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Fatty acid


DATA No : DFA8057 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-13,15-Epidioxy-16-Hydroperoxy-9,11-Octadecadienoate

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:Conjugated cis, trans diene: lmax=234-237nm, conjugated trans, trans diene: lmax=231-234nm (Ref. 8078/8081/8083/8084/8088)

IR SPECTRA:OOH group: 3720-3140cm-1[bonded], 3530-3520cm-1[FREE]; olefinic protons: 3020-3000cm-1; conjugated cis, trans diene : 989-980cm-1, 955-947cm-1; conjugatedtrans, trans diene: 992-984cm-1, 955cm-1(Ref. 8078/8081/8083/8084/8085/8088)

NMR SPECTRA:1H-NMR(Ref. 8081/8083/8084/8088): C9: 5.46-5.78; C10: 5.99-6.05; C11: 6.26-6.67; C12: 5.53- 5.62; C13: 4.75-4.84; C14: 2.23-2.47, 2.79-2.88; C15: 4.47-4.49; C16: 3.86-4.15; OOH: 8.98-9.55ppm; J9-15=10.0-11.0[cis]; J9-10=15.1-15.5[trans]; J11-12=14.5-15.4Hz[trans]

MASS SPECTRA:GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8081): m/e=397[M-CH3], 131[SMTO=CHCH2CH3]; GC-EI-MS(after reduction(NaBH4 or KI) and TMS-derivatization)(Ref. 8077): m/e=311[SMTO=CH-CH=CH-CH=CH-(CH2)7COOCH3]; 131[SMTO=CHCH2CH3]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Auto oxydation of linoleate(Ref. 8081/8083). Oxydation of linoleate in the presence of Fe(III)-ascorbic acid(Ref. 8078). Photoenhancemant of linoleate peroxydation[Type II](Ref. 8084/8085). Production mechanism(Ref. 8026/8039).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE
Major secondary products of linolenate by autooxidation(Ref. 8026/8081). It is formed through 1, 3 cyclization of 13-peroxy radical of linolenate(Ref. 8025/8026/8027/8039/8028/8083).
REFERENCES
[8025]
AUTHOR:Frankel, E. N.
TITLE:Volatile lipid oxidation products PubMed ID:6306693
JOURNAL:Prog Lipid Res.
VOL:22 PAGE : 1-33 (1983)
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[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)
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[8027]
AUTHOR:Frankel, E. N.(1985 ) Chemistry of Autoxidation: Mechanism, products and Flavor Significance, in Flavor Chemistry of Fats and Oils (Min, D. B. and Smouse, T. H.,eds.),pp1-37,American Oil Chemisits' Society, Champaign, IL.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[8028]
AUTHOR:Chan, H. W.-S., Coxon, D. T., Peers, K. E., and Price, K. R.
TITLE:Oxidative Reactions of Unsaturated Lipids
JOURNAL:Food Chemistry
VOL:9 PAGE : 21 -34 (1982)
[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]

[8077]
AUTHOR:Frankel, E. N., Neff, W. E., Rohwedder, W. K., Khambay, B. P. S., Garwood, R. F., and Weedon, B. C. L.
TITLE:Analysis of Autoxidized Fats By Gas Chromatography- Mass Spectrometry: III. Methyl Linolenate.
JOURNAL:Lipids
VOL:12 PAGE : 1055 -1061 (1977)
[TOP]

[8078]
AUTHOR:Toyoda, I., Terao, J.,And Matsushita, S.
TITLE:Hydroperoxides Formed by Ferrous Ion- Catalyzed Oxidation of Methyl Linolenate
JOURNAL:Lipids
VOL:17 PAGE : 84 -90 (1982)
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[8081]
AUTHOR:Neff, W. E., Frankel, E. N., and Weisleder, D.
TITLE:High Pressure Liquid Chromatography of Autoxidized Lipids: II. Hydroperoxycyclic Peroxides and Other Secondary Products from Methyl Linolenate
JOURNAL:Lipids
VOL:16 PAGE : 439 -448 (1981)
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[8083]
AUTHOR:Coxon, D. T., Price, K. R., and Chan, H. W. - S.
TITLE:Formation, Isolation and Structure Determination of Methyl Linolenate Diperoxides
JOURNAL:Chem. Phys. Lipids
VOL:28 PAGE : 365 -378 (1981)
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[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)
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[8085]
AUTHOR:Neff, W. E., and Frankel, E. N.
TITLE:Photosensitized Oxidation of Methyl Linolenate Monohydroperoxides: Hydro-Peroxy Cyclic Peroxides, Dihydroperoxides and Hydroperoxy Bis- Cyclic Peroxides
JOURNAL:Lipids
VOL:19 PAGE : 952 -957 (1984)
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[8088]
AUTHOR:Chan, H. W. - S., Matthew, J. A., and Coxon, D. T.
TITLE:A Hydoperoxy- Epidioxide from The Autoxidation of A Hydroperoxide of Methyl Linolenate
JOURNAL:J. Chem. Soc. Chem. Commun.
VOL: PAGE : 235 -236 (1980)
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[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)
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