JP2002501915A - トコール含有混合物からのトコールの分離方法 - Google Patents
トコール含有混合物からのトコールの分離方法Info
- Publication number
- JP2002501915A JP2002501915A JP2000529327A JP2000529327A JP2002501915A JP 2002501915 A JP2002501915 A JP 2002501915A JP 2000529327 A JP2000529327 A JP 2000529327A JP 2000529327 A JP2000529327 A JP 2000529327A JP 2002501915 A JP2002501915 A JP 2002501915A
- Authority
- JP
- Japan
- Prior art keywords
- tocol
- extraction solvent
- mixture
- aqueous
- water
- 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
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- 239000003495 polar organic solvent Substances 0.000 claims abstract description 17
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- 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 claims description 85
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002540 palm oil Substances 0.000 claims description 4
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- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 2
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
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- 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 claims 1
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 235000019151 β-tocotrienol Nutrition 0.000 description 2
- FGYKUFVNYVMTAM-UHFFFAOYSA-N (R)-2,5,8-trimethyl-2-(4,8,12-trimethyl-trideca-3t,7t,11-trienyl)-chroman-6-ol Natural products OC1=CC(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- UEFGLENGHNNEBY-UHFFFAOYSA-N 1-methoxyethanol hydrate Chemical compound O.COC(C)O UEFGLENGHNNEBY-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- FGYKUFVNYVMTAM-YMCDKREISA-N beta-Tocotrienol Natural products Oc1c(C)c2c(c(C)c1)O[C@@](CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)(C)CC2 FGYKUFVNYVMTAM-YMCDKREISA-N 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000000828 canola oil Substances 0.000 description 1
- 235000019519 canola oil Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FGYKUFVNYVMTAM-MUUNZHRXSA-N epsilon-Tocopherol Natural products OC1=CC(C)=C2O[C@@](CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-MUUNZHRXSA-N 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000019488 nut oil Nutrition 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229940127084 other anti-cancer agent Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 125000002640 tocopherol group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003773 α-tocotrienols Chemical class 0.000 description 1
- 239000011723 β-tocotrienol Substances 0.000 description 1
- FGYKUFVNYVMTAM-WAZJVIJMSA-N β-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-WAZJVIJMSA-N 0.000 description 1
- 150000003782 β-tocotrienols Chemical class 0.000 description 1
- 150000003786 γ-tocotrienols Chemical class 0.000 description 1
- 150000003790 δ-tocotrienols Chemical class 0.000 description 1
Classifications
-
- 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
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7296298P | 1998-01-29 | 1998-01-29 | |
| US7296398P | 1998-01-29 | 1998-01-29 | |
| US60/072,962 | 1998-01-29 | ||
| US60/072,963 | 1998-01-29 | ||
| PCT/US1999/001570 WO1999038859A1 (en) | 1998-01-29 | 1999-01-26 | Methods for separating a tocol from a tocol-containing mixture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2002501915A true JP2002501915A (ja) | 2002-01-22 |
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 After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6224717B1 (https=) |
| EP (2) | EP1051411B1 (https=) |
| JP (2) | JP2002501915A (https=) |
| CN (2) | CN1221542C (https=) |
| BR (2) | BR9907278A (https=) |
| ES (2) | ES2207931T3 (https=) |
| MY (1) | MY124273A (https=) |
| WO (2) | WO1999038859A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007505117A (ja) * | 2003-09-10 | 2007-03-08 | イーストマン ケミカル カンパニー | フィトリピド組成物の回収方法 |
Families Citing this family (38)
| 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 |
| US6350453B1 (en) | 1999-05-24 | 2002-02-26 | American River Nutrition, Inc. | Tocotrienols and geranylgeraniol from Bixa orellana 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 |
| 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 |
| EP2471530B1 (en) | 2005-06-01 | 2017-01-11 | Edison Pharmaceuticals, Inc. | Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| US7892734B2 (en) * | 2005-08-11 | 2011-02-22 | The Board Of Trustees Of The University Of Illinois | Aptamer based colorimetric sensor systems |
| US9278085B2 (en) | 2006-02-22 | 2016-03-08 | 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 |
| US8409800B2 (en) * | 2007-07-16 | 2013-04-02 | The Board Of Trustees Of The University Of Illinois | Nucleic acid based fluorescent sensor for copper 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 |
| EP2344142B1 (en) | 2008-09-10 | 2024-06-26 | PTC Therapeutics, Inc. | Treatment of pervasive developmental disorders with redox-active therapeutics |
| US8062893B2 (en) | 2008-10-10 | 2011-11-22 | The Board Of Trustees Of The University Of Illinois | Fluorescent sensor for mercury |
| CA2741767C (en) | 2008-10-28 | 2017-09-12 | Ptc Therapeutics, Inc. | Process for the production of alpha-tocotrienol and derivatives |
| PL2424495T3 (pl) | 2009-04-28 | 2018-06-29 | Bioelectron Technology Corporation | Leczenie dziedzicznej neuropatii nerwów wzrokowych lebera i dominującego zaniku nerwu wzrokowego chinonami tokotrienolu |
| EP2609921A1 (en) | 2009-06-25 | 2013-07-03 | Ampere Life Sciences, Inc. | Treatment of pervasive developmental disorders with tocotrienols or tocotrienol enriched extracts |
| US8815156B2 (en) | 2010-07-19 | 2014-08-26 | Andalyze, Inc. | Sensor housing and reagent chemistry |
| JP2014520894A (ja) | 2011-07-19 | 2014-08-25 | エジソン ファーマシューティカルズ， インコーポレイテッド | 非アルファトコトリエノールの存在下でのアルファトコトリエノールの選択的酸化のための方法 |
| SG2013017017A (en) | 2012-01-25 | 2014-09-26 | Asahi Kasei Chemicals Corp | A method of separation |
| 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 |
| MY171445A (en) | 2014-02-11 | 2019-10-15 | Evonik Degussa Gmbh | Method for producing vitamine e-enriched, especially tocotrienol-enriched, compositions from natural oils |
| EP3390377B1 (en) | 2015-12-16 | 2026-03-25 | PTC Therapeutics, Inc. | Improved methods for enriching alpha-tocotrienol from mixed tocol compositions |
| WO2017106803A1 (en) | 2015-12-17 | 2017-06-22 | Bioelectron Technology Corporation | Flouroalkyl, flouroalkoxy, 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 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6153280A (ja) * | 1984-08-02 | 1986-03-17 | ヘンケル・コーポレイション | 抽出によるトコフエロールの精製法 |
| 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 |
| JPS61268677A (ja) * | 1985-05-06 | 1986-11-28 | ヘンケル・コ−ポレイシヨン | トコフエロ−ルのメタノ−ル抽出 |
| JPH072827A (ja) * | 1993-02-11 | 1995-01-06 | F Hoffmann La Roche Ag | トコフエロール類およびステロール類の回収方法 |
| WO1996014311A1 (en) * | 1994-11-07 | 1996-05-17 | Eastman Chemical Company | Process for the production of tocopherol and tocopherol/tocotrienol concentrates |
| WO1997021697A1 (en) * | 1995-12-13 | 1997-06-19 | Henkel Corporation | Recovery of tocopherols |
| US5660691A (en) * | 1995-11-13 | 1997-08-26 | Eastman Chemical Company | Process for the production of tocotrienol/tocopherol blend concentrates |
Family Cites Families (15)
| 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 |
| 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 |
| EP0333472B1 (en) * | 1988-03-16 | 1997-10-08 | PALM OIL RESEARCH & DEVELOPMENT BOARD | Production of high concentration tocopherols and tocotrienols from palm oil by-products |
| 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. |
| ATE289301T1 (de) * | 1993-08-06 | 2005-03-15 | Cognis Corp | Wiedergewinnung von tocopherolen |
-
1999
- 1999-01-26 JP JP2000529327A patent/JP2002501915A/ja active Pending
- 1999-01-26 US US09/237,384 patent/US6224717B1/en not_active Expired - Fee Related
- 1999-01-26 US US09/237,406 patent/US6159347A/en not_active Expired - Fee Related
- 1999-01-26 EP EP99904266A patent/EP1051411B1/en not_active Expired - Lifetime
- 1999-01-26 WO PCT/US1999/001570 patent/WO1999038859A1/en not_active Ceased
- 1999-01-26 ES ES99904267T patent/ES2207931T3/es not_active Expired - Lifetime
- 1999-01-26 EP EP99904267A patent/EP1051412B1/en not_active Expired - Lifetime
- 1999-01-26 BR BR9907278-5A patent/BR9907278A/pt not_active IP Right Cessation
- 1999-01-26 CN CNB998024449A patent/CN1221542C/zh not_active Expired - Fee Related
- 1999-01-26 JP JP2000529328A patent/JP2002501916A/ja active Pending
- 1999-01-26 BR BR9908141-5A patent/BR9908141A/pt not_active IP Right Cessation
- 1999-01-26 CN CN99802443A patent/CN1295568A/zh active Pending
- 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
- 1999-01-28 MY MYPI99000291A patent/MY124273A/en unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6153280A (ja) * | 1984-08-02 | 1986-03-17 | ヘンケル・コーポレイション | 抽出によるトコフエロールの精製法 |
| 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 |
| JPS61268677A (ja) * | 1985-05-06 | 1986-11-28 | ヘンケル・コ−ポレイシヨン | トコフエロ−ルのメタノ−ル抽出 |
| JPH072827A (ja) * | 1993-02-11 | 1995-01-06 | F Hoffmann La Roche Ag | トコフエロール類およびステロール類の回収方法 |
| WO1996014311A1 (en) * | 1994-11-07 | 1996-05-17 | Eastman Chemical Company | Process for the production of tocopherol and tocopherol/tocotrienol concentrates |
| US5660691A (en) * | 1995-11-13 | 1997-08-26 | Eastman Chemical Company | Process for the production of tocotrienol/tocopherol blend concentrates |
| WO1997021697A1 (en) * | 1995-12-13 | 1997-06-19 | Henkel Corporation | Recovery of tocopherols |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007505117A (ja) * | 2003-09-10 | 2007-03-08 | イーストマン ケミカル カンパニー | フィトリピド組成物の回収方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002501916A (ja) | 2002-01-22 |
| EP1051412A1 (en) | 2000-11-15 |
| WO1999038859A1 (en) | 1999-08-05 |
| BR9907278A (pt) | 2000-10-24 |
| CN1314901A (zh) | 2001-09-26 |
| CN1221542C (zh) | 2005-10-05 |
| BR9908141A (pt) | 2000-11-28 |
| ES2178384T3 (es) | 2002-12-16 |
| EP1051411A1 (en) | 2000-11-15 |
| ES2207931T3 (es) | 2004-06-01 |
| WO1999038860A1 (en) | 1999-08-05 |
| US6224717B1 (en) | 2001-05-01 |
| MY124273A (en) | 2006-06-30 |
| EP1051411B1 (en) | 2002-08-28 |
| US6159347A (en) | 2000-12-12 |
| EP1051412B1 (en) | 2003-09-24 |
| CN1295568A (zh) | 2001-05-16 |
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