HK111196A - Alpha-glycosyl-l-ascorbic acid, and its preparation and uses - Google Patents

Alpha-glycosyl-l-ascorbic acid, and its preparation and uses Download PDF

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Publication number
HK111196A
HK111196A HK111196A HK111196A HK111196A HK 111196 A HK111196 A HK 111196A HK 111196 A HK111196 A HK 111196A HK 111196 A HK111196 A HK 111196A HK 111196 A HK111196 A HK 111196A
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ascorbic acid
alpha
glycosyl
glucosyl
saccharide
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HK111196A
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English (en)
French (fr)
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Yamamoto Itaru
Muto Norio
Miyake Toshio
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Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
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Priority claimed from JP1274518A external-priority patent/JP2926412B2/ja
Application filed by Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo filed Critical Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
Publication of HK111196A publication Critical patent/HK111196A/en

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/82—Acid flavourants
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/16—Preparation of compounds containing saccharide radicals produced by the action of an alpha-1, 6-glucosidase, e.g. amylose, debranched amylopectin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C12P19/58—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound through only acyclic carbon atoms to a non-saccharide heterocyclic ring, e.g. bleomycin, phleomycin
    • 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
    • A61K2800/522—Antioxidants; Radical scavengers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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
    • A61Q19/10—Washing or bathing preparations

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Mycology (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Saccharide Compounds (AREA)

Claims (19)

  1. Alpha-Glycosyl-L-ascorbinsäure, die keine direkte reduzierende Aktivität aufweist und folgende Formel besitzt, wobei n eine ganze Zahl von 0 bis 6 ist.
  2. 2-O-alpha-D-Glucosyl-L-ascorbinsäure nach Anspruch 1, die die folgende Formel besitzt:
  3. Verfahren zur Herstellung einer alpha-Glycosyl-L-ascorbinsäure, die keine direkte reduzierende Aktivität aufweist und die folgende Formel besitzt, wobei n eine ganze Zahl von 1 bis 6 ist, und das Verfahren die Einwirkung eines saccharidübertragenden Enzyms auf eine Lösung, die ein alpha-Glucosylsaccharid und wenigstens 1 Gew./Gew.-% L-Ascorbinsäure enthält, um die alpha-Glycosyl-L-ascorbinsäure zu bilden, wobei die Konzentration des alpha-Glucosylsaccharids 0,5 bis 30-fach höher ist als diejenige der L-Ascorbinsäure und die Gewinnung der alpha-Glycosyl-L-ascorbinsäure umfaßt.
  4. Verfahren nach Anspruch 3, wobei das saccharidübertragende Enzym ein aus der Gruppe Cyklomaltodextringlucanotransferase (EC 2.4.1.19) und alpha-Glucosidase ausgewählter Stoff ist.
  5. Verfahren nach Anspruch 3 oder 4, wobei das alpha-Glucosylsaccharid ein aus der Gruppe Maltooligosaccharid, Stärketeilhydrolysat, verflüssigte Stärke, gelatinierte Stärke, löslich gemachte Stärke und deren Mischungen ausgewählter Stoff ist.
  6. Verfahren nach einem der Ansprüche 3 bis 5, wobei das saccharidübertragende Enzym in einer Menge eingesetzt wird, die die Reaktion innerhalb von 3-80 Stunden beendet.
  7. Verfahren nach einem der Ansprüche 3 bis 6, wobei man das saccharidübertragende Enzym auf die Lösung bei einem pH im Bereich von 3-9 und einer Temperatur im Bereich von 30-80°C einwirken läßt.
  8. Verfahren nach einem der Ansprüche 3 bis 7, wobei die alpha-Glycosyl-L-ascorbinsäure 2-O-alpha-D-Glucosyl-L-ascorbinsäure ist mit der folgenden Formel:
  9. Verfahren nach Anspruch 8, wobei man die Glucoamylase (EC 3.2.1.3) auf die Lösung zusammen mit dem saccharidübertragenden Enzym einwirken läßt.
  10. Lebensmittelzusammensetzung, die eine alpha-Glycosyl-L-ascorbinsäure enthält, welche keine direkte reduzierende Aktivität "aufweist und welche die folgende Formel besitzt, wobei n eine ganze Zahl von 0 bis 6 ist.
  11. Lebensmittelzusammensetzung nach Anspruch 10, wobei der Gehalt an alpha-Glycosyl-L-ascorbinsäure wenigstens 0,001 Gew./Gew.-% beträgt.
  12. Lebensmittelzusammensetzung nach Anspruch 10 oder Anspruch 11, wobei die alpha-Glycosyl-L-ascorbinsäure 2-O-alpha-D-Glucosyl-L-ascorbinsäure ist mit folgender Formel:
  13. Lebensmittelzusammensetzung nach einem der Ansprüche 10 bis 12, wobei die alpha-Glycosyl-L-ascorbinsäure nach dem Verfahren des Anspruchs 3 erhältlich ist.
  14. Pharmazeutische Zusammensetzung für rezeptive Krankheiten, die zusammen mit einem pharmazeutisch verträglichen Träger eine alpha-Glycosyl-L-ascorbinsäure als wirksamen Bestandteil enthalten, wobei die alpha-Glycosyl-L-ascorbinsäure die folgende Formel besitzt, wobei n eine ganze Zahl von 0 bis 6 ist.
  15. Pharmazeutische Zusammensetzung nach Anspruch 14, wobei die alpha-Glycosyl-L-ascorbinsäure 2-O-alpha-D-Glucosyl-L-ascorbinsäure ist mit der folgenden Formel:
  16. Pharmazeutische Zusammensetzung nach Anspruch 14 oder Anspruch 15, wobei die alpha-Glycosyl-L-ascorbinsäure nach dem Verfahren des Anspruchs 3 erhältlich ist.
  17. Kosmetische Zusammensetzung, die als wirksamen Bestandteil alpha-Glycosyl-L-ascorbinsäure enthält, welche keine direkte reduzierende Aktivität aufweist und folgende Formel besitzt, wobei n eine ganze Zahl von 0 bis 6 ist.
  18. Kosmetische Zusammensetzung nach Anspruch 17, wobei die alpha-Glycosyl-L-ascorbinsäure 2-O-alpha-D-Glucosyl-L-ascorbinsäure ist mit der folgenden Formel:
  19. Kosmetische Zusammensetzung nach Anspruch 17 oder Anspruch 18, wobei die alpha-Glycosyl-L-ascorbinsäure nach dem Verfahren des Anspruchs 3 erhältlich ist.
HK111196A 1989-05-19 1996-06-27 Alpha-glycosyl-l-ascorbic acid, and its preparation and uses HK111196A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP12707289 1989-05-19
JP1274518A JP2926412B2 (ja) 1989-05-19 1989-10-20 α―グリコシル―Ｌ―アスコルビン酸とその製造方法並びに用途

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HK111196A true HK111196A (en) 1996-07-05

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US (3) US5137723A (de)
EP (1) EP0398484B1 (de)
AT (1) ATE123306T1 (de)
DE (1) DE69019779T2 (de)
DK (1) DK0398484T3 (de)
ES (1) ES2075148T3 (de)
HK (1) HK111196A (de)

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US5767149A (en) 1998-06-16
DE69019779D1 (de) 1995-07-06
ATE123306T1 (de) 1995-06-15
EP0398484B1 (de) 1995-05-31
DK0398484T3 (da) 1995-07-24
DE69019779T2 (de) 1995-12-14
US5137723A (en) 1992-08-11
US5616611A (en) 1997-04-01

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