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Table 1 1 H and 13 C NMR spectroscopic data of compound 5 (600 MHz, δ in ppm)

From: 2,3-cis-2R,3R-(−)-epiafzelechin-3-O-p-coumarate, a novel flavan-3-ol isolated from Fallopia convolvulus seed, is an estrogen receptor agonist in human cell lines

Atom # 1H   13C
2 5.07 (s) 76.3
3 5.34 (m) 67.8
2.65 (dd, J = 17.6, 2.4 Hz) 25.6
2.92 (dd, J = 17.6, 4.9 Hz) 25.6
4a    97.2
5    156.6*
6 5.94 (d, J = 2.4 Hz) 95.6
7    156.5*
8 5.79 (d, J = 2.4 Hz) 94.3
8a    155.5
1'    128.6
2',6' 7.25 (d, J = 8.6 Hz) 127.8
3',5' 6.7 (d, J = 8.6 Hz) 114.8
4'    156.9
C = O    166.1
α 6.25 (d, J = 15.8 Hz) 113.6
β 7.38 (d, J = 15.8 Hz) 145.3
1"    124.6
2",6" 7.5 (d, J = 8.6 Hz) 130.5
3",5" 6.72 (d, J = 8.6 Hz) 115.8
4"    160.3
  1. Compound was measured in DMSO. Chemical shifts are reported relative to TMS (residual dimethylsulphoxide-D6 = 2.50 ppm for 1H and 39.51 ppm for 13C). *Chemical shift assignment for C5 and C7 may be reversed. HMBC data did not permit resolution sufficient to unambiguously assign the two resonances. This finding has no impact on the proposed structure. A single broad –OH resonance was observed at 9.9 ppm.