from saira fat and flax-seed oil as colorless oily liquids for every 2 g of starting mixture placed on the column.
An analogous procedure was performed using ethyl esters ofα-linolenic, eicosapentaenoic, and docosahexaenoic acids
to afford FA ethanolamides of these FA (R 0.47) as oily liquids in yields of 33, 34, and 35 mg, respectively, for each 100 mg
f
of FA ethyl esters used in the reaction.
All FA ethanolamides from pure FA ethyl esters and from mixtures were analyzed by HPLC-MS (APCI).
Preparation of Trimethylsilyl Derivatives of FA Ethanolamides for MS Analysis. FA ethanolamide (3-10 mg) was
dissolved in a mixture (100 µL, 1:1 by vol) of N,O-bis-(trimethylsilyl)trifluoroacetamide and pyridine held at 60°C for 1 h,
cooled, treated with hexane (1 mL) and saturated NaCl solution (1 mL), vigorously shaken, dried over a small amount of
Na SO (anhydrous), and evaporated under a stream of N . The drysolid was dissolved in hexane (2 mL) and analyzed by MS
2
4
2
using EI ionization.
9Z,12Z,15Z-Octadecatrienoic acid (2-hydroxyethyl)amide (R 0.47, hexane:acetone, 1:1):
f
-1
UV spectrum (MeOH, λ , nm): 208 (log ε 3.68); IRspectrum (KBr, ν, cm ): 3311 (>NH, –OH), 2925 (–CH<), 1714
max
(–CO–NH–R), 1653(>C=C<), 1550 (–CO–NH–R), 1463 (–CH –), 1267 (–CO–NH–R), 1070 (C–O–), 720 (>C=C<, cis-); mass
2
+
spectrum (APCI), m/z (I , %): 322 (91) [M + H] , 304 (100); mass spectrum of trimethylsilyl derivative (EI, 70 eV, m/z, I ,
%): 393 (7) [M] , 378 (33), 303 (5), 175 (52), 154 (23), 134 (46), 118 (71), 73 (100), 69 (91).
rel
rel
+
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoicacid(2-hydroxyethyl)amide(R 0.47, hexane:acetone, 1:1): UVspectrum (MeOH,
f
-1
λ
, nm): 211 (log ε 3.87); IR spectrum (KBr, ν, cm ): 3312 (>NH, –OH), 2925 (–CH<), 1712 (–CO–NH–R), 1653 (>C=C<),
max
1552 (–CO–NH–R), 1466 (–CH –), 1265 (–CO–NH–R), 1072 (C–O–), 718 (>C=C<, cis-); mass spectrum (APCI, m/z, I , %):
2
rel
+
+
346 (87) [M + H] , 328 (100); mass spectrum of trimethylsilyl derivative (EI, 70 eV, m/z, I , %): 417 (4) [M] , 302 (25), 328
rel
(3), 175 (50), 134 (48), 118 (100), 99 (51), 73 (100), 69 (88).
4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoic acid (2-hydroxyethyl)amide (R 0.47, hexane:acetone, 1:1): UV spectrum
f
-1
(MeOH, λ , nm): 215 (log ε 3.91); IR spectrum (KBr, ν, cm ): 3312 (>NH, –OH), 2927 (–CH<), 1714 (–CO–NH–R), 1652
max
(>C=C<), 1552 (–CO–NH–R), 1465 (–CH –), 1265 (–CO–NH–R), 1070 (C–O–), 721 (>C=C<, cis-); mass spectrum (APCI,
2
+
+
m/z, I , %): 372 (88) [M + H] , 364 (100); mass spectrum of trimethylsilyl derivative (EI, 70 eV, m/z, I , %): 443 (4) [M] ,
rel
rel
428 (20), 352 (4), 175 (48), 134 (49), 118 (98), 85 (52), 73 (100), 69 (83).
ACKNOWLEDGMENT
We thank the Scientific-Education Center Marine Biota of the Far-East State University for technical help in carrying
out the structure—analytical research.
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