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Fatty acid


DATA No : DFA8082 INFORMANT : Tetsuyuki Kobayashi

NAME : 11-Hydroperoxy-5,8,12,14-Eicosatetraenoic Acid/11-Hydroperoxy-5,8,12,14-Eicosatetraenoate

COMMON NAME:
SYMBOL:
FORMULA: C20H32O4 MOL.WT (average) : 336.466


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BIOLOGICAL ACTIVITY
11-HPETE generated by 11-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE(Ref. 8100/8101/8102/8103/8104).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:UV(Ref. 8099) conjugated diene: lmax=235nm, UV(Me-ester)(Ref. 8098) conjugated diene: lmax=232.5nm, UV(Me-ester; after reduction)(Ref. 8105) conjugated trans, cis diene:lmax=236nm, conjugated trans, trans diene: lmax=232.5

IR SPECTRA:IR(Ref. 8099): conjugated trans, cis diene: 985, 950cm-1, OOH group: 3400cm-1, IR(Me-ester; after reduction)(Ref. 8105)conjugated trans, cis diene: 985, 950cm-1, conjugated trans, trans diene: 989cm-1

NMR SPECTRA:

MASS SPECTRA:GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8080/8098/8116), GC-EI-MS(Me-ester; after reduction and TBDMS)(114), GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS)(Ref. 8080/8098/8099/8105/8120), GC-EI-MS(Me-ester; after reduction, hydrogenation and TBDMS)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Autooxidation of arachidonic acid(Ref. 8080/8097/8105). Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098/8099). Reaction products between arachidonic acid and lipoxygenase from living cells(11-HPETE)(Ref. 8100/8102).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE
Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation(Ref. 8080/8097/8106). However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol(Ref. 8041/8080/8106).
REFERENCES
[8041]
AUTHOR:Porter, N. A., Lehman, I. S., Weber, B. A. and Smith, K. J.
TITLE:Unified Mechanism for Polyunsaturated Fatty Acid Autoxidation. Competition of Radical Hydrogen Atom Abstraction, b-Scission, and Cyclization
JOURNAL:J. Am. Chem. Soc.
VOL:103 PAGE : 6447 -6455 (1981)
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[8080]
AUTHOR:Terao, J., and Matsushita, S.
TITLE:Analysis of Hemoprotein Catalyzed Peroxidation Products of Arachidonic Acid by Gas Chromatography- Mass Spectrometry
JOURNAL:Agric. Biol. Chem.
VOL:45 PAGE : 595 -599 (1981)
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[8097]
AUTHOR:Yamagata, S., Murakami, H., Terao, J., and Matsushita, S.
TITLE:Nonenzymatic Oxidation Products of Methyl Arachidonate
JOURNAL:Agric. Biol. Chem.
VOL:47 PAGE : 2791 -2799 (1983)
[TOP]

[8098]
AUTHOR:Terao, J.,And Matsushita, S.
TITLE:The Isomeric Compositions of Hydroperoxides Produced by Oxidation of Arachidonic Acid with Singlet Oxygen
JOURNAL:Agric. Biol. Chem.
VOL:45 PAGE : 587 -593 (1981)
[TOP]

[8099]
AUTHOR:Porter, N. A., Logan, J., and Kontoyiannidou, V.
TITLE:Preparation and Purification of Arachidonic Acid Hydroperoxides of Biological Importance
JOURNAL:J. Org. Chem.
VOL:44 PAGE : 3177 -3181 (1979)
[TOP]

[8100]
AUTHOR:Murota, S.(1982) An Outline of Prostaglandins, in Biochemistry of Prosatglandins (Murota, S., ed.), pp3-26, Tokyo Kagaku Dojin, Japan (in Japanese)
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8101]
AUTHOR:Spector, A. A., Gordon, J. A., and Moore, S. A.
TITLE:Hydroxyeicosatetraenoic acids (HETEs) PubMed ID:3076240
JOURNAL:Prog Lipid Res.
VOL:27 PAGE : 271-323 (1988)
[TOP]

[8102]
AUTHOR:Pace- Asciak, C. R., and Smith, W. L.(1983) Enzymes in The Biosynthesis and Catabolism of The Eicosanoids: Prostaglandins, Thromboxanes, Leukotriens and Hydroxy Fatty Acids, In The Enzymes (Boyer, P. D., Ed.), Vol.16, pp543-603, Academic Press New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8103]
AUTHOR:Shimizu, T.
TITLE:A Recent Advance in Studies on Leukotriens (in Japanese)
JOURNAL:Taisha
VOL:24 PAGE : 203 -214 (1987)
[TOP]

[8104]
AUTHOR:Yamamoto, N.(1987) 1. A New Advance in Study on Prostaglandins, 2. Chemistry and Biochemistry, in An Advance in Recent Study on Prostaglandins, pp.1-86, Kodansha Scientific, Tokyo, Japan (in Japanese)
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8105]
AUTHOR:Porter, N. A., Wolf, R. A., Yarbro, E. M., and Weenen, H.
TITLE:The autoxidation of arachidonic acid: formation of the proposed SRS-A intermediate PubMed ID:496937
JOURNAL:Biochem Biophys Res Commun.
VOL:89 PAGE : 1058-1064 (1979)
[TOP]

[8106]
AUTHOR:Peers, K. E., and Coxon, D. T.
TITLE:Controlled Synthesis of Monohydroperoxides by a- Tocopherol Inhibited Autoxidation of Polyunsaturated Lipids
JOURNAL:Chem. Phys. Lipids
VOL:32 PAGE : 49 -56 (1983)
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[8116]
AUTHOR:Rabinovitch, H., Durand, J., Rigaud, M., Mendy, F., and Breton, J. C.
TITLE:Transformation of arachidonic acid into monohydroxy-eicosatetraenoic acids by mouse peritoneal macrophages PubMed ID:7278513
JOURNAL:Lipids.
VOL:16 PAGE : 518-524 (1981)
[TOP]

[8120]
AUTHOR:Mayer, B., Moser, R., Gleispach, H., and Kukovetz, W. R.
TITLE:Possible inhibitory function of endogenous 15-hydroperoxyeicosatetraenoic acid on prostacyclin formation in bovine aortic endothelial cells PubMed ID:3081039
JOURNAL:Biochim Biophys Acta.
VOL:875 PAGE : 641-653 (1986)
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