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22620 Sigma-Aldrich

Quinine

suitable for fluorescence, anhydrous, ≥98.0% (dried material, NT)

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 57647993

  •  NACRES NA.32

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Properties

Related Categories Alkaloid, Asymmetric Synthesis, Biochemicals and Reagents, Cell Biology, Chemical Synthesis,
assay   ≥98.0% (dried material, NT)
optical activity   [α]20/D −126±5°, c = 1% in chloroform
impurities   ≤5% dihydroquinine (HPLC)
loss   ≤1% loss on drying, 110 °C
mp   173-175 °C (lit.)
solubility   H2O: soluble
fluorescence   λex 347 nm; λem 448 nm in 0.5 M sulfuric acid
suitability   suitable for fluorescence
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

Biochem/physiol Actions

Potassium channel blocker

Other Notes

Chiral catalyst, used e.g. in highly enantioselective [2+2] cycloadditions; In additions of diethylzinc to aldehydes.

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
VA6020000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

HPLC Analysis of Alkaloids on Discovery® RP-AmideC16

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HPLC Analysis of Amides on Discovery® RP-Amide C16

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Amides on Discovery® RP-Amide C16
Keywords: Analgesics, Chromatography, High performance liquid chromatography, Pharmaceutical

Peer-Reviewed Papers
15

References

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