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27370

Sigma-Aldrich

Cinchonine

crystallized, ≥98.0% (NT)

Synonym(s):

NSC 6176

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About This Item

Empirical Formula (Hill Notation):
C19H22N2O
CAS Number:
118-10-5
Molecular Weight:
294.39
Beilstein:
89689
EC Number:
204-234-6
MDL number:
MFCD00064372
UNSPSC Code:
12352104
PubChem Substance ID:
57648242
NACRES:
NA.22

Assay

≥98.0% (NT)

form

powder

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)

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1A

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Anita Bosak et al.
PloS one, 13(10), e0205193-e0205193 (2018-10-06)
This paper describes the synthesis and anticholinesterase potency of Cinchona-based alkaloids; ten quaternary derivatives of cinchonines and their corresponding pseudo-enantiomeric cinchonidines. The quaternization of quinuclidine moiety of each compound was carried out with groups diverse in their size: methyl, benzyl
Chemistry and biology of Cinchona alkaloids
Kacprzak K
Natural Products, 605-641 (2013)
Qing Gu et al.
Organic letters, 13(19), 5192-5195 (2011-09-15)
Desymmetrization of cyclohexadienones bearing a bisphenylsulfonyl methylene group via asymmetric Michael reaction catalyzed by cinchonine-derived urea was realized to afford a series of highly enantioenriched polycyclic cyclohexenones in high yields and ee's.
Yu-Hua Liao et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(21), 6679-6687 (2012-04-14)
An asymmetric conjugate addition of 3-monosubstituted oxindoles to a range of (E)-1,4-diaryl-2-buten-1,4-diones, catalyzed by commercially available cinchonine, is described. This organocatalytic asymmetric reaction affords a broad range of 3,3'-disubstituted oxindoles that contain a 1,4-dicarbonyl moiety and vicinal quaternary and tertiary
Chensong Pan et al.
Journal of the American Society for Mass Spectrometry, 16(2), 263-270 (2005-02-08)
A method with carbon nanotubes functioning both as the adsorbent of solid-phase extraction (SPE) and the matrix for matrix assisted laser desorption/ionization mass spectrometry (MALDI-MS) to analyze small molecules in solution has been developed. In this method, 10 microL suspensions
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