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Saturday 20 December 2014

3,5-diprenyl-4-hydroxycinnamic acid, or Artepillin C



One- and two-dimensional NMR analyses carried out in CD3OD confirmed this result, since the data obtained were consistent with the structure of 3,5-diprenyl-4-hydroxycinnamic acid, also known as artepillin C (Figure 1): 1H NMR (500 MHz, CD3OD): 7.14 (1H, s, H-2), 7.53 (1H, d, J=16.0 Hz, H-7), 6.19 (1H, d, J=16.0 Hz, H-8), 3.32 (2H, br.d, J=7.3 Hz, H-1' and 1''), 5.32 (2H, br.t, J=7.3 Hz, H-2' and 2''), 1.76 (2H, s, H-4' and 4''), 1.72 (2H, s, H-5' and 5''). 13C NMR (125 MHz, CD3OD): 127.5 (C-1), 128.4 (C-2 and 6), 130.2 (C-3 and 5), 156.3 (C-4), 147.2 (C-7), 115.4 (C-8), 171.2 (C-9), 29.5 (C-1' and 1''), 123.3 (C-2' and 2''), 134.0 (C-3' and 3''), 25.9 (C-4' and 4''), 17.9 (C-5' and 5''). Since no NMR spectrum of artepillin C dissolved in CD3OD was found in the literature, 1H NMR (400 MHz) analysis was also carried out in CDCl3 and the spectrum obtained was in complete agreement with data given in the literature (AGA et al., 1994; PARK et al., 2004). 


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1 comment:

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