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Fatty acid


DATA No : DFA8055 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-15-Hydroperoxy-9,12,16-Octadecatrienoate

COMMON NAME:
SYMBOL:
FORMULA: C19O32O4 MOL.WT (average) : 804.182


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BIOLOGICAL ACTIVITY
Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049). 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:

NMR SPECTRA:

MASS SPECTRA:EI-MS(Me-ester; after reduction and hydrogenation)(Ref. 8020): m/e=271[O=CH(CH2)13C(=OH)OCH3]; 242[CH2(CH2)12C(=OH)OCH3]; 239[O=CH(CH2)13C=O]; GC-EI-MS(Me-ester; after reduction and hydroganation)(Ref. 8090): m/e=143[SMTO=CH-CH=CH-CH3]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Oxidation of linoleate by singlet oxygen(Ref. 8022/8023/8024/8025/8026/8027/8030).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

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.
REFERENCES
[8020]
AUTHOR:Chan, H. W.-S.
TITLE:Photo-Sensitized Oxidation of Unsaturated Fatty Acids Methyl Esters. The Identification of Different Pathways
JOURNAL:J. Am. Oil Chem Soc.
VOL:54 PAGE : 100 -104 (1977)
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[8022]
AUTHOR:Mathusita, S.( 1982 ) Oxidative Products of Unsaturated Fatty Acids, in Nutrition and Foods, pp375-390 (in Japanese)
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[8023]
AUTHOR:Matsuo, M. (1985) Synthesis and Degradation of Lipid Peroxides, in Lipid Peroxides in Bodies (Yamauchi, M., Matsuo, M. and Sagai, M., eds.), pp13-44, Center for Academic Publications Japan
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8024]
AUTHOR:Frankel, E. N.
TITLE:Lipid oxidation PubMed ID:7232452
JOURNAL:Prog Lipid Res.
VOL:19 PAGE : 1-22 (1980)
[TOP]

[8025]
AUTHOR:Frankel, E. N.
TITLE:Volatile lipid oxidation products PubMed ID:6306693
JOURNAL:Prog Lipid Res.
VOL:22 PAGE : 1-33 (1983)
[TOP]

[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]

[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 : - ()
[TOP]

[8030]
AUTHOR:Miyagawa, T.(1987 ) Oxidative Reactions and Their Priventive Mechanisms, in Foods and Antioxidants ( Ohta, S., eds.), pp1-37, Coference on the Food Materials, Japan
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8043]
AUTHOR:Logani, M. K., and Davies, R. E.
TITLE:Lipid oxidation: biologic effects and antioxidants--a review PubMed ID:7401947
JOURNAL:Lipids.
VOL:15 PAGE : 485-495 (1980)
[TOP]

[8044]
AUTHOR:Tappel, A. L.( 1980 ) Free Radicals in Biology ( Pryor, W. A.,ed.),pp1-47 (4 ), Academic Press, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[8045]
AUTHOR:Miyazawa, Y (1985 ) II Hydroperoxides and Physiological Factor; 1-2: Foods, in Hydroperoxides and Body ( Uthiyama, M., Mathuo, M., and Sagano, M.,eds.), pp98-122, Press Center of Societies, Japan
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[8046]
AUTHOR:Sevanian, A., and Hochstein, P.
TITLE:Mechanisms and consequences of lipid peroxidation in biological systems PubMed ID:2992549
JOURNAL:Annu Rev Nutr.
VOL:5 PAGE : 365-390 (1985)
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[8047]
AUTHOR:Fujimoto, K.
TITLE:Toxicity and Safety of Lipid Peroxidates
JOURNAL:Fragrance J. (in Japanese)
VOL:76 PAGE : 21 -25 (1986)
[TOP]

[8048]
AUTHOR:Halliwell, B., and Gutteridge, J. M. C. (1988 ) Free Radical and Bodies ( Translated by Matsuo, M., Sagai, M., and Yoshikawa, T.), pp151-203, Center for Academic Publications Japan
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[8049]
AUTHOR:Miyazawa, T., Fujimoto, K., and Kaneda, T.( 1988 ) Lipid Peroxidation in Biological Systems ( Sevanian, A., ed.) pp1, American Oil Chemists' Society, Chanpaign, IL.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[8090]
AUTHOR:Terao, J., and Matsushita, S.
TITLE:Products Formed by Photosensitized Oxidation of Unsaturated Fatty Acid Esters
JOURNAL:J. Am. Oil Chem. Soc.
VOL:54 PAGE : 234 -238 (1977)
[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)
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