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Characterisation
General
Chemical name
- 4-hydroxy-3-(3-oxo-1-phenyl-butyl)-chromen-2-one
- 3-(2-acetyl-1-phenylethyl)-4-hydroxycoumarin
- (+ -)warfarin
CAS number
81-81-2
Molecular Formula
C19H16O4
Molecular weight
308.33
2D structure
Melting Point / oC
172-173
Isomerism
Optical ; 2 enantiomers
Optical Rotation [α]D25 (in acetic acid)
S-warfarin : -25.5 ± 1 o
R-warfarin : +24.8 ± 1 o
Infrared Spectrum
(i) Gas Phase
(ii) In NujolThe interpretation of the NMR is given below.8
The IR spectrum of warfarin shows characteristic peaks at 1747 cm-1 corresponding to C=O stretch. The peak in the region 3200 cm-1 corresponds to the OH group.
Mass Spectrum
The Electron-Impact (EI) mass spectrum of warfarin is shown below.
The structures associated with some of the fragments are given below.7
Proton
Chemical Shift
Multiplicity
1
7.32
d
2
7.61
ddd
3
7.38
t
4
7.92
dd
5
7.15-7.25
m
6
7.27
t
7
7.15-7.25
m
8
7.27
t
9
7.15-7.25
m
10
4.10
dd
11
2.00
2.40
dd
dd
12
1.71
s