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Table 1 1 H-NMR data of compounds 1-8 at 300 (compounds 2,3,4,5,7), 400 (compound 8) and 500 (compound 6) MHz; δ in ppm, J and W 1/2 in Hz

From: Biotransformation of oral contraceptive ethynodiol diacetate with microbial and plant cell cultures

COMPOUNDS

Carbon

1

2

3

4

5

6

7

8

1

1.41, 2.05

1.12, 2.07,

1.36, 1.70

1.38, 1.94

1.52, 2.24

1.54, 2.25

1.74, 1.96

1.75, 1.92

2

2.01, 2.27 dt, J=13.4, 2.8

1.33, 1.94

1.46, 2.01

1.55, 1.83

2.21, 2.38

2.28, 2.37

1.95, 2.23

1.91, 1.98

3

5.20 br s, W1/2=19.6

4.05, m (W1/2=17.4 Hz)

5.20, m (W1/2=22.8 Hz)

4.01, m (W1/2=15.6 Hz)

-

-

4.14 m, W1/2=16.8

5.85d J =9.6

4

5.32

5.55, br s (W1/2=9.7 Hz)

5.55, br s, (W1/2=17.2 Hz)

5.40, br s (W1/2=9.37 Hz)

5.81 s

5.81 s

5.37

5.50 d J=9.6

5

-

-

-

-

-

-

-

-

6

0.95, 1.68

4.12, br s (W1/2=9.6 Hz)

4.16, br s, (W1/2=17.1 Hz)

2.05, 2.41

2.27, 2.49

2.29, 2.45 dt, J=14.5, 3.28

1.67, 1.82

1.77, 1.82

7

1.17, 1.80

2.05, 2.65

1.13, 1.87

0.90, 1.75

1.12, 1.83

1.06, 1.82

0.94, 1.73

1.15, 1.78

8

1.25

1.94

1.82

1.72

1.36

1.35

1.25

0.82

9

0.71

0.60

0.65

0.80

0.85

0.86

0.67

1.08

10

1.77

1.80

2.20

-

2.06

2.07 td, J=10.5, 4.7

1.75

1.47

11

 

1.25, 1.84

1.23, 1.85

1.59, 1.67

1.22, 1.91

1.23, 1.88

1.13, 2.02

0.78, 1.51

12

1.67, 1.82

1.65, 1.83

1.66, 1.84

1.66, 1.82

1.70, 1.87

1.63, 1.75

1.27, 2.04

1.54, 1.68

13

-

-

-

-

-

-

-

-

14

1.51

1.50

1.52

1.48

1.54

1.51

1.50

1.42

15

1.31, 1.72

1.37, 1.67

1.27, 1.29

1.37, 1.72

1.33, 1.75

1.27, 1.54

1.32, 1.77

1.28, 1.67

16

1.98, 2.72

2.15, 2.65

2.04, 2.65

2.05, 2.65

1.97, 2.73 ddd, J=15, 9.6, 5.7

1.98, 2.27

1.99, 2.70 ddd J=15, 6.0, 3.6

1.94, 2.27

17

-

-

-

-

-

 

-

-

18

0.87, s

0.94, s

0.95, s

0.93, s

0.91, s

0.89, s

0.87, s

0.84, s

20

-

-

-

-

-

-

-

-

21

2.55, s

2.94, s

2.97, s

2.95, s

2.57, s

2.55, s

2.55, s

2.55, s

22

-

-

-

-

-

 

-

 

23

2.02

2.01, s

2.00, s

1.99, s

2.02 s

 

2.01 s

 

24

        

25

2.02

2.01, s

2.00, s

1.99, s

    
  1. Note: Assignments based on COSY, HMBC and HMQC spectra. Assignments shown without multiplicity means multiplet.