LBF18107EO01

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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	DFA8012
LipidMaps	LMFA01070004
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF18107EO01

9,10-Epoxy-13-hydroxy-11-octadecenoate
Structural Information
Systematic Name	9,10-Epoxy-13-hydroxy-11-octadecenoic acid
Common Name	9,10-Epoxy-13-hydroxy-11-octadecenoate
Symbol
Formula	C18H32O4
Exact Mass	312.23005951199997
Average Mass	312.44428
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 13-hydroperoxymethyllinoleate Schieberle_P et al. Schieberle_P et al.. A major compound generated by autooxidation of methyllinoleate[the epoxide ring and double bond show trans configuration] Neff_WE et al. Frankel_EN et al.. Oxidation of linoleic acid by wheat lipoxygenase[the epoxy ring shows cis configuration].
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.: m/e= 398[M], 383[M-CH3], 367[M-OCH3], 327[M-(CH2)4CH3], 241[M-(CH2)7COOCH3]
UV Spectra	λ =277 and 316nm(very weak absorption) Graveland_A_
IR Spectra	Metyl ester Neff_WE et al. SchieberlePet al. Graveland_A_ : trans olefin(965-958cm-1), trans epoxide(890-874 cm-1), cis epoxide(weak absorprion; 845 AND 830cm-1), free OH(3600cm-1),bonded OH(3640-3380cm-1)
NMR Spectra	1H-NMR(methyl ester) Neff_WE et al. SchieberlePet al. Graveland_A_ : C9(2.83ppm), C10(3.09-3.1ppm;trans epoxide), C11(5.45-5.53ppm), C12(5.93-5.95ppm), C13(3.9-4.2ppm), C12, 13(2.9-3.4ppm;cis epoxide), OH proton(3.6ppm), J11-12=15.6Hz(trans unsaturation), J9-10=2-2.2Hz(trans epoxide)
Other Spectra
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF18107EO01 See above. Graveland_A_ 1970 n.a. LBF18107EO01 See above. Neff_WE et al. 1978 n.a. LBF18107EO01 See above. Schieberle_P et al. 1979