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Cinchonine

Cinchonine Structure
CAS No.
118-10-5
Chemical Name:
Cinchonine
Synonyms
Cinchonin;(S)-quinolin-4-yl((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol;D-CINCHONINE;NSC 6176;LA40221);CINCHONINE;Xin Kening;Xin Kenning;Cinchoninne;(+)-cinconine
CBNumber:
CB0244972
Molecular Formula:
C19H22N2O
Molecular Weight:
294.39
MOL File:
118-10-5.mol
MSDS File:
SDS
Modify Date:
2024/5/27 17:30:58

Cinchonine Properties

Melting point 260-263 °C
alpha 224 º (c=0.5, alcohol)
Boiling point 436.16°C (rough estimate)
Density 1.0863 (rough estimate)
vapor pressure 0Pa at 25℃
refractive index 223 ° (C=0.5, EtOH)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility 0.25g/l
form Micro-Crystalline Powder
pka 5.85, 9.92(at 25℃)
color White to light beige
PH 9.0 (0.25g/l, H2O, 20℃)(as aqueous solution)
optical activity [α]23/D +228°, c = 0.5 in ethanol
Water Solubility Insoluble
Sensitive Light Sensitive
Merck 14,2287
BRN 89689
Stability Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
InChIKey KMPWYEUPVWOPIM-QHQSXHFQSA-N
LogP 2.82 at 25℃
CAS DataBase Reference 118-10-5(CAS DataBase Reference)
NIST Chemistry Reference Cinchonine(118-10-5)
EPA Substance Registry System Cinchonan-9-ol, (9S)- (118-10-5)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H317
Precautionary statements  P261-P264-P270-P280-P301+P312-P302+P352
Hazard Codes  Xn
Risk Statements  20/22-20/21/22
Safety Statements  26-36-36/37
RIDADR  1544
WGK Germany  3
RTECS  GD3500000
8-34
HazardClass  6.1(b)
PackingGroup  III
HS Code  29339900
Toxicity LD50 i.p. in rats: 152 mg/kg (Johnson, Poe)
NFPA 704
1
2 1

Cinchonine price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 857270 (+)-Cinchonine 85% 118-10-5 25G ₹4286.7 2022-06-14 Buy
Sigma-Aldrich(India) 857270 (+)-Cinchonine 85% 118-10-5 100G ₹8854.85 2022-06-14 Buy
Sigma-Aldrich(India) 8.02506 (+)-Cinchonine for resolution of racemates for synthesis 118-10-5 25G ₹6750.01 2022-06-14 Buy
Sigma-Aldrich(India) 8.02506 (+)-Cinchonine for resolution of racemates for synthesis 118-10-5 100G ₹17299.99 2022-06-14 Buy
Sigma-Aldrich(India) 27370 Cinchonine crystallized, ≥98.0% (NT) 118-10-5 25G ₹4957.85 2022-06-14 Buy
Product number Packaging Price Buy
857270 25G ₹4286.7 Buy
857270 100G ₹8854.85 Buy
8.02506 25G ₹6750.01 Buy
8.02506 100G ₹17299.99 Buy
27370 25G ₹4957.85 Buy

Cinchonine Chemical Properties,Uses,Production

Description

Cinchonine is a cinchona alkaloid generally found in the bark of Cinchona officinalis plants. It is a pseudoenantiomer that is commonly employed in malaria therapy. Cinchonine is also used as an organocatalyst in many asymmetric reactions. It is a stereoisomer and pseudo-enantiomer of cinchonidine. It is structurally similar to quinine, an antimalarial drug.

Chemical Properties

white to light yellow crystal powde

Uses

Cinchonine occurs in most varieties of cinchonabark (Cinchona micrantha and Rubiaceae).It is used as an antimalarial agent.

Definition

ChEBI: Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (S configuration). It occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.

Health Hazard

The toxic effects from high doses of cinchonineinclude tinnitus, vomiting, diarrhea, andfever. The toxic effects noted in rats were excitement, change in motor activity, andconvulsions. An intraperitoneal LD50 valuein rats is 152 mg/kg.

Purification Methods

Crystallise cinchonine from EtOH or diethyl ether. For the N-benzylcinchoninium chloride see above entry in this section. [Rabe Justus Liebigs Ann Chem 365 366, 371 1909, Beilstein 23 III/IV 2819, 2832.]

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(+)-cinconine (8r,9s)-cinchonine (9s)-cinchonan-9-o (9S)-Cinchonan-9-ol (+)-CINCHONINE CINCHONINE CINCHONAN-9-OL,(9S)- Cinchonine, 98+% Cinchonine dihydrate monohydrochloride Cinchonine Solution [for spray] (9S)-Cinconan-9-ol Cinchonine,99% (+)-Cinchonine, 98+%, cont. up to 3% quinidine/dihydroquinidine and 3% quinine/dihydroquinine Cinchonine ,98.5% (5-Ethenyl-1-azabicyclo[2.2.2]oct-2-yl)(quinolin-4-yl)methanol 4-[(5-Ethenyl-1-azabicyclo[2.2.2]oct-2-yl)hydroxymethyl]quinoline (S)-{5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)Methanol Cinchonine, 99% 100GR Cinchonine, 99% 25GR (+)-Cinchonine, cont. up to 3% quinidine/dihydroquinidine and 3% quinine/dihydroquinine Cinchonine, synthesis grade NSC 6176 (+)-CINCHONINE FOR RESOLUTION OF RACEMAT (1S)-Quinolin-4-yl((2R,4S,5R)-5-vinylquinuclidin-2-yl)Methanol alpha-(5-vinyl-2-quinolyl)-2-quinuclidinemethano alpha-4-quinolyl-5-vinyl-2-quinuclidinemethano CINCHONINE FREE BASE CINCHONINE, CRYSTALLIZED CINCHONINE PURE (+)-Quinolin-4-yl(5-vinylquinuclidin-2-yl)Methanol Cinchonine (8CI) Cinchonine (base and/or unspecified salts) 4-Quinolyl(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methanol CINCHONINE:CINCHONAN-9-OL,(9S)-, (+)-Cinchonine, 98+%, cont. up to 3% quinidine/dihydroquinidine and 3% quinine/dihydroquinidine CINCHONINE(P) CINCHONINE(RG) homocinchonidine homoquinidine Cinchonine , 98.0%(T) -Quinolin-4-yl(5-vinylquinuclidin-2-yl) Cinchonine (Synonyms: (8R,9S)-Cinchonine LA40221) [5-ethenyl-4-(2-quinolinyl)-1-azabicyclo[2.2.2]octan-2-yl]methanol Cinchonine(LA40221) Cinchonine ((8R,9S)-Cinchonine Xin Kenning Xin Kening Cinchonine > (S)-Quinolin-4-yl((1S,2R,4S,5S)-5-vinylquinuclidin-2-yl)methanol Quinidine EP Impurity B 4-QUINOLYL(5-VINYL-1-AZABICYCLO[2.2.2]OCT-2-YL)MET Cinchonine USP/EP/BP [(5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol CINCHONINE For Synthesis UNII-WTV8EPZ396 D-CINCHONINE Cinchonin