LBF18108EO02

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Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

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Upper classes: LB LBF

IDs and Links
LipidBank	DFA8017
LipidMaps	LMFA01060067
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF18108EO02

12,13-Epoxy-9-oxo-10-octadecenoic acid
Structural Information
Systematic Name	12,13-Epoxy-9-oxo-10-octadecenoic acid
Common Name	12,13-Epoxy-9-oxo-10-octadecenoic acid
Symbol
Formula	C18H30O4
Exact Mass	310.21440944799997
Average Mass	310.4284
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 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-EI-MS(after NaBH4-reduction, methanolysis and trimethylsilylation) Gardner_HW et al. HambergM GC-EI-MS(after BF3-MeOH treatment and trimethylsilylation) SchieberlePet al. Gardner_HW et al.: m/e=428[M], 413[M-CH3], 328[CH3OCH-CH=CH-C(O)-(CH2)7-C(OTMS)OCH3], 173[SMTO=CH(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: C8(2.52ppm), C10(6.34-6.36ppm), C11(6.57-6.63ppm), C12(3.2ppm; trans epoxide), C13(2.9ppm; trans epoxide), C12(3.47ppm; cis epoxide), C13(3.14ppm; cis epoxide), J12-13=2Hz(trans epoxide), J12-13=4Hz(cis epoxide), J10-11=16Hz(trans olefin)
Other Spectra	ORD analysis
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF18108EO02 See above. Gardner_HW et al. 1981 n.a. LBF18108EO02 See above. Gardner_HW et al. 1977 n.a. LBF18108EO02 See above. Gardner_HW et al. 1974 n.a. LBF18108EO02 See above. Hamberg_M 1975 n.a. LBF18108EO02 See above. Schieberle_P et al. 1979