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857270 Sigma-Aldrich

(+)-Cinchonine

85%

Synonym: Cinchonine monohydrochloride dihydrate, NSC 6176

  • CAS Number 118-10-5

  • Empirical Formula (Hill Notation) C19H22N2O

  • Molecular Weight 294.39

  •  Beilstein/REAXYS Number 89689

  •  EC Number 204-234-6

  •  MDL number MFCD00064372

  •  PubChem Substance ID 24888435

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Chiral Resolution Reagents, Chiral Resolving Reagents,
Quality Level   100
assay   85%
optical activity   [α]23/D +228°, c = 0.5 in ethanol
mp   258-260 °C (lit.)
SMILES string   [H][C@@]12CCN(C[C@H]1C=C)[C@]([H])(C2)[C@@H](O)c3ccnc4ccccc34
InChI   1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1
InChI key   KMPWYEUPVWOPIM-QAMTZSDWSA-N

Description

General description

(+)-Cinchonine, one of the alkaloids found in the barks of cinchona tree, is mainly used in the treatment of malaria. It belongs to the monoclinic crystal system and P21 space group. The solubility of cinchonine can be improved by the formation of inclusion complexes with cyclodextrins.

Application

(+)-Cinchonine, in the presence of lithium diisopropylamide (LDA) forms a complex, which can catalyze the asymmetric conjugate addition of benzyl- and alkylphosphonates to aromatic and heteroaromatic nitroalkenes to form the corresponding adducts.

Packaging

25, 100 g in poly bottle

Other Notes

remainder dihydrocinchonine

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Cinchona Alkaloids - Aldrich ChemFiles 2008, 8.2, 74.

Cinchona alkaloids and their derivatives have proven to catalyze an astonishing array of enantioselective transformations, providing access to chiral products of high enantiopurity.1 The presence of ...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 74.
Keywords: Addition reactions, Aminations, Antimicrobials, Asymmetric synthesis, Catalysis, Desymmetrizations, Dihydroxylations, Ligands, Reductive aminations

Peer-Reviewed Papers
15

References

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