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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IDs and Links | |
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LipidBank | DFA0180 |
LipidMaps | LMFA01030141 |
CAS | |
KEGG | {{{KEGG}}} |
KNApSAcK | {{{KNApSAcK}}} |
mol | LBF18306SC02 |
(6Z,9Z,12Z) -Octadecatrienoic acid | |
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Structural Information | |
(cis-6,cis-9,cis-12) -Octadecatrienoic acid | |
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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 | |
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