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. Author manuscript; available in PMC: 2010 Jul 12.
Published in final edited form as: Zoolog Sci. 2010 Jul;27(7):565–573. doi: 10.2108/zsj.27.565

Table 1.

Complete 1H and 13C chemical shifts of the isolated taurine conjugates of (25R)/ (25S)-THCAs.a

Compound C (25S) Compound D (25R) Difference in the chemical shifts
between C and D
Carbon no. Type 13C 1H
 Type 13C 1H
 13C 1H
α β α β α β
1 CH2 36.52 1.80 0.96 CH2 36.52 1.79 0.96 0.00 0.01 0.00
2 CH2 31.21 1.42 1.58 CH2 31.20 1.41 1.58 0.01 0.01 0.00
3 CH 72.93 3.35 (brm) CH 72.92 3.35 (brm) 0.01 0.00
4 CH2 40.50 2.26 1.64 CH2 40.50 2.26 1.64 0.00 0.00 0.00
5 CH 43.25 1.36 CH 43.24 1.36 0.01 0.00
6 CH2 35.83b 1.50 1.94 CH2 35.81b 1.50 1.94 0.02 0.00 0.00
7 CH 69.10 3.78 (m) CH 69.11 3.78 (m) −0.01 0.00
8 CH 41.07 1.54 CH 41.08 1.54 −0.01 0.00
9 CH 27.89 2.24 CH 27.87 2.24 0.02 0.00
10 C 35.92 C 35.92 0.00
11 CH2 29.57 1.56 1.56 CH2 29.57 1.56 1.56 0.00 0.00 0.00
12 CH 74.05 3.94 (m) CH 74.09 3.94 (m) −0.04 0.00
13 C 47.47 C 47.47 0.00
14 CH 42.97 1.96 CH 42.95 1.95 0.02 0.01 0.00
15 CH2 24.24 1.72 1.09 CH2 24.22 1.73 1.09 0.02 −0.01 0.00
16 CH2 28.86 1.86 1.26 CH2 28.82 1.86 1.26 0.04 0.00 0.00
17 CH 48.34 1.84 CH 48.30 1.82 0.04 0.02
18 CH3 12.99 0.70 (s) CH3 13.00 0.70 (s) −0.01 0.00
19 CH3 23.16 0.91 (s) CH3 23.16 0.91 (s) 0.00 0.00
20 CH 37.15 1.38 CH 37.12 1.38 0.03 0.00
21 CH3 18.04 0.98 (d, 6.6) CH3 18.08 0.98 (d, 6.6) −0.04 0.00
22 CH2 37.05 1.06, 1.38 CH2 37.08 1.04, 1.38 −0.03 0.02, 0.00
23 CH2 25.18 1.38 CH2 25.07 1.20, 1.34 0.11 0.04
24 CH2 35.80b 1.26, 1.52 CH2 35.78b 1.34, 1.52 0.02 −0.08, 0.00
25 CH 42.33 2.24 CH 42.35 2.26 −0.02 −0.02
26 CH3 18.31 1.08 (d, 6.6) CH3 18.08 1.08 (d, 6.6) 0.23 0.00
27 C 179.40 C 179.50 −0.10
28 CH2 36.49 3.58 (t, 7.2) CH2 36.48 3.58, 3.59 (each t, 7.2) 0.01 0.00, −0.01
29 CH2 51.58 2.95, 2.96 (each t, 7.2) CH2 51.59 2.95 (t, 6.9), 2.96 (t, 7.2) −0.01 0.00, 0.00
a

Measured in CD3OD at 600 MHz in 1H-NMR and at 149.4 MHz in 13C-NMR; chemical shifts were expressed as δ ppm relative to Me4Si; abbreviations used: s, singlet; d, doublet; m, multiplet; brm, broad multiplet; t, triplet; values in parentheses refer to signal multiplicity and coupling constant (J in Hz).

b

Assignment down a vertical column may be interchanged.