LBF18303SC01

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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	DFA0191
LipidMaps	LMFA01030152
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF18303SC01

α-Linolenic acid
Structural Information
Systematic Name	cis-9, cis-12, cis-15-Octadecatrienoic acid
Common Name	α-Linolenic acid cis-9, cis-12, cis-15-Octadecatrienoic acid
Symbol	aLnA / C18:3n-3 / C18:3w3 / aLnn
Formula	C18H30O2
Exact Mass	278.224580204
Average Mass	278.4296
SMILES	CCC=CCC=CCC=CCCCCCCCC(O)=O
Physicochemical Information
Melting Point	-11.3 to -11°C
Boiling Point	125°C at 0.05 mmHg
Density	dX420 0.9164
Optical Rotation
Refractive Index	1.4678 at 50°C
Solubility	soluble in acetone, ethanol, ether and petroleum ether.
Source	Linseed, perilla, and hemp oils; drying oils.
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, a-linolenic acid is synthesized in plants, and relatively enriched in leaves (photosynthetic tissues). On the other hand, these desaturases are not present in animal cells, neither linoleic nor a-linolenic acid is biosynthesized in animal cells in vivo. When ingested by animals, a-linolenic acid is desaturated, elongated and chain-shortened to form eicosapantaenoic acid (20:5n-3, EPA) and docosahexaenoic acid (22:6n-3, DHA) Voss_A et al. Moore_SA et al.. 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. 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	Dietary a-linolenic acid can be further elongated and desaturated to form the long-chain n-3 fatty acids, such as eicosapentaenoic acid (EPA) and docosapentaenoic acid (DHA), which are uniquely rich in neural membranes of retina and brain in mammals. It has been reported that n-3 fatty acid deficiency produces reduced learning ability Yamamoto_N et al., impaired vision, abnormal electroretinogram Neuringer_M et al. Neuringer_M et al. and polydipsia Reisbick_S et al.. Dietary fat manipulation of perilla oil rich in a-linolenic acid reduces colonic damage in experimental Crohn's disease Shoda_R et al. Shoda_R et al..
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. LBF18303SC01 See above. Moore_SA et al. 1995 n.a. LBF18303SC01 See above. Neuringer_M et al. 1986 n.a. LBF18303SC01 See above. Neuringer_M et al. 1984 n.a. LBF18303SC01 See above. Reisbick_S et al. 1990 n.a. LBF18303SC01 See above. Shoda_R et al. 1996 n.a. LBF18303SC01 See above. Shoda_R et al. 1995 n.a. LBF18303SC01 See above. Voss_A et al. 1991 n.a. LBF18303SC01 See above. Yamamoto_N et al. 1987