LBF18306SC02

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Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

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Upper classes: LB LBF

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

γ-Linolenic acid
Structural Information
Systematic Name	cis-6, cis-9, cis-12-Octadecatrienoic acid
Common Name	γ-Linolenic acid cis-6, cis-9, cis-12-Octadecatrienoic acid
Symbol
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	dX420 0.9164
Optical Rotation	1.4800 at 20°C
Refractive Index
Solubility	soluble in acetone, ether, methylalcohol 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 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.;>
Biological Activity
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