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27370 Sigma-Aldrich

Cinchonine

crystallized, ≥98.0% (NT)

Synonym: 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 57648242

  •  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   ≥98.0% (NT)
optical activity   [α]20/D +225±5°, c = 0.5% in ethanol
quality   crystallized
impurities   ~15% dihydrocinchonine (HPLC)
mp   260-263 °C
SMILES string   O[C@H]([C@H]1C[C@@H]2CCN1C[C@@H]2C=C)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
Gene Information   human ... CYP2D6(1565)

Description

General description

Cinchonine is a cinchona alkaloid generally found in the bark of Cinchona officinalis plants. It is a pseudoenantiomer that is commonly employed in malaria therapy. Cinchonine is also used as an organocatalyst in many asymmetric reactions.

Application

Cinchonine can be used:
• As a substrate in the study of supercritical fluid chromatography (SFC) parameters in pharmaceutical analysis.
• To prepare possible butyrylcholinesterase inhibitors.

Packaging

25, 100 g in poly bottle

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
Protocols & Articles
Peer-Reviewed Papers
15

References

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