WO2007114304A1 - Inhibiteur de production de benzène et procédé d'inhibition de production de benzène - Google Patents

Inhibiteur de production de benzène et procédé d'inhibition de production de benzène Download PDF

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Publication number
WO2007114304A1
WO2007114304A1 PCT/JP2007/056996 JP2007056996W WO2007114304A1 WO 2007114304 A1 WO2007114304 A1 WO 2007114304A1 JP 2007056996 W JP2007056996 W JP 2007056996W WO 2007114304 A1 WO2007114304 A1 WO 2007114304A1
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Prior art keywords
benzoic acid
benzene
extract
acid
containing composition
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PCT/JP2007/056996
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English (en)
Japanese (ja)
Inventor
Ryosuke Shimizu
Hiroshi Shimabayashi
Masamitsu Moriwaki
Hisashi Tanaka
Masayuki Nishino
Mikio Nakamura
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San-Ei Gen F.F.I., Inc.
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Application filed by San-Ei Gen F.F.I., Inc. filed Critical San-Ei Gen F.F.I., Inc.
Priority to JP2008508637A priority Critical patent/JPWO2007114304A1/ja
Publication of WO2007114304A1 publication Critical patent/WO2007114304A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, 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
    • A23L21/00—Marmalades, jams, jellies or the like; Products from apiculture; Preparation or treatment thereof
    • A23L21/10—Marmalades; Jams; Jellies; Other similar fruit or vegetable compositions; Simulated fruit products
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, 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
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
    • A23L5/27—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
    • A61K36/736—Prunus, e.g. plum, cherry, peach, apricot or almond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants

Definitions

  • the present invention relates to a benzene production inhibitor and a benzene production inhibition method. More specifically, the present invention relates to a benzene production inhibitor and a benzene production inhibition method capable of significantly suppressing benzene produced by benzoic acid and its derivative power.
  • benzoic acid and its salts have been used as preservatives in various products such as foods, beverages, cosmetics and pharmaceuticals in order to improve the preservability of the materials themselves or the materials contained therein.
  • Non-Patent Document 1 J Agr Food Chem. (1993), 41 (5): 693-695
  • An object of the present invention is to provide a benzene production inhibitor and a benzene production inhibition method capable of significantly suppressing benzene production caused by benzoic acid as a causative substance.
  • the present invention relates to a benzene formation inhibitor that is highly safe and water-soluble and can be suitably used for foods, etc.
  • Another object of the present invention is to provide a method for suppressing benzene production that is widely used in many products. Means for solving the problem
  • the inventors of the present invention have made extensive studies in order to solve the above-mentioned problems. As a result, the flavonol and its glycoside have an action of significantly suppressing benzene production caused by benzoic acids. I found something.
  • the present invention has been completed on the basis of strong knowledge and includes the following embodiments.
  • a benzene production inhibitor comprising as an active ingredient at least one selected from the group power of flavonol and flavonol glycoside strength.
  • the ratio of the total amount of ascorbic acid, ascorbate, ester compound of ascorbic acid and ascorbic acid glycoside to 100 parts by weight of the total amount of flavonol and flavonol glycoside is 1 to: L00000
  • a benzene formation inhibitor used for a benzoic acid-containing composition wherein flavonol is based on 100 parts by weight of the total amount of benzoic acid converted to benzoic acid in the composition
  • a benzene formation inhibitor of a benzoic acid-containing composition characterized in that the benzene formation inhibitor described in any of (1-1) to (1-10) is added to the benzoic acid-containing composition. Control method.
  • the benzoic acid-containing composition is a composition containing at least one selected from benzoic acid, a salt of benzoic acid, a benzoic acid ester, and a group strength of these hydroxyl compounds, (2) The method for inhibiting benzene production as described in -1).
  • the benzoic acid-containing composition contains benzoic acids in a total amount of 1 to 2500 ppm in terms of the amount of benzoic acid (2-1) or (2-2) The method for suppressing benzene formation described in 1.
  • a benzene formation inhibitor is added to the benzoic acid-containing composition in such a ratio that the total amount of flavonol and flavonol glycoside is 0.1 to LOOOOppm. The method for suppressing benzene production described in 2-3).
  • the total amount of flavonol and flavonol glycoside added to the benzoic acid-containing composition is 100 parts by weight in terms of the total amount of benzoic acid of the benzoic acid in the composition.
  • (3-1) A benzoic acid-containing composition containing the benzene formation inhibitor according to any one of (1-1) to (1-10).
  • the benzoic acid-containing composition is a composition containing at least one selected from benzoic acid, a salt of benzoic acid, a benzoic acid ester, and a group strength of these hydroxyl strengths.
  • the benzoic acid containing composition as described in (3-1).
  • the benzoic acid-containing composition contains benzoic acids in a total amount of 1 to 2500 ppm in terms of the amount of benzoic acid (3-1) or (3-2) A benzoic acid-containing composition described in 1.
  • the benzoic acid-containing composition contains a benzene formation inhibitor in a ratio such that the total amount of flavonol and flavonol glycoside is 0.1 to LOOOOppm. 3-3
  • Flavonol and flavonol glycoside strength Group power at least one selected
  • composition containing at least one selected from ascorbic acid, ascorbate, an ester compound of ascorbic acid, and ascorbic acid glycoside strength for use in the production of a benzene formation inhibitor.
  • the invention's effect it is possible to provide a method for significantly suppressing benzene production from benzoic acids caused by light irradiation, heat, and the like, and a benzene production inhibitor that can be easily used in the method.
  • the benzene production inhibitor and the benzene production inhibition method of the present invention it is possible to significantly suppress the production of benzene produced gradually from benzoic acids at each stage of production, distribution, and storage period, and to stabilize for a long time. The quality and safety of benzoic acid-containing products can be maintained.
  • the benzene production inhibitor of the present invention is characterized by containing at least one selected from flavonol and a group force consisting of flavonol glycosides as an active ingredient.
  • flavonols and flavonol glycosides are also collectively referred to as “flavonols”.
  • Examples of the flavonols used in the present invention include compounds having a hydroxyl group at the 3-position of flavonoids, and examples of flavonol glycosides include glycosides having the flavonol in the aglycone moiety.
  • flavonols specifically quercetin, kenferol, rhamnetin, gosipetin, myricetin, morin, and isorhamnetin
  • flavonol glycosides specifically quercitrin, hyperoside, rutin, isoquacitrin.
  • myricitrin and those subjected to various treatments such as enzyme treatment or hydrolysis (for example, enzyme-treated rutin and enzyme-treated isoquercitrin) can be exemplified. Note that these may be purified or crudely purified regardless of whether or not they are purified. Preferred are rutin, taercetin, isoquercitrin, enzyme-treated rutin, myristitrine and enzyme-treated isoquercitrin, more preferably rutin, myristitrine, enzyme-treated rutin and enzyme-treated isoquercitrin, and more preferably myristitrin. And enzyme-treated isoquercitrin. These flavonols may be used alone or in any combination of two or more.
  • a plant extract containing the various flavonols listed above can be used as it is, instead of the flavonols themselves or together with the flavonols themselves.
  • Yenju extract Yenju buds or flower extraction
  • Examples of the present invention include: extracts), tartary buckwheat extract, dokudami extract, bayberry extract, buckwheat whole plant extract, red bean whole plant extract, onion extract, and rabu hemp extract.
  • Such a plant extract can be obtained by extracting a corresponding part of a plant containing a relatively large amount of flavonols with water, alcohol or other organic solvent, and can be used as it is. Furthermore, it can also be used after enzymatic treatment.
  • Examples of plant extracts containing flavonols preferably used in the present invention include red bean whole plant extract, engju extract, buckwheat whole plant extract, and bayberry extract. Particularly preferred are the bayberry extract and ngeju extract, and more preferably the bayberry extract.
  • These plant extracts contain effective components of flavonol and flavonol glycoside, respectively. Specifically, it is rutin for Yenju extract, rutin and quercetin for tartary buckwheat extract, quercitrin and isoquercitrin for dokudami extract, myricitrin for bayberry extract, and whole plant extract for buckwheat. Rutin, red bean whole herb extract contains rutin, onion extract is quercetin, and rabu extract contains isoquercitrin and noy peroside as the main components of flavonols.
  • Enzyme-treated isoquercitrin is obtained by acting a glycosyltransferase on isoquercitrin in the presence of a sugar donor, and is expressed to various extents with isoquercitrin represented by the following formula. This refers to a mixture with darcosylated diarcosyl isoquercitrin.
  • G I G represents a glucose residue
  • n represents 0 or an integer of 1 or more
  • “enzyme-treated isoquercitrin” is an isoquercitrin in which the number of ⁇ - 1,4-bonded glucose residues ( ⁇ ) is 0, and a glucose residue of «-1,4-bonded A mixture with a-darcosylisoquercitrin having a number ( ⁇ ) of 1 or more, usually 1 to 15, preferably 1 to 10. It is a compound.
  • n 1 or more).
  • the enzyme-treated isoquercitrin used in the present invention may be a mixture of various enzyme-treated isoquercitrins having different glucose group binding numbers (n). Even a kind of enzyme-treated isoquercitrin that is single! / ,.
  • Powerful enzyme-treated isoquercitrin can be prepared by treating isoquercitrin with glucose transferase.
  • enzyme-treated isoquercitrin is usually obtained by glycosylation using a glucose residue transferase such as darcosidase or transdalcosidase, by transferring equimolar amounts of glucose residues to isoquercitrin. Can be manufactured.
  • the glucose source used in the case of glycosylation is not limited as long as it can be transferred to one molecule of S-isoquercitrin with one or more glucose residues.
  • glucose, maltose, amylose Amylopectin, starch, starch liquefied product, starch syrup, cyclodextrin, and the like can be used.
  • the amount of glucose source used is usually 0.1 to 20 parts by weight, preferably 0.5 to 15 parts by weight, more preferably 1 to: LO part by weight, based on 1 part by weight of isoquercitrin present in the reaction system. Can be mentioned.
  • darcosidase for example, at-amylase (EC 3.2.1.1), a-darcosidase (EC 3.2.1.20) and the like can be used, and as the trans dalcosidase, for example, cyclodextrin glucanotransferase (EC 2.4.1.19) (hereinafter abbreviated as CGTase).
  • CGTase cyclodextrin glucanotransferase
  • CGTase is produced by bacteria such as Bacillus circulans, Bacillus macerans, Bacillus stearothermophilus, Bacillus megaterium, Bacillus polymixer and other Bacillus spp. Any of these can be used freely in the present invention.
  • glucose residue transferases are commercially available enzymes, and it is convenient to use commercially available enzyme agents (for example, trade name: Contizym manufactured by Amano Enzym Co., Ltd.). You can also.
  • the enzyme is a crude product that does not necessarily have to be purified. There may be.
  • the glucose residue transfer enzyme-producing bacterium is inoculated in a medium containing isoquercitrin, and the enzyme-treated isoquercitrin is produced by a reaction by fermentation, and the glucose residue A transferase or glucose residue transferase-producing bacterium may be immobilized and reacted with isoquercitrin in a batch or continuous manner to produce enzyme-treated isoquercitrin.
  • Glucose residue transferase can be performed using each of darcosidase and transdalcosidase alone, or can be used in combination (simultaneously or sequentially).
  • the reaction conditions of the glucose residue transferase may be any conditions under which the glucose residue transferase acts in a mixed water system of isoquercitrin, glucose residue transferase and the above glucose source.
  • the amount of glucose residue transferase used is 1 part by weight of isoquercitrin.
  • the enzyme specific activity is about 100 units (1 mg of j8-cyclodextrin is produced per minute from soluble starch). Enzyme amount is defined as 1 unit)] It can be appropriately selected from the range of 0.001 to 20 parts by weight. Preferably, it is about 0.005: LO part by weight, more preferably about 0.01-5 part by weight.
  • the amount of isoquercitrin in the reaction system is not particularly limited! However, for the purpose of efficiently carrying out glycosylation, it is usually 0.1 to 30% in 100% by weight of the reaction system. %, Preferably 0.5 to 20% by weight, more preferably 1 to 10% by weight.
  • the temperature of the reaction system can be selected by appropriately selecting a range of about 80 ° C or less, which varies depending on the type of enzyme used. Within this range, industrially advantageous is about 20-80 ° C, preferably about 40-75 ° C.
  • the pH condition is usually pH 3 to: about L 1 or less, preferably pH 4 to 8.
  • the reaction can be performed while standing or stirring or shaking.
  • an anti-oxidation agent such as ascorbic acid that replaces the head space of the reaction system with an inert gas such as nitrogen. is there.
  • the glucose group binds to the glucose residue of isoquercitrin to produce the target enzyme-treated isoquercitrin.
  • the number of glucose groups bound to the glucose residue of isoquercitrin (the number of n in the above formula (1)) is not particularly limited, but is usually 1 to 15, preferably as described above. Can be arbitrarily adjusted to be in the range of 1 to: LO. Examples of powerful adjustment methods include a method in which various amylases—amylase, j8 amylase, dalcoamylase, a-darcosidase, maltase, etc.) are used alone or in combination after the enzyme-treated isoquercitrin is produced. . By doing so, the number of glucose sugar chains in the enzyme-treated isoquercitrin molecule obtained by the above-described method can be reduced to obtain enzyme-treated isoquercitrin having an arbitrary glucose sugar chain length.
  • the method for isolating and purifying the enzyme-treated isoquercitrin is not particularly limited.
  • an isolation method there can be mentioned a method of isolation using gel filtration resin in a conventional manner.
  • the purification of the enzyme-treated isoquercitrin is not particularly limited, and can be carried out by arbitrarily combining conventional methods.
  • various resin treatment methods adsorption method, ion exchange method, gel filtration method, etc.
  • membrane treatment method ultrafiltration membrane treatment method, reverse osmosis membrane treatment method, ion exchange membrane treatment method, zeta potential membrane treatment method, etc.
  • electrodialysis method salting out, acid precipitation, recrystallization, solvent fractionation method, activated carbon treatment method and the like.
  • the enzyme-treated isoquercitrin thus obtained is obtained by further combining equimolar amounts of glucose with the glucose residue of isoquercitrin (quercetin 3-0 monodarcoside).
  • -It is mainly composed of darcosyl isoquercitrin and is readily soluble in water.
  • Enzyme-treated rutin was obtained by adding glucose to ⁇ -1 and 4 of rutin with a mixture of rutin and starch or dextrin using cyclodextrin lucanotransferase.
  • the main component is ⁇ -darcosylrutin.
  • Pulid extract refers to a process of filing a linguaceous plant, for example, a patent application by the present applicant.
  • the bayberry extract obtained by such an operation contains a large amount of myricitrin (myricetin-3- ⁇ rhamnoside), which is a flavonol glycoside, and serves as a source of the glycoside. Moreover, this bayberry extract can be used as it is. Furthermore, it can be subjected to a glycosyltransferase treatment according to the method described in JP-A-9-95672, and this can be used as a readily water-soluble bayberry extract. Can do.
  • the proportion of flavonols contained in the benzene production inhibitor is not particularly limited as long as it has an effect of inhibiting the production of benzene by benzoic acid.
  • Ben Examples of the ratio of flavonols in 100% by weight of the Zen formation inhibitor include 0.1 to L00% by weight, preferably 0.5 to 80% by weight.
  • the benzene production inhibitor of the present invention may also contain ascorbic acid, ascorbate, an ester compound of ascorbic acid, or an ascorbic acid glycoside.
  • ascorbic acid, ascorbic acid salt, ascorbic acid ester compound and ascorbic acid glycoside are also collectively referred to as “ascorbic acids”.
  • L-ascorbic acid L-ascorbic acid, and as a salt of L-ascorbic acid, alkali metal salts such as sodium and potassium of L-ascorbic acid can be preferably mentioned.
  • alkali metal salts such as sodium and potassium of L-ascorbic acid
  • As an ester compound of ascorbic acid ascorbic acid stearic acid ester or ascorbic acid palmitic acid ester can be preferably mentioned, and as an ascorbic acid glycoside, L-ascorbic acid 2-darcoside is preferably mentioned. It is out.
  • the ascorbic acid instead of the ascorbic acid itself or together with the ascorbic acid, for example, lemon, tangerine, navel orange, grapefruit, acerola, strawberry, oyster, kiwifruit, guava, papaya and camcam Fruits such as Cabbage, Komatsuna, Chingensai, Togan, Parsley, Peppers (Red Peppers), Morohaya, and Lotus roots; Root vegetables such as Sweet Potato Potato; and Liver (Chicken, Pig, Cow)
  • a food material containing ascorbic acid can also be used.
  • the mixing ratio of both is not limited, but the ratio of ascorbic acids (total) to 100 parts by weight of flavonols (total) is usually 1 to: L00000 weight Parts, preferably 1 to 50000 parts by weight, more preferably 2 to 30000 parts by weight.
  • the benzene formation inhibitor of the present invention is not particularly limited as long as it contains any of the above-mentioned flavonols, or other components as long as it contains ascorbic acids in addition to the flavonols. May be blended.
  • the strong carrier is not particularly limited as long as it does not interfere with the effect of the present invention.
  • sucrose, glucose, dextrin, starches, cyclodextrin, trehalose Sugars such as lactose, maltose, starch syrup and liquid sugar; alcohols such as ethanol, propylene glycol and glycerin; sugar alcohols such as sorbitol, mannitol, xylitol, erythritol and maltitol; gum arabic, xanthan gum, carrageenan and guaga And polysaccharides such as mud and dielan gum; or water.
  • flavonols are poorly water-soluble and difficult to handle. Therefore, if necessary, flavonols may be dissolved in lower alcohols such as ethanol or polyhydric alcohols such as glycerin and propylene glycol. It may be used.
  • lower alcohols such as ethanol or polyhydric alcohols such as glycerin and propylene glycol. It may be used.
  • additives include auxiliary agents such as antioxidants and chelating agents, fragrances, spice extracts, preservatives, and the like.
  • examples of the antioxidant used as an additive include those widely used as food additives.
  • erythorbic acids such as erythorbic acid and its salts (for example, sodium erythorbate); chlorogenic acids such as chlorogenic acid, isocortic acid and its salts; sodium sulfite, sodium hyposulfite, sodium pyrosulfite or Sulphites such as potassium pyrosulfite; a-tocopherols and tocopherols such as mixed tocopherols; dibutylhydroxytoluene (BHT) butylhydroxydisole (BHA) and the like; ethylenediamin tetracalcium disodium and ethylenediamin tetraacetate disodium Ethylenediamine amine acetic acid such as gallic acid such as gallic acid and propyl gallate; y oryzanol, ellagic acid, guayata fat, sesamolin
  • the form of the benzene production inhibitor of the present invention is not particularly limited.
  • it is a solid such as powder, granule or tablet; a liquid such as liquid or emulsion; or a paste It can be prepared in any form, such as semi-solid.
  • the benzene production inhibitor of the present invention can be widely applied to compositions containing benzoic acids for the purpose of inhibiting benzoic acid benzene production.
  • Such compositions include foods and drinks, cosmetics, pharmaceuticals, quasi drugs, and feeds.
  • these forms are not particularly limited, those containing water as a preferred form, in particular, liquids such as beverages, skin lotions, cosmetic liquids, liquids, drinks, injections and infusions, especially aqueous solutions. Things can be mentioned.
  • benzoic acid examples include benzoic acid, benzoate, benzoate ester, and hydroxyl groups thereof.
  • benzoic acid salts include alkali metal salts of benzoic acid such as sodium and potassium; alkaline earth metal salts of benzoic acid such as calcium and magnesium.
  • Benzoic acid esters include methyl benzoate, ethyl benzoate, butyl benzoate, propyl benzoate, and benzyl benzoate.
  • Hydroxy compounds include isoptil parahydroxybenzoate, isopropyl benzoate, parahydroxy benzoate, and parahydroxy benzoate. Examples include ethyl benzoate, butyl parahydroxybenzoate, and propyl parahydroxybenzoate.
  • the benzene production inhibitor of the present invention is a product to which the above benzoic acid is added for the purpose of, for example, preserving or preserving the stability of the product, or a product originally derived from the raw material and containing the benzoic acid.
  • benzoic acid By adding and blending with benzoic acid, it is possible to suppress the formation of benzoic acid-like benzene in the product.
  • the benzene formation inhibitor of the present invention is used by adding it to a composition containing benzoic acids.
  • the total amount converted to the amount of benzoic acid of the benzoic acids in the composition is 100% by weight.
  • benzene formation of benzoic acid in the product may occur by light irradiation or heating at each stage of production, distribution, and storage period.
  • the benzene formation inhibitor of the present invention particularly light The production of benzene by irradiation can be significantly suppressed.
  • the present invention provides a benzoic acid-containing composition containing the aforementioned flavonols, or flavonols and ascorbic acid as a benzene formation inhibitor.
  • the benzoic acid-containing composition has the effect that the production of benzene caused by benzoic acids is significantly suppressed by containing flavonols, or flavonols and ascorbic acids.
  • the benzoic acid-containing composition means a composition containing at least one benzoic acid such as benzoic acid, benzoic acid salt, benzoic acid ester and hydroxyl group thereof described above.
  • Benzoic acid compositions include not only compositions (products) with artificially added benzoic acids for the purpose of preservation (preservation), but also spices such as cinnamon, thyme or fennel; leek, large leaves, broccoli or Vegetables such as shiitake mushrooms; also includes compositions (products) containing benzoic acids derived from ingredients originally contained in the materials used in the preparation of the composition, such as benzoin (benzoic acid), a fragrance base material It is.
  • the amount of benzoic acid contained in the powerful benzoic acid-containing composition is not limited! However, in terms of the ratio of benzoic acid, usually 1 to 2500 ppm, preferably 1 to L000 ppm, more preferably 1 to 600 ppm.
  • Examples of the benzoic acid-containing composition include products that can be applied to human animals and can be taken into the living body, particularly foods and drinks, cosmetics, pharmaceuticals, quasi drugs, and feeds. Preferably it is food and drink. Preferably as beverages, particularly soft drinks; preferably as cosmetics, lotions and emulsions; preferably as quasi-drugs, drinks, gargles, mouth washes, liquid polishes, eyewashes; and preferably as pharmaceuticals Drink, liquid medicine, sciroc Examples include products containing water, such as eye drops, eye drops, injections, and infusions.
  • the food and drink targeted by the present invention are those that have benzoic acids added for the purpose of storage or the like, or those that have benzoic acids derived from ingredients originally contained in the material.
  • Processed products Fish ham, fish sausage, fish surimi, salmon, bamboo rings, hampen, fried satsuma, Date roll, whale bacon, etc .; dairy and fat products such as butter, margarine, cheese, whipped cream; udon, Cold wheat, somen, buckwheat, Chinese noodles, spaghetti, macaroni, rice noodles, harsame and wonton, and other processed foods, and various prepared foods such as various side dishes and rice cakes and rice fields. Beverages and confectionery are preferred.
  • the food and drink of the present invention is formulated with the benzene formation inhibitor of the present invention in any step of production. Except for this, it can be produced according to conventional production methods for various foods and drinks. Although there are no particular restrictions on the blending method and order of the benzene formation inhibitor, it is preferable to add the benzene formation inhibitor at the beginning of the production process. Preferably, when adding benzoic acid, a benzene formation inhibitor may be added before being exposed to a force or heat treatment step in which the benzene formation inhibitor of the present invention is contained or exposed to light.
  • Skin care cosmetics containing benzoic acids (lotions (skin lotions), milky lotions, creams, etc.), lipsticks, sunscreen cosmetics, makeup cosmetics, etc. as cosmetics targeted by the present invention; benzoic acids as pharmaceuticals Tablets, capsules, drinks, troches, gargles, eye drops, injections, drops, etc .; quasi-drugs containing benzoic acids (particularly liquid brushes), mouthwashes, Examples include mouth fresheners, bad breath prevention agents, eyewashes, etc .; examples of feeds include cat foods containing benzoic acids, dog foods and other pet foods, food for ornamental fish and farmed fish, etc. It is not something.
  • benzoic acid-containing compositions such as cosmetics, pharmaceuticals, quasi-drugs, and feeds, except that the benzene formation inhibitor of the present invention is blended in any step of their production, It can be produced according to conventional methods for various products. There is no particular restriction on the timing of the benzene formation inhibitor in cosmetics, pharmaceuticals, quasi drugs or feeds. 1S It is desirable to combine with various materials at the beginning of the manufacturing process, preferably before the heat treatment process or before exposure to light. .
  • the amount of the benzene formation inhibitor of the present invention added to various benzoic acid-containing compositions is such an amount that the production of benzoic acid benzene can be suppressed.
  • the content of benzoic acids contained in each composition (product) can be appropriately selected and determined in consideration of the type of the object 'application and the components contained therein. For example, it is sufficient if the benzoic acid-containing composition is added to the benzoic acid-containing composition so that the total amount of flavonols is contained at a ratio of at least 0.1 ppm.
  • the total amount of flavonols is preferably 1 to: LOOOOppm, more preferably 1 to 5000ppm. More preferably, in the benzoic acid-containing composition, the benzene formation inhibitor is at least 0. lp as the total amount of flavonols. pm, preferably 1 to: can be included at a ratio of LOOOppm
  • the total amount of flavonol and flavonol glycoside is preferably 1 to L00000 parts by weight with respect to 100 parts by weight of the total amount of benzoic acid converted to the amount of benzoic acid contained in the benzoic acid-containing composition. More preferably, the benzene production inhibitor may be added at a ratio of 1 to 50000 parts by weight, more preferably 1 to 10 000 parts by weight.
  • the ratio of ascorbic acids (total amount) to 100 parts by weight of flavonols (total amount) in the benzoic acid-containing composition is usually 1 to L00000 parts by weight, preferably 1 to 5000 parts by weight. More preferably, it is added by adding a benzene production inhibitor so as to be 2 to 30000 parts by weight.
  • this invention provides the benzene production
  • the benzoic acid-containing composition targeted by the present invention is derived from a composition obtained by artificially adding benzoic acid for the purpose of storage or the like, or a component originally contained in the material to be used. If it is a composition which has benzoic acid, there will be no restriction
  • the method of the present invention can be carried out by allowing these benzoic acid-containing compositions to coexist with the benzene production inhibitor of the present invention.
  • the coexistence mode is not particularly limited as long as a state in which both are in contact with each other is formed.
  • a powerful coexistence state can be formed by blending the benzoic acid-containing composition with the benzene production inhibitor of the present invention.
  • the coexistence state can be formed by blending the benzene formation inhibitor of the present invention as one of the material components during the production of the food or drink.
  • the same applies to other products such as cosmetics, pharmaceuticals, quasi drugs, and feeds.
  • the use ratio of the benzene formation inhibitor of the present invention relative to the benzoic acid-containing composition is not particularly limited as long as the effect of the present invention is exhibited, and is appropriately determined according to the type of the target composition. Can be adjusted.
  • the benzoic acid-containing The blending ratio of the benzene formation inhibitor to the composition may be at least 0.1 ppm, preferably 1 to: LOOOOppm, more preferably 1 to 5000 ppm in terms of the total amount of flavonols.
  • a ratio of at least 0.1 ppm, preferably 1 to: LOOOppm in terms of the total amount of flavonols can be mentioned.
  • the total amount of flavonols and flavonol glycosides is preferably 1 to 100 000 wt.% With respect to 100 parts by weight of the total amount of benzoic acid converted to the amount of benzoic acid contained in the benzoic acid-containing composition. 1 to 50000 wt.%, More preferably 1 to: A benzene formation inhibitor may be added at a ratio of L0000 wt.
  • the ratio of ascorbic acid (total amount) to 100 parts by weight of flavonols (total amount) in the benzoic acid-containing composition is usually 1 to: L00000 parts by weight, preferably 1 to 50000 parts by weight.
  • Benzene production inhibitor can be blended with the amount of parts, more preferably 2 to 30000 parts by weight as a guide.
  • the production of benzene caused by benzoic acids in the benzoic acid-containing composition is significantly suppressed, and the mixture of benzene in the composition is prevented. be able to.
  • the bayberry extract, rutin, enzyme-treated isoquer citrin (hereinafter referred to as EMIQ), and enzyme-treated rutin used those prepared in Preparation Example 1, Preparation Example 2, Preparation Example 3, and Preparation Example 4, respectively. .
  • the prepared bayberry peach extract contained 98.2% by weight of myricitrin.
  • the molar composition ratio (%) of enzyme-treated isoquercitrin (EMIQ) is shown below.
  • the molar composition ratio is a composition ratio converted from isoquercitrin (hereinafter referred to as IQC) to IQC and Glc7 in which seven glucoses are bound to IQC by seven ⁇ -1,4 bonds as 100%. is there.
  • IQC isoquercitrin
  • Glc7 in which seven glucoses are bound to IQC by seven ⁇ -1,4 bonds as 100%. is there.
  • Table 1 such as “IQC + Glcl”, the number after “Glc” means the number of glucose ⁇ -1,4 linked to isoquercitrin.
  • IQC + Glcl is ⁇ -darcosyl isoquercitrin in which glucose is bonded to isoquercitrin by one ⁇ -1,4 bond
  • IQC + Glc7 is isoquercitrin.
  • EMIQ contained trace amounts of IQC bound to 8 or more IQCs (IQC + Glc8 or more).
  • IQC Isoquercitrin G l c l ⁇ G l c 7: I Number of glucose additions to QC
  • the obtained enzyme-treated rutin was subjected to HPLC analysis under the following conditions to calculate the molar ratio (%) of various a-darcosylrutin contained in the enzyme-treated rutin.
  • Table 2 shows the molar composition ratio (%) of the enzyme-treated rutin.
  • the molar composition ratio is a composition ratio converted to 100% of rutin (RTN) and the total of 8 components in which 1-7 glucose is bonded to rutin with ⁇ -1,4 bonds.
  • RTN + GlclJ is ⁇ -darcosylrutin in which one glucose is bound to rutin by ⁇ -1,4 bonds
  • RTN + Glc7 is rutin having glucose ⁇ -1,4 It means 7 ⁇ -darcosyl rutins linked together.
  • the enzyme-treated rutin contained a trace amount of rutin combined with 8 or more glucoses (RTN + Glc8 or more).
  • RTN Rutin Glc 1 to Glc 7: Number of glucose additions to RTN
  • the light irradiation test beverages prepared above (Prescription Examples 1 to 6) were irradiated with light using a feed meter under the following conditions.
  • the beverage of Formulation Example 1 containing sodium benzoate had a benzene content that increased over time due to light irradiation.
  • This beverage was supplemented with EMIQ bayberry extract ( The benzene content of formulas 2 and 3) is extremely low. It was found that EMIQ and bayberry extract have the effect of suppressing benzene formation caused by sodium benzoate.
  • the results of Formulation Example 4 indicate that ascorbic acid also has an effect of suppressing benzene formation caused by sodium benzoate. By further using EMIQ bayberry extract together with this, further benzene production can be achieved. Can be suppressed.
  • test beverage after light irradiation was treated to recover the organic layer, and subjected to GCZMS under the following conditions to measure the benzene content.
  • Trisodium citrate (adjusted to pH 3.0)
  • the heat abuse test beverages prepared above (Prescription Examples 23 to 25) were stored under the following high temperature conditions and subjected to a heat abuse test.
  • Constant temperature machine EYELA WINDY OVEN WFO- 600D
  • test beverage after the thermal abuse test was treated in the same manner as in Experimental Example 1 to recover the organic layer, and subjected to GCZMS under the same conditions as in Experimental Example 2 to measure the benzene content.
  • a 300 mL separatory funnel 200 mL of test beverage after light irradiation and n-heptane (for high-speed liquid cupmatographs, Wako Pure Chemical Industries) lOmL are placed in a shaker (KM-SHAKER: made by IWAKI). Set and shake for 5 minutes. After standing for 10 minutes, the organic layer was recovered and subjected to GCZMS under the following conditions to measure the benzene content.
  • KM-SHAKER made by IWAKI
  • ascorbic acid was also found to have an effect of suppressing benzene formation caused by sodium benzoate, but by further using flavonols in combination, It was possible to further suppress the formation of benzene.
  • ingredients other than fruit juice and fragrance are added to ion-exchanged water, heated and stirred to 90 ° C, mixed with fruit juice and fragrance, mixed and stirred, then filled into a container and cooled. A drink with lemon juice was obtained. The resulting beverage was able to significantly suppress benzene formation compared to the comparative beverage without the addition of flavonols.
  • Example 2 Acid, Beverage
  • Nicotinic acid amide 0. 0 1
  • Example 9 Lime syrup (for dilution)
  • Example 10 Pong Of the formulation examples listed in Table 30 below, raw materials other than fruit juice, fragrance, and vinegar were mixed in ion-exchanged water and dissolved by heating until the temperature reached 80 ° C. Next, fruit juice, fragrance, and vinegar were added thereto, dissolved by stirring, filled into a container, and then cooled to obtain ponzu. The obtained ponzu vinegar was able to remarkably suppress benzene formation as compared with the comparative beverage with the strength of adding flavonols.
  • Component 1 was added to Component 16, and heated and stirred at 80 ° C for 10 minutes. Ingredients 2-11 were added and dissolved by stirring, cooled to 60 ° C or lower, and ingredients 12 and 13 were added and stirred. Further, Component 14 was added little by little, and emulsification was performed with a homomixer. Component 15 was added and mixed thereto, and the mixture was filled in a container to obtain a Thousand Island dressing. The obtained dressing was able to remarkably suppress the production of benzene as compared with the comparative drink with the addition of flavonols.
  • ingredients 1 to 7 are added to ingredient 16 and dissolved by heating, and kept at 70 ° C.
  • ingredients 8 to 15 are mixed and heated to dissolve at 70 ° C.
  • the product kept in the water was preliminarily emulsified and uniformly emulsified with a homomixer. This was cooled with stirring to obtain an emulsion.
  • the obtained emulsion was able to remarkably suppress the production of benzene as compared with the comparative beverage to which no flavonols were added.
  • the benzene production inhibitor of the present invention can significantly inhibit the production of benzene by heat or light in products containing benzoic acids such as benzoic acid, salts thereof or esters thereof.
  • benzoic acids such as benzoic acid, salts thereof or esters thereof.
  • beverages and the like are often sold while being packaged in transparent containers such as PET bottles.
  • the present invention is a product to which benzoic acids are added for the purpose of preserving and preserving the product, such as antiseptics. It is possible to suppress the formation of benzene in the product (the product containing benzoic acid), and as a result, it is possible to provide a product that stably maintains quality and safety for a long period of time.

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Abstract

La présente invention concerne un inhibiteur de production de benzène capable d'inhiber la production de benzène nocif par un produit renfermant de l'acide benzoïque et qui n'est pas nuisible pour l'organisme humain. L'inhibiteur contient du flavonol et/ou un glycoside de ce composé, ou une combinaison de flavonol et/ou d'un de ses glycosides avec de l'acide ascorbique et un sel, un composé estérifié ou un glycoside de celui-ci, à titre de principe actif. Lorsqu'on laisse une composition contenant de l'acide benzoïque coexister avec l'inhibiteur, il est possible d'empêcher la production de benzène à partir de l'acide benzoïque présent dans la composition.
PCT/JP2007/056996 2006-03-29 2007-03-29 Inhibiteur de production de benzène et procédé d'inhibition de production de benzène WO2007114304A1 (fr)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008112854A1 (fr) * 2007-03-15 2008-09-18 The Coca-Cola Company Procédés pour inhiber la formation de benzène dans les boissons et boissons produites ainsi
WO2009075377A1 (fr) * 2007-12-13 2009-06-18 Mizkan Group Corporation Assaisonnement liquide en récipient de stockage et méthode d'obtention d'une saveur type jus de citron enrichie ou longue en bouche
WO2013047611A1 (fr) * 2011-09-27 2013-04-04 花王株式会社 Boisson emballée
CN105246353A (zh) * 2013-06-03 2016-01-13 雀巢产品技术援助有限公司 具有减少的苯的即饮型茶饮料及其制备方法
EP3685825A1 (fr) * 2019-01-24 2020-07-29 Alps Pharmaceutical Ind. Co., Ltd. Compositions d'isoquercitrine
US10918654B1 (en) 2019-09-23 2021-02-16 Alps Pharmaceutical Ind. Co., Ltd. Rutin compositions
US11110109B2 (en) 2019-10-22 2021-09-07 Alps Pharmaceutical Ind. Co., Ltd. Water soluble O-glycosyl flavonoid compositions and methods for preparing same
US11266671B2 (en) 2018-04-23 2022-03-08 Alps Pharmaceutical Ind. Co., Ltd. Compositions of O-glycosyl flavonoids

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0775536A (ja) * 1993-06-17 1995-03-20 Oomiya Yakugyo Kk ケルセチン配糖体を含有する清涼飲料水

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0775536A (ja) * 1993-06-17 1995-03-20 Oomiya Yakugyo Kk ケルセチン配糖体を含有する清涼飲料水

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
GARDNER L.K. ET AL.: "Benzene production from decarboxylation of benzoic acid in the presence of ascorbic acid and a transition-metal catalyst", J. OF AGRIC. FOOD CHEM., vol. 41, no. 5, 1993, pages 693 - 695, XP003018352 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008112854A1 (fr) * 2007-03-15 2008-09-18 The Coca-Cola Company Procédés pour inhiber la formation de benzène dans les boissons et boissons produites ainsi
WO2009075377A1 (fr) * 2007-12-13 2009-06-18 Mizkan Group Corporation Assaisonnement liquide en récipient de stockage et méthode d'obtention d'une saveur type jus de citron enrichie ou longue en bouche
JP2009142194A (ja) * 2007-12-13 2009-07-02 Mizkan Nakanos:Kk 保存用容器入りの液体調味料、柑橘果汁感を増強または長期間保持する方法
WO2013047611A1 (fr) * 2011-09-27 2013-04-04 花王株式会社 Boisson emballée
JP2013081453A (ja) * 2011-09-27 2013-05-09 Kao Corp 容器詰飲料
CN105246353A (zh) * 2013-06-03 2016-01-13 雀巢产品技术援助有限公司 具有减少的苯的即饮型茶饮料及其制备方法
US10849335B2 (en) 2013-06-03 2020-12-01 Societe Des Produits Nestle S.A. Ready-to-drink tea beverages with reduced benzene and methods for making same
US11266671B2 (en) 2018-04-23 2022-03-08 Alps Pharmaceutical Ind. Co., Ltd. Compositions of O-glycosyl flavonoids
EP3685825A1 (fr) * 2019-01-24 2020-07-29 Alps Pharmaceutical Ind. Co., Ltd. Compositions d'isoquercitrine
US10918654B1 (en) 2019-09-23 2021-02-16 Alps Pharmaceutical Ind. Co., Ltd. Rutin compositions
US11110109B2 (en) 2019-10-22 2021-09-07 Alps Pharmaceutical Ind. Co., Ltd. Water soluble O-glycosyl flavonoid compositions and methods for preparing same

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