LBF18306SC02: Difference between revisions

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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
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|LipidBank=DFA0180
|LipidBank=DFA0180
|LipidMaps=LMFA01030141
|LipidMaps=LMFA01030141
|SysName=cis-6, cis-9, cis-12-Octadecatrienoic acid
|SysName=(cis-6,cis-9,cis-12) -Octadecatrienoic acid
|Common Name=&&gamma-Linolenic acid&&cis-6, cis-9, cis-12-Octadecatrienoic acid&&
|Common Name=&&(6Z,9Z,12Z) -Octadecatrienoic acid&&gamma-Linolenic acid&&
|Melting Point=-11.3 to -11°C
|Melting Point=-11.3 to -11°C
|Boiling Point=125°C at 0.05mmHg
|Boiling Point=125°C at 0.05mmHg
|Density=dX<sub>4</sub><sup>20</sup> 0.9164
|Density=d^{20}_4  0.9164
|Optical=1.4800 at 20°C
|Refractive=1.4800 at 20°C
|Solubility=soluble in acetone, ether, methylalcohol and petroleum ether.
|Solubility=soluble in acetone, ether, methyl alcohol and petroleum ether.<!--0352--><!--0383--><!--0415-->
|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.[[Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409|{{RelationTable/GetFirstAuthor|Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409}}]]
|Symbol=C18:3n-6 / C18:3 omega 6 /  gamma Lnn /  gamma LnA
|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 [[Reference:Horrobin_DF:,Prog. Lipid Res.,1992,31,163|{{RelationTable/GetFirstAuthor|Reference:Horrobin_DF:,Prog. Lipid Res.,1992,31,163}}]]: 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.
}}
}}
{{Lipid/Footer}}

Latest revision as of 10:45, 1 October 2010

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Upper classes: LB LBF



(6Z,9Z,12Z) -Octadecatrienoic acid
LBF18306SC02.png
Structural Information
(cis-6,cis-9,cis-12) -Octadecatrienoic acid
  • (6Z,9Z,12Z) -Octadecatrienoic acid
  • γ-Linolenic acid
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
-11.3 to -11°C
125°C at 0.05mmHg
d20
4
   0.9164
1.4800 at 20°C
soluble in acetone, ether, methyl alcohol 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 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.
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.
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