LBF20407HO07

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Upper classes: LB LBF



15S-Hydroxy- (5Z,8Z,11Z,13E) -eicosatetraenoic acid
LBF20407HO07.png
Structural Information
15S-Hydroxy- (cis-5,cis-8,cis-11,trans-13) -eicosatetraenoic acid
  • 15S-Hydroxy- (5Z,8Z,11Z,13E) -eicosatetraenoic acid
  • 15(S) -Hydroxy-5,8,11,13- (Z,Z,Z,E) -eicosatetraenoic acid
15S-HETE
Formula C20H32O3
Exact Mass 320.23514489
Average Mass 320.46628
SMILES C(CC[C@@H](C=CC=CCC=CCC=CCCCC(O)=O)O)CC
Physicochemical Information
DIETHYL ETHER Baldwin_JE et al.
Baldwin_JE et al.
LBF20407HO07FT0001.gif
When arachidonic acid is oxygenated by 15-lipoxygenase, 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid is produced Bryant_RW et al.. The latter compound is reduced to a corresponding 15(S)-hydroxy acid with whole cells or crude enzyme preparations.
In connection with biological activities of 15-hydroxyeicosatetraenoic acid, there are reports for pain response of skin, mucus secretion in airway, histamine hypersensitivity, prolactin secretion, and regulation of protein phosporylation and cell signalling Kuhn_H et al..
Spectral Information
Mass Spectra METHYL ESTER TMS ETHER ; m/e 406(M+), 391, 335, 316, 305, 225, 173 Baldwin_JE et al.
UV Spectra METHYL ESTER ; λ (ISOOCTANE) = 236nm( ε 27200) Baldwin_JE et al.
IR Spectra
NMR Spectra METHYL ESTER ; 1H-NMR(90MHz) : δ 6.56(dd, J=11, 14.5Hz, 1H, 13-CH), 6.02(dd, J=11,11Hz, 1H, 12-CH), 5.7(dd, J=6.8, 14.5Hz, 1H,14-CH), 5.51(dd, J=6,11Hz, 1H, 11-CH), 4.16(dd, J=6.8, 6.8Hz, 1H, 15-CH), 3.69(s, 3H, OCH3), 2.98(2H, 10-CH), 2.84(2H, 7-CH), 2.35(2H, 2-CH), 2.08(2H, 4-CH), 1.47(2H, 16-CH), 2.3-0.9(11H) Baldwin_JE et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20407HO07 See above. Baldwin_JE et al. 1979
n.a. LBF20407HO07 See above. Bryant_RW et al. 1982
n.a. LBF20407HO07 See above. Kuhn_H et al. 1995