LBF18304HP01

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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	DFA8053
LipidMaps	LMFA01040016
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF18304HP01

16-Hydroperoxy-9,12,14-Octadecatrienoic Acid
Structural Information
Systematic Name	16-Hydroperoxy-9,12,14-Octadecatrienoic Acid/16-Hydroperoxy-9,12,14-Octadecatrienoate
Common Name	16-Hydroperoxy-9,12,14-Octadecatrienoic Acid 16-Hydroperoxy-9,12,14-Octadecatrienoate
Symbol
Formula	C18H30O4
Exact Mass	310.21440944799997
Average Mass	310.4284
SMILES	CCC(OO)C=CC=CCC=CCCCCCCCC(O)=O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	Auto oxidation of linoleate Frankel_EN Frankel_EN Frankel_EN Chan_HWS et al.. Oxidation of linoleate by singlet oxygen Frankel_EN Frankel_EN Frankel_EN .
Chemical Synthesis
Metabolism
Biological Activity	Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously. Logani_MK et al. Sevanian_A et al. Fujimoto_K . It reacts with DNA in the presence of Fe ions and ascorbic acid Fujimoto_K et al..
Genetic Information
Note	Isomerization of hydroperoxides: Positional isomers at 9, 12, 13, and 16 and their geometric isomers of cis, cis, trans- or cis, trans, trans are formed. The proportion of 9-, 16- isomers is higher than that of 12-, 13- isomers.
Spectral Information
Mass Spectra	EI-MS(Me-ester; after reduction and hydrogenation) Chan_HWS Frankel_EN et al.: m/e=285[O=CH(CH2)14C(=OH)OCH3]; 256[CH2(CH2)13C(=OH)OCH3]; 253[O=CH(CH2)14C=O], GC-EI-MS(Me-ester; after reduction,tms) Frankel_EN et al.: m/e=380[M]; 365[M-CH3]; 351[SMTO=CH-CH=CH-CH=CH-CH2-CH=CH-(CH2)7-COOCH3]
UV Spectra	(Me-ester; after reduction; in etoh) Chan_HWS et al., cis, cis, trans isomer: λ max=236nm, cis, trans, trans isomer: λ max=232nm
IR Spectra	(Me-ester; after reduction) Chan_HWS et al. Frankel_EN et al., cis, cis, trans isomer: 989-983 and 951-945cm-1; cis, trans, trans isomer: 991-983cm-1, (Me-ester) ToyodaIet al., OOH group: 3400cm-1
NMR Spectra
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies ID Compound Name Reference Comment n.a. LBF18304HP01 See above. Chan_HWS 1977 n.a. LBF18304HP01 See above. Chan_HWS et al. 1982 n.a. LBF18304HP01 See above. Chan_HWS et al. 1977 n.a. LBF18304HP01 See above. Frankel_EN 1980 n.a. LBF18304HP01 See above. Frankel_EN 1983 n.a. LBF18304HP01 See above. Frankel_EN 1984 n.a. LBF18304HP01 See above. Frankel_EN et al. 1977 n.a. LBF18304HP01 See above. Fujimoto_K 1986 n.a. LBF18304HP01 See above. Fujimoto_K et al. 1984 n.a. LBF18304HP01 See above. Logani_MK et al. 1980 n.a. LBF18304HP01 See above. Sevanian_A et al. 1985 n.a. LBF18304HP01 See above. Toyoda_I et al. 1982