JPH01163176A - Vitamin e palmitoleic acid ester and production thereof - Google Patents
Vitamin e palmitoleic acid ester and production thereofInfo
- Publication number
- JPH01163176A JPH01163176A JP32197987A JP32197987A JPH01163176A JP H01163176 A JPH01163176 A JP H01163176A JP 32197987 A JP32197987 A JP 32197987A JP 32197987 A JP32197987 A JP 32197987A JP H01163176 A JPH01163176 A JP H01163176A
- Authority
- JP
- Japan
- Prior art keywords
- vitamin
- palmitoleic acid
- formula
- acid ester
- production
- 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
- SECPZKHBENQXJG-FPLPWBNLSA-N (Z)-Palmitoleic acid Natural products CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 title claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 235000021319 Palmitoleic acid Nutrition 0.000 title abstract description 24
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 title abstract description 24
- -1 palmitoleic acid ester Chemical class 0.000 title description 9
- 229940088594 vitamin Drugs 0.000 title description 2
- 229930003231 vitamin Natural products 0.000 title description 2
- 235000013343 vitamin Nutrition 0.000 title description 2
- 239000011782 vitamin Substances 0.000 title description 2
- 150000003722 vitamin derivatives Chemical class 0.000 title 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims abstract description 45
- 229930003427 Vitamin E Natural products 0.000 claims abstract description 25
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims abstract description 25
- 235000019165 vitamin E Nutrition 0.000 claims abstract description 25
- 229940046009 vitamin E Drugs 0.000 claims abstract description 25
- 239000011709 vitamin E Substances 0.000 claims abstract description 25
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 24
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 238000010992 reflux Methods 0.000 abstract description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 206010059245 Angiopathy Diseases 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- VZQFJZYVQNXVRY-FPLPWBNLSA-N (z)-hexadec-9-enoyl chloride Chemical compound CCCCCC\C=C/CCCCCCCC(Cl)=O VZQFJZYVQNXVRY-FPLPWBNLSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 210000002374 sebum Anatomy 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 208000010445 Chilblains Diseases 0.000 description 1
- 206010008528 Chillblains Diseases 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 208000001034 Frostbite Diseases 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
この発明は、新規なビタミンＥパルミトレイン酸エステ
ルに関するものであり、またビタミンＥパルミトレイン
酸エステルの製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a novel vitamin E palmitoleate ester, and also relates to a method for producing vitamin E palmitoleate ester.
（従来の技術）
パルミトレイン酸のエステルは、人皮中に含まれており
、特に乳幼児期および青年期などの若い世代の皮脂に多
く含まれており、皮脂の活性化に関係があるとされてい
る。また、特開昭５９−１７２４１１号公報によれば、
パルミトレイン酸は養毛剤の有効成分とされ、特開昭５
９−１７５４２５号公報によれば、パルミトレイン酸は
血管を補強する作用があるとされている。このように１
パルミトレイン酸は、最近、人体に有益な作用をするこ
とが発見され、Ｋわかに注目されるに至った。(Prior art) Palmitoleic acid ester is contained in human skin, and is particularly abundant in the sebum of young people such as infants and adolescents, and is believed to be related to the activation of sebum. There is. Also, according to Japanese Patent Application Laid-open No. 59-172411,
Palmitoleic acid is considered to be an active ingredient in hair tonics, and was published in Japanese Patent Application Publication No. 5
According to Publication No. 9-175425, palmitoleic acid is said to have the effect of reinforcing blood vessels. Like this 1
Palmitoleic acid has recently been discovered to have beneficial effects on the human body, and has attracted a lot of attention.
パルミトレイン酸は、次のような構造式を持つ化合物で
ある。Palmitoleic acid is a compound with the following structural formula.
ＣＨ３（ＣＨ２）、 ＣＨ瓢ＣＨ（ＣＨＤ、Ｃ０ＯＨ（
式２）パルミトレイン酸は、上述のように分子内に１個
の二重結合を持った不飽和脂肪酸である。パルミトレイ
ン酸は、天然には他の脂肪酸と混在してグリセリンエス
テルとして存在し、タラ肝油、イワシ油、ニシン油、鯨
油などの海産動物の油の中に含まれている。CH3 (CH2), CH Gourd CH (CHD, C0OH(
Formula 2) Palmitoleic acid is an unsaturated fatty acid having one double bond in the molecule as described above. Palmitoleic acid naturally exists as a glycerin ester mixed with other fatty acids and is found in marine animal oils such as cod liver oil, sardine oil, herring oil, and whale oil.
他方、ビタミンＥは、いわゆるビタミン類の１つとして
、動物の活動に必要なものとされた。ビタミンＥは、化
学名をα−トフ７エロールと云い、無色ないし淡黄色の
油状物であって、次のような構造式を有するものである
。On the other hand, vitamin E, one of the so-called vitamins, was considered necessary for animal activities. Vitamin E, whose chemical name is α-toph7erol, is a colorless to pale yellow oil having the following structural formula.
ビタミンＥは、酸化されやすい特性を持ち、生体内で抗
酸化剤としての作用を持ち、脂質の過酸化を防止する役
目を果たしている。従って、ビタミンＥは、生体膜を安
定化する作用を持つと云われ、末梢血管拡張作用を有し
、動脈硬化を防ぐ作用を有し、凍傷、浸出性紅斑、しも
やけ、冷え症、不妊症等に対する良好な治療剤であると
される。Vitamin E has the property of being easily oxidized, acts as an antioxidant in the body, and plays a role in preventing lipid peroxidation. Therefore, vitamin E is said to have the effect of stabilizing biological membranes, dilating peripheral blood vessels, and preventing arteriosclerosis, and is effective against frostbite, exudative erythema, chilblains, sensitivity to cold, infertility, etc. It is said to be a good therapeutic agent.
（発明が解決しようとする問題点）
ビタミンＥとパルミトレイン酸とは、上述のように有効
なものでありながら、その反応生成物が全く知られてい
なかった。そこで、この発明は、このような文献未記載
の化合物の性質を明らかにし、これによってビタミンＥ
とパルミトレイン酸との利用に貢献しようとするもので
ある。(Problems to be Solved by the Invention) Although vitamin E and palmitoleic acid are effective as described above, their reaction products have not been known at all. Therefore, this invention clarifies the properties of such compounds that have not been described in literature, and thereby
The aim is to contribute to the utilization of palmitoleic acid and palmitoleic acid.
ｃ問題を解決するための手段）
この発明は、ビタミンＥとパルミトレイン酸とを反応さ
せた結果、そこでエステルの得られることを確認し、さ
らに得られたエステルの性質を明らかにしようとするも
のである。さらに、この発明は、ビタミンＥパルミトレ
イン酸エステルの製造方法を提供しようとするものであ
る。(Means for Solving Problem c) This invention aims to confirm that an ester is obtained as a result of the reaction between vitamin E and palmitoleic acid, and to clarify the properties of the obtained ester. be. Furthermore, the present invention seeks to provide a method for producing vitamin E palmitoleic acid ester.
この発明に係るビタミンＥパルミトレイン酸エステルは
、ビタミンＥをパルミトレイン酸と反応させて得られる
化合物であって、次の構造式を持ＣＨ３−ＣＨ
（ＣＨ２）。The vitamin E palmitoleate ester according to the present invention is a compound obtained by reacting vitamin E with palmitoleic acid, and has the following structural formula: CH3-CH (CH2).
ＣＨ３−ＣＨ（式１）
％式％）
パルミトレイン酸をビタミンＥと反応させるには、両者
を混合してもよいが、好ましいのは、まずパルミトレイ
ン酸を反応性誘導体、例えば酸無水物又は酸ハロゲニド
、とくに酸クロライドとしてのち、これをビタミンＥと
混合して、反応させる方法である。CH3-CH (Formula 1) %Formula %) To react palmitoleic acid with vitamin E, both may be mixed, but it is preferred to first convert palmitoleic acid to a reactive derivative, such as an acid anhydride or an acid halide. In particular, this method involves converting it into an acid chloride, mixing it with vitamin E, and reacting it.
（実 施 例）
製造方法の一例を示すと次のとおりである。まず、パル
ミトレイン酸２０ｙと塩化チオニル２５２とを冷却管つ
き三角フラスコに入れ、２時間還流させながら反応させ
て、パルミトレイン酸をパルミトレイン酸クロライドと
した。その後これを冷却し、次いでエバポレーターで余
剰の塩化チオニルを溜去した。こうして得られたパルミ
トレイン酸クロライドをベンゼン６０ｍｅに溶解し、冷
却管つき三角フラスコに入れた。さらに、ピリジンＩＦ
Ｍ’を加え、これにビタミンＥ３０ｙをベンゼン５０ｍ
ｅに溶解した溶液を加え、２時間還流させながら反応さ
せた。その後これを冷却し、これを水に投入し、ベンゼ
ン層を分離した。ベンゼン層をＩＮ塩酸で洗浄し、次い
でＩＮ炭酸水素す） ＩＪウムで洗浄し、無水硫酸ナト
リウムで脱水した。(Example) An example of the manufacturing method is as follows. First, palmitoleic acid 20y and thionyl chloride 252 were placed in an Erlenmeyer flask equipped with a cooling tube and reacted under reflux for 2 hours to convert palmitoleic acid to palmitoleic acid chloride. Thereafter, it was cooled, and excess thionyl chloride was distilled off using an evaporator. The palmitoleic acid chloride thus obtained was dissolved in 60 me of benzene and placed in an Erlenmeyer flask equipped with a cooling tube. Furthermore, pyridine IF
Add M' and add 30y of vitamin E to this and 50m of benzene.
A solution dissolved in E was added to the mixture, and the mixture was allowed to react under reflux for 2 hours. Thereafter, it was cooled, poured into water, and the benzene layer was separated. The benzene layer was washed with IN hydrochloric acid, then IN hydrogen carbonate, and dried over anhydrous sodium sulfate.
その後エバポレーターでベンゼンを溜去シ、ビタミンＥ
パルミトレイン酸エステルの粗製品を得た。After that, the benzene was distilled off using an evaporator, and the vitamin E
A crude product of palmitoleic acid ester was obtained.
ベンゼンを溶出液としてこの粗製品をシリカゲルクロマ
トグラフィーにより、ビタミンＥパルミトレイン酸エス
テルの精製品を得た。This crude product was subjected to silica gel chromatography using benzene as an eluent to obtain a purified product of vitamin E palmitoleate.
こうして得られたビタミンＥパルミトレイン酸エステル
は、文献未記載の化合物であって、次のような性質を示
す。The vitamin E palmitoleate ester thus obtained is a compound that has not been described in any literature and exhibits the following properties.
化合物の状態 淡黄色の液体 元素分析’ Ｃ４５Ｈ，、ｏ。Compound state: Pale yellow liquid Elemental analysis' C45H,, o.
計算値Ｃ：８ＬＯＯ％ Ｈ：ＩＬ８１％実験値Ｃ：８
１．１０％ Ｈ：ＩＬ６７％比旋光度：〔α）２Ｑ
ｏ、。Calculated value C: 8LOO% H: IL81% Experimental value C: 8
1.10% H:IL67% Specific rotation: [α)2Q
o.
紫外線吸収スペクトル（クロロホルムｍｗ＞ ：吸収
極大 ２８７、 ２４４ ｎｍ （第１図参照）赤
外線吸収スペクトル：
吸収極大 ２９１０ 、１７５５ ．１４６０ｃｍ−’
（第２図参照）
溶剤に対する溶解性
水 不溶
メタノール 不 溶
イソプロパツール 可 溶
アセトン 可 溶
ヘキサン 可 溶
ベンゼン 可 溶
トルエン 可 溶
ジエチルエーテル 可 溶
酢酸エチル 可 溶
ＮＭＲδ値 ｐｐｍ（Ｈ）
０．８８ （１５Ｈ，ｄ、 Ｊ＝５．８Ｈ２）１．
２２〜１．４０ （４４Ｈ，ｍ）１．９７〜２．０９
（１３Ｈ，ＳＸ３． ｍ）２．６０ （
！４Ｈ，ｔ、 Ｊ＝６Ｈ２）５．３７ （２
Ｈ，ｔ、 Ｊ−４Ｈｚ）（第３図参照）
（発明の効果）
ビタミンＥパルミトレイン酸エステルは、ビタミンＥの
抗動脈硬化作用と、パルミトレイン酸の皮膚の活性化と
血管の補強作用とを併ゎせ有するものと考えられ、血管
障害に対する治療剤として有効であると考えられる。Ultraviolet absorption spectrum (Chloroform mw>: absorption maximum 287, 244 nm (see Figure 1)) Infrared absorption spectrum: absorption maximum 2910, 1755.1460 cm-'
(See Figure 2) Solubility in solvents Water Insoluble methanol Insoluble isopropanol Soluble Acetone Soluble Hexane Soluble Benzene Soluble Toluene Soluble Diethyl ether Soluble Ethyl acetate Soluble NMR δ value ppm (H) 0.88 ( 15H, d, J=5.8H2)1.
22-1.40 (44H, m) 1.97-2.09
(13H, SX3.m) 2.60 (
! 4H, t, J=6H2)5.37 (2
H, t, J-4Hz) (see Figure 3) (Effects of the invention) Vitamin E palmitoleate combines the anti-arteriosclerotic effect of vitamin E and the skin activation and blood vessel reinforcing effects of palmitoleic acid. It is believed that the drug is effective as a therapeutic agent for vascular disorders.
第１図は、この発明に係るビタミンＥパルミトレイン酸
の紫外線吸収スペクトルを示す。第２図は、この発明て
係るビタミンＥパルミトレイン酸の赤外線吸収スペクト
ルを示す。！８ＩＮは、この発明に係るビタミンＥパル
ミトレイン酸＋７）ＮＭＲスペクトルを示す。FIG. 1 shows the ultraviolet absorption spectrum of vitamin E palmitoleic acid according to the present invention. FIG. 2 shows an infrared absorption spectrum of vitamin E palmitoleic acid according to the present invention. ! 8IN shows the vitamin E palmitoleic acid+7) NMR spectrum according to this invention.
Claims (1)
を反応させることを特徴とする、ビタミンＥパルミトレ
イン酸エステルの製造方法。[Claims] 1. Parsitoleic acid ester represented by the chemical formula ▲ Numerical formula, chemical formula, table, etc. ▼ (Formula 1). 2. A method for producing vitamin E palmitoleate, which comprises reacting vitamin E with palmitole or a reactive derivative thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32197987A JPH01163176A (en) | 1987-12-18 | 1987-12-18 | Vitamin e palmitoleic acid ester and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32197987A JPH01163176A (en) | 1987-12-18 | 1987-12-18 | Vitamin e palmitoleic acid ester and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01163176A true JPH01163176A (en) | 1989-06-27 |
Family
ID=18138562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32197987A Pending JPH01163176A (en) | 1987-12-18 | 1987-12-18 | Vitamin e palmitoleic acid ester and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01163176A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2825088A1 (en) * | 2001-05-25 | 2002-11-29 | Derma Dev | NOVEL TOCOPHEROL ESTERS, PROCESSES FOR OBTAINING SAME AND USES THEREOF |
| KR100482671B1 (en) * | 2002-02-05 | 2005-04-13 | 주식회사 태평양 | The derivatives of dilinoleic acid and a method for preparation thereof and complex containing it |
| JP2008016494A (en) * | 2006-07-03 | 2008-01-24 | Seiko Epson Corp | Method of manufacturing semiconductor device |
-
1987
- 1987-12-18 JP JP32197987A patent/JPH01163176A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2825088A1 (en) * | 2001-05-25 | 2002-11-29 | Derma Dev | NOVEL TOCOPHEROL ESTERS, PROCESSES FOR OBTAINING SAME AND USES THEREOF |
| KR100482671B1 (en) * | 2002-02-05 | 2005-04-13 | 주식회사 태평양 | The derivatives of dilinoleic acid and a method for preparation thereof and complex containing it |
| JP2008016494A (en) * | 2006-07-03 | 2008-01-24 | Seiko Epson Corp | Method of manufacturing semiconductor device |
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