JP2722007B2 - Castor oil derivative - Google Patents
Castor oil derivativeInfo
- Publication number
- JP2722007B2 JP2722007B2 JP2085163A JP8516390A JP2722007B2 JP 2722007 B2 JP2722007 B2 JP 2722007B2 JP 2085163 A JP2085163 A JP 2085163A JP 8516390 A JP8516390 A JP 8516390A JP 2722007 B2 JP2722007 B2 JP 2722007B2
- Authority
- JP
- Japan
- Prior art keywords
- castor oil
- etherified
- hydrogenated castor
- group
- alkyl
- 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 - Fee Related
Links
- 239000004359 castor oil Substances 0.000 title claims description 63
- 235000019438 castor oil Nutrition 0.000 title claims description 63
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 title claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 239000000470 constituent Substances 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- 239000008157 edible vegetable oil Substances 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000005313 fatty acid group Chemical group 0.000 claims description 2
- -1 acyl ester Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 102000019280 Pancreatic lipases Human genes 0.000 description 2
- 108050006759 Pancreatic lipases Proteins 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 229940040461 lipase Drugs 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 229940116369 pancreatic lipase Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YQXHKIKYTYUEJU-DTQAZKPQSA-N (E)-12-hydroxyoctadec-2-enoic acid Chemical compound CCCCCCC(O)CCCCCCCC\C=C\C(O)=O YQXHKIKYTYUEJU-DTQAZKPQSA-N 0.000 description 1
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- BLAKAEFIFWAFGH-UHFFFAOYSA-N acetyl acetate;pyridine Chemical compound C1=CC=NC=C1.CC(=O)OC(C)=O BLAKAEFIFWAFGH-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 229940125722 laxative agent Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Landscapes
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
Description
【発明の詳細な説明】 （ａ）産業上の利用分野 本発明は食用に供し得るひまし油誘導体に関わる。The present invention relates to edible castor oil derivatives.
（ｂ）従来の技術 ひまし油が通常の食用油と大きく異なるのは12−ヒド
ロキシ−オクタデセン酸をその構成脂肪酸の主成分とす
る点であり、主に下剤、香粧品、塗料などの工業用原料
に用いられている。そして加水分解されにくい等の理由
から我国では食用に供されることがなく、食用化のため
の研究もほとんどなされていない。(B) Prior art Castor oil is greatly different from ordinary edible oil in that 12-hydroxy-octadecenoic acid is a main component of its constituent fatty acids, and is mainly used for industrial raw materials such as laxatives, cosmetics, and paints. Used. In Japan, it is hardly hydrolyzed and is not used for food, and there is almost no research on edible use.
（ｃ）発明が解決しようとする課題 上述の様に、ひまし油はこれを食した場合、下痢が起
こり、食品としての価値がないものであった。本発明の
目的は、このようなひまし油の性状を改変し、優れた消
化性をもつ食用のひまし油誘導体を得ることである。(C) Problems to be Solved by the Invention As described above, when castor oil is eaten, it causes diarrhea and has no value as a food. An object of the present invention is to modify the properties of such castor oil to obtain an edible castor oil derivative having excellent digestibility.
（ｄ）課題を解決するための手段 本発明者らは鋭意研究を重ねた結果、ひまし油または
水素添加したひまし油（以下、水添ひまし油という）の
構成脂肪酸の水酸基をメチルエーテル化（メトキシ化）
あるいはアセチルエステル化等のアルキルエーテル化ま
たはアシルエステル化したひまし油誘導体は、通常のひ
まし油あるいは水添ひまし油に比べ著しくリパーゼによ
る加水分解率が上昇するということを見出した。(D) Means for Solving the Problems As a result of intensive studies, the present inventors have methyl etherified (methoxylated) hydroxyl groups of constituent fatty acids of castor oil or hydrogenated castor oil (hereinafter referred to as hydrogenated castor oil).
Alternatively, it has been found that a castor oil derivative subjected to alkyl etherification such as acetyl esterification or acyl esterification has a significantly increased lipase hydrolysis rate as compared with ordinary castor oil or hydrogenated castor oil.
本発明はかかる知見に基づいて完成されたもので、ひ
まし油の構成脂肪酸の12位が水酸基がアルキルエーテル
化（但しアルキル基の炭素数は１〜４）されたひまし油
エーテル化物、水添ひまし油の構成脂肪酸の12位が水酸
基がアルキルエーテル化（但しアルキル基の炭素数は１
〜４）またはアシルエステル化（但しアシル基の炭素数
は２〜４）された水添ひまし油エーテル化物または水添
ひまし油エステル化物に係り、また、ひまし油の構成脂
肪酸の12位が水酸基がアルキルエーテル化（但しアルキ
ル基の炭素数は１〜４）されたひまし油エーテル化物、
前記水酸基がアシルエステル化（但しアシル基の炭素数
は２〜４）されたひまし油エステル化物、水添ひまし油
の構成脂肪酸の12位が水酸基がアルキルエーテル化（但
しアルキル基の炭素数は１〜４）された水添ひまし油エ
ーテル化物、および前記水酸基がアシルエステル化（但
しアシル基の炭素数は２〜４）された水添ひまし油エス
テル化物からなる群より選ばれたひまし油誘導体を含ん
でなる食用油に関するものである。The present invention has been completed on the basis of the above findings, and is a structure of castor oil etherified product in which the hydroxyl group at the 12-position of the constituent fatty acids of castor oil is alkyl etherified (the alkyl group has 1 to 4 carbon atoms), and hydrogenated castor oil. The hydroxyl group is alkyl etherified at the 12-position of the fatty acid (however, the alkyl group has 1 carbon atom).
To 4) or acyl esterified (where the carbon number of the acyl group is 2 to 4) hydrogenated castor oil etherified product or hydrogenated castor oil esterified product, and the 12th position of the constituent fatty acid of castor oil has an alkyl etherified hydroxyl group. Castor oil etherified (provided that the alkyl group has 1 to 4 carbon atoms),
A castor oil esterified product in which the hydroxyl group is acyl-esterified (the acyl group has 2 to 4 carbon atoms), and the 12th position of the constituent fatty acids of hydrogenated castor oil is an alkyl etherified hydroxyl group (wherein the alkyl group has 1 to 4 carbon atoms). Edible oil comprising an etherified hydrogenated castor oil product and a castor oil derivative selected from the group consisting of a hydrogenated castor oil esterified product in which the hydroxyl group is acyl-esterified (the acyl group has 2 to 4 carbon atoms). It is about.
ここで行う水酸基のアルキルエーテル化またはアシル
エステル化は、前者については炭素数が１〜４、好まし
くは１のアルキル基をエーテル化できるもの、後者につ
いては炭素数が２〜４、好ましくは２のアシル基をエス
テル化できるものであればいかなる手法を用いても良
い。以下の実施例に化学合成方法の１例を示すが、本発
明はこれらの方法に限定されるものではない。The alkyl etherification or acyl esterification of the hydroxyl group performed here can be performed by etherifying an alkyl group having 1 to 4 carbon atoms, preferably 1 alkyl group, and 2 to 4 carbon atoms, preferably 2 carbon atoms, with respect to the latter. Any method may be used as long as the acyl group can be esterified. The following examples show one example of a chemical synthesis method, but the present invention is not limited to these methods.
本発明の食用油は、前記のひまし油エーテル化物、ひ
まし油エステル化物、水添ひまし油エーテル化物、およ
び水添ひまし油エステル化物からなる群より選ばれたひ
まし油誘導体と、公知の食用油脂例えば大豆油、菜種
油、コーン油、綿実油、ひまわり油、サフラワー油、パ
ーム油、ゴマ油、オリーブ油、牛脂、豚脂、魚油、これ
らに分別、水素添加、エステル交換等の処理を施した加
工油脂とを任意の割合で混合することにより調製でき
る。The edible oil of the present invention is a castor oil derivative selected from the group consisting of the castor oil etherified product, castor oil esterified product, hydrogenated castor oil etherified product, and hydrogenated castor oil esterified product, and known edible oils and fats such as soybean oil, rapeseed oil, and the like. Corn oil, cottonseed oil, sunflower oil, safflower oil, palm oil, sesame oil, olive oil, beef tallow, lard, fish oil, mixed with any of these processed oils and fats that have been subjected to separation, hydrogenation, transesterification, etc. Can be prepared.
（ｅ）実施例 実施例１ 水添ひまし油のメチルエーテル化 市販の水添ひまし油2gをジメチルスルホキシド400ml
に溶解しておき、水素化ナトリウム5gを窒素気流中でジ
メチルスルホキシド300mlと65〜70℃で１時間撹拌した
ものと混合する。これを窒素気流中で37℃、６時間攪拌
し、室温にもどしてヨウ化メチル250gを加えて12時間攪
拌する。これを水で希釈した後、クロロホルムで抽出し
水洗、乾燥後減圧濃縮して構成脂肪酸の12位が水酸基が
メチルエーテル化された水添ひまし油エーテル化物を得
た。(E) Examples Example 1 Methyl etherification of hydrogenated castor oil 2 g of commercially available hydrogenated castor oil was added to 400 ml of dimethyl sulfoxide.
And 5 g of sodium hydride are mixed with 300 ml of dimethyl sulfoxide and stirred at 65 to 70 ° C. for 1 hour in a nitrogen stream. The mixture is stirred in a nitrogen stream at 37 ° C. for 6 hours, cooled to room temperature, added with 250 g of methyl iodide, and stirred for 12 hours. This was diluted with water, extracted with chloroform, washed with water, dried and concentrated under reduced pressure to obtain a hydrogenated castor oil etherified product in which the hydroxyl group at position 12 of the constituent fatty acid was methyl etherified.
実施例２ 水添ひまし油のアセチルエステル化 市販の水添ひまし油1gを無水酢酸−ピリジン（1:2）
液を300ml加え、37℃で24時間放置して、アセチル化を
行い構成脂肪酸の12位が水酸基がアセチルエステル化さ
れた水添ひまし油エステル化物を得た。Example 2 Acetyl esterification of hydrogenated castor oil 1 g of commercially available hydrogenated castor oil was added to acetic anhydride-pyridine (1: 2).
300 ml of the solution was added, and the mixture was allowed to stand at 37 ° C. for 24 hours for acetylation to obtain a hydrogenated castor oil esterified product in which the hydroxyl group at position 12 of the constituent fatty acid was acetyl esterified.
実施例３ 実施例１および２で得られた水添ひまし油のメチルエ
ーテル化物または水添ひまし油アセチルエステル化物に
ついて、J.Sampugnaらの方法（Lipids,2,397（1967））
を用いてブタ膵臓リパーゼと反応させ加水分解率の測定
を行った。すなわち、メチル化またはアセチル化された
水添ひまし油5mgに0.25モルトリスHCl緩衝液（５％アラ
ビアガムを含む、pH8）、45％CaCl2溶液1.0ml及び１％S
odium Taulocholate 0.4mlを加え均質化したものを37℃
で５分間保持した後、ブタ膵臓リパーゼ（6mg/ml）液を
2mlを加え37℃で反応させた。反応開始後5,15,30後にそ
れぞれ反応液を1mlとりヘキサン：エタノール:70％H2SO
4（300:200:1）液を5ml加え、O.Hirayamaの方法（Agri
c.Biol.Chem.,36,1831（1972））を用いてRohodamine-6
G法で反応率を測定した。その結果を表−１に示す。対
照として市販のひまし油および水添ひまし油を用いて同
時に測定を行った。Example 3 The method of J. Sampugna et al. (Lipids, 2, 397 (1967)) was applied to the methyl etherified product or hydrogenated castor oil acetyl esterified product of hydrogenated castor oil obtained in Examples 1 and 2.
Was used to react with porcine pancreatic lipase, and the hydrolysis rate was measured. That is, in 5 mg of methylated or acetylated hydrogenated castor oil, 0.25 mol of Tris HCl buffer (containing 5% gum arabic, pH 8), 1.0 ml of 45% CaCl 2 solution and 1% S
Add 0.4ml odium Taulocholate and homogenize to 37 ℃
After holding for 5 minutes in the pancreatic lipase (6 mg / ml) solution
2 ml was added and reacted at 37 ° C. After 5, 15, and 30 after the start of the reaction, 1 ml of each reaction solution was taken, and hexane: ethanol: 70% H 2 SO
4 Add 5 ml of the (300: 200: 1) solution and use the O.Hirayama method (Agri
c. Biol. Chem., 36, 1831 (1972))
The reaction rate was measured by the G method. Table 1 shows the results. The measurements were performed simultaneously using commercially available castor oil and hydrogenated castor oil as controls.
表−１のように、水添ひまし油メチルエーテル化物ある
いは水添ひまし油アセチルエステル化物はいずれも通常
のひまし油あるいは水添ひまし油に比べ著しく良好な加
水分解性を示した。 As shown in Table 1, both the hydrogenated castor oil methyl etherified product and the hydrogenated castor oil acetyl esterified product showed significantly better hydrolyzability than ordinary castor oil or hydrogenated castor oil.
実施例４ 実施例２で得られた水添ひまし油アセチルエステル化
物または実施例１で得られた水添ひまし油メチルエーテ
ル化物と菜種サラダ油との等重量混合油約5mgを用い、
実施例３に記載の方法により加水分解率を測定した。こ
の結果、30分間反応後の加水分解率は水添ひまし油アセ
チルエステル化物混合油の場合95.1％であり、水添ひま
し油メチルエーテル化物混合油の場合82.0％であった。Example 4 Using about 5 mg of an equal weight mixed oil of the hydrogenated castor oil acetyl esterified product obtained in Example 2 or the hydrogenated castor oil methyl etherified product obtained in Example 1 and rapeseed salad oil,
The hydrolysis rate was measured by the method described in Example 3. As a result, the hydrolysis ratio after the reaction for 30 minutes was 95.1% in the case of the hydrogenated castor oil acetyl esterified mixed oil, and was 82.0% in the case of the hydrogenated castor oil methyl etherified mixed oil.
（ｆ）発明の効果 本発明によれば、リパーゼによる加水分解率が通常の
ひまし油あるいは水添ひまし油に比べ著しく向上したひ
まし油誘導体が得られ、このものは食用油としての良好
な適性を有している。(F) Effects of the Invention According to the present invention, a castor oil derivative whose hydrolysis rate by lipase is significantly improved as compared with ordinary castor oil or hydrogenated castor oil is obtained, which has good suitability as an edible oil. I have.
Claims (3)
ルキルエーテル化（但しアルキル基の炭素数は１〜４）
されたひまし油エーテル化物。1. A hydroxyl group is alkyl etherified at the 12-position of the constituent fatty acids of castor oil (provided that the alkyl group has 1 to 4 carbon atoms).
Castor oil etherified.
がアルキルエーテル化（但しアルキル基の炭素数は１〜
４）またはアシルエステル化（但しアシル基の炭素数は
２〜４）された水添ひまし油エーテル化物または水添ひ
まし油エステル化物。(2) The hydroxyl group at the 12-position of the fatty acid constituting hydrogenated castor oil is alkyl-etherified (provided that the alkyl group has 1 to 1 carbon atom).
4) A hydrogenated castor oil etherified product or a hydrogenated castor oil esterified product obtained by acyl esterification (the acyl group has 2 to 4 carbon atoms).
ルキルエーテル化（但しアルキル基の炭素数は１〜４）
されたひまし油エーテル化物、前記水酸基がアシルエス
テル化（但しアシル基の炭素数は２〜４）されたひまし
油エステル化物、水添ひまし油の構成脂肪酸の12位が水
酸基がアルキルエーテル化（但しアルキル基の炭素数は
１〜４）された水添ひまし油エーテル化物、および前記
水酸基がアシルエステル化（但しアシル基の炭素数は２
〜４）された水添ひまし油エステル化物からなる群より
選ばれたひまし油誘導体を含んでなる食用油。3. A hydroxyl group is alkyl etherified at the 12-position of the constituent fatty acids of castor oil (provided that the alkyl group has 1 to 4 carbon atoms).
Castor oil etherified product, castor oil esterified product in which the above-mentioned hydroxyl group is acyl-esterified (however, the acyl group has 2 to 4 carbon atoms), the hydroxyl group is alkyl-etherified at the 12-position of the constituent fatty acid of hydrogenated castor oil (excluding the alkyl group A hydrogenated castor oil etherified product having 1 to 4 carbon atoms, and an acyl ester of the hydroxyl group (wherein the acyl group has 2 carbon atoms)
4) An edible oil comprising a castor oil derivative selected from the group consisting of hydrogenated castor oil esterified products.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2085163A JP2722007B2 (en) | 1990-03-30 | 1990-03-30 | Castor oil derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2085163A JP2722007B2 (en) | 1990-03-30 | 1990-03-30 | Castor oil derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03281698A JPH03281698A (en) | 1991-12-12 |
| JP2722007B2 true JP2722007B2 (en) | 1998-03-04 |
Family
ID=13850994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2085163A Expired - Fee Related JP2722007B2 (en) | 1990-03-30 | 1990-03-30 | Castor oil derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2722007B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5715559B2 (en) * | 2008-05-14 | 2015-05-07 | カウンシル オブ サイエンティフィック アンド インダストリアル リサーチ | 9,10,12-Triacyloxyoctadecanoic acid alkyl ester and 9,10,12-triacyloxyoctadecanoic acid alkyl ester-rich fatty acid alkyl ester mixture and process for producing them |
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| JP2592622B2 (en) * | 1987-11-12 | 1997-03-19 | 伊藤製油株式会社 | Polyurethane manufacturing method |
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| JPH03281698A (en) | 1991-12-12 |
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