LBF18306SC02

Upper classes: LB LBF

γ-Linolenic acid

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

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

mol	LBF18306SC02

LBF18306SC02

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