LBF18108EO01

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Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

Journals (雑誌一覧)

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Upper classes: LB LBF

IDs and Links
LipidBank	DFA8013
LipidMaps	LMFA01050119
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF18108EO01

12,13-Epoxy-9-hydroxy-10-octadecenoate
Structural Information
Systematic Name	12,13-Epoxy-9-hydroxy-10-octadecenoic acid
Common Name	12,13-Epoxy-9-hydroxy-10-octadecenoate
Symbol
Formula	C18H32O4
Exact Mass	312.23005951199997
Average Mass	312.44428
SMILES	C(C(C=CC(O)CCCCCCCC(O)=O)1)(CCCCC)O1
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	A degradation product of 13-hydroperoxylinoleate in the presence of Fe(III)-cystein Gardner_HW et al. or hemoglobin Hamberg_M Hamberg_M . Degradation products of 13-hydroperoxymethyllinoleate by radical reactions Schieberle_P et al. Schieberle_P et al.. A major component of epoxy-hydroxy compounds generated from methyllinoleate by autooxydation.
Chemical Synthesis
Metabolism
Biological Activity
Genetic Information
Note
Spectral Information
Mass Spectra	GC-EI-MS(after methanolysis and trimethylsilylation) Neff_WE et al. SchieberlePet al. Graveland_A_ Frankel_EN et al. Sessa_DJ et al.: m/e=398[M], 383[M-CH3], 367[M-OCH3], 327[M-(CH2)4CH3], 241[M-(CH2)7COOCH3], 285[CH=CH-CH(OTMS)-(CH2)7COOCH3], 259[SMTO=CH-(CH2)7COOCH3]GC-EI-MS(after methanolysis and trimethylsiltlation under acidity) Gardner_HW et al. GC-EI-MS(after BF3-MeOH treatment and trimethylsilylation) SchieberlePet al.
UV Spectra	λ =277 and 316nm(very weak absorption) Graveland_A_
IR Spectra	Methyl ester Neff_WE et al. SchieberlePet al. Graveland_A_ Gardner_HW et al. Sessa_DJ et al.: trans olefin(965-958cm-1), trans epoxide( 890-874cm-1), cis epoxide(weak absorption; 845 and 830cm-1), free OH(3600cm-1)bonded OH(3640-3380cm-1)
NMR Spectra	1H-NMR Gardner_HW et al. Neff_WE et al. SchieberlePet al. Graveland_A_ : C9(3.9-4.2ppm), C10(5.93-5.95ppm), C11(5.41-5.53ppm), C12(3.09-3.1ppm; trans epoxide), C13(2.81-2.83ppm; trans epoxide), C12, 13(2.9- 3.4ppm; cis epoxide),OH proton(3.6ppm), J10-11=15.6Hz(trans unsaturation),J12-13=2-2.2Hz(trans epoxide)
Other Spectra	ORD analysis Gardner_HW et al.
Chromatograms

Reported Metabolites, References

Biospecies ID Compound Name Reference Comment n.a. LBF18108EO01 See above. Frankel_EN et al. 1977 n.a. LBF18108EO01 See above. Gardner_HW et al. 1981 n.a. LBF18108EO01 See above. Gardner_HW et al. 1978 n.a. LBF18108EO01 See above. Graveland_A_ 1970 n.a. LBF18108EO01 See above. Hamberg_M 1983 n.a. LBF18108EO01 See above. Hamberg_M 1975 n.a. LBF18108EO01 See above. Neff_WE et al. 1978 n.a. LBF18108EO01 See above. Schieberle_P et al. 1981 n.a. LBF18108EO01 See above. Schieberle_P et al. 1979 n.a. LBF18108EO01 See above. Sessa_DJ et al. 1977