LBF20406SC01: Difference between revisions

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|LipidBank=DFA0213
|LipidBank=DFA0213
|LipidMaps=LMFA01030001
|LipidMaps=LMFA01030001
|SysName=5, 8, 11, 14-Eicosatetraenoic acid / 5, 8, 11, 14-icosatetraenoic acid
|SysName=(cis-5,cis-8,cis-11,cis-14) -Eicosatetraenoic acid
|Common Name=&&Arachidonic acid&&5, 8, 11, 14-Eicosatetraenoic acid&&5, 8, 11, 14-icosatetraenoic acid&&
|Common Name=&&Arachidonic acid&&(5Z,8Z,11Z,14Z) -Eicosatetraenoic acid&&
|Melting Point=-49.5 °C
|Melting Point=-49.5 °C
|Boiling Point=163 °C at 1 mmHg
|Boiling Point=163 °C at 1 mmHg
|Density=0.9082 at 20 °C
|Density=0.9082 at 20 °C
|Refractive=1.4824 at 20 °C
|Refractive=1.4824 at 20 °C
|Solubility=soluble in acetone, methyl alcohol, ether and petroleum ether.
|Solubility=soluble in acetone, methyl alcohol, ether and petroleum ether.<!--0224--><!--0225--><!--0328--><!--0347-->
|Source=Constituent of many animal phospholipids, also of some ferns and mosses. Confinded to fats of land animals; brain, liver, glandular and egg lipids.
|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=
|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 [[Reference:Sprecher_H:Luthria_DL:Mohammed_BS:Baykousheva_SP:,J. Lipid. Res.,1995,36,2471|{{RelationTable/GetFirstAuthor|Reference:Sprecher_H:Luthria_DL:Mohammed_BS:Baykousheva_SP:,J. Lipid. Res.,1995,36,2471}}]]: 9,12-18:2 --> 6,9,12-18:3 --> 8,11,14-20:3 --> 5,8,11,14-20:4.
|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 [[Reference:Sprecher_H:Luthria_DL:Mohammed_BS:Baykousheva_SP:,J. Lipid. Res.,1995,36,2471|{{RelationTable/GetFirstAuthor|Reference:Sprecher_H:Luthria_DL:Mohammed_BS:Baykousheva_SP:,J. Lipid. Res.,1995,36,2471}}]]: 9,12-18:2 --> 6,9,12-18:3 --> 8,11,14-20:3 --> 5,8,11,14-20:4.
|Symbol=AA / Ara / C20:4n-6 / C20:4<FONT FACE="Symbol">w</FONT>6
|Symbol=AA / Ara / C20:4n-6 / C20:4 omega 6
|Biological Activity=There are two groups of essential fatty acids, the n-6 (or <FONT FACE="Symbol">w</FONT>6) and the n-3 (or <FONT FACE="Symbol">w</FONT>3). Arachidonic acid is n-6 fatty acids. Essential fatty acid deficiency causes skin lesion and growth retardation. Dietary supplementation of either linoleate, <FONT FACE="Symbol">g</FONT>-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 bioactive molecules called eicosanoids. Arachidonic acid, which is nomally found esterifing sn-2 position of phospholipids, is released by the action of phospholipase A<SUB><FONT SIZE=-1>2</FONT></SUB>. Free arachidonate is used for precursors of eicosanoids, such as PG<SUB><FONT SIZE=-1>2</FONT></SUB> series of prostaglandins, leukotrienes and thromboxanes. 3) Control of the water impermeability of the skin. 4) Regulation of cholesterol synthesis and transport.
|Biological Activity=There are two groups of essential fatty acids, the n-6 (or omega 6) and the n-3 (or omega 3). Arachidonic 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 bioactive molecules called eicosanoids. Arachidonic acid, which is nomally found esterifing sn-2 position of phospholipids, is released by the action of phospholipase A_2 . Free arachidonate is used for precursors of eicosanoids, such as PG_2  series of prostaglandins, leukotrienes and thromboxanes. 3) Control of the water impermeability of the skin. 4) Regulation of cholesterol synthesis and transport.
}}
}}


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Latest revision as of 06:27, 20 July 2016

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Upper classes: LB LBF



Arachidonic acid
LBF20406SC01.png
Structural Information
(cis-5,cis-8,cis-11,cis-14) -Eicosatetraenoic acid
  • Arachidonic acid
  • (5Z,8Z,11Z,14Z) -Eicosatetraenoic acid
AA / Ara / C20:4n-6 / C20:4 omega 6
Formula C20H32O2
Exact Mass 304.240230268
Average Mass 304.46688
SMILES C(CC=CCC=CCC=CCC=CCCCC(O)=O)CCC
Physicochemical Information
-49.5 °C
163 °C at 1 mmHg
0.9082 at 20 °C
1.4824 at 20 °C
soluble in acetone, methyl alcohol, ether and petroleum ether.
Constituent of many animal phospholipids, also of some ferns and mosses. Confinded to fats of land animals; brain, liver, glandular and egg lipids.
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.
There are two groups of essential fatty acids, the n-6 (or omega 6) and the n-3 (or omega 3). Arachidonic 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 bioactive molecules called eicosanoids. Arachidonic acid, which is nomally found esterifing sn-2 position of phospholipids, is released by the action of phospholipase A_2 . Free arachidonate is used for precursors of eicosanoids, such as PG_2 series of prostaglandins, leukotrienes and thromboxanes. 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. LBF20406SC01 See above. Horrobin_DF 1992
n.a. LBF20406SC01 See above. Sprecher_H et al. 1995