New preparation of pure petroselinic acid from fennel oil (Foeniculum vulgare)

Abstract

Pure petroselinic acid {cis-6-octadecenoic acid} has been isolated from fennel oil by acid soap crystallization at 4°C in methanol, followed by two urea segregations at room temperature and crystallization at --30°C in acetone. The purity control of petroselinic acid was effected by combined gas chromatography, and 13C nuclear magnetic resonance. This petroselinic acid preparation was compared to other previous crystallization or enzymatic methods, showing that this method is both short (four steps} and easy to apply.

The genus Thapsia as a source of petroselinic acid

“…3). Oleic acid, as well as petroselinic and linoleic acids, shows well-defined signals related to the olefin region in the 13 C NMR spectra, namely, at around δ 129.7 (C9) and 130.0 (C10), the latter often overlapping with the C9 peak of linoleic acid (20)(21)(22). A weak signal at δ 130.1 attributable to oleic acid was sometimes detectable in our oil samples suggesting a trace quantity of oleic acid in Thapsia oils.…”

“…In addition, resonances of allylic and diallylic methylenes can be identified in the spectra ( Table 1). The olefin region in the carbon NMR spectrum appears particularly important for the characterization of the oil composition (20)(21)(22). A closer inspection of this peak area, in fact, allowed us to distinguish in all the samples, on the basis of their chemical shifts, the following two unsaturated fatty acids esterified to the unit of glycerol: petroselinic acid, δ 130.95 (C7) and δ 129.33 (C6); linoleic acid (cis-9,12-octadecadienoic), δ 130.61 (C13), δ 130.37 (C9), δ 128.48 (C10), and δ 128.29 (C12) (Fig.…”

Method for obtaining three products with different properties from fennel (Foeniculum vulgare) seed

“…The principal fatty acid (FA) in fennel seed oil (FSO) comprising 60-85% of the content is petroselenic acid (PA; C18:1 6c; 6Z-octadecenoic acid) (Charvet et al, 1991;Placek, 1963). PA is of particular interest because its oxidation yields lauric and adipic acids (Corma et al, 2007;Placek, 1963).…”

Triacylglycerols of Apiaceae seed oils: Composition and regiodistribution of fatty acids

“…For example, petroselinic acid can be cleaved into lauric (12:0) acid and adipic (hexanedioic) acid, providing environmentally friendly sources of these valuable acids as they are derived from renewable oil seed crops [6,7]. In spite of their potential, the triacylglycerol (TAG) structure and the regio-and stereospecific distribution of fatty acids (FA) of seed oils from the Apiaceae family, which contain mostly palmitic, petroselinic, oleic and linoleic acids [8][9][10], are not well documented except for the regiodistribution of FA in coriander (Coriandrum sativum) seed oil [11,12] and the presence of glyceryl tripetroselinate and glyceryl trilinolenate in seed oils of the Thaspia genus [13]. This can be due, in part, to the difficulties related to the resolution of oleic (cis-9 18:1) and petroselinic acids, two isomeric FA that tend to co-elute during gas chromatography (GC) analysis [14].…”