Fatty acid

DATA No : DFA8067 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-10,12,13,15-Bisepidioxy-9-Hydroperoxy-16-Octadecenoate

BIOLOGICAL ACTIVITY

It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).

PHYSICAL AND CHEMICAL PROPERTIES

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:	OOH group: 3700-3150cm^-¹[bonded], 3530cm^-¹[free], isolated trans unsaturation: 960cm^-¹(Ref. 8084)

NMR SPECTRA	:	¹H-NMR(Ref. 8084): C2: 2.3ppm; C9: 3.88ppm[C9-10 erythro], 4.17ppm[C9-10 threo]; C10, 12, 13, 15: 4.47ppm; C11, 14: 2.1-2.8ppm; C16: 5.88ppm; C17: 5.35ppm; C18: 1.73ppm; OOH: 8.73ppm[C9-10 erythro], 9.20ppm[C9-10 threo] (Ref. 8084)

MASS SPECTRA	:	GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8084): m/e=259[SMTO=CH(CH2)7COOCH3]; 185[M-259]; GC-EI-MS(after reduction, hydrogenation, and TMS-derivatization)(105): m/e=261[SMTO=CHCH2CH(OTMS)(CH2)2CH3]; 259[SMTO=CH(CH2)7COOCH3]

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

It is produced from a 15-peroxyradical by singlet-oxygen mediated oxidation of linoleate via succesive 1,3-cyclization(Ref. 8026/8039/8084).

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES

[8026]

AUTHOR	:	Frankel, E. N.
TITLE	:	Chemistry of free radical and singlet oxidation of lipids PubMed ID:6100997
JOURNAL	:	Prog Lipid Res.
VOL	:	23 PAGE : 197-221 (1984)

[8039]

AUTHOR	:	Frankel, E. N.
TITLE	:	Secondary products of lipid oxidation PubMed ID:3311422
JOURNAL	:	Chem Phys Lipids.
VOL	:	44 PAGE : 73-85 (1987)

[8084]

AUTHOR	:	Neff, W. E., Frankel, E. N., and Weisleder, D.
TITLE	:	Photosensitized Oxidation of Methyl Linolenate. Secondary Products
JOURNAL	:	Lipids
VOL	:	17 PAGE : 780 -790 (1982)

[8096]

AUTHOR	:	Fujimoto, K., Neff, W. E., and Frankel, E. N.
TITLE	:	The reaction of DNA with lipid oxidation products, metals and reducing agents PubMed ID:6466690
JOURNAL	:	Biochim Biophys Acta.
VOL	:	795 PAGE : 100-107 (1984)