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Fatty acid


DATA No : DFA8069 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-11-(3,5-Epidioxy-2-Ethylcyclopentyl)-9-Hydroperoxy-10-Undecenoate

COMMON NAME:
SYMBOL:
FORMULA: C19H32O6 MOL.WT (average) : 356.454


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BIOLOGICAL ACTIVITY
It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:OOH group: 3620-3010cm-1[bonded], 3520cm-1[free]; isolated trans unsaturation: 960cm-1(Ref. 8084)

NMR SPECTRA:1H-NMR(Ref. 8086/8087): C9: 4.26-4.35; C10: 5.47-5.52; C11: 5.44-6.03; C12: 2.66-2.92; C13: 4.42-4.53; C15: 4.53-4.66; C16: 1.90-2.16; OOH: 7.89-7.94; 13C-NMR(Ref. 8086/8087): C9: 86.3-86.6; C10: 129.8-132.4; C11: 132.4-135.0; C12: 45.9-50.8; C13: 79.8-80.5C14: 39.3-44.1; C15: 81.7-83.0;

MASS SPECTRA:EI-MS(after reduction and TMS)(Ref. 8087): m/e=543[M-CH3]; 468[M-HOTMS]; 401[M-(CH2)7COOCH3]; 378[M-2xHOTMS]; 352[468-SMTO=CHCH2]; 323[352-CH2CH3]; 285[CH=CHCH(OTMS)(CH2)7COOCH3]; 259[SMTO=CH(CH2)7COOCH3]; 217[SMTO-CH=CH-CH=OTMS]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Photoenhancement of linoleate peroxidation(TypeII)(Ref. 8026/8039/8084). It is produced from a 13-peroxyradical of linoleate via 1,3-cyclization(Ref. 8026/8039/8084/8086/8087).
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)
[TOP]

[8039]
AUTHOR:Frankel, E. N.
TITLE:Secondary products of lipid oxidation PubMed ID:3311422
JOURNAL:Chem Phys Lipids.
VOL:44 PAGE : 73-85 (1987)
[TOP]

[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)
[TOP]

[8086]
AUTHOR:O'connor, D. E., Mihelich, E. D., and Coleman, M. C.
TITLE:Stereochemical Course of The Autoxidative Cyclization of Lipid Hydroperoxides to Prostaglandin-Like Bicyclo Endoperoxides
JOURNAL:J. Am. Chem. Soc.
VOL:106 PAGE : 3577 -3584 (1984)
[TOP]

[8087]
AUTHOR:O'connor, D. E., Mihelich, E. D., and Coleman, M. C.
TITLE:Isolation and Characterization of Bicyclo Endoperoxides Derived from Methyllinolenate
JOURNAL:J. Am. Chem. Soc.
VOL:103 PAGE : 223 -224 (1981)
[TOP]

[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)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.