Quinine Base – Fine Chemical

Buchler is worldwide the leading supplier of Quinine Base (CAS-No. 130-95-0), the most famous cinchona alkaloid compound, providing the framework of sophisticated highly efficient chiral organocatalysts. Together with its derivatives it enables the synthesis of complex chiral compounds in high yield and with remarkable high enantioselectivity. Furthermore the catalysts are eco-friendly, non-toxic, highly stable and available for reasonable prices. As green catalysts these compounds are widely used in large-scale applications. Please also take a look into our free of charge Chiral Catalyst Search Database, containing hundreds of examples. Lots of highly efficient enantioselective organocatalysts contain the Quinine framework. For example urea and thiourea derivatives and other Cinchona Alkaloids are widely used as a chiral catalyst to promote Aldol reaction, Aminations, Cycloadditions, Halogenations, Mannich reaction, Michael Addition, Henry reactions, Epoxidations, Friedel-Crafts reaction etc.

Application

Quinine based Phase Transfer Catalysts (PTC) are often applied to establish the isoxazoline group. For example the key synthetic steps of (S)-Afoxolaner, Flurenaler, Isocycloseram, (S)-Methiozolin, Sorolaner are being catalyzed by Cinchona Alkaloid PTCs. In addition Desymmetrizations (Briveracetam) of prochiral anhydrides can be achieved easily by Quinine based catalysts with extraordinary high enantioselectivity (> 99 % ee). Moreover the resolution of racemates can be simply carried out using Cinchona Alkaloid derivatives as a chiral tool obtaining high values of enantiomeric excess.

Apart from the application in asymmetric synthesis Quinine is a bitter agent in the beverage industry. For the food industry Quinine products are available as Base, Hydrochloride or Sulfate. Quinine is responsible for the unique bitter taste of beverages such as Tonic Water, Bitter Lemon and many others. Furthermore Quinine and their salts are used as antimalarial drugs and to treat muscular disorders like leg cramps.

Physical properties

Quinine Base (CAS-No.: 130-95-0) is a white or almost white, crystalline powder or it consists of fine, colourless needles, being  soluble in ethanol, CHCl₃ and methanol. The melting point is in the range of 174-179 °C. This compound is not hygroscopic and contains less than 1.0 % water. It could be stored at ambient conditions in well-closed, light-resistant containers. Buchler is the leading manufacturer of Quinine, offering the compound in two different quality grades: highly purified (99.5 %) or standard quality (approx. 95 %).

Synonyms

Chinin, 6`-Methoxycinchonidine; (8S,9R)-6´-Methoxycinchonan-9-ol; (8α,9R)-6´-Methoxycinchonan-9-ol, (R)-[(2S,4S,5R)-5-Ethenyl-1-azabicyclo[2.2.2]oct-2-yl](6-methoxyquinolin-4-yl)methanol, 1-(6-Methoxychinolin-4-yl)-1-(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methanol and 1-(6-Methoxychinolin-4-yl)-1-(5-vinyl-1,4-ethanopiperidin-2-yl)methanol

NMR spectra of the structural elucidation can be viewed here: