Back to HOME

Fatty acid


DATA No : DFA0213 INFORMANT : Tetsuyuki Kobayashi

NAME : 5, 8, 11, 14-Eicosatetraenoic acid / 5, 8, 11, 14-icosatetraenoic acid

COMMON NAME: Arachidonic acid
SYMBOL: AA / Ara / C20:4n-6 / C20:4w6
FORMULA: C20H32O2 MOL.WT (average) : 304.467


Download ChemDraw structure data
Download Mol format file
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 (Ref. 2014): 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.
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:-49.5 degC

BOILING POINT:163 degC at 1 mmHg

REFRACTIVE INDEX:1.4824 at 20 degC

OPTICAL ROTATION:

DENSITY:0.9082 at 20 degC

SOLUBILITY:soluble in acetone, methyl alcohol, ether and petroleum ether.(Ref. 0224)(Ref. 0225)(Ref. 0328)(Ref. 0347)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

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 (Ref. 2013): 9,12-18:2 --> 6,9,12-18:3 --> 8,11,14-20:3 --> 5,8,11,14-20:4.
GENETIC INFORMATION

NOTE

REFERENCES
[0224]
AUTHOR:Hartley, P.
TITLE:
JOURNAL:J. Physiol. (London)
VOL:36 PAGE : 17 -17 (1907)
[TOP]

[0225]
AUTHOR:Hartley, P.
TITLE:
JOURNAL:J. Physiol. (London)
VOL:38 PAGE : 353 -353 (1909)
[TOP]

[0328]
AUTHOR:Levene, P. A., and Sims, H. S.
TITLE:
JOURNAL:J. Biol. Chem.
VOL:48 PAGE : 185 - (1921)
[TOP]

[0347]
AUTHOR:Markley, K. S., et. al. 1960 Fatty Acids : Their Chemistry, Properties, Production,and Uses. Ed.2. Interscience, New York. v.1, pp.23-249
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[2013]
AUTHOR:Sprecher, H., Luthria, D. L., Mohammed, B. S., and Baykousheva, S. P.
TITLE:Reevaluation of the pathways for the biosynthesis of polyunsaturated fatty acids PubMed ID:8847474
JOURNAL:J Lipid Res.
VOL:36 PAGE : 2471-2477 (1995)
[TOP]

[2014]
AUTHOR:D.F. Horrobin
TITLE:Nutritional and Medical Importance of Gamma-linolenic Acid. PubMed ID:1334266
JOURNAL:Prog. Lipid Res.
VOL:31 PAGE : 163 -194 (1992)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.