Article
J. Agric. Food Chem., Vol. 58, No. 3, 2010 1825
2E-C7:1-OH: yield, 84.6%; GC-MS, m/z (%) 114 (Mþ, 1.5), 96 (Mþ
-
J = 7.5 Hz), 2.34 (2H, ddt, J1 = 7.5 Hz, J2 = 7.0 Hz, J3 = 1.5 Hz), 6.12
(1H, ddt, J1 = 15.5 Hz, J2 = 7.0 Hz, J3 = 1.5 Hz), 6.86 (1H, dt, J1 = 15.5
Hz, J2 = 7.0 Hz), 9.15 (1H, d, J = 7 Hz); 13C NMR, δ 194.1 (dCHO),
159.0 (dCH), 133.0 (dCH), 32.7 (CH2), 31.7 (CH2), 29.1 (CH2), 29.0
(CH2), 27.9 (CH2), 22.6 (CH2), 14.1 (CH3); IR (cm-1, neat), 2930-2858
(s), 1697 (s), 1634 (w), 1468 (m), 1146 (m), 1105 (m), 976 (s).
H2O, 14.6), 81 (28.6), 71 (13.4), 68 (19.2), 67 (11.3), 57 (100), 41 (40); 1H
NMR, δ 0.89 (3H, t, J1 = 7 Hz, 7-H3), 1.35 [1.28-1.38] (4H, m, 5-, 6-H2),
1.79 (1H, br s, -OH), 2.05 (2H, m, 4-H2), 4.07 (2H, dt, J1 = 6 Hz, J2 = 6
Hz, 1-H2), 5.66 [5.72-5.60] (2H, br m, 2-, 3-H, dCH-); 13C NMR, δ 14.0
(CH3, C7), 22.8 (CH2, C6), 31.5 (CH2, C5), 32.0 (CH2, C4), 63.9 (CH2,
C1), 129.0 (dCH, C2), 133.6 (dCH, C3); IR (cm-1, neat), 3352-3090 (s),
2960-2873 (s), 1672 (w), 1468 (m), 1092 (m), 1011 (s), 970 (s).
2E-C11:1-al: yield, 88.5%; GC-MS, m/z (%) 150 (Mþ - H2O), 135
(4.1), 124 (11.0), 121 (19.5), 111 (15.2), 97 (25.8), 83 (70.4), 70 (100), 69
(51.3), 57 (70.9), 55 (66.4), 41 (63.0); 1H NMR, δ 0.89 (3H, t, J = 7 Hz),
1.20 -1.38 [1.28] (10H, s-like), 1.50 (2H, pentuplet, J = 7 Hz), 2.34 (2H,
ddt, J1 = 7 Hz, J2 = 7 Hz, J3 = 1.5 Hz), 6.13 (1H, ddt, J1 = 15.5 Hz, J2 =
7 Hz, J3 = 1.5 Hz), 6.86 (1H, dt, J1 = 15.5 Hz, J2 = 7 Hz), 9.15 (1H, d,
J = 7 Hz); 13C NMR, δ 14.09 (CH3), 22.67 (CH2), 27.87 (CH2), 29.18
(CH2), 29.21 (CH2), 29.34 (CH2), 31.85 (CH2), 32.78 (CH2), 134.02
(dCH), 159.25 (dCH), 194.32 (-CHO); IR (cm-1, neat), 2931-2858
(s), 1697 (s), 1639 (w), 1468 (m), 1146 (m), 1105 (m), 976 (s).
2E-C8:1-OH: yield, 84.4%; GC-MS, m/z (%) 128 (Mþ, 0.8), 110 (Mþ
-
H2O, 7.2), 95 (10.4), 81 (25.5), 68 (26.6), 57 (100), 55 (38.1), 43 (31.0); 1H
NMR, δ 0.89 (3H, t, J = 7 Hz, 8-H3), 1.30 [1.20-1.34] (4H, m, 6,7-H2),
1.38 (2H, quin, J = 7 Hz, 5-H2), 1.88 (1H, br s, -OH), 2.04 (2H, ddt, J1 =
7 Hz, J2 = 6.5, J3 = 1 Hz, 4-H2), 4.07 (2H, dd, J1 = 7 Hz, J2 = 1 Hz,
1-H2), 5.66 [5.60-5.72] (2H, br m, 2-, 3-H, dCH-); 13C NMR, δ 14.0
(CH3, C8), 22.5 (CH2, C7), 28.9 (CH2, C5), 31.4 (CH2, C6), 32.2 (CH2,
C4), 63.7 (CH2, C1), 128.9 (dCH, C2), 133.5 (dCH, C3); IR (cm-1, neat),
3597-3086 (br s), 2960-2860 (s), 1672 (w), 1468 (m), 1092 (m), 1005 (s),
972 (s).
2E-C12:1-al: yield, 91.9%; GC-MS, m/z (%) 182 (Mþ, 0.5), 164 (1.6),
138 (9.4), 121 (20.0), 111 (17.9), 97 (40.6), 83 (78.0), 70 (100), 69 (47.3), 55
(66.3), 43 (54.4); 1H NMR, δ 0.88 (3H, t, J = 7 Hz), 1.20 -1.38 [1.25]
(12H, m), 1.51 (2H, pentuplet, J = 7 Hz), 2.33 (2H, ddt, J1 = 7.5 Hz, J2 =
7 Hz, J3 = 1.5 Hz), 6.11 (1H, ddt, J1 = 15.5 Hz, J2 = 8 Hz, J3 = 1.5 Hz),
6.86 (1H, dt, J1 = 15.5 Hz, J2 = 7.5 Hz), 9.47 (1H, d, J = 8 Hz); 13C
NMR, δ 14.11 (CH3), 22.64 (CH2), 28.03 (CH2), 29.32 (CH2), 29.45 (CH2),
29.54 (CH2), 29.65 (CH2), 32.04 (CH2), 32.99 (CH2), 133.00 (dCH),
159.02 (dCH), 194.07 (-CHO); IR (cm-1, neat), 2937-2858 (s), 1699 (s),
1670 (w), 1468 (m), 1147 (m), 1105 (m), 978 (s).
2E-C9:1-OH: yield, 75.7%; GC-MS, m/z (%) 142 (Mþ, 0.4), 124 (Mþ
-
H2O, 3.3), 109 (2.7), 95 (25.5), 82 (30.8), 70 (17.3), 68 (26.9), 67 (23.6), 57
(100), 41 (45.9); 1H NMR, δ 0.89 (3H, t, J = 7 Hz, 9-H3), 1.30 [1.20-1.34]
(6H, m, 6-, 7-, 8-H2), 1.38 (2H, m, 5-H2), 1.80 (1H, br s, -OH), 2.04 (2H,
dt, J1 = 7 Hz, J1 = 7 Hz, 4-H2), 4.07 (2H, dd, J1 = 5.5 Hz, J2 = 1 Hz, 1-
H2), 5.66 [5.72-5.60] (2H, br m, 2,3-H, dCH-); 13C NMR, δ 14.2 (CH3,
C9), 22.8 (CH2, C8), 29.0 (CH2, C6), 29.3 (CH2, C5), 31.9 (CH2, C7), 32.4
(CH2, C4), 63.9 (CH2, C1), 129.0 (dCH, C2), 133.6 (dCH, C3); IR (cm-1
,
2E-C13:1-al: yield, 90.2%; GC-MS, m/z (%) 196 (Mþ, 0.8), 181 (0.4),
165 (1.9), 152 (6.0), 135 (9.6), 121 (15.3), 111 (22.1), 97 (41.0), 83 (77.7), 70
(100), 69 (43.7), 55 (66.0), 41 (59.2); 1H NMR, δ 0.86 (3H, t, J = 7 Hz),
1.25 [1.20-1.38] (16H, m), 1.49 (2H, pentuplet, J = 7 Hz), 2.34 (2H, q-like,
J = 7.5 Hz), 6.09 (1H, ddt, J1 = 15.5 Hz, J2 = 7.5 Hz, J3 = 1.5 Hz), 6.84
(1H, dt, J1 = 15.5 Hz, J2 = 7.5 Hz), 9.48 (1H, d, J = 7.5 Hz); 13C NMR, δ
14.11 (CH3), 22.69 (CH2), 27.87 (CH2), 29.17 (CH2), 29.32 (CH2), 29.37
(CH2), 29.53 (CH2), 29.59 (CH2), 31.91 (CH2), 32.76 (CH2), 132.98
(dCH), 159.14 (dCH), 194.22 (-CHO); IR (cm-1, neat), 2929-2856
(s), 1697 (s), 1639 (w), 1467 (m), 1143 (m), 1106 (m), 977 (m).
neat), 3580-3084 (s), 2960-2858 (s), 1672 (w), 1468 (m), 1092 (m), 1009
(s), 970 (s).
2E-C11:1-OH: yield, 74.1%; bp, 82 °C/5 mmHg; GC-MS, m/z (%) 170
(Mþ, 0.4), 152 (2.4), 137 (0.7), 124 (5.0), 109 (10.3), 95 (25.4), 82 (40.9), 71
(21.5), 69 (29.7), 68 (33.2), 57 (100), 55 (43.8), 43 (43.1), 41 (49.5); 1H
NMR, δ 0.88 (3H, t, J = 7 Hz, 1-H3), 1.27 [1.20-1.35] [10H, m (s-like)],
1.37 (2H, quin, J = 7 Hz), 1.47 (1H, -OH), 2.04 (2H, m, 4-H2), 4.08 (2H,
dd, J1 = 6 Hz, J2 = 1 Hz, 1-H2), 5.66 [5.60-5.72] (2H, m, 2,3-H, dCH-);
13C NMR, δ 14.1 (CH3), 22.7 (CH2), 29.1 (CH2), 29.2 (CH2), 29.3 (CH2),
29.5(CH2), 31.9 (CH2), 32.2 (CH2), 63.8 (-CH2OH), 128.8 (-CdC;
CH2OH), 133.6 (-CH2;CdC-); IR (cm-1, neat), 3602-3086 (s),
2958-2856 (s), 1674 (w), 1468 (m), 1093 (m), 1011 (m), 970 (s).
2E-C12:1-OH: yield, 91.0%; bp, 104 °C/4 mmHg; GC-MS, m/z (%) 184
(Mþ, 0.5), 166 (3.5), 138 (5.9), 123 (6.0), 109 (15.4), 95 (31.8), 82 (58.0), 71
(24.0), 57 (100), 55 (45.0), 43 (44.1); 1H NMR, δ 0.88 (3H, t, J = 7 Hz),
1.27 [1.00-1.34] (12H, s-like), 1.37 (2H, m), 1.91 (1H, br s, -OH), 2.03
(2H, dt, J1 = 7 Hz, J2 = 7 Hz, 4-H2), 4.06 (2H, dd, J1 = 6 Hz, J2 = 1 Hz),
5.65 [5.71-5.59] (2H, br m); 13C NMR, δ 14.30 (CH3), 22.89 (CH2), 29.39
(CH2), 29.42 (CH2), 29.55 (CH2), 29.73 (CH2), 29.80 (CH2), 32.12 (CH2),
32.44 (CH2), 63.72 (CH2), 128.91 (dCH, C2), 133.43 (dCH, C3); IR
(cm-1, neat), 3599-3111 (br s), 2931-2862 (s), 1672 (w), 1468 (m), 1093
(m), 1012 (m), 929 (s).
2E-C14:1-al: yield, 88.4%; GC-MS, m/z (%) 210 (Mþ, 0.7), 192 (1.1),
166 (5.0), 135 (11.9), 121 (18.9), 111 (24.2), 97 (41.9), 83 (79.4), 70 (100), 69
(42.6), 55 (64.5), 41 (59.0); 1H NMR, δ 0.86 (3H, t, J = 7 Hz), 1.25
[1.20-1.38] (16H, m), 1.49 (2H, pentuplet, J = 7 Hz), 2.34 (2H, q-like, J =
7.5 Hz), 6.09 (1H, ddt, J1 = 15.5 Hz, J2 = 7.5 Hz, J3 = 1.5 Hz), 6.84 (1H,
dt, J1 = 15.5 Hz, J2 = 7.5 Hz), 9.48 (1H, d, J = 7.5 Hz); 13C NMR, δ 14.13
(CH3), 22.72 (CH2), 27.90 (CH2), 29.19 (CH2), 29.38 (CH2), 29.40 (CH2),
29.55 (CH2), 29.65 (CH2), 29.66 (CH2), 31.95 (CH2), 32.77 (CH2), 133.00
(dCH), 159.04 (dCH), 194.09 (-CHO); IR (cm-1, neat), 2931-2856 (s),
1697 (s), 1641 (w), 1468 (m), 976 (m).
Tetradecanal: yield, 42.0%; IR (cm-1, neat), 2918-2850 (s), 1707 (s),
1471 (s).
C9-Ac: yield, 82.5%; bp, 104 °C/22 mmHg; GC-MS, 171 (Mþ - CH3,
0.2), 127 (1.4), 126 (13.0), 116 (16.9), 97 (38.9), 83 (37.6), 70 (54.1), 69
(46.1), 56 (56.6), 55 (46.7), 43 (100); IR (cm-1, neat), 2933-2860 (s), 1747
(s), 1470 (m), 1365 (m), 1240 (s), 1041 (s).
C10-Ac: yield, 81.3%; bp, 87-90 °C/3 mmHg; GC-MS, m/z (%) 185
(Mþ - CH3, 0.3), 141 (1.5), 140 (12.7), 112 (30.9), 97 (41.2), 83 (54.3), 70
(62.4), 69 (51.3), 56 (47.9), 55 (51.8), 43 (100); IR (cm-1, neat), 2933-2858
(s), 1747 (s), 1470 (m), 1365 (m), 1240 (s), 1047 (s).
C11-Ac: yield, 63.8%; bp, 120 °C/22 mmHg; GC-MS, m/z (%) 199
(Mþ - CH3, 0.2), 155 (1.3), 154 (9.6), 126 (21.5), 111 (22.6), 97 (47.4), 83
(53.3), 70 (53.0), 69 (56.7), 56 (45.8), 55 (51.6), 43 (100); IR (cm-1, neat),
2933-2858 (s), 1745 (s), 1470 (m), 1365 (m), 1244 (s), 1043 (s).
C14-Ac: yield, 72.1%; bp, 130-132 °C/1 mmHg; GC-MS, m/z (%) 256
(Mþ, 0.1), 241 (0.4), 196 (10.5), 168 (16.8), 140 (6.3), 125 (18.7), 111 (41.7),
97 (75.2), 83 (87.0), 69 (69.8), 55 (60.5), 43 (100); IR (cm-1, neat),
2935-2858 (s), 1747 (s), 1468 (m), 1365 (m), 1246 (s), 1043 (s).
Nematicidal Activity. Solutions of aliphatic compounds were pre-
pared by serial dilution with distilled water containing Triton X-100 (5 mg/
mL). Test solutions were introduced into wells of 96-well plates (Falcon,
USA). In each well, the concentration of nematodes was about 50-150
nematodes (mixtures of juvenile and adult nematodes, male/female/
juvenile ≈ 1:1:2) per 100 μL of water. Controls received distilled water-
Triton X-100 solutions. Treated and control nematodes were held under
2E-C13:1-OH: yield, 75.6%; bp, 108 °C/3 mmHg; GC-MS, m/z (%) 180
(Mþ - H2O, 4.7), 152 (4.0), 123 (7.3), 95 (25.3), 82 (54.7), 71 (29.3), 68
(38.6), 57 (100), 43 (48.8); 1H NMR, δ 0.88 (3H, t, J = 7 Hz), 1.26
[1.00-1.34] (14H, s-like), 1.36 (2H, m), 1.51 (1H, br s, -OH), 2.03 (2H, dt,
J = 7 Hz, 7, 4-H2), 4.06 (2H, dd, J1 = 6 Hz, J2 = 1 Hz), 5.65 [5.71-5.59]
(2H, br m); 13C NMR, δ 14.30 (CH3), 22.89 (CH2), 29.17 (CH2), 29.22
(CH2), 29.36 (CH2), 29.53 (CH2), 29.64 (CH2), 29.65 (CH2), 31.93 (CH2),
32.24 (CH2), 63.83 (CH2), 128.85 (dCH, C2), 133.58 (dCH, C3); IR
(cm-1, neat), 3540-3111 (br s), 2931-2856 (s), 1674 (w), 1468 (m), 1093
(m), 1011 (m), 970 (m).
2E-C14:1-OH: yield, 79.4%; bp, 116-118 °C/3 mmHg; GC-MS, m/z
(%) 194 (Mþ - H2O, 2.8), 166 (3.4), 151 (176.4), 124 (6.7), 111 (7.3), 109
(16.8), 96 (37.8), 82 (66.4), 71 (25.4), 68 (39.6), 57 (100), 43 (43.8); 1H
NMR, δ 0.88 (3H, t, J1 = 7 Hz, 1-H3), 1.26 [1.20-1.42] [18H, m (s-like)],
2.03 (3H, m, 4-H2, -OH), 4.06 (2H, d-like), 5.66 [5.590-5.71] (2H, m); 13
C
NMR, δ 14.1 (CH3, C-14), 22.7 (CH2), 29.22 (CH2), 29.26 (CH2), 29.40
(CH2), 29.57 (CH2), 29.67 (CH2), 29.69 (CH2), 29.73 (CH2), 32.0 (CH2),
32.3 (CH2), 63.7 (-CH2OH), 128.9 (-CdC;CH2OH), 133.4 (-CH2;
CdC-); IR (cm-1, neat), 3614-3120 (br s), 2943-2866 (s), 1674 (w), 1468
(m), 1095 (m), 1011 (m), 972 (m).
2E-C10:1-al: yield, 70.4%; GC-MS, m/z (%) 154 (Mþ, 0.04), 136 (1.8),
121 (5.3), 110 (11.4), 98 (19.7), 83 (50.2), 70 (86.3), 57(58.7), 55 (100); 1H
NMR, δ 0.89 (3H, t, J = 7.8 Hz), 1.20 -1.38 (8H, m), 1.51 (2H, pentuplet,