857270

(+)-Cinchonine

85%

• Synonym(s): Cinchonine monohydrochloride dihydrate, NSC 6176
• 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

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302,H317
• Precautionary Statements: P261 - P264 - P272 - P280 - P301 + P312 - P302 + P352
• 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