JPH0471063B2 - - Google Patents
Info
- Publication number
- JPH0471063B2 JPH0471063B2 JP58104596A JP10459683A JPH0471063B2 JP H0471063 B2 JPH0471063 B2 JP H0471063B2 JP 58104596 A JP58104596 A JP 58104596A JP 10459683 A JP10459683 A JP 10459683A JP H0471063 B2 JPH0471063 B2 JP H0471063B2
- Authority
- JP
- Japan
- Prior art keywords
- carnitine
- acid
- mandelic acid
- ion exchange
- mandelate
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明はdl−カルニチン（dl−γ−ジメチルア
ミノ−β−ハイドロキシ酪酸メチルベタイン）を
ｌ（−）およびｄ（＋）−カルニチンに分割する方
法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for splitting dl-carnitine (dl-γ-dimethylamino-β-hydroxybutyrate methylbetaine) into l(-) and d(+)-carnitine.
詳しくは、dl−カルニチンにＤ（−）−マンデル
酸を作用させてジアステレオーマ塩を形成させ、
このジアステレオーマ塩からｌ（−）−カルニチン
を分離することを特徴とするｌ（−）−カルニチン
の製造方法である。 Specifically, dl-carnitine is reacted with D(-)-mandelic acid to form a diastereomeric salt,
This is a method for producing l(-)-carnitine, which is characterized by separating l(-)-carnitine from this diastereomeric salt.
近年ｌ（−）−カルニチンの生理作用ならびに臨
床的応用に関して多くの研究が行なわれ、その結
果、消化管の内分泌の促進、蠕動運動の亢進作
用、ならびに血糖値、血中コレステロール値を低
下させるなど代謝を正常化する作用が期待されて
いる。しかしながら、ｌ（−）−カルニチンの工業
的に有利な製造方法はいまだ開発されていない。 In recent years, much research has been conducted on the physiological effects and clinical applications of l(-)-carnitine, which has shown that it promotes endocrine secretion in the gastrointestinal tract, enhances peristalsis, and lowers blood sugar and blood cholesterol levels. It is expected to have the effect of normalizing metabolism. However, an industrially advantageous method for producing l(-)-carnitine has not yet been developed.
従来、ｌ（−）−カルニチンの一般的な製造法と
してはdl−カルニチンニトリルハイドロキサイト
に分割剤としてｌ−カルフアスルホン酸または、
Ｎ−アセチル−Ｄ−グルタミン酸を作用させて得
たジアステレオーマ塩をエチルアルコール中で塩
酸処理し、それぞれ光学活性なカルニチンニトリ
ルクロリドに変換し、濃塩酸中で加水分割して製
造する方法が知られている。又、dl−カルニチン
アミドをＤ（＋）−カンフア酸で分割後光学活性な
ｌ（−）−カルニチンアミドを加水分解する製造法
が提案されている。 Conventionally, the general method for producing l(-)-carnitine is to add l-carphasulfonic acid or l-carphasulfonic acid as a resolving agent to dl-carnitine nitrile hydroxide.
A method is known in which diastereomeric salts obtained by the action of N-acetyl-D-glutamic acid are treated with hydrochloric acid in ethyl alcohol, converted into optically active carnitine nitrile chloride, and then hydrolyzed in concentrated hydrochloric acid to produce the diastereomeric salts. There is. A production method has also been proposed in which dl-carnitinamide is resolved with D(+)-camphoric acid and then optically active l(-)-carnitinamide is hydrolyzed.
しかし、これらの方法ではいずれも加水分解工
程を経てｌ（−）−カルニチンを製造しているた
め、その脱水生成物であるアポカルニチンの副成
を防ぐことはむづかしい。したがつてアポカルニ
チンを含有しない純粋なｌ（−）−カルニチンの製
造は甚だ困難である。 However, since all of these methods produce l(-)-carnitine through a hydrolysis step, it is difficult to prevent the by-formation of apocarnitine, which is a dehydration product. Therefore, it is extremely difficult to produce pure l(-)-carnitine that does not contain apocarnitine.
本発明者は、工業的に有利な光学分割について
鋭意研究を重ねた結果、dl−カルニチンをＤ（−）
−マンデル酸で分割させ、アポカルニチンを含ま
ない純粋なｌ（−）−カルニチンを得ることに成功
した。 As a result of extensive research into industrially advantageous optical resolution, the present inventor has determined that dl-carnitine can be converted into D(-).
- By resolution with mandelic acid, we succeeded in obtaining pure l(-)-carnitine containing no apocarnitine.
本発明において使用される分割溶媒としては
C1〜C5の低級アルコール、例えば、メチルアル
コール、エチルアルコール、イソプロピルアルコ
ールなどが挙げられるが、エチルアルコールが特
に好ましい。 The splitting solvent used in the present invention is
Examples include C1 to C5 lower alcohols, such as methyl alcohol, ethyl alcohol, and isopropyl alcohol, with ethyl alcohol being particularly preferred.
分割温度は−20〜30℃で通常行なわれるが10℃
前後が適当である。 The dividing temperature is usually -20 to 30℃, but it is 10℃.
The front and back are appropriate.
本発明においてカルニチン・マンデル酸塩から
光学活性なカルニチンの分離割は強塩基性水溶
液、例えば、５％アンモニア水、１％水酸化ナト
リウム液、又はイオン交換樹脂、例えば、強塩基
性イオン交換樹脂、強酸性イオン交換樹脂が使用
されるが強塩基性イオン交換樹脂が好んで使用さ
れる。 In the present invention, optically active carnitine is separated from carnitine mandelate using a strongly basic aqueous solution, such as 5% aqueous ammonia, 1% sodium hydroxide solution, or an ion exchange resin, such as a strongly basic ion exchange resin. Although strongly acidic ion exchange resins are used, strongly basic ion exchange resins are preferably used.
次に本発明の実施例を挙げるが、本発明を制限
するものではない。 Examples of the present invention will be given below, but the present invention is not limited to the following.
実施例 １
dl−カルニチン160ｇおよびＤ（−）−マンデル
酸152ｇをエチルアルコール400mlに加熱溶解さ
せ、７〜10℃に２時間保ち、析出した結晶を濾取
し、メチルアルコール180mlから再結晶し、ｌ
（−）−カルニチン・Ｄ（−）−マンデル酸塩103ｇ
を得た。融点127〜128℃。Example 1 160 g of dl-carnitine and 152 g of D(-)-mandelic acid were heated and dissolved in 400 ml of ethyl alcohol, kept at 7 to 10°C for 2 hours, the precipitated crystals were collected by filtration, and recrystallized from 180 ml of methyl alcohol. l
(-)-Carnitine D(-)-mandelate 103g
I got it. Melting point 127-128℃.
〔α〕22 D−77.65°（Ｃ＝1.598、水）
ｌ（−）−カルニチン・Ｄ（−）−マンデル酸塩
100ｇを精製水500mlに溶解させ、強塩基性イオン
交換樹脂（三菱化成製造ダイヤイオンSA−20A）
600ml中を通過させ、捕集液1.2を得た。 [α] 22 D −77.65° (C = 1.598, water) l(-)-carnitine D(-)-mandelate
Dissolve 100g in 500ml of purified water and add strong basic ion exchange resin (Diaion SA-20A manufactured by Mitsubishi Kasei).
It was passed through 600 ml to obtain collection liquid 1.2.
捕集液を減圧濃縮し、その残渣にイソプロピル
アルコール200mlを加え一夜冷所に放置し、析出
した結晶を濾取し、〔α〕22 D−29.96°（Ｃ＝1.315、
水）のｌ（−）−カルニチン51ｇを得た。 The collected liquid was concentrated under reduced pressure, and 200 ml of isopropyl alcohol was added to the residue, left in a cool place overnight, and the precipitated crystals were collected by filtration, [α] 22 D −29.96° (C = 1.315,
51 g of l(-)-carnitine (water) was obtained.
Claims (1)
β−ハイドロキシ酪酸メチルベタイン）を溶液中
でＤ（−）−マンデル酸と反応させてｌ（−）−カル
ニチン・Ｄ（−）マンデル酸塩の結晶を析出させ
て分取し、該塩からｌ（−）−カルニチンを分離す
ることを特徴とするｌ（−）カルニチンの製造法。1 dl-carnitine (dl-γ-dimethylamino-
Methyl betaine (β-hydroxybutyrate) is reacted with D(-)-mandelic acid in a solution to precipitate and collect crystals of l(-)-carnitine D(-)mandelate, and from the salt, l(-)-mandelic acid is precipitated. A method for producing l(-)carnitine, which comprises separating (-)-carnitine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10459683A JPS59231048A (en) | 1983-06-11 | 1983-06-11 | Production of l(-) and d(+)-carnitine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10459683A JPS59231048A (en) | 1983-06-11 | 1983-06-11 | Production of l(-) and d(+)-carnitine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59231048A JPS59231048A (en) | 1984-12-25 |
| JPH0471063B2 true JPH0471063B2 (en) | 1992-11-12 |
Family
ID=14384804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10459683A Granted JPS59231048A (en) | 1983-06-11 | 1983-06-11 | Production of l(-) and d(+)-carnitine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59231048A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100255039B1 (en) | 1997-07-28 | 2000-05-01 | 박영구 | Process for the preparation of l-carnitine |
| FR3104969B1 (en) * | 2019-12-20 | 2022-01-07 | Oreal | Process for treating keratin fibers using a composition comprising a salt of carnitine or of a carnitine derivative comprising an aromatic organic anion |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS581105B2 (en) * | 1977-03-24 | 1983-01-10 | 日本化薬株式会社 | Optically active amino acid-mandelic acid complex and method for producing the same |
-
1983
- 1983-06-11 JP JP10459683A patent/JPS59231048A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59231048A (en) | 1984-12-25 |
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