JPS58180480A - Separation of tocopherol - Google Patents
Separation of tocopherolInfo
- Publication number
- JPS58180480A JPS58180480A JP6204682A JP6204682A JPS58180480A JP S58180480 A JPS58180480 A JP S58180480A JP 6204682 A JP6204682 A JP 6204682A JP 6204682 A JP6204682 A JP 6204682A JP S58180480 A JPS58180480 A JP S58180480A
- Authority
- JP
- Japan
- Prior art keywords
- organic solvent
- tocopherol
- bagasse
- stem
- sugar cane
- 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
- 239000011732 tocopherol Substances 0.000 title claims abstract description 14
- 229930003799 tocopherol Natural products 0.000 title claims abstract description 13
- 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 12
- 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
- 229960001295 tocopherol Drugs 0.000 title abstract description 9
- 235000010384 tocopherol Nutrition 0.000 title abstract description 8
- 238000000926 separation method Methods 0.000 title 1
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 240000000111 Saccharum officinarum Species 0.000 claims abstract description 8
- 235000007201 Saccharum officinarum Nutrition 0.000 claims abstract description 8
- 241000609240 Ambelania acida Species 0.000 claims abstract description 6
- 239000010905 bagasse Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 235000019149 tocopherols Nutrition 0.000 claims description 5
- 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 5
- 239000000126 substance Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 8
- 150000002576 ketones Chemical class 0.000 abstract description 4
- 238000001035 drying Methods 0.000 abstract description 3
- 238000005194 fractionation Methods 0.000 abstract description 3
- 239000003921 oil Substances 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 238000004440 column chromatography Methods 0.000 abstract description 2
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 239000003925 fat Substances 0.000 abstract description 2
- 238000003306 harvesting Methods 0.000 abstract description 2
- 238000000199 molecular distillation Methods 0.000 abstract description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract description 2
- 239000003963 antioxidant agent Substances 0.000 abstract 2
- 230000003078 antioxidant effect Effects 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 230000000776 anti-sterility effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000005342 ion exchange Methods 0.000 abstract 1
- 230000003449 preventive effect Effects 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 235000010382 gamma-tocopherol Nutrition 0.000 description 3
- 239000002478 γ-tocopherol Substances 0.000 description 3
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229940087168 alpha tocopherol Drugs 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 235000010389 delta-tocopherol Nutrition 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229960000984 tocofersolan Drugs 0.000 description 2
- 235000004835 α-tocopherol Nutrition 0.000 description 2
- 239000002076 α-tocopherol Substances 0.000 description 2
- 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 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 241001456553 Chanodichthys dabryi Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 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 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000012544 Viola sororia Nutrition 0.000 description 1
- 241001106476 Violaceae Species 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- CDXSJGDDABYYJV-UHFFFAOYSA-N acetic acid;ethanol Chemical compound CCO.CC(O)=O CDXSJGDDABYYJV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002871 fertility agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000011521 glass Substances 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
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- -1 methyl oxate Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000007858 starting material Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- WGVKWNUPNGFDFJ-UHFFFAOYSA-N β-tocopherol group Chemical group CC1(OC2=C(C=C(C(=C2CC1)C)O)C)CCCC(CCCC(CCCC(C)C)C)C WGVKWNUPNGFDFJ-UHFFFAOYSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
- 150000003789 δ-tocopherols Chemical class 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明はサトウキビの葉並びにバガス中に含まれるトコ
フェロール類の分離方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for separating tocopherols contained in sugarcane leaves and bagasse.
トコフェロール類はビタミンＥ活性を有し、動物の抗不
妊薬として利用されてきたが、最近不飽和脂肪酸を含有
する油脂の酸化防止、成人病の予防、老化の防止等の作
用が明らかになり、食品添加物、医薬品、栄養食品及び
化粧品等への需要が急速に増大している。Tocopherols have vitamin E activity and have been used as anti-infertility drugs for animals, but recently it has been revealed that they have the ability to prevent the oxidation of fats and oils containing unsaturated fatty acids, prevent adult diseases, and prevent aging. Demand for food additives, pharmaceuticals, nutritional foods, cosmetics, etc. is rapidly increasing.
本発明者らはサトウキビの菫を粉砕又は細断したもの並
びにバガスを乾燥す“るか又はしないで、アルコール、
エーテル、ケトン、低級酸等の有機溶剤を単独又は混合
したもので抽出するか、これらの有機溶剤と水不溶性有
機溶剤との混合溶剤を用いて抽出することにより、トコ
フェロ−ルミｔ分離し得ることを見出した。さらに、こ
の抽出物について、低温分別、カラムクロマトグラフィ
ー、イオン交換クロマトグラフィー並びに分子蒸留等を
単独又は組合せて用いることにより、トコフェロール類
を濃縮し得ることを見出した。The present inventors have prepared crushed or shredded sugarcane violets and bagasse with or without drying, alcohol,
Tocopherol can be separated by extraction with an organic solvent such as ether, ketone, lower acid, etc. alone or in combination, or by extraction with a mixed solvent of these organic solvents and a water-insoluble organic solvent. I found out. Furthermore, it has been found that tocopherols can be concentrated in this extract by using low temperature fractionation, column chromatography, ion exchange chromatography, molecular distillation, etc. alone or in combination.
−トコフェロールが主成分で、次にγ−トコフェロール
が多量に含まれている。β−及びδ−トコフェロールは
少量成分である。-Tocopherol is the main component, followed by γ-tocopherol. β- and δ-tocopherols are minor components.
本発明の出発物質はサトウキビの菫で、生育中並並びに
収穫後の菫を含むものである。また、製糖工程中のサト
ウキビの菫及び製糖工程終了後のバガスが含まれる。The starting material of the present invention is sugarcane violet, including violet during growth as well as after harvest. It also includes sugarcane violet during the sugar refining process and bagasse after the sugar refining process.
本発明によれば、メタノール、エタノール、イソプロパ
ツール等のアルコール、エチルエーテル、イソプロピル
エーテル等のエーテル、アセトン、メチルエチルケトン
等のケトン、キ酸メチル、酢酸メチル、酢酸エチル等の
カルボン酸エステル、石油エーテル、ヘキサン、ヘプタ
ン、ベンゼン、トルエン及びギシレン等の炭化水素及び
クロロホルム、塩化メチレン、塩化エチレン等のハロゲ
ン化炭化水素等の有機溶剤を単独又は混合して、油温分
別を行い、可溶部にトコフェロール類の濃縮物が得られ
る。According to the present invention, alcohols such as methanol, ethanol, and isopropanol; ethers such as ethyl ether and isopropyl ether; ketones such as acetone and methyl ethyl ketone; carboxylic acid esters such as methyl oxate, methyl acetate, and ethyl acetate; petroleum ethers; , organic solvents such as hydrocarbons such as hexane, heptane, benzene, toluene, and ghylene, and halogenated hydrocarbons such as chloroform, methylene chloride, ethylene chloride, etc., alone or in combination, are subjected to oil temperature fractionation, and tocopherol is added to the soluble portion. Concentrates of the following types are obtained.
壕だ、本発明における抽出物を無極性有機溶剤に溶解し
、シリカ又はアルミナを充填したカラムに流し、続いて
、アルコール、エーテル、ケトン、エステル、芳香族化
合物及び有機塩素化物等を単独又は混合溶液として流し
、後者の流出区分から溶剤を除去して、残留物中にトコ
フェロール濃縮物を得ることができる。However, the extract in the present invention is dissolved in a nonpolar organic solvent and passed through a column packed with silica or alumina, and then alcohol, ether, ketone, ester, aromatic compound, organic chloride, etc. are dissolved alone or in a mixture. It is possible to run it as a solution and remove the solvent from the latter effluent section to obtain a tocopherol concentrate in the residue.
」二記方法のアルミナ又はシリカの代りに、イオン交換
樹脂をカラムにつめ、これに抽出物の有機溶剤の溶液を
流し、続いて、酸性の有機溶剤の溶液を流して得られる
区分を水洗、蒸留し、溶剤を除去後、トコフェロール類
が濃縮された残留物を得る。``In place of alumina or silica in method 2, fill a column with ion exchange resin, pour an organic solvent solution of the extract into the column, then pour an acidic organic solvent solution through the column, wash the resulting section with water, After distillation and removal of the solvent, a residue enriched in tocopherols is obtained.
さらに、本発明における抽出物は】０−２〜１０−３実
施例１゜
バガス］、 Ｏｋｇにヘキサン５０１を加え、３０〜５
０℃で良く振り捷ぜた。次に、ヘキサン溶液を日別。Further, the extract in the present invention is 0-2 to 10-3 Example 1゜bagasse], 30 to 5
Shake well at 0°C. Next, dilute the hexane solution.
し、ヘキサンを留去した。残渣３４ ｇを得た。この残
渣中にはα−トコフェロール４０００μｇ／ｇ及びγ−
トコフェロール１２００μｇ／ｇと１ＪＨｔ（Ｄβ−及
びδ−トコフェロールが含まれていた。Then, hexane was distilled off. 34 g of residue was obtained. This residue contains 4000 μg/g of α-tocopherol and γ-
Tocopherol 1200 μg/g and 1 JHt (Dβ- and δ-tocopherol were included).
この残渣３Ｃ１をアセトン１．５０ｍ１に溶解し７、−
２０″Ｃに冷却し、可溶部を分取した。可溶部からアセ
トンを留去し、残留物約５ｇを得た。この残留物はα−
トコフェロール、４７，５００μｇ／ｇ及びγ−トコフ
ェロール、６，６００μｇｌ＆、合計５４，１００μ９
／ｇを含有していた。This residue 3C1 was dissolved in 1.50ml of acetone and 7,-
It was cooled to 20"C and the soluble part was separated. Acetone was distilled off from the soluble part to obtain about 5 g of a residue. This residue was α-
Tocopherol, 47,500μg/g and γ-tocopherol, 6,600μgl & total 54,100μ9
/g.
実施例２゜
バガス］、 ＯｋｇＫクロロホルム、メタノール（２：
１）混合溶液１００１を加え、室温で振とう腰桶た。Example 2゜bagasse], OkgK chloroform, methanol (2:
1) Add mixed solution 1001 and shake at room temperature.
この残留物をエタノールに溶解腰これをＯＨ型塩基性陰
イオン交換樹脂アンノく一うイトＩ ＲＡ、４．０１を
径５ｃｍ、長さ６０ｃｍのガラス製クロマト管に３０鑞
の高さに充填した層に流し、トコフェロールを吸着させ
た後、２００ｍｌのヘキサンを流した。次に、５φ酢酸
工タノール５０ｍｌを流し７、流ｆｆｉ液から溶剤を留
去し、トコフェロール濃縮物０．２，！ｉ＋（純度３５
％）を得た。This residue was dissolved in ethanol, and OH-type basic anion exchange resin Annotite IRA, 4.01 was filled into a glass chromatography tube with a diameter of 5 cm and a length of 60 cm to a height of 30 mm. After pouring into the layer and adsorbing tocopherol, 200 ml of hexane was poured. Next, 50 ml of 5φ acetic acid ethanol was poured into the stream 7, and the solvent was distilled off from the flowing ffi liquid, resulting in a tocopherol concentrate of 0.2,! i+ (purity 35
%) was obtained.
実施例３
ザトウキビのｆｆｉ ５ ｋｇを細断し、ヘキサン、エ
タノール（］：］）混合溶液（５７Ｘ３）を用いて抽出
した。抽出溶液から溶剤を留去後、残留物にヘキサン２
００ｍ１！を加え、ヘキサン可溶部を分取した。次に、
ヘキサンを留去し、残留物５ｇを得た。Example 3 5 kg of humpback ffi was shredded and extracted using a mixed solution (57×3) of hexane and ethanol (]:]). After distilling off the solvent from the extraction solution, add hexane 2 to the residue.
00m1! was added, and the hexane-soluble portion was separated. next,
Hexane was distilled off to obtain 5 g of residue.
Claims (1)
類を分離する方法において、該物質を有機溶剤の単独又
は混合物を用いて、抽出処理することを特徴とするトコ
フェロールの分離方法。(1) A method for separating tocopherols from sugarcane and bagasse, which comprises extracting the substance using an organic solvent alone or in a mixture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6204682A JPS58180480A (en) | 1982-04-14 | 1982-04-14 | Separation of tocopherol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6204682A JPS58180480A (en) | 1982-04-14 | 1982-04-14 | Separation of tocopherol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58180480A true JPS58180480A (en) | 1983-10-21 |
Family
ID=13188823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6204682A Pending JPS58180480A (en) | 1982-04-14 | 1982-04-14 | Separation of tocopherol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58180480A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59161372A (en) * | 1983-03-01 | 1984-09-12 | Azuma Shibue | Concentration of vitamin e |
| JPS6153280A (en) * | 1984-08-02 | 1986-03-17 | ヘンケル・コーポレイション | Purification of tocopherol by extraction |
| FR2669032A1 (en) * | 1990-11-14 | 1992-05-15 | Cecchi Georges | Process for the manufacture of a d- alpha -tocopherol preparation |
| CN106317007A (en) * | 2015-06-15 | 2017-01-11 | 浙江医药股份有限公司新昌制药厂 | Method for recovery of d-alpha-tocopherol from natural vitamin E leftover material |
-
1982
- 1982-04-14 JP JP6204682A patent/JPS58180480A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59161372A (en) * | 1983-03-01 | 1984-09-12 | Azuma Shibue | Concentration of vitamin e |
| JPS6124393B2 (en) * | 1983-03-01 | 1986-06-10 | Azuma Shibue | |
| JPS6153280A (en) * | 1984-08-02 | 1986-03-17 | ヘンケル・コーポレイション | Purification of tocopherol by extraction |
| FR2669032A1 (en) * | 1990-11-14 | 1992-05-15 | Cecchi Georges | Process for the manufacture of a d- alpha -tocopherol preparation |
| CN106317007A (en) * | 2015-06-15 | 2017-01-11 | 浙江医药股份有限公司新昌制药厂 | Method for recovery of d-alpha-tocopherol from natural vitamin E leftover material |
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