LBF20503SC01

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Fatty acid (脂肪酸)

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Upper classes: LB LBF

IDs and Links
LipidBank	DFA0220
LipidMaps	LMFA01030181
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20503SC01

Eicosapentanoic acid
Structural Information
Systematic Name	5, 8, 11, 14, 17-Eicosapentaenoic acid / 5, 8, 11, 14, 17-icosapentaenoic acid
Common Name	Eicosapentanoic acid 5, 8, 11, 14, 17-Eicosapentaenoic acid 5, 8, 11, 14, 17-icosapentaenoic acid
Symbol	EPA / C20:5n-3 / C20:5w3
Formula	C20H30O2
Exact Mass	302.224580204
Average Mass	302.451
SMILES	C(CC=CCC=CCC=CCC=CCCCC(O)=O)=CCC
Physicochemical Information
Melting Point	-54.4 to -53.8 °C
Boiling Point
Density
Optical Rotation
Refractive Index	1.4977 at 23 °C
Solubility	soluble in heptane and methyl alcohol.
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 Sprecher_H et al.: 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.
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. Bang_HO et al. Dyerberg_J et al.
Genetic Information
Note
Spectral Information
Mass Spectra	""METHYL ESTER:316,300,287,262,247,234,215,201,180,161,152 "" Karlsson_KA et al.
UV Spectra
IR Spectra
NMR Spectra	""METHYL ESTER:
Other Spectra
Chromatograms	Gas liquid chromatogram (provided by Dr. Akiko Horiuchi).

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF20503SC01 See above. Bang_HO et al. 1972 n.a. LBF20503SC01 See above. Dyerberg_J et al. 1978 n.a. LBF20503SC01 See above. Karlsson_KA et al. 1968 n.a. LBF20503SC01 See above. Sprecher_H et al. 1995