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Fatty acid


DATA No : DFA8050 INFORMANT : Tetsuyuki Kobayashi

NAME : 9-Hydroperoxy-10,12,15-Octadecatrienoic Acid/9-Hydroperoxy-10,12,15-Octadecatrienoate

COMMON NAME:
SYMBOL:
FORMULA: C18H30O4 MOL.WT (average) : 310.428


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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:(Me-ester; after reduction; in etoh)(Ref. 8076), trans, cis, cis isomer: lmax=236nm trans, trans, cis isomer: lmax=232nm

IR SPECTRA:(Me-ester; after reduction)(Ref. 8076/8077), trans, cis, cis isomer:9 88-983 AND 951-945cm-1; trans, trans, cis isomer: 992-983cm-1 (Me-ester)(Ref. 8078), OOH group: 3400cm-1

NMR SPECTRA:

MASS SPECTRA:EI-MS(Me-ester; after reduction and hydrogenation)(Ref. 8020/8076): m/e=187[O=CH(CH2)7C(=OH)OCH3]; 158[CH2(CH2)6C(=OH)OCH3]; 155[O=CH(CH2)7C=O], GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8090/8077): m/e=380[M]; 365[M-CH3]; 223[SMTO=CH-CH=CH-CH=CH-CH2-CH=CH-CH2CH3]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Auto oxidation of linoleate(Ref. 8090/8022/8023/8021/8024/8025/8026/8027/8030/8028). Oxidation of linoleate by singlet oxygen(Ref. 8022/8023/8024/8025/8026/8027/8030). Reaction products between linoleate and linseed lipoxygenase(pH6.5, 24degC)(Ref. 8016).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8016]
AUTHOR:Zimmerman, D. C., and Vick, B. A.
TITLE:Specificity of flaxseed lipoxidase PubMed ID:5447012
JOURNAL:Lipids.
VOL:5 PAGE : 392-397 (1970)
[TOP]

[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)
[TOP]

[8021]
AUTHOR:Frankel, E. N.( 1979 ) Autoxidation, in Fatty Acids ( Pryde, E. H., eds.), pp353-378, American Oil Chemists' Society, Champaign, IL.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8022]
AUTHOR:Mathusita, S.( 1982 ) Oxidative Products of Unsaturated Fatty Acids, in Nutrition and Foods, pp375-390 (in Japanese)
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[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]

[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]

[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 : - ()
[TOP]

[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 : - ()
[TOP]

[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)
[TOP]

[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 : - ()
[TOP]

[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 : - ()
[TOP]

[8076]
AUTHOR:Chan, H. W. - S.,And Levett, G.
TITLE:Autoxidation of Methyl Linolenate: Analysis of Methyl Hydroxylinolenate Isomers by High Performance Liquid Chromatography.
JOURNAL:Lipids
VOL:12 PAGE : 837 -840 (1977)
[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)
[TOP]

[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)
[TOP]

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