(9R)-6'-methoxycinchonan-9-ol Chemical Properties

Melting point:

111-113°

alpha 

D25 +107.8° (c = 1.02 in ethanol)

Boiling point:

462.75°C (rough estimate)

Density 

1.1294 (rough estimate)

refractive index 

1.5700 (estimate)

storage temp. 

2-8°C

form 

Solid-Liquid Mixture

pka

12.80±0.20(Predicted)

color 

White to off-white

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-42/43

Safety Statements 

22-36/37-45

(9R)-6'-methoxycinchonan-9-ol Usage And Synthesis

Description

This alkaloid is stereoisomeric with epiQuinine and occurs in 'Quinoidine', the mixture of amorphous bases left after extraction of the four primary alkaloids of Cinchona bark. It crystallizes in colourless leaflets from Et20 and is fluorescent in dilute H2S04, It is dextrorotatory with [α]¹⁹_D + 102.4° (c 0.8648, EtOH) and furnishes a dihydrochloride, m.p. 195-6°C (dec.); [α]²⁰_D + 45.5° (c 0.8012, EtOH); a hydrobromide, m.p. 240°C; thiocyanate, m.p. 193°C; [α]²⁰_D + 44.5° (H20) and the dibenzoyl-(+)-tartrate, m.p. 167°C; [α]²⁰¹_D + 3.7° (c 0.8068, EtOH-CHCI 3 ). Catalytic hydrogenation with Pd gives the dihydro derivative, m.p. 122°C; [α]²²_D + 73.1° (c 0.766, EtOH).

Uses

The 9-epimer of Quinidine (Q685000). Antimalarial.

References

Thron, Dirscherl., Annalen, 521,48 (1935)

(9R)-6'-methoxycinchonan-9-ol (572-59-8)Related Product Information

• Quinine