LBF18306SC02

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IDs and Links
LipidBank	DFA0180
LipidMaps	LMFA01030141
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF18306SC02

(6Z,9Z,12Z) -Octadecatrienoic acid
Structural Information
Systematic Name	(cis-6,cis-9,cis-12) -Octadecatrienoic acid
Common Name	(6Z,9Z,12Z) -Octadecatrienoic acid γ-Linolenic acid
Symbol	C18:3n-6 / C18:3 omega 6 / gamma Lnn / gamma LnA
Formula	C18H30O2
Exact Mass	278.224580204
Average Mass	278.4296
SMILES	CCCCCC=CCC=CCC=CCCCCC(O)=O
Physicochemical Information
Melting Point	-11.3 to -11°C
Boiling Point	125°C at 0.05mmHg
Density	d20 4   0.9164
Optical Rotation
Refractive Index	1.4800 at 20°C
Solubility	soluble in acetone, ether, methyl alcohol and petroleum ether.
Source	Isolated from seeds of Oenothera biennis and O. lamarckiana (evening primroses); drying oils. A minor component of many animal lipids.
Chemical Synthesis
Metabolism	Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of Delta 12-desaturase, and alpha -linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of Delta 15-desaturase. Since both Delta 12- and 15-desaturases are present in plant cells but not in animal cells, linoleic and alpha -linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form gamma -linolenic acid (18:3n-6), dihomo- gamma -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.
Biological Activity	There are two groups of essential fatty acids, the n-6 (or omega 6) and the n-3 (or omega 3). gamma -linolenic acid is n-6 fatty acids. Essential fatty acid deficiency causes skin lesion and growth retardation. Dietary supplementation of either linoleate, gamma -linoleate or arachidonate prevents such symptoms completely. The n-6 essential fatty acids have at least four roles Horrobin_DF : 1) Modulation of membrane structure. 2) Formation of short-lived giologically active molecules. Oxygenated derivatives of gamma -linolenic acid is a Arachidonic acid may have a role in the regulation of cell devision in cancer and other cells. There are other bioactive substance, PGE1 and 15-OH-dihomogamma-linolenic acid which are both formed from gamma -linolenic acid after its rapid elongation to dihomogamma-linolenic acid. 3) Control of the water impermeability of the skin. 4) Regulation of cholesterol synthesis and transport.
Genetic Information
Note
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