LBF18306SC02

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Upper classes: LB LBF



γ-Linolenic acid
LBF18306SC02.png
Structural Information
cis-6, cis-9, cis-12-Octadecatrienoic acid
  • γ-Linolenic acid
  • cis-6, cis-9, cis-12-Octadecatrienoic acid
Formula C18H30O2
Exact Mass 278.224580204
Average Mass 278.4296
SMILES CCCCCC=CCC=CCC=CCCCCC(O)=O
Physicochemical Information
-11.3 to -11°C
125°C at 0.05mmHg
dX420 0.9164
1.4800 at 20°C
soluble in acetone, ether, methylalcohol and petroleum ether.
Isolated from seeds of Oenothera biennis and O. lamarckiana (evening primroses); drying oils. A minor component of many animal lipids.
Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of D12-desaturase, and a-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of D15-desaturase. Since both D12- and 15-desaturases are present in plant cells but not in animal cells, linoleic and a-linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form g-linolenic acid (18:3n-6), dihomo-g-linolenic acid (20:3n-6), arachidonic acid (20:4n-6) and adrenic acid (22:4n-6). Docosapentaenoic acid (22:5n-6) is synthesized from adrenic acid in significant amounts only under conditions of prolonged n-3 fatty acid deficiency., No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods. Okuyama_H et al.;>
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18306SC02 See above. Horrobin_DF 1992
n.a. LBF18306SC02 See above. Okuyama_H et al. 1996