LBF18303HP04: Difference between revisions

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Upper classes: LB LBF

Methyl-10-hydroperoxy- (8E,12Z,15Z) -octadecatrienoic acid

Structural Information
	Methyl-10-hydroperoxy- (trans-8,cis-12,cis-15) -octadecatrienoic acid
	Methyl-10-hydroperoxy- (8E,12Z,15Z) -octadecatrienoic acid

Formula	C19H32O4
Exact Mass	324.23005951199997
Average Mass	324.45498
SMILES	`CCC=CCC=CCC(OO)C=CCCCCCCC(=O)OC`
Physicochemical Information






	Oxidation of linoleate by singlet oxygen Frankel_EN Frankel_EN Frankel_EN .


	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..

	Isomerization of hydroperoxides: Positional isomers at 9, 10, 12, 13, 15, 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 : m/e=201[O=CH(CH2)8C(=OH)OCH3]; 172[CH2(CH2)7C(=O)OCH3];169[O=CH(CH2)8C=O]; GC-EI-MS (Me-ester; after reduction, TMS) Terao_Jet al.: m/e=271[SMTO=CH-CH=CH(CH2)6COOCH3], GC-EI-MS(Me-ester;after reduction, hydrogenation)
UV Spectra
IR Spectra
NMR Spectra
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies	ID	Compound Name	Reference
n.a.	LBF18303HP04	See above.	Chan_HWS 1977
n.a.	LBF18303HP04	See above.	Frankel_EN 1980
n.a.	LBF18303HP04	See above.	Frankel_EN 1983
n.a.	LBF18303HP04	See above.	Frankel_EN 1984
n.a.	LBF18303HP04	See above.	Fujimoto_K 1986
n.a.	LBF18303HP04	See above.	Fujimoto_K et al. 1984
n.a.	LBF18303HP04	See above.	Logani_MK et al. 1980
n.a.	LBF18303HP04	See above.	Sevanian_A et al. 1985
n.a.	LBF18303HP04	See above.	Terao_J et al. 1977

@@ Line 6: / Line 6: @@
 |LipidBank=DFA8054
 |LipidMaps=LMFA01040038
-|SysName=Methyl-10-Hydroperoxy-8,12,15-Octadecatrienoate
+|SysName=Methyl-10-hydroperoxy- (trans-8,cis-12,cis-15) -octadecatrienoic acid
-|Common Name=&&Methyl-10-Hydroperoxy-8,12,15-Octadecatrienoate&&
+|Common Name=&&Methyl-10-hydroperoxy- (8E,12Z,15Z) -octadecatrienoic acid&&
 |Mass Spectra=EI-MS(Me-ester; after reduction and hydrogenation)[[Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100}}]]: m/e=201[O=CH(CH2)8C(=OH)OCH3]; 172[CH2(CH2)7C(=O)OCH3];169[O=CH(CH2)8C=O]; GC-EI-MS (Me-ester; after reduction, TMS)[[Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234}}]]: m/e=271[SMTO=CH-CH=CH(CH2)6COOCH3], GC-EI-MS(Me-ester;after reduction, hydrogenation)
-|Source=Oxidation of linoleate by singlet oxygen[[Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]];>.
+|Source=Oxidation of linoleate by singlet oxygen<!--8022--><!--8023-->[[Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]]<!--8027--><!--8030-->.
 |Chemical Synthesis=
 |Metabolism=
+|Biological Activity=Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.[[Reference:Logani_MK:Davies_RE:,Lipids,1980,15,485|{{RelationTable/GetFirstAuthor|Reference:Logani_MK:Davies_RE:,Lipids,1980,15,485}}]]<!--8044--><!--8045-->[[Reference:Sevanian_A:Hochstein_P:,Annu. Rev. Nutr.,1985,5,365|{{RelationTable/GetFirstAuthor|Reference:Sevanian_A:Hochstein_P:,Annu. Rev. Nutr.,1985,5,365}}]][[Reference:Fujimoto_K:,Fragrance J. (in Japanese),1986,76,21|{{RelationTable/GetFirstAuthor|Reference:Fujimoto_K:,Fragrance J. (in Japanese),1986,76,21}}]]<!--8048--><!--8049-->. It reacts with DNA in the presence of Fe ions and ascorbic acid[[Reference:Fujimoto_K:Neff_WE:Frankel_EN:,Biochim. Biophys. Acta,1984,795,100|{{RelationTable/GetFirstAuthor|Reference:Fujimoto_K:Neff_WE:Frankel_EN:,Biochim. Biophys. Acta,1984,795,100}}]].
+|Note=Isomerization of hydroperoxides: Positional isomers at 9, 10, 12, 13, 15, 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.
 }}
 {{Lipid/Footer}}

IDs and Links
LipidBank	DFA8054
LipidMaps	LMFA01040038
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}

mol	LBF18303HP04

LBF18303HP04: Difference between revisions

Latest revision as of 18:51, 29 October 2010

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