Cinchonidine

• (-)- Quinolin- 4-yl -(5- vinyl -1-aza -bicyclo [2.2.2] oct-2- yl) -methanol
• (-)- Cinchonidine

Colorless, crystalline solid

Fixed

205 ° C.

Poorly in water ( 0.25 g · l-1 at 20 ° C)

206 mg · kg -1 ( LD50, rat, ip)

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Cinchonidine belongs to the group of China alkaloids. It is - like most alkaloids - physiologically active and is a vegetable poison.

Occurrence

(-)- Cinchonidine and the isomer ( )- cinchonine occur naturally in the bark of China bark trees (mainly cinchona Ledgeriana ) before and it can be extracted.

Chemical Properties and Uses

With light and air exclusion colorless, slightly water -soluble substance is stable; under the influence of light and oxidizing agents cinchonidine is decomposed or oxidized to yellowish colored products. The distillation of cinchonine quinoline with potassium hydroxide is formed.

(-)- Cinchonidine is used for the resolution of racemates. It forms with racemic acids diastereomeric salts which can be separated by fractional crystallization. (-)- Cinchonidine is one of the cinchona alkaloid catalysts as chiral amines Lewis bases. These catalytic reactions are in the org. Chemical wide range of uses. An example of this is the 1,4- addition reaction by Wynberg.

Safety

A LD50 value of 206 mg / kg determined cinchonidin with intraperitoneal administration - In animal studies with rats, for (). The animals were reduced even at sublethal doses active until drowsy and showed muscle tremors and convulsions.