JPH0524914B2 - - Google Patents
Info
- Publication number
- JPH0524914B2 JPH0524914B2 JP27075884A JP27075884A JPH0524914B2 JP H0524914 B2 JPH0524914 B2 JP H0524914B2 JP 27075884 A JP27075884 A JP 27075884A JP 27075884 A JP27075884 A JP 27075884A JP H0524914 B2 JPH0524914 B2 JP H0524914B2
- Authority
- JP
- Japan
- Prior art keywords
- tocotrienols
- tocopherols
- distillate
- brought
- solvent
- 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
- 229930003799 tocopherol Natural products 0.000 claims description 29
- 239000011732 tocopherol Substances 0.000 claims description 29
- 229930003802 tocotrienol Natural products 0.000 claims description 28
- 239000011731 tocotrienol Substances 0.000 claims description 28
- 235000019148 tocotrienols Nutrition 0.000 claims description 28
- 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 26
- 229940068778 tocotrienols Drugs 0.000 claims description 26
- 125000002640 tocopherol group Chemical class 0.000 claims description 25
- 235000019149 tocopherols Nutrition 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 13
- 239000003463 adsorbent Substances 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000741 silica gel Substances 0.000 claims description 7
- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000001877 deodorizing effect Effects 0.000 claims description 4
- 235000021588 free fatty acids Nutrition 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 238000005192 partition Methods 0.000 claims description 4
- 239000003925 fat Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 6
- 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
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 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
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 235000010384 tocopherol Nutrition 0.000 description 4
- 229960001295 tocopherol Drugs 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
- -1 fatty acid esters Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 235000019198 oils Nutrition 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
- GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-UHFFFAOYSA-N 0.000 description 2
- 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
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 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
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-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
- 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
- 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
- 239000000203 mixture Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 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
- 238000001179 sorption measurement Methods 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
Description
【発明の詳細な説明】
(a) 産業上の利用分野
本発明はトコトリエノール類とトコフエロール
類が共存する原料から、この両者を高純度に分離
精製する方法に係る。DETAILED DESCRIPTION OF THE INVENTION (a) Field of Industrial Application The present invention relates to a method for separating and refining tocotrienols and tocopherols to high purity from raw materials in which they coexist.
(b) 従来の技術
トコフエロール類は多くの油脂に通常１％以下
の含量で含まれており、ビタミンＥとして医薬品
に、また抗酸化剤として食品に、広く利用されて
いる。トコフエロールの類縁の物質としては側鎖
に二重結合を３個有するトコトリエノールが知ら
れており、種々の研究からトコフエロールと同様
の効果を有することが明らかになると同時にトコ
フエロールの欠点を補う性質も見出されたことか
らトコトリエノールの重要性は増大することきが
予想される。(b) Prior Art Tocopherols are contained in many oils and fats, usually in a content of 1% or less, and are widely used in medicines as vitamin E and in foods as antioxidants. Tocotrienol, which has three double bonds in its side chain, is known as a substance related to tocopherol, and various studies have revealed that it has the same effects as tocopherol, and at the same time, it has also been found to have properties that compensate for the shortcomings of tocopherol. As a result, the importance of tocotrienols is expected to increase.
多くの油脂はトコフエロール類のみを含有する
がトコトリエノールはパーム油、米ぬか油、小麦
胚芽油等にトコフエロールと共存している。 Many fats and oils contain only tocopherols, but tocotrienols coexist with tocopherols in palm oil, rice bran oil, wheat germ oil, etc.
トコトリエノール類はその挙動がトコフエロー
ルと著しく類似するためこれらの油からトコトリ
エノール又はトコフエロールの高純度濃縮物を工
業的に製造することが困難であり、必然的に処理
コストが高くなる欠点を有している。 The behavior of tocotrienols is strikingly similar to that of tocopherols, so it is difficult to industrially produce high-purity concentrates of tocotrienols or tocopherols from these oils, which inevitably results in high processing costs. .
特公昭59−34191号公報および特公昭59−34192
号公報にはトコフエロール類およびトコトリエノ
ール類の濃縮法が開示されているが、これらは両
者の混合物を濃縮する方法であつて、これまで両
者を分離して濃縮する有効な方法は知られていな
い。 Special Publication No. 59-34191 and Special Publication No. 59-34192
Although the publication discloses a method for concentrating tocopherols and tocotrienols, these are methods for concentrating a mixture of the two, and so far no effective method for separating and concentrating the two has been known.
(c) 発明が解決しようとする問題点
本発明の目的は、上記の欠点を払拭し、トコト
リエノールおよびトコフエロールを低コストで高
純度に分離濃縮する方法を提供することにある。(c) Problems to be Solved by the Invention An object of the present invention is to eliminate the above-mentioned drawbacks and provide a method for separating and concentrating tocotrienols and tocopherols with high purity at low cost.
(d) 問題点を解決するための手段
本発明者らは、鋭意研究の結果、特定の吸着剤
を用いることによつて、前記の目的が達成される
ことを見い出した。(d) Means for Solving the Problems As a result of intensive research, the present inventors have discovered that the above object can be achieved by using a specific adsorbent.
本発明は、かかる知見に基づいて完成されたも
ので、トコトリエノール類およびトコフエロール
類が共存する油脂の脱臭工程または蒸留脱酸工程
で得られる留出物を逆相分配型吸着剤と接触させ
たのち、溶媒と接触させてトコトリエノール類と
トコフエロール類を順次抽出することを特徴とす
るトコトリエノール類およびトコフエロール類の
濃縮法である。 The present invention has been completed based on this knowledge, and involves contacting a distillate obtained in a deodorizing process or a distillation deacidification process of fats and oils in which tocotrienols and tocopherols coexist with a reverse phase partition type adsorbent. , a method for concentrating tocotrienols and tocopherols, which is characterized by sequentially extracting tocotrienols and tocopherols by contacting them with a solvent.
本発明の出発物質はパーム油、米ぬか油、小麦
胚芽油等の脱臭工程または蒸留脱酸工程における
留出物である。 The starting material of the present invention is a distillate of palm oil, rice bran oil, wheat germ oil, etc. in a deodorizing process or distillation deacidification process.
この留出物中の遊離脂肪酸が多い場合は、逆相
分配型吸着剤処理に先立ち、陰イオン交換樹脂、
蒸留、溶剤分別等の手段により遊離脂肪酸を除去
することが好ましい。 If this distillate contains a large amount of free fatty acids, an anion exchange resin,
It is preferable to remove free fatty acids by means such as distillation or solvent fractionation.
陰イオン交換樹脂を用いる操作例を示せば次の
通りである。即ち留出物はまず一価アルコールを
用いてエステル化処理する。一価アルコールとし
ては通常メタノールまたはエタノールが用いられ
る。エステル化触媒としては硫酸等が用いられ
る。 An example of operation using an anion exchange resin is as follows. That is, the distillate is first esterified using a monohydric alcohol. Methanol or ethanol is usually used as the monohydric alcohol. Sulfuric acid or the like is used as the esterification catalyst.
前記で得られたエステル化物は陰イオン交換樹
脂と接触させて処理物中に含まれるトコトリエノ
ールおよびトコフエロール類を吸着させる。 The esterified product obtained above is brought into contact with an anion exchange resin to adsorb tocotrienols and tocopherols contained in the treated product.
次ぎに吸着剤を溶媒に接触させて脂肪酸エステ
ルを抽出する。この場合の溶媒として水を含まな
いエタノールが用いられる。つづいて第２の溶媒
として水を含むエタノールと接触させてトコトリ
エノール類およびトコフエロールを同時に抽出す
る。得られた抽出液は減圧下で溶媒を除く。 Next, the adsorbent is brought into contact with a solvent to extract fatty acid esters. In this case, water-free ethanol is used as the solvent. Subsequently, tocotrienols and tocopherols are simultaneously extracted by contacting with ethanol containing water as a second solvent. The solvent is removed from the obtained extract under reduced pressure.
なお遊離脂肪酸の除去方法は、上記に限定され
ない。 Note that the method for removing free fatty acids is not limited to the above.
前述の留出物をまたは上記の処理を行つた留出
物を、次ぎに逆相分配型吸着剤と接触させる。逆
相分配型吸着剤としては炭素数６ないし28のアル
キル基を化学的に結合したシリカゲルが好まし
く、ほかにアミノプロピル基、シアノプロピル
基、フエニル基を結合させたもの等を使用でき
る。 The above-mentioned distillate or the above-treated distillate is then contacted with a reverse phase distribution type adsorbent. As the reverse phase distribution type adsorbent, silica gel to which an alkyl group having 6 to 28 carbon atoms is chemically bonded is preferred, and silica gel to which an aminopropyl group, cyanopropyl group, or phenyl group is bonded can also be used.
この操作により、被処理物を吸着剤に吸着させ
たのち溶媒と接触させて、まずトコトリエノール
類を抽出し、続いてトコフエロール類を抽出す
る。用いる溶媒としては、メタノール、エタノー
ル等の低級アルカノールもしくはアセトニトリル
等の極性の強い溶媒、またはこれらとクロロホル
ム、塩化メチレン、テトラヒドロフラン等の極性
の弱い溶媒との混合溶媒が適当である。トコトリ
エノール類およびトコフエロール類の抽出される
区分は、種々条件により異なるが、一般にはトコ
トリエノール類は吸着剤の３〜６倍量、トコフエ
ロール類は10〜30倍量用いたときに抽出される。 Through this operation, the material to be treated is adsorbed on the adsorbent and then brought into contact with a solvent to first extract tocotrienols and then tocopherols. Suitable solvents are lower alkanols such as methanol and ethanol, highly polar solvents such as acetonitrile, or mixed solvents of these with weakly polar solvents such as chloroform, methylene chloride, and tetrahydrofuran. The categories in which tocotrienols and tocopherols are extracted vary depending on various conditions, but in general, tocotrienols are extracted when 3 to 6 times the amount of the adsorbent is used, and tocopherols are extracted when 10 to 30 times the amount of the adsorbent is used.
なおトコトリエノール区分およびトコフエロー
ル区分はステロール、炭化水素、脂肪酸などの不
純物を含むことがあるが、この場合逆相分配型吸
着剤処理の前又は後に不純物を含む区分を例えば
シリカゲルと接触させて吸着させたのち５〜20％
のエチルエーテルを含有するヘキサンでトコトリ
エノール類および／またはトコフエロール類を抽
出する方法等により不純物を除くことができる。 Note that the tocotrienol fraction and tocopherol fraction may contain impurities such as sterols, hydrocarbons, and fatty acids; in this case, the fraction containing impurities is adsorbed by contacting with silica gel, for example, before or after treatment with a reversed-phase partition type adsorbent. 5-20% later
Impurities can be removed by a method such as extracting tocotrienols and/or tocopherols with hexane containing ethyl ether.
実施例 １
米ぬか油を精製する際の脱臭工程で得られる留
出物10Kgに１％の硫酸を含むメタノール10Kgを加
え１時間加熱したのち、メタノールの大部分を減
圧下で留去する。残留物を水洗、脱水後陰イオン
交換樹脂５をつめたカラムに供して吸着させた
のち99.5％エタノール30を流して大部分の脂肪
酸メチルを溶出する。つづいて94％含水エタノー
ル20を流して、その区分を集め減圧下で脱溶剤
して抽出物442ｇを得た。この区分はトコトリエ
ノール類15.5％、トコフエロール類14.0％を含有
していた。Example 1 10 kg of methanol containing 1% sulfuric acid was added to 10 kg of the distillate obtained in the deodorizing step during the refining of rice bran oil, and after heating for 1 hour, most of the methanol was distilled off under reduced pressure. After washing the residue with water and dehydrating it, it is applied to a column filled with anion exchange resin 5 for adsorption, and then 99.5% ethanol 30 is passed through it to elute most of the fatty acid methyl. Subsequently, 20 g of 94% aqueous ethanol was poured into the flask, and the fractions were collected and the solvent was removed under reduced pressure to obtain 442 g of an extract. This category contained 15.5% tocotrienols and 14.0% tocopherols.
つぎにこの溶出物を炭素数18のアルキル基を化
学的に結合したシリカゲル５を充テンしたカラ
ムに供して吸着させ、アセトニトリルを流して20
〜25（区分１）および30〜45（区分２）の区
分を集める。区分１および区分２を減圧下で脱溶
媒して区分１はα−トコトリエノールおよびβ−
トコトリエノールの合計91％を含む抽出物31ｇ
を、また区分２はα−トコフエロールを85％含む
抽出物28.5ｇを得た。 Next, this eluate was adsorbed on a column filled with silica gel 5 to which alkyl groups having 18 carbon atoms were chemically bonded, and acetonitrile was passed through the column for 20
Collect categories ~25 (category 1) and 30-45 (category 2). Section 1 and Section 2 were desolvated under reduced pressure to give Section 1 α-tocotrienol and β-tocotrienol.
31g extract containing 91% total tocotrienols
In Category 2, 28.5 g of extract containing 85% α-tocopherol was obtained.
実施例 ２
パーム油を蒸留脱酸する際に得られる留出物10
Kgに１％硫酸を含むメタノール10Kgを加え１時間
加熱したのち、メタノールの大部分を減圧下で留
去する。残留物を水洗、脱水後陰イオン交換樹脂
５をつめたカラムに供して吸着させたのち、
99.5％エタノール30を流して大部分の脂肪酸メ
チルを溶出させる。つづいて94％含水エタノール
20を流してその区分を集め減圧下で脱溶剤して
抽出物(1)825ｇを得た。この区分はトコトリエノ
ール類4.5％、トコフエロール類5.3％を含有して
いた。Example 2 Distillate 10 obtained during distillation deacidification of palm oil
After adding 10 kg of methanol containing 1% sulfuric acid to kg and heating for 1 hour, most of the methanol is distilled off under reduced pressure. After washing the residue with water and dehydrating it, it was subjected to a column packed with anion exchange resin 5 to be adsorbed.
Flow 99.5% ethanol 30 to elute most of the fatty acid methyl. Next, 94% hydrated ethanol
20 was poured, the fractions were collected, and the solvent was removed under reduced pressure to obtain 825 g of extract (1). This category contained 4.5% tocotrienols and 5.3% tocopherols.
抽出物(1)をシリカゲルカラム10をつめたカラ
ムに供し吸着させ５％エチルエーテル含有ヘキサ
ン30を流しその区分を集める。減圧下で脱溶媒
して101ｇの抽出物(2)を得た。この抽出物(2)はト
コトリエノール類44％およびトコフエロール類36
％を含有していた。 The extract (1) is applied to a column packed with silica gel column 10 to adsorb it, and then 30 g of hexane containing 5% ethyl ether is passed through the column and the fraction is collected. The solvent was removed under reduced pressure to obtain 101 g of extract (2). This extract (2) contains 44% tocotrienols and 36% tocopherols.
It contained %.
つづいて抽出物(2)を炭素数８のアルキル基を化
学的に結合したシリカゲル５を充テンしたカラ
ムに供して吸着させ、エタノールを流して15〜30
（区分１）および30〜50（区分２）の区分を
集める。区分１および区分２を減圧下で脱溶媒し
て区分１はトコトリエノール類98％を含む抽出物
43ｇおよび区分２はトコフエロール類95％を含む
抽出物33ｇを得た。 Next, the extract (2) was adsorbed on a column filled with silica gel 5, in which alkyl groups having 8 carbon atoms were chemically bonded, and ethanol was passed through the column for 15 to 30 minutes.
(Category 1) and 30 to 50 (Category 2). After removing the solvent from Category 1 and Category 2 under reduced pressure, Category 1 is an extract containing 98% tocotrienols.
43g and Category 2 yielded 33g of extract containing 95% tocopherols.
(e) 発明の効果
トコトリエノール類およびトコフエロール類
は、共に医薬品、食品等として有用な物質である
が、両者はその挙動が互いに著しく類似している
ため、両者を含む物質から夫々を高純度で分離す
ることは困難であつた。(e) Effects of the invention Tocotrienols and tocopherols are both useful substances as medicines, foods, etc., but since their behavior is extremely similar to each other, it is necessary to separate each of them with high purity from substances containing both. It was difficult to do so.
しかし本発明によれば、この両者を高純度に分
離濃縮することができ、また処理コストも安くて
すむから、工業的な実施が可能である。 However, according to the present invention, both of these can be separated and concentrated to a high degree of purity, and the processing cost is low, so that industrial implementation is possible.
Claims (1)
が共存する油脂の脱臭工程または蒸留脱酸工程で
得られる留出物を、逆相分配型吸着剤と接触させ
たのち、溶媒と接触させてトコトリエノール類と
トコフエロール類を順次抽出することを特徴とす
るトコトリエノール類およびトコフエロール類の
濃縮法。 ２ 逆相分配型吸着剤が、炭素数６ないし28のア
ルキル基を化学的に結合したシリカゲルである特
許請求の範囲第１項記載の濃縮法。 ３ 留出物中の遊離脂肪酸を除去したのち逆相分
配型吸着剤と接触させる特許請求の範囲第１項ま
たは第２項記載の濃縮法。[Scope of Claims] 1. A distillate obtained in a deodorizing process or distillation deacidification process of fats and oils in which tocotrienols and tocopherols coexist is brought into contact with a reversed phase distribution type adsorbent, and then brought into contact with a solvent to produce tocotrienols. A method for concentrating tocotrienols and tocopherols, the method comprising sequentially extracting tocotrienols and tocopherols. 2. The concentration method according to claim 1, wherein the reversed phase partition type adsorbent is silica gel to which alkyl groups having 6 to 28 carbon atoms are chemically bonded. 3. The concentration method according to claim 1 or 2, wherein after free fatty acids in the distillate are removed, the distillate is brought into contact with a reverse phase partition type adsorbent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27075884A JPS61151186A (en) | 1984-12-24 | 1984-12-24 | Method of concentrating tocotrienol and tocopherol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27075884A JPS61151186A (en) | 1984-12-24 | 1984-12-24 | Method of concentrating tocotrienol and tocopherol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61151186A JPS61151186A (en) | 1986-07-09 |
| JPH0524914B2 true JPH0524914B2 (en) | 1993-04-09 |
Family
ID=17490575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27075884A Granted JPS61151186A (en) | 1984-12-24 | 1984-12-24 | Method of concentrating tocotrienol and tocopherol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61151186A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1051412B1 (en) * | 1998-01-29 | 2003-09-24 | Eastman Chemical Company | Methods for separating a tocotrienol from a tocol-containing mixture and compositions thereof |
| JP2002153702A (en) * | 2000-11-21 | 2002-05-28 | Japan Organo Co Ltd | Preparative chromatography for tocotrienol |
-
1984
- 1984-12-24 JP JP27075884A patent/JPS61151186A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61151186A (en) | 1986-07-09 |
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