This document contains NMR spectroscopy data from analyses of piperine. There are 1H and 13C NMR spectra as well as 2D 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC correlation spectra. The spectra indicate the number of proton and carbon signals, as well as which protons are correlated to which carbons in the piperine molecule through 1-bond, 2-bond, and longer-range couplings.

1. 7.6 7.4 7.2 7.0 6.8 6.6 6.4 6.2 PPM
300 MHz
500 MHz
14
N
16
5
4
O
1
O
3
2
13
6
O
15
12
11
10
9
7
8
17
21
20
18
19 H
13a
H
12a
H
11a
H
10a
12
6
9 10
11 13
8
CHCl3
piperine
Clauss(cgf) 070107
15mg in 100% CDCl3

2. 1.00
1.00
1.05
1.10
1.99
1.04
2.05
4.24
1.09
2.17
4.21
8 7 6 5 4 3 2 1 0 PPM
piperine
Clauss(cgf) 070107
15mg in 100% CDCl3
1H spectrum at 500 MHz

3. piperine
Clauss(cgf) 070107
15mg in 100% CDCl3
1H spectrum at 500 MHz
8 7 6 5 4 3 2 1 0 PPM
7.487.467.447.427.407.38 PPM
7.00 6.95 6.90 6.85 6.80 6.75 PPM
6.480
6.470
6.460
6.450
6.440PPM
3.80
3.75
3.70
3.65
3.60
3.55
3.50PPM
1.85 1.80 1.75 1.70 1.65 1.60 1.55 PPM
60Hz/cm
all expansions
20Hz/cm unless
otherwise noted
14
N
16
5
4
O
1
O
3
2
13
6
O
15
12
11
10
9
7
8
17
21
20
18
19 H
13a
H
12a
H
11a
H
10a
12
6
9
10
11
13
8
-OH
18 +
20
17 +
21 19
2

4. F2 (ppm)
0
1
2
3
4
5
6
7
8
F1
(ppm)
1
2
3
4
5
6
7
8
piperine
Clauss(cgf) 070107
15mg in 100% CDCl3
1H gcosy spectrum
at 500 MHz
14
N
16
5
4
O
1
O
3
2
13
6
O
15
12
11
10
9
7
8
17
21
20
18
19 H
13a
H
12a
H
11a
H
10a

5. piperine
Clauss(cgf) 070107
15mg in 100% CDCl3
1H gcosy expansion
at 500 MHz
14
N
16
5
4
O
1
O
3
2
13
6
O
15
12
11
10
9
7
8
17
21
20
18
19 H
13a
H
12a
H
11a
H
10a
F2 (ppm)
6.6
6.8
7.0
7.2
7.4
F1
(ppm)
6.6
6.8
7.0
7.2
7.4

6. F2 (ppm)
1
2
3
4
5
6
7
8
F1
(ppm)
40
60
80
100
120
140
160
piperine
Clauss(cgf) 070107
15mg in 100% CDCl3
1H HSQCAD
(1-bond 1H-13C correlation)
at 500 MHz
-CH2- show in
-CH3, >CH- in
red
blue
14
N
16
5
4
O
1
O
3
2
13
6
O
15
12
11
10
9
7
8
17
21
20
18
19 H
13a
H
12a
H
11a
H
10a

7. F2 (ppm)
6.0
6.2
6.4
6.6
6.8
7.0
7.2
7.4
F1
(ppm)
110
120
130
140
150
160
piperine
Clauss(cgf) 070107
15mg in 100% CDCl3
expansion of 1H HSQCAD
(1-bond 1H-13C correlation)
at 500 MHz
This adiabatic experiment
inverts -CH2-, show in
-CH3 and >CH- are left
the experiment,
and are shown in
.
.
red
positive in
blue
14
N
16
5
4
O
1
O
3
2
13
6
O
15
12
11
10
9
7
8
17
21
20
18
19 H
13a
H
12a
H
11a
H
10a
12
10
11
13
8
6 9
2

8. F2 (ppm)
2
3
4
5
6
7
8 2
3
4
5
6
7
8
F1
(ppm)
40
60
80
100
120
140
160
F1
(ppm)
40
60
80
100
120
140
160
piperine
Clauss(cgf) 070107
15mg in 100% CDCl3
1H gHMBCAD (long-range
1H-13C correlation)
at 500 MHz
14
N
16
5
4
O
1
O
3
2
13
6
O
15
12
11
10
9
7
8
17
21
20
18
19 H
13a
H
12a
H
11a
H
10a

9. piperine
Clauss(cgf) 070107
15mg in 100% CDCl3
expansion of 1H
gHMBCAD (n-bond
1H-13C correlation)
at 500 MHz
1-bond artifacts
(doublets in the F2
dimension split by
J ~160Hz) have
been colored yellow.
CH
F2 (ppm)
6.0
6.2
6.4
6.6
6.8
7.0
7.2
7.4 F2 (ppm)
6.0
6.2
6.4
6.6
6.8
7.0
7.2
7.4
F1
(ppm)
110
120
130
140
150
160
F1
(ppm)
110
120
130
140
150
160
C14
C10
C8
C7
12
6
9
10
11 13
8
2
C4,C5
C11
C13
C12
C9
C6
14
N
16
5
4
O
1
O
3
2
13
6
O
15
12
11
10
9
7
8
17
21
20
18
19 H
13a
H
12a
H
11a
H
10a