JPS61151186A - トコトリエノ−ル類およびトコフエロ−ル類の濃縮法 - Google Patents
トコトリエノ−ル類およびトコフエロ−ル類の濃縮法Info
- Publication number
- JPS61151186A JPS61151186A JP27075884A JP27075884A JPS61151186A JP S61151186 A JPS61151186 A JP S61151186A JP 27075884 A JP27075884 A JP 27075884A JP 27075884 A JP27075884 A JP 27075884A JP S61151186 A JPS61151186 A JP S61151186A
- Authority
- JP
- Japan
- Prior art keywords
- tocopherols
- tocotrienols
- tocopherol
- contact
- distillate
- 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.)
- Granted
Links
- 229930003799 tocopherol Natural products 0.000 title claims abstract description 34
- 239000011732 tocopherol Substances 0.000 title claims abstract description 34
- 229930003802 tocotrienol Natural products 0.000 title claims abstract description 30
- 239000011731 tocotrienol Substances 0.000 title claims abstract description 30
- 235000019148 tocotrienols Nutrition 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 22
- 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 title abstract description 10
- 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 title abstract description 10
- 235000010384 tocopherol Nutrition 0.000 title abstract description 8
- 229960001295 tocopherol Drugs 0.000 title abstract description 8
- 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 abstract description 6
- 239000003463 adsorbent Substances 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000741 silica gel Substances 0.000 claims abstract description 8
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 8
- 238000005192 partition Methods 0.000 claims abstract description 7
- 230000001877 deodorizing effect Effects 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims abstract description 5
- 235000021588 free fatty acids Nutrition 0.000 claims abstract description 5
- 239000003921 oil Substances 0.000 claims abstract description 5
- 239000003925 fat Substances 0.000 claims abstract description 4
- 125000002640 tocopherol group Chemical class 0.000 claims description 26
- 235000019149 tocopherols Nutrition 0.000 claims description 26
- 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 claims description 24
- 229940068778 tocotrienols Drugs 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 235000013305 food Nutrition 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003957 anion exchange resin Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- -1 distillation Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000019482 Palm oil Nutrition 0.000 description 3
- 235000019774 Rice Bran oil Nutrition 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000002540 palm oil Substances 0.000 description 3
- 239000008165 rice bran oil Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000010497 wheat germ oil Substances 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
- 229930182558 Sterol Natural products 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 229940064063 alpha tocotrienol Drugs 0.000 description 1
- 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 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 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
- 239000003054 catalyst Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 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
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000005194 fractionation Methods 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
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 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 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000019145 α-tocotrienol Nutrition 0.000 description 1
- 239000011730 α-tocotrienol Substances 0.000 description 1
- 235000019151 β-tocotrienol Nutrition 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
Landscapes
- Pyrane Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27075884A JPS61151186A (ja) | 1984-12-24 | 1984-12-24 | トコトリエノ−ル類およびトコフエロ−ル類の濃縮法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27075884A JPS61151186A (ja) | 1984-12-24 | 1984-12-24 | トコトリエノ−ル類およびトコフエロ−ル類の濃縮法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61151186A true JPS61151186A (ja) | 1986-07-09 |
| JPH0524914B2 JPH0524914B2 (enrdf_load_stackoverflow) | 1993-04-09 |
Family
ID=17490575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27075884A Granted JPS61151186A (ja) | 1984-12-24 | 1984-12-24 | トコトリエノ−ル類およびトコフエロ−ル類の濃縮法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61151186A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002501915A (ja) * | 1998-01-29 | 2002-01-22 | イーストマン ケミカル カンパニー | トコール含有混合物からのトコールの分離方法 |
| EP1336610A4 (en) * | 2000-11-21 | 2006-05-17 | Organo Corp | PROCESS FOR THE CHROMATOGRAPHIC MANUFACTURE OF TOCOTRIENOL |
-
1984
- 1984-12-24 JP JP27075884A patent/JPS61151186A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002501915A (ja) * | 1998-01-29 | 2002-01-22 | イーストマン ケミカル カンパニー | トコール含有混合物からのトコールの分離方法 |
| JP2002501916A (ja) * | 1998-01-29 | 2002-01-22 | イーストマン ケミカル カンパニー | 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 |
| EP1336610A4 (en) * | 2000-11-21 | 2006-05-17 | Organo Corp | PROCESS FOR THE CHROMATOGRAPHIC MANUFACTURE OF TOCOTRIENOL |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0524914B2 (enrdf_load_stackoverflow) | 1993-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| EXPY | Cancellation because of completion of term |