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Merck

C80407

Cinchonidine

96%

Synonym(s):

(−)-Cinchonidine

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About This Item

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

Key Documents

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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)

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Related Categories

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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN4960
0000251245
0000228122
0000224061
0000228122

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The alkaloid cinchonidine.
Oleksyn BJ
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 1832-1834 (1982)
Blaser HU, et al.
Studies in Surface Science and Catalysis, 67, 147-155 (1991)
Toshifumi Takeuchi et al.
Chemical record (New York, N.Y.), 5(5), 263-275 (2005-10-08)
Molecular imprinting is a template polymerization technique that can easily provide synthetic polymers capable of molecular recognition for given target molecules. In addition to their highly specific recognition ability, we are attempting to introduce signaling functions to molecularly imprinted polymers
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
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
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