Skip to Content
Merck
All Photos(3)

Documents

C80407

Sigma-Aldrich

Cinchonidine

96%

Synonym(s):

(−)-Cinchonidine

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C19H22N2O
CAS Number:
485-71-2
Molecular Weight:
294.39
Beilstein:
89690
EC Number:
207-622-3
MDL number:
MFCD00006783
UNSPSC Code:
12352005
PubChem Substance ID:
24893015
NACRES:
NA.22

Quality Level

200

Assay

96%

form

powder

optical activity

[α]23/D −109.2°, c = 1.5 in ethanol

mp

204-206 °C (lit.)

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-KODHJQJWSA-N

Gene Information

human ... CYP2D6(1565)

Looking for similar products? Visit Product Comparison Guide

General description

Cinchonidine is a cinchona alkaloid, which belongs to the orthorhombic crystal system and P212121 space group.

Application

The enantioselective hydrogenation of ethyl pyruvate in the presence of cinchonidine modified platinum/alumina catalyst leads to the enantiomeric excess of ethyl (R)-lactate.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Sens. 1A

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Blaser HU, et al.
Studies in Surface Science and Catalysis, 67, 147-155 (1991)
The alkaloid cinchonidine.
Oleksyn BJ
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 1832-1834 (1982)
Nobutaka Maeda et al.
Journal of the American Chemical Society, 133(49), 19567-19569 (2011-11-17)
An understanding of the chiral site-substrate interaction is a necessary prerequisite for the rational design and development of efficient heterogeneous asymmetric catalysts. For the enantioselective hydrogenation of α-ketoesters on cinchona-modified platinum, it has earlier been proposed that the crucial interaction
Atsushi Urakawa et al.
The journal of physical chemistry. A, 112(31), 7250-7255 (2008-07-19)
Conformational space of cinchonidine has been explored by means of ab initio potential and free energy surfaces, and the temperature-induced changes of conformational populations were studied by a combined NOESY-DFT analysis. The DFT-derived potential energy surface investigation identified four new
Angelo Vargas et al.
The journal of physical chemistry. A, 110(3), 1118-1127 (2006-01-20)
The conformational analysis of the synthetic chiral modifier O-phenyl-cinchonidine (PhOCD) used in enantioselective hydrogenations over noble metal catalysts has been performed at a PM3 semiempirical level in vacuum. The minimum energy conformations calculated at the DFT level with a medium-size
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service