Synthesis of N,N,N-Trimethylhexadecan-1-aminium
(Z)-12-Hydroxyoctadec-9-enoate (CTB-RA)
Quantities of substrates taken: Sodium ricinoelate (1g, 0.0031 mol),
CTA-Br (1g, 0.0027 mol), yield obtained 88% (1.54 g).1H NMR (CDCl3, ppm):δ 5.53 (m,
-CH=CH-), 5.37 (m, -CH=CH-), 3.60 (m, 1H, -CHOH), 3.39 (t,
2H,-CH2N), 3.32 (s, 9H, -CH3), 2.48 (t,
2H, -H2CCOO), 2.15 (m, 2H, -CH2-C=C-),
2.02 (t, 2H, -CH2-C=C-), 1.72 (m, 8H,
4xCH2), 1.55 (m, 2H, -CH2), 1.44 (m, 2H,
-CH2), 1.34 (m, 4H, 2xCH2), 1.26 (m,
36H, 18x-CH2), 0.88 (t, 3H, -CH3).13C NMR (CDCl3, ppm): δ 180.4, 133.0,
125.5, 71.2, 66.9, 53.4, 37.6, 35.6, 31.8, 29.7, 25.1, 22.5, 14.1. IR
(CHCl3, cm-1): 3356, 3008, 2924, 2853,
1760, 1556, 1463, 1218, 773.