JPH056553B2 - - Google Patents
Info
- Publication number
- JPH056553B2 JPH056553B2 JP3023185A JP3023185A JPH056553B2 JP H056553 B2 JPH056553 B2 JP H056553B2 JP 3023185 A JP3023185 A JP 3023185A JP 3023185 A JP3023185 A JP 3023185A JP H056553 B2 JPH056553 B2 JP H056553B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- phosphatidylcholine
- porous resin
- phosphatide
- column
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 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 claims description 20
- 239000011347 resin Substances 0.000 claims description 15
- 229920005989 resin Polymers 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000000397 acetylating effect Effects 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 230000021736 acetylation Effects 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- -1 aqueous ethanol (see Chemical compound 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000008349 purified phosphatidyl choline Substances 0.000 description 2
- 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 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はホスフアチジルコリンの製造方法に関
する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing phosphatidylcholine.
ホスフアチドは、食品、化粧品及び医薬品に広
く用いられてきており、その中で殊に油を含有し
ていない高純度のホスフアチジルコリンは医薬品
として特に必要とされている。 Phosphatides have been widely used in foods, cosmetics, and pharmaceuticals, and among them, highly purified oil-free phosphatidylcholine is particularly needed as a pharmaceutical product.
高純度のホスフアチジルコリンを得るには、粗
ホスフアチドをアセトン及びアルコール特に含水
エタノールによる処理により脱油することが行わ
れている（例えば特公昭59−51253号参照）。
In order to obtain highly pure phosphatidylcholine, crude phosphatide is deoiled by treatment with acetone and an alcohol, particularly aqueous ethanol (see, for example, Japanese Patent Publication No. 51253/1983).
これらの処理により得られた脱油粗ホスフアチ
ドをさらに精製するために、従来から種々の方法
が採用されてきた。例えば酸化アルミナを用いる
クロマトグラフイ処理があるが（ドイツ特許第
1617679号及び同第1617680号参照）、トリグリセ
リドの分離が困難でありその上用いた酸化アルミ
ナの再生使用が行われ難いという欠点がある。一
方、シリカゲルを用いるクロマトグラフイ処理も
行われている。この際、溶離液にアンモニア性ア
ルコールを用いているが、脱着が難しく又回収率
も低い。またはカラムの内部を約60〜90℃に加熱
しなければならず、処理が容易でない。そしてこ
れらのクロマトグラフイ処理では高純度のホスフ
アチジルコリンを得ることが難しい。又、多孔性
樹脂を用いたクロマトグラフイ処理はホスフアチ
ジルコリンと他の成分との分離が難しく、何回も
精製処理を繰り返す必要があつた。 In order to further purify the deoiled crude phosphatide obtained by these treatments, various methods have been employed heretofore. For example, there is a chromatographic process using alumina oxide (German patent no.
Nos. 1,617,679 and 1,617,680), it is difficult to separate triglycerides, and furthermore, it is difficult to recycle the alumina oxide used. On the other hand, chromatography using silica gel has also been carried out. At this time, ammoniacal alcohol is used as the eluent, but desorption is difficult and the recovery rate is low. Alternatively, the inside of the column must be heated to approximately 60-90°C, which is not easy to process. It is difficult to obtain highly pure phosphatidylcholine with these chromatographic treatments. Furthermore, in the chromatography treatment using a porous resin, it is difficult to separate phosphatidylcholine from other components, and it is necessary to repeat the purification treatment many times.
本発明は、多孔性樹脂を用いるクロマトグラフ
イによりホスフアチジルコリンを合理的に精製す
ることにある。
The present invention is to rationally purify phosphatidylcholine by chromatography using a porous resin.
発明者らは脱油粗ホスフアチドのアセチル化を
行うと、ホスフアチジルコリン以外の不純物即ち
長鎖のアルコール等がアセチル化され、その結
果、多孔性樹脂のカラムクロマトグラフイにより
ホスフアチジルコリンとの分離が容易に行われる
ことを見出した。
When the inventors acetylated the deoiled crude phosphatide, impurities other than phosphatidylcholine, such as long-chain alcohols, were acetylated, and as a result, they were separated into phosphatidylcholine by porous resin column chromatography. It was found that the separation was easily carried out.
即ち、本発明はアセトン及びアルコール処理を
した脱油粗ホスフアチドをアセチル化し、得られ
る反応生成物を多孔性樹脂を用いるクロマトグラ
フイにより精製処理を行うホスフアチジルコリン
の製造方法に関する。 That is, the present invention relates to a method for producing phosphatidylcholine, which comprises acetylating deoiled crude phosphatide treated with acetone and alcohol, and purifying the resulting reaction product by chromatography using a porous resin.
本発明において用いられる粗ホスフアチドは例
えば大豆、落花生、ヒマワリ又はナタネなどの種
子の如き植物から得られ、これらは約50〜60重量
％のホスフアチド、約30〜40重量％の中性油及び
遊離脂肪酸、約５〜10重量％の単糖類、二糖類又
は多糖類、そして約１〜２重量％のステロール、
ワツクス、アミノ酸及びペプチドよりなる。これ
は、中性油及び遊離脂肪酸を含有しているので、
これらを除去する必要があるため、アセトン処理
（例えば米国特許第3268335号参照）及びアルコー
ル例えばエタノール処理（例えば米国特許第
2945869号、同第2724649号参照）を行う。これら
の処理は、種々の方法で行われるが、例えば室温
で溶媒を加え撹拌することにより行われる。得ら
れた脱油粗ホスフアチドの組成の例としては、ホ
スフアチジルコリン40〜50重量％、ホスフアチジ
ルエタノールアミン25〜30重量％、その他20〜35
重量％あるいはホスフアチジルコリン50〜60重量
％、ホスフアチジルエタノールアミン25〜30重量
％、その他10〜25重量％またさらにはホスフアチ
ジルコリン15〜25重量％、ホスフアチジルエタノ
ールアミン15〜20重量％、イノシトール15〜20重
量％、その他35〜55重量％等がある。 The crude phosphatides used in the present invention are obtained from plants such as seeds of soybean, peanut, sunflower or rapeseed, which contain about 50-60% by weight of phosphatides, about 30-40% by weight of neutral oils and free fatty acids. , about 5-10% by weight of monosaccharides, disaccharides or polysaccharides, and about 1-2% by weight of sterols,
Consists of wax, amino acids and peptides. Because it contains neutral oils and free fatty acids,
These need to be removed by treatment with acetone (see e.g. US Pat. No. 3,268,335) and treatment with alcohols such as ethanol (see e.g. US Pat.
2945869 and 2724649). These treatments can be carried out in various ways, for example by adding a solvent and stirring at room temperature. Examples of the composition of the resulting deoiled crude phosphatide include 40 to 50% by weight of phosphatidylcholine, 25 to 30% by weight of phosphatidylethanolamine, and 20 to 35% by weight of phosphatidylethanolamine.
% by weight or 50-60% by weight of phosphatidylcholine, 25-30% by weight of phosphatidylethanolamine, 10-25% by weight of others or even 15-25% by weight of phosphatidylcholine, 15% by weight of phosphatidylethanolamine 20% by weight, inositol 15-20% by weight, and others 35-55% by weight.
本発明では上述の脱油粗ホスフアチドをアセチ
ル化する。アセチル化は、従来行われているアセ
チル化方法で行うことが出来る。例えばアセチル
化剤として無水酢酸を用い少量のトリエチルアミ
ンの存在下で行う。無水酢酸の量は脱油粗ホスフ
アチドに対して約１〜３重量倍好ましくは1.2〜
2.5重量倍であり、反応は脱油粗ホスフアチドを
有機溶媒例えばｎ−ヘキサンに溶解し、室温又は
室温よりやや高い温度で行われる。 In the present invention, the above-described crude deoiled phosphatide is acetylated. Acetylation can be performed by a conventional acetylation method. For example, acetic anhydride is used as the acetylating agent in the presence of a small amount of triethylamine. The amount of acetic anhydride is about 1 to 3 times the weight of the deoiled crude phosphatide, preferably 1.2 to 3 times the weight of the deoiled crude phosphatide.
The reaction is carried out by dissolving the deoiled crude phosphatide in an organic solvent such as n-hexane at room temperature or a temperature slightly higher than room temperature.
アセチル化した反応生成物を含水有機溶媒例え
ばメタノール又はエタノールに溶解し、多孔性樹
脂を充填したカラムに通す。用いられる多孔性樹
脂は、例えばスチレンとジビニルベンゼンとの共
重合体よりなり商品名としてはHP−20（三菱化
成(株)社製）などが知られている。カラムには、反
応生成物の溶解に使用した含水有機溶媒もしくは
それより若干含水量の多い有機溶媒で多孔性樹脂
を予め充填しておき前記のアセチル化物をカラム
に仕込む。 The acetylated reaction product is dissolved in a water-containing organic solvent such as methanol or ethanol and passed through a column packed with porous resin. The porous resin used is, for example, a copolymer of styrene and divinylbenzene, and its trade name is HP-20 (manufactured by Mitsubishi Kasei Corporation). The column is filled in advance with a porous resin using the water-containing organic solvent used to dissolve the reaction product or an organic solvent with a slightly higher water content than that, and the acetylated product is charged into the column.
カラムの展開溶出は、当初比較的含水量の高い
例えば含水量10％近い有機溶媒を供給し初溜分と
して不純物を除去する。この際アセチル化時の試
薬を除去することなく反応液全体を濃縮したアセ
チル化物であつても、初溜分としてこれらの不純
物を除去し得る。ホスフアチジルコリンを含む所
謂本溜区分は凡ね含水率３〜５％程度の溜分とし
て得られる。得られた本溜溶離液を集め濃縮する
と高純度例えば100重量％のホスフアチジルコリ
ンを高回収率で得ることが出来る。 For column development and elution, an organic solvent with a relatively high water content, for example, water content of approximately 10%, is initially supplied to remove impurities as an initial distillate. At this time, even if the acetylated product is obtained by concentrating the entire reaction solution without removing the reagent for acetylation, these impurities can be removed as the initial distillate. The so-called main fraction containing phosphatidylcholine is generally obtained as a fraction with a water content of about 3 to 5%. When the obtained main eluate is collected and concentrated, highly purified phosphatidylcholine, for example, 100% by weight, can be obtained at a high recovery rate.
本発明によれば、多孔性樹脂を用いてホスフア
チジルコリンと溶離が、溶離液の含水量を変化す
るだけで容易に行うことが出来、しかも高純度の
ホスフアチジルコリンを高い収量で得る。
According to the present invention, elution of phosphatidylcholine using a porous resin can be easily performed by simply changing the water content of the eluent, and moreover, highly purified phosphatidylcholine can be obtained in a high yield. .
又、多孔性樹脂を用いる処理が加熱することな
く、室温で行うことが出来る。その上、使用した
多孔性樹脂は、何等特殊な方法を行うことなく、
再生して繰返し用いることが、出来る。 Further, the treatment using the porous resin can be carried out at room temperature without heating. Moreover, the porous resin used can be used without any special method.
It can be played and used repeatedly.
次に、実施例を示す。 Next, examples will be shown.
実施例 １
(A) 粗ホスフアチド（ホスフアチジルコリン含有
率60重量％、ホスフアチジルエタノールアミン
28％、リゾレシチンその他12％（うち油脂分１
％以下））1.77ｇをｎ−ヘキサン20ml溶液とし、
無水酢酸2.3ｇを加え、氷冷下撹拌しながらト
リエチルアミン0.3ｇを滴下させた。滴下終了
後、室温で２時間撹拌を続けた後ｎ−ヘキサ
ン、過剰の無水酢酸、トリエチルアミンを減圧
下50℃以下にて留去し、アセチル化ホスフアチ
ド2.83ｇを得た。
Example 1 (A) Crude phosphatide (phosphatidylcholine content 60% by weight, phosphatidylethanolamine
28%, lysolecithin and other 12% (including oil and fat 1)
% or less)) 1.77g in 20ml of n-hexane solution,
2.3 g of acetic anhydride was added, and 0.3 g of triethylamine was added dropwise while stirring under ice cooling. After completion of the dropwise addition, stirring was continued for 2 hours at room temperature, and then n-hexane, excess acetic anhydride, and triethylamine were distilled off under reduced pressure at 50° C. or lower to obtain 2.83 g of acetylated phosphatide.
(A)で得られたアセチル化ホスフアチド2.83ｇを
含水量15容積％のメタノール溶液９mlに溶解し、
カラム上においた。 2.83 g of acetylated phosphatide obtained in (A) was dissolved in 9 ml of methanol solution with a water content of 15% by volume,
placed on the column.
カラムは内径2.2cm、高さ20cmになる様に多孔
性樹脂（スチレン・ジビニルベンゼン共樹脂）
（HP−20）をあらかじめ上記と同様な含水メタ
ノール溶液を使つて充填しておいた。含水量を15
容量％から５容量％迄、段階的に減少させて溶出
した。５容量％含水メタノールでの溶出液1.2
を集め、50℃以下で濃縮すると淡黄色ワツクス
0.70ｇ（ホスフアチジルコリン含有率100重量％、
ホスフアチジルコリン精製回収率65.8重量％）を
得た。 The column is made of porous resin (styrene/divinylbenzene co-resin) so that the inner diameter is 2.2 cm and the height is 20 cm.
(HP-20) was filled in advance using the same water-containing methanol solution as above. water content 15
Elution was performed in a stepwise manner from % by volume to 5% by volume. Eluate 1.2 with 5% by volume aqueous methanol
When collected and concentrated at below 50℃, it becomes a pale yellow wax.
0.70g (phosphatidylcholine content 100% by weight,
A phosphatidylcholine purification recovery rate of 65.8% by weight was obtained.
実施例 ２
実施例１(A)で得られたアセチル化ホスフアチド
2.83ｇを含水量18容積％のエタノール溶液９mlに
溶解し、カラム上においた。Example 2 Acetylated phosphatide obtained in Example 1(A)
2.83 g was dissolved in 9 ml of an ethanol solution with a water content of 18% by volume and placed on the column.
カラムは内径2.2cm、高さ20cmになる様に多孔
性樹脂（HP−20）（スチレンとジビニルベンゼ
ン共樹脂）をあらかじめ上記と同様な含水メタノ
ール溶液を使つて充填しておいた。含水量を18容
量％から10容量％迄、段階的に減少させて溶出し
た。10容量％含水メタノールでの溶出液300mlを
集め、50℃以下で濃縮すると淡黄色ワツクス0.56
ｇ（ホスフアチジルコリン含有率100重量％、ホ
スフアチジルコリン精製回収率52.6重量％）を得
た。 The column was filled in advance with a porous resin (HP-20) (styrene and divinylbenzene co-resin) to have an inner diameter of 2.2 cm and a height of 20 cm using the same hydrous methanol solution as above. Elution was carried out by decreasing the water content stepwise from 18% by volume to 10% by volume. Collect 300ml of the eluate with 10% by volume aqueous methanol and concentrate at below 50°C to obtain a pale yellow wax of 0.56%.
g (phosphatidylcholine content 100% by weight, phosphatidylcholine purification recovery rate 52.6% by weight).
Claims (1)
スフアチドをアセチル化し、得られた反応生成物
を多孔性樹脂を用いるクロマトグラフイにより精
製処理することを特徴とするホスフアチジルコリ
ンを製造方法。1. A method for producing phosphatidylcholine, which comprises acetylating deoiled crude phosphatide treated with acetone and alcohol, and purifying the resulting reaction product by chromatography using a porous resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3023185A JPS61191689A (en) | 1985-02-20 | 1985-02-20 | Production of phosphatidylcholine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3023185A JPS61191689A (en) | 1985-02-20 | 1985-02-20 | Production of phosphatidylcholine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61191689A JPS61191689A (en) | 1986-08-26 |
| JPH056553B2 true JPH056553B2 (en) | 1993-01-26 |
Family
ID=12297933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3023185A Granted JPS61191689A (en) | 1985-02-20 | 1985-02-20 | Production of phosphatidylcholine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61191689A (en) |
-
1985
- 1985-02-20 JP JP3023185A patent/JPS61191689A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61191689A (en) | 1986-08-26 |
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