Fatty acid

DATA No : DFA8056 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-10,12-Epidioxy-9-Hydroperoxy-13,15-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 diene: lmax=231-236nm (Ref. 8078/8081/8083/8084)

IR SPECTRA	:	OOH group: 3520 cm^-¹[free], 3700-3100cm^-¹[bonded]; olefinic protons: 3020-3000cm^-¹; CONJUGATE TRANS, CIS DIENES: 990-980cm^-¹, 955-947cm^-¹(Ref. 8079/8081/8083/8084/8085)

NMR SPECTRA	:	¹H-NMR(Ref. 8081/8084/8083): C9: 3.92-4.21; C10: 4.45-4.47; C11: 2.19-2.47, 2.81-2.87; C12: 4.77-4.80; C13: 5.57-5.62; C14: 6.65-6.68; C15: 5.96-6.65; C16: 5.50-5.55; OOH: 9.05-9.56ppm; J13-14=15Hz[C13-14 : trans]; J15-16=10Hz[C15-16: cis]13C-NMR(Ref. 8081/8084): C9: 86.0; C10, 12: 83.8, 83.0

MASS SPECTRA	:	GC-EI-MS(after reduction(PH3P) and TMS)(Ref. 8081): m/e=397[M-CH3]; 259[SMTO=CH(CH2)7COOCH3]; GC-EI-MS(after reduction with NaBH4 or KI andTMS)(Ref. 8077): m/e=259[SMTO=CH(CH2)7COOCH3]; 183[SMTO=CH-CH=CH-CH=CH-CH2CH3]

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 12-peroxy radical of linolenate(Ref. 8025/8026/8027/8039/8028/8083). A level of epidioxy hydroperoxides produced by autooxidation of linolenate decreased by supplementation of antioxidants(Ref. 8094).

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)

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[8039]

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

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[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)

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[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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[8079]

AUTHOR	:	Terao, J., Inoue, T., Yamagata, S., Murakami, H., and Matsushita, S.
TITLE	:	Gas Chromatography Mass Spectrometric Analysis of Monohydroperoxide Isomers and Their Secondary Oxidation Products of Methyl Linoleate and Methyl Linolenate
JOURNAL	:	Agric. Biol. Chem.
VOL	:	48 PAGE : 1735 -1743 (1984)

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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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[8094]

AUTHOR	:	Peers, K. E., Coxon, D. T., and Chan, H. W. - S.
TITLE	:	Autoxidation of Methyl Linolenate. The Effect of Antioxidants on Product Distribution
JOURNAL	:	J. Sci. Food Agric.
VOL	:	35 PAGE : 813 -817 (1984)

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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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