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Cinchonine

Name: Cinchonine
Brand: ALDRICH

crystallized, ≥98.0% (NT)

Synonyme(s) :

NSC 6176

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About This Item

Formule empirique (notation de Hill):

C₁₉H₂₂N₂O

Numéro CAS:

118-10-5

Poids moléculaire :

294.39

Numéro Beilstein :

89689

Numéro CE :

204-234-6

Numéro MDL:

MFCD00064372

Code UNSPSC :

12352104

ID de substance PubChem :

57648242

Nomenclature NACRES :

NA.22

Pureté

≥98.0% (NT)

Forme

powder

Activité optique

[α]20/D +225±5°, c = 0.5% in ethanol

Qualité

crystallized

Impuretés

~15% dihydrocinchonine (HPLC)

Pf

260-263 °C

Chaîne SMILES

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

Clé InChI

KMPWYEUPVWOPIM-QAMTZSDWSA-N

Informations sur le gène

human ... CYP2D6(1565)

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Description générale

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.

Pictogrammes

GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H317

Conseils de prudence

P261 - P264 - P272 - P280 - P301 + P312 - P302 + P352

Classification des risques

Acute Tox. 4 Oral - Skin Sens. 1A

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Design and evaluation of selective butyrylcholinesterase inhibitors based on Cinchona alkaloid scaffold.

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)

Desymmetrization of cyclohexadienones via asymmetric Michael reaction catalyzed by cinchonine-derived urea.

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.

Organocatalytic asymmetric conjugate addition of 3-monosubstituted oxindoles to (E)-1,4-diaryl-2-buten-1,4-diones: a strategy for the indirect enantioselective furanylation and pyrrolylation of 3-alkyloxindoles.

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

Carbon nanotubes as adsorbent of solid-phase extraction and matrix for laser desorption/ionization mass spectrometry.

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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