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|LipidBank=DFA0220
|LipidBank=DFA0220
|LipidMaps=LMFA01030181
|LipidMaps=LMFA01030181
|SysName=5, 8, 11, 14, 17-Eicosapentaenoic acid / 5, 8, 11, 14, 17-icosapentaenoic acid
|SysName=cis-5, cis-8, cis-11, cis-14, cis-17-Eicosapentaenoic acid
|Common Name=&&Eicosapentanoic acid&&5, 8, 11, 14, 17-Eicosapentaenoic acid&&5, 8, 11, 14, 17-icosapentaenoic acid&&
|Common Name=&&EPA&&5, 8, 11, 14, 17-Eicosapentaenoic acid&&
|Melting Point=-54.4 to -53.8 °C
|Melting Point=-54.4 to -53.8 °C
|Optical=1.4977 at 23 °C
|Refractive=1.4977 at 23 °C
|Solubility=soluble in heptane and methyl alcohol.
|Solubility=soluble in heptane and methyl alcohol.<!--0265--><!--0269-->
|Mass Spectra=""METHYL ESTER:316,300,287,262,247,234,215,201,180,161,152 "" [[Reference:Karlsson_KA:Samuelsson_BE:Steen_GO:,Acta Chem. Scand.,1968,22,1361|{{RelationTable/GetFirstAuthor|Reference:Karlsson_KA:Samuelsson_BE:Steen_GO:,Acta Chem. Scand.,1968,22,1361}}]]
|Mass Spectra=""METHYL ESTER:316,300,287,262,247,234,215,201,180,161,152 "" [[Reference:Karlsson_KA:Samuelsson_BE:Steen_GO:,Acta Chem. Scand.,1968,22,1361|{{RelationTable/GetFirstAuthor|Reference:Karlsson_KA:Samuelsson_BE:Steen_GO:,Acta Chem. Scand.,1968,22,1361}}]]
|NMR Spectra=""METHYL ESTER:
|NMR Spectra=""METHYL ESTER:
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|Source=Present in fish oils as an acylglycerol and animal phospholipids. Cattle-liver lipids; various fish and seal oils.
|Source=Present in fish oils as an acylglycerol and animal phospholipids. Cattle-liver lipids; various fish and seal oils.
|Chemical Synthesis=
|Chemical Synthesis=
|Metabolism=Metabolic product of <FONT FACE="Symbol">a</FONT>-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 [[Reference:Sprecher_H:Luthria_DL:Mohammed_BS:Baykousheva_SP:,J. Lipid. Res.,1995,36,2471|{{RelationTable/GetFirstAuthor|Reference:Sprecher_H:Luthria_DL:Mohammed_BS:Baykousheva_SP:,J. Lipid. Res.,1995,36,2471}}]]: 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.
|Metabolism=Metabolic product of alpha -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 [[Reference:Sprecher_H:Luthria_DL:Mohammed_BS:Baykousheva_SP:,J. Lipid. Res.,1995,36,2471|{{RelationTable/GetFirstAuthor|Reference:Sprecher_H:Luthria_DL:Mohammed_BS:Baykousheva_SP:,J. Lipid. Res.,1995,36,2471}}]]: 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.
|Symbol=EPA / C20:5n-3 / C20:5 omega 3
|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. [[Reference:Bang_HO:Dyerberg_J:,Acta Med. Scand.,1972,192,85|{{RelationTable/GetFirstAuthor|Reference:Bang_HO:Dyerberg_J:,Acta Med. Scand.,1972,192,85}}]][[Reference:Dyerberg_J:Bang_HO:Stoffersen_E:Moncada_S:Vane_JR:,Lancet,1978,2,117|{{RelationTable/GetFirstAuthor|Reference:Dyerberg_J:Bang_HO:Stoffersen_E:Moncada_S:Vane_JR:,Lancet,1978,2,117}}]]
}}
}}


{{Lipid/Footer}}
{{Lipid/Footer}}

Latest revision as of 00:13, 21 July 2016

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(脂肪酸)
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Upper classes: LB LBF



EPA
LBF20503SC01.png
Structural Information
cis-5, cis-8, cis-11, cis-14, cis-17-Eicosapentaenoic acid
  • EPA
  • 5, 8, 11, 14, 17-Eicosapentaenoic acid
EPA / C20:5n-3 / C20:5 omega 3
Formula C20H30O2
Exact Mass 302.224580204
Average Mass 302.451
SMILES C(CC=CCC=CCC=CCC=CCCCC(O)=O)=CCC
Physicochemical Information
-54.4 to -53.8 °C
1.4977 at 23 °C
soluble in heptane and methyl alcohol.
Present in fish oils as an acylglycerol and animal phospholipids. Cattle-liver lipids; various fish and seal oils.
Metabolic product of alpha -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.
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.
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
LBF20503SC01CH0001.gif
(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