JPH0358994A - Fractionation process for lipid - Google Patents
Fractionation process for lipidInfo
- Publication number
- JPH0358994A JPH0358994A JP19274689A JP19274689A JPH0358994A JP H0358994 A JPH0358994 A JP H0358994A JP 19274689 A JP19274689 A JP 19274689A JP 19274689 A JP19274689 A JP 19274689A JP H0358994 A JPH0358994 A JP H0358994A
- Authority
- JP
- Japan
- Prior art keywords
- egg yolk
- fractionation
- phospholipids
- phospholipid
- 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.)
- Pending
Links
- 150000002632 lipids Chemical class 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 13
- 238000005194 fractionation Methods 0.000 title abstract description 9
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 239000002244 precipitate Substances 0.000 claims abstract description 11
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 4
- 239000002798 polar solvent Substances 0.000 claims abstract description 4
- 239000006228 supernatant Substances 0.000 claims abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
- 210000002969 egg yolk Anatomy 0.000 abstract description 6
- 244000068988 Glycine max Species 0.000 abstract description 4
- 235000010469 Glycine max Nutrition 0.000 abstract description 4
- 238000005119 centrifugation Methods 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- JCABVIFDXFFRMT-DIPNUNPCSA-N [(2r)-1-[ethoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] octadec-9-enoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC)OC(=O)CCCCCCCC=CCCCCCCCC JCABVIFDXFFRMT-DIPNUNPCSA-N 0.000 abstract 1
- 239000008344 egg yolk phospholipid Substances 0.000 description 21
- 229940068998 egg yolk phospholipid Drugs 0.000 description 21
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 17
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000012134 supernatant fraction Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 102000002322 Egg Proteins Human genes 0.000 description 5
- 108010000912 Egg Proteins Proteins 0.000 description 5
- 235000013345 egg yolk Nutrition 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000001095 phosphatidyl group Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000258044 Solanum gilo Species 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- -1 hequinane Chemical compound 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000008349 purified phosphatidyl choline Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】 （利用分野） 本発明はリン脂質の分画方法に関する。[Detailed description of the invention] (Application field) The present invention relates to a method for fractionating phospholipids.
栄養科学、皮膚科学、化粧品科学の分野で、使用する油
を乳化するために合成または天然の乳化剤が使用されて
いる。現在天然の乳化剤だけが人に使用されたとき良好
な生物学的耐溶性を有すると考えられている。天然の乳
化剤は植物（例えば大豆またはトウモロコシ等）の脂質
画分あるいは動物の脂質画分（例えば卵黄）から常法に
よって抽出される。Synthetic or natural emulsifiers are used in the fields of nutritional science, dermatology and cosmetic science to emulsify the oils used. It is currently believed that only natural emulsifiers have good biological solubility when used in humans. Natural emulsifiers are extracted by conventional methods from the lipid fractions of plants (such as soybean or corn) or animal lipid fractions (such as egg yolk).
この方法によってリン化合物、すなわちリン脂質（例え
ばホスファチジルコリン（ＰＣ）およびホスファチジル
エタノールアミン（ＰＥ）など）、グリコリピド（糖脂
質）、ステリン及び中性脂質などが分画される。This method fractionates phosphorus compounds, ie, phospholipids (such as phosphatidylcholine (PC) and phosphatidylethanolamine (PE)), glycolipids, sterine, and neutral lipids.
本発明は上記化合物から、ホスファチジルコリンを主成
分とするリン脂質とホスファチジルエタノールアミンを
主成分とするリン脂質画分に分離することができる。さ
らに必要に応じて得られた百分を再び混合もしくは分野
して、目的とするエマルジョン（乳濁液）に応じた乳化
剤を得ることを可能ならしめる方法を提供するものであ
る。In the present invention, the above compound can be separated into a phospholipid fraction containing phosphatidylcholine as a main component and a phospholipid fraction containing phosphatidylethanolamine as a main component. Furthermore, the present invention provides a method that makes it possible to obtain an emulsifier suitable for a desired emulsion by mixing or dispersing the obtained percentages again as necessary.
（従来技術）
リン脂質は乳化剤としてリポソームあるいは脂肪乳剤の
調製に用いられる。リン脂質としては、般に大豆由来あ
るいは卵黄由来のものがよく知られる。このうち卵黄リ
ン脂質は、ホスファチジルコリン７０％以上、ホスファ
チジルエタノールアミン約２５％、スフィンゴミエリン
２〜３％、その他リン脂質１〜２％からなる。(Prior Art) Phospholipids are used as emulsifiers in the preparation of liposomes or fat emulsions. Phospholipids derived from soybeans or egg yolk are generally well known. Among these, egg yolk phospholipids consist of 70% or more of phosphatidylcholine, about 25% of phosphatidylethanolamine, 2 to 3% of sphingomyelin, and 1 to 2% of other phospholipids.
卵黄リン脂質中からホスファチノルコリン（ＰＣ）を主
成分とするリン脂質とホスファチジルエタノールアミン
（ＰＥ）を主成分とするリン脂質に分画する方法として
は吸着法（イオン交ｅ ４ＡＩ脂あるいはシリカゲルに
よる）、複塩化沈澱法（塩化亜鉛あるいは硫酸マグネシ
ウムによる）、限外ろ過去等が考えられる。（特公昭５
６−２３９９７、同５６−４７９１５、同５９−４２６
５５、同５９−５１２５２、同６０−１２ 、特開昭５
７１１５４９６、同５９−４５８３４、同５９−１５２
３９２）。The method for fractionating egg yolk phospholipids into phospholipids whose main component is phosphatinorcholine (PC) and phospholipids whose main component is phosphatidylethanolamine (PE) is adsorption (ion exchange, 4AI fat or silica gel). ), double chloride precipitation method (using zinc chloride or magnesium sulfate), ultrafiltration, etc. (Tokuko Showa 5
6-23997, 56-47915, 59-426
55, 59-51252, 60-12, Japanese Unexamined Patent Publication No. 5
7115496, 59-45834, 59-152
392).
しかし、これらの分画方法は複雑であり、また、分離し
たリン脂質中に樹脂あるいは塩化物が混入する可能性が
ある。However, these fractionation methods are complicated, and the separated phospholipids may be contaminated with resin or chloride.
（発明が解決しようとする問題点）
そこで、本発明者らは上記事情に鑑み、種々検討した結
果、卵黄リン脂質を非極性溶媒または極性の弱い溶媒ま
たはアルコール系溶媒（例えばクロロホルムまたはエタ
ノール）を用い溶解する。(Problems to be Solved by the Invention) Therefore, in view of the above circumstances, the present inventors conducted various studies and found that egg yolk phospholipids were treated with a non-polar solvent, a weakly polar solvent, or an alcoholic solvent (for example, chloroform or ethanol). Use to dissolve.
（ン容解溶媒は単一もしくは複数の混合溶媒でも用いる
ことができる。）得られた）容解’ｔ（ｌを一３０〜２
０°で放置後、±０〜＋１０’に温度を上げ生成した沈
澱画分と上清画分を回収することによりホスファチジル
エタノールアミンを主成分とする卵黄リン脂質とホスフ
ァチジルコリンを主成分とする卵黄リン脂質を分画でき
ることを見出し本発明を完成した。(A single dissolving solvent or a mixture of a plurality of solvents can be used.)
After being left at 0°, the temperature is raised to ±0 to +10' and the resulting precipitate fraction and supernatant fraction are collected to produce egg yolk phospholipids containing phosphatidylethanolamine as the main component and egg yolk phospholipid containing phosphatidylcholine as the main component. The present invention was completed by discovering that lipids can be fractionated.
（問題点を解決するための手段）
■ 出発原料
卵黄、大豆、キャンサバ、とうもろこし等純度の低いリ
ン脂質から純度の高いリン脂質まで出発原料として用い
ることができる。また、本発明で使用されるリン脂質も
一般に精製リン脂質であり、常法の有機溶媒による分画
法によって調製することができる。すなわち、たとえば
粗卵黄リン脂質を冷ｎ−ヘキサンおよび冷アセトンに溶
解後、攪拌下、徐々に冷アセトンを添加し、不溶物をろ
別回収し、再び冷ｎ−ヘキサンおよび冷アセトンに熔解
する。撹拌下、再び冷アセトンを加え、不ン容物をろ別
回収したのち、溶媒を留去し、乾燥物を得る。(Means for Solving the Problems) ■ Starting Materials From phospholipids with low purity to phospholipids with high purity, such as egg yolk, soybean, canvas, and corn, can be used as starting materials. Furthermore, the phospholipid used in the present invention is generally a purified phospholipid, and can be prepared by a conventional fractionation method using an organic solvent. That is, for example, after dissolving crude egg yolk phospholipid in cold n-hexane and cold acetone, cold acetone is gradually added while stirring, insoluble matters are collected by filtration, and the mixture is again dissolved in cold n-hexane and cold acetone. While stirring, cold acetone is added again, and after filtering and collecting the impurities, the solvent is distilled off to obtain a dry product.
このものの１例として、ホスファチジルコリンを７０〜
８０％、ホスファチジルエタノールアミンを１２〜２５
％含有し、これ以外のリン脂質として、ホスファチジル
イノシトール、ホスファチジルセリン、スフィンゴミエ
リンが含有される。（Ｄ、Ｊ。As an example of this, phosphatidylcholine is
80%, 12-25 phosphatidylethanolamine
%, and other phospholipids include phosphatidylinositol, phosphatidylserine, and sphingomyelin. (D.J.
Ｈａｎａｈａｎ ｅｔ ａｔ、 Ｊ、Ｂｉｏｌ、Ｃｈｅ
ｍ、＋１９２ ６２３−６２８（１９５１） ］。また
、本法により高純度のフォスファチジルコリン（ＰＣ）
を調製する際の原料として、また高純度のフォスファチ
ジルエタノールアミン（ＰＲ）を調製する隙の原料とし
て好適なものとして用いることができる。Hanahan et at, J. Biol, Che.
m, +192 623-628 (1951)]. In addition, this method produces highly purified phosphatidylcholine (PC).
It can be suitably used as a raw material for preparing phosphatidylethanolamine (PR) and as a raw material for preparing high-purity phosphatidylethanolamine (PR).
■ 調製法
１）？８解溶媒による溶解
卵黄リン脂質を溶解溶媒によりビ容解する。溶媒として
は非極性または極性の弱い溶媒またはアルコール系溶媒
を用いる。具体的には、クロロホルム、ヘキサン、アセ
トン、エタノール、エチルエーテル等が例示される。卵
黄リン脂質と溶解溶媒の混合比は１：２〜Ｉ：２０好ま
しくは１：５〜ｌ：ｌＯが望ましい。■ Preparation method 1)? 8. Dissolution with a dissolving solvent Egg yolk phospholipids are dissolved in a dissolving solvent. As the solvent, a nonpolar or weakly polar solvent or an alcoholic solvent is used. Specific examples include chloroform, hexane, acetone, ethanol, and ethyl ether. The mixing ratio of egg yolk phospholipid and dissolution solvent is preferably 1:2 to 1:20, preferably 1:5 to 1:1O.
２）低温下での放置
卵黄リン脂質溶解液を−３０〜−２０°でｌ〜１０時間
程度放置する（凍結状態）。2) Leaving at low temperature The egg yolk phospholipid solution is left at -30 to -20° for about 1 to 10 hours (frozen state).
３）常温に戻す
液温を±０〜１０″′にとげた後に生成した沈澱および
上清画分をデカンテーション若しくは遠心分離等により
回収する。3) Returning to room temperature The precipitate and supernatant fraction produced after the liquid temperature is brought to ±0 to 10'' are collected by decantation, centrifugation, or the like.
本分画方法は必要に応し繰返して行うことができ、繰返
しにより、目的とするリン脂質の純度を向上させること
が出来る。This fractionation method can be repeated as necessary, and by repeating it, the purity of the target phospholipid can be improved.
■ 分画物の性状
分画した卵黄リン脂質はホスファチジルエタノールアミ
ンの含量が５０％以上である。具体的には５０〜７０％
程度が例示される。またホスファチジルエタノールアミ
ン含量が５〜１５％程度の卵黄リン脂質も同時に分画さ
れる。■ Properties of the fractionated egg yolk phospholipid has a phosphatidylethanolamine content of 50% or more. Specifically, 50-70%
The degree is exemplified. Egg yolk phospholipids having a phosphatidylethanolamine content of about 5 to 15% are also fractionated at the same time.
（効 果）
本発明によれば、従来の製法に比べて、比較的簡単な方
法でホスファチジルエタノールアミン含量の高い卵黄リ
ン脂質を調製することができる。(Effects) According to the present invention, egg yolk phospholipids with a high phosphatidylethanolamine content can be prepared by a relatively simple method compared to conventional production methods.
またホスファチジルエタノールアミン含量の低い卵黄リ
ン脂質またはホスファチジルコリン含量の高い卵黄リン
脂質を調製することができる。Furthermore, egg yolk phospholipids with a low phosphatidylethanolamine content or egg yolk phospholipids with a high phosphatidylcholine content can be prepared.
（実施例）
本発明をより詳細に説明するために実施例を挙げるが本
発明はこれらによって何等限定されるものではない。(Examples) Examples will be given to explain the present invention in more detail, but the present invention is not limited by these in any way.
災庭汎上
リン脂質としての純度が約９０％の卵黄リン脂質２５ε
をクロロホルム、ヘキナン、ヘキサンとアセトン混合ン
容媒（ｌｌｘ：八ｃ＝２：１）−エタノールの各）容解
溶媒７５ｍＰ）に溶解した後、Ｎ２ガスを封入し密栓し
た。−２５°で）容液を２時間数面した。その後１０°
の恒〆品槽に浸漬し、徐々に液温を上げた。Egg yolk phospholipid 25ε with approximately 90% purity as a phospholipid
was dissolved in a dissolving solvent of chloroform, hequinane, hexane and acetone mixture (llx:8c=2:1)-ethanol (75mP), then N2 gas was filled in and the solution was sealed tightly. -25°) for several hours. then 10°
The liquid temperature was gradually raised.
液温±０〜＋５°のときに沈澱が生成した。沈澱画分と
上清画分を各々回収し、減圧乾燥を行い、乾燥品を得た
。これによって、得られた卵黄リン脂質中のホスファチ
ジルエタノールアミン含量とホスファチジルコリン含量
を表１に示す。A precipitate was formed when the liquid temperature was between ±0 and +5°. The precipitate fraction and supernatant fraction were each collected and dried under reduced pressure to obtain a dried product. Table 1 shows the phosphatidylethanolamine content and phosphatidylcholine content in the egg yolk phospholipids obtained.
−表一」−
、！ＥＪ！ｉ ！ＩＵ文
卵黄リン脂質（リン脂質純度的９０％）と混合溶媒（ヘ
キサン；アセトン−２：１）の混合比を１；２．１：３
．１；４、ｌ：９．１：１５に調製し、実施例１と同様
に実験を行った。沈澱した卵黄リン脂質の回収率、ホス
ファチジルエタノールアミンの含量、上清を回収した卵
黄リン脂質のホスファチジルエタノールアミン含量を高
速クロマトグラフィーで測定した。-Table 1"-,! EJ! i! The mixing ratio of IU egg yolk phospholipid (phospholipid purity 90%) and mixed solvent (hexane; acetone - 2:1) was 1:2.1:3.
．． 1:4, l:9.1:15, and the experiment was conducted in the same manner as in Example 1. The recovery rate of the precipitated egg yolk phospholipid, the content of phosphatidylethanolamine, and the phosphatidylethanolamine content of the egg yolk phospholipid from which the supernatant was collected were measured by high performance chromatography.
結果を表２に示す。The results are shown in Table 2.
した。この２回目の沈澱画分を、同様にエチルエーテル
にて処理して沈澱画分（３回目）を得、その上清両分を
廃棄した。一方、１回目に得られた上清画分乾燥品を上
記２回目、３回目の沈澱画分を得たと同様に処理して、
各沈澱画分を廃棄して、２回目、３回目の上清画分を得
た。高速液体クロマトグラフィーにより測定した。結果
を表３に示す。did. This second precipitated fraction was similarly treated with ethyl ether to obtain a precipitated fraction (third time), and both supernatant fractions were discarded. On the other hand, the dried supernatant fraction obtained in the first time was treated in the same manner as the precipitate fractions obtained in the second and third times.
Each precipitate fraction was discarded to obtain second and third supernatant fractions. Measured by high performance liquid chromatography. The results are shown in Table 3.
卵黄リン脂質（リン脂質純度的９６％） １００ｇをエ
チルエーテル９００ｍＮに溶解した後にＮ２ガスを封入
し密栓した。−２５°で溶解液を凍結させ４時間放置し
た。５°の恒温槽に浸漬し液温度を上げた。After dissolving 100 g of egg yolk phospholipid (phospholipid purity 96%) in 900 mN of ethyl ether, N2 gas was filled in and the solution was sealed. The lysate was frozen at -25° and left for 4 hours. The liquid temperature was raised by immersing it in a constant temperature bath at 5°.
液温Ｏ°のときに′ｄｃ澱が生成したのでその沈澱画分
と上清画分を分離し、回収した。減圧乾燥を行い乾燥品
を得た。Since a 'dc precipitate was formed when the liquid temperature was 0°, the precipitate fraction and supernatant fraction were separated and collected. Drying was performed under reduced pressure to obtain a dried product.
得られた沈澱画分乾燥品を上記卵黄リン脂質とみなして
上記と同様にエチルエーテルにて処理して沈澱画分（２
回目）を得、その上清両分を廃棄手
続
ネ甫
正
書
事件の表示
平成１年特許願第１９２７４６号
２、発明の名称
リン脂質の分画方法
３、補正をする者
羽生との関係：特１許出願人
名称 株式会社 ミドリ十字
４、代理人
〒１００
住所 東京都千代田区霞が関３丁目８番１号 虎の門三
井ビル１４階栄光特許事務所
■）明細書第１頁１６行目の［生物学的耐溶性ｊを「生
物学的耐容性」と補正する。The dried precipitated fraction obtained was treated as the egg yolk phospholipid and treated with ethyl ether in the same manner as above to obtain the precipitated fraction (2).
1999 Patent Application No. 192746 2, Title of the invention: Phospholipid fractionation method 3, Person making the amendment Relationship with Hanyu: Patent 1 applicant name: Midori Juji 4 Co., Ltd., agent: 100 Address: 14th floor, Toranomon Mitsui Building, 3-8-1 Kasumigaseki, Chiyoda-ku, Tokyo, Eikou Patent Office ■) Page 1, line 16 of the specification [Biological resistance j is corrected as "biological tolerance."
２）同書第１真下から３〜２行目の［動物の脂質画分（
例えば卵黄）」を「動物（例えば卵黄）の脂質画分」と
補正する。2) [Animal lipid fraction (
For example, egg yolk)” is corrected to “lipid fraction of an animal (e.g. egg yolk).”
３）同書第５頁６〜７行目及び８行目の「フォスファチ
ジル」を「ホスファチジル」と補正する。3) "Phosphatidyl" in lines 6-7 and 8 of page 5 of the same book is corrected to "phosphatidyl".
４）同書第８頁下から３〜２行目の「高速クロマトグラ
フィー」を「高速液体クロマトグラフィー」と補正する
。4) "High-performance chromatography" in the third to second lines from the bottom of page 8 of the same book is corrected to "high-performance liquid chromatography."
５、補正命令の日付：
（自発）
明細書の「発明の詳細な説明」の欄を次のように補正す
る。5. Date of amendment order: (Voluntary) The "Detailed Description of the Invention" column of the specification is amended as follows.
Claims (1)
ル系溶媒に溶解し、−３０〜−２０゜で放置後±０〜＋
１０゜に温度を上げ、生成した沈澱及び上清液を回収す
ることを特徴とするリン脂質の分画方法。Dissolve the lipid fraction in a non-polar or weakly polar solvent or alcoholic solvent and leave it at -30 to -20°, then ±0 to +
A method for fractionating phospholipids, which comprises raising the temperature to 10° and collecting the generated precipitate and supernatant.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19274689A JPH0358994A (en) | 1989-07-27 | 1989-07-27 | Fractionation process for lipid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19274689A JPH0358994A (en) | 1989-07-27 | 1989-07-27 | Fractionation process for lipid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0358994A true JPH0358994A (en) | 1991-03-14 |
Family
ID=16296366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19274689A Pending JPH0358994A (en) | 1989-07-27 | 1989-07-27 | Fractionation process for lipid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0358994A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005072477A3 (en) * | 2004-01-26 | 2005-09-29 | Martek Biosciences Corp | Method for the separation of phospholipids from phospholipid-containing materials |
-
1989
- 1989-07-27 JP JP19274689A patent/JPH0358994A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005072477A3 (en) * | 2004-01-26 | 2005-09-29 | Martek Biosciences Corp | Method for the separation of phospholipids from phospholipid-containing materials |
| EP1718584A2 (en) * | 2004-01-26 | 2006-11-08 | Martek Biosciences Corporation | Method for the separation of phospholipids from phospholipid-containing materials |
| US7566570B2 (en) | 2004-01-26 | 2009-07-28 | Martek Biosciences Corporation | Method for the separation of phospholipids from phospholipid-containing materials |
| EP1718584A4 (en) * | 2004-01-26 | 2009-10-21 | Martek Biosciences Corp | Method for the separation of phospholipids from phospholipid-containing materials |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3782457B2 (en) | Fractionated vegetable oil | |
| DE69701086T2 (en) | PROTEIN EXTRACTION FROM OILY SEEDS | |
| DE69109169T2 (en) | Functional cholesterol-free egg yolk. | |
| CN1422122A (en) | Method for the fractionation of oil and polar lipid-containing native raw material | |
| US4465693A (en) | Intravenously administered emulsion from a lecithin base and method of preparation | |
| DE69426114T2 (en) | METHOD FOR PRODUCING HIGH PURITY PHOSPHATIDYLCHOLINS | |
| JP2987682B2 (en) | Concentration of acidic phospholipids | |
| IE51981B1 (en) | Process for the separation of oil and/or phosphatidylethanolamine from alcohol soluble phosphatidylcholine products containing the same | |
| US4563354A (en) | Oil-in-water emulsion for parenteral administration | |
| DE69420712T2 (en) | METHOD FOR THE EXTRACTION OF SPHINGOMYELINE | |
| JPH0358994A (en) | Fractionation process for lipid | |
| JPS59152392A (en) | Fractionation of phosphatide | |
| JP2503567B2 (en) | Lecithin purification method | |
| JPS5929694A (en) | Method of obtaining ethanol phosphatide fraction | |
| RU2134985C1 (en) | Phospholipid food product "vitol-choline" and method of its preparing | |
| JPS6016B2 (en) | Process for producing crude product with high content of phosphatidylcholine | |
| JPH10265485A (en) | Fractionation and production of high-concentration phospholipid from lecithin | |
| JPS6354926A (en) | Surfactant composition | |
| JP2515839B2 (en) | Phospholipid purification method | |
| DE2335334B2 (en) | PROCESS FOR THE RECOVERY OF HIGHLY PURIFIED PHOSPHATIDES FROM ANIMAL ORGANS | |
| JPH0662648B2 (en) | Method for producing high-purity lecithin | |
| JPH0586796B2 (en) | ||
| JP3650168B2 (en) | Lysated phospholipid composition and process for producing the same | |
| JPH10348A (en) | Emulsion | |
| Kishk et al. | IMPROVEMENT OF EMULSION PROPERTIES OF LECITHINS EXTRACTED FROM DIFFERENT OIL SOURCES BY COMPLEX-FORMATION WITH PROTIENS |