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145904 Sigma-Aldrich

Quinine

90%

Synonym: 6′-Methoxycinchonidine

  • CAS Number 130-95-0

  • Empirical Formula (Hill Notation) C20H24N2O2

  • Molecular Weight 324.42

  •  Beilstein/REAXYS Number 91867

  •  EC Number 205-003-2

  •  MDL number MFCD00198096

  •  PubChem Substance ID 24848751

  •  NACRES NA.22

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Properties

Related Categories Alkaloid, Asymmetric Synthesis, Cell Biology, Cell Signaling and Neuroscience, Chemical Synthesis,
Quality Level   200
assay   90%
optical activity   [α]25/D −165°, c = 2 in ethanol
mp   173-175 °C (lit.)
SMILES string   COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)c2c1
InChI   1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1
InChI key   LOUPRKONTZGTKE-WZBLMQSHSA-N
Gene Information   human ... ABCB1(5243), CYP2C9(1559), CYP2D6(1565)
rat ... Cyp2d1(266684), Cyp2d2(25053), Cyp2d3(24303), Cyp2d4v1(171522)

Description

General description

Quinine, a cinchona alkaloid found in the bark of the cinchona tree, is known for its anti-malarial property.

Application

Quinine has been used as a standard during the chemical evaluation of alkaloids in the hydroethanolic extracts of endophytic fungi obtained from the leaves of Costus spiralis by TLC.

Resolving agent for carboxylic acids. Catalyzes the kinetic resolution of furanones.

Packaging

10, 50 g in poly bottle

Biochem/physiol Actions

Potassium channel blocker

Other Notes

remainder hydroquinine

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 1
RTECS 
VA6020000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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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

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Peer-Reviewed Papers
15

References

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