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Fatty acid


DATA No : DFA0220 INFORMANT : Tetsuyuki Kobayashi

NAME : 5, 8, 11, 14, 17-Eicosapentaenoic acid / 5, 8, 11, 14, 17-icosapentaenoic acid

COMMON NAME: Eicosapentanoic acid
SYMBOL: EPA / C20:5n-3 / C20:5w3
FORMULA: C20H30O2 MOL.WT (average) : 302.451


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BIOLOGICAL ACTIVITY
Considered to be the major reason for the beneficial effects of fish oils on the cardiovascular system. EPA is a precursor to series 3 eicosanoids that promote dilation of blood vessels and a slower blood clotting reaction and, as such, has been found to be critical to the maintenance of normal cardiovascular health. (Ref. 2019/2020)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:-54.4 to -53.8 degC

BOILING POINT:

REFRACTIVE INDEX:1.4977 at 23 degC

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:soluble in heptane and methyl alcohol.(Ref. 0265)(Ref. 0269)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:""METHYL ESTER:

MASS SPECTRA:""METHYL ESTER:316,300,287,262,247,234,215,201,180,161,152 "" (Ref. 6056)

OTHER SPECTRA:
CHROMATOGRAM DATA
Gas liquid chromatogram
[Chromatogram 0001] (provided by Dr. Akiko Horiuchi).
SOURCE
Present in fish oils as an acylglycerol and animal phospholipids. Cattle-liver lipids; various fish and seal oils.
CHEMICAL SYNTHESIS

METABOLISM
Metabolic product of a-linolenic acid (9,12,15-18:3). The synthesis of 5,8,11,14,17-20:5 (=EPA) occurs via the following reaction sequence in the endoplasmic reticulum (Ref. 2013): 9,12,15-18:3 --> 6,9,12,15-18:4 --> 8,11,14,17-20:4 --> 5,8,11,14,17-20:5 --> 7,10,13,16,19-22:5. EPA is further metabolized to DHA. Precursor of PG3 series of prostaglandins.
GENETIC INFORMATION

NOTE

REFERENCES
[0265]
AUTHOR:Ito,S., and K.Fukuzumi.
TITLE:
JOURNAL:Yukagaku
VOL:12 PAGE : 272 -272 (1963)
[TOP]

[0269]
AUTHOR:Jangaard,P.M., and R.G.Ackman.
TITLE:
JOURNAL:J.Fish.Res.Bd.Can.
VOL:22 PAGE : 131 -131 (1964)
[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]

[2019]
AUTHOR:Bang, H. O., and Dyerberg, J.
TITLE:Plasma lipids and lipoproteins in Greenlandic west coast Eskimos PubMed ID:5052396
JOURNAL:Acta Med Scand.
VOL:192 PAGE : 85-94 (1972)
[TOP]

[2020]
AUTHOR:Dyerberg, J., Bang, H. O., Stoffersen, E., Moncada, S., and Vane, J. R.
TITLE:Eicosapentaenoic acid and prevention of thrombosis and atherosclerosis? PubMed ID:78322
JOURNAL:Lancet.
VOL:2 PAGE : 117-119 (1978)
[TOP]

[6056]
AUTHOR: Karlsson,K.-A., Samuelsson,B.E.,and Steen,G.O.
TITLE:Structure and Function of Sphingolipids 1.Differencesin Sphingolipid long-chain Base pattern between Kidney Cortex, Medulla and Papillae. PubMed ID:5727637
JOURNAL:Acta Chem.Scand.
VOL:22 PAGE : 1361 -1363 (1968)
[TOP]

[6058]
AUTHOR: Irie,A., Kubo,H.,and Hoshi,M.
TITLE:Glucosylceramide having a Novel Triun Saturated Long-chain Base from the Spermatozoa of the Starfish, Asterias Amurensis. PubMed ID:2358431
JOURNAL:J. Biochem
VOL:107 PAGE : 578 -586 (1990)
[TOP]

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