LBF20306EO03

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Upper classes: LB LBF



(+-) -11 (12) -Epoxy- (5Z,8Z,14Z) -eicosatrienoic acid
LBF20306EO03.png
Structural Information
Systematic Name dl-11 (12) -Epoxy- (cis-5,cis-8,cis-14) -eicosatrienoic acid
Common Name
  • (+-) -11 (12) -Epoxy- (5Z,8Z,14Z) -eicosatrienoic acid
  • 11,12-EET
Symbol (+-)11(12)-EpETrE
Formula C20H32O3
Exact Mass 320.23514489
Average Mass 320.46628
SMILES C(CC=CCC(O1)C1CC=CCC=CCCCC(O)=O)CCC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation 11(R),12(S)-EET METHYL ESTER ; [ α ]23
D
  =+4.94°(C=1.64, ACETONE) MossetPet al., 11(S),12(R)-EET METHYL ESTER ; [ α ]24
D
  =-2.34°(C=0.66, CHLOROFORM) Falck_JR et al.
Refractive Index
Solubility
Source (±)11(12)-EpETrE is biosynthesized in rat and rabbit liver microsomes by cytochrome P450 Oliw_EH et al. Chacos_N et al.. The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsome of rat Chacos_N et al. or rabbit Oliw_EH et al.
Chemical Synthesis Table0001 Mosset_P et al.
Metabolism
Biological Activity (±)11(12)-EpETrE has been shown, along with (±)8(9)-EpETrE, to play a role in the recovery of depleted Ca^{2+} pools in cultured smooth muscle cells Graber_MN et al.. The compound relaxes intestinal artery, inhibits vasopressin-dependent water flow in urinary bladder, and regulates intracellular calcium level Fitzpatrick_FA et al..
Genetic Information
Note
Spectral Information
Mass Spectra METHYL ESTER ; m/e 340(M+), 322, 309, 227, 155 Oliw_EH et al..
UV Spectra
IR Spectra
NMR Spectra 1H-NMR(CDCl3) : δ 5.54-5.20(m, 6H), 3.61(s, 3H), 3.00-2.68(m, 4H), 2.37-2.00(m, 10H), 1.81-1.54(m, 2H), 1.46-1.13(m, 6H), 0.88(t, J=7Hz, 3H) MossetPet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20306EO03 See above. Chacos_N et al. 1982
n.a. LBF20306EO03 See above. Falck_JR et al. 1984
n.a. LBF20306EO03 See above. Fitzpatrick_FA et al. 1988
n.a. LBF20306EO03 See above. Graber_MN et al. 1997
n.a. LBF20306EO03 See above. Mosset_P et al. 1986
n.a. LBF20306EO03 See above. Oliw_EH et al. 1982



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