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MilliporeSigma

C80407

Cinchonidine

96%

Synonym(s):

(−)-Cinchonidine

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$42.20

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$253.00

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Available to ship onJanuary 06, 2026Details

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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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Product Name

Cinchonidine, 96%

InChI key

KMPWYEUPVWOPIM-KODHJQJWSA-N

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

SMILES string

O[C@@H]([C@@H]1C[C@@H]2CCN1C[C@@H]2C=C)c3ccnc4ccccc34

assay

96%

form

powder

optical activity

[α]23/D −109.2°, c = 1.5 in ethanol

mp

204-206 °C (lit.)

Quality Level

200

Gene Information

human ... CYP2D6(1565)

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This Item
27370857270PHL80961
Cinchonidine 96%

Sigma-Aldrich

C80407

Cinchonidine

Cinchonine crystallized, ≥98.0% (NT)

Sigma-Aldrich

27370

Cinchonine

(+)-Cinchonine 85%

Sigma-Aldrich

857270

(+)-Cinchonine

(-)-Cinchonidine phyproof® Reference Substance

PHL80961

(-)-Cinchonidine

assay

96%

assay

≥98.0% (NT)

assay

85%

assay

≥95.0% (HPLC)

form

powder

form

powder

form

solid

form

powder

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

-

optical activity

[α]23/D −109.2°, c = 1.5 in ethanol

optical activity

[α]20/D +225±5°, c = 0.5% in ethanol

optical activity

[α]23/D +228°, c = 0.5 in ethanol

optical activity

-

mp

204-206 °C (lit.)

mp

260-263 °C

mp

258-260 °C (lit.)

mp

204-206 °C (lit.)

Gene Information

human ... CYP2D6(1565)

Gene Information

human ... CYP2D6(1565)

Gene Information

-

Gene Information

-

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.[1]

General description

Cinchonidine is a cinchona alkaloid, which belongs to the orthorhombic crystal system and P212121 space group.[2]

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)
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
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
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