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857270

Sigma-Aldrich

(+)-Cinchonine

85%

Synonym(s):

Cinchonine monohydrochloride dihydrate, NSC 6176

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About This Item

Empirical Formula (Hill Notation):
C19H22N2O
CAS Number:
118-10-5
Molecular Weight:
294.39
Beilstein:
89689
EC Number:
204-234-6
MDL number:
MFCD00064372
UNSPSC Code:
12352104
PubChem Substance ID:
24888435
NACRES:
NA.22

Assay

85%

form

solid

optical activity

[α]23/D +228°, c = 0.5 in ethanol

mp

258-260 °C (lit.)

SMILES string

[H][C@@]12CCN(C[C@H]1C=C)[C@]([H])(C2)[C@@H](O)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-QAMTZSDWSA-N

General description

(+)-Cinchonine, one of the alkaloids found in the barks of cinchona tree, is mainly used in the treatment of malaria. It belongs to the monoclinic crystal system and P21 space group. The solubility of cinchonine can be improved by the formation of inclusion complexes with cyclodextrins.

Application

(+)-Cinchonine, in the presence of lithium diisopropylamide (LDA) forms a complex, which can catalyze the asymmetric conjugate addition of benzyl- and alkylphosphonates to aromatic and heteroaromatic nitroalkenes to form the corresponding adducts.

Other Notes

remainder dihydrocinchonine

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1A

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

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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Song CE.
Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis, 2-3 (2009)
The molecular and crystal structure of the alkaloid cinchonine.
Oleksyn B, et al.
Acta Crystallographica Section B, Structural Science, 35(2), 440-444 (1979)
Cinchonine catalyzed diastereo-and enantioselective Michael addition of a-lithiated phosphonates to nitroalkenes.
Rai V, et al.
Tetrahedron Asymmetry, 18(22), 2719-2726 (2007)
Xianhong Wen et al.
Bioorganic chemistry, 32(4), 223-233 (2004-06-24)
Cinchonine (Cin) is the primary drug of choice in the treatment of malaria, but its poor solubility has restricted its use via the oral route. Cyclodextrins (CDs) form inclusion complexes with cinchonine to form soluble complexes. This interaction was investigated
A Louise Tillman et al.
Chemical communications (Cambridge, England), (11)(11), 1191-1193 (2006-03-07)
A highly enantioselective Mannich reaction between malonate esters and N-Boc and N-Cbz aldimines, catalysed by a bifunctional cinchonine derivative, has been developed; extension of this methodology to encompass the use of 2-substituted-1,3-dicarbonyl nucleophiles allows the formation of adjacent stereocentres, one
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