LBF18206SC05

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Fatty acid (脂肪酸)

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Upper classes: LB LBF

IDs and Links
LipidBank	DFA0159
LipidMaps	LMFA01030120
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF18206SC05

Linoleic acid
Structural Information
Systematic Name	cis-9, cis-12-Octadecadienoic acid
Common Name	Linoleic acid cis-9, cis-12-Octadecadienoic acid
Symbol	LA / C18:2n-6 / C18:2w6
Formula	C18H32O2
Exact Mass	280.240230268
Average Mass	280.44548000000003
SMILES	CCCCCC=CCC=CCCCCCCCC(O)=O
Physicochemical Information
Melting Point	-5°C
Boiling Point	229°C to 230°C at 16mmHg
Density	dX420 0.9031
Optical Rotation
Refractive Index	1.4711 at 20°C
Solubility	soluble in acetone, alcohol, ether and petroleum ether. Matthews_NL et al. NicolaidesNet al.
Source	Constituent of the essential fatty acids (vitamin F) and of various microorganisms; oils of cottonseed, soybean, peanut, corn, sunflower and poppy seed.
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. Although plants synthesize and store linoleic acid and a-linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in a-linolenic acid.
Biological Activity	There are two groups of essential fatty acids for mammals, the n-6 (or w6) and the n-3 (or w3). Linoleic acid (LA) is one of the n-6 essential fatty. Animals deficient in LA show the growth retardation, skin lesions, reproductive failure, fatty liver and polydipsia Paulsrud_JR et al.. Dietary supplementation of either linoleate, g-linoleate or arachidonate prevents such symptoms completely. Its physiological functions appear to be mediated mainly through the hormone-like eicosanoids (prostaglandins, leukotriens and thromboxanes et al.) derived from arachidonic acid which is biosynthesized from LA. LA is also shown to be involved in control of the water impermeability of the skin and regulation of cholesterol synthesis and transport.
Genetic Information
Note
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra
Other Spectra
Chromatograms	Gas liquid chromatogram (provided by Dr. Akiko Horiuchi).

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF18206SC05 See above. Matthews_NL et al. 1941 n.a. LBF18206SC05 See above. Nicolaides_N et al. 1958 n.a. LBF18206SC05 See above. Okuyama_H et al. 1996 n.a. LBF18206SC05 See above. Paulsrud_JR et al. 1972