JP2002501916A5 - - Google Patents
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- Publication number
- JP2002501916A5 JP2002501916A5 JP2000529328A JP2000529328A JP2002501916A5 JP 2002501916 A5 JP2002501916 A5 JP 2002501916A5 JP 2000529328 A JP2000529328 A JP 2000529328A JP 2000529328 A JP2000529328 A JP 2000529328A JP 2002501916 A5 JP2002501916 A5 JP 2002501916A5
- Authority
- JP
- Japan
- Prior art keywords
- extraction solvent
- aqueous
- water
- weight
- tocotrienol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 description 76
- 238000000605 extraction Methods 0.000 description 45
- 239000002904 solvent Substances 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 41
- 239000000203 mixture Substances 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- DFUSDJMZWQVQSF-XLGIIRLISA-N (2r)-2-methyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 DFUSDJMZWQVQSF-XLGIIRLISA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 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 21
- 239000007864 aqueous solution Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229930003802 tocotrienol Natural products 0.000 description 18
- 239000011731 tocotrienol Substances 0.000 description 18
- 235000019148 tocotrienols Nutrition 0.000 description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
- 239000011732 tocopherol Substances 0.000 description 14
- 229960001295 tocopherol Drugs 0.000 description 14
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 150000004665 fatty acids Chemical class 0.000 description 13
- 229930003799 tocopherol Natural products 0.000 description 13
- 235000010384 tocopherol Nutrition 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 235000019260 propionic acid Nutrition 0.000 description 8
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002781 deodorant agent Substances 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- OTXNTMVVOOBZCV-UHFFFAOYSA-N 2R-gamma-tocotrienol Natural products OC1=C(C)C(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-UHFFFAOYSA-N 0.000 description 4
- 235000019774 Rice Bran oil Nutrition 0.000 description 4
- 229940087168 alpha tocopherol Drugs 0.000 description 4
- RZFHLOLGZPDCHJ-DLQZEEBKSA-N alpha-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(/CC/C=C(\CC/C=C(\C)/C)/C)\C)(C)CCc2c1C RZFHLOLGZPDCHJ-DLQZEEBKSA-N 0.000 description 4
- OTXNTMVVOOBZCV-YMCDKREISA-N gamma-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)(C)CCc2c1 OTXNTMVVOOBZCV-YMCDKREISA-N 0.000 description 4
- 239000008165 rice bran oil Substances 0.000 description 4
- 229960000984 tocofersolan Drugs 0.000 description 4
- 235000004835 α-tocopherol Nutrition 0.000 description 4
- 239000002076 α-tocopherol Substances 0.000 description 4
- OTXNTMVVOOBZCV-WAZJVIJMSA-N γ-tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-WAZJVIJMSA-N 0.000 description 4
- 235000019150 γ-tocotrienol Nutrition 0.000 description 4
- 239000011722 γ-tocotrienol Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- -1 sterol ester Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- XBZYWSMVVKYHQN-MYPRUECHSA-N (4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Chemical compound C1C[C@H](O)[C@@](C)(COS(O)(=O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C XBZYWSMVVKYHQN-MYPRUECHSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- QLDNWJOJCDIMKK-UHFFFAOYSA-N Obtusifoliol Natural products CC12CCC(O)C(C)C1CCC1=C2CCC2(C)C(C(C)CCC(=C)C(C)C)CCC21 QLDNWJOJCDIMKK-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7296398P | 1998-01-29 | 1998-01-29 | |
| US7296298P | 1998-01-29 | 1998-01-29 | |
| US60/072,962 | 1998-01-29 | ||
| US60/072,963 | 1998-01-29 | ||
| PCT/US1999/001571 WO1999038860A1 (en) | 1998-01-29 | 1999-01-26 | Methods for separating a tocotrienol from a tocol-containing mixture and compositions thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002501916A JP2002501916A (ja) | 2002-01-22 |
| JP2002501916A5 true JP2002501916A5 (https=) | 2006-03-09 |
Family
ID=26753962
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000529327A Pending JP2002501915A (ja) | 1998-01-29 | 1999-01-26 | トコール含有混合物からのトコールの分離方法 |
| JP2000529328A Pending JP2002501916A (ja) | 1998-01-29 | 1999-01-26 | トコール含有混合物からのトコトリエノールの分離方法及びその組成物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000529327A Pending JP2002501915A (ja) | 1998-01-29 | 1999-01-26 | トコール含有混合物からのトコールの分離方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6159347A (https=) |
| EP (2) | EP1051412B1 (https=) |
| JP (2) | JP2002501915A (https=) |
| CN (2) | CN1295568A (https=) |
| BR (2) | BR9908141A (https=) |
| ES (2) | ES2178384T3 (https=) |
| MY (1) | MY124273A (https=) |
| WO (2) | WO1999038860A1 (https=) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6706898B2 (en) | 1998-01-29 | 2004-03-16 | Archer-Daniels-Midland Company | Methods for separating a tocopherol from a tocopherol-containing mixture |
| AU5041400A (en) | 1999-05-24 | 2000-12-12 | America River Nutrition, Inc. | Tocotrienols and geranylgeraniol from LTiGTbixa orellanaLT/iGT byproducts |
| US6395915B1 (en) * | 1999-09-10 | 2002-05-28 | Technikrom, Inc. | Method for producing purified tocotrienols and tocopherols using liquid chromatography |
| US6706474B1 (en) * | 2000-06-27 | 2004-03-16 | Board Of Trustees Of The University Of Illinois | Nucleic acid enzyme biosensors for ions |
| US6838104B2 (en) * | 2000-12-20 | 2005-01-04 | Archer Daniels Midland Company | Process for the production of tocotrienols |
| US6867308B2 (en) | 2001-09-19 | 2005-03-15 | Archer-Daniels-Midland Company | Process for separation of tocopherols |
| US6890719B2 (en) * | 2002-05-10 | 2005-05-10 | The Board Of Trustess Of The University Of Illinois | Fluorescence based biosensor |
| US7461048B2 (en) * | 2003-07-21 | 2008-12-02 | Aureon Laboratories, Inc. | Systems and methods for treating, diagnosing and predicting the occurrence of a medical condition |
| US7416756B2 (en) * | 2003-09-10 | 2008-08-26 | Eastman Chemical Company | Process for the recovery of a phytolipid composition |
| KR20060134913A (ko) * | 2003-09-10 | 2006-12-28 | 이스트만 케미칼 컴파니 | 피토리피드 조성물의 회수 방법 |
| WO2005035490A2 (en) * | 2003-10-10 | 2005-04-21 | Yasoo Health, Inc. | PROCESS FOR SYNTHESIZING d-TOCOTRIENOLS |
| MY173044A (en) | 2003-11-19 | 2019-12-20 | Carotech Bhd | Recovery of phytonutriens from oils |
| ES2619303T3 (es) | 2005-06-01 | 2017-06-26 | Edison Pharmaceuticals, Inc. | Productos terapéuticos redox activos para el tratamiento de enfermedades mitocondriales y otras afecciones y modulación de biomarcadores energéticos |
| US7892734B2 (en) * | 2005-08-11 | 2011-02-22 | The Board Of Trustees Of The University Of Illinois | Aptamer based colorimetric sensor systems |
| WO2007100652A2 (en) | 2006-02-22 | 2007-09-07 | Edison Pharmaceuticals, Inc. | Side chain variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| US7799554B2 (en) * | 2006-03-16 | 2010-09-21 | The Board Of Trustees Of The University Of Illinois | Lateral flow devices |
| US8415461B2 (en) * | 2007-01-19 | 2013-04-09 | The Board Of Trustees Of The University Of Illinois | Amphiphilic substances and functionalized lipid vesicles including the same |
| US8058415B2 (en) * | 2007-04-24 | 2011-11-15 | The Board Of Trustees Of The University Of Illinois | Aptamer- and nucleic acid enzyme-based systems for simultaneous detection of multiple analytes |
| WO2008142433A1 (en) * | 2007-05-24 | 2008-11-27 | Loders Croklaan B.V. | Process for producing compositions comprising tocoherols and tocotrienols |
| WO2009012309A2 (en) * | 2007-07-16 | 2009-01-22 | The Board Of Trustees Of The University Of Illinois | Nucleic acid based fluorescent sensor for divalent copper ion detection |
| US8568690B2 (en) * | 2007-07-31 | 2013-10-29 | The Board Of Trustees Of The University Of Illinois | MRI contrast agents and high-throughput screening by MRI |
| US8367416B2 (en) | 2007-08-10 | 2013-02-05 | The Board Of Trustees Of The University Of Illinois | Nucleic acid based fluorescent sensor for mercury detection |
| US20090090894A1 (en) * | 2007-10-05 | 2009-04-09 | Bin Wang | Separation and extraction system |
| US20100105039A1 (en) * | 2008-06-03 | 2010-04-29 | Yi Lu | Label-free colorimetric detection |
| MX363223B (es) | 2008-09-10 | 2019-03-15 | Bioelectron Tech Corp | Tratamiento de trastornos generalizados del desarrollo con terapeuticos con actividad redox. |
| US8062893B2 (en) | 2008-10-10 | 2011-11-22 | The Board Of Trustees Of The University Of Illinois | Fluorescent sensor for mercury |
| ES2553557T3 (es) | 2008-10-28 | 2015-12-10 | Edison Pharmaceuticals, Inc. | Proceso para la producción de alfa-tocotrienol y derivados |
| CA2777479C (en) | 2009-04-28 | 2017-10-17 | Ptc Therapeutics, Inc. | Treatment of leber's hereditary optic neuropathy and dominant optic atrophy with tocotrienol quinones |
| EP2445519A4 (en) | 2009-06-25 | 2012-12-26 | Ampere Life Sciences Inc | TREATMENT OF PERVASIVE DEVELOPMENT DISORDERS USING TOCOTRIENOLS OR TOCOTRIENOLS ENRICHED EXTRACTS |
| US8815156B2 (en) | 2010-07-19 | 2014-08-26 | Andalyze, Inc. | Sensor housing and reagent chemistry |
| EP2734512B1 (en) | 2011-07-19 | 2019-11-20 | Bioelectron Technology Corporation | Methods for selective oxidation of alpha tocotrienol in the presence of non-alpha tocotrienols |
| KR101489098B1 (ko) | 2012-01-25 | 2015-02-02 | 아사히 가세이 케미칼즈 가부시키가이샤 | 분리 방법 |
| EP2810940A1 (en) * | 2013-06-06 | 2014-12-10 | Sulzer Chemtech AG | A Process to Prepare A Tocopherol Concentrate |
| US9512098B1 (en) | 2014-02-03 | 2016-12-06 | Board Of Trustees Of The University Of Arkansas | Process of producing purified gamma- and delta-tocotrienols from tocol-rich oils or distillates |
| AU2015217822B8 (en) | 2014-02-11 | 2018-04-05 | Evonik Operations Gmbh | Method for producing vitamin E-enriched, especially tocotrienol-enriched, compositions from natural oils |
| WO2017106786A1 (en) | 2015-12-16 | 2017-06-22 | Bioelectron Technology Corporation | Improved methods for enriching alpha-tocotrienol from mixed tocol compositions |
| US10703701B2 (en) | 2015-12-17 | 2020-07-07 | Ptc Therapeutics, Inc. | Fluoroalkyl, fluoroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders |
| MY184673A (en) * | 2018-03-16 | 2021-04-15 | Palm Nutraceuticals Sdn Bhd | A process of preparing vitamin e concentrate |
| CN110251980B (zh) * | 2019-04-22 | 2021-03-23 | 中建安装集团有限公司 | 一种二恶烷水溶液中提纯优品级二恶烷的装置及方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2866797A (en) * | 1954-11-01 | 1958-12-30 | Gen Mills Inc | Improved process of isolating sterols |
| US3153055A (en) * | 1962-03-20 | 1964-10-13 | Eastman Kodak Co | Process for separating tocopherols and sterols from deodorizer sludge and the like |
| US3335154A (en) | 1963-06-04 | 1967-08-08 | Eastman Kodak Co | Separation of tocopherols and sterols from deodorizer sludge and the like |
| US4454329A (en) | 1980-07-04 | 1984-06-12 | The Nisshin Oil Mills, Ltd. | Process for preparation of tocopherol concentrates |
| US4480108A (en) * | 1983-08-01 | 1984-10-30 | Eastman Kodak Company | Process for separation of tocopherol homologues |
| JPS6048981A (ja) | 1983-08-29 | 1985-03-16 | Showa Denko Kk | 高純度トコフェロ−ルの製造方法 |
| JPS60149582A (ja) * | 1984-01-14 | 1985-08-07 | Mitsui Petrochem Ind Ltd | トコフエロ−ルの精製方法 |
| JPS60185776A (ja) | 1984-03-05 | 1985-09-21 | Riken Vitamin Co Ltd | トコフエロ−ルの精製濃縮法 |
| EP0171009B1 (en) | 1984-08-02 | 1991-05-22 | HENKEL CORPORATION (a Delaware corp.) | Purification of tocopherols by extraction |
| US4550183A (en) * | 1984-08-02 | 1985-10-29 | Henkel Corporation | Purification of tocopherols |
| JPS6160619A (ja) * | 1984-08-31 | 1986-03-28 | Eisai Co Ltd | 分散性粉末 |
| JPS6193178A (ja) * | 1984-10-12 | 1986-05-12 | Agency Of Ind Science & Technol | トコトリエノ−ル類の分離方法 |
| JPS61151186A (ja) * | 1984-12-24 | 1986-07-09 | Nisshin Oil Mills Ltd:The | トコトリエノ−ル類およびトコフエロ−ル類の濃縮法 |
| DE3615029A1 (de) | 1985-05-06 | 1986-11-06 | Henkel Corp., Minneapolis, Minn. | Methanol-extraktion von tocopherol |
| JPH029875A (ja) * | 1988-03-16 | 1990-01-12 | Bio Ind Kyokai | トコフェロール及びトコトリエノールの製造方法 |
| JPH03127730A (ja) | 1989-10-11 | 1991-05-30 | Kikaku Nijiyuuichi:Kk | ビタミンｅの製造方法 |
| MY108071A (en) * | 1990-05-23 | 1996-08-15 | Pentad Foods Int | Stabilization and recovery method for tocotrienol and tocopherol products. |
| US5487817A (en) * | 1993-02-11 | 1996-01-30 | Hoffmann-La Roche Inc. | Process for tocopherols and sterols from natural sources |
| JPH09502701A (ja) * | 1993-08-06 | 1997-03-18 | ヘンケル コーポレーション | トコフェロール類の回収 |
| US5512691A (en) * | 1994-11-07 | 1996-04-30 | Eastman Chemical Company | Process for the production of tocopherol concentrates |
| US5660691A (en) * | 1995-11-13 | 1997-08-26 | Eastman Chemical Company | Process for the production of tocotrienol/tocopherol blend concentrates |
| US5703252A (en) * | 1995-12-13 | 1997-12-30 | Henkel Corporation | Recovery of Tocopherols |
-
1999
- 1999-01-26 EP EP99904267A patent/EP1051412B1/en not_active Expired - Lifetime
- 1999-01-26 CN CN99802443A patent/CN1295568A/zh active Pending
- 1999-01-26 JP JP2000529327A patent/JP2002501915A/ja active Pending
- 1999-01-26 BR BR9908141-5A patent/BR9908141A/pt not_active IP Right Cessation
- 1999-01-26 ES ES99904266T patent/ES2178384T3/es not_active Expired - Lifetime
- 1999-01-26 WO PCT/US1999/001571 patent/WO1999038860A1/en not_active Ceased
- 1999-01-26 EP EP99904266A patent/EP1051411B1/en not_active Expired - Lifetime
- 1999-01-26 ES ES99904267T patent/ES2207931T3/es not_active Expired - Lifetime
- 1999-01-26 WO PCT/US1999/001570 patent/WO1999038859A1/en not_active Ceased
- 1999-01-26 US US09/237,406 patent/US6159347A/en not_active Expired - Fee Related
- 1999-01-26 US US09/237,384 patent/US6224717B1/en not_active Expired - Fee Related
- 1999-01-26 JP JP2000529328A patent/JP2002501916A/ja active Pending
- 1999-01-26 CN CNB998024449A patent/CN1221542C/zh not_active Expired - Fee Related
- 1999-01-26 BR BR9907278-5A patent/BR9907278A/pt not_active IP Right Cessation
- 1999-01-28 MY MYPI99000291A patent/MY124273A/en unknown
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