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857270

Sigma-Aldrich

(+)-Cinchonine

85%

Synonym(s):

Cinchonine monohydrochloride dihydrate, NSC 6176

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Estimated to ship onMarch 29, 2025

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25 G
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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

¥5,100

List Price¥6,660Save 23%

Estimated to ship onMarch 29, 2025

Request a Bulk Order

Quality Level

100

Assay

85%

form

solid

optical activity

[α]23/D +228°, c = 0.5 in ethanol

mp

258-260 °C (lit.)

functional group

hydroxyl

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,[1] is mainly used in the treatment of malaria.[2] It belongs to the monoclinic crystal system and P21 space group.[3] The solubility of cinchonine can be improved by the formation of inclusion complexes with cyclodextrins.[2]

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.[4]

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

857270-250G:
857270-BULK:
857270-VAR:
857270-25G:
857270-100G:

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Certificates of Analysis (COA)

Lot/Batch Number
STBL0665
STBK8251
STBK0347
STBJ3021
STBH2366

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Sigma-Aldrich

22620

Quinine

Cinchonine catalyzed diastereo-and enantioselective Michael addition of a-lithiated phosphonates to nitroalkenes.
Rai V, et al.
Tetrahedron Asymmetry, 18(22), 2719-2726 (2007)
The molecular and crystal structure of the alkaloid cinchonine.
Oleksyn B, et al.
Acta Crystallographica Section B, Structural Science, 35(2), 440-444 (1979)
Song CE.
Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis, 2-3 (2009)
Yu-Hua Liao et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(21), 6679-6687 (2012-04-14)
An asymmetric conjugate addition of 3-monosubstituted oxindoles to a range of (E)-1,4-diaryl-2-buten-1,4-diones, catalyzed by commercially available cinchonine, is described. This organocatalytic asymmetric reaction affords a broad range of 3,3'-disubstituted oxindoles that contain a 1,4-dicarbonyl moiety and vicinal quaternary and tertiary
Qing Gu et al.
Organic letters, 13(19), 5192-5195 (2011-09-15)
Desymmetrization of cyclohexadienones bearing a bisphenylsulfonyl methylene group via asymmetric Michael reaction catalyzed by cinchonine-derived urea was realized to afford a series of highly enantioenriched polycyclic cyclohexenones in high yields and ee's.
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