JPH04135456A - Collection of lysolecithin containing highly concentrated lysophosphatidylchloline - Google Patents
Collection of lysolecithin containing highly concentrated lysophosphatidylchlolineInfo
- Publication number
- JPH04135456A JPH04135456A JP2258165A JP25816590A JPH04135456A JP H04135456 A JPH04135456 A JP H04135456A JP 2258165 A JP2258165 A JP 2258165A JP 25816590 A JP25816590 A JP 25816590A JP H04135456 A JPH04135456 A JP H04135456A
- Authority
- JP
- Japan
- Prior art keywords
- lysolecithin
- extraction
- lecithin
- carbon dioxide
- 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.)
- Granted
Links
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 238000000605 extraction Methods 0.000 claims abstract description 67
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000002904 solvent Substances 0.000 claims abstract description 39
- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 claims abstract description 24
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 24
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 23
- 239000000787 lecithin Substances 0.000 claims abstract description 23
- 235000010445 lecithin Nutrition 0.000 claims abstract description 23
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims abstract description 21
- 229940067606 lecithin Drugs 0.000 claims abstract description 21
- 239000012046 mixed solvent Substances 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 102000004190 Enzymes Human genes 0.000 claims abstract description 8
- 108090000790 Enzymes Proteins 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 6
- 239000003921 oil Substances 0.000 abstract description 10
- 239000003925 fat Substances 0.000 abstract description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 102100037611 Lysophospholipase Human genes 0.000 abstract description 4
- 241001465754 Metazoa Species 0.000 abstract description 4
- 108010058864 Phospholipases A2 Proteins 0.000 abstract description 4
- 235000013311 vegetables Nutrition 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 description 31
- 239000000203 mixture Substances 0.000 description 21
- 239000000843 powder Substances 0.000 description 20
- 102000002322 Egg Proteins Human genes 0.000 description 10
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 10
- 108010000912 Egg Proteins Proteins 0.000 description 9
- 210000002969 egg yolk Anatomy 0.000 description 9
- 235000013345 egg yolk Nutrition 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 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 8
- 230000000694 effects Effects 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 150000003904 phospholipids Chemical class 0.000 description 6
- 229920001353 Dextrin Polymers 0.000 description 5
- 239000004375 Dextrin Substances 0.000 description 5
- CWRILEGKIAOYKP-SSDOTTSWSA-M [(2r)-3-acetyloxy-2-hydroxypropyl] 2-aminoethyl phosphate Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCCN CWRILEGKIAOYKP-SSDOTTSWSA-M 0.000 description 5
- 235000019425 dextrin Nutrition 0.000 description 5
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 5
- 238000006911 enzymatic reaction Methods 0.000 description 4
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910002090 carbon oxide Inorganic materials 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000010451 perlite Substances 0.000 description 3
- 235000019362 perlite Nutrition 0.000 description 3
- 229940083466 soybean lecithin Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000003811 acetone extraction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- -1 soybean lecithin Chemical compound 0.000 description 1
- 235000019710 soybean protein Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003815 supercritical carbon dioxide extraction Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
Description
【発明の詳細な説明】
（技術分野）
本発明は、原料となるリゾレシチンより、必要な成分を
採取する方法に係り、特に、種々の成分の中で、リゾホ
スファチジルコリン（ＬＰＧ）を高濃度に含むリゾレシ
チンを採取する方法に関するものである。Detailed Description of the Invention (Technical Field) The present invention relates to a method for collecting necessary components from lysolecithin as a raw material, and in particular, lysolecithin containing a high concentration of lysophosphatidylcholine (LPG) among various components. The present invention relates to a method for collecting lysolecithin.
（背景技術）
リゾレシチン（リゾリン脂質）は、分子中に水酸基を持
つために、レシチン（リン脂質）よりも親水性が大きく
、ｐＨや温度変化に対して安定なエマルジョンを形成す
る特徴を有するが、中でも、リゾホスファチジルコリン
（Ｌ Ｐ Ｃ）は、非イオン界面活性剤に似た挙動を示
し、塩類濃度の高い溶液に対しても界面活性を保つと言
われている。(Background Art) Because lysolecithin (lysophospholipid) has a hydroxyl group in its molecule, it has greater hydrophilicity than lecithin (phospholipid), and has the characteristic of forming an emulsion that is stable against changes in pH and temperature. Among them, lysophosphatidylcholine (LPC) is said to exhibit behavior similar to nonionic surfactants and maintains surface activity even in solutions with high salt concentrations.
このため、ＬＰＣは、食品、化粧品、医薬品等の各分野
において、広く応用が期待されているものである。Therefore, LPC is expected to be widely applied in various fields such as foods, cosmetics, and pharmaceuticals.
ところで、市販されているリゾレシチンは、卵黄レシチ
ンや大豆レシチン等の動植物性レシチンに、酵素を作用
させて、該レシチンを加水分解することにより、製造さ
れているが、原料によって多少組成は異なるものの、一
般に、前記リゾホスファチジルコリン（ＬＰＣ）の他に
、リゾホスファチジルエタノールアミン（ＬＰＥ）やり
ゾホスファチジン酸（ＬＰＡ）、更にはリゾ化されてい
ない未反応の各種リン脂質を含んでおり、また多くの場
合、原料レシチンに由来する中性油脂を含んでいるので
、ＬＰＣ濃度はそれほど高くはないのである。By the way, commercially available lysolecithin is produced by hydrolyzing animal and vegetable lecithin such as egg yolk lecithin and soybean lecithin with enzymes, but although the composition differs depending on the raw material, Generally, in addition to the lysophosphatidylcholine (LPC), it contains lysophosphatidylethanolamine (LPE), sophosphatidic acid (LPA), and various unreacted phospholipids that have not been lysized, and in many cases, Since it contains neutral fats and oils derived from the raw material lecithin, the LPC concentration is not very high.
而して、より高濃度のＬＰＧを含むリゾレシチンを製造
するためには、アセトン等の溶剤を用いて中性油脂を除
去し、更にアルコール分画を行なう方法が知られている
。しかし、この方法は、操作が面倒である上に、大豆レ
シチン等の植物性レシチンから得られたリゾレシチンを
原料とする場合等には、原料にＬＰＧ以外のアルコール
可溶性成分が多足に含まれることから、アルコール分画
操作を繰り返して行なっても、Ｌ Ｐ Ｇ濃度を７０％
以上にすることは非常に困難である問題を内在している
。In order to produce lysolecithin containing a higher concentration of LPG, a method is known in which neutral fats and oils are removed using a solvent such as acetone, and further alcohol fractionation is performed. However, this method is cumbersome to operate, and when the raw material is lysolecithin obtained from vegetable lecithin such as soybean lecithin, the raw material may contain many alcohol-soluble components other than LPG. Even if the alcohol fractionation operation is repeated, the LPG concentration remains at 70%.
Doing so has inherent problems that make it extremely difficult.
また、シリカゲル等を用いるクロマト法は、高濃度ＬＰ
Ｇを分画することは可能であるが、生産性が悪く、高価
であって、工業的手法ではないのである。In addition, the chromatography method using silica gel etc. uses high concentration LP.
Although it is possible to fractionate G, it is low in productivity and expensive, and is not an industrial method.
（解決課題）
このような事情を背景として、本発明は為されたもので
あって、その解決課題とするところは、簡便な操作によ
って、原料リゾレシチン（リゾリン脂質混合物）の中か
ら、リゾホスファチジルコリン（Ｌ Ｐ Ｇ ）を効率
的に取り出して、高濃度のＬ Ｐ Ｇを含むリゾレシチ
ンを有利に採取することにある。(Problem to be solved) Against this background, the present invention has been made, and the problem to be solved is to extract lysophosphatidylcholine ( The object of the present invention is to efficiently extract LPG) and advantageously collect lysolecithin containing a high concentration of LPG.
（解決手段）
上記課題を解決するために、本発明者らが鋭意研究を重
ねた結果、所定の二酸化炭素とアルコールの混合溶媒に
て、脱脂されたリゾレシチンの抽出操作を行なうと、各
種のりプリン脂質及びリゾ化されずに残った各種の未反
応のリン脂質の中にあって、リゾホスファチジルコリン
（ＬＰＧ）が抽出され易く、未反応のリン脂質は抽出さ
れ難いことを見い出し、そしてこの知見に基づいて、本
発明を完成したのである。(Solution Means) In order to solve the above-mentioned problems, the present inventors have conducted extensive research and found that when defatted lysolecithin is extracted with a predetermined mixed solvent of carbon dioxide and alcohol, various glue puddings can be extracted. We discovered that lysophosphatidylcholine (LPG) is easily extracted among lipids and various unreacted phospholipids that remain without being resolized, and that unreacted phospholipids are difficult to extract, and based on this knowledge, Thus, the present invention was completed.
すなわち、本発明は、レシチンに酵素を作用させて得ら
れるリゾレシチンを脱脂した後、液体状態若しくは超臨
界状態の二酸化炭素と炭素数が１〜４のアルコールとか
らなる混合溶媒を抽出溶媒として用い、該混合溶媒にて
、前記脱脂されたリゾレシチンの抽出操作を行なって、
その抽出液から前記混合溶媒を除去することによって、
高濃度のリゾホスファチジルコリンを含むリゾレシチン
を採取することを、その要旨とするものである。That is, in the present invention, after defatting lysolecithin obtained by allowing an enzyme to act on lecithin, a mixed solvent consisting of carbon dioxide in a liquid state or a supercritical state and an alcohol having 1 to 4 carbon atoms is used as an extraction solvent, Performing an extraction operation of the defatted lysolecithin in the mixed solvent,
By removing the mixed solvent from the extract,
The gist of this method is to collect lysolecithin containing a high concentration of lysophosphatidylcholine.
（具体的構成）
ところで、本発明において、抽出操作が施されるべきリ
ゾレシチンは、動物または植物由来のレシチンが酵素に
より加水分解されたものであって、例えば、卵黄、牛脳
、腫脹等から得られる動物由来のレシチンや、大豆、と
うもろこし、なたね等の植物種子から得られる植物由来
のレシチンに、所定の酵素を作用させることにより得ら
れる。なお、通常、酵素として、ホスホリパーゼＡ２が
使用されるが、これには、市販の製剤を使用することが
出来る。また、レシチンや、リゾレシチンも各種類のも
のが製品化され、市販されているので、それらを使用す
ることが可能である。(Specific Structure) In the present invention, the lysolecithin to be extracted is obtained by enzymatically hydrolyzing lecithin derived from animals or plants, and may be obtained from, for example, egg yolk, bovine brain, swelling, etc. It can be obtained by reacting a predetermined enzyme with animal-derived lecithin obtained from plants such as soybeans, corn, rapeseed, and other plant-derived lecithins. Note that phospholipase A2 is usually used as the enzyme, but commercially available preparations can be used for this. Furthermore, various types of lecithin and lysolecithin have been commercialized and are commercially available, so it is possible to use them.
そして、かかる酵素処理によって得られた原料リゾレシ
チンが、中性油脂を含む場合には、Ｉ−ＰＣの抽出操作
に先立って、予め油脂分が除去せしめられるのである。If the raw material lysolecithin obtained by such enzyme treatment contains neutral fats and oils, the fats and oils are removed in advance prior to the I-PC extraction operation.
油脂分の除去方法としては、従来から行なわれている公
知の各種手法を用いることが出来、例えば、アセトン抽
出や超臨界二酸化炭素抽出によって、油脂分を抽出分離
することが出来る。As a method for removing fats and oils, various conventionally known methods can be used. For example, fats and oils can be extracted and separated by acetone extraction or supercritical carbon dioxide extraction.
また、特に、原料リゾレシチンが植物性レシチンに由来
するものである場合には、ＬＰＣの抽出操作において、
原料リゾレシチンと抽出溶媒との接触を容易にするため
に、該リゾレシチンを抽出溶媒に不溶の粉粒体と予め混
合しておくことが望ましい。何故なら、一般に、固体ま
たは液体であるリゾレシチン相に対して、抽出溶媒の浸
透は著しく悪く、リゾレシチン相の抽出溶媒に対する溶
解速度も遅いところから、単にリゾレシチンに抽出溶媒
を注入しただけでは、抽出に時間がかかり、必要以上に
抽出溶媒を使用するようになるばかりでなく、抽出溶媒
の浸透の違いにより、再現性の悪い不安定な抽出になる
恐れがあるからである。In addition, especially when the raw material lysolecithin is derived from vegetable lecithin, in the LPC extraction operation,
In order to facilitate the contact between the raw material lysolecithin and the extraction solvent, it is desirable to mix the lysolecithin in advance with powder that is insoluble in the extraction solvent. This is because, in general, the penetration of extraction solvent into the solid or liquid lysolecithin phase is extremely poor, and the rate of dissolution of the lysolecithin phase in the extraction solvent is slow. This is because not only does it take time and use more extraction solvent than necessary, but also there is a risk of unstable extraction with poor reproducibility due to differences in the penetration of the extraction solvent.
それ故、原料リゾレシチンを、抽出操作に先立つて、予
め粉粒体と混合しておけば、抽出溶媒に対する該リゾレ
シチンの接触面積を大幅に増やして、抽出を容易にする
ことが出来るのであり、更に抽出溶媒の流路を均等にし
て、溶液の流れを一様にすることが出来るのである。Therefore, if the raw material lysolecithin is mixed with powder before the extraction operation, the contact area of the lysolecithin with the extraction solvent can be greatly increased, making extraction easier. By making the flow path of the extraction solvent uniform, it is possible to make the flow of the solution uniform.
因みに、かかる粉粒体の具体例としては、後述する二酸
化炭素とアルコールとからなる抽出溶媒に不溶で且つ原
料リゾレシチンに対して不活性なもの（即ち、原料リゾ
レシチンと反応したり、強固な吸着作用を示さないもの
）であれば、特に制限はなく、でんぷん粉末、大豆蛋白
、卵白、セルロース系粉末、多孔性シリカ等が用いられ
得る。Incidentally, specific examples of such powders include those that are insoluble in the extraction solvent consisting of carbon dioxide and alcohol, which will be described later, and are inert to the raw material lysolecithin (i.e., those that do not react with the raw material lysolecithin or have a strong adsorption effect). There are no particular limitations, and starch powder, soybean protein, egg white, cellulose powder, porous silica, and the like can be used.
また、抽出溶媒に配合されるアルコールが、２％以上の
水を含まなければ、デキストリン粉末も使うことが出来
る。Dextrin powder can also be used as long as the alcohol blended into the extraction solvent does not contain more than 2% water.
また、粉粒体と原料リゾレシチンとの混合比については
、均一な混合が為され得る割合に適宜に決定されればよ
いが、必要以上に粉粒体を用いることば経済的でないの
で、原料リゾレシチンの１重量部に対して、粉粒体を０
．２〜４重量部の範囲で混合するのが適当である。In addition, the mixing ratio of the powder and the raw material lysolecithin may be determined as appropriate to ensure uniform mixing, but since it is uneconomical to use more powder than necessary, the raw material lysolecithin 0 part by weight of powder or granules
．． It is appropriate to mix in a range of 2 to 4 parts by weight.
さらに、原料リゾレシチンが粉末状または液状の場合は
、粉粒体と均一に混合せしめることは容易であるが、固
体または著しく高粘度の液体の場合には、原料リゾレシ
チンを適当な溶剤に溶かしてから、粉粒体と混合して、
その後乾燥するとよい。その際、原料リゾレシチンの溶
解に使用する溶剤を、後述する抽出溶媒の一成分とされ
るアルコールとする場合には、混合後の乾燥は省略する
ことが出来る。Furthermore, if the raw material lysolecithin is in the form of powder or liquid, it is easy to mix it uniformly with powder or granules, but if it is solid or a liquid with extremely high viscosity, the raw material lysolecithin must be dissolved in an appropriate solvent and then mixed. , mixed with powder and granular material,
It is best to dry it afterwards. At this time, when the solvent used to dissolve the raw material lysolecithin is alcohol, which is a component of the extraction solvent described later, drying after mixing can be omitted.
なお、卵黄由来のリゾレシチンにおいては、卵黄中の蛋
白質が上記の粉粒体の役目を果たすので、特別に粉粒体
を添加する必要はない。要するに、原料の性状にあわせ
、抽出が均等に為されるように、粉粒体の添加を考慮す
ればよいのである。In addition, in the case of lysolecithin derived from egg yolk, since the protein in the egg yolk plays the role of the above-mentioned granular material, there is no need to specifically add granular material. In short, it is only necessary to consider the addition of powder or granules to ensure uniform extraction according to the properties of the raw material.
このようにして調製された原料リゾレシチンの組成は、
リゾホスファチジルコリン（ＬＰＧ）以外に、リゾホス
ファチジルエタノールアミン（ＬＰＥ）やりゾホスファ
チジン酸（ＬＰＡ）、更には、リゾ化されずに残った未
反応のホスファチジルコリン（ＰＣ）、ホスファチジル
エタノールアミン（ＰＥ）、ホスファチジルイノシトー
ル（ＰＩ）等を含むものである。そして、本発明におい
ては、このような原料リゾレシチンに対して、以下の如
き抽出溶媒を用いて抽出操作を行なうことにより、ＬＰ
Ｃを効率的に抽出せしめ、その濃度を著しく高めるので
ある。The composition of the raw material lysolecithin prepared in this way is:
In addition to lysophosphatidylcholine (LPG), there are also lysophosphatidylethanolamine (LPE), sophosphatidic acid (LPA), and unreacted phosphatidylcholine (PC), phosphatidylethanolamine (PE), and phosphatidylinositol that remain unreacted. (PI) etc. In the present invention, the raw material lysolecithin is subjected to an extraction operation using the following extraction solvent to obtain LP.
This allows for efficient extraction of C and significantly increases its concentration.
すなわち、本発明では、液体状態若しくは超臨界状態の
二酸化炭素と炭素数が１〜４のアルコールの混合溶媒を
、抽出溶媒として使用する。そのうちの二酸化炭素は、
抽出溶媒としてよく知られているものであるが、本発明
においては、アルコールに可溶のリゾレシチンおよび未
反応のレシチンの抽出比率をコントロールする作用も有
するのである。なお、二酸化炭素の超臨界状態は、温度
が臨界温度： ３１．１°Ｃ以上、圧力が臨界圧力＝７
゜３８ＭＰａ （７５，２ｋｇ／ｃＪ）以」−の状態で
あって、また液体状態は、臨界温度よりも低い温度下の
状態をいう。That is, in the present invention, a mixed solvent of carbon dioxide in a liquid state or a supercritical state and an alcohol having 1 to 4 carbon atoms is used as an extraction solvent. Among them, carbon dioxide is
Although it is well known as an extraction solvent, in the present invention it also has the effect of controlling the extraction ratio of alcohol-soluble lysolecithin and unreacted lecithin. In addition, in the supercritical state of carbon dioxide, the temperature is critical temperature: 31.1°C or more, and the pressure is critical pressure = 7
38 MPa (75.2 kg/cJ) or less, and the liquid state refers to a state at a temperature lower than the critical temperature.
一方、アルコールはＬＰＧ、ＬＰＥ、ＰＣ，ＰＥ等の溶
剤として働くものであって、炭素数が１〜４のものが何
れも使用され得、その中から１種類若しくは２種類以上
が適宜に組み合わされて選択されることとなる。なお、
炭素数が４より大きいと、リゾレシチンの溶解度が低く
なり、事実上、抽出溶剤として作用し得なくなるのであ
る。また、アルコールの水分含有量は１０重量％程度以
下であることが望ましい。それを越える割合で水分が含
まれる場合には、リゾレシチンの溶解度を低下させるだ
けでなく、ＬＰＣの分別能力を低下させる等、高濃度の
ＬＰＧ抽出に悪影響を及ぼす恐れがあるからである。On the other hand, alcohol acts as a solvent for LPG, LPE, PC, PE, etc., and any alcohol having 1 to 4 carbon atoms can be used, and one or more of them can be appropriately combined. It will be selected based on the following. In addition,
If the number of carbon atoms is greater than 4, the solubility of lysolecithin will be low and it will virtually no longer be able to act as an extraction solvent. Further, it is desirable that the water content of the alcohol is about 10% by weight or less. This is because if water is contained in a proportion exceeding this, it may not only reduce the solubility of lysolecithin but also reduce the fractionation ability of LPC, which may have an adverse effect on the extraction of high-concentration LPG.
そして、かかるアルコールと前記二酸化炭素の混合割合
は、前記原料リゾレシチンの組成等に応じて適宜に決定
されるところであるが、好ましくは、アルコールの配合
量が、４〜２０重量％程度である。アルコールの配合量
が、この範囲より少ない場合には、ＬＰＧの溶解度が小
さくなって収率が落ちる傾向があり２反対に混合割合が
これより大きいと、リゾレシチンの溶解性をコントロー
ルする二酸化炭素の作用が低下して、ＬＰＧ濃度が上が
り難くなる懸念があるからである。The mixing ratio of the alcohol and the carbon dioxide is appropriately determined depending on the composition of the raw material lysolecithin, but preferably, the blending amount of the alcohol is about 4 to 20% by weight. If the amount of alcohol blended is less than this range, the solubility of LPG will decrease and the yield will tend to drop.2 Conversely, if the mixing ratio is greater than this, the effect of carbon dioxide, which controls the solubility of lysolecithin, will decrease. This is because there is a concern that the LPG concentration will decrease and it will be difficult to increase the LPG concentration.
ところで、第１図は、本発明手法が適用される抽出装置
の一例を示すフローシートであるが、そこに示されるよ
うに、ホンへ２より二酸化炭素が供給される一方、タン
ク４よりエントレーナたる所定のアルコールが供給され
、それらが流路上で所定の割合に混合されることによっ
て、抽出溶媒が調製されるようになっている。そして、
該抽出溶媒は、原料リゾレシチンが収容され、且つ所定
温度及び所定圧力に制御されている抽出器６内に供給さ
れ、以てＬＰＧの抽出が行なわれるのである。By the way, FIG. 1 is a flow sheet showing an example of an extraction apparatus to which the method of the present invention is applied. The extraction solvent is prepared by supplying predetermined alcohols and mixing them in a predetermined ratio on the flow path. and,
The extraction solvent is supplied into the extractor 6, which contains the raw material lysolecithin and is controlled at a predetermined temperature and pressure, and extracts LPG.
しかる後、原料リゾレシチン中の可溶成分を溶かし込ん
だ抽出液が、抽出器６外へ取り出され、分離器８，１０
において、先ず、常圧に戻されて、−酸化炭素とアルコ
ール溶液とに分離される。次いで、常法により、減圧蒸
溜にてアルコールが除去されることにより、目的とする
高濃度のｒ、 ｐ ｃを含むリゾレシチンを得るのであ
る。なお、３５はポンプであり、１２はフローメーター
、１４は積算式ガスメーターである。After that, the extract containing the soluble components in the raw material lysolecithin is taken out of the extractor 6 and passed through the separators 8 and 10.
In the process, the pressure is first returned to normal pressure and separated into -carbon oxide and alcohol solution. Next, the alcohol is removed by vacuum distillation using a conventional method to obtain lysolecithin containing the desired high concentrations of r and pc. Note that 35 is a pump, 12 is a flow meter, and 14 is an integrating gas meter.
より詳細には、上記の抽出操作に際しては、般に、温度
が低い程、または圧力が高い程、抽出溶媒に対する原料
リゾレシチンの溶解度は大きくなる。一方、未反応のホ
スファチジルコリン（ＰＣ）が原料リゾレシチン中に残
存している場合には、ＬＰＧと共に、ＰＣが抽出されて
くるので、その場合には、若干、抽出温度を高めに設定
するほうがよい。なお、より具体的な温度条件及び圧力
条件は、目的とするＬＰＣ濃度や収率、また原料リグレ
シチンの組成等に応じて、適宜に最適な条件が選ばれる
こととなるが、一般に、温度が７０°Ｃ以上ではリゾレ
シチンの熱変質が著しくなる問題があり、また過度な低
温抽出は経済的でなく、更にまた、圧力が４５ＭＰａを
越える場合には、装置設計及び維持管理上問題があると
ころから、酸化炭素として、超臨界状態のものを使用す
る場合には、温度＝３１〜６５°Ｃ１圧カニ８〜４５Ｍ
Ｐａの範囲が好ましく、より好ましくは、温度器
＝４０〜６０°Ｃ１圧カニ１０〜３０ＭＰａである。More specifically, in the above extraction operation, generally speaking, the lower the temperature or the higher the pressure, the greater the solubility of the raw material lysolecithin in the extraction solvent. On the other hand, if unreacted phosphatidylcholine (PC) remains in the raw material lysolecithin, PC will be extracted together with LPG, so in that case, it is better to set the extraction temperature slightly higher. The more specific temperature and pressure conditions will be appropriately selected depending on the target LPC concentration and yield, the composition of the raw material reglecitin, etc., but in general, the temperature is 70°C. If the temperature exceeds 45 MPa, there is a problem in that lysolecithin undergoes significant thermal deterioration, excessively low temperature extraction is not economical, and if the pressure exceeds 45 MPa, there are problems in equipment design and maintenance. When using carbon oxide in a supercritical state, temperature = 31-65°C, pressure 8-45M
The range of Pa is preferable, and more preferably, the temperature is 40 to 60° C. and the pressure is 10 to 30 MPa.
また、液体状態の二酸化炭素を使用する場合には、温度
ニー２０〜３０°Ｃ１圧カニ５〜８ＭＰａの範囲が好ま
しい。Further, when carbon dioxide in a liquid state is used, a temperature range of 20 to 30° C. and a pressure of 5 to 8 MPa is preferable.
このようにして、前記脱脂された原料リゾレシチンに、
二酸化炭素とアルコールとからなる抽出溶媒を適用した
場合には、各種リゾレシチン及び未反応のレシチンの中
において、ＬＰＣが最も効率的に抽出され、反対に未反
応のレシチンは抽出され難く、中でもＰＩは殆ど抽出さ
れないのである。従って、かかる抽出操作を経ることに
よって、ＰＩの殆どは残留成分として残り、また、抽出
液中にＬＰＧ以外のリゾレシチンや未反応のレシチンが
多量に混入することも効果的に抑制されることから、抽
出されるリゾレシチンのＬＰＣ濃度を著しく高めること
が出来るのである。In this way, the defatted raw material lysolecithin,
When an extraction solvent consisting of carbon dioxide and alcohol is applied, LPC is extracted most efficiently among various lysolecithins and unreacted lecithin, while unreacted lecithin is difficult to extract, especially PI. Very little is extracted. Therefore, by going through this extraction operation, most of the PI remains as a residual component, and it is also effectively suppressed that large amounts of lysolecithin other than LPG and unreacted lecithin are mixed into the extract. This makes it possible to significantly increase the LPC concentration of extracted lysolecithin.
なお、具体的な抽出時間の設定は、抽出装置の規模、二
酸化炭素とアルコールの混合溶媒の送り量、その他の抽
出条件や原料リゾレシチンの組成等に応じて、適宜に行
なわれるところであるが、抽出時間があまり長くなると
、次第にＬＰＧ以外のアルコール可溶成分が混入してく
ることとなるため、一般に、抽出開始後の相対的に早い
時期の抽出区分を採取することが望ましい。The specific extraction time is determined as appropriate depending on the scale of the extraction device, the amount of mixed solvent of carbon dioxide and alcohol fed, other extraction conditions, and the composition of the raw material lysolecithin. If the time is too long, alcohol-soluble components other than LPG will gradually become mixed in, so it is generally desirable to collect the extraction fraction at a relatively early stage after the start of extraction.
（実施例）
以下に、本発明の幾つかの実施例を示し、本発明を更に
具体的に明らかにすることとするが、本発明が、そのよ
うな実施例の記載によって、何等の制約をも受けるもの
でないことば、言うまでもないところである。(Examples) Below, some examples of the present invention will be shown to clarify the present invention more specifically, but the present invention is not limited in any way by the description of such examples. Needless to say, this is not a word that should be accepted.
また、本発明には、以下の実施例の他にも、更には上記
の具体的記述以外にも、本発明の趣旨を逸脱しない限り
において、当業者の知識に基づいて種々なる変更、修正
、改良等を加え得るものであることが、理解されるべき
である。In addition to the following examples and the above-mentioned specific description, the present invention includes various changes, modifications, and changes based on the knowledge of those skilled in the art, as long as they do not depart from the spirit of the present invention. It should be understood that improvements and the like may be made.
実施例 １
市販のリゾレシチン（協和発酵工業製、エルマイザーＡ
）から、常法に従いアセトンを用いて油脂骨を除去し、
減圧下で溶剤を除去して、粉末状の脱脂リゾレシチンを
得た。そして、この脱脂すゾレシチン：３０ｇを、約６
０ｍ２のヘキサンに）容解し、デキストリン粉末（松谷
化学製、パインフロー）：６０ｇと混合した後、４０°
Ｃ１真空下で溶剤を除去して、リゾレシチンとデキスト
リンとの粉末混合物を調製した。Example 1 Commercially available lysolecithin (manufactured by Kyowa Hakko Kogyo, Elmizer A)
), remove the greasy bones using acetone according to the usual method,
The solvent was removed under reduced pressure to obtain powdered defatted lysolecithin. Then, add 30g of this defatted zolecithin to about 6
0 m2 of hexane), mixed with 60 g of dextrin powder (Matsutani Chemical, Pine Flow), and then heated at 40°
A powder mixture of lysolecithin and dextrin was prepared by removing the solvent under C1 vacuum.
次いで、この粉末混合物を５００ ｍｌの抽出容器に入
れ、超臨界二酸化炭素とエタノール（２重量％の水分を
含む）との混合溶媒（エタノール比率：・１６重間％）
を連続的に注入して、Ｌ Ｐ Ｇの抽出を８時間行なっ
た。抽出条件は、温度＝４０°Ｃ１圧カニ３０ＭＰａ、
溶媒の平均流量：２００１’ｌ！／ｈであった。かかる
抽出により得られたりヅレシチンの量は、２．７ｇであ
り、収率は９．０％であった。Next, this powder mixture was placed in a 500 ml extraction container, and a mixed solvent of supercritical carbon dioxide and ethanol (containing 2% water by weight) (ethanol ratio: 16% by weight) was added.
was continuously injected for 8 hours to extract LPG. The extraction conditions were: temperature = 40°C, 1 pressure crab, 30MPa;
Average flow rate of solvent: 2001'l! /h. The amount of durecithin obtained by this extraction was 2.7 g, and the yield was 9.0%.
そして、このようにして採取されたリゾレシチンの組成
を、「基準油脂分析法」 （日本油化学協会編、２．２
．８．４ａ−８６）の［リン脂質リン組成ｊに準拠した
薄層クロマトグラフ法によって分析し、主なリン脂質に
ついて、その結果を下記第１表に示した。また、抽出原
料とした脱脂リゾレシチン（コントロール）の組成も分
析し、同表に合わせて示した。The composition of the lysolecithin collected in this way was determined using the "Standard Oil and Fat Analysis Method" (edited by Japan Oil Chemists' Association, 2.2).
．． 8.4a-86) [Phospholipid Phosphorus Composition j] The results for the main phospholipids are shown in Table 1 below. The composition of defatted lysolecithin (control), which was used as an extraction raw material, was also analyzed and shown in the same table.
その結果より明らかなように、ＬＰＧ濃度は、３０．１
％（抽出前）から６４．８％（抽出後）にまで高められ
た。また、未反応のＰＥ、Ｐｒは、抽出されなかった。As is clear from the results, the LPG concentration was 30.1
% (before extraction) to 64.8% (after extraction). Moreover, unreacted PE and Pr were not extracted.
実施例 ２
ホスファチジルコリン含有■を強化した大豆レシチン（
ツルーレシチン工業製、ＰＣ３５）：１００重量部に対
して、水：５０重量部を加え、撹拌して均一な混合液と
した。そして、この混合液に、０，１％のホスホリパー
ゼＡ２製剤（ＮＯＶＯ社製、レシターゼ１０ Ｌ ）を
加え、ＩＮ水酸化ナトリウム溶液で、ｐ Ｈを５．５〜
６．５に調整しながら、５０〜６０°Ｃで４８時間、酵
素反応を行なった。そして、得られた酵素反応物を５０
〜６０’Ｃで真空乾燥して水分を除去した後、アセトン
洗浄と真空乾燥を施して、油脂分を除去し、脱脂リゾレ
シチンを得た。Example 2 Soybean lecithin enriched with phosphatidylcholine (
To 100 parts by weight of PC35 (manufactured by True Lecithin Industries), 50 parts by weight of water was added and stirred to obtain a uniform liquid mixture. Then, 0.1% phospholipase A2 preparation (NOVO, Lecitase 10 L) was added to this mixture, and the pH was adjusted to 5.5 to 5.5 with IN sodium hydroxide solution.
The enzyme reaction was carried out at 50 to 60°C for 48 hours while adjusting the temperature to 6.5. Then, the obtained enzyme reaction product was
After vacuum drying at ~60'C to remove moisture, acetone washing and vacuum drying were performed to remove oil and fat content to obtain defatted lysolecithin.
次に、この脱脂リゾレシチン＝２０ｇを、約４Ｏｍｆｌ
のエタノールに？岩屑し、デキストリン＝６０ｇと混合
した後、真空下で溶剤を除去して、リゾレシチンとデキ
ストリンの粉末混合物を調製した。Next, add 20g of this defatted lysolecithin to approximately 4Omfl
to ethanol? After grinding and mixing with 60 g of dextrin, the solvent was removed under vacuum to prepare a powder mixture of lysolecithin and dextrin.
そして、この粉末混合物を５００ ｍｌの抽出容器に入
れ、超臨界二酸化炭素とエタノールの混合溶媒（エタノ
ール比率：１６重量％）を連続的に注入して、Ｌ Ｐ
Ｃの抽出を４時間行なった。抽出条件は、温爪：４０°
Ｃ３圧カニ３０ＭＰａ、溶媒の平均流ｆｆｌ：２０ＯＮ
ｐ／ｈてあった。かかる抽出により得られ、たリゾレシ
チンの量は、５．８ｇであり、収率は２９％であった。Then, this powder mixture was placed in a 500 ml extraction container, and a mixed solvent of supercritical carbon dioxide and ethanol (ethanol ratio: 16% by weight) was continuously injected into the L P
Extraction of C was carried out for 4 hours. Extraction conditions are warm nails: 40°
C3 pressure crab 30MPa, average flow of solvent ffl: 20ON
It was p/h. The amount of lysolecithin obtained by this extraction was 5.8 g, and the yield was 29%.
かくして採取されたりヅレシチンと抽出原料とした脱脂
リゾレシチンについて、組成を分析したところ、第１表
に示す結果か得られ、Ｌ Ｐ Ｇ濃度が８８．１％にま
で高められていることが判った。When the composition of the defatted lysolecithin collected in this manner and used as an extraction raw material was analyzed, the results shown in Table 1 were obtained, and it was found that the LPG concentration was increased to 88.1%.
実施例 ３
実施例２と同様の脱脂リゾレシチン：２０ｇを、約４０
雄のエタノールに溶解し、パーライト（東回パーライト
工業製、ドブコパーライトＮｏ、 ３ ’４ ）３０ｇ
を添加混合した後、真空下で溶剤を除去して、リゾレシ
チンとパーライトとの粉末混合物を調製した。Example 3 Defatted lysolecithin similar to Example 2: 20 g was
30 g of perlite (manufactured by Tokai Perlite Kogyo, Dobukoperlite No. 3'4) dissolved in ethanol
After addition and mixing, the solvent was removed under vacuum to prepare a powder mixture of lysolecithin and perlite.
次いでこの粉末混合物を５００ ｍｌ、の抽出容器に入
れ、液化二酸化炭素とエタノールとの混合溶媒（エタノ
ール比率二８重量％）を連続的に注入して、Ｌ Ｐ Ｇ
の抽出を８時間行なった。抽出条件は、温度＝５°Ｃ１
圧カニ７ＭＰａ、溶媒の平均流量；４０ＯＮｆｆ／ｈと
した。Next, this powder mixture was placed in a 500 ml extraction container, and a mixed solvent of liquefied carbon dioxide and ethanol (ethanol ratio: 28% by weight) was continuously injected to LPG.
The extraction was carried out for 8 hours. The extraction conditions are temperature = 5°C1
The pressure was 7 MPa, and the average flow rate of the solvent was 40 ONff/h.
かくして得られたりヅレシチンの収率は２０．０％であ
った。また、採取されたリゾレシチンの組成を分析した
とごろ、ＬＰＧ濃度は８９．３％と高く、抽出溶媒に液
化二酸化炭素を配合する場合にも、超臨界二酸化炭素を
配合する場合と同様に、良好な結果が得られた。The yield of the thus obtained durecithin was 20.0%. In addition, when we analyzed the composition of the collected lysolecithin, we found that the LPG concentration was as high as 89.3%, indicating that the LPG concentration was as high as 89.3%. The results were obtained.
実施例 ４
市販の粉末卵黄：１００重量部に対して、８０重量部の
水を加えて分散液を作り、この分散液に対して０．１％
のホスホリパーゼＡ２製Ｅ（ＮＯｖＯ社製、レシターゼ
ｌ０Ｌ）を加え、ＩＮ水酸化す１−リウム溶液でｐ Ｈ
５，５〜６．５に調整しながら、５０〜６０°Ｃで２４
時間、酵素反応を行なった。Example 4 Commercially available powdered egg yolk: 80 parts by weight of water was added to 100 parts by weight to make a dispersion, and 0.1% to this dispersion was added.
Phospholipase A2 (Lecitase 10L, manufactured by NOvO) was added, and the pH was adjusted with IN 1-lium hydroxide solution.
24 at 50-60°C while adjusting to 5.5-6.5.
The enzymatic reaction was carried out for an hour.
そして、得られた酵素反応物を５０〜６０°Ｃで真空乾
燥して、リゾ化粉末卵黄を得た。次いで、ごのリゾ化粉
末卵黄： １．００ ｇを、５００ ｍ（ｌの抽出管に
入れ、温度；４０°Ｃ１圧力ニ３０ＭＰａの超臨界二酸
化炭素を用いて、平均流量４０ＯＮβ／ｈで８時間抽出
を行ない、リゾ化粉末卵黄中の油脂骨を除去した。Then, the obtained enzyme reaction product was vacuum dried at 50 to 60°C to obtain a resolized powdered egg yolk. Next, 1.00 g of resolized powdered egg yolk was placed in a 500 m (l) extraction tube, and heated at an average flow rate of 40 ONβ/h for 8 hours using supercritical carbon dioxide at a temperature of 40°C and a pressure of 30 MPa. Extraction was performed to remove fat bones in the resolized powdered egg yolk.
そして、この脱脂されたリゾ化粉末卵黄に対して、温度
：４０°Ｃ１圧力ニ３０ＭＰａ、溶媒の平均流量：４０
ＯＮｆ！、／ｈの抽出条件にて、超臨界酸化炭素とエタ
ノールの／ｌ’を合溶媒（エタノール比率＝１６重量％
）を用いて、ＬＰＣの抽出を４時間行なった。Then, for this defatted resolized powdered egg yolk, temperature: 40° C., pressure: 30 MPa, average flow rate of solvent: 40
ONf! , /h under extraction conditions, supercritical carbon oxide and /l' of ethanol were combined as a solvent (ethanol ratio = 16% by weight).
) was used to extract LPC for 4 hours.
かくして採取されたリゾレシチンと抽出原料とした脱脂
リゾ化粉末卵黄について、組成を分析したところ、第１
表に示す結果が得られ、ＬＰＣ濃度が９１．２％に高め
られていることが判った。When we analyzed the composition of the lysolecithin thus collected and the defatted lysolized powdered egg yolk used as the extraction raw material, we found that the first
The results shown in the table were obtained, and it was found that the LPC concentration was increased to 91.2%.
実施例 ５〜Ｂ
超臨界二酸化炭素と混合するアルコールの種類を変更し
て調製した４種類の抽出溶媒のそれぞれを用いて、実施
例１で調製したリゾレシチンとデギストリンの粉末混合
物の抽出を行なった。Examples 5 to B The powder mixture of lysolecithin and degistrin prepared in Example 1 was extracted using each of four types of extraction solvents prepared by changing the type of alcohol mixed with supercritical carbon dioxide.
各々の抽出において得られたリゾレシチンについて、組
成を分析したところ、第１表に示す結果が得られ、何れ
もＬＰＣ濃度が効果的に高められていることが判った。When the composition of the lysolecithin obtained in each extraction was analyzed, the results shown in Table 1 were obtained, and it was found that the LPC concentration was effectively increased in each case.
また、何れの溶媒の場合でも、ＰＥ、ＰＩは抽出されな
かった。Furthermore, PE and PI were not extracted with any solvent.
従って、炭素数１〜４のアルコールは何れも抽出溶媒と
して使用可能であり、とりわけ、メタノール及びエタノ
ールが良好な溶剤であることが認められた。Therefore, it was found that any alcohol having 1 to 4 carbon atoms can be used as an extraction solvent, and methanol and ethanol are particularly good solvents.
（発明の効果）
以−１−の説明から明らかなように、本発明手法に従え
ば、種々のリゾレシチン及びリゾ化されずに残った種々
の未反応のレシチンを含有する原料リゾレシチンより、
簡単な操作で、且つ良好な収率をもって、効率的にＩ、
ＰＣを抽出することが出来るのである。(Effects of the Invention) As is clear from the explanation in -1- below, according to the method of the present invention, from the raw material lysolecithin containing various lysolecithins and various unreacted lecithins remaining without being lysolized,
Efficiently with simple operation and good yield, I,
It is possible to extract the PC.
従って、本発明手法は、工程の簡略化を図り得て、且つ
良好な生産性を達成し得る、工業生産に適した高濃度Ｌ
ＰＧを含むリゾレシチンの製造法として、極めて利用価
値の高いものである。Therefore, the method of the present invention can simplify the process and achieve good productivity, and can produce high-concentration L suitable for industrial production.
This method is extremely useful as a method for producing lysolecithin containing PG.
第１図は、本発明手法が適用される抽出装置の一例を示
すフローシートである。
２：ボンへ ４＝タンクFIG. 1 is a flow sheet showing an example of an extraction device to which the method of the present invention is applied. 2: To Bon 4 = Tank
Claims (1)
脂した後、液体状態若しくは超臨界状態の二酸化炭素と
炭素数が１〜４のアルコールとからなる混合溶媒を抽出
溶媒として用い、該混合溶媒にて、前記脱脂されたリゾ
レシチンの抽出操作を行なって、その抽出液から前記混
合溶媒を除去することを特徴とする高濃度のリゾホスフ
ァチジルコリンを含むリゾレシチンを採取する方法。After defatting lysolecithin obtained by treating lecithin with an enzyme, a mixed solvent consisting of carbon dioxide in a liquid or supercritical state and an alcohol having 1 to 4 carbon atoms is used as an extraction solvent, and in the mixed solvent, A method for collecting lysolecithin containing a high concentration of lysophosphatidylcholine, which comprises performing an extraction operation on the defatted lysolecithin and removing the mixed solvent from the extract.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2258165A JPH0687751B2 (en) | 1990-09-26 | 1990-09-26 | Method for collecting lysolecithin containing high concentration of lysophosphatidylcholine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2258165A JPH0687751B2 (en) | 1990-09-26 | 1990-09-26 | Method for collecting lysolecithin containing high concentration of lysophosphatidylcholine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04135456A true JPH04135456A (en) | 1992-05-08 |
| JPH0687751B2 JPH0687751B2 (en) | 1994-11-09 |
Family
ID=17316436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2258165A Expired - Fee Related JPH0687751B2 (en) | 1990-09-26 | 1990-09-26 | Method for collecting lysolecithin containing high concentration of lysophosphatidylcholine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0687751B2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5478585A (en) * | 1991-09-03 | 1995-12-26 | Sumitomo Seika Chemicals Co., Ltd. | Process for producing lipoprotein-containing substance having reduced lipid content |
| ES2103238A1 (en) * | 1996-02-22 | 1997-09-01 | Invest De La Ind Agroalimentar | Process for extracting natural products by means of supercritical fluids |
| US5800850A (en) * | 1995-07-07 | 1998-09-01 | Nestec S.A. | Process for reducing spoilage of sterilized liquid products |
| EP0870840A2 (en) * | 1997-04-08 | 1998-10-14 | Tsuji Oil Mill Co., Ltd. | Process for manufacturing vegetable lysolecithins |
| WO2003060112A1 (en) | 2002-01-16 | 2003-07-24 | Novozymes A/S | Lipolytic enzyme variants and method for their production |
| EP1555322A1 (en) | 2000-04-28 | 2005-07-20 | Novozymes A/S | Lipolytic enzyme variant |
| EP2113563A2 (en) | 1998-11-27 | 2009-11-04 | Novozymes A/S | Lipolytic enzyme variants |
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| EP2287296A1 (en) | 2000-06-26 | 2011-02-23 | Novozymes A/S | Lipolytic enzyme |
| WO2004097012A2 (en) | 2003-04-28 | 2004-11-11 | Novozymes A/S | Phospholipase and method of producing it |
| US9670470B2 (en) | 2013-03-21 | 2017-06-06 | Novozymes A/S | Polypeptides having phospholipase A activity and polynucleotides encoding same |
| EP4163354A3 (en) | 2014-03-19 | 2023-08-30 | Novozymes A/S | Polypeptides having phospholipase c activity and polynucleotides encoding same |
| EP3143135B1 (en) | 2014-05-15 | 2019-04-10 | Novozymes A/S | Compositions comprising polypeptides having phospholipase c activity and use thereof |
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1990
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Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5478585A (en) * | 1991-09-03 | 1995-12-26 | Sumitomo Seika Chemicals Co., Ltd. | Process for producing lipoprotein-containing substance having reduced lipid content |
| US5800850A (en) * | 1995-07-07 | 1998-09-01 | Nestec S.A. | Process for reducing spoilage of sterilized liquid products |
| ES2103238A1 (en) * | 1996-02-22 | 1997-09-01 | Invest De La Ind Agroalimentar | Process for extracting natural products by means of supercritical fluids |
| EP0870840A2 (en) * | 1997-04-08 | 1998-10-14 | Tsuji Oil Mill Co., Ltd. | Process for manufacturing vegetable lysolecithins |
| EP0870840A3 (en) * | 1997-04-08 | 1999-09-01 | Tsuji Oil Mill Co., Ltd. | Process for manufacturing vegetable lysolecithins |
| EP2302044A1 (en) | 1998-11-27 | 2011-03-30 | Novozymes A/S | Lipolytic enzyme variants |
| EP2290058A1 (en) | 1998-11-27 | 2011-03-02 | Novozymes A/S | Lipolytic enzyme variants |
| EP2113563A2 (en) | 1998-11-27 | 2009-11-04 | Novozymes A/S | Lipolytic enzyme variants |
| EP2302043A2 (en) | 1998-11-27 | 2011-03-30 | Novozymes A/S | Lipolytic enzyme variants |
| EP2236602A1 (en) | 1998-11-27 | 2010-10-06 | Novozymes A/S | Lipolytic enzyme variants |
| EP2716753A1 (en) | 1998-11-27 | 2014-04-09 | Novozymes A/S | Lipolytic enzyme variants |
| EP2298873A1 (en) | 1998-11-27 | 2011-03-23 | Novozymes A/S | Lipolytic enzyme variants |
| EP2290059A1 (en) | 1998-11-27 | 2011-03-02 | Novozymes A/S | Lipolytic enzyme variants |
| EP2287297A1 (en) | 1998-11-27 | 2011-02-23 | Novozymes A/S | Lipolytic enzyme variants |
| EP2287298A1 (en) | 1998-11-27 | 2011-02-23 | Novozymes A/S | Lipolytic enzyme variants |
| EP2258853A1 (en) | 2000-04-28 | 2010-12-08 | Novozymes A/S | Lipolytic enzyme variant |
| EP2258835A1 (en) | 2000-04-28 | 2010-12-08 | Novozymes A/S | Lipolytic enzyme variant |
| EP2258852A1 (en) | 2000-04-28 | 2010-12-08 | Novozymes A/S | Lipolytic enzyme variant |
| EP2236611A1 (en) | 2000-04-28 | 2010-10-06 | Novozymes A/S | Lipolytic enzyme variant |
| EP1555322A1 (en) | 2000-04-28 | 2005-07-20 | Novozymes A/S | Lipolytic enzyme variant |
| EP2295556A2 (en) | 2002-01-16 | 2011-03-16 | Novozymes A/S | Lipolytic enzymes variants and methods for their production |
| WO2003060112A1 (en) | 2002-01-16 | 2003-07-24 | Novozymes A/S | Lipolytic enzyme variants and method for their production |
| US9115346B2 (en) | 2002-01-16 | 2015-08-25 | Novozymes A/S | Lipolytic enzymes |
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| Publication number | Publication date |
|---|---|
| JPH0687751B2 (en) | 1994-11-09 |
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