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Cinchonidine

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Cinchonidine Basic information

Product Name:
Cinchonidine
Synonyms:
  • (8-alpha,9r)-cinchonan-9-o
  • (8alpha,9theta)-cinchonan-9-o
  • (8s,9r)-cinchonidine
  • 2-Quinuclidinemethanol, alpha-4-quinolyl-5-vinyl-
  • Cinchonan-9-ol
  • Cinchonan-9-ol, (8alpha,9R)-
  • Cinchovatine
  • Cinchonidinederivedcatalyst
CAS:
485-71-2
MF:
C19H22N2O
MW:
294.39
EINECS:
207-622-3
Product Categories:
  • AMEBARSONE
  • Aromatics
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Alkaloids
  • chiral
  • Biochemistry
  • for Resolution of Acids
  • Optical Resolution
  • Quinoline Alkaloids
  • Quinolinecarboxylic Acids, etc.
  • Quinolines
  • cyclic compounds
  • Synthetic Organic Chemistry
Mol File:
485-71-2.mol
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Cinchonidine Chemical Properties

Melting point:
204-206 °C(lit.)
alpha 
-115 º (c=1, EtOH)
Boiling point:
436.16°C (rough estimate)
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.
InChIKey
KMPWYEUPVWOPIM-NAHPKXJFSA-N
LogP
2.68 at 25℃
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)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
20/21/22-42/43-36/37/38-20/22-48/22-43-22-63
Safety Statements 
22-24/25-36/37-36-26
RIDADR 
1544
WGK Germany 
3
RTECS 
GD2975000
TSCA 
Yes
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29392900
Toxicity
LD50 i.p. in rats: 206 mg/kg (Johnson, Poe); LD50 orally in quail: >316 mg/kg (Schafer)

MSDS

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Cinchonidine Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

antiamebic, antiprotozoal

Uses

Occurs in most varieties of Cinchona

Uses

Cinchonidine occurs in most varieties of Cinchona bark and is stereoisomeric with Cinchonine. Cinchonidine exhibits Antimalarial properties.

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

Nonflammable

Purification Methods

Crystallise cinchonidine from aqueous EtOH. For the N-benzylcinchonidinium chloride see above entry in this section. [Beilstein 23 III/IV 2824.]

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