[go: up one dir, main page]

WO2017195835A1 - Procédé de production de polyphénols modifiés - Google Patents

Procédé de production de polyphénols modifiés Download PDF

Info

Publication number
WO2017195835A1
WO2017195835A1 PCT/JP2017/017725 JP2017017725W WO2017195835A1 WO 2017195835 A1 WO2017195835 A1 WO 2017195835A1 JP 2017017725 W JP2017017725 W JP 2017017725W WO 2017195835 A1 WO2017195835 A1 WO 2017195835A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyphenol
oxygen gas
modified
tea extract
precipitation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2017/017725
Other languages
English (en)
Japanese (ja)
Inventor
直也 片山
聡 脇坂
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GLICO NUTRITION CO Ltd
Original Assignee
GLICO NUTRITION CO Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by GLICO NUTRITION CO Ltd filed Critical GLICO NUTRITION CO Ltd
Publication of WO2017195835A1 publication Critical patent/WO2017195835A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/16—Tea extraction; Tea extracts; Treating tea extract; Making instant tea
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
    • A61K31/37—Coumarins, e.g. psoralen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/88—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
    • C07C39/19—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring containing carbon-to-carbon double bonds but no carbon-to-carbon triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/86—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones

Definitions

  • the present invention relates to a method for producing a modified polyphenol capable of suppressing the occurrence of precipitation and turbidity in water. Furthermore, this invention relates to the said modified polyphenol and various products containing this.
  • Polyphenol is a compound having a plurality of phenolic hydroxyl groups, and is known to be contained in various plants such as fruits and vegetables. Conventionally, it is known that polyphenol has an antioxidant effect and is effective in preventing various diseases caused by oxidative stress such as aging, cancer, heart disease and inflammation. Also, in recent years, intensive research has been conducted on the functionality of polyphenols, and depending on the type, blood LDL decrease, blood pressure increase suppression, platelet aggregation inhibition, visual acuity recovery, bowel regulation, bactericidal / antibacterial, deodorization It has also been reported that there are such effects. Under such circumstances, polyphenols are used in the fields of foods, pharmaceuticals, cosmetics and the like to add or enhance functionality.
  • tea contains catechin as a polyphenol, but it is well known that an extract obtained by hot water extraction of polyphenol from tea produces a turbidity due to the formation of tea cream.
  • Patent Document 1 reports that the water solubility of a poorly water-soluble flavonoid can be improved by drying a solution in which a poorly water-soluble flavonoid and a specific quercetin glycoside are present.
  • Patent Document 2 a water-insoluble bioactive polyphenol solution having a pH of 9 to 12 is introduced into a pH 3 to 5 aqueous solution containing a dispersion stabilizer at a temperature of less than 50 ° C. while maintaining the pH of the aqueous solution at 3 to 5. By doing this, it is disclosed that the water dispersibility of the water-insoluble bioactive polyphenol is improved.
  • Patent Document 3 discloses that by adding sulfated mucopolysaccharides to tea beverages, turbidity and precipitation due to insolubilization of polyphenols contained in tea can be suppressed. Furthermore, Patent Document 4 discloses that the turbidity at the time of cooling can be suppressed by performing freeze-concentration after performing a tannanase treatment on the hot water extract of tea. Patent Document 5 discloses that turbidity and precipitation over time can be suppressed by treating a tea extract with tannic acid followed by diatomaceous earth filtration.
  • An object of the present invention is to provide a technique for modifying polyphenols and suppressing generation of precipitation and turbidity in water without separately adding food additives or performing enzyme treatment.
  • the present inventor obtained a modified polyphenol capable of suppressing the occurrence of precipitation and turbidity in water by supplying oxygen gas to a solution containing polyphenol.
  • the modified polyphenol obtained by the treatment can suppress the occurrence of precipitation and turbidity of the unmodified polyphenol in water by coexisting with the unmodified polyphenol.
  • the present invention has been completed by further studies based on these findings.
  • Item 1 The manufacturing method of modified polyphenol including the process of supplying oxygen gas with respect to the solution containing polyphenol.
  • the polyphenol is at least selected from the group consisting of flavonols, flavanols, stilbenoids, flavones, isoflavones, flavans, flavonones, flavonols, chalcones, anthocyanidins, and plant extracts containing these Item 2.
  • Item 3. Item 3.
  • Item 4. Item 4.
  • Item 10. Item 7. A polyphenol stabilizer comprising the modified polyphenol obtained by the production method according to any one of Items 1 to 6.
  • Item 11. Item 7. A method for stabilizing an unmodified polyphenol, wherein the modified polyphenol obtained by the production method according to any one of Items 1 to 6 coexists with an unmodified polyphenol in the presence of water.
  • the present invention it is possible to produce a modified polyphenol capable of suppressing the occurrence of precipitation and turbidity in water by a simple method without separately adding food additives or performing enzyme treatment. Therefore, it becomes possible to provide a polyphenol-containing product having excellent storage stability by using the modified polyphenol obtained by the present invention in various products such as foods, cosmetics, and pharmaceuticals.
  • the modified polyphenol obtained by the present invention not only can suppress the occurrence of precipitation and turbidity in water, but also allows the unmodified polyphenol to precipitate in water by coexisting with the unmodified polyphenol. The occurrence of turbidity can also be suppressed.
  • Example 1 the result of confirming the occurrence of precipitation at pH 7 by supplying oxygen gas to an alkaline solution containing quercetin for 0 to 14 hours is shown.
  • Example 2 the result of having confirmed the production
  • Example 3 the result of confirming the occurrence of precipitation at pH 7 and pH 5 by supplying oxygen gas to an alkaline solution containing curcumin is shown.
  • Example 4 with respect to the black tea extract (pH 10.3), nitrogen gas is 0.5 vvm, or air (oxygen content: about 20 v / v%) is 0.1 vvm, 0.25 vvm, and 0.5 vvm.
  • oxygen gas is supplied to the black tea extract (pH 8, pH 10, and pH 12.5), and the results of confirming the occurrence of precipitation at pH 7, pH 5, and pH 3 are shown.
  • oxygen gas is supplied to the black tea extract (pH 6 and pH 12) for 3 hours and 6 hours, and the results of confirming the occurrence of precipitation at pH 7, pH 5 and pH 3 are shown.
  • Example 6 the result of having confirmed the generation
  • Example 7 the result of confirming the occurrence of precipitation at pH 7, pH 5 and pH 3 after supplying oxygen gas to the black tea extract (pH 3 to 7) for 72 hours is shown.
  • Example 7 the result of confirming the occurrence of precipitation at pH 7, pH 5 and pH 3 by supplying oxygen gas to the black tea extract (pH 3 to 7) for 144 hours is shown.
  • Example 7 after leaving still at 50 degreeC for 144 hours without supplying oxygen gas to black tea extract (pH7), the result of having confirmed generation
  • Example 8 the modified black tea extract obtained by supplying oxygen gas to the black tea extract (pH 12.5) was converted into 0% by volume, 1% by volume, and 5% by volume to the unmodified black tea extract. The results of confirming the occurrence of precipitation after mixing to 10% by volume and 20% by volume are shown.
  • Example 9 it was obtained by supplying oxygen gas to the modified green tea extract obtained by supplying oxygen gas to the green tea extract (pH 12.5) and black tea extract (pH 12.5).
  • the modified black tea extract is mixed with the unmodified black tea extract so as to be 0% by volume, 1% by volume, 5% by volume, and 10% by volume, and the result of confirming the occurrence of precipitation is shown.
  • the “modified polyphenol” refers to a polyphenol obtained by the production method of the present invention and having improved solubility and stability in water.
  • the production method of the present invention is a method for producing a modified polyphenol, and includes a step of supplying oxygen gas to a solution containing polyphenol.
  • a step of supplying oxygen gas to the polyphenol the solubility and / or stability of the polyphenol in water is modified and improved, and as a result, a polyphenol that can suppress the occurrence of precipitation and turbidity is obtained. It is done. Therefore, the method for producing a modified polyphenol of the present invention can be implemented as a method for modifying a polyphenol.
  • the manufacturing method of this invention is explained in full detail.
  • Raw material polyphenol polyphenol is a compound which exists in plants and has a plurality of phenolic hydroxyl groups in the molecule.
  • the origin of the polyphenol used as a raw material is not particularly limited, and may be any of plant-derived, microorganism-produced, chemically synthesized, and the like.
  • the type of polyphenol to be manufactured (ie, the modification target) in the present invention is not particularly limited, and may be either a flavonoid polyphenol or a non-flavonoid (phenolic acid) polyphenol.
  • flavonoid polyphenol examples include flavones, flavonols, flavanones, flavanols, flavonols, isoflavones, anthocyanins, chalcones, stilbenoids and the like.
  • flavones include flavone, apigenin, luteonin, apigeninidine, luterionidine, baicalein and the like.
  • flavonols include quercetin, kaempferol, myricetin and the like.
  • flavanones include narizine, hesperidin, liquiritigen and the like.
  • flavanols include catechin (epicatechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, theaflavin, etc.), theaflavin, leucoanthocyanidins, and the like.
  • flavonols include alpinone and taxifolin.
  • isoflavones include genistein, daidzein, daidzin, glycitein, equol, biocanin A, cumestrol, puerarin, formononetin, and the like.
  • anthocyanins include pelargonidin, cyanidin, petunidin, peonidin, petunidin, delphinidin, and malvidin.
  • chalcones include carthamin and proretin.
  • stilbenoids include resveratrol.
  • non-flavonoid polyphenols examples include ellagic acid, coumarin, curcumin, chlorogenic acid, lignan, sesamin and the like.
  • the polyphenol used as a raw material in the production method of the present invention may be one that is purified and present alone, or may be a mixture of two or more polyphenols.
  • Examples of polyphenols in which two or more kinds of polyphenols are mixed include plant pigments and plant extracts.
  • plant pigments include pigments containing flavones such as cuoriyan pigments; pigments containing various flavonoids such as tamarind pigments; pigments mainly containing flavonols such as onion pigments; anthocyanins such as cacao pigments And pigments mainly containing.
  • tea such as green tea, black tea, oolong tea, apples, blueberries, grapes, strawberries, strawberries, onions, purple potatoes, turmeric, peaches, citrus fruits and vegetables are extracted. Thing etc. are mentioned.
  • flavonols flavanols, stilbenoids, flavones, isoflavones, flavans, flavonones are preferred.
  • Flavonols, chalcones, anthocyanidins plant extracts containing these; more preferably flavonols, flavanols, stilbenoids, plant extracts containing these; more preferably quercetin, catechin, theaflavins, resvera Troll, plant extracts containing these (for example, tea extracts such as black tea extract, green tea extract, oolong tea extract, and plant extracts such as fruits and vegetables).
  • polyphenols purified or extracted from plant raw materials may be used as raw materials, or plant raw materials containing polyphenols themselves may be provided.
  • plant raw materials containing polyphenol are subjected to an oxygen gas supply process described later, in the oxygen gas supply process, it becomes possible to simultaneously perform polyphenol extraction and polyphenol extraction, thereby simplifying the manufacturing process. Can be achieved.
  • the plant raw material itself containing polyphenol is subjected to an oxygen gas supply step described later, the plant raw material is subjected to a drying treatment, a degreasing treatment, a fermentation treatment, a roasting treatment, or the like as necessary.
  • crushing processes such as shredding and crushing, may be performed.
  • Oxygen gas supply process In the manufacturing method of this invention, an oxygen gas supply process is performed by supplying oxygen gas to the solution containing polyphenol.
  • the liquid property of the solution containing polyphenol is not particularly limited, and may be any of acidic, neutral, or alkaline.
  • Examples of the pH of the solution containing polyphenol include 2 to 14.
  • the pH of the solution containing the polyphenol is preferably neutral or alkaline, more preferably alkaline. More specifically, the pH of the solution containing polyphenol is usually 3 or more, 4 or more, preferably 5 or more, more preferably 6 or more, still more preferably 7 or more, particularly preferably pH 8 or more, and still more preferably pH 9 to 13, most preferably pH 11-13.
  • the target modified polyphenol can be efficiently produced, but even if the solution is acidic or neutral, the oxygen gas supply rate can be increased,
  • the target modified polyphenol can be produced by extending the supply time of the oxygen gas.
  • the pH of the solution may be set to less than 8, specifically, pH 3 or more and less than 8, or pH 3 to 7.5. Good.
  • the concentration of polyphenol in the solution supplied for oxygen gas supply may be appropriately set according to the type of polyphenol used, the state of the polyphenol (the state of the refined product, the extract, the state of the plant raw material, etc.).
  • the concentration of polyphenols in the solution is, for example, 0.1 to 2% by mass, preferably 0.1 to 5% by mass, and more preferably 0. 1 to 3% by mass.
  • the amount of the solution is 5 to 50 times, preferably 5 to 40 times, more preferably 5 to 40 times the weight of the plant raw material containing polyphenol. The amount is 5 to 30 times.
  • the pH of the solution to be supplied for oxygen gas supply may be appropriately set using a pH adjuster that can be used in the food and drink field as necessary.
  • the alkali used for adjusting the pH of the solution may be any alkali that can be used in the food and drink field.
  • Sodium hydroxide, potassium hydroxide, sodium phosphate, potassium phosphate, sodium carbonate, potassium carbonate, calcium hydroxide, barium hydroxide, calcium hydroxide, calcium carbonate, ammonium hydroxide, aqueous ammonia, aluminum hydroxide, hydroxide Iron etc. are mentioned. These alkalis may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the solution to be supplied with oxygen gas is optionally monovalent lower alcohols such as ethanol and propanol; polyhydric lower alcohols such as propylene glycol, butylene glycol and glycerin; preservatives and solubilization Additives such as agents and antifoaming agents may be included.
  • the alkaline aqueous solution contains a solvent such as ethanol or propylene glycol in order to efficiently extract polyphenol from the plant raw material. Also good.
  • the temperature condition in the oxygen gas supply step is not particularly limited, and examples thereof include 0 to 130 ° C., preferably 30 to 100 ° C., more preferably 50 to 100 ° C., and more preferably 70 to 100 ° C.
  • the oxygen gas supplied in the oxygen gas supply step may be the oxygen gas itself, but includes oxygen components such as air, as long as the oxygen gas is included.
  • the gas that is present may be used. From the viewpoint of reducing the manufacturing cost, etc., air is preferably used as the oxygen supplied during the extraction process.
  • the oxygen gas may be supplied to the solution containing polyphenol using an air pump, a microbubble generator, or the like so that the air on the liquid surface is taken into the solution.
  • the solution may be vigorously stirred.
  • the oxygen gas supply speed is appropriately set according to the pH at the time of oxygen gas supply, the amount of the liquid to which the oxygen gas is supplied, the presence or absence of stirring during the oxygen gas supply, the stirring speed, etc., for example, 0.05 vvm
  • the above is preferably 0.05 to 1 vvm, more preferably 0.1 to 0.5 vvm.
  • the oxygen gas supply rate shown here refers to the supply rate of the oxygen gas itself. That is, for example, when air is used as the oxygen gas, oxygen is contained in the air at about 20% by volume. Therefore, the air may be supplied at a rate five times the supply rate.
  • the oxygen gas supply time in the oxygen gas supply step may be appropriately set according to the pH at the time of oxygen gas supply, the amount of liquid to which oxygen gas is supplied, the presence or absence of stirring during the oxygen gas supply, the stirring speed, and the like. For example, 1 hour or more is mentioned. More specifically, when the pH of the solution containing polyphenol is 8 or more, the supply time of the oxygen gas is, for example, 1 to 10 hours, preferably 1 to 5 hours. For example, when the pH of the solution containing polyphenol is 6 or more and less than 8, the oxygen gas supply time is, for example, 1 to 144 hours, preferably 1 to 72 hours. When the pH of the solution containing polyphenol is less than 6, the oxygen gas supply time is, for example, 2 to 192 hours, preferably 3 to 144 hours.
  • the liquid obtained after the supply of oxygen gas is modified, and the modified polyphenol in which the occurrence of precipitation and turbidity in water is suppressed is dissolved.
  • the liquid fraction is recovered as a modified polyphenol solution.
  • the modified polyphenol solution may be used as it is for various applications described later, or may be used for various applications after neutralization treatment, concentration treatment, drying treatment and the like, if necessary.
  • modified polyphenols can be used in place of all or part of the conventional polyphenols in various products such as food and drink, pharmaceuticals, and cosmetics. Can be used.
  • the pH of the product to which the modified polyphenol obtained by the production method of the present invention is added is not particularly limited, and examples thereof include 3 to 10, preferably 3 to 9, and more preferably 3 to 8.
  • the conventional polyphenol has a drawback that the solubility is lowered in the acidic region and becomes unstable and easily precipitates.
  • the modified polyphenol has solved such a disadvantage, and even in the acidic region. It has excellent solubility, can suppress the occurrence of precipitation, and can stably maintain the dissolved state.
  • a suitable example of the pH of the product to which the modified polyphenol is added is acidic, preferably 3 or more and less than 7, more preferably 5 or more and less than 7. .
  • the resulting modified polyphenol when using tea leaves such as green tea, black tea, oolong tea, or an extract thereof as the raw material polyphenol, the resulting modified polyphenol can be used as a raw material (concentrated liquid) for various tea beverages. it can.
  • tea beverages (green tea, black tea, oolong tea, etc.) produced using the modified polyphenol obtained by the production method of the present invention can suppress the occurrence of turbidity and precipitation due to insolubilization of polyphenol, and are excellent in storage. Stability can be provided.
  • the resulting modified polyphenol can be used as a colorant for coloring various products into desired colors.
  • the modified polyphenol is used as a colorant for foods and drinks, the type of the food or drink to be added is not particularly limited as long as coloring with the modified polyphenol is required.
  • foods such as sauces, sauces, soy sauce, curry roux, pickles, Tsukudani, jelly, yogurt, pickles, etc .; beer, sparkling sake, and other sparkling brews
  • Carbonated alcoholic beverages such as liquor, liqueur and sparkling wine
  • beer-flavored non-alcoholic beverages such as beer-flavored non-alcoholic beverages
  • carbonated soft drinks such as cola and ginger ale
  • sparkling orange juice beverage sparkling grape juice beverage
  • sparkling apple juice beverage sparkling lemon Examples include fruit juice drinks.
  • the amount of the modified polyphenol added to each product may be appropriately set according to the type of product to be added, the type of polyphenol, the purpose of addition, etc., and for example, 0.01 to 30% by mass may be mentioned.
  • modified polyphenol obtained by the above production method is turbidity caused by untreated polyphenol in the presence of water when coexisting with unmodified polyphenol (hereinafter, unmodified polyphenol).
  • unmodified polyphenol can be used as a stabilizer for polyphenols. That is, this invention provides the stabilizer of polyphenol containing the modified polyphenol obtained by the said manufacturing method further.
  • the stabilizer of the present invention is added to a product containing unmodified polyphenol (polyphenol to which the production method of the present invention is not applied) to stabilize the unmodified polyphenol, and in the presence of water. Used to suppress turbidity and precipitation caused by unmodified polyphenols.
  • the polyphenol to be stabilized is not particularly limited, and specific examples include the polyphenols described in the column of “1. Production method of modified polyphenol”.
  • the application object in the stabilizer of the present invention is limited to that the stability of unmodified polyphenol in the presence of water is required, including unmodified polyphenol. It is not particularly limited, and may be a concentrate (additive) of unmodified polyphenol, and may be a food, drink, cosmetic, pharmaceutical, etc. containing unmodified polyphenol.
  • any concentrate may be used as long as it is used as an additive in foods and drinks, cosmetics, pharmaceuticals, and the like.
  • Pigment preparations; polyphenol extracts such as tea extract and the like are suitable.
  • foods and drinks are suitable.
  • suitable examples of food and drink include tea beverages such as green tea, black tea, oolong tea; carbonated alcoholic beverages such as beer, sparkling wine, other sparkling brews, liqueur, sparkling wine; beer-flavored non-alcoholic beverages; cola, Carbonated soft drinks such as ginger ale; effervescent orange juice drinks, effervescent grape juice drinks, effervescent apple juice drinks, effervescent lemon juice drinks; And foods such as pickles.
  • tea beverages have the disadvantage that precipitates are easily generated during storage due to destabilization of polyphenols, but the stabilizer of the present invention can overcome such disadvantages of tea beverages. Since it can impart excellent storage stability to tea beverages, it is particularly suitable as an application target of the stabilizer of the present invention.
  • the amount of the stabilizer of the present invention may be set as appropriate according to the type of unmodified polyphenol to be stabilized, for example, 100 mass of unmodified polyphenol to be stabilized.
  • the modified polyphenol is 1 to 50 parts by weight, preferably 1 to 40 parts by weight, and more preferably 1 to 30 parts by weight per part.
  • Example 1 100 g of quercetin powder was dissolved in 2000 ml of an aqueous sodium hydroxide solution. The pH at this time was 12.5. Air was supplied for 3 to 24 hours by feeding 0.5 vvm air (oxygen content: about 20 v / v%) while stirring the obtained solution at 200 rpm. After 3 hours, 8 hours, and 24 hours from the start of air supply, the pH was adjusted to 7.0 with 10% by mass hydrochloric acid. Subsequently, after transferring to a microtube and carrying out the centrifugation process, the solubility was confirmed by observing the amount of deposits.
  • Air was supplied for 3 to 24 hours by feeding 0.5 vvm air (oxygen content: about 20 v / v%) while stirring the obtained solution at 200 rpm. After 3 hours, 8 hours, and 24 hours from the start of air supply, the pH was adjusted to 7.0 with 10% by mass hydrochloric acid. Subsequently, after transferring to a microtube and carrying out the centrifugation process
  • Example 2 Resveratrol extract (powder, containing 96.0% by mass of resveratrol) (2.5 g) was added to 100 ml of ion-exchanged water and dispersed by stirring. The dispersed liquid was adjusted to pH 7.0 and pH 12.5 with a 20% by mass aqueous sodium hydroxide solution. 20 ml of each adjusted solution was put into a 500 ml Erlenmeyer flask, and contact reaction with air was performed at 120 rpm and 50 ° C. for 24 hours in a shaking incubator.
  • the liquid after contact reaction with air for 24 hours was adjusted to pH 7.0 and pH 5.0 with a 10 mass% hydrochloric acid aqueous solution.
  • the resveratrol extract which has not performed the contact reaction with air (oxygen gas) was also disperse
  • These solutions were allowed to stand at 5 ° C. for 24 hours, and then the absorbance at 660 nm was measured as turbidity with a spectrophotometer.
  • each liquid after leaving still at 5 degreeC for 24 hours was centrifuged at 3000 rpm for 10 minutes, and the presence or absence of precipitation was confirmed visually.
  • the turbidity value mainly reflects turbidity caused by polyphenols, but is also affected by browning caused by air (oxygen gas). The same applies to turbidity measured in other examples described below.
  • Example 3 Curcumin (2.5 g) was added to 100 ml of ion-exchanged water and dispersed by stirring. The dispersed liquid was adjusted to pH 12.5 with a 20% by mass aqueous sodium hydroxide solution. 20 ml of the prepared solution was put into a 500 ml Erlenmeyer flask, and contact reaction with air (oxygen content: about 20 v / v%) was carried out at 120 rpm and 50 ° C. for 24 hours in a shaking incubator.
  • the liquid after contact reaction with air for 24 hours was adjusted to pH 7.0 and pH 5.0 with a 10 mass% hydrochloric acid aqueous solution. Further, curcumin not subjected to contact reaction with air (oxygen gas) was also dispersed in water so as to have the same concentration as described above, and similarly adjusted to pH 7.0 and pH 5.0. These solutions were allowed to stand at 5 ° C. for 24 hours, and then the absorbance at 660 nm was measured as turbidity with a spectrophotometer. Moreover, each liquid after leaving still at 5 degreeC for 24 hours was centrifuged at 3000 rpm for 10 minutes, and the presence or absence of precipitation was confirmed visually.
  • Table 2 shows the results obtained. Moreover, the result of having observed the external appearance after centrifugation is shown in FIG. In curcumin that was not treated by supplying air (oxygen gas), significant precipitation and turbidity were observed in the liquid at pH 7.0. However, when air (oxygen gas) was supplied to curcumin, pH 7 The occurrence of precipitation and turbidity was remarkably suppressed in the liquids of 0.0 and 5.0.
  • Example 4 Extraction treatment was performed by adding 500 ml of ion-exchanged water heated to 80 ° C. to 50 g of tea leaves (sold by Unilever Japan) and dipping for 5 minutes. The obtained liquid was filtered with a filter paper to collect the filtrate. The collected filtrate was adjusted to pH 6.5 with sodium bicarbonate to obtain a black tea extract.
  • the obtained black tea extract was adjusted to pH 8.0, pH 10.0, and pH 12.5 with a 20% by mass aqueous sodium hydroxide solution. 20 ml of each prepared solution was put into a 500 ml Erlenmeyer flask, and contact reaction with air (oxygen content: about 20 v / v%) was carried out at 120 rpm and 50 ° C. for 24 hours using a shaking incubator.
  • the solution after contact reaction with air for 24 hours was adjusted to pH 7.0, pH 5.0, and pH 3.0 with a 10 mass% hydrochloric acid aqueous solution.
  • the black tea extract which has not performed the contact reaction with air (oxygen gas) it adjusted to pH7.0, pH5.0, and pH3.0 similarly.
  • These solutions were allowed to stand at 5 ° C. for 24 hours, and then the absorbance at 660 nm was measured as turbidity with a spectrophotometer.
  • each liquid after leaving still at 5 degreeC for 24 hours was centrifuged at 3000 rpm for 10 minutes, and the presence or absence of precipitation was confirmed visually.
  • Table 3 shows the obtained results. Moreover, the result of having observed the external appearance after centrifugation is shown in FIG.
  • air oxygen gas
  • FIG. 1 the black tea extract that was not treated by supplying air (oxygen gas)
  • significant precipitation and turbidity were observed in the pH range of 3.0 to 7.0, but air (oxygen gas) was added to the black tea extract.
  • air oxygen gas
  • the black tea extract supplied with air (oxygen gas) under the condition of 12.5 the occurrence of precipitation was effectively suppressed even in pH 3 water.
  • Example 5 Extraction processing was performed by adding 8000 ml of ion-exchanged water heated to 80 ° C. to 700 g of tea leaves (sold by Unilever Japan) and dipping for 5 minutes. The obtained liquid was filtered with a filter paper, and the filtrate was collected to obtain a black tea extract.
  • the obtained black tea extract was adjusted to pH 10.3 with a 20% by mass aqueous sodium hydroxide solution and divided into 4 parts each with 1600 ml. Next, while sending gas to each solution so that nitrogen gas 0.5 vvm or air (oxygen content: about 20 v / v%) 0.1 vvm, 0.25 vvm, and 0.5 vvm, 150 rpm, 50 The contact reaction with nitrogen gas or air (oxygen gas) was performed at 17 ° C. for 17 hours.
  • the liquid after the contact reaction with gas was adjusted to pH 7.0, pH 5.0, and pH 3.0 with a 10 mass% hydrochloric acid aqueous solution. Moreover, it adjusted to pH7.0, pH5.0, and pH3.0 similarly about the black tea extract which is not performing the contact reaction with gas.
  • These solutions were allowed to stand at 5 ° C. for 24 hours, and then the absorbance at 660 nm was measured as turbidity with a spectrophotometer. Moreover, each liquid after leaving still at 5 degreeC for 24 hours was centrifuged at 3000 rpm for 10 minutes, and the presence or absence of precipitation was confirmed visually.
  • Table 4 shows the obtained results. Moreover, the result of having observed the external appearance after centrifugation is shown in FIG.
  • the black tea extract not treated with the gas supply and the black tea extract treated with the nitrogen gas supply significant precipitation and turbidity occurred in the pH range of 3.0 to 7.0.
  • air oxygen gas
  • the occurrence of precipitation and turbidity could be remarkably suppressed.
  • the black tea extract supplied with air at an air flow rate of 0.25 vvm or more (particularly 0.5 vvm) the occurrence of precipitation was remarkably suppressed even in pH 3 water.
  • Example 6 Extraction processing was performed by adding 250 ml of ion-exchanged water heated to 80 ° C. to 25 g of tea leaves (available from Unilever Japan) and immersing in 5 minutes. The obtained liquid was filtered with a filter paper, and the filtrate was collected to obtain a black tea extract.
  • the pH of the obtained black tea extract was 4.90.
  • the obtained black tea extract was adjusted to pH 12.0 and 6.0 with a 20% by mass aqueous sodium hydroxide solution.
  • 50 ml of each black tea extract adjusted to pH was put into a 500 ml Erlenmeyer flask, and further 50 ml of ion-exchanged water was added. Then, in a shaking incubator, air (oxygen content: 120 rpm, 24 hours). Contact reaction with about 20 v / v%).
  • Table 5 shows the obtained results. Moreover, the result of having observed the external appearance after centrifugation is shown to FIG. In the black tea extract not treated with air (oxygen gas), significant precipitation and turbidity were observed in the pH range of 3.0 to 5.0. On the other hand, when air was supplied to the black tea extract, the occurrence of precipitation and turbidity could be suppressed. In particular, when the pH when air was supplied was 12.0, precipitation and turbidity could be effectively suppressed by supplying air for a short time. Moreover, even if the pH at the time of supplying air was 6.0, it was possible to suppress the occurrence of precipitation and turbidity by increasing the air supply time.
  • Example 7 Extraction treatment was performed by adding 500 ml of ion-exchanged water heated to 80 ° C. to 50 g of tea leaves (sold by Unilever Japan) and dipping for 5 minutes. The obtained liquid was filtered with a filter paper, and the filtrate was collected to obtain a black tea extract.
  • the pH of the obtained black tea extract was 5.04.
  • the black tea extract obtained was adjusted to pH 3.0, 4.0, 6.0, and 7.0 with a 20% by mass aqueous sodium hydroxide solution or a 10% by mass aqueous hydrochloric acid solution.
  • the tea non-pH adjusted liquid it used as a sample of pH5.0.
  • 50 ml of black tea extract of each pH was put into a 500 ml Erlenmeyer flask, and further 50 ml of ion-exchanged water was added. Then, the mixture was shaken in an incubator at 120 rpm and 50 ° C. with air (oxygen content: about 20 v / v). %).
  • the black tea liquid which adjusted pH to 7.0, after putting 50 ml into a 500 ml Erlenmeyer flask and adding 50 ml of ion-exchange water, it can also be left still for 50 hours at 50 ° C. without shaking. went.
  • the liquid was recovered and adjusted to pH 7.0, pH 5.0, and pH 3.0 with a 20% by mass sodium hydroxide aqueous solution or a 10% by mass hydrochloric acid aqueous solution. . Moreover, it adjusted to pH7.0, pH5.0, and pH3.0 similarly about the black tea extract which is not performing the contact reaction with gas.
  • These solutions were allowed to stand at 5 ° C. for 24 hours, and then the absorbance at 660 nm was measured as turbidity with a spectrophotometer. Moreover, each liquid after leaving still at 5 degreeC for 24 hours was centrifuged at 3000 rpm for 10 minutes, and the presence or absence of precipitation was confirmed visually.
  • Table 6 shows the obtained results.
  • the results of observing the appearance after centrifugation are shown in FIGS.
  • Black tea extract that has not been treated by gas supply and black tea extract that has been adjusted to pH 7.0 and allowed to stand for 144 hours at 50 ° C. show significant precipitation and turbidity in the pH range of 3.0 to 7.0. Admitted.
  • air oxygen gas
  • the occurrence of precipitation could be suppressed.
  • the pH at the time of supplying air was 6.0 or more
  • precipitation and turbidity generation could be effectively suppressed by supplying air for 72 hours.
  • even if pH at the time of supplying air was 6.0 or less the generation amount of precipitation and the degree of turbidity could be reduced by increasing the air supply time.
  • Example 8 100 g of ion-exchanged water heated to 80 ° C. was added to 10 g of tea leaves (sold by Unilever Japan) and immersed for 5 minutes for extraction treatment. The obtained liquid was filtered with a filter paper, and the filtrate was collected to obtain a black tea extract.
  • the obtained black tea extract was adjusted to pH 12.5 with a 20% by mass aqueous sodium hydroxide solution.
  • 20 ml of the prepared solution was put into a 500 ml Erlenmeyer flask, and contact reaction with air (oxygen content: about 20 v / v%) was carried out at 120 rpm and 50 ° C. for 24 hours in a shaking incubator.
  • the liquid after contact reaction with gas was adjusted to pH 7.0 with a 10% by mass hydrochloric acid aqueous solution to obtain a modified black tea extract.
  • the modified black tea extract is mixed with the unmodified black tea extract so as to be 0% by volume, 1% by volume, 5% by volume, 10% by volume, and 20% by volume, and left at 5 ° C. for 24 hours. did.
  • the light absorbency of 660 nm was measured with the spectrophotometer as turbidity.
  • each liquid mixture after leaving still at 24 degreeC for 5 hours was centrifuged at 3000 rpm for 10 minutes, and the presence or absence of precipitation was confirmed visually.
  • the modified black tea extract itself was also allowed to stand under the same conditions as described above, and evaluated for turbidity and precipitation.
  • Table 7 shows the obtained results. Moreover, the result of having observed the external appearance after centrifugation is shown in FIG. From this result, the modified black tea extract that has been treated by supplying air (oxygen gas) is added to the unmodified black tea extract, thereby suppressing the precipitation of the unmodified black tea extract and the occurrence of turbidity. It became clear that there was an effect.
  • Example 9 Extraction processing was performed by adding 100 ml of ion-exchanged water heated to 80 ° C. to 10 g of green tea (manufactured by Yamashiro Bussan) and immersing in 5 minutes. The obtained liquid was filtered with a filter paper, and the filtrate was collected to obtain a green tea extract.
  • the obtained green tea extract was adjusted to pH 12.5 with a 20% by mass aqueous sodium hydroxide solution.
  • 50 ml of the prepared solution was put into a 500 ml Erlenmeyer flask, and contact reaction with air (oxygen content: about 20 v / v%) was carried out at 120 rpm and 50 ° C. for 24 hours in a shaking incubator.
  • the liquid after the contact reaction with gas was adjusted to pH 7.0 with a 10% by mass hydrochloric acid aqueous solution to obtain a modified green tea extract.
  • the modified green tea extract and the modified black tea produced in Example 8 are mixed with the unmodified black tea extract so that the volume is 0% by volume, 1% by volume, 5% by volume, and 10% by volume. It left still at 5 degreeC for 24 hours. About each liquid mixture after standing at 5 degreeC for 24 hours, the light absorbency of 660 nm was measured with the spectrophotometer as turbidity. Furthermore, each liquid mixture after leaving still at 24 degreeC for 5 hours was centrifuged at 3000 rpm for 10 minutes, and the presence or absence of precipitation was confirmed visually. For comparison, the modified green tea extract and the modified black tea extract itself were also allowed to stand under the same conditions as described above, and evaluated for turbidity and precipitation.
  • Table 8 shows the obtained results. Moreover, the result of having observed the external appearance after centrifugation is shown in FIG. From this result, the modified green tea extract and the modified black tea extract treated by the supply of air (oxygen gas) were added to the unmodified black tea extract to precipitate the unmodified black tea extract and It was confirmed that there is an action to suppress the occurrence of turbidity.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Polymers & Plastics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Tea And Coffee (AREA)
  • Pyrane Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

Un but de l'invention est de fournir une technique de modification de polyphénols pour supprimer l'apparition de précipitation et de turbidité dans l'eau sans addition séparée d'additifs alimentaires ou mise en oeuvre de traitement enzymatique. Des polyphénols modifiés ayant une solubilité et une stabilité améliorées dans l'eau sont obtenus par apport de gaz oxygène dans une solution comprenant des polyphénols.
PCT/JP2017/017725 2016-05-10 2017-05-10 Procédé de production de polyphénols modifiés Ceased WO2017195835A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016-094537 2016-05-10
JP2016094537A JP2019131468A (ja) 2016-05-10 2016-05-10 改質化ポリフェノールの製造方法

Publications (1)

Publication Number Publication Date
WO2017195835A1 true WO2017195835A1 (fr) 2017-11-16

Family

ID=60267115

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2017/017725 Ceased WO2017195835A1 (fr) 2016-05-10 2017-05-10 Procédé de production de polyphénols modifiés

Country Status (2)

Country Link
JP (1) JP2019131468A (fr)
WO (1) WO2017195835A1 (fr)

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3163539A (en) * 1961-09-07 1964-12-29 Standard Brands Inc Instant tea
US3484246A (en) * 1966-06-21 1969-12-16 Lipton Inc Thomas J Alkaline conversion of green tea
JPS61260835A (ja) * 1985-05-08 1986-11-19 ソシエテ　デ　プロデユイ　ネツスル　ソシエテ　アノニム 冷水可溶インスタント茶の製造法
JP2000287623A (ja) * 1999-03-31 2000-10-17 Unilever Nv 茶濃縮物の製造方法
JP2004167218A (ja) * 2002-10-28 2004-06-17 Takasago Internatl Corp 消臭剤組成物
WO2005105021A1 (fr) * 2004-04-27 2005-11-10 Takasago International Corporation Composition d'une preparation cosmetique capillaire
WO2005105297A1 (fr) * 2004-04-27 2005-11-10 Takasago International Corporation Composition d'absorbeur d'oxygene
JP2013111051A (ja) * 2011-11-30 2013-06-10 Uha Mikakuto Co Ltd 機能性の向上された茶抽出処理物の製造方法
JP2015122992A (ja) * 2013-12-26 2015-07-06 大塚食品株式会社 テアフラビン類の製造方法、及びテアフラビン類を含む飲料

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3163539A (en) * 1961-09-07 1964-12-29 Standard Brands Inc Instant tea
US3484246A (en) * 1966-06-21 1969-12-16 Lipton Inc Thomas J Alkaline conversion of green tea
JPS61260835A (ja) * 1985-05-08 1986-11-19 ソシエテ　デ　プロデユイ　ネツスル　ソシエテ　アノニム 冷水可溶インスタント茶の製造法
JP2000287623A (ja) * 1999-03-31 2000-10-17 Unilever Nv 茶濃縮物の製造方法
JP2004167218A (ja) * 2002-10-28 2004-06-17 Takasago Internatl Corp 消臭剤組成物
WO2005105021A1 (fr) * 2004-04-27 2005-11-10 Takasago International Corporation Composition d'une preparation cosmetique capillaire
WO2005105297A1 (fr) * 2004-04-27 2005-11-10 Takasago International Corporation Composition d'absorbeur d'oxygene
JP2013111051A (ja) * 2011-11-30 2013-06-10 Uha Mikakuto Co Ltd 機能性の向上された茶抽出処理物の製造方法
JP2015122992A (ja) * 2013-12-26 2015-07-06 大塚食品株式会社 テアフラビン類の製造方法、及びテアフラビン類を含む飲料

Also Published As

Publication number Publication date
JP2019131468A (ja) 2019-08-08

Similar Documents

Publication Publication Date Title
JP5000373B2 (ja) 水溶性フラボノイド組成物およびその製造方法、ならびに水溶性フラボノイド組成物を含む食品等
CN101081858B (zh) 类黄酮糖加成产物、生产方法及其应用
AU2009335206B2 (en) Food products enriched with methylxanthines
Dassoff et al. Potential development of non-synthetic food additives from orange processing by-products—a review.
WO2008110225A1 (fr) Compositions de caroténoïdes contenant de la gomme arabique modifiée
JP4790561B2 (ja) フラボノイド組成物、その製造方法および用途
JP2002027957A (ja) 植物ポリフェノール含有液体組成物
JP5525700B2 (ja) 液体組成物並びにこれらを用いた飲料及び化粧料
JP5713571B2 (ja) メイラード反応阻害剤およびＡＧＥｓ生成抑制剤
WO2001048091A1 (fr) Stabilisants destines a des compositions a forte teneur en anthocyanine
JP5040060B2 (ja) メチオニン配合内服液剤
JP2021016380A (ja) 乳化粒子の微細化促進用、粗大粒子の形成抑制用、又は乳化安定性向上用剤
US12256767B2 (en) Gardenia blue pigment and method for producing the same
JP6880757B2 (ja) 経口液体組成物
JP6931747B2 (ja) 容器詰飲料
WO2017195835A1 (fr) Procédé de production de polyphénols modifiés
KR20150009164A (ko) 쑥 추출물 및 그 제조방법
WO2013141267A1 (fr) Stabilisateur de polyphénol et composition, marchandises traitées et contenant ledit stabilisateur
JP4571575B2 (ja) プロアントシアニジン含有茶飲料及びその製造法
JP7423179B2 (ja) ポリフェノールを含む食品
JP4912578B2 (ja) 褐変防止剤
WO2022044291A1 (fr) Pigment bleu et son procédé de production
JPH07132072A (ja) 飲料の香味変化防止剤
JP6793306B2 (ja) 果皮酵素処理物の製造方法
JP7249764B2 (ja) ポリフェノール類を含有する沈殿が抑制された液状組成物

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17796194

Country of ref document: EP

Kind code of ref document: A1

122 Ep: pct application non-entry in european phase

Ref document number: 17796194

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP