SUPPORTING INFORMATION Constituents of Cypriol Oil (Cyperus ...
SUPPORTING INFORMATION
Constituents of Cypriol Oil (Cyperus scariosus R.Br.): N-Containing Molecules and Key Aroma Components. Robin A. Clery,* Julie R. L. Cason, Veronika Zelenay Givaudan Schweiz AG, 8600 Dübendorf, Switzerland.
*Corresponding Author: Robin Clery, Givaudan Schweiz AG, Ueberlandstrasse 138, CH-8600, Duebendorf, Switzerland. tel: +41 44 824 2424, email: [email protected]
Supporting Information Page 1
Contents
Table S1.
13
Table S2.
1
C-NMR Spectral Data (in C6D6) for compounds 1-8
H-NMR Data(in C6D6) for compounds 1-8
Figure S1 HSCQ and NOESY spectra with annotated structures for compounds 1-8
Supporting Information Page 2
Table S1.
13
C-NMR Data (in C6D6) for compounds 1-8 δC
Position 1
2
3
4
5
6
7
8
Kim et al.a (CDCl3)
1
137.7
137.3
135.1
137.7
66.0
55.1
50.6
67.5
65.0
2
131.6
135.8
133.3
131.7
26.1
31.1
33.9
26.3
27.2
3
120.3
120.5
120.5
120.2
42.6
124.6
169.1
42.9
42.3
4
154.8
154.8
155.9
154.3
130.5
143.4
142.1
132.2
137.0
5
161.2
159.7
159.3
161.4
140.4
69.7
115.1
146.0
144.2
6
44.7
44.4
41.3
40.1
26.4
74.7
30.0
72.6
68.7
7
44.8
44.6
54.7
48.2
64.9
37.1
44.0
58.6
53.6
8
37.6
31.4
31.1
32.9
210.8
25.7
27.0
26.6
21.8
9
36.8
33.4
127.0
36.5
44.0
49.4
27.7
28.9
29.2
10
35.3
37.8
133.3
35.2
36.4
42.3
35.9
35.1
35.4
11
151.4
150.9
149.3
92.5
43.1
37.8
43.9
40.7
41.1
12
20.8
20.8
109.7
27.4
25.1
16.4
26.3
27.2
26.1
13
108.9
109.0
21.3
26.3
20.0
25.7
18.6
20.2
20.4
14
20.6
18.4
22.2
20.6
17.4
26.2
17.9
18.0
18.1
15
24.1
24.0
24.4
23.9
14.1
27.6
15.6
14.6
14.2
a)
Kim, S. J.,et al, New patchoulane-type sesquiterpenes from the rhizomes of Cyperus rotundus. Bull. Korean Chem. Soc. 2012, 33, 3115-3118.
Table S2.
1
H-NMR Data(in C6D6) for compounds 1-8 δH (J in Hz)
Pos 1
2
3
4
5
1
6
7
8
2.03 dd (9.8, 6.8)
2
7.11 d (7.9)
6.96 d (7.7)
7.11d (7.9)
7.1 d (7.9)
1.24 ddd (13.2, 7.9, 1.1)
2.26-2.14 m
3
6.72 d (7.9)
6.63 d (7.7)
6.70 d (7.5)
6.7 d (7.9)
2.02-1.97 m
5.2-5.18 m
6
3.41 br d (13.2)
3.41 br d (14.3)
3.16 dd (11.7, 6.4)
3.53 d (13.2)
2.59-2.53 m
2.24dd (16.2, 9.4)
3.07 dd (12.8, 10.9)
3.27 dd (14.3, 9.8)
3.03 dd (11.7, 7.5)
2.73 dd (13.2,9.4)
2.14 dd (16.2, 10.5)
2.62 dtquint (16.2, 7.9, 1.5)
7
2.09 br t (11.3)
2.19 br t (10.0)
3.08 quint (6.8)
1.32-1.28 m
1.69-1.65 m
1.16 dd (13.2, 6.4) 1.56-1.47 m
2.03 dd (15.8, 6.8)
4.28 br s
8
1.84-1.80 m
1.83-1.76 m
2.02-1.97 m
1.96-1.90 m
2.46 d (6.4)
1.56-1.47 m
1.40-1.38 m
1.63 t (3.4)
1.60 qd (12.8, 3.4)
1.64-1.60 m
1.95-1.90 m
1.32-1.28 m
1.68-1.62 m
1.02-0.98 m
1.36-1.30 m
1.55 dt (12.8, 3.8)
1.59-1.55 m
5.84 tq (7.2, 1.5)
1.64-1.60 m
1.60-1.58 m
1.56-1.47 m
1.73-1.68 m
9
1.16-1.09 m 10
2.64 br dq (9.8, 7.2)
2.72-2.66 m
2.11 s
1.79-1.75 m 1.40 ddd (12.8, 7.9, 0.75)
1.1-1.04 m
2.17 dd (16.2, 6.8)
1.13-1.07 m
1.36-1.30 m
2.67-2.62 m
1.75 ddd (16.6, 10.9, 1.5)
0.91-0.84 m
0.84-0.77 m
11
1.44-1.41 m 2.31 d (11.7)
12
1.68 s
1.73 s
1.70 s
1.12 s
1.87 dquint (10.9, 6.8)
1.85-1.84 m
1.56-1.47 m
1.84-1.79 m
13
4.80 s
4.82 s
5.03 s
1.04 s
0.66 s
1.00 s
0.46 s
1.08 s
4.77-4.75 m
4.75 br s
4.77 quint (1.5)
0.64 s
0.87 s
14
1.08 d (6.8)
1.12 d (7.2)
1.88 s
1.09 d (7.2)
0.74 d (6.4)
0.98 s
0.8 d (6.8)
0.81 d (6.4)
15
2.49 s
2.45 s
2.48 s
2.48 s
1.46 s
0.94 s
1.62 s
1.81 q (1.1)
0.78 s
Supporting Information Page 4
Figure S1 HSCQ and NOESY spectra for Compounds 1-8 HSQC Compound (1)
NOESY Compound (1)
HSQC Compound (2)
NOESY Compound (2)
Supporting Information Page 6
HSQC Compound (3)
NOESY Compound (3)
Supporting Information Page 7
HSQC Compound (4)
NOESY Compound (4)
Supporting Information Page 8
HSQC Compound (5)
NOESY Compound (5)
Supporting Information Page 9
HSQC Compound (6)
NOESY Compound (6)
Supporting Information Page 10
HSQC Compound (7)
NOESY Compound (7)
Supporting Information Page 11
HSQC Compound (8)
NOESY Compound (8)
Supporting Information Page 12
Constituents of Cypriol Oil (Cyperus scariosus R.Br.): N-Containing Molecules and Key Aroma Components. Robin A. Clery,* Julie R. L. Cason, Veronika Zelenay Givaudan Schweiz AG, 8600 Dübendorf, Switzerland.
*Corresponding Author: Robin Clery, Givaudan Schweiz AG, Ueberlandstrasse 138, CH-8600, Duebendorf, Switzerland. tel: +41 44 824 2424, email: [email protected]
Supporting Information Page 1
Contents
Table S1.
13
Table S2.
1
C-NMR Spectral Data (in C6D6) for compounds 1-8
H-NMR Data(in C6D6) for compounds 1-8
Figure S1 HSCQ and NOESY spectra with annotated structures for compounds 1-8
Supporting Information Page 2
Table S1.
13
C-NMR Data (in C6D6) for compounds 1-8 δC
Position 1
2
3
4
5
6
7
8
Kim et al.a (CDCl3)
1
137.7
137.3
135.1
137.7
66.0
55.1
50.6
67.5
65.0
2
131.6
135.8
133.3
131.7
26.1
31.1
33.9
26.3
27.2
3
120.3
120.5
120.5
120.2
42.6
124.6
169.1
42.9
42.3
4
154.8
154.8
155.9
154.3
130.5
143.4
142.1
132.2
137.0
5
161.2
159.7
159.3
161.4
140.4
69.7
115.1
146.0
144.2
6
44.7
44.4
41.3
40.1
26.4
74.7
30.0
72.6
68.7
7
44.8
44.6
54.7
48.2
64.9
37.1
44.0
58.6
53.6
8
37.6
31.4
31.1
32.9
210.8
25.7
27.0
26.6
21.8
9
36.8
33.4
127.0
36.5
44.0
49.4
27.7
28.9
29.2
10
35.3
37.8
133.3
35.2
36.4
42.3
35.9
35.1
35.4
11
151.4
150.9
149.3
92.5
43.1
37.8
43.9
40.7
41.1
12
20.8
20.8
109.7
27.4
25.1
16.4
26.3
27.2
26.1
13
108.9
109.0
21.3
26.3
20.0
25.7
18.6
20.2
20.4
14
20.6
18.4
22.2
20.6
17.4
26.2
17.9
18.0
18.1
15
24.1
24.0
24.4
23.9
14.1
27.6
15.6
14.6
14.2
a)
Kim, S. J.,et al, New patchoulane-type sesquiterpenes from the rhizomes of Cyperus rotundus. Bull. Korean Chem. Soc. 2012, 33, 3115-3118.
Table S2.
1
H-NMR Data(in C6D6) for compounds 1-8 δH (J in Hz)
Pos 1
2
3
4
5
1
6
7
8
2.03 dd (9.8, 6.8)
2
7.11 d (7.9)
6.96 d (7.7)
7.11d (7.9)
7.1 d (7.9)
1.24 ddd (13.2, 7.9, 1.1)
2.26-2.14 m
3
6.72 d (7.9)
6.63 d (7.7)
6.70 d (7.5)
6.7 d (7.9)
2.02-1.97 m
5.2-5.18 m
6
3.41 br d (13.2)
3.41 br d (14.3)
3.16 dd (11.7, 6.4)
3.53 d (13.2)
2.59-2.53 m
2.24dd (16.2, 9.4)
3.07 dd (12.8, 10.9)
3.27 dd (14.3, 9.8)
3.03 dd (11.7, 7.5)
2.73 dd (13.2,9.4)
2.14 dd (16.2, 10.5)
2.62 dtquint (16.2, 7.9, 1.5)
7
2.09 br t (11.3)
2.19 br t (10.0)
3.08 quint (6.8)
1.32-1.28 m
1.69-1.65 m
1.16 dd (13.2, 6.4) 1.56-1.47 m
2.03 dd (15.8, 6.8)
4.28 br s
8
1.84-1.80 m
1.83-1.76 m
2.02-1.97 m
1.96-1.90 m
2.46 d (6.4)
1.56-1.47 m
1.40-1.38 m
1.63 t (3.4)
1.60 qd (12.8, 3.4)
1.64-1.60 m
1.95-1.90 m
1.32-1.28 m
1.68-1.62 m
1.02-0.98 m
1.36-1.30 m
1.55 dt (12.8, 3.8)
1.59-1.55 m
5.84 tq (7.2, 1.5)
1.64-1.60 m
1.60-1.58 m
1.56-1.47 m
1.73-1.68 m
9
1.16-1.09 m 10
2.64 br dq (9.8, 7.2)
2.72-2.66 m
2.11 s
1.79-1.75 m 1.40 ddd (12.8, 7.9, 0.75)
1.1-1.04 m
2.17 dd (16.2, 6.8)
1.13-1.07 m
1.36-1.30 m
2.67-2.62 m
1.75 ddd (16.6, 10.9, 1.5)
0.91-0.84 m
0.84-0.77 m
11
1.44-1.41 m 2.31 d (11.7)
12
1.68 s
1.73 s
1.70 s
1.12 s
1.87 dquint (10.9, 6.8)
1.85-1.84 m
1.56-1.47 m
1.84-1.79 m
13
4.80 s
4.82 s
5.03 s
1.04 s
0.66 s
1.00 s
0.46 s
1.08 s
4.77-4.75 m
4.75 br s
4.77 quint (1.5)
0.64 s
0.87 s
14
1.08 d (6.8)
1.12 d (7.2)
1.88 s
1.09 d (7.2)
0.74 d (6.4)
0.98 s
0.8 d (6.8)
0.81 d (6.4)
15
2.49 s
2.45 s
2.48 s
2.48 s
1.46 s
0.94 s
1.62 s
1.81 q (1.1)
0.78 s
Supporting Information Page 4
Figure S1 HSCQ and NOESY spectra for Compounds 1-8 HSQC Compound (1)
NOESY Compound (1)
HSQC Compound (2)
NOESY Compound (2)
Supporting Information Page 6
HSQC Compound (3)
NOESY Compound (3)
Supporting Information Page 7
HSQC Compound (4)
NOESY Compound (4)
Supporting Information Page 8
HSQC Compound (5)
NOESY Compound (5)
Supporting Information Page 9
HSQC Compound (6)
NOESY Compound (6)
Supporting Information Page 10
HSQC Compound (7)
NOESY Compound (7)
Supporting Information Page 11
HSQC Compound (8)
NOESY Compound (8)
Supporting Information Page 12
