LBF20503SC01: Difference between revisions

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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 <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.
}}
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Revision as of 11:55, 25 November 2009

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Upper classes: LB LBF



Eicosapentanoic acid
LBF20503SC01.png
Structural Information
5, 8, 11, 14, 17-Eicosapentaenoic acid / 5, 8, 11, 14, 17-icosapentaenoic acid
  • Eicosapentanoic acid
  • 5, 8, 11, 14, 17-Eicosapentaenoic acid
  • 5, 8, 11, 14, 17-icosapentaenoic acid
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 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.
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