JPS6187796A - Concentration of highly unsaturated fatty acid - Google Patents
Concentration of highly unsaturated fatty acidInfo
- Publication number
- JPS6187796A JPS6187796A JP20837784A JP20837784A JPS6187796A JP S6187796 A JPS6187796 A JP S6187796A JP 20837784 A JP20837784 A JP 20837784A JP 20837784 A JP20837784 A JP 20837784A JP S6187796 A JPS6187796 A JP S6187796A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acids
- double bonds
- acid
- column
- highly unsaturated
- 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
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims description 9
- 150000004670 unsaturated fatty acids Chemical class 0.000 title claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 37
- 239000000194 fatty acid Substances 0.000 claims description 37
- 229930195729 fatty acid Natural products 0.000 claims description 37
- 150000004665 fatty acids Chemical class 0.000 claims description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000741 silica gel Substances 0.000 claims description 16
- 229910002027 silica gel Inorganic materials 0.000 claims description 16
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 claims description 15
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical group CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 claims description 15
- 235000020664 gamma-linolenic acid Nutrition 0.000 claims description 15
- 229960002733 gamolenic acid Drugs 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 11
- 239000010775 animal oil Substances 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 239000008158 vegetable oil Substances 0.000 claims description 7
- 238000012856 packing Methods 0.000 claims description 6
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 5
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical group CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 2
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 2
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- 239000012141 concentrate Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000002245 particle Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000010828 elution Methods 0.000 description 6
- 239000003925 fat Substances 0.000 description 5
- 235000019871 vegetable fat Nutrition 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 241000195649 Chlorella <Chlorellales> Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- -1 fatty acid ester Chemical class 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
（１）産業上の利用分野
本発明は、動植物油脂を原料として、分子内に二重結合
を３以上有する脂肪酸を高濃度かつ高収率で濃縮する方
法に関する。DETAILED DESCRIPTION OF THE INVENTION (1) Industrial Application Field The present invention relates to a method for concentrating fatty acids having three or more double bonds in the molecule at high concentration and yield using animal and vegetable oils and fats as raw materials.
（２）従来の技術
二重結合を分子内に３以上有する高度不飽和脂肪酸には
、ガンマ−リノレン酸をはじめとして生理的に活性なも
のが多くあり、食品の一成分として有用なばかりでな（
、医薬品原料や化粧品原料としても重要な物質である。(2) Prior art There are many highly unsaturated fatty acids that have three or more double bonds in their molecules that are physiologically active, including gamma-linolenic acid, and are useful as food ingredients. (
It is also an important substance as a raw material for pharmaceuticals and cosmetics.
しかしながら、これら生理的に活性な高度不飽和脂肪酸
は、天然には動植物油脂の構成成分として少量が存在す
るのみで、医薬品等の原料に供するためには高度の濃縮
が必要である。However, these physiologically active highly unsaturated fatty acids exist only in small amounts in nature as constituents of animal and vegetable oils and fats, and require a high degree of concentration in order to be used as raw materials for pharmaceuticals and the like.
従来、天然の油脂からガンマ−リノレン酸等を濃縮する
には、溶剤分別、蒸留などが多く用いられてきたが、こ
れらの方法では、飽和脂肪酸と高度不飽和脂肪酸の分離
には有効であるが、濃縮の対象の脂肪酸と不飽和度の近
い脂肪酸の混入が著しく、高濃度かつ高収率の濃縮は困
難であった。Conventionally, methods such as solvent fractionation and distillation have often been used to concentrate gamma-linolenic acid etc. from natural fats and oils, but although these methods are effective in separating saturated fatty acids and highly unsaturated fatty acids, However, the contamination of fatty acids with a similar degree of unsaturation to the fatty acids to be concentrated was significant, making it difficult to achieve high concentration and high yield concentration.
（３）発明が解決しようとする問題点
本発明の目的は、天然の動植物油脂を原料として、二重
結合を３以上有する脂肪酸を高濃度かっ高収率で濃縮す
る方法を提供することにある。(3) Problems to be Solved by the Invention An object of the present invention is to provide a method for concentrating fatty acids having three or more double bonds at high concentration and high yield using natural animal and vegetable oils and fats as raw materials. .
本発明が対象とする天然の動植物油脂は、二正結合数２
の脂肪酸と二重結合が３以上の脂肪酸とが混在している
ため、従来の方法では二重結合が３以上の脂肪酸を効率
的に濃縮することが困難であったものである。The natural animal and vegetable fats and oils targeted by the present invention have a dipositive bond number of 2.
Because these fatty acids and fatty acids with three or more double bonds coexist, it has been difficult to efficiently concentrate fatty acids with three or more double bonds using conventional methods.
（４）問題点を解決するための手段
本発明は動植物油脂由来の脂肪酸を、まずシリカゲルを
充填剤とするカラムに供し、次いでオクタデシル基を化
学的に結合したシリカゲル（以下これをＯＤＳという）
を充填剤とするカラムに供することを特徴とする、分子
内に二重結合を３以上有する高度不飽和脂肪酸の濃縮法
である。(4) Means for solving the problems The present invention first applies fatty acids derived from animal and vegetable oils to a column using silica gel as a packing material, and then uses silica gel (hereinafter referred to as ODS) to which octadecyl groups are chemically bonded.
This is a method for concentrating highly unsaturated fatty acids having three or more double bonds in the molecule, which is characterized by subjecting the polyunsaturated fatty acids to a column containing as a packing material.
本発明は、たとえば次のようにして実施することができ
るがこれに限定されるものではない。すなわち原料の動
植物油脂を常法によりエチルエステル又は脂肪酸にかえ
たのち、まずシリカゲルを充填剤とするカラムに供する
。この工程についてさらに詳しくのべると、エステルま
たは脂肪酸量の５〜ｌＯ倍量のシリカゲル（粒度３０〜
２００ｍｅｓｈ＋孔径７０〜２００人）をｎ−ヘキサン
に懸濁してカラムに流入し、シリカゲルカラムを調装す
る。つづいてエチルエステル又は脂肪酸を等量のｎ−ヘ
キサンに溶解してカラムの上端より供したのちシリカゲ
ルの重量の２０〜３０倍量のｎ−ヘキサン／エーテル＝
４００／１の組成を有する溶出液を２〜６時間で流す。The present invention can be implemented, for example, as follows, but is not limited thereto. That is, the raw animal and vegetable oils and fats are converted into ethyl esters or fatty acids by a conventional method, and then first subjected to a column using silica gel as a packing material. To explain this process in more detail, the amount of silica gel (particle size 30-10
Prepare a silica gel column by suspending 200 mesh + 70-200 mesh (pore size) in n-hexane and flowing into the column. Next, ethyl ester or fatty acid is dissolved in an equal amount of n-hexane and applied from the top of the column, and then the amount of n-hexane/ether is 20 to 30 times the weight of the silica gel.
The eluate with a composition of 400/1 is run in 2-6 hours.
この区分を除いたのちシリカゲルの５倍量のｎ−ヘキサ
ン／エーテル＝８０／２０の組成の溶出液を約１時間で
流しこの区分を集め減圧下で蒸留して溶出液を除き、−
次濃縮物とする。After removing this section, an eluate with a composition of n-hexane/ether = 80/20, which is 5 times the amount of silica gel, was poured for about 1 hour, and this section was collected and distilled under reduced pressure to remove the eluate.
Next, use it as a concentrate.
ついで−次濃縮物を次の条件でＯＤＳカラムに供し、先
に溶出する二重結合数３以上の目的とする脂肪酸を分取
する。すなわち粒度３０〜２００ａ＋ｅｓｈ、孔径７０
〜２００人、カーボン率２０％のＯＤＳを一次濃縮物の
８〜２０倍量準備し、エタノール／水−８０／２０また
はアセトニトリル／水＝７０／３０で流入してＯＤＳカ
ラムを調製する。−次濃縮物を等量のエタノールまたは
アセトニトリルに溶解してカラムに供し、エタノール／
水＝８５／１５またはアセトニトリル／水−８０／２０
の組成の溶出液を流す。充填剤の３倍量流すと、二重結
合数３以上の脂肪酸の溶出が始まり６倍量流し終るまで
の溶出液を集める。減圧下での蒸留により溶剤を除くと
、二重結合数３以上の脂肪酸を９０％以上含む濃縮物が
得られ、この濃縮物に目的とする脂肪酸の６０％以上が
集められる。Then, the second concentrate is applied to an ODS column under the following conditions, and the target fatty acid having three or more double bonds that is eluted first is fractionated. That is, particle size 30-200a+esh, pore size 70
~200 people, prepare 8 to 20 times the amount of ODS with a carbon content of 20% as the primary concentrate, and flow in ethanol/water - 80/20 or acetonitrile/water = 70/30 to prepare an ODS column. -The next concentrate was dissolved in an equal volume of ethanol or acetonitrile and applied to the column.
Water = 85/15 or acetonitrile/water - 80/20
Run an eluate with a composition of When 3 times the volume of the filler is flowed, the elution of fatty acids having 3 or more double bonds begins, and the eluate is collected until 6 times the volume of the filler has been flowed. When the solvent is removed by distillation under reduced pressure, a concentrate containing 90% or more of fatty acids having 3 or more double bonds is obtained, and 60% or more of the desired fatty acids are collected in this concentrate.
（５）作用
異なる２種類の充填剤を用いることにより、本発明のよ
うな好結果が得られる原理は次のように考えられる。第
１のシリカゲルカラムでは、脂肪酸の二重結合数の差に
より生ずる、シリカゲルに対する吸着力の差を利用し、
吸着力のやや小さい二重結合数２以下の脂肪酸の約１／
２を除き、つぎのＯＤＳカラムの分離性に対する負担を
軽減する。この工程で除かれる脂肪酸の割合は、二ｍ結
合数により異なり二重結合数Ｏでは９８％、１では６５
％、２では４０％、３では１５％である。(5) The principle by which the good results of the present invention can be obtained by using two types of fillers with different effects is considered as follows. The first silica gel column utilizes the difference in adsorption power to silica gel caused by the difference in the number of double bonds of fatty acids,
Approximately 1/2 of fatty acids with a double bond number of 2 or less, which has a slightly smaller adsorption power.
Except for 2, the load on the separation performance of the next ODS column is reduced. The proportion of fatty acids removed in this step varies depending on the number of 2m bonds, and is 98% when the number of double bonds is O, and 65% when the number of double bonds is 1.
%, 2 is 40%, and 3 is 15%.
この割合は原料の脂肪酸組成に依らず、はぼ一定である
。しかし溶出液の量又はエーテルの割合を増減すること
により、二重結合数３以上の溶出を調節することができ
る。This ratio is almost constant regardless of the fatty acid composition of the raw material. However, elution of 3 or more double bonds can be controlled by increasing or decreasing the amount of eluent or the proportion of ether.
表−１は大豆油について、シリカゲルカラム処理前後に
おける脂肪酸組成および収率を示すものである。表から
明らかなように、二重結合数３のリルン酸は、約１．８
倍に濃縮されている。この工程での濃縮率は、原料の脂
肪酸組成に大きく依在し、二重結合数０およびｌが多い
程、高い濃縮率が得られ、またそれを原料の脂肪酸組成
から、かなり正確に予想することができる。Table 1 shows the fatty acid composition and yield of soybean oil before and after silica gel column treatment. As is clear from the table, lylunic acid with 3 double bonds has approximately 1.8
It is twice as concentrated. The concentration rate in this process largely depends on the fatty acid composition of the raw material, and the higher the number of double bonds (0 and 1), the higher the concentration rate, and it can be predicted fairly accurately from the fatty acid composition of the raw material. be able to.
表−１大豆油中のリルン酸の濃縮 ・第２のＯＤＳ
カラムでは、脂肪酸の充填剤と溶出液に対する分配係数
の差を利用して、吸着力の差では十分に除去できない二
重結合数２の脂肪酸を除くことが、主な目的である。Ｏ
ＤＳカラムでは、脂肪酸の炭素数と二重結合数の間には
、下記の関係があり、ＥＣＮ値の小さい脂肪酸はど先に
ン容出する（ Ｅ ＣＮ ： Ｅｑｕｉｖａｌｅｎｔ
Ｃａｒｂｏｎ Ｎｕｍｂｅｒ等価炭素数）。Table-1 Concentration of lylunic acid in soybean oil ・Second ODS
The main purpose of the column is to utilize the difference in the distribution coefficient of fatty acids between the packing material and the eluate to remove fatty acids with two double bonds, which cannot be sufficiently removed due to the difference in adsorption power. O
In a DS column, there is the following relationship between the number of carbon atoms and the number of double bonds in fatty acids, and fatty acids with a small ECN value are ejected first (E CN: Equivalent
Carbon Number).
ＥＣＮ＝炭素数−２×二重結合数
したがって炭素数が同一ならば、二重結合数の多い脂肪
酸から先に溶出するため、二重結合数２以下の脂肪酸が
溶出する前に、二重結合数３以上の脂肪酸をとることが
できる。また二重結合数３以上の脂肪酸が２種以上含ま
れるものについても、ＥＣＮの大きさから溶出量を推定
することができるため、これらの脂肪酸同士の分画も可
能である。ECN = number of carbons - 2 x number of double bonds Therefore, if the number of carbons is the same, fatty acids with a large number of double bonds elute first, so the double bonds You can take three or more fatty acids. Furthermore, even for fatty acids containing two or more types of fatty acids having three or more double bonds, the elution amount can be estimated from the size of the ECN, so fractionation of these fatty acids is also possible.
表−２はムラサキ科植物種子油をシリカゲルで処理した
ガンマ−リノレン酸の一次濃縮物を、ＯＤＳカラムに供
したときのガンマ−リノレン酸の濃縮度合および収率を
示すものである。また表−３にはＯＤＳカラムに供する
前の脂肪酸組成を示す。表−２から明らかなように、９
８％以上のガンマ−リノレン酸を含む区分が仕込量の２
５％得られ、この区分にはガンマ−リノレン酸の５５％
が築まっている。またガンマ−リノレン酸９０％の区分
は約１０％得られ、この区分にはガンマ−リノレン酸の
２゛０％が集まり、濃縮度の低い区分に含まれるガンマ
−リノレン酸は少なく、高い濃縮度の区分を高い収率で
得られることがわかる。Table 2 shows the degree of concentration and yield of gamma-linolenic acid when a primary concentrate of gamma-linolenic acid obtained by treating the seed oil of a plant belonging to the family Violetaceae with silica gel was subjected to an ODS column. Furthermore, Table 3 shows the fatty acid composition before being subjected to the ODS column. As is clear from Table 2, 9
The category containing 8% or more gamma-linolenic acid is 2nd in the preparation amount.
This category contains 55% of gamma-linolenic acid.
is being built. In addition, about 10% of gamma-linolenic acid is obtained in the 90% category, 20% of gamma-linolenic acid is collected in this category, and less gamma-linolenic acid is contained in the less concentrated category, and the gamma-linolenic acid is found in the less concentrated category. It can be seen that the following sections can be obtained in high yield.
表−２ムラサキ科植物種子油の一次濃縮物表−３ムラサ
キ科植物種子油−次濃縮物の脂肪酸組成
実施例１
リルン酸を８．０％含む大豆油１００ｇを３％の硫酸を
含むエタノール中で加熱後、ｎ−へキサンで抽出し、大
豆脂肪酸エチル９０ｇを得る。Table 2 Primary Concentrate of Plant Seed Oils of the Purple Family Table 3 Composition of Fatty Acids of Primary Concentrates of Plant Seed Oils of the Family Purple Family Example 1 100 g of soybean oil containing 8.0% lilunic acid was dissolved in ethanol containing 3% sulfuric acid. After heating, the mixture was extracted with n-hexane to obtain 90 g of ethyl soybean fatty acid.
これをシリカゲル（粒度６０〜１００ ｍｅｓｈ、孔径
７５人）３５０ｇを充填したカラムに供し、ｎ−ヘキサ
ン／エーテル−４００／１ １０βを４時間で流したの
ちｎ−ヘキサン／エーテル＝８０／２０ １’５βを３
０分で流し溶出する区分を集める。減圧下で脱溶剤し、
−次濃縮物４０．５ｇを得る。つづいてＯＤＳ （粒度
６０〜２００ｍｅｓｈ。This was applied to a column packed with 350 g of silica gel (particle size 60-100 mesh, pore size 75), and after 4 hours of flowing n-hexane/ether 400/1 10β, n-hexane/ether = 80/20 1' 5β to 3
Collect the fraction that flows and elutes at 0 minutes. Desolvent under reduced pressure,
- 40.5 g of next concentrate are obtained. Next, ODS (particle size 60-200 mesh).
孔径７０人、カーボン率２０％）４００ｇを充填したカ
ラムに一次濃縮物の全量を供し、アセトニトリル／水−
８５／１．５を毎時１１の流速で流し、溶出量１．５〜
３．４βの区分を集めた。この区分を減圧下で脱溶剤し
て、リルン酸含０′量９７％の９ｍ縮物２．８９ｇを、
またリルン酸含有量９０％の濃縮物１．１０ｇをそれぞ
れ得た。The entire amount of the primary concentrate was applied to a column packed with 400 g (pore size 70%, carbon content 20%) of acetonitrile/water.
85/1.5 was flowed at a flow rate of 11 per hour, and the elution amount was 1.5~
The 3.4β section was collected. This fraction was desolventized under reduced pressure to obtain 2.89 g of a 9m condensate containing 97% lylunic acid.
In addition, 1.10 g of a concentrate containing 90% lylunic acid was obtained.
実施例２
海産クロレラ乾燥物から抽出したエイコサペンタエン酸
（以下ＥＰＡという）３８％を含む脂質３００ｇを常法
に従いケン化分解後、酸性下でｎ−ヘキサンで抽出して
、海産クロレラ脂肪酸１５２ｇを得る。これをシリカゲ
ル（粒度６ｏ〜１００ｍｅｓｈ、孔径１５０人）７００
ｇを充填したカラムに供しｎ−ヘキサン／エーテル−２
０’０／１ ２０１を４時間で流したのち、ｎ−へキサ
ン／エーテテル−９０／１０ ３１を３０分で流しｌ８
出する区分を集める。減圧下で脱溶剤し、ＥＰＡ含量６
９％（Ｄ −次１１Ｗ！＋７ｉ物７３ 、 ５ ｇを得
る。つづいて０ＤＳ（粒度６０〜８０ｍｅｓｈ、孔径７
ｏ人、カニボン率２０％）７００ｇを充填したカラムに
一次濃縮物の全量を供し、エタノール／水＝８５／１５
を毎時１１の流速で流し、溶出量３．０〜７．０ｇの区
分を柴める。この区分を減圧下で脱溶剤してＥＰＡ含量
９５％の無色、無臭の濃縮物３８．３ｇを得た。Example 2 300 g of a lipid containing 38% eicosapentaenoic acid (hereinafter referred to as EPA) extracted from dried marine chlorella was saponified and decomposed according to a conventional method, and then extracted with n-hexane under acidic conditions to obtain 152 g of marine chlorella fatty acids. . Silica gel (particle size 6o~100mesh, pore size 150)
n-hexane/ether-2
After flowing 0'0/1 201 for 4 hours, flowing n-hexane/ether-90/10 31 for 30 minutes, l8
Collect the categories to be issued. Desolvent under reduced pressure, EPA content 6
9% (D-order 11W!+7i material 73.5 g is obtained. Subsequently, 0DS (particle size 60-80 mesh, pore size 7
The entire amount of the primary concentrate was applied to a column packed with 700 g of ethanol/water = 85/15
Flowed at a flow rate of 11 per hour, the elution amount was divided into 3.0 to 7.0 g. This fraction was desolventized under reduced pressure to obtain 38.3 g of a colorless and odorless concentrate with an EPA content of 95%.
実施例３
糸状菌より抽出したガンマ−リノレン酸１８％を含む脂
質５０ｇを常法により３％の硫酸を含むエタノール中で
加熱したのちｎ−ヘキサンで抽出し、糸状菌脂肪酸エス
テル４８ｇを得る。これをシリカゲル（粒度１００〜２
００ｍｅｓｈ、孔径７５人）２５０ｇを充填したカラム
に供し、ｎ−ヘキサン／エーテル＝５００／１ １０ｉ
を６時間で流したのち、ｎ−ヘキサン／エーテル＝９０
／１０１１を３０分で流し、溶出する区分を集める。Example 3 50 g of a lipid containing 18% gamma-linolenic acid extracted from a filamentous fungus is heated in ethanol containing 3% sulfuric acid by a conventional method, and then extracted with n-hexane to obtain 48 g of a filamentous fungus fatty acid ester. Add this to silica gel (particle size 100-2
N-hexane/ether = 500/1 10i
After flowing for 6 hours, n-hexane/ether = 90
/1011 for 30 minutes and collect the eluting fraction.
減圧下で脱溶剤しガンマ−リノレン酸含有量３４％の一
次濃縮物２２．０ｇを得る。つづいて０ＤＳ（粒度３０
〜８０ ｍｅｓｈ、孔径７０人、カーボン率２０％＞４
００ｇを充填したカラムに一次濃縮物の全量を供し、エ
タノール／水＝９０／１０を毎時０．８１の流速で流し
、溶出量２．０〜３．Ｏｌの区分を築める。この区分を
減圧下で脱溶剤して、ガンマ−リノレン酸含量９１％の
濃縮物５．７％を得た。The solvent was removed under reduced pressure to obtain 22.0 g of a primary concentrate containing 34% gamma-linolenic acid. Next, 0DS (particle size 30
~80 mesh, pore size 70, carbon rate 20%>4
The entire amount of the primary concentrate was applied to a column packed with 0.00 g of ethanol/water = 90/10 at a flow rate of 0.81 per hour, resulting in an elution amount of 2.0 to 3.0 g. Build a division of Ol. This fraction was desolventized under reduced pressure to obtain a 5.7% concentrate with a gamma-linolenic acid content of 91%.
（６）発明の効果
本発明の方法によれば天然の動植物油脂から、リルン酸
、エイコサベンクエン酸、ガンマ−リノレン酸の如き、
分子内に二重結合を３以上有する高度不飽和脂肪酸を、
９０％以上の高濃度に、かつその区分に目的とする脂肪
酸の６０％以上を含むような高収率で濃縮することがで
きる。(6) Effects of the Invention According to the method of the present invention, natural animal and vegetable oils such as lylunic acid, eicosabencitric acid, gamma-linolenic acid, etc.
Highly unsaturated fatty acids with three or more double bonds in the molecule,
It can be concentrated to a high concentration of 90% or more and with a high yield such that the fraction contains 60% or more of the target fatty acid.
Claims (3)
填剤とするカラムに供し、次いでオクタデシル基を化学
的に結合したシリカゲルを充填剤とするカラムに供する
ことを特徴とする、分子内に二重結合を３以上有する高
度不飽和脂肪酸の濃縮法。(1) Fatty acids derived from animal and vegetable oils are first subjected to a column using silica gel as a packing material, and then subjected to a column using silica gel as a packing material to which octadecyl groups are chemically bonded. A method for concentrating highly unsaturated fatty acids having three or more bonds.
酸がガンマ−リノレン酸である特許請求の範囲第１項記
載の濃縮法。(2) The concentration method according to claim 1, wherein the highly unsaturated fatty acid having three or more double bonds in the molecule is gamma-linolenic acid.
酸がエイコサペンタエン酸である特許請求の範囲第１項
記載の濃縮法。(3) The concentration method according to claim 1, wherein the highly unsaturated fatty acid having three or more double bonds in the molecule is eicosapentaenoic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20837784A JPS6187796A (en) | 1984-10-05 | 1984-10-05 | Concentration of highly unsaturated fatty acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20837784A JPS6187796A (en) | 1984-10-05 | 1984-10-05 | Concentration of highly unsaturated fatty acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6187796A true JPS6187796A (en) | 1986-05-06 |
Family
ID=16555269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20837784A Pending JPS6187796A (en) | 1984-10-05 | 1984-10-05 | Concentration of highly unsaturated fatty acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6187796A (en) |
-
1984
- 1984-10-05 JP JP20837784A patent/JPS6187796A/en active Pending
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