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

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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 C

BOILING POINT	:	163 C at 1 mmHg

REFRACTIVE INDEX	:	1.4824 at 20 C

OPTICAL ROTATION	:

DENSITY	:	0.9082 at 20 C

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	:

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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)

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[0225]

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

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[0328]

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

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[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 : - ()

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[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)

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[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)

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