LBF20406SC01

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Fatty acid (脂肪酸)

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Upper classes: LB LBF

IDs and Links
LipidBank	DFA0213
LipidMaps	LMFA01030001
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20406SC01

Arachidonic acid
Structural Information
Systematic Name	5, 8, 11, 14-Eicosatetraenoic acid / 5, 8, 11, 14-icosatetraenoic acid
Common Name	Arachidonic acid 5, 8, 11, 14-Eicosatetraenoic acid 5, 8, 11, 14-icosatetraenoic acid
Symbol	AA / Ara / C20:4n-6 / C20:4w6
Formula	C20H32O2
Exact Mass	304.240230268
Average Mass	304.46688
SMILES	C(CC=CCC=CCC=CCC=CCCCC(O)=O)CCC
Physicochemical Information
Melting Point	-49.5 °C
Boiling Point	163 °C at 1 mmHg
Density	0.9082 at 20 °C
Optical Rotation
Refractive Index	1.4824 at 20 °C
Solubility	soluble in acetone, methyl alcohol, ether and petroleum ether.
Source	Constituent of many animal phospholipids, also of some ferns and mosses. Confinded to fats of land animals; brain, liver, glandular and egg lipids.
Chemical Synthesis
Metabolism	Metabolic product of linoleic acid (9,12-18:2). The synthesis of 5,8,11,14-20:4 occurs via the following reaction sequence in the endoplasmic reticulum Sprecher_H et al.: 9,12-18:2 --> 6,9,12-18:3 --> 8,11,14-20:3 --> 5,8,11,14-20:4.
Biological Activity	There are two groups of essential fatty acids, the n-6 (or w6) and the n-3 (or w3). Arachidonic acid is n-6 fatty acids. Essential fatty acid deficiency causes skin lesion and growth retardation. Dietary supplementation of either linoleate, g-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 bioactive molecules called eicosanoids. Arachidonic acid, which is nomally found esterifing sn-2 position of phospholipids, is released by the action of phospholipase A2. Free arachidonate is used for precursors of eicosanoids, such as PG2 series of prostaglandins, leukotrienes and thromboxanes. 3) Control of the water impermeability of the skin. 4) Regulation of cholesterol synthesis and transport.
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. LBF20406SC01 See above. Horrobin_DF 1992 n.a. LBF20406SC01 See above. Sprecher_H et al. 1995