D.V. Kuklev, W.L. Smith / Chemistry and Physics of Lipids 144 (2006) 172–177
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(2 × 150 ml) and then a saturated solution of NaCl and
dried over Na2SO4. The dry extract was filtered and
evaporated under vacuum to yield 889 mg (93%) of
8Z,11Z,14Z,17Z-eicosatetraenoic acid. TLC: Rf (sol-
vent system A) 0.6 (6b).
6H, H-8, 11, 14), 3.40 (t, 2H, H-1), 5.37 (m, 8H, H-6, 7,
9, 10, 12, 13, 15, 16). 13C NMR, CDCl3, δ: 14.58 (C-18),
20.91, 25.92, 26.00, 26.02, 27.37, 28.18, 29.11, 33.09,
34.01 (C-2-5, 8, 11, 14, 17), 127.41, 128.29, 128.45,
128.68, 128.89, 130.16, 132.37 (C-6, 7, 9, 10, 12, 13,
14, 16).
(3c) IR, film (cm−1): 712, 916, 1067, 1251, 1393,
1439, 1658, 2870, 2932, 2962, 3011. 1H NMR, CDCl3,
δ: 0.98 (t, 3H, H-20), 1.52 (m, 2H, H-3), 1.87 (m, 2H,
H-2), 2.08 (m, H-4, 19), 2.83 (m, 8H, H-9, 12, 15, 18),
3.41 (t, 2H, H-1), 5.38 (m, 10H, H-5, 6, 8, 9, 11, 12, 14,
15, 17, 18). 13C NMR, CDCl3, δ: 14.58 (C-20), 20.91,
25.92, 26.01, 26.68, 28.45, 32.68, 33.90(C-2-4, 7, 10, 13,
16, 19), 127.39, 128.23, 128.46, 128.48, 128.61, 128.62,
128.82, 128.82, 128.94, 129.73, 132.38 (C-5, 6, 8, 9, 11,
12, 14, 15, 17, 18).
2.8. Analytical data for newly synthesized
compounds
(2a) IR, film: 712, 824, 1048, 1456, 2334, 2361, 2853,
2928, 3010, 3337. 1H NMR, CDCl3, δ: 0.98 (t, 3H, H-
18), 1.31 (m, 10H, H-3-7), 1.53 (m, 2H, H-2), 2.08 (m,
4H, H-8, 17), 2.81 (m, 4H, H-11, 14), 3.62 (t, 2H, H-1),
5.36 (m, 6H, H-9, 10, 12, 13, 15, 16). 13C NMR, CDCl3,
δ: 14.52 (C-18); 20.84, 25.85, 25.94, 26.06, 27.53, 29.53,
29.70, 29.79, 29.93, 33.09 (C-2-8, 11, 14, 17), 63.23 (C-
1), 127.46, 128.01, 128.58, 130.61, 132.24 (C-9, 10, 12,
13, 15, 16).
(4a) IR, film (cm−1): 722, 824, 875, 997, 1048, 1194,
1
1276, 1456, 1666, 2361, 2853, 2928, 2962, 3017. H
(2b) IR, film (cm−1): 712, 824, 875, 1051, 1262,
1456, 1558, 1653, 2361, 2860, 2928, 3010, 3337. H
NMR, CDCl3, δ: 0.98 (t, 3H, H-20), 1.26 (s, 6H, 2CH3,
oxazoline ring), 1.28 (m, 12H, H-4-9, 1.61 (m, 2H, H-
3), 2.08 (m, 4H, H-11, H-19), 2.23 (t, 2H, H-2), 2.81 (m,
4H, H-13, 16), 3.89 (s, 2H, CH2 in oxazoline ring), 5.36
(m, 6H, H-11, 12, 14, 15, 17, 18). 13C NMR, CDCl3, δ:
14.5 (C-20), 20.9, 25.9, 26.0, 26.4, 27.6, 28.5, 28.8, 29.5,
29.52, 29.6, 29.8, 29.83, 30.0 (C-2-10, 13, 16, 19), 67.2
and 79.2 (oxazoline ring), 127.5, 128.0, 128.6, 128.64,
130.7, 132.3 (C-11, 12, 14, 15, 17, 18), 166.4 (C-1).
Mass spectrum, EI, m/z (I%): (I > 20%)—55(24), 67(24),
79(33), 113(80), 126(100), 168(20.5), 264(22), 290(30),
304(22), 330(20), [M]+—359(31). Monoisotopic exact
mass, m/z: [M+Na]+ 382.3082 (calculated—382.3080).
(4b) IR, film (cm−1): 684, 824, 997, 1198, 1276,
1
NMR, CDCl3, δ: 0.98 (t, 3H, H-18), 1.39 (m, 4H, H-3,
4), 1.57 (m, 2H, H-2), 2.08 (m, 4H, H-5, 17), 2.82 (m,
6H, H-8, 11, 14), 3.63 (t, 2H, H-1), 5.37 (m, 8H, H-6,
7, 9, 10, 12, 13, 15, 16). 13C NMR, CDCl3, δ: 14.53
(C-18); 20.86, 25.74, 25.87, 25.96, 25.98, 27.51, 29.73,
33.01 (C-2-5, 8, 11, 14, 17); 63.21 (C-1); 127.39, 128.21,
128.29, 128.36, 128.73, 128.84, 130.39, 132.34 (C-6, 7,
9, 10, 12, 13, 15, 16).
(2c)IR, film(cm−1):712, 793, 926, 1068, 1266, 1391,
1452, 1643, 1660, 2928, 3017, 3337. 1H NMR, CDCl3,
δ: 0.977 (t, 3H, H-20), 1.46 (m, 2H, H-3), 1.57 (m, 2H, H-
2), 2.08 (m, 4H, H-4, 19), 2.83 (m, 6H, H-7, 10, 13, 16),
3.64 (t, 2H, H-1), 5.37 (m, 10H, H-5, 6, 8, 9, 11, 12, 14,
15, 17, 18). 13C NMR, CDCl3, δ: 14.49 (C-18), 20.90,
25.96, 26.06, 26.08, 26.11, 26.19, 27.36, 32.81 (C-2, 3,
4, 7, 10, 13, 16, 19), 63.20 (C-1), 127.48, 128.32, 128.45,
128.51, 128.58, 128.66, 128.82, 129.00, 130.30, 132.43
(C-5, 6, 8, 9, 11, 12, 14, 15, 17, 18).
1
1456, 1493, 1668, 2362, 2860, 2940, 3012. H NMR,
CDCl3, δ: 0.97 (t, 3H, H-20), 1.26 (s, 6H, 2CH3, oxazo-
line ring), 1.34 (m, 6H, H-4-6), 1.63 (m, 2H, H-3), 2.08
(m, 4H, H-7, 19), 2.24 (t, 2H, H-2), 2.84 (m, 6H, H-10,
13, 16), 3.89 (s, 2H, CH2 in oxazoline ring), 5.37 (m, 8H,
H-8, 9, 11, 12, 14, 15, 17, 18). 13C NMR, CDCl3, δ: 14.50
(C-20), 20.82, 25.83, 25.91, 25.92, 26.31, 27.45, 28.70,
29.15, 29.33, 29.73, 31.08 (C-2-7, 10, 13, 16, 19), 67.12
and 79.17 (oxazoline ring), 127.35, 127.99, 128.25,
128.73, 128.76, 130.52, 132.25 (C-8, 9, 11, 12, 14, 15,
17, 18), 166.28 (C-1). Mass spectrum, EI, m/z (I%):
55(36), 67(25), 79(30), 113(48), 126(100), 248(20),
262(21), 288(28), [M]+—357(29). Monoisotopic exact
mass, m/z: [M+Na]+ 380.2923 (calculated—380.2924).
(4c) IR, film (cm−1): 684, 824, 997, 1198, 1276,
(3a) IR, film (cm−1): 722, 824, 878, 912, 1051, 1068,
1269, 1395, 1435, 1456, 1558, 1653, 2334, 2361, 2853,
1
2928, 3010. H NMR, CDCl3, δ: 0.98 (t, 3H, H-18),
1.3 (m, 8H, H-3-6), 1.42 (m, 2H, H-7), 1.85 (m, 2H,
H-2), 2.08 (m, 4H, H-8, 17), 2.81 (m, 4H, H-11, 14),
3.40 (t, 2H, H-1), 5.36 (m, 6H, H-9, 10, 12, 13, 15, 16).
13C NMR, CDCl3, δ: 14.57 (C-18), 20.90, 25.90, 25.99,
27.56, 28.52, 29.08, 29.51, 29.66, 29.93, 33.20, 34.15
(C-2-8, 11, 14, 17), 127.50, 128.12, 128.61, 128.65,
130.60, 132.29 (C-9, 10, 12, 13, 15, 16).
1
1456, 1493, 1668, 2361, 2860, 2940, 3012. H NMR,
(3b) IR, film (cm−1): 715, 824, 912, 1048, 1266,
1395, 1456, 1653, 2334, 2361, 2860, 2928, 3010. H
NMR, CDCl3, δ: 0.98 (t, 3H, H-18), 1.43 (m, 4H, H-3,
4), 1.87 (m, 2H, H-2), 2.08 (m, 4H, H-5, 17), 2.82 (m,
CDCl3, δ: 0.97 (t, 3H, H-22), 1.26 (s, 6H, 2CH3, oxa-
zoline ring), 1.37 (m, 4H, H-4, 5), 1.63 (m, 2H, H-
3), 2.08 (m, 4H, H-6, 21), 2.24(t, 2H, H-2), 2.85 (m,
8H, H-9, 12, 15, 18), 3.89 (s, 2H, CH2 in oxazoline
1