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Fatty acid


DATA No : DFA8002 INFORMANT : Tetsuyuki Kobayashi

NAME : 13- Hydroperoxy-9,11-Octadecadienoic Acid/13- Hydroperoxy-9,11-Octadecadienoate

COMMON NAME:
SYMBOL:
FORMULA: C18H32O4 MOL.WT (average) : 312.444


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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)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:Trans, cis isomer: l max= 236nm, e= 26000, trans, trans isomer: l max= 233nm, e=28600 (025/027/028/029/036)

IR SPECTRA:Methyl ester(Ref. 8001/8006/8007/8008/8009/8010/8011): cis, trans isomer: 986 and 949cm-1, trans, trans isomer: 989cm-1, OOH group: 3550cm-1

NMR SPECTRA:1H-NMR (Ref. 8001/8012): C9-13 (5.45-6.53ppm), C13 (4.37ppm), J9-10= 11Hz (cis),J11-12=15Hz (trans) /1H-NMR (after methanolyzation and reduction )(Ref. 8005/8017): cis, trans isomer : olefinic protons(5.91ppm), C8 (2.10ppm), C13(4.15ppm), trans, trans isomer: olefinic protons (5.41ppm), C8 (2.07ppm)

MASS SPECTRA:GC-EI-MS(after methanolysis, reduction and trimethylsilylation) (Ref. 8012/8018/8019/8013/8014): m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3] standard peak,225[M-(CH2)7COOCH3] / GC-EI-MS(after methylation, reduction and hydrogenation) (Ref. 8020/8015/8016): m/e= 243[CH(OH)(CH2)11COOCH3], 214[(CH2)11COOCH3+H], 211[C(OH(CH2)11CO]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Auto oxidation of methyl linoleate(Ref. 8029/8021/8022/8023/8024/8025/8026/8039/8028/8030). Oxidation of methyl linoleate by singlet oxygen(Ref. 8022/8023/8025/8026/8027/8030/8024). Oxidation of linoleic acid by lipoxygenase(Ref. 8023/8031/8032/8033/8034/8035/8037/8038/8036). Production mechanism (auto oxidation): bis-allylic hydrogen at C11.
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8001]
AUTHOR:Chan, H. W., and Levett, G.
TITLE:Autoxidation of methyl linoleate. Separation and analysis of isomeric mixtures of methyl linoleate hydroperoxides and methyl hydroxylinoleates PubMed ID:834127
JOURNAL:Lipids.
VOL:12 PAGE : 99-104 (1977)
[TOP]

[8005]
AUTHOR:Gardner, H. W., and Weisleder, D.
TITLE:Lipoxygenase from Zea Mays: 9-D-Hydroperoxy-trans-10, cis-12-Octadecadienoic Acid
JOURNAL:Lipids
VOL:5 PAGE : 678 -683 (1970)
[TOP]

[8006]
AUTHOR:Cannon, J. A., Zilch, K. T., Burket, S. C., and Dutton, H. J.
TITLE:Analysis of Fat Acid Oxidation Products by Countercurrent Distribution Methods. IV. Methyl Linoleate
JOURNAL:J. Am. Oil Chem. Soc.
VOL:29 PAGE : 447 -452 (1952)
[TOP]

[8007]
AUTHOR:Privett, O. S., Lundberg, W. O.,Khan, N. A., Tolberg, W. E., and Wheeler, D. H.
TITLE:Structure of Hydroperoxides Obtained from Autoxidized Methyl Linoleate
JOURNAL:J. Am. Oil Chem Soc.
VOL:30 PAGE : 61 -66 (1953)
[TOP]

[8008]
AUTHOR:Sephton, H. H., and Sutton, D. A.
TITLE:The Chemistry of Polymerized Oils. V. The Autoxidation of Methyl Linoleate
JOURNAL:J. Am. Oil Chem Soc.
VOL:33 PAGE : 263 -272 (1956)
[TOP]

[8009]
AUTHOR:Graceland, A.
TITLE:Enzymatic Oxidation of Linoleic Acid and Grycerol-1-monolinoleate in Doughs and Flour-Water Suspensions
JOURNAL:J. Am. Oil Chem Soc.
VOL:47 PAGE : 352 -361 (1970)
[TOP]

[8010]
AUTHOR:Privett, O. S., Nickell, C., Lundberg, W. O., and Boyer, P. D.
TITLE:Products of The Lipoxidase -Catalyzed Oxidation of Sodium Linoleate
JOURNAL:J. Am. Oil Chem Soc.
VOL:32 PAGE : 505 -511 (1955)
[TOP]

[8011]
AUTHOR:Gardner, H. W., and Weisleader, D.
TITLE:Hydroperoxides from Oxidation of Linoleic and Linolenic Acids by Soybean Lipoxygenase: Proof of The trans-11 Double Bond
JOURNAL:Lipids
VOL:7 PAGE : 191 -193 (1972)
[TOP]

[8012]
AUTHOR:Frankel, E. N., Neff, W. E., Rohwedder, W. K., Khambay, B. P., Garwood, R. F., and Weedon, B. C.
TITLE:Analysis of autoxidized fats by gas chromatography-mass spectrometry: II. Methyl linoleate PubMed ID:927043
JOURNAL:Lipids.
VOL:12 PAGE : 908-913 (1977)
[TOP]

[8013]
AUTHOR:Gardner, H. W., Kleiman, R., and Weisleder, D.
TITLE:Homolytic Decomposition of Linoleic Acid Hydroperoxide: Identification of Fatty Acid Products
JOURNAL:Lipids
VOL:9 PAGE : 696 -706 (1974)
[TOP]

[8014]
AUTHOR:Hamberg, M.
TITLE:Decomposition of unsaturated fatty acid hydroperoxides by hemoglobin: Structures of major products of 13L-hydroperoxy-9,11-octadecadienoic acid PubMed ID:1167926
JOURNAL:Lipids.
VOL:10 PAGE : 87-92 (1975)
[TOP]

[8015]
AUTHOR:Dolev, A., Rohwedder, W. K., and Dutton, H. J.
TITLE:Mechanism of Lipoxidase Reaction. I. Specificity of Hydroperoxidation of Linoleic Acid
JOURNAL:Lipids
VOL:2 PAGE : 28 -32 (1967)
[TOP]

[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]

[8017]
AUTHOR:Neff, W. E., Frankel, E. N., Scholfield, C. R., and Wesleder, D.
TITLE:High-Pressure Liquid Chromatgraphy of Autoxidized Lipids: I. Methyl Oleate and Linoleate
JOURNAL:Lipids
VOL:13 PAGE : 415 -421 (1978)
[TOP]

[8018]
AUTHOR:Kleiman, R., and Spencer, G. F.
TITLE:Gas Chromatgrphy-Mass Spectrometry of Methyl Esters of Unsaturated Oxygenated Fatty Acids
JOURNAL:J. Am. Oil Chem Soc.
VOL:50 PAGE : 31 -38 (1973)
[TOP]

[8019]
AUTHOR:Frankel, E. N., Neff, W. E., and Bessler, T. R.
TITLE:Analysis of Autoxidized Fats by Gas Chromatgraphy-Mass Spectrometry: V. Photosensitized Oxidation
JOURNAL:Lipids
VOL:14 PAGE : 961 -967 (1979)
[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]

[8029]
AUTHOR:Frankel, E. N.(1962 ) Hydroperoxides, in Symposium on Foods: Lipids and Their Oxidation (Shulz, H. W., eds.), pp51-78,Avipubl., Westport, CT.
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]

[8031]
AUTHOR:Schewe, T., Rapoport, S. M., and Kuhn, H.(1986 ) Enzymology and Physiology of Reticulocyte Lipoxygenase: Comparison with Other Lipoxygenase, in Advancs in Enzymology (Meister, A., eds.), pp191-272, An Interscience, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8032]
AUTHOR:Whitaker, J. R.(1985 ) Mechanism of Oxidoreductases Important in Food Component Modification, in Chemical Changes in Food During Processing ( Richardson, T. and Finley, J. W., eds.), pp121-176, Avipubl, Westport, CT.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8033]
AUTHOR:Chism, G. W.( 1985 ) Soy Lipoxygenase, in Flavor Chemistry of Fats and Oils ( Min, D. B. and Smouse, T. H., eds.), pp175-188, American Oil Chemists' Sosiety, Champaign, IL.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8034]
AUTHOR:Mathuo, M.
TITLE:Synthesis of Lipid Peroxides and Their Physiological Effects.
JOURNAL:Fragrance J. (in Japanese)
VOL:76 PAGE : 15 -20 (1986)
[TOP]

[8035]
AUTHOR:Veldink, G. A., Vligenthart, J. F. G., and Boldingh, J.( 1977 ) Plant Lipoxygenases, in Progress in The Chemistry of Fats and Other Lipids ( Holman, R. T., ed.), pp131-166 (15 ), Pergamon Press, London
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8036]
AUTHOR:Wakabayashi, T.
TITLE:Lipoxygenase Reaction of Unsaturated Fatty Acids
JOURNAL:Chemistry and Biology (in Japanese)
VOL:18 PAGE : 558 -564 (1980)
[TOP]

[8037]
AUTHOR:Vliegenthart, J. F. G., and Veldink, G. A.(1979 ) Lipoxygenase-Catalized Oxidation of Linoleic Acid, in Autoxidation in Food and Biological Systems ( Simic, M. G., and Karel, M., eds.), pp529-540, Plenum Press, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8038]
AUTHOR:Kurn, H., Schewe, T., and Rapoport, S. M.( 1986 ) The Stereochemistry of The Reactions of Lipoxygenase and Their Metabolites. Proposed Nomenclature of Lipoxygenases and Related Enzymes, in Advances in Enzymology ( Meister, A., ed.), pp273-311, An Interscience, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[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]

[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]

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