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337714 Sigma-Aldrich

Hydroquinine

98%

Synonym: (8a,9R)-10,11-Dihydro-6′-methoxycinchonan-9-ol, Dihydroquinine, NSC 41799

  • CAS Number 522-66-7

  • Empirical Formula (Hill Notation) C20H26N2O2

  • Molecular Weight 326.43

  •  Beilstein/REAXYS Number 91444

  •  EC Number 208-334-0

  •  MDL number MFCD00151107

  •  PubChem Substance ID 24860494

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Cinchona Alkaloids, Privileged Ligands and Complexes More...
assay   98%
optical activity   [α]25/D −148°, c = 1 in ethanol
mp   168-176 °C (lit.)
SMILES string   CC[C@H]1CN2CCC1C[C@@H]2[C@H](O)c3ccnc4ccc(OC)cc34
InChI   1S/C20H26N2O2/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/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1
InChI key   LJOQGZACKSYWCH-WZBLMQSHSA-N
Gene Information   human ... CYP2D6(1565)

Description

General description

Hydroquinine is a cinchona alkaloid.

Application

Hydroquinine may be used in the preparation of its derivatives such as C9 epihydroquinine, 9-acetoxy-10,11-dihydroquinine and 10,11-dihydroquinine monohydrochloride. It may also be used as a catalyst for the methylhydrazine promoted asymmetric α-hydroxylation of β-keto esters in the presence of molecular oxygen as oxidant to form enantioenriched α-hydroxy β-dicarbonyl compounds.

Packaging

5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
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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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

Peer-Reviewed Papers
15

References

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