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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)

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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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)
Erik Schmidt et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(7), 2181-2192 (2009-12-30)
The preparation of stable metal nanoparticles requires a strong interaction between the (organic) stabilizer and the metal surface that might alter the catalytic properties. This behavior has been described as "poisoning" since the stabilizer normally decreases the catalytic activity due
Ryan A Olsen et al.
Journal of the American Chemical Society, 128(49), 15594-15595 (2006-12-07)
The protonation of cinchona alkaloids in solution leads to the severe restriction of their internal rotational degrees of freedom and to the locking of the molecule around a specific conformation held in place by a bridging counterion of the acid
Simon Diezi et al.
Journal of the American Chemical Society, 128(12), 4048-4057 (2006-03-23)
In the Pt-catalyzed hydrogenation of 1,1,1-trifluoro-2,4-diketones, addition of trace amounts of cinchonidine, O-methyl-cinchonidine, or (R,R)-pantoyl-naphthylethylamine induces up to 93% ee and enhances the chemoselectivity up to 100% in the hydrogenation of the activated carbonyl group to an OH function. A
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