CH679584A5 - - Google Patents
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- Publication number
- CH679584A5 CH679584A5 CH4063/89A CH406389A CH679584A5 CH 679584 A5 CH679584 A5 CH 679584A5 CH 4063/89 A CH4063/89 A CH 4063/89A CH 406389 A CH406389 A CH 406389A CH 679584 A5 CH679584 A5 CH 679584A5
- Authority
- CH
- Switzerland
- Prior art keywords
- malonate
- genistin
- extracted
- organic solvent
- aqueous
- Prior art date
Links
- 235000010469 Glycine max Nutrition 0.000 claims abstract description 14
- 244000068988 Glycine max Species 0.000 claims abstract description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- FRAUJUKWSKMNJY-UHFFFAOYSA-N 5-hydroxy-3-(4-hydroxyphenyl)-7-(6-malonyl-beta-D-glucopyranosyloxy)-4H-1-benzopyran-4-one Natural products OC1C(O)C(O)C(COC(=O)CC(O)=O)OC1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 FRAUJUKWSKMNJY-UHFFFAOYSA-N 0.000 claims description 19
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N Daidzein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- GMTUGPYJRUMVTC-UHFFFAOYSA-N Daidzin Natural products OC(COc1ccc2C(=O)C(=COc2c1)c3ccc(O)cc3)C(O)C(O)C(O)C=O GMTUGPYJRUMVTC-UHFFFAOYSA-N 0.000 claims description 17
- KYQZWONCHDNPDP-UHFFFAOYSA-N Daidzoside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 KYQZWONCHDNPDP-UHFFFAOYSA-N 0.000 claims description 17
- FRAUJUKWSKMNJY-RSEYPYQYSA-N malonylgenistin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CC(O)=O)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 FRAUJUKWSKMNJY-RSEYPYQYSA-N 0.000 claims description 17
- KYQZWONCHDNPDP-QNDFHXLGSA-N daidzein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 KYQZWONCHDNPDP-QNDFHXLGSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000008346 aqueous phase Substances 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000287 crude extract Substances 0.000 claims description 9
- 239000000284 extract Substances 0.000 claims description 9
- 238000003801 milling Methods 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000004587 chromatography analysis Methods 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- 239000012062 aqueous buffer Substances 0.000 claims description 3
- 239000007853 buffer solution Substances 0.000 claims description 3
- 238000011109 contamination Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 3
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 abstract description 19
- ZCOLJUOHXJRHDI-FZHKGVQDSA-N Genistein 7-O-glucoside Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)c1cc(O)c2C(=O)C(c3ccc(O)cc3)=COc2c1 ZCOLJUOHXJRHDI-FZHKGVQDSA-N 0.000 description 17
- CJPNHKPXZYYCME-UHFFFAOYSA-N Genistin Natural products OCC1OC(Oc2ccc(O)c3OC(=CC(=O)c23)c4ccc(O)cc4)C(O)C(O)C1O CJPNHKPXZYYCME-UHFFFAOYSA-N 0.000 description 17
- YCUNGEJJOMKCGZ-UHFFFAOYSA-N Pallidiflorin Natural products C1=CC(OC)=CC=C1C1=COC2=CC=CC(O)=C2C1=O YCUNGEJJOMKCGZ-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- OENHQHLEOONYIE-UKMVMLAPSA-N beta-Carotene Chemical compound CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- -1 daidzin malonates Chemical class 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000013734 beta-carotene Nutrition 0.000 description 4
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 4
- 239000011648 beta-carotene Substances 0.000 description 4
- 229960002747 betacarotene Drugs 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 4
- 235000008696 isoflavones Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000002515 isoflavone derivatives Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- ISOVWEWRUVBJME-UHFFFAOYSA-N 1,2,3-triphenyltetrazole Chemical class C1=NN(C=2C=CC=CC=2)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 ISOVWEWRUVBJME-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005238 degreasing Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical group CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
- 241000193385 Geobacillus stearothermophilus Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 235000007240 daidzein Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 description 1
- 235000006539 genistein Nutrition 0.000 description 1
- 229940045109 genistein Drugs 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 description 1
- 229930012930 isoflavone derivative Natural products 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
- A23B2/771—Organic compounds containing hetero rings
-
- 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
- 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
-
- 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
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/34—Anti-oxidant compositions; Compositions inhibiting chemical change containing plant or animal materials of unknown composition
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Behavior & Ethology (AREA)
- Food Science & Technology (AREA)
- Zoology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epidemiology (AREA)
- Materials Engineering (AREA)
- Botany (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- General Preparation And Processing Of Foods (AREA)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4063/89A CH679584A5 (en, 2012) | 1989-11-10 | 1989-11-10 | |
| DK90119380.5T DK0426998T3 (da) | 1989-11-10 | 1990-10-10 | Fremgangsmåde til udvinding af isoflavoner. |
| DE9090119380T DE69001539T2 (de) | 1989-11-10 | 1990-10-10 | Verfahren zur herstellung von isoflavanonen. |
| EP91119841A EP0478003A1 (fr) | 1989-11-10 | 1990-10-10 | Procédé de protection d'un produit alimentaire |
| ES199090119380T ES2041484T3 (es) | 1989-11-10 | 1990-10-10 | Procedimiento de obtencion de isoflavonas. |
| AT90119380T ATE89004T1 (de) | 1989-11-10 | 1990-10-10 | Verfahren zur herstellung von isoflavanonen. |
| EP90119380A EP0426998B1 (fr) | 1989-11-10 | 1990-10-10 | Procédé d'obtention d'isoflavones |
| US07/598,247 US5141746A (en) | 1989-11-10 | 1990-10-16 | Process for obtaining genistin malonate and daidzin malonate |
| ZA908525A ZA908525B (en) | 1989-11-10 | 1990-10-24 | A process for the production of isoflavones |
| CA002029121A CA2029121A1 (en) | 1989-11-10 | 1990-11-01 | Process for the production of isoflavones |
| JP2305922A JPH03170495A (ja) | 1989-11-10 | 1990-11-09 | イソフラボンの製造方法 |
| SG78694A SG78694G (en) | 1989-11-10 | 1994-06-16 | Process for the preparation of isoflavanones. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4063/89A CH679584A5 (en, 2012) | 1989-11-10 | 1989-11-10 | |
| SG78694A SG78694G (en) | 1989-11-10 | 1994-06-16 | Process for the preparation of isoflavanones. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH679584A5 true CH679584A5 (en, 2012) | 1992-03-13 |
Family
ID=25694549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH4063/89A CH679584A5 (en, 2012) | 1989-11-10 | 1989-11-10 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5141746A (en, 2012) |
| EP (2) | EP0426998B1 (en, 2012) |
| JP (1) | JPH03170495A (en, 2012) |
| AT (1) | ATE89004T1 (en, 2012) |
| CA (1) | CA2029121A1 (en, 2012) |
| CH (1) | CH679584A5 (en, 2012) |
| DE (1) | DE69001539T2 (en, 2012) |
| DK (1) | DK0426998T3 (en, 2012) |
| ES (1) | ES2041484T3 (en, 2012) |
| SG (1) | SG78694G (en, 2012) |
| ZA (1) | ZA908525B (en, 2012) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0656786T3 (da) | 1992-05-19 | 2004-11-08 | Novogen Res Pty Ltd | Anvendelse af isoflavonphytoöstrogenekstrakter af soja eller klöver |
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-
1989
- 1989-11-10 CH CH4063/89A patent/CH679584A5/fr not_active IP Right Cessation
-
1990
- 1990-10-10 DE DE9090119380T patent/DE69001539T2/de not_active Expired - Fee Related
- 1990-10-10 DK DK90119380.5T patent/DK0426998T3/da not_active Application Discontinuation
- 1990-10-10 EP EP90119380A patent/EP0426998B1/fr not_active Expired - Lifetime
- 1990-10-10 AT AT90119380T patent/ATE89004T1/de not_active IP Right Cessation
- 1990-10-10 EP EP91119841A patent/EP0478003A1/fr not_active Withdrawn
- 1990-10-10 ES ES199090119380T patent/ES2041484T3/es not_active Expired - Lifetime
- 1990-10-16 US US07/598,247 patent/US5141746A/en not_active Expired - Fee Related
- 1990-10-24 ZA ZA908525A patent/ZA908525B/xx unknown
- 1990-11-01 CA CA002029121A patent/CA2029121A1/en not_active Abandoned
- 1990-11-09 JP JP2305922A patent/JPH03170495A/ja active Pending
-
1994
- 1994-06-16 SG SG78694A patent/SG78694G/en unknown
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1980002098A1 (en) * | 1979-04-11 | 1980-10-16 | Partnership Ltd | Isoflavones and related compounds,methods of preparing and using and antioxidant compositions containing same |
| FR2542318A1 (fr) * | 1983-03-10 | 1984-09-14 | Hayashibara Biochem Lab | Produits alimentaires a base de glycoside de soja et leur procede de preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0426998A3 (en) | 1991-07-31 |
| JPH03170495A (ja) | 1991-07-24 |
| ATE89004T1 (de) | 1993-05-15 |
| ZA908525B (en) | 1991-08-28 |
| CA2029121A1 (en) | 1991-05-11 |
| DK0426998T3 (da) | 1993-10-11 |
| ES2041484T3 (es) | 1993-11-16 |
| EP0426998A2 (fr) | 1991-05-15 |
| SG78694G (en) | 1994-10-14 |
| DE69001539D1 (de) | 1993-06-09 |
| EP0478003A1 (fr) | 1992-04-01 |
| EP0426998B1 (fr) | 1993-05-05 |
| US5141746A (en) | 1992-08-25 |
| DE69001539T2 (de) | 1993-08-12 |
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