LBF20503SC01

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Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

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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
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	1.4977 at 23 °C
Refractive Index
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
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