Thesis-Final 03 June 2011 pdf - Jacobs University

Annex Chapter 6
5-O-caffeoylquinic acid, (69)-p104
5-diacetyl caffeoyl-bisacetonide 64 (0.100 g, 0.192 mmol) in a mixture of degassed
THF (5 ml) and 2M HCl (10 ml) was stirred for 24 hours at room temperature. The
solvent was removed under reduced pressure to give the title compound 69 as a
yellowish powder (0.047 g, 69%). Rf 0.65 [chloroform: acetone (8:2)];
(KBr)/cm -1 : 3425 (OH), 1773 (C=O), 1653 (C Ar =C Ar ), 1213, 1050, 1026 (C-O); δ H
(400 MHz, DMSO): 1.67 (1 H, dd, J 12.82 and 2.3, 6-H ax ), 1.73 (1 H, dd, J 14.9 and
3.2, 2-H ax ), 1.83 (1 H, ddd, J 13.5, 4.6 and 3.2, 6-H eq ), 1.87 (1 H, dt, J 14.9 and 3.2, 2-
H eq ), 3.19 (1 H, dd, J 8.7 and 2.8, 4-H), 3.72 (1 H, ddd, J 12.4, 8.3 and 4.2, 3-H), 3.84
(1 H, q, J 5.7, 5-H), 6.10 (1 H, d, J 15.9, 9-H), 6.73 (1 H, d, J 8.2, 12-H), 6.91 (1 H, d,
J 8.2, 15-H), 6.94 (1 H, s, 16-H), 7.36 (1 H, d, J 16, 10-H); δ C (125 MHz, DMSO):
35.61 (C-6), 37.83 (C-2), 68.74 (C-3), 69.57 (C-5), 71.66 (C-4), 79.69 (C-1), 115.72
(C-9), 122.61 (C-12), 122.93 (C-15), 123.15 (C-16), 132.82 (C-11), 142.47 (C-13),
145.23 (C-14), 166.85 (C-8), 177.37 (C-7).
ν max
210