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C80407

Sigma-Aldrich

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
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)

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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)

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The alkaloid cinchonidine.
Oleksyn BJ
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 1832-1834 (1982)
Chun-Yin Zhu et al.
Chemical communications (Cambridge, England), (6)(6), 738-740 (2008-05-16)
The reaction of cinchonidine (cinchonine)-derived ammonium salts with nitroolefins in the presence of Cs2CO3 to afford optically active isoxazoline N-oxides with excellent ee and high de values has been developed.
Arkajyoti Sengupta et al.
The Journal of organic chemistry, 77(23), 10525-10536 (2012-11-17)
Mechanism and the origin of enantioselectivity in the decarboxylative protonation of α-amino malonate hemiester promoted by epicinchona-thiourea hybrid organocatalyst is established by using the DFT(M06-2X/6-311+G**//ONIOM2) computational methods. The origin of stereoselectivity rendered by this hybrid bifunctional catalyst in asymmetric protonation
Blaser HU, et al.
Studies in Surface Science and Catalysis, 67, 147-155 (1991)
Erik Schmidt et al.
Langmuir : the ACS journal of surfaces and colloids, 23(15), 8087-8093 (2007-06-23)
Cinchona alkaloids are frequently used for chiral modification of supported noble metal catalysts employed in heterogeneous enantioselective hydrogenation. In order to gain molecular insight into the surface processes occurring at the metal/liquid interface, cinchonidine (CD) adsorption on vapor-deposited Rh/Al2O3 films
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