JPS63317091A - Production of omega-hydroxy-trans-alpha,beta-unsaturated fatty acid - Google Patents
Production of omega-hydroxy-trans-alpha,beta-unsaturated fatty acidInfo
- Publication number
- JPS63317091A JPS63317091A JP62152037A JP15203787A JPS63317091A JP S63317091 A JPS63317091 A JP S63317091A JP 62152037 A JP62152037 A JP 62152037A JP 15203787 A JP15203787 A JP 15203787A JP S63317091 A JPS63317091 A JP S63317091A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- coa
- omega
- acyl
- fatty acid
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 102000004539 Acyl-CoA Oxidase Human genes 0.000 claims abstract description 10
- 108020001558 Acyl-CoA oxidase Proteins 0.000 claims abstract description 10
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 4
- 239000000194 fatty acid Substances 0.000 abstract description 4
- 229930195729 fatty acid Natural products 0.000 abstract description 4
- 150000004665 fatty acids Chemical class 0.000 abstract description 4
- 102000016938 Catalase Human genes 0.000 abstract description 3
- 108010053835 Catalase Proteins 0.000 abstract description 3
- 238000006911 enzymatic reaction Methods 0.000 abstract description 3
- 241000222120 Candida <Saccharomycetales> Species 0.000 abstract description 2
- 239000003638 chemical reducing agent Substances 0.000 abstract description 2
- 238000004587 chromatography analysis Methods 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000004615 ingredient Substances 0.000 abstract 2
- 241000894006 Bacteria Species 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000001256 tonic effect Effects 0.000 abstract 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004050 enoyl group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000003822 preparative gas chromatography Methods 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QHBZHVUGQROELI-SOFGYWHQSA-N (E)-10-hydroxydec-2-enoic acid Chemical compound OCCCCCCC\C=C\C(O)=O QHBZHVUGQROELI-SOFGYWHQSA-N 0.000 description 1
- 241000186063 Arthrobacter Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- QHBZHVUGQROELI-UHFFFAOYSA-N Royal Jelly acid Natural products OCCCCCCCC=CC(O)=O QHBZHVUGQROELI-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000003779 hair growth Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940109850 royal jelly Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940081330 tena Drugs 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
この発明は栄養剤、育毛剤、化粧品（美白剤）の素材と
して期待されているω−ハイドロキシ−トランス−α、
β−不飽和脂肪酸の製造法に関する。Detailed Description of the Invention (Field of Industrial Application) This invention is directed to ω-hydroxy-trans-α, which is expected to be used as a material for nutritional supplements, hair growth agents, and cosmetics (whitening agents).
This invention relates to a method for producing β-unsaturated fatty acids.
（従来の技術）
近年、不飽和高級脂肪酸類の生体内での代謝および生理
作用に関する研究が進展するにつれ、その重要性が認識
されてき九。従来、ω−ハイドロキシ−トランス−α、
β−不飽和脂肪酸たとえばローヤルゼリー中Ｋｔまれて
いる１０−ハイドロキシ−トランス−２−デセンｆｆ１
ｉ！ｌ：ローヤルゼリー酸）の製造は有機合成的手法に
より試みられている（文献：特開昭４８−８７２３号公
報、特開昭４８−１００２１号公報および特開昭５４−
８８２１６号公報）。(Prior Art) In recent years, as research on the in vivo metabolism and physiological effects of unsaturated higher fatty acids has progressed, their importance has been recognized9. Conventionally, ω-hydroxy-trans-α,
β-unsaturated fatty acids such as 10-hydroxy-trans-2-deceneff1, which is present in royal jelly
i! 1: royal jelly acid) has been attempted to be produced by organic synthetic methods (References: JP-A-48-8723, JP-A-48-10021, and JP-A-Sho 54-
88216).
（発明が解決すべき問題点）
しかしながら、これら有機合成的手法では製造工程が長
くて複雑であり、また、収率が低いという問題があった
。本発明は酵素反応を用いて非常に簡便に１高収率で、
かつ高純度でω−ハイドロキシ−トランス−α、β−不
飽和脂肪酸を製造する方法を提供することを目的とする
。(Problems to be Solved by the Invention) However, these organic synthesis methods have problems in that the manufacturing process is long and complicated, and the yield is low. The present invention uses an enzymatic reaction to very easily achieve 1 high yield.
Another object of the present invention is to provide a method for producing ω-hydroxy-trans-α,β-unsaturated fatty acids with high purity.
（問題点を解決するための手段）
本発明者らはω−ハイドロキシ−トランス−α、β−不
飽和脂肪酸の酵素的合成法の検討を行なった。従来、飽
和脂肪酸類のＣＯＡがアシル−ＣＯＡオキシダーゼの作
用を受けてエノイルＣＯＡに変化すること（式１の反応
）は良く知られている。(Means for Solving the Problems) The present inventors investigated a method for enzymatically synthesizing ω-hydroxy-trans-α,β-unsaturated fatty acids. It has been well known that COA of saturated fatty acids changes into enoyl COA under the action of acyl-COA oxidase (reaction of Formula 1).
式Ｉ ＣＨ３（ＣＨ２）Ｈ−ＣＣＩＣｏＡ（アシル
−ＣＯＡ ）
ＣＨ３（ＣＨ２）Ｑ−２・ＣＨ−ＣＨ−Ｃｏ−ＣｏＡ（
エノイルＣＯＡ ）
（ｎ−６〜１８）
ところが、飽和脂肪酸類のＣｏＡにのみ活性を示すと考
えられていたアシル−ＣＯＡオキシダーゼが意外にもω
−ハイドロキシ−アシル−ＣＯＡに対しても活性を示し
、効率的にα、β位にトランス体の二重結合を導入でき
ること（式２の反応）金兄い出し、本発明を完成させる
に到った。Formula I CH3(CH2)H-CCICoA(acyl-COA) CH3(CH2)Q-2・CH-CH-Co-CoA(
(enoyl COA) (n-6 to 18) However, acyl-COA oxidase, which was thought to be active only on CoA of saturated fatty acids, surprisingly
-It also shows activity against hydroxy-acyl-COA and can efficiently introduce trans double bonds into the α and β positions (reaction of formula 2). Ta.
式２ ＨＯＣＨ２（ＣＨ２）Ｈ拳ＣＯ＠Ｃ０Ａ（ω
−ハイドロキシ・アシル−ＣＯＡ）ＨＯＣＨ２（ＣＨ２
）ｎ−２・ＣＨ−ＣＨＣＯ・Ｃ０Ａ（ω−ハイドロキシ
エノイル ＣｏＡ）ＨＯＣＨ２（ＣＨ２）ｎ−、−ＣＭ
−ＣＨ−ＣＯＯＨ（ω−ハイドロキシ−トランス−α、
β−不飽和脂肪ｒ１り（ｎ−６〜１８）
すなわち、本発明はω−ハイドロキシ−アシル−ＣＯＡ
にアシル−ＣＯＡオキシダーゼを作用させ、得られたω
−ハイドロキシ−エノイル−ＣｏＡｅ２７０水分解する
ことｔ−特徴とするω−ハイドロキシ−トランス−α、
β−不飽和脂肪酸の製造法である。Formula 2 HOCH2(CH2)H fist CO@C0A(ω
-Hydroxy acyl-COA)HOCH2(CH2
)n-2・CH-CHCO・C0A (ω-hydroxyenoyl CoA) HOCH2(CH2)n-, -CM
-CH-COOH (ω-hydroxy-trans-α,
β-unsaturated fat r1 (n-6 to 18) That is, the present invention uses ω-hydroxy-acyl-COA
was treated with acyl-COA oxidase, and the obtained ω
- hydroxy-enoyl-CoAe270 water-splitting t-characterized by ω-hydroxy-trans-α,
This is a method for producing β-unsaturated fatty acids.
本発明方法において、ω−ハイドロキシ−アシル−ＣＯ
Ａは脂肪酸の炭素数が０８〜Ｃ２０の範囲が好ましく％
Ｃ１０〜Ｃ１６はとくに好ましい。炭素数がＣ８未満ま
たはＣｇＱを越えるとアシル−ＣＯＡオキシダーゼが作
用し難い。In the method of the present invention, ω-hydroxy-acyl-CO
A preferably has a fatty acid carbon number in the range of 08 to C20%
C10 to C16 are particularly preferred. When the number of carbon atoms is less than C8 or more than CgQ, acyl-COA oxidase is difficult to act.
アシル−ＣＯＡオキシダーゼは市販のものでもよく、ま
た、この酵素を産生ずることが知られている微生物、と
くに炭化水素資化性のカンデイダ属（Ｃａｎｄｉｄａ
） 、アリスロバクター属（Ａｒｔｈｒｏｂａｃｔｅｒ
）寺から単離・精製したものを用いてもよい。単離・精
製の方法はたとえばバイオケミカル・アンド、バイオフ
ィシカル・リサーチ・コミュニケーションズ（Ｂｉｏｃ
ｈｅｍｉｃａｌ ａｎｄ Ｂｉｏｐｈｙｓｉｃａｌ Ｒ
ｅ５ｅａｒｃｈ用いてもよいが、担体に固定したものあ
るいはそれ金含む菌体を用いてもよい。Acyl-COA oxidase may be commercially available, or microorganisms known to produce this enzyme, particularly those of the hydrocarbon-assimilating genus Candida.
), Arthrobacter spp.
) You may use those isolated and purified from temples. Isolation and purification methods are available from Biochemical & Biophysical Research Communications (Bioc).
chemical and biophysical
Although e5earch may be used, cells immobilized on a carrier or cells containing gold may also be used.
ω−ハイドロキシ−アシル−ＣＯＡにアシル−ＣｏＡオ
キシダーゼを作用させるときの温度は１０′Ｃ〜６５°
Ｃが好ましく、２０℃〜４０℃がとくに好ましい。この
ときの−は５〜１０が好ましく、７〜９がとくに好まし
い。ω−ハイドロキシ−アシル−ＣＯＡにアシル−ＣＯ
Ａオキシダーゼを作用させると過酸化水素が発生し、過
酸化水素がこの酵素反応を阻害したり酵素を不活化する
ことがある。The temperature when acyl-CoA oxidase acts on ω-hydroxy-acyl-COA is 10'C to 65°.
C is preferred, and 20°C to 40°C is particularly preferred. In this case, - is preferably 5 to 10, particularly preferably 7 to 9. Acyl-CO to ω-hydroxy-acyl-COA
When A oxidase is activated, hydrogen peroxide is generated, and hydrogen peroxide may inhibit this enzymatic reaction or inactivate the enzyme.
そのため、反応系にカメラーゼを共存させて過酸化水素
を分解させることが好ましい。また、カタラーゼによる
過酸化水素の分解の結果生じた酸素も過酸化水素と同様
に有害であるので、反応系に還元剤を共存させるか、ま
たは反応を減圧下で行なうことが好ましい。Therefore, it is preferable to allow camerase to coexist in the reaction system to decompose hydrogen peroxide. Further, since oxygen produced as a result of decomposition of hydrogen peroxide by catalase is also harmful like hydrogen peroxide, it is preferable to have a reducing agent coexist in the reaction system or to carry out the reaction under reduced pressure.
つぎに、生成したω−ハイドロキシ−エノイル−ＣＯＡ
を含む反応液に加水分解剤ｔ−ｍえてω−）１イドロキ
シーエノイルー〇ＯＡ ’ｉ加水分解する。加水分解剤
は塩酸、水酸化カリウムなど強酸または強アルカリが好
ましい。Next, the generated ω-hydroxy-enoyl-COA
A hydrolyzing agent t-m is added to the reaction solution containing ω-)1 hydroxyenoyl OA'i and hydrolyzed. The hydrolyzing agent is preferably a strong acid or strong alkali such as hydrochloric acid or potassium hydroxide.
用水分解後、エーテル、酢酸エチルなどの溶媒でω−ハ
イドロキシ−トランス−α、β−不飽和脂肪ｆＩｌ′を
抽出する。抽出液を蒸発濃縮し、残渣全シリカｒルクロ
マトグラフイーまたは分取液体クロマトグラフィーで精
製すれば高純度のω−ハづドロキシ−トランス−α、β
−不飽和脂肪酸が得られる。以下に本発明を実施例で具
体的に説明するが、これらに限定されるものではない。After water decomposition, the ω-hydroxy-trans-α,β-unsaturated fat fl' is extracted with a solvent such as ether or ethyl acetate. The extract is concentrated by evaporation, and the residue is purified by total silica chromatography or preparative liquid chromatography to obtain highly pure ω-hydroxy-trans-α, β.
- Unsaturated fatty acids are obtained. EXAMPLES The present invention will be specifically explained below using Examples, but is not limited thereto.
（実施例）
ＦＪ（７，５の０．０５ Ｍ−リン酸緩衝液１０１１Ｌ
ｌにアシル−ＣＯＡオキシダーゼ（東洋紡績株式会社製
）３単位とカタラーゼ（和光純薬株式会社製）３単位を
浴解し、表に示すω−ハイドロキシ−アシル−ＣｏＡ
ｆ １ｍモル添加し友。アスピレータ−減圧下、攪拌し
ながら温度６０℃で２０時間保ちω−ノ１イドロキシー
エノイルーＣ０Ａｔ−生成させた。(Example) FJ (7,5 0.05 M-phosphate buffer 1011 L
3 units of acyl-COA oxidase (manufactured by Toyobo Co., Ltd.) and 3 units of catalase (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved in l, and the ω-hydroxy-acyl-CoA shown in the table was obtained.
Add 1 mmol of f. The mixture was kept at a temperature of 60° C. for 20 hours with stirring under reduced pressure using an aspirator to produce ω-no-1 hydroxyenoyl-COAt-.
反応液に１０％水酸化カリウム水溶液’ｔ２＋ＩＬｌ添
加し、温度７０℃で１５分間放置することによって、前
記ω−ハイドロキシ−エノイル−ＣＯＡ ｋ ２Ｘ１水
分解した。反応液に塩酸を那えてＰＨ全５に調製してカ
ラ５ ｍ／のエチルエーテルによる抽出を４回行ない、
エチルエーテル層全無水硫酸す） ＩＪウムで脱水した
のち、エチルエーテルを減圧で蒸発して除去した。The ω-hydroxy-enoyl-COA k 2X1 water was decomposed by adding 10% aqueous potassium hydroxide solution 't2+ILl to the reaction solution and leaving it for 15 minutes at a temperature of 70°C. Add hydrochloric acid to the reaction solution to adjust the pH to 5, and extract 4 times with 5 m/ml of ethyl ether.
After dehydrating the entire ethyl ether layer with anhydrous sulfuric acid (IJ), the ethyl ether was removed by evaporation under reduced pressure.
残渣を分取ガスクロマトグラフィーで処理し、ω−ハイ
ドロキシ−トランス−α、β−不飽和脂肪酸を単離した
。なお、分取ガスクロマトグラフィーは担体「Ｔｅｎａ
ｘ ＧＣ−ＤＭＤ８ Ｊ （粒度６０〜８０メツシユ）
に０Ｖ−１７ｔ−５％コーティングした充てん剤を用い
、ヘリウムをキャリアガスとして、カラム温度２４０℃
で行なった。The residue was treated with preparative gas chromatography to isolate ω-hydroxy-trans-α,β-unsaturated fatty acids. In addition, preparative gas chromatography uses the carrier “Tena
x GC-DMD8 J (particle size 60-80 mesh)
Using a packing material coated with 0V-17t-5%, the column temperature was 240℃ using helium as a carrier gas.
I did it.
単離された物質は懇分析（溶媒：四塩化炭素）の結果、
表に示すとおり、ω−ハイドロキシ−トランス−α、β
−不飽和脂肪酸に特有の化学シフトが現われた。また、
前記残渣中のω−７１イドロキシートランスーα、β−
不飽和脂肪酸をガスクロマトグラフィーで定量し、収率
を求めた。収率は表に示すとおり高収率であった。The isolated substance was analyzed (solvent: carbon tetrachloride) as a result of
As shown in the table, ω-hydroxy-trans-α, β
-A chemical shift specific to unsaturated fatty acids appeared. Also,
ω-71 hydroxytrans-α, β- in the residue
Unsaturated fatty acids were quantified by gas chromatography to determine the yield. The yield was high as shown in the table.
（発明の効果）
本発明の製造法によればω−ハイドロキシ−トランス−
α、β−不飽和脂肪酸を容易に、高収率でかつ高純度で
製造することができる。(Effect of the invention) According to the production method of the present invention, ω-hydroxy-trans-
α,β-unsaturated fatty acids can be easily produced with high yield and high purity.
Claims (1)
キシダーゼを作用させ、得られたω−ハイドロキシ−エ
ノイル−ＣＯＡを加水分解することを特徴とするω−ハ
イドロキシ−トランス−α，β−不飽和脂肪酸の製造法
。Production of ω-hydroxy-trans-α,β-unsaturated fatty acids, characterized by allowing acyl-COA oxidase to act on ω-hydroxy-acyl-COA and hydrolyzing the obtained ω-hydroxy-enoyl-COA. Law.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62152037A JPS63317091A (en) | 1987-06-18 | 1987-06-18 | Production of omega-hydroxy-trans-alpha,beta-unsaturated fatty acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62152037A JPS63317091A (en) | 1987-06-18 | 1987-06-18 | Production of omega-hydroxy-trans-alpha,beta-unsaturated fatty acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63317091A true JPS63317091A (en) | 1988-12-26 |
Family
ID=15531676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62152037A Pending JPS63317091A (en) | 1987-06-18 | 1987-06-18 | Production of omega-hydroxy-trans-alpha,beta-unsaturated fatty acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63317091A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007045741A2 (en) * | 2005-10-21 | 2007-04-26 | Pierre Fabre Dermo Cosmetique | Novel method for preparing unsaturated fatty hydroxyacids |
| JP2009512664A (en) * | 2005-10-21 | 2009-03-26 | ピエール、ファブレ、デルモ‐コスメティーク | Novel unsaturated hydroxy fatty acid derivatives and their skin cosmetic use |
-
1987
- 1987-06-18 JP JP62152037A patent/JPS63317091A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007045741A2 (en) * | 2005-10-21 | 2007-04-26 | Pierre Fabre Dermo Cosmetique | Novel method for preparing unsaturated fatty hydroxyacids |
| WO2007045741A3 (en) * | 2005-10-21 | 2007-08-02 | Diverchim | Novel method for preparing unsaturated fatty hydroxyacids |
| JP2009512665A (en) * | 2005-10-21 | 2009-03-26 | ピエール、ファブレ、デルモ‐コスメティーク | Novel process for producing unsaturated aliphatic hydroxy acids |
| JP2009512664A (en) * | 2005-10-21 | 2009-03-26 | ピエール、ファブレ、デルモ‐コスメティーク | Novel unsaturated hydroxy fatty acid derivatives and their skin cosmetic use |
| US7928254B2 (en) | 2005-10-21 | 2011-04-19 | Pierre Fabre Dermo-Cosmetique | Method for preparing unsaturated fatty hydroxyacids |
| US8158811B2 (en) | 2005-10-21 | 2012-04-17 | Pierre Fabre Dermo-Cosmetique | Unsaturated fatty hydroxy acid derivatives and the dermocosmetologic use thereof |
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