12-Aminododecanoic acid and 11-aminoundecanoic acid, monomer precursors for nylon-12 and nylon-11, respectively, have been synthesized from vernolic (cis-12,13-epoxy-cis-9-octadecenoic) acid via a reaction sequence that includes the formation of 12-oxododecanoic acid oxime. Saponification of vernonia oil, followed by a low-temperature recrystallization at −20°C, gave 51% vernolic acid (97% purity, m.p. 23-25°C). Hydrogenation afforded cis-12,13-epoxystearic acid (m.p. 52-54°C, lit. m.p. 52-54°C), which upon oxidation with periodic acid in tertiary butyl alcohol gave 12-oxododecanoic acid with an isolated yield of 71.0%. Reaction of the oxoacid with hydroxylamine hydrochloride gave 12-oxododecanoic acid oxime, which was catalytically reduced to give 12-aminododecanoic acid with a yield greater than 85% and a melting point of 184-186°C (lit. m.p. 185-187°C). 11-Aminoundecanoic acid was prepared from the 12-oxododecanoic acid oxime via a threestep reaction sequence that involved a Beckmann rearrangement, Hofmann degradation, and hydrolysis. Thus, the aldoxime acid was hydrolyzed in the presence of nickel acetate tetrahydrate to give 11-carbamoylundecanoic acid (48% yield, m.p. 129-131°C, lit. m.p. 129-130°C). The amide was then treated with a solution of sodium methoxide and bromine at 70-80°C to give 11-(methoxycarbonylamino)undecanoic acid at 75% yield (m.p. 84-86°C; elemental analysis, calculated for C 13 H 25 NO 4 : C, 60.19; H, 9.73; N, 5.40; O, 24.68%; found C, 60.02; H, 9.81; N, 5.26; O, 24.91%), which upon alkaline hydrolysis and subsequent neutralization gave 11-aminoundecanoic acid at 34% yield (m.p. 189-192°C, lit. m.p. 190°C). Mass spectrometric and 13 C nuclear magnetic resonance data of the previously unreported 11-(methoxycarbonylamino)undecanoic acid is provided. JAOCS 72, 531-538 (1997). SCHEME 1 FIG. 1. Proton-decoupled 13 C nuclear magnetic resonance spectrum of vernolic acid. Peaks are referenced to CHCl 3 at 77 ppm. Samples were made to 10 wt% in CDCl 3 . Operating frequency was at 75.6 MHz. Chemical shifts (δ = ppm): carbonyl carbon, 180; olefinic carbons, 124 and 133; epoxy carbons, 56 and 57.

Fatty acid compositions of the seed oils from eighteen varieties of amaranthus species have been determined after room temperature transesterification. Consistent with earlier studies, wide variations in the fatty acid composition are reported, and appear to be agronomically related. All varieties show significant levels (2-5%) of squalene and a combined linoleic acid and oleic acid occurrence of between 70-80%. This study represents the first reported fatty acid composition of grain amaranthus cultivated in West Africa.