NL7906193A - Isoflavonen en verwante verbindingen, werkwijzen ter bereiding daarvan, alsmede deze verbindingen-bevattende antioxydantsamenstellingen. - Google Patents
Isoflavonen en verwante verbindingen, werkwijzen ter bereiding daarvan, alsmede deze verbindingen-bevattende antioxydantsamenstellingen. Download PDFInfo
- Publication number
- NL7906193A NL7906193A NL7906193A NL7906193A NL7906193A NL 7906193 A NL7906193 A NL 7906193A NL 7906193 A NL7906193 A NL 7906193A NL 7906193 A NL7906193 A NL 7906193A NL 7906193 A NL7906193 A NL 7906193A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- oil
- compound
- edible
- compound according
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 122
- 239000000203 mixture Substances 0.000 title claims abstract description 70
- 238000000034 method Methods 0.000 title claims description 15
- 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 title abstract description 21
- 235000008696 isoflavones Nutrition 0.000 title abstract description 21
- 150000002515 isoflavone derivatives Chemical class 0.000 title abstract description 16
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 53
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 49
- 239000003921 oil Substances 0.000 claims abstract description 42
- 239000003925 fat Substances 0.000 claims abstract description 30
- 235000013305 food Nutrition 0.000 claims abstract description 25
- 239000000047 product Substances 0.000 claims abstract description 25
- 235000013548 tempeh Nutrition 0.000 claims abstract description 21
- 235000010469 Glycine max Nutrition 0.000 claims abstract description 10
- 244000068988 Glycine max Species 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 235000019198 oils Nutrition 0.000 claims description 41
- 235000019197 fats Nutrition 0.000 claims description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 239000002244 precipitate Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 239000008157 edible vegetable oil Substances 0.000 claims description 11
- -1 lard Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 7
- 230000000087 stabilizing effect Effects 0.000 claims description 7
- 239000002002 slurry Substances 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000000401 methanolic extract Substances 0.000 claims description 5
- 241000251468 Actinopterygii Species 0.000 claims description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 4
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 4
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 238000013375 chromatographic separation Methods 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 235000013372 meat Nutrition 0.000 claims description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 3
- 239000008158 vegetable oil Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 238000005377 adsorption chromatography Methods 0.000 claims description 2
- 239000000356 contaminant Substances 0.000 claims description 2
- 235000005687 corn oil Nutrition 0.000 claims description 2
- 239000002285 corn oil Substances 0.000 claims description 2
- 239000002035 hexane extract Substances 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 235000019737 Animal fat Nutrition 0.000 claims 1
- 229910015900 BF3 Inorganic materials 0.000 claims 1
- 125000006519 CCH3 Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 235000006708 antioxidants Nutrition 0.000 abstract description 35
- 238000007385 chemical modification Methods 0.000 abstract description 4
- 235000014593 oils and fats Nutrition 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 230000006866 deterioration Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- GCWOYVFHJDNKIN-UHFFFAOYSA-N Texasin Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(O)=C(O)C=C2C1=O GCWOYVFHJDNKIN-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 8
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 6
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000013112 stability test Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 4
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- RELBLTGUBMEHHL-UHFFFAOYSA-N 6,7-dihydroxy-3-phenylchromen-4-one Chemical compound O=C1C=2C=C(O)C(O)=CC=2OC=C1C1=CC=CC=C1 RELBLTGUBMEHHL-UHFFFAOYSA-N 0.000 description 3
- RQEMHCIRNVNLNO-UHFFFAOYSA-N 7-methoxy-3-(4-methoxyphenyl)-2-phenyl-2,3-dihydrochromen-4-one Chemical compound C1=CC(OC)=CC=C1C1C(=O)C2=CC=C(OC)C=C2OC1C1=CC=CC=C1 RQEMHCIRNVNLNO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940087168 alpha tocopherol Drugs 0.000 description 3
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 229960000984 tocofersolan Drugs 0.000 description 3
- 239000002076 α-tocopherol Substances 0.000 description 3
- 235000004835 α-tocopherol Nutrition 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 241000235527 Rhizopus Species 0.000 description 2
- 244000205939 Rhizopus oligosporus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 235000008466 glycitein Nutrition 0.000 description 2
- DXYUAIFZCFRPTH-UHFFFAOYSA-N glycitein Chemical compound C1=C(O)C(OC)=CC(C2=O)=C1OC=C2C1=CC=C(O)C=C1 DXYUAIFZCFRPTH-UHFFFAOYSA-N 0.000 description 2
- NNUVCMKMNCKPKN-UHFFFAOYSA-N glycitein Natural products COc1c(O)ccc2OC=C(C(=O)c12)c3ccc(O)cc3 NNUVCMKMNCKPKN-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- KTPWETRNSUKEME-UHFFFAOYSA-N methoxymethane;trifluoroborane Chemical compound COC.FB(F)F KTPWETRNSUKEME-UHFFFAOYSA-N 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PACGLQCRGWFBJH-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1 PACGLQCRGWFBJH-UHFFFAOYSA-N 0.000 description 1
- CFQTWIRCKXFXSC-UHFFFAOYSA-N 3-(1-methoxycyclohexa-2,4-dien-1-yl)-3,4-dihydro-2h-chromene-6,7-diol Chemical compound C1OC2=CC(O)=C(O)C=C2CC1C1(OC)CC=CC=C1 CFQTWIRCKXFXSC-UHFFFAOYSA-N 0.000 description 1
- RAMQRPMZZPLEPS-UHFFFAOYSA-N 3-(2-methoxyphenyl)-3,4-dihydro-2H-chromene-6,7-diol Chemical compound OC=1C=C2CC(COC2=CC=1O)C1=C(C=CC=C1)OC RAMQRPMZZPLEPS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 101150096316 5 gene Proteins 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- DZKZCXUIXLRBSY-UHFFFAOYSA-N Oc1ccc2oc(O)c(-c3ccccc3)c(=O)c2c1O Chemical compound Oc1ccc2oc(O)c(-c3ccccc3)c(=O)c2c1O DZKZCXUIXLRBSY-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000000471 Rhizopus oligosporus Nutrition 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 230000003509 anti-fertility effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000006539 genistein Nutrition 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
- 229940045109 genistein Drugs 0.000 description 1
- 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 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- WZEOZJQLTRFNCU-UHFFFAOYSA-N trifluoro(trifluoromethoxy)methane Chemical compound FC(F)(F)OC(F)(F)F WZEOZJQLTRFNCU-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
- C07C37/0555—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group being esterified hydroxy groups
-
- 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
-
- 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
- C07D311/34—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 3 only
- C07D311/36—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 3 only not hydrogenated in the hetero ring, e.g. isoflavones
-
- 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
- C07D311/34—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 3 only
- C07D311/38—2,3-Dihydro derivatives, e.g. isoflavanones
-
- 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
- C07D311/40—Separation, e.g. from natural material; Purification
-
- 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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
-
- 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
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
- C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fats And Perfumes (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Pyrane Compounds (AREA)
- Edible Oils And Fats (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/029,122 US4264509A (en) | 1977-06-08 | 1979-04-11 | Isoflavones and related compounds, methods of preparing and using and antioxidant compositions containing same |
| US2912279 | 1979-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL7906193A true NL7906193A (nl) | 1980-10-14 |
Family
ID=21847353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7906193A NL7906193A (nl) | 1979-04-11 | 1979-08-14 | Isoflavonen en verwante verbindingen, werkwijzen ter bereiding daarvan, alsmede deze verbindingen-bevattende antioxydantsamenstellingen. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4264509A (enExample) |
| EP (1) | EP0027796B1 (enExample) |
| JP (1) | JPS56500493A (enExample) |
| AT (1) | ATE8324T1 (enExample) |
| CA (1) | CA1140560A (enExample) |
| DE (1) | DE2967100D1 (enExample) |
| DK (1) | DK528880A (enExample) |
| NL (1) | NL7906193A (enExample) |
| WO (1) | WO1980002098A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8626344D0 (en) * | 1986-11-04 | 1986-12-03 | Zyma Sa | Bicyclic compounds |
| CH679584A5 (enExample) * | 1989-11-10 | 1992-03-13 | Nestle Sa | |
| JPH07506822A (ja) * | 1992-05-19 | 1995-07-27 | ノボゲン リサーチ ピーティーワイ リミッテッド | フィト−エストロゲン，類似体またはその代謝産物を含有する健康補助剤 |
| US6140469A (en) * | 1993-10-12 | 2000-10-31 | Protein Technologies International, Inc. | Protein isolate having an increased level of isoflavone compounds and process for producing the same |
| US5320949A (en) * | 1993-10-12 | 1994-06-14 | Protein Technologies International, Inc. | Process for producing aglucone isoflavone enriched vegetable protein fiber |
| FR2720395B1 (fr) * | 1994-05-31 | 1996-06-28 | Oreal | Nouveaux composés de la famille des benzohétérocycles. |
| US5827682A (en) * | 1995-06-07 | 1998-10-27 | Protein Technologies International, Inc. | Two-step conversion of vegetable protein isoflavone conjugates to aglucones |
| US6261565B1 (en) | 1996-03-13 | 2001-07-17 | Archer Daniels Midland Company | Method of preparing and using isoflavones |
| US5702752A (en) * | 1996-03-13 | 1997-12-30 | Archer Daniels Midland Company | Production of isoflavone enriched fractions from soy protein extracts |
| US5851792A (en) * | 1996-04-03 | 1998-12-22 | Shen; Jerome | Aglucone isoflavone enriched vegetable protein whey whey protein material aglucone isoflavone material high genistein content material and high daidzein content material and process for producing the same from a vegetable protein whey |
| US6015785A (en) * | 1996-04-12 | 2000-01-18 | Protein Technologies International, Inc. | Aglucone isofavone enriched vegetable protein extract and isolate and process for producing |
| US5821361A (en) * | 1996-06-11 | 1998-10-13 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| AUPO203996A0 (en) * | 1996-08-30 | 1996-09-26 | Novogen Research Pty Ltd | Therapeutic uses |
| US6146668A (en) | 1997-04-28 | 2000-11-14 | Novogen, Inc. | Preparation of isoflavones from legumes |
| CA2287965C (en) * | 1997-05-01 | 2009-10-20 | Graham Edmund Kelly | Treatment or prevention of menopausal symptoms and osteoporosis |
| US6228993B1 (en) | 1998-10-12 | 2001-05-08 | Central Soya Company, Inc. | Soy isoflavone concentrate process and product |
| US6320028B1 (en) | 1997-10-15 | 2001-11-20 | Central Soya Company, Inc. | Soy isoflavone concentrate process and product |
| US6369200B2 (en) | 1997-10-15 | 2002-04-09 | Central Soya Company, Inc. | Soy isoflavone concentrate process and product |
| AUPP112497A0 (en) * | 1997-12-24 | 1998-01-22 | Novogen Research Pty Ltd | Compositions and method for protecting skin from UV induced immunosupression and skin damage |
| US6132795A (en) * | 1998-03-15 | 2000-10-17 | Protein Technologies International, Inc. | Vegetable protein composition containing an isoflavone depleted vegetable protein material with an isoflavone containing material |
| AUPP260798A0 (en) * | 1998-03-26 | 1998-04-23 | Novogen Research Pty Ltd | Treatment of medical related conditions with isoflavone containing extracts of clover |
| US6083553A (en) * | 1998-06-05 | 2000-07-04 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US6001368A (en) * | 1998-09-03 | 1999-12-14 | Protein Technologies International, Inc. | Method for inhibiting or reducing the risk of macular degeneration |
| US6703051B1 (en) | 1998-10-13 | 2004-03-09 | Solae, Llc | Process for separating and recovering protein and isoflavones from a plant material |
| AUPP868599A0 (en) * | 1999-02-15 | 1999-03-11 | Novogen Research Pty Ltd | Production of isoflavone derivatives |
| AUPQ008299A0 (en) * | 1999-04-30 | 1999-05-27 | G.J. Consultants Pty Ltd | Isoflavone metabolites |
| US20090233999A1 (en) * | 1999-09-06 | 2009-09-17 | Novogen Research Pty Ltd | Compositions and therapeutic methods involving isoflavones and analogues thereof |
| AUPQ266199A0 (en) * | 1999-09-06 | 1999-09-30 | Novogen Research Pty Ltd | Compositions and therapeutic methods involving isoflavones and analogues thereof |
| AUPQ520300A0 (en) * | 2000-01-21 | 2000-02-17 | Novogen Research Pty Ltd | Food product and process |
| AUPR363301A0 (en) * | 2001-03-08 | 2001-04-05 | Novogen Research Pty Ltd | Dimeric isoflavones |
| US20050119301A1 (en) * | 2001-03-16 | 2005-06-02 | Alan Husband | Treatment of restenosis |
| ATE541569T1 (de) * | 2001-07-24 | 2012-02-15 | Cargill Inc | Verfahren zur isolation von phenolischen verbindungen |
| AUPR846401A0 (en) * | 2001-10-25 | 2001-11-15 | Novogen Research Pty Ltd | 6-Hydroxy isoflavones, derivatives and medicaments involving same |
| AU2002951833A0 (en) | 2002-10-02 | 2002-10-24 | Novogen Research Pty Ltd | Compositions and therapeutic methods invloving platinum complexes |
| AU2003265737B2 (en) * | 2002-10-02 | 2008-10-16 | Novogen Research Pty Ltd | Combination chemotherapy compositions and methods |
| WO2005103025A1 (en) * | 2004-04-21 | 2005-11-03 | Novogen Research Pty Ltd | Isoflavene synthetic method and catalyst |
| CN101056868B (zh) | 2004-09-21 | 2012-05-02 | 马休爱德华兹股份有限公司 | 取代的苯并二氢吡喃衍生物、药物及其在治疗中的应用 |
| US8080675B2 (en) | 2004-09-21 | 2011-12-20 | Marshall Edwards, Inc. | Chroman derivatives, medicaments and use in therapy |
| US7528267B2 (en) * | 2005-08-01 | 2009-05-05 | Girindus America, Inc. | Method for enantioselective hydrogenation of chromenes |
| US20070203227A1 (en) * | 2006-02-24 | 2007-08-30 | Herman Adlercreutz | Isoflavan and isoflavene compounds and their use as angiogenesis inhibitors |
| WO2012061409A1 (en) | 2010-11-01 | 2012-05-10 | Marshall Edwards, Inc. | Isoflavonoid compounds and methods for the treatment of cancer |
| PT3253208T (pt) | 2015-02-02 | 2021-06-17 | The Spanish National Cancer Res Centre | Terapêuticas de combinação para utilização no tratamento do cancro da mama |
| CN118619910B (zh) * | 2024-05-13 | 2025-11-18 | 右江民族医学院附属医院 | 一种葛花亭衍生物及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681085A (en) * | 1970-04-27 | 1972-08-01 | Paul Gyorgy | Food product containing tempeh |
| US3762933A (en) * | 1971-06-21 | 1973-10-02 | P Gyorgy | Stabilized edible oil and fat compositions containing oil of tempeh |
-
1979
- 1979-04-11 US US06/029,122 patent/US4264509A/en not_active Expired - Lifetime
- 1979-05-16 CA CA000327756A patent/CA1140560A/en not_active Expired
- 1979-05-18 JP JP50186879A patent/JPS56500493A/ja active Pending
- 1979-05-18 WO PCT/US1979/000347 patent/WO1980002098A1/en not_active Ceased
- 1979-05-18 DE DE7979901460T patent/DE2967100D1/de not_active Expired
- 1979-05-18 AT AT79901460T patent/ATE8324T1/de not_active IP Right Cessation
- 1979-08-14 NL NL7906193A patent/NL7906193A/nl not_active Application Discontinuation
-
1980
- 1980-10-23 EP EP79901460A patent/EP0027796B1/en not_active Expired
- 1980-12-11 DK DK528880A patent/DK528880A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK528880A (da) | 1980-12-11 |
| ATE8324T1 (de) | 1984-07-15 |
| WO1980002098A1 (en) | 1980-10-16 |
| EP0027796B1 (en) | 1984-07-11 |
| DE2967100D1 (en) | 1984-08-16 |
| CA1140560A (en) | 1983-02-01 |
| JPS56500493A (enExample) | 1981-04-16 |
| US4264509A (en) | 1981-04-28 |
| EP0027796A1 (en) | 1981-05-06 |
| EP0027796A4 (en) | 1981-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0027796B1 (en) | Chroman and chromanon-4 derivatives, process for their preparation, antioxidant compositions containing same and their use for stabilizing edible fats and oils | |
| US4390559A (en) | Isoflavones and related compounds, methods of preparing and using and antioxidant compositions containing same | |
| US4366082A (en) | Isoflavones and related compounds, methods of preparing and using and antioxidant compositions containing same | |
| Spielmeyer et al. | Influence of thermal treatment of rapeseed on the canolol content | |
| US4157984A (en) | Antioxidants, antioxidant compositions and methods of preparing and using same | |
| US4366248A (en) | Fermentation method of preparing antioxidants | |
| Dachtler et al. | On‐line LC‐NMR‐MS characterization of sesame oil extracts and assessment of their antioxidant activity | |
| US3950266A (en) | Method of producing an antioxidant composition from rosemary and sage | |
| US5985344A (en) | Process for obtaining micronutrient enriched rice bran oil | |
| US4218489A (en) | Antioxidants, antioxidant compositions and methods of preparing and using same | |
| CH679584A5 (enExample) | ||
| KR100719860B1 (ko) | 클로로-1-부탄을 사용하여 식물유로부터 비사포닌화물질을 추출하는 방법, 상기 비사포닌화 물질을 포함하는조성물 | |
| JP3283274B2 (ja) | 新規組成物 | |
| EP1363895B1 (en) | Process for the production of tocotrienols | |
| US20040121058A1 (en) | Process for extraction of antioxidants from sesame seed/cake | |
| JP5614285B2 (ja) | 食用油組成物用添加剤 | |
| JP2005272374A (ja) | フラバノン化合物、その製造方法及び抗酸化剤 | |
| US4649206A (en) | Lignan compound | |
| KR101049206B1 (ko) | 지용성 차 폴리페놀의 제조방법 | |
| CN105076915B (zh) | 一种酶法制备得到的脂溶性竹叶抗氧化物及其用途 | |
| Bueno-Borges et al. | A highly stable soybean oil-rich miscella obtained by ethanolic extraction as a promising biodiesel feedstock | |
| Olajide et al. | A novel antioxidant: 6, 6'-(butane-1, 1-diyl) bis (4-methylbenzene-1, 2-diol) | |
| KR100363112B1 (ko) | 감태로부터 분리된 신규 물질, 이의 추출 및 정제방법, 및항산화제로 사용하는 용도 | |
| KR100363111B1 (ko) | 감태로부터 분리된 신규 물질, 이의 추출 및 정제방법, 및항산화제로 사용하는 용도 | |
| JPH0867874A (ja) | 酸化防止剤の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |