ES2207931T3 - Procedimientos para separar un tocotrienol de una mezcla a base de tocol y composiciones producidas segun dichos procedimientos. - Google Patents
Procedimientos para separar un tocotrienol de una mezcla a base de tocol y composiciones producidas segun dichos procedimientos.Info
- Publication number
- ES2207931T3 ES2207931T3 ES99904267T ES99904267T ES2207931T3 ES 2207931 T3 ES2207931 T3 ES 2207931T3 ES 99904267 T ES99904267 T ES 99904267T ES 99904267 T ES99904267 T ES 99904267T ES 2207931 T3 ES2207931 T3 ES 2207931T3
- Authority
- ES
- Spain
- Prior art keywords
- aqueous
- tocolic
- mixture
- extraction
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 211
- 229930003802 tocotrienol Natural products 0.000 title claims abstract description 125
- 239000011731 tocotrienol Substances 0.000 title claims abstract description 125
- 235000019148 tocotrienols Nutrition 0.000 title claims abstract description 125
- 238000000034 method Methods 0.000 title claims abstract description 117
- 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 title claims abstract description 73
- 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 title description 21
- 238000000605 extraction Methods 0.000 claims abstract description 204
- 239000002904 solvent Substances 0.000 claims abstract description 182
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 170
- 239000011732 tocopherol Substances 0.000 claims abstract description 95
- 229930003799 tocopherol Natural products 0.000 claims abstract description 94
- 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 claims abstract description 92
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 72
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 58
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 57
- 229960001295 tocopherol Drugs 0.000 claims abstract description 55
- 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 claims abstract description 54
- 235000010384 tocopherol Nutrition 0.000 claims abstract description 54
- 239000000194 fatty acid Substances 0.000 claims abstract description 46
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 45
- 229930195729 fatty acid Natural products 0.000 claims abstract description 45
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 40
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 238000010438 heat treatment Methods 0.000 claims abstract description 21
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 20
- 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 claims abstract description 20
- 235000021588 free fatty acids Nutrition 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 17
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims abstract description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000005830 nonesterified fatty acids Chemical class 0.000 claims abstract description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229940093475 2-ethoxyethanol Drugs 0.000 claims abstract description 8
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 claims abstract description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims abstract description 8
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims abstract description 8
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003125 aqueous solvent Substances 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 83
- 238000004821 distillation Methods 0.000 claims description 45
- 235000019149 tocopherols Nutrition 0.000 claims description 40
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 claims description 40
- 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 claims description 30
- 235000019150 γ-tocotrienol Nutrition 0.000 claims description 30
- 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 claims description 29
- 235000004835 α-tocopherol Nutrition 0.000 claims description 26
- 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 claims description 25
- 239000011722 γ-tocotrienol Substances 0.000 claims description 25
- 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 claims description 25
- 229930182558 Sterol Natural products 0.000 claims description 21
- 235000003702 sterols Nutrition 0.000 claims description 21
- 229930195733 hydrocarbon Natural products 0.000 claims description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims description 20
- 239000002076 α-tocopherol Substances 0.000 claims description 19
- 229940087168 alpha tocopherol Drugs 0.000 claims description 18
- 150000003432 sterols Chemical class 0.000 claims description 18
- 229960000984 tocofersolan Drugs 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- -1 triterpenoid alcohol Natural products 0.000 claims description 15
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 12
- 239000008158 vegetable oil Substances 0.000 claims description 12
- 239000002781 deodorant agent Substances 0.000 claims description 11
- 235000019774 Rice Bran oil Nutrition 0.000 claims description 9
- 239000008165 rice bran oil Substances 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 230000008030 elimination Effects 0.000 claims description 8
- 238000003379 elimination reaction Methods 0.000 claims description 8
- 230000001877 deodorizing effect Effects 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000000638 solvent extraction Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003495 polar organic solvent Substances 0.000 claims description 5
- 235000019482 Palm oil Nutrition 0.000 claims description 4
- 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
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims 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 claims 1
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 1
- 239000012071 phase Substances 0.000 description 109
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 description 52
- 229940068778 tocotrienols Drugs 0.000 description 52
- 238000007670 refining Methods 0.000 description 20
- 239000006185 dispersion Substances 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 239000006184 cosolvent Substances 0.000 description 12
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 12
- 235000010382 gamma-tocopherol Nutrition 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 235000010389 delta-tocopherol Nutrition 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 9
- 239000007791 liquid phase Substances 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 230000032050 esterification Effects 0.000 description 8
- 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 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000001993 wax Substances 0.000 description 8
- 239000002478 γ-tocopherol Substances 0.000 description 8
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 8
- 239000012528 membrane Substances 0.000 description 7
- 150000003772 α-tocopherols Chemical class 0.000 description 7
- 235000019144 δ-tocotrienol Nutrition 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 235000019145 α-tocotrienol Nutrition 0.000 description 6
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 6
- 239000002446 δ-tocopherol Substances 0.000 description 6
- ODADKLYLWWCHNB-UHFFFAOYSA-N 2R-delta-tocotrienol Natural products OC1=CC(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 ODADKLYLWWCHNB-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- BTNBMQIHCRIGOU-UHFFFAOYSA-N delta-tocotrienol Natural products CC(=CCCC(=CCCC(=CCCOC1(C)CCc2cc(O)cc(C)c2O1)C)C)C BTNBMQIHCRIGOU-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000003786 γ-tocotrienols Chemical class 0.000 description 5
- 239000011729 δ-tocotrienol Substances 0.000 description 5
- ODADKLYLWWCHNB-LDYBVBFYSA-N δ-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 ODADKLYLWWCHNB-LDYBVBFYSA-N 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- RZFHLOLGZPDCHJ-XZXLULOTSA-N α-Tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C RZFHLOLGZPDCHJ-XZXLULOTSA-N 0.000 description 4
- 239000011730 α-tocotrienol Substances 0.000 description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 229940064063 alpha tocotrienol Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000008157 edible vegetable oil Substances 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- 235000007680 β-tocopherol Nutrition 0.000 description 3
- 239000011590 β-tocopherol Substances 0.000 description 3
- 150000003785 γ-tocopherols Chemical class 0.000 description 3
- 150000003789 δ-tocopherols Chemical class 0.000 description 3
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 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 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940066595 beta tocopherol Drugs 0.000 description 2
- 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 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 210000005056 cell body Anatomy 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 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 2
- 235000019197 fats Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229940031439 squalene Drugs 0.000 description 2
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 150000003773 α-tocotrienols Chemical class 0.000 description 2
- 235000019151 β-tocotrienol Nutrition 0.000 description 2
- 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 2
- 239000011723 β-tocotrienol Substances 0.000 description 2
- 150000003790 δ-tocotrienols Chemical class 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-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
- UIHCLUNTQKBZGK-UHFFFAOYSA-N 3-methyl-2-pentanone Chemical compound CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 244000188595 Brassica sinapistrum Species 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
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 108010010234 HDL Lipoproteins Proteins 0.000 description 1
- 102000015779 HDL Lipoproteins Human genes 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 108010028554 LDL Cholesterol Proteins 0.000 description 1
- 108010007622 LDL Lipoproteins Proteins 0.000 description 1
- 102000007330 LDL Lipoproteins Human genes 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- IGGUPRCHHJZPBS-UHFFFAOYSA-N Nonacosane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCC IGGUPRCHHJZPBS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 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
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 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
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 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
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- ZXKXJHAOUFHNAS-UHFFFAOYSA-N fenfluramine hydrochloride Chemical compound [Cl-].CC[NH2+]C(C)CC1=CC=CC(C(F)(F)F)=C1 ZXKXJHAOUFHNAS-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 238000002156 mixing Methods 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
- 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
- 229960002969 oleic acid Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7296298P | 1998-01-29 | 1998-01-29 | |
| US7296398P | 1998-01-29 | 1998-01-29 | |
| US72963P | 1998-01-29 | ||
| US72962P | 1998-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2207931T3 true ES2207931T3 (es) | 2004-06-01 |
Family
ID=26753962
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99904267T Expired - Lifetime ES2207931T3 (es) | 1998-01-29 | 1999-01-26 | Procedimientos para separar un tocotrienol de una mezcla a base de tocol y composiciones producidas segun dichos procedimientos. |
| ES99904266T Expired - Lifetime ES2178384T3 (es) | 1998-01-29 | 1999-01-26 | Metodos para separar un tocol de una mezcla que contiene tocoles. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99904266T Expired - Lifetime ES2178384T3 (es) | 1998-01-29 | 1999-01-26 | Metodos para separar un tocol de una mezcla que contiene tocoles. |
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=) |
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 |
| 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 |
| CA2534961C (en) * | 2003-09-10 | 2009-06-16 | 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 |
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 |
| US4550183A (en) | 1984-08-02 | 1985-10-29 | Henkel Corporation | Purification of tocopherols |
| EP0171009B1 (en) * | 1984-08-02 | 1991-05-22 | HENKEL CORPORATION (a Delaware corp.) | Purification of tocopherols by extraction |
| 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 |
| 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. |
| US5487817A (en) * | 1993-02-11 | 1996-01-30 | Hoffmann-La Roche Inc. | Process for tocopherols and sterols from natural sources |
| ATE289301T1 (de) * | 1993-08-06 | 2005-03-15 | Cognis Corp | Wiedergewinnung von tocopherolen |
| 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 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
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 |
| JP2002501915A (ja) | 2002-01-22 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2207931T3 (es) | Procedimientos para separar un tocotrienol de una mezcla a base de tocol y composiciones producidas segun dichos procedimientos. | |
| CA2143441C (en) | Recovery of tocopherol and sterol | |
| JP4142096B2 (ja) | トコフェロール濃縮物及びトコフェロール／トコトリエノール濃縮物の製造方法 | |
| US6586201B1 (en) | Method of chromatographic isolation for non-glyceride components | |
| US7544822B2 (en) | Recovery of phytonutrients from oils | |
| JP2013100506A (ja) | 特殊なパーム油製品およびその他の特殊な植物油製品 | |
| US6706898B2 (en) | Methods for separating a tocopherol from a tocopherol-containing mixture | |
| CA2081018C (en) | Countercurrent liquid/liquid extraction to fractionate complex mixtures containing medium and long chain fatty acid triglycerides | |
| US7368583B2 (en) | Process for recovery of plant sterols from by-product of vegetable oil refining | |
| KR20010101669A (ko) | 토코페롤 함유 혼합물로부터 토코페롤을 분리하는 방법 및이 방법에 의해 제조된 조성물 | |
| ES2308924B1 (es) | Procedimiento de obtencion de escualeno. | |
| MXPA01007577A (en) | Methods for separating a tocopherol from a tocopherol-containing mixture and compositions thereof | |
| JP2003508345A (ja) | トコフェロール含有混合物からトコフェロールを分離するための方法およびその組成物 | |
| ES2959817T3 (es) | Procedimiento para la preparación de tocoles y escualeno |