Fatty acid
DATA No : DFA8001
INFORMANT : Tetsuyuki Kobayashi
NAME : 9-Hydroperoxy-10,12-Octadecadienoic Acid/9-Hydroperoxy-10,12-Octadecadienoate
| COMMON NAME | : | |
| SYMBOL | : | |
| FORMULA | : | C18H32O4 MOL.WT (average) : 312.444 |
| PHYSICAL AND CHEMICAL PROPERTIES |
| MELTING POINT | : | |
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| BOILING POINT | : | |
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| REFRACTIVE INDEX | : | |
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| OPTICAL ROTATION | : | |
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| DENSITY | : | |
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| SOLUBILITY | : | |
| UV SPECTRA | : | Trans, cis isomer: l max=236nm, e =25900, trans, trans isomer: l max=233nm, e=28600 (Ref. 8001/8002/8003/8004/8005/8011) |
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| IR SPECTRA | : | Methyl ester: (Ref. 8001/8005/8006/8007/8008/8009/8010/8011): trans, cis isomer: 986 and 949cm-1, trans, trans isomer: 989cm-1, OOH group: 3550cm-1 |
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| NMR SPECTRA | : | 1H-NMR(Ref. 8001/8012), 1H-NMR( after methanolyzation and reduction)(Ref. 8005/8017): trans,cis isomer: C10-13 (5.42-6.48ppm), C14 (2.10-2.18ppm), C9(4.15ppm), J10-11= 15.4Hz(trans), J12-13= 10.8Hz (cis), trans, trans isomer: olefinic protons (5.41ppm), C14 (2.07ppm), C9 (4.20ppm)
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| MASS SPECTRA | : | GC/EI-MS(after methanolysis, reduction and trimethylsilylation) (Ref. 8012/8018/8013/8019/8014): m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3] standard peak/ GC-EI-MS(after methylation, reduction and hydrogenation) (Ref. 8020/8015/8016): m/e= 187[CH(OH)(CH2)7COOCH3], 158[(CH2)7COOCH3+H], 155[C(OH)-(CH)7CO]
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| OTHER SPECTRA | : |
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[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) |
[8002]
| AUTHOR | : | Bolland, J.L., and Koch, H.P. |
| TITLE | : | The Course of Autoxidation Reactions in Polyisoprenes and Allied Compounds. IX. The Primary Thermal Oxidation Products of Ethyl Linoleate. |
| JOURNAL | : | J. Chem. Soc. |
| VOL | : | PAGE : 445 -447 (1945) |
[8003]
| AUTHOR | : | Lundberg, W.O., and Chipault, J.R. |
| TITLE | : | The Oxidation of Methyl Linoleate at Various Temperatures |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 69 PAGE : 833 -836 (1947) |
[8004]
| AUTHOR | : | Lundberg, W. O., Chipault, J. R., and Hendrickson, N. J. |
| TITLE | : | Observation on The Mechanism of The Autoxidation of Methyl Linolate |
| JOURNAL | : | J. Am. Cil Chem. Soc. |
| VOL | : | 26 PAGE : 109 -115 (1949) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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 : - () |
[8022]
| AUTHOR | : | Mathusita, S.( 1982 ) Oxidative Products of Unsaturated Fatty Acids, in Nutrition and Foods, pp375-390 (in Japanese) |
| TITLE | : | |
| JOURNAL | : | |
| VOL | : | PAGE : - () |
[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 : - () |
[8024]
| AUTHOR | : | Frankel, E. N. |
| TITLE | : | Lipid oxidation PubMed ID:7232452 |
| JOURNAL | : | Prog Lipid Res. |
| VOL | : | 19 PAGE : 1-22 (1980) |
[8025]
| AUTHOR | : | Frankel, E. N. |
| TITLE | : | Volatile lipid oxidation products PubMed ID:6306693 |
| JOURNAL | : | Prog Lipid Res. |
| VOL | : | 22 PAGE : 1-33 (1983) |
[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) |
[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 : - () |
[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) |
[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 : - () |
[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 : - () |
[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 : - () |
[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 : - () |
[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 : - () |
[8034]
| AUTHOR | : | Mathuo, M. |
| TITLE | : | Synthesis of Lipid Peroxides and Their Physiological Effects. |
| JOURNAL | : | Fragrance J. (in Japanese) |
| VOL | : | 76 PAGE : 15 -20 (1986) |
[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 : - () |
[8036]
| AUTHOR | : | Wakabayashi, T. |
| TITLE | : | Lipoxygenase Reaction of Unsaturated Fatty Acids |
| JOURNAL | : | Chemistry and Biology (in Japanese) |
| VOL | : | 18 PAGE : 558 -564 (1980) |
[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 : - () |
[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 : - () |
[8039]
| AUTHOR | : | Frankel, E. N. |
| TITLE | : | Secondary products of lipid oxidation PubMed ID:3311422 |
| JOURNAL | : | Chem Phys Lipids. |
| VOL | : | 44 PAGE : 73-85 (1987) |
[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) |
[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 : - () |
[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 : - () |
[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) |
[8047]
| AUTHOR | : | Fujimoto, K. |
| TITLE | : | Toxicity and Safety of Lipid Peroxidates |
| JOURNAL | : | Fragrance J. (in Japanese) |
| VOL | : | 76 PAGE : 21 -25 (1986) |
[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 : - () |
[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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