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: 2024-12-18 14:08:52

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.