • Sugars F-55, manufactured by Nippon Corn Starch Co., Ltd.
  • various Reb RebA, RebD and RebM
  • the addition amount of various Reb was adjusted so that it might become the sweetness degree (Brick of sucrose conversion) equivalent to the drink sample to which only sucrose and fructose glucose were added as a sweetener.
  • HPLC HPLC conditions
  • HPLC apparatus Prominance series (manufactured by Shimadzu Corporation, system controller: SCL-10A, liquid pump: LC-20AD, online degassing apparatus: DGU-20A3, autosampler: SIL-20AC, column oven: CTO-20A, and (With UV / VIS detector: SPD-20A)
  • Mobile phase A 0.1% aqueous solution of formic acid
  • Mobile phase B acetonitrile
  • Flow rate 0.6 mL / min
  • Concentration gradient conditions 0.0 to 1.0 minutes (15% B) ⁇ 12.0 minutes (25% B) ⁇ 20.0 minutes (75% B) ⁇ 20.0 to 22.0 minutes (100% B) ), 3.0 minutes equilibration with initial mobile phase
  • Sample injection injection volume 5.0 ⁇ L Peak detection time: Although confirmation with a standard is required,
  • the relative value of the amount of hesperidin contained in the supernatant of various beverage samples was determined with the amount of hesperidin in the supernatant of the beverage sample containing only fruit juice as 100%. The result is shown in FIG.
  • sucrose and fructose was replaced with RebA, RebD, or RebM rather than the amount of hesperidin contained in the supernatant of a beverage sample to which only sucrose and fructose were added as sweeteners. It was revealed that the amount of hesperidin contained in the supernatant of the beverage sample was larger. If the amount of hesperidin in the supernatant is small, it is considered that the amount of hesperidin has been precipitated. Therefore, from this result, it was suggested that addition of RebA, RebD or RebM to a beverage suppresses precipitation of hesperidin. Among them, it was suggested that RebD and RebM have a higher precipitation suppressing effect than RebA.

Abstract

The purpose of the present invention is to provide a beverage in which the occurrence of precipitates has been inhibited. A beverage that satisfies conditions (A), (B) and (C): (A) contains RebD and/or RebM, (B) contains hesperidin, and (C) the degrees Brix (sucrose conversion) of the beverage is 3-15.

Description

ヘスペリジンの沈殿が抑制された飲料Beverages with reduced hesperidin precipitation
 本発明の実施の形態は、ヘスペリジンの沈殿が抑制された飲料に関する。 The embodiment of the present invention relates to a beverage in which precipitation of hesperidin is suppressed.
 オレンジ果汁を含有する飲料は、製造してから1ヶ月程度経過すると容器の底に沈殿が生じる傾向にある。沈殿物は主にオレンジ果汁由来のパルプが積層したものであるが、その上に白色の沈殿物がさらに蓄積される。この白色沈殿は、オレンジ果汁に含まれる溶解度の低いヘスペリジンの析出に起因することが知られている。白色沈殿の存在は見た目が悪く飲料の外観を損ない、結果的に飲料の商品価値を下げてしまうことになる。特に、近年普及しているペットボトル等の透明容器に充填された飲料においては、その外観の良否が商品価値に与える影響は大きい。 Beverages containing orange juice tend to precipitate at the bottom of the container after about one month has passed since manufacture. The precipitate is mainly a stack of pulp derived from orange juice, on which white precipitate is further accumulated. It is known that this white precipitate is caused by precipitation of hesperidin having low solubility contained in orange juice. The presence of the white precipitate looks bad and impairs the appearance of the beverage, resulting in a reduction in the commercial value of the beverage. In particular, in beverages filled in transparent containers such as PET bottles that have been widely used in recent years, the quality of the appearance has a great influence on the commercial value.
 本発明は、ヘスペリジンに起因する沈殿の発生が抑制された飲料を提供することを目的とする。 An object of the present invention is to provide a beverage in which the occurrence of precipitation due to hesperidin is suppressed.
 本発明者らは、上記課題を解決すべく鋭意検討した結果、驚くべきことに、レバウディオサイド(Rebaudioside、以下「Reb」とする。)D及び/又はRebMを添加すると、ヘスペリジンを含有する飲料においてヘスペリジンの沈殿化が抑制されることを見出した。かかる知見に基づいて、本発明者らは、本発明を完成させた。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have surprisingly added hesperidin when Rebaudioside (hereinafter referred to as “Reb”) D and / or RebM is added. It has been found that precipitation of hesperidin is suppressed in beverages. Based on this finding, the present inventors have completed the present invention.
 本発明の実施の形態は、これに限定されないが、以下の条件(A)、(B)及び(C):
(A)RebD及び/又はRebMを含有する、
(B)ヘスペリジンを含有する、並びに
(C)飲料のBrix(ショ糖換算)が3~15である、
を満たす飲料を提供する。
The embodiment of the present invention is not limited to this, but the following conditions (A), (B) and (C):
(A) containing RebD and / or RebM,
(B) contains hesperidin, and (C) the beverage has a Brix (in terms of sucrose) of 3 to 15.
Provide a beverage that meets the requirements.
 本発明によれば、ヘスペリジンの沈殿が抑制された飲料を提供することができる。ヘスペリジンを一成分として含む柑橘系果実の果汁を含有する飲料では、特にショ糖や果糖が当該飲料に添加された場合に沈殿形成が進行する傾向にある。本発明では、これらの糖類に代えてRebD及び/又はRebMが用いられ、しかもその添加量は非常に少なくすることができる。そのため、本発明は、ヘスペリジンの沈殿形成を効果的に抑制するだけでなく、ショ糖や果糖と同等の甘味を呈しながら、さらにカロリーの低い飲料の提供を実現することもできる。 According to the present invention, a beverage in which precipitation of hesperidin is suppressed can be provided. In beverages containing citrus fruit juice containing hesperidin as a component, precipitation tends to proceed especially when sucrose or fructose is added to the beverage. In the present invention, RebD and / or RebM are used in place of these saccharides, and the amount added can be very small. Therefore, the present invention not only effectively suppresses the formation of hesperidin precipitate, but also can provide a beverage having a lower calorie while exhibiting sweetness equivalent to that of sucrose and fructose.
図1は、RebA、RebD又はRebMの添加によるヘスペリジン沈殿の抑制効果を示すグラフである。FIG. 1 is a graph showing the effect of inhibiting hesperidin precipitation by the addition of RebA, RebD or RebM.
 以下、本発明の実施の形態に係る飲料を説明する。 Hereinafter, beverages according to embodiments of the present invention will be described.
 本発明の実施の形態に係る飲料は、以下の条件(A)、(B)及び(C):
(A)RebD及び/又はRebMを含有する、
(B)ヘスペリジンを含有する、並びに
(C)飲料のBrix(ショ糖換算)が3~15である、
を満たす飲料である。
The beverage according to the embodiment of the present invention has the following conditions (A), (B) and (C):
(A) containing RebD and / or RebM,
(B) contains hesperidin, and (C) the beverage has a Brix (in terms of sucrose) of 3 to 15.
It is a beverage that meets the requirements.
 本発明の実施の形態に係る飲料には、RebD及び/又はRebMが含まれる。Reb(レバウディオサイド(Rebaudioside))は、ステビア抽出物に含まれる甘味成分として知られている。ステビア抽出物は、ステビア乾燥葉から抽出、精製されたものである。ステビアは南米パラグアイを原産地とする菊科多年生植物で、学名をステビア・レバウディアナ・ベルトニー(Stevia Rebaudiana Bertoni)という。ステビアは砂糖の約300倍以上の甘味を持つ成分を含むので、この甘味成分を抽出して天然甘味料として用いる為に栽培されている。Rebとしては、RebA、RebB、RebC、RebD、RebEが知られている。更に、最近では特表2012-504552に記載のRebM等、様々な配糖体の存在が報告されている。様々なRebの中で、RebAは、高甘味度と良質甘味を有する甘味料として評価されており、広く用いられている。本発明の実施の形態では、ステビア抽出物として特にRebD及びRebMに着目する。RebD及びRebMは、市場から入手することができるし、有機化学的手法により合成することもできる。或いは、ステビア抽出物を出発原料として、RebD及びRebMを分離、精製することもできる。例えば、RebDはUS8414949号に記載された方法に従って精製することができ、そしてRebMはFoods 2014, 3(1), 162-175; doi:10.3390/foods3010162に記載された方法に従って精製することができる。RebD及びRebMは、いずれの方法によって分析してもよいが、例えば、特表2012-504552号に記載の条件に設定した高速液体クロマトグラフィー分析計(HPLC)により分析することができる。本明細書では、特に記載がなければ、当該方法によりRebD及びRebMを分析するものとする。 The beverage according to the embodiment of the present invention includes RebD and / or RebM. Reb (Rebaudioside) is known as a sweetening component contained in stevia extract. Stevia extract is extracted and purified from dried Stevia leaves. Stevia is a perennial plant of Chrysanthemum that originates in Paraguay, South America, and its scientific name is Stevia Rebaudiana Bertoni. Stevia contains ingredients that are about 300 times more sweet than sugar and is cultivated to extract these sweet ingredients and use them as natural sweeteners. As Reb, RebA, RebB, RebC, RebD, and RebE are known. Furthermore, recently, the existence of various glycosides such as RebM described in JP 2012-504552 has been reported. Among various types of Reb, RebA is evaluated as a sweetener having high sweetness and good quality sweetness, and is widely used. In the embodiment of the present invention, attention is paid particularly to RebD and RebM as stevia extracts. RebD and RebM can be obtained from the market or can be synthesized by an organic chemical method. Alternatively, RebD and RebM can be separated and purified using stevia extract as a starting material. For example, RebD can be purified according to the method described in US8414949, and RebM can be purified according to the method described in Foods 2014, 3 (1), 162-175; doi: 10.3390 / foods 3010262. it can. RebD and RebM may be analyzed by any method. For example, RebD and RebM can be analyzed by a high performance liquid chromatography analyzer (HPLC) set to the conditions described in JP-T-2012-504552. In this specification, unless otherwise specified, RebD and RebM are analyzed by the method.
 また、本発明の実施の形態に係る飲料にはRebAが含まれていてもよい。RebAは、RebD及びRebMと同様に、市場から入手することができるし、有機化学的手法により合成することもできる。或いは、ステビア抽出物を出発原料として、RebAを分離、精製することもできる。例えば、RebAは特表2009-517043号に記載された方法に従って精製することができる。RebAは、いずれの方法によって分析してもよく、上述したようにRebD及びRebMと同様の方法で分析することができる。 Further, RebA may be included in the beverage according to the embodiment of the present invention. Like RebD and RebM, RebA can be obtained from the market or can be synthesized by an organic chemical method. Alternatively, RebA can be separated and purified using stevia extract as a starting material. For example, RebA can be purified according to the method described in JP-T 2009-517043. RebA may be analyzed by any method, and can be analyzed by the same method as RebD and RebM as described above.
 本発明の実施の形態に係る飲料における各種Rebの含有量は、本発明の効果が得られる限り特に限定されない。RebDの含有量は、例えば、飲料中、100~500ppmとすることができる。RebDの含有量は、好ましくは120ppm以上、140ppm以上、150ppm以上、180ppm以上、又は200ppm以上であり、また、好ましくは480ppm以下、460ppm以下、450ppm以下、430ppm以下、又は400ppm以下である。また、RebMの含有量は、例えば、飲料中、100~500ppmとすることができる。RebMの含有量は、好ましくは120ppm以上、140ppm以上、150ppm以上、180ppm以上、又は200ppm以上であり、また、好ましくは480ppm以下、460ppm以下、450ppm以下、430ppm以下、又は400ppm以下である。RebAが用いられる場合、RebAの含有量は、例えば、飲料中、100~500ppmとすることができる。RebAの含有量は、好ましくは120ppm以上、140ppm以上、150ppm以上、180ppm以上、又は200ppm以上であり、また、好ましくは480ppm以下、460ppm以下、450ppm以下、430ppm以下、又は400ppm以下である。なお、本明細書において用いる「ppm」は、特に断りがない限り、重量/容量(w/v)のppmを意味する。 The content of various Rebs in the beverage according to the embodiment of the present invention is not particularly limited as long as the effect of the present invention is obtained. The content of RebD can be, for example, 100 to 500 ppm in the beverage. The content of RebD is preferably 120 ppm or more, 140 ppm or more, 150 ppm or more, 180 ppm or more, or 200 ppm or more, and preferably 480 ppm or less, 460 ppm or less, 450 ppm or less, 430 ppm or less, or 400 ppm or less. The content of RebM can be, for example, 100 to 500 ppm in the beverage. The content of RebM is preferably 120 ppm or more, 140 ppm or more, 150 ppm or more, 180 ppm or more, or 200 ppm or more, and preferably 480 ppm or less, 460 ppm or less, 450 ppm or less, 430 ppm or less, or 400 ppm or less. When RebA is used, the content of RebA can be, for example, 100 to 500 ppm in the beverage. The content of RebA is preferably 120 ppm or more, 140 ppm or more, 150 ppm or more, 180 ppm or more, or 200 ppm or more, and preferably 480 ppm or less, 460 ppm or less, 450 ppm or less, 430 ppm or less, or 400 ppm or less. In addition, “ppm” used in this specification means ppm of weight / volume (w / v) unless otherwise specified.
 本発明の実施の形態に係る飲料において、RebD及びRebMの両方ともが用いられる場合、飲料におけるその合計含有量は、必要とされる範囲で設定することができ、香味上問題とならない範囲で設定することができる。例えば、限定されないが、RebD及びRebMの2種が用いられる場合、飲料中のその合計含有量は100~500ppm、好ましくは150~450ppm、より好ましくは200~400ppm、さらに好ましくは250~350ppmとすることができる。 In the beverage according to the embodiment of the present invention, when both RebD and RebM are used, the total content in the beverage can be set within a required range, and set within a range that does not cause a problem in flavor. can do. For example, although not limited, when two types of RebD and RebM are used, the total content in the beverage is 100 to 500 ppm, preferably 150 to 450 ppm, more preferably 200 to 400 ppm, and still more preferably 250 to 350 ppm. be able to.
 また、RebAが用いられる場合については、飲料におけるRebA、RebD、及びRebMの2種以上の合計含有量は、上記と同様に、必要とされる範囲で設定することができ、香味上問題とならない範囲で設定することができる。例えば、限定されないが、RebA、RebD、及びRebMのうちいずれか2種が用いられる場合、飲料中のその合計含有量は100~500ppm、好ましくは150~450ppm、より好ましくは200~400ppm、さらに好ましくは250~350ppmとすることができる。また、同様に限定されるわけではないが、RebA、RebD、及びRebMの全てが用いられる場合、飲料中のその合計含有量は100~500ppm、好ましくは150~450ppm、より好ましくは200~400ppm、さらに好ましくは250~350ppmとすることができる。 In addition, when RebA is used, the total content of two or more of RebA, RebD, and RebM in the beverage can be set within the required range in the same manner as described above, and there is no problem in flavor. Can be set by range. For example, although not limited, when any two of RebA, RebD, and RebM are used, the total content in the beverage is 100 to 500 ppm, preferably 150 to 450 ppm, more preferably 200 to 400 ppm, and still more preferably. Can be 250-350 ppm. Further, although not limited in the same way, when all of RebA, RebD, and RebM are used, the total content in the beverage is 100 to 500 ppm, preferably 150 to 450 ppm, more preferably 200 to 400 ppm, More preferably, it can be 250 to 350 ppm.
 本発明の実施の形態に係る飲料において、RebD及びRebMが用いられる場合、特に限定されないが、その質量比(RebDの含有量に対するRebMの含有量の比率(RebM/RebD))は、例えば0.01~10であり、好ましくは0.1~1である。 When RebD and RebM are used in the beverage according to the embodiment of the present invention, the mass ratio (the ratio of the RebM content to the RebD content (RebM / RebD)) is, for example, 0. 01 to 10, preferably 0.1 to 1.
 本発明の実施の形態に係る飲料において、RebA及びRebDが用いられる場合、特に限定されないが、その質量比(RebAの含有量に対するRebDの含有量の比率(RebD/RebA))は、例えば0.01~40であり、好ましくは0.2~20である。 When RebA and RebD are used in the beverage according to the embodiment of the present invention, the mass ratio (the ratio of the RebD content to the RebA content (RebD / RebA)) is, for example, 0. It is 01 to 40, and preferably 0.2 to 20.
 本発明の実施の形態に係る飲料において、RebA及びRebMが用いられる場合、特に限定されないが、その質量比(RebAの含有量に対するRebMの含有量の比率(RebM/RebA))は、例えば0.01~10であり、好ましくは0.05~5である。 When RebA and RebM are used in the beverage according to the embodiment of the present invention, the mass ratio (the ratio of the RebM content to the RebA content (RebM / RebA)) is, for example, 0. 01 to 10, preferably 0.05 to 5.
 本発明の実施の形態に係る飲料では、特に制限されないが、適度な甘味を感じることができるようその甘味度を調整することができる。その甘味度として、例えば、本発明の実施の形態に係る飲料のショ糖換算のBrixは3~15であり、好ましくは4~12、より好ましくは8~12、さらに好ましくは8~11である。当該Brixが3未満の場合、飲料の呈味としてステビア抽出物に由来する甘味を十分に感じられない傾向にある。一方、当該Brixが15を超える場合は、甘味が強くなりすぎて香味が悪くなる傾向にある。 The beverage according to the embodiment of the present invention is not particularly limited, but the sweetness level can be adjusted so that an appropriate sweetness can be felt. As the sweetness level, for example, the sucrose equivalent Brix of the beverage according to the embodiment of the present invention is 3 to 15, preferably 4 to 12, more preferably 8 to 12, and still more preferably 8 to 11. . When the Brix is less than 3, the sweetness derived from the stevia extract tends not to be sufficiently felt as a beverage taste. On the other hand, when the Brix exceeds 15, the sweetness becomes too strong and the flavor tends to deteriorate.
 ここで、ショ糖換算のBrixとは、ショ糖に対するRebの甘味度と、Rebの含有量から計算することができる。ショ糖に対して、RebAは300倍、RebDは285倍、RebMは285倍の甘味を有する。従って、ショ糖換算のBrixは、RebAの含有量を300倍した数値、RebDの含有量を285倍した数値、及びRebMの含有量を285倍した数値から算出することができる。なお、ショ糖換算のBrixが1に相当する量は、RebAについては33.3ppm、RebDについては35.1ppm、及びRebMについては35.1ppmである。 Here, Brix in terms of sucrose can be calculated from the sweetness of Reb with respect to sucrose and the content of Reb. RebA has a sweetness 300 times, RebD has a sweetness of 285 times, and RebM has a sweetness of 285 times that of sucrose. Therefore, Brix in terms of sucrose can be calculated from a value obtained by multiplying the RebA content by 300 times, a value obtained by multiplying the RebD content by 285 times, and a value obtained by multiplying the RebM content by 285 times. In addition, the amount of Brix equivalent to 1 in terms of sucrose is 33.3 ppm for RebA, 35.1 ppm for RebD, and 35.1 ppm for RebM.
 本発明の実施の形態に係る飲料のショ糖換算のBrixは、上記の通りRebD及びRebM(場合により、RebAを含む)の含有量から計算することができるが、RebA、RebD及びRebM以外の甘味料を用いた場合は、当該Brixは全甘味料の甘味度の合計値として表される。このとき、本発明の飲料のBrixは、例えば、市販のBrix計により測定することができる。RebA、RebD及びRebM以外の甘味料としては、特に限定されないが、例えば、ショ糖、果糖等の糖類、並びにアスパルテーム、スクラロース、及びアセスルファムK等の高甘味度甘味料等が挙げられる。ショ糖が用いられる場合、その飲料中の含有量は、例えば3~15重量%、好ましくは4~12重量%、より好ましくは8~11重量%であるが、特にこれに限定されない。また、果糖が用いられる場合、その飲料中の含有量は、例えば3~15重量%、好ましくは4~12重量%、より好ましくは8~11重量%であるが、特にこれに限定されない。ショ糖、果糖等の甘味料は市販品を用いることができ、その形態は粉末であっても液状(液糖)であってもよく、特に限定されない。なお、本明細書において用いる「重量%」は、特に断りがない限り、重量/容量(w/v)の重量%を意味する。 The sucrose equivalent Brix of the beverage according to the embodiment of the present invention can be calculated from the contents of RebD and RebM (including RebA in some cases) as described above, but sweetness other than RebA, RebD and RebM When a scent is used, the Brix is expressed as a sum of sweetness levels of all sweeteners. At this time, Brix of the beverage of the present invention can be measured by, for example, a commercially available Brix meter. Sweeteners other than RebA, RebD, and RebM are not particularly limited, and examples thereof include saccharides such as sucrose and fructose, and high-intensity sweeteners such as aspartame, sucralose, and acesulfame K. When sucrose is used, its content in the beverage is, for example, 3 to 15% by weight, preferably 4 to 12% by weight, more preferably 8 to 11% by weight, but is not particularly limited thereto. When fructose is used, the content in the beverage is, for example, 3 to 15% by weight, preferably 4 to 12% by weight, more preferably 8 to 11% by weight, but is not particularly limited thereto. As sweeteners such as sucrose and fructose, commercially available products can be used, and the form thereof may be powder or liquid (liquid sugar), and is not particularly limited. “Wt%” used in this specification means weight% of weight / volume (w / v) unless otherwise specified.
 ショ糖、果糖等の甘味料(特に糖類)の定量は、当業者によく知られた方法により行うことができる。例えば、以下の条件に設定した高速液体クロマトグラフィー(HPLC)によって行うことができる:
使用機器:HP社 HP1100システム
使用カラム:LiChrospher100 NH2(5μm)(4mm×250mm)移動相:アセトニトリル:水=75:25
流速:1.0mL/min
カラム温度:40℃
注入量:10μL
検出器:糖度示差屈折計(Shodex RI-71)。
Quantification of sweeteners (especially sugars) such as sucrose and fructose can be carried out by methods well known to those skilled in the art. For example, it can be performed by high performance liquid chromatography (HPLC) set to the following conditions:
Equipment used: HP company HP1100 system use column: LiChrosphere100 NH2 (5 μm) (4 mm × 250 mm) Mobile phase: acetonitrile: water = 75: 25
Flow rate: 1.0 mL / min
Column temperature: 40 ° C
Injection volume: 10 μL
Detector: Sugar content differential refractometer (Shodex RI-71).
 本発明の実施の形態に係る飲料は、ヘスペリジンをさらに含有する。ヘスペリジン(C283415)は、フラボノイド骨格を有する化合物であり、柑橘類果実によく見られる成分である。ヘスペリジンは、レモン、オレンジ、ミカン、ユズ、ライム、ポンカン、ハッサク、キンカン、シークワーサー等で検出される成分であり、若干の苦味を有する。 The beverage according to the embodiment of the present invention further contains hesperidin. Hesperidin (C 28 H 34 O 15 ) is a compound having a flavonoid skeleton, and is a component often found in citrus fruits. Hesperidin is a component detected in lemon, orange, mandarin orange, yuzu, lime, ponkan, hassaku, kumquat, seeker, and the like, and has a slight bitter taste.
 本発明の実施の形態に係る飲料におけるヘスペリジンの含有量は、特に限定されないが、例えば1~250ppmである。本発明の飲料におけるヘスペリジンの含有量は、好ましくは10ppm以上、50ppm以上、100ppm以上、又は130ppm以上であり、また、好ましくは230ppm以下、200ppm以下、又は180ppm以下である。 The content of hesperidin in the beverage according to the embodiment of the present invention is not particularly limited, and is, for example, 1 to 250 ppm. The content of hesperidin in the beverage of the present invention is preferably 10 ppm or more, 50 ppm or more, 100 ppm or more, or 130 ppm or more, and preferably 230 ppm or less, 200 ppm or less, or 180 ppm or less.
 本発明の実施の形態に係る飲料において、飲料中のヘスペリジンの含有量の調整は、特に制限されないが、当該成分を含有する天然由来の材料の量を適宜調整することにより行うことができる。自然な果実らしさの香味付与の観点から、各種果実の果汁の1種または2種以上を用いることにより、ヘスペリジンの含有量を調整することが好ましい。柑橘類果実におけるヘスペリジンの量については、例えば、近畿中国四国農業研究センター研究報告 第5号、2005、野方洋一、「カンキツ果実の機能性成分の検索とその有効利用に関する研究」などで報告されており、そのような資料を参考にして、用いる果汁を選択、検討することができる。柑橘類果実の果汁としては、特にオレンジ果汁が好ましい。 In the beverage according to the embodiment of the present invention, the adjustment of the content of hesperidin in the beverage is not particularly limited, but can be performed by appropriately adjusting the amount of the naturally-derived material containing the component. From the viewpoint of imparting a natural fruity flavor, it is preferable to adjust the content of hesperidin by using one or more fruit juices of various fruits. The amount of hesperidin in citrus fruits has been reported in, for example, Kinki Chugoku Shikoku Agricultural Research Center Research Report No. 5, 2005, Yoichi Nogata, “Research on Functional Components of Citrus Fruits and Their Effective Use” The juice to be used can be selected and examined with reference to such materials. As the citrus fruit juice, orange juice is particularly preferable.
 本発明の実施の形態に係る飲料中のヘスペリジンの含有量は、高速液体クロマトグラフィー質量分析法(LC-MS)等公知の手法を用いて測定することができる。例えば、以下の条件で測定することができる。 The content of hesperidin in the beverage according to the embodiment of the present invention can be measured using a known method such as high performance liquid chromatography mass spectrometry (LC-MS). For example, it can be measured under the following conditions.
 <ヘスペリジンの分析>
 LC-MSを用いたヘスペリジン量の分析方法を以下に示す。
<Analysis of hesperidin>
A method for analyzing the amount of hesperidin using LC-MS is shown below.
 (1)サンプルの調製
 炭酸ガスを含む飲料は、常法にて炭酸ガスを除く。まず、遠沈管(A)に溶液10gを秤量する。試料のBrixが20゜Bx以上の場合は5g、40゜Bx以上の場合は2gを秤量し、液体クロマトグラフィー用蒸留水で10mLに希釈する。液体クロマトグラフィー用エタノール20mLを加え、ボルテックスミキサーにて1分以上激しく混和する。粘性が高く混ざらない場合は、必要に応じて手などで激しく振り混ぜる。これを遠心器に供し(3000xg、30分、20℃)、上清を別の遠沈管(B)に移す。沈殿物に液体クロマトグラフィー用エタノール20mLを加え、固形分を薬匙などで十分に崩した後、ボルテックスミキサーにて1分以上激しく混和する。遠心器で遠心(3000xg、30分、20℃)し、上清を遠沈管(B)に加える。遠沈管(B)に集めた上清は、さらに遠心(3000xg、30分、20℃)し、得られた上清を50mLのメスフラスコに移し、エタノールでメスアップする。よく混和した上清液を、予めエタノールで洗浄したPTFE製フィルター(東洋濾紙社製、ADVANTEC DISMIC-25HP 25HP020AN,孔径0.20μm、直径25mm)で濾過し、分析試料とする。
(1) Preparation of sample Beverages containing carbon dioxide gas remove carbon dioxide by a conventional method. First, 10 g of the solution is weighed in the centrifuge tube (A). When the Brix of the sample is 20 ° Bx or more, weigh 5 g, and when the Brix is 40 ° Bx or more, weigh 2 g and dilute to 10 mL with distilled water for liquid chromatography. Add 20 mL of ethanol for liquid chromatography and mix vigorously with a vortex mixer for 1 minute or longer. If it is too viscous to mix, shake it vigorously with your hands if necessary. This is subjected to a centrifuge (3000 × g, 30 minutes, 20 ° C.), and the supernatant is transferred to another centrifuge tube (B). Add 20 mL of ethanol for liquid chromatography to the precipitate and thoroughly disintegrate the solid content with a medicine basket. Centrifuge (3000 × g, 30 minutes, 20 ° C.) and add supernatant to centrifuge tube (B). The supernatant collected in the centrifuge tube (B) is further centrifuged (3000 × g, 30 minutes, 20 ° C.), and the resulting supernatant is transferred to a 50 mL volumetric flask and made up with ethanol. The well-mixed supernatant is filtered through a PTFE filter (Toyo Roshi Kaisha, ADVANTEC DISMIC-25HP 25HP020AN, pore size 0.20 μm, diameter 25 mm) previously washed with ethanol to obtain an analytical sample.
 (2)HPLC分析条件
 HPLC装置:Prominanceシリーズ(島津製作所社製、システムコントローラー:SCL-10A、送液ポンプ:LC-20AD、オンライン脱気装置:DGU-20A3、オートサンプラー:SIL-20AC、カラムオーブン:CTO-20A、及びUV/VIS検出器:SPD-20Aを有する)
 カラム:CAPCELL CORE AQ(粒径2.7μm、内径3.0mm x 150mm、資生堂社製)
 移動相A:ギ酸0.1%水溶液
 移動相B:アセトニトリル
 流量:0.6mL/min
 濃度勾配条件:0.0~1.0分(15%B)→12.0分(25%B)→20.0分(75%B)→20.0~22.0分(100%B)、初期移動相による平衡化3.0分
 カラム温度:40℃
 試料注入:注入量5.0μL
 ピーク検出時間:標品による確認を要するが、概ね2.51分である。
(2) HPLC analysis conditions HPLC apparatus: Prominance series (manufactured by Shimadzu Corporation, system controller: SCL-10A, liquid pump: LC-20AD, online degassing apparatus: DGU-20A3, autosampler: SIL-20AC, column oven : CTO-20A, and UV / VIS detector: SPD-20A)
Column: CAPCELL CORE AQ (particle size 2.7 μm, inner diameter 3.0 mm × 150 mm, manufactured by Shiseido Co., Ltd.)
Mobile phase A: 0.1% aqueous solution of formic acid Mobile phase B: acetonitrile Flow rate: 0.6 mL / min
Concentration gradient conditions: 0.0 to 1.0 minutes (15% B) → 12.0 minutes (25% B) → 20.0 minutes (75% B) → 20.0 to 22.0 minutes (100% B) ), 3.0 minutes equilibration with initial mobile phase Column temperature: 40 ° C
Sample injection: injection volume 5.0 μL
Peak detection time: Although confirmation with a standard is required, it is approximately 2.51 minutes.
 (3)定量方法
 濃度の異なる標品溶液3点以上を供し、得られたピーク面積による絶対検量線法で定量する。
(3) Quantification method Three or more sample solutions having different concentrations are provided, and quantified by the absolute calibration curve method using the obtained peak areas.
 本発明の実施の形態に係る飲料において、RebDが用いられる場合、ヘスペリジンの含有量に対するRebDの含有量の比率(RebD/ヘスペリジン))は、例えば0.01~10、好ましくは0.1~5、より好ましくは0.5~2である。 In the beverage according to the embodiment of the present invention, when RebD is used, the ratio of the content of RebD to the content of hesperidin (RebD / hesperidin)) is, for example, 0.01 to 10, preferably 0.1 to 5 More preferably, it is 0.5-2.
 本発明の実施の形態に係る飲料において、RebMが用いられる場合、ヘスペリジンの含有量に対するRebMの含有量の比率(RebM/ヘスペリジン))は、例えば0.01~10、好ましくは0.1~5、より好ましくは0.5~2である。 In the beverage according to the embodiment of the present invention, when RebM is used, the ratio of the content of RebM to the content of hesperidin (RebM / hesperidin)) is, for example, 0.01 to 10, preferably 0.1 to 5 More preferably, it is 0.5-2.
 本発明の実施の形態に係る飲料において、RebAが用いられる場合、ヘスペリジンの含有量に対するRebAの含有量の比率(RebA/ヘスペリジン))は、例えば0.01~10、好ましくは0.1~5、より好ましくは0.5~2である。 In the beverage according to the embodiment of the present invention, when RebA is used, the ratio of the content of RebA to the content of hesperidin (RebA / hesperidin)) is, for example, 0.01 to 10, preferably 0.1 to 5 More preferably, it is 0.5-2.
 本発明の実施の形態に係る飲料は、果汁を含んでいてもよい。果汁の種類としては、特に限定されないが、例えば、オレンジ果汁、グレープフルーツ果汁、ミカン果汁、マンダリン果汁等の柑橘類果実の果汁、リンゴ果汁、ブドウ果汁、モモ果汁、いちご果汁、バナナ果汁、さくらんぼ果汁、メロン果汁、スイカ果汁、マンゴー果汁、パパイヤ果汁、キウイ果汁、日本ナシ果汁、西洋ナシ果汁、カキ果汁、ウメ果汁、マスカット果汁、パイナップル果汁、パッションフルーツ果汁、グアバ果汁、アンズ果汁、スモモ果汁、クランベリー果汁、ザクロ果汁などを挙げることができる。本発明の実施の形態に係る飲料は、1種または2種以上の果汁を含有することができる。本発明では、特に限定されるわけではないが、果汁の中では柑橘類果実の果汁が好ましく、特にオレンジ果汁が好ましい。また、本発明において果汁は、ストレート果汁、濃縮果汁等、製造方法によらず使用することができる。ハンドリングの良さを考慮すると濃縮還元果汁は好ましい。 The beverage according to the embodiment of the present invention may contain fruit juice. The type of fruit juice is not particularly limited. For example, fruit juice of citrus fruits such as orange juice, grapefruit juice, mandarin juice, mandarin juice, apple juice, grape juice, peach juice, strawberry juice, banana juice, cherry juice, melon Fruit juice, watermelon juice, mango juice, papaya juice, kiwi juice, Japanese pear juice, pear juice, oyster juice, ume juice, muscat juice, pineapple juice, passion fruit juice, guava juice, apricot juice, plum juice, cranberry juice, Pomegranate juice can be mentioned. The drink which concerns on embodiment of this invention can contain 1 type, or 2 or more types of fruit juice. In the present invention, although not particularly limited, citrus fruit juice is preferable, and orange juice is particularly preferable. Moreover, in this invention, fruit juice can be used regardless of manufacturing methods, such as straight fruit juice and concentrated fruit juice. In view of good handling, concentrated reduced fruit juice is preferable.
 本発明の実施の形態に係る飲料において果汁を用いる場合、その果汁率は1~100%とすることができる。特に限定されないが、当該果汁率は好ましくは1~100%、より好ましくは10~100%である。ヘスペリジンの沈殿化抑制効果を発揮する上では、果汁率は高い方が好ましいともいえる。ここで「果汁率」とは、果汁を搾汁して得られるストレート果汁を100%としたときの相対濃度をいう。例えば、JAS規格(果実飲料の日本農林規格)に示される各種果実のストレート果汁の糖用屈折計示度の基準又は酸度の基準(下記)に基づいて、換算できる:
 (糖用屈折計示度の基準(゜Bx))
・オレンジ、ポンカン 11
・はっさく、いよかん 10
・うんしゅうみかん、グレープフルーツ、なつみかん 9
・シークワーサー 8
 (酸度の基準(クエン酸換算)(%))
・レモン 4.5
・ライム 6
・カボス 3.5。
When fruit juice is used in the beverage according to the embodiment of the present invention, the fruit juice ratio can be 1 to 100%. Although not particularly limited, the fruit juice ratio is preferably 1 to 100%, more preferably 10 to 100%. It can be said that a higher fruit juice ratio is preferable in order to exert the effect of inhibiting the precipitation of hesperidin. Here, the “fruit juice ratio” refers to the relative concentration when straight juice obtained by squeezing fruit juice is taken as 100%. For example, it can be converted based on the standard of refractometer reading for sugar or the standard of acidity (below) of straight fruit juice of various fruits shown in the JAS standard (Japanese agricultural and forestry standard for fruit drinks):
(Standard of refractometer reading for sugar (° Bx))
・ Orange, Ponkan 11
・ Hassaku, Yokan 10
・ Yunshu oranges, grapefruits, summer oranges 9
・ Seek Warser 8
(Standard for acidity (citric acid equivalent) (%))
・ Lemon 4.5
・ Lime 6
・ Kabos 3.5.
 その他、ユズ及びスダチは、それぞれ、4.3及び6.6を酸度の基準(クエン酸換算)(%)として用いてもよい。 In addition, Yuzu and Sudachi may use 4.3 and 6.6, respectively, as the acidity standard (citric acid equivalent) (%).
 果汁率の計算方法は、例えば、JAS規格においてライム果汁の酸度の基準はクエン酸に換算して6%であるから、酸度30%の濃縮ライム果汁を飲料中に6重量%配合した場合、果汁率は30%となる。上記に記載のない果実についても同様に、ストレート果汁を100%としたときの相対濃度に換算することにより、果汁率を計算することができる。例えば、2倍濃縮果汁を飲料中に5重量%用いた場合には、飲料の果汁率は10%となる。 The method for calculating the fruit juice rate is, for example, that the standard of acidity of lime juice in JAS standards is 6% in terms of citric acid. Therefore, when 6% by weight of concentrated lime juice with an acidity of 30% is blended in the beverage, fruit juice The rate is 30%. Similarly, the fruit juice ratio can be calculated by converting the fruit juice not described above into a relative concentration when straight fruit juice is 100%. For example, when 5% by weight of double concentrated fruit juice is used in a beverage, the juice rate of the beverage is 10%.
 本発明の実施の形態に係る飲料において複数種類の果汁が用いられている場合には、果汁率は、上記に基づいてすべての果汁の果汁率を計算し、合計した値となる。なお、この計算により得られる果汁率は、通常、飲料の容器に示される果汁の割合(「果汁○%」の表示の数値)に相当する。 When a plurality of types of fruit juices are used in the beverage according to the embodiment of the present invention, the fruit juice ratio is a sum of the fruit juice ratios of all the fruit juices calculated based on the above. The fruit juice ratio obtained by this calculation usually corresponds to the ratio of the fruit juice shown in the beverage container (the numerical value indicated as “fruit juice ○%”).
 本発明の実施の形態に係る飲料は、本発明の効果を妨げない限り、カテキン等のポリフェノール類、植物の抽出物、カフェイン、シンナムアルデヒド、カラメル色素、及び甘味料(砂糖、異性化液糖、等の糖類、並びにアスパルテーム、スクラロース、及びアセスルファムK等の高甘味度甘味料)、香料、酸味料(クエン酸、酒石酸、リンゴ酸、リン酸、乳酸)、着色料、果汁、果汁ピューレ、乳、乳製品、その他のフレーバー、及び強化剤(ビタミン類、カルシウム、ミネラル類、アミノ酸類)等の、飲食品に用いることのできる成分を更に含んでもよい。これらの成分は単独又は複数を組み合わせて飲料に配合してもよい。 Unless the beverage according to the embodiment of the present invention interferes with the effects of the present invention, polyphenols such as catechins, plant extracts, caffeine, cinnamaldehyde, caramel color, and sweeteners (sugar, isomerized liquid sugar) , Sugars such as aspartame, sucralose, and acesulfame K), flavorings, acidulants (citric acid, tartaric acid, malic acid, phosphoric acid, lactic acid), colorants, fruit juice, fruit puree, milk , Dairy products, other flavors, and fortifiers (vitamins, calcium, minerals, amino acids), and the like may be further included. You may mix | blend these components with a drink individually or in combination.
 本発明の実施の形態に係る飲料において、飲料の種類は特に限定されず、炭酸飲料、非炭酸飲料、アルコール飲料、非アルコール飲料、栄養飲料、機能性飲料などいずれであってもよい。 In the beverage according to the embodiment of the present invention, the type of beverage is not particularly limited and may be any of carbonated beverage, non-carbonated beverage, alcoholic beverage, non-alcoholic beverage, nutritional beverage, functional beverage, and the like.
 本発明の実施の形態に係る飲料を炭酸飲料(即ち、発泡性)とする場合、その方法は特に制限されず、発酵により炭酸ガスを飲料中に発生させてもよく、或いは人為的に炭酸ガスを飲料に注入してもよい。炭酸ガスを注入する場合、そのガス圧は、温度が20℃において、例えば1.0~3.0kgf/cm、好ましくは1.2~2.0kgf/cm、より好ましくは1.5~1.8kgf/cmとすることができる。炭酸ガスの添加は、当業者に公知の方法を用いて行うことができる。飲料中の炭酸ガス圧は、例えば、京都電子工業製ガスボリューム測定装置GVA-500Aを用いて測定することができる。 When the beverage according to the embodiment of the present invention is a carbonated beverage (that is, effervescent), the method is not particularly limited, and carbon dioxide may be generated in the beverage by fermentation, or artificially carbon dioxide. May be injected into the beverage. When injecting carbon dioxide, the gas pressure, the temperature is 20 ° C., for example, 1.0 ~ 3.0 kgf / cm 2, preferably 1.2 ~ 2.0 kgf / cm 2, more preferably 1.5 ~ It can be 1.8 kgf / cm 2 . Carbon dioxide gas can be added using methods known to those skilled in the art. The carbon dioxide pressure in the beverage can be measured, for example, using a gas volume measuring device GVA-500A manufactured by Kyoto Electronics Industry.
 本発明の実施の形態に係る飲料は、特に限定されないが、容器詰めとすることができる。容器は、いずれの形態・材質の容器を使用することができ、例えば、ビン、缶、樽、又はペットボトル等の容器であってもよい。また、飲料の容器への充填方法も特に制限されない。 The beverage according to the embodiment of the present invention is not particularly limited, but can be packed in a container. As the container, a container of any form / material can be used. For example, a container such as a bottle, a can, a barrel, or a plastic bottle may be used. Also, the method for filling the beverage container is not particularly limited.
 本発明の別の側面によれば、ヘスペリジンの沈殿を抑制する方法が提供される。 According to another aspect of the present invention, a method for suppressing precipitation of hesperidin is provided.
 本発明の実施の形態に係る方法は、飲料におけるヘスペリジンの沈殿を抑制する方法であって、
以下の工程(A)、(B)及び(C):
(A)RebD及び/又はRebMを配合する工程、
(B)ヘスペリジンを配合する工程、並びに
(C)飲料のBrix(ショ糖換算)を3~15に調整する工程、
を含む、上記方法である。
A method according to an embodiment of the present invention is a method for suppressing precipitation of hesperidin in a beverage,
The following steps (A), (B) and (C):
(A) A step of blending RebD and / or RebM,
(B) a step of blending hesperidin, and (C) a step of adjusting Brix (converted to sucrose) of the beverage to 3 to 15,
Is the above method.
 本発明の方法において、飲料中の成分の種類やその含有量等の各種要素については、本発明の飲料に関して上記した通りであるか、それらから自明である。本発明の方法は、上記に示した成分及び材料を配合する工程やそれらの含有量を調整する工程も含むことができる。なお、各種工程は同時に行ってもよいし、別々に行ってもよいし、工程の順番を入れ替えてもよい。各種工程のタイミングは、状況に応じて適宜調整することができる。 In the method of the present invention, various elements such as the types of ingredients in the beverage and their contents are as described above for the beverage of the present invention, or are obvious from them. The method of this invention can also include the process of mix | blending the component and material shown above, and the process of adjusting those content. In addition, various processes may be performed simultaneously, may be performed separately, and the order of processes may be changed. The timing of various processes can be adjusted as appropriate according to the situation.
 以下、実験例及び実施例を示して本発明の詳細を具体的に説明する。以下の説明は、本発明の理解を容易にすることをのみを目的とするものであり、本発明の範囲を限定することを意図するものではない。 Hereinafter, the details of the present invention will be specifically described with reference to experimental examples and examples. The following description is intended only to facilitate understanding of the invention and is not intended to limit the scope of the invention.
 ヘスペリジンによる飲料中の沈殿形成の程度を調べるため、以下の通り飲料サンプルを調製した。 In order to examine the degree of precipitate formation in the beverage by hesperidin, a beverage sample was prepared as follows.
 濃縮オレンジ果汁を果汁率が100%となるよう純水に添加して、果汁のみが含まれる飲料サンプルを調製した。このとき、飲料サンプルにおけるヘスペリジンの含有量は140ppmであった。また、同様に濃縮オレンジ果汁を添加した果汁率100%の飲料サンプルについて、下表に示した含有量となるようにショ糖型液糖(大日本明治製糖株式会社製、ES67B)、果糖ブドウ糖液糖(日本コーンスターチ株式会社製、F-55)、及び各種Reb(RebA、RebD及びRebM)がさらに添加されたものをそれぞれ調製した。なお、各種Rebの添加量は、甘味料としてショ糖及び果糖ブドウ糖のみが添加された飲料サンプルと同等の甘味度(ショ糖換算のBrix)となるよう調整した。 Concentrated orange fruit juice was added to pure water so that the fruit juice ratio would be 100% to prepare a beverage sample containing only fruit juice. At this time, the content of hesperidin in the beverage sample was 140 ppm. Similarly, for a beverage sample having a fruit juice ratio of 100% to which concentrated orange juice is added, sucrose type liquid sugar (ES67B, manufactured by Dainippon Meiji Sugar Co., Ltd.), fructose glucose liquid so as to have the content shown in the table below. Sugars (F-55, manufactured by Nippon Corn Starch Co., Ltd.) and various Reb (RebA, RebD and RebM) were further added. In addition, the addition amount of various Reb was adjusted so that it might become the sweetness degree (Brick of sucrose conversion) equivalent to the drink sample to which only sucrose and fructose glucose were added as a sweetener.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
 各種飲料サンプルを容器に入れ、93℃で2分間湯浴につけて殺菌した。その後、サンプル中に生じた沈殿を除去した。 Various beverage samples were placed in a container and sterilized by placing in a hot water bath at 93 ° C. for 2 minutes. Thereafter, the precipitate formed in the sample was removed.
 各種飲料サンプルを4℃で2ヶ月間保存した後、サンプルの上清に含まれるヘスペリジンの量をHPLCで測定した。なお、HPLCの条件は下記の通りである。 After various beverage samples were stored at 4 ° C. for 2 months, the amount of hesperidin contained in the sample supernatant was measured by HPLC. The HPLC conditions are as follows.
 HPLC装置:Prominanceシリーズ(島津製作所社製、システムコントローラー:SCL-10A、送液ポンプ:LC-20AD、オンライン脱気装置:DGU-20A3、オートサンプラー:SIL-20AC、カラムオーブン:CTO-20A、及びUV/VIS検出器:SPD-20Aを有する)
 カラム:CAPCELL CORE AQ(粒径2.7μm、内径3.0mm x 150mm、資生堂社製)
 移動相A:ギ酸0.1%水溶液
 移動相B:アセトニトリル
 流量:0.6mL/min
 濃度勾配条件:0.0~1.0分(15%B)→12.0分(25%B)→20.0分(75%B)→20.0~22.0分(100%B)、初期移動相による平衡化3.0分
 カラム温度:40℃
 試料注入:注入量5.0μL
 ピーク検出時間:標品による確認を要するが、概ね2.51分である。
HPLC apparatus: Prominance series (manufactured by Shimadzu Corporation, system controller: SCL-10A, liquid pump: LC-20AD, online degassing apparatus: DGU-20A3, autosampler: SIL-20AC, column oven: CTO-20A, and (With UV / VIS detector: SPD-20A)
Column: CAPCELL CORE AQ (particle size 2.7 μm, inner diameter 3.0 mm × 150 mm, manufactured by Shiseido Co., Ltd.)
Mobile phase A: 0.1% aqueous solution of formic acid Mobile phase B: acetonitrile Flow rate: 0.6 mL / min
Concentration gradient conditions: 0.0 to 1.0 minutes (15% B) → 12.0 minutes (25% B) → 20.0 minutes (75% B) → 20.0 to 22.0 minutes (100% B) ), 3.0 minutes equilibration with initial mobile phase Column temperature: 40 ° C
Sample injection: injection volume 5.0 μL
Peak detection time: Although confirmation with a standard is required, it is approximately 2.51 minutes.
 果汁のみが含まれる飲料サンプルの上清中のヘスペリジン量を100%として、各種飲料サンプルの上清に含まれるヘスペリジン量の相対値を求めた。その結果を図1に示す。 The relative value of the amount of hesperidin contained in the supernatant of various beverage samples was determined with the amount of hesperidin in the supernatant of the beverage sample containing only fruit juice as 100%. The result is shown in FIG.
 図1に示されるように、甘味料としてショ糖及び果糖のみを添加した飲料サンプルの上清に含まれるヘスペリジン量よりも、ショ糖及び果糖の一部又は全部をRebA、RebD又はRebMに置き換えた飲料サンプルの上清に含まれるヘスペリジン量の方が多いことが明らかとなった。上清中のヘスペリジン量が少ないということは、その分のヘスペリジンは沈殿したものと考えられる。よってこの結果から、RebA、RebD又はRebMの飲料への添加がヘスペリジンの沈殿化を抑制することが示唆された。その中でも、RebD及びRebMの方がRebAよりも沈殿抑制効果は高いことが示唆された。 As shown in FIG. 1, part or all of sucrose and fructose was replaced with RebA, RebD, or RebM rather than the amount of hesperidin contained in the supernatant of a beverage sample to which only sucrose and fructose were added as sweeteners. It was revealed that the amount of hesperidin contained in the supernatant of the beverage sample was larger. If the amount of hesperidin in the supernatant is small, it is considered that the amount of hesperidin has been precipitated. Therefore, from this result, it was suggested that addition of RebA, RebD or RebM to a beverage suppresses precipitation of hesperidin. Among them, it was suggested that RebD and RebM have a higher precipitation suppressing effect than RebA.

Claims (3)

  1.  以下の条件(A)、(B)及び(C):
    (A)RebD及び/又はRebMを含有する、
    (B)ヘスペリジンを含有する、並びに
    (C)飲料のBrix(ショ糖換算)が3~15である、
    を満たす、飲料。
    The following conditions (A), (B) and (C):
    (A) containing RebD and / or RebM,
    (B) contains hesperidin, and (C) the beverage has a Brix (in terms of sucrose) of 3 to 15.
    Meet the beverage.
  2.  前記条件(C)のBrix(ショ糖換算)が8~12である、請求項1に記載の飲料。 The beverage according to claim 1, wherein the condition (C) has a Brix (in terms of sucrose) of 8 to 12.
  3.  飲料中のヘスペリジンの含有量が2~250ppmである、請求項1又は2項に記載の飲料。 The beverage according to claim 1 or 2, wherein the content of hesperidin in the beverage is 2 to 250 ppm.
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WO2020116665A1 (en) * 2018-12-07 2020-06-11 Suntory Holdings Limited Composition
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