LBF18107EO02

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Upper classes: LB LBF



9,10-Epoxy-13-oxo-11-octadecenoic acid
LBF18107EO02.png
Structural Information
Systematic Name 9,10-Epoxy-13-oxo-11-octadecenoic acid
Common Name
  • 9,10-Epoxy-13-oxo-11-octadecenoic acid
Symbol
Formula C18H30O4
Exact Mass 310.21440944799997
Average Mass 310.4284
SMILES C(C(C=CC(=O)CCCCC)1)(CCCCCCCC(O)=O)O1
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[the epoxide ring: trans or cis, the double bond: trans] Gardner_HW et al. Gardner_HW et al.. A minor reactive product between linoleate and soy bean extracts Gardner_HW et al..
Chemical Synthesis
Metabolism
Biological Activity
Genetic Information
Note
Spectral Information
Mass Spectra GC-EI-MS(after methanolysis and trimethylsilylation ) Gardner_HW et al., GC-EIMS(after BF3-MeOH treatment and trimethylsilylation)(075/072): m/e=428[M], 413[M-CH3], 259[SMTO=CH(CH2)7- COOCH3], 242[CH3OCH-CH=CH-C(OTMS)(CH2)4CH3]
UV Spectra λ ether/max=229-230nm; ε =16500 ( α , β -unsaturated carbonyl) Gardner_HW et al. SchieberlePet al.
IR Spectra Methyl ester: trans monoene(973cm-1), trans epoxide(885cm-1), cis epoxide(825 cm-1), conjugated carbonyl(1700, 1680, and 1635cm-1) Gardner_HW et al.
NMR Spectra 1H-NMR Gardner_HW et al.: C9(2.9ppm;trans epoxide), C10(3.20ppm; trans epoxide), C9(3.14ppm; cis-epoxide),C10(3.47ppm; cis epoxide), C11(6.57-6.63ppm), C12(6.34-6.36ppm), C14(2.52ppm), J9-10=2Hz(trans epoxide), J9-10=4Hz(cis epoxide), J11-12=16Hz(trans olefin)
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18107EO02 See above. Gardner_HW et al. 1981
n.a. LBF18107EO02 See above. Gardner_HW et al. 1974
n.a. LBF18107EO02 See above. Schieberle_P et al. 1979


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