JPH01157931A - 2-n-dodecyl-3-hydroxy-n-hexadecanoic acid and its ester - Google Patents
2-n-dodecyl-3-hydroxy-n-hexadecanoic acid and its esterInfo
- Publication number
- JPH01157931A JPH01157931A JP31439887A JP31439887A JPH01157931A JP H01157931 A JPH01157931 A JP H01157931A JP 31439887 A JP31439887 A JP 31439887A JP 31439887 A JP31439887 A JP 31439887A JP H01157931 A JPH01157931 A JP H01157931A
- Authority
- JP
- Japan
- Prior art keywords
- dodecyl
- hydroxy
- ester
- hexadecanoic acid
- formula
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔技術分野〕
本発明は免疫賦活剤等として有用な２−ｎ−ドデシル−
３−ヒドロキシ−ｎ−ヘキサデカン酸及びそのエステル
に関するものである。Detailed Description of the Invention [Technical Field] The present invention provides 2-n-dodecyl-
It relates to 3-hydroxy-n-hexadecanoic acid and its esters.
従来、ある種のバクテリアの生体細胞には、２−アルキ
ル−３−ヒドロキシ脂肪酸誘導体が存在し、各種細胞の
活性化に重要な働きをしていることが知られている。It has been known that 2-alkyl-3-hydroxy fatty acid derivatives exist in living cells of certain bacteria and play an important role in activating various cells.
しかし、これら天然由来の２−アルキル−３−ヒドロキ
シ脂肪酸誘導体は極く微量成分である上に、炭素鎖長の
異る多くの同族体の混合物であり、しかも毒性がある等
の問題点が指摘されている。However, these naturally derived 2-alkyl-3-hydroxy fatty acid derivatives contain extremely small amounts of ingredients, are mixtures of many homologs with different carbon chain lengths, and have problems such as toxicity. has been done.
本発明は、毒性が弱くかつ強力な細胞賦活作用を有する
新規な２−アルキル−３−ヒドロキシ脂肪酸及びその誘
導体を提供することを目的とする。An object of the present invention is to provide a novel 2-alkyl-3-hydroxy fatty acid and its derivatives that have low toxicity and a strong cell activating effect.
本発明者らは、前記目的を達成するために、炭素鎖長が
一定な２−アルキル−３−ヒドロキシ脂肪酸及びその誘
導体を化学的に合成すべく鋭意研究を続けた結果、２−
ｎ−ドデシル−３−ヒドロキシ−ｎ−ヘキサデカン酸及
びそのエステルを合成することに成功し１本発明を完成
するに到った。In order to achieve the above object, the present inventors continued intensive research to chemically synthesize 2-alkyl-3-hydroxy fatty acids and derivatives thereof having a constant carbon chain length.
The present invention was completed by successfully synthesizing n-dodecyl-3-hydroxy-n-hexadecanoic acid and its ester.
即ち、本発明によれば、ｎ−ドデシル−３−ヒドロキシ
−ｎ−ヘキサデカン酸又はそのエステルが提供される。That is, according to the present invention, n-dodecyl-3-hydroxy-n-hexadecanoic acid or its ester is provided.
本発明の化合物は、次の式で表わされる。The compound of the present invention is represented by the following formula.
ｎ−ＣＬ２Ｈ２５
前記式中、−ＯＲはヒドロキシル基（−ＯＨ）又はアル
コール残基である。アルコール残基としては、例えば、
低級アルコールや、グリコール、糖類等の残基が挙げら
れる。n-CL2H25 In the above formula, -OR is a hydroxyl group (-OH) or an alcohol residue. Examples of alcohol residues include:
Examples include residues of lower alcohols, glycols, sugars, and the like.
本発明の化合物を合成するには、テトラデカン酸エステ
ルをキシレン中で水素化ナトリウムを加えて加熱縮合反
応させることによって得られる一般式
（式中、ＯＲはアルコール残基を示す）で表わされる２
−ｎ−ドデシル−３−オキソ−ｎ−ヘキサデカン酸エス
テルのケトン基を還元して、−船蔵％式％
（式中、−ＯＲは前記と同じ）
で表わされる２−ｎ−ドデシル−３−ヒドロキシ−ｎ−
ヘキサデカン酸エステルに変える。To synthesize the compound of the present invention, tetradecanoic acid ester is heated and condensed in xylene with the addition of sodium hydride.
The ketone group of -n-dodecyl-3-oxo-n-hexadecanoic acid ester is reduced to give 2-n-dodecyl-3- Hydroxy-n-
Change to hexadecanoic acid ester.
次いで、このものをアルカリ処理してエステル基を加水
分解することにより、次式で表わされる２−ｎ−ドデシ
ル−３−ヒドロキシ−ｎ−ヘキサデカン酸を得る。Next, this product is treated with an alkali to hydrolyze the ester groups to obtain 2-n-dodecyl-3-hydroxy-n-hexadecanoic acid represented by the following formula.
前記のようにして得られた２−ｎ−ドデシル−３−ヒド
ロキシ−ｎ−ヘキサデカン酸及びそのエステルは。2-n-dodecyl-3-hydroxy-n-hexadecanoic acid and its ester obtained as described above.
２位ｎ−ドデシル基（ｎ−Ｃ１，Ｈ□）と３位ヒドロキ
シル基（−ＯＲ）とが立体化学的に互いにｓｙｎ配置し
たものと。The n-dodecyl group (n-C1, H□) at the 2nd position and the hydroxyl group (-OR) at the 3rd position are stereochemically arranged in syn to each other.
ａｎｔｉ配置したものの混合物からなるものである。It consists of a mixture of anti-arranged substances.
このｓｙｎ配置化合物とａｎｔｉ配置化合物とは、薄層
クロマトグラフィー等のｓｙｎ−ａｎｔｉ異性体分離技
術により、それぞれの成分に分離することができる。The syn configuration compound and the anti configuration compound can be separated into their respective components by a syn-anti isomer separation technique such as thin layer chromatography.
〔実施例〕 ゛ 次に本発明を実施例によりさらに詳細に説明する。[Example] Next, the present invention will be explained in more detail with reference to Examples.
実施例１
水素化ホウ素ナトリウム０．６２ｇを含むエタノール溶
液６５−１に２−ｎ−ドデシル−３−オキソ−ｎ−ヘキ
サデカン酸メチル４．０２ｇを添加して室温で攪拌した
。Example 1 To ethanol solution 65-1 containing 0.62 g of sodium borohydride, 4.02 g of methyl 2-n-dodecyl-3-oxo-n-hexadecanoate was added and stirred at room temperature.
反応混合物中のエステルの固体は次第に消え白濁溶液が
得られた。３時間後反応液を氷−塩酸水溶液中にあけて
未反応の水素化物を分解し、水を加えて室温で攪拌した
。１時間後抽出した白色固体を吸引濾過して集め゛よく
水洗して乾燥すると３．９８ｇの粗生成物が得られた。The solid ester in the reaction mixture gradually disappeared to give a cloudy white solution. After 3 hours, the reaction solution was poured into an ice-hydrochloric acid aqueous solution to decompose unreacted hydride, water was added, and the mixture was stirred at room temperature. After 1 hour, the extracted white solid was collected by suction filtration, thoroughly washed with water, and dried to obtain 3.98 g of crude product.
この生成物０．２７ｇをシリカゲル分取薄層クロマトグ
ラフィー（展開液；ベンゼン）により精製すると、純粋
なｓｙｎ−２−ｎ−ドデシル−３−ヒドロキシ−ｎ−ヘ
キサデカン酸メチルの無色結晶（ｍｐ６３．５〜６４℃
）とａｎｔｉ−２−ｎ−ドデシル−３−ヒドロキシ−ｎ
−ヘキサデカン酸メチルの無色結晶（ｍｐ４８〜４８．
５℃）が得られた。0.27 g of this product was purified by silica gel preparative thin layer chromatography (developing solution: benzene), resulting in colorless crystals of pure methyl syn-2-n-dodecyl-3-hydroxy-n-hexadecanoate (mp 63.5). ~64℃
) and anti-2-n-dodecyl-3-hydroxy-n
- Colorless crystals of methyl hexadecanoate (mp48-48.
5°C) was obtained.
［ｓｙｎ一体の元素分析結果〕
測定値＝ Ｃニア、６．３３ Ｈ； １２．９５計
算値 Ｃニア６．５９ Ｈ： １２．８６（ＣｚｓＨ
ｉｓ０３）
［ａｎｔｉ一体の元素分析結果］
測定値 Ｃニア６．６８ Ｈ： １２．７０計算値
Ｃニア６．５９ Ｈ： １２．８６（Ｃ，、Ｈ□０３
）
〔効 果〕
本発明による化合物は新規物質であり、細胞賦活作用を
有する。また、本発明の化合物は、二鎖脂肪族基を有す
ることから、親油性、親水性のバランスした生分解性の
界面活性剤原料として用いることもできる。[Results of elemental analysis of syn] Measured value = C near, 6.33 H; 12.95 Calculated value C near 6.59 H: 12.86 (CzsH
is03) [Anti-integrated elemental analysis result] Measured value C near 6.68 H: 12.70 calculated value
C near 6.59 H: 12.86 (C,, H□03
) [Effects] The compound according to the present invention is a new substance and has a cell activating effect. Moreover, since the compound of the present invention has a two-chain aliphatic group, it can also be used as a raw material for a biodegradable surfactant with balanced lipophilicity and hydrophilicity.
Claims (3)
ある。）で表わされる２−ｎ−ドデシル−３−ヒドロキ
シ−ｎ−ヘキサデカン酸又はそのエステル。(1) 2-n-dodecyl-3-hydroxy-n-hexadecanoic acid or That ester.
サデカン酸又はそのエステルがｓｙｎ−異性体である特
許請求の範囲第１項の化合物。(2) The compound according to claim 1, wherein the 2-n-dodecyl-3-hydroxy-n-hexadecanoic acid or its ester is a syn-isomer.
サデカン酸又はそのエステルがａｎｔｉ−異性体である
特許請求の範囲第１項の化合物。(3) The compound according to claim 1, wherein the 2-n-dodecyl-3-hydroxy-n-hexadecanoic acid or ester thereof is an anti-isomer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31439887A JPH01157931A (en) | 1987-12-11 | 1987-12-11 | 2-n-dodecyl-3-hydroxy-n-hexadecanoic acid and its ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31439887A JPH01157931A (en) | 1987-12-11 | 1987-12-11 | 2-n-dodecyl-3-hydroxy-n-hexadecanoic acid and its ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01157931A true JPH01157931A (en) | 1989-06-21 |
Family
ID=18052867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31439887A Pending JPH01157931A (en) | 1987-12-11 | 1987-12-11 | 2-n-dodecyl-3-hydroxy-n-hexadecanoic acid and its ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01157931A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR19990059023A (en) * | 1997-12-30 | 1999-07-26 | 안용찬 | Method for preparing 2-branched chain 3-hydroxyfatty acid and salts thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3334210A1 (en) * | 1983-09-22 | 1985-04-04 | Henkel KGaA, 4000 Düsseldorf | Ethoxylation products of hydroxycarboxamides and their use as low-foam surfactants |
-
1987
- 1987-12-11 JP JP31439887A patent/JPH01157931A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3334210A1 (en) * | 1983-09-22 | 1985-04-04 | Henkel KGaA, 4000 Düsseldorf | Ethoxylation products of hydroxycarboxamides and their use as low-foam surfactants |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR19990059023A (en) * | 1997-12-30 | 1999-07-26 | 안용찬 | Method for preparing 2-branched chain 3-hydroxyfatty acid and salts thereof |
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