Cinchonidine
Synonym(s):(−)-Cinchonidine;Cinchonidine
- CAS NO.：485-71-2
- Empirical Formula: C19H22N2O
- Molecular Weight: 294.39
- MDL number: MFCD00006783
- EINECS: 207-622-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2026-01-23 16:19:27
What is Cinchonidine?
Description
Cinchonidine is an alkaloid found in the bark of most varieties of cinchona shrubs. It and its stereoisomer cinchonine have long been used to direct chirality in the synthesis of asymmetric organic compounds.?More recently, Dutch chemists created chiral metals by crystallizing their salts in the presence of cinchonidine.
Chemical properties
white to light yellow crystal powde
The Uses of Cinchonidine
Cinchonidine occurs in most varieties of Cinchona bark and is stereoisomeric with Cinchonine. Cinchonidine exhibits Antimalarial properties.
The Uses of Cinchonidine
antiamebic, antiprotozoal
Definition
ChEBI: 8-epi-Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (R configuration). A diasteroisomer of cinchonine, it occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.
Flammability and Explosibility
Non flammable
Purification Methods
Crystallise cinchonidine from aqueous EtOH. For the N-benzylcinchonidinium chloride see above entry in this section. [Beilstein 23 III/IV 2824.]
Properties of Cinchonidine
| Melting point: | 204-206 °C(lit.) |
| Boiling point: | 436.16°C (rough estimate) |
| alpha | -115 º (c=1, EtOH) |
| Density | 1.0863 (rough estimate) |
| vapor pressure | 0Pa at 25℃ |
| refractive index | -107.5 ° (C=1, EtOH) |
| storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
| solubility | 0.25g/l |
| form | Crystalline Powder |
| pka | 5.80, 10.03(at 25℃) |
| color | White to cream |
| PH | 9 (0.2g/l, H2O, 20℃) |
| optical activity | [α]23/D 109.2°, c = 1.5 in ethanol |
| Water Solubility | Insoluble |
| Sensitive | Light Sensitive |
| Merck | 14,2286 |
| BRN | 89690 |
| Stability: | Stable, but light-sensitive. Incompatible with strong oxidizing agents. |
| CAS DataBase Reference | 485-71-2(CAS DataBase Reference) |
| NIST Chemistry Reference | Cinchonidine(485-71-2) |
| EPA Substance Registry System | Cinchonan-9-ol, (8.alpha.,9R)- (485-71-2) |
Safety information for Cinchonidine
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H302:Acute toxicity,oral H317:Sensitisation, Skin H319:Serious eye damage/eye irritation |
| Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Cinchonidine
| InChIKey | KMPWYEUPVWOPIM-NAHPKXJFSA-N |
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![O-[BIS(TRIFLUOROMETHYL)PHENYL]CINCHONIDINE](https://img.chemicalbook.in/StructureFile/ChemBookStructure9/GIF/CB3198755.gif)
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